# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_uconn001_0m
_database_code_depnum_ccdc_archive 'CCDC 919810'
#TrackingRef '16861_web_deposit_cif_file_0_ChristianBrueckner_1358220260.JA-C-58F1_uconn001_0m(7a).cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H30 N4 O2'
_chemical_formula_weight         634.71
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0027 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175.'
H H 0.0000 0.0000 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175.'
N N -0.0031 0.0054 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175.'
O O -0.0042 0.0099 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175.'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
_cell_length_a                   11.016(3)
_cell_length_b                   6.7826(18)
_cell_length_c                   21.878(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.024(4)
_cell_angle_gamma                90.00
_cell_volume                     1604.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3044
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      32.03
_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.005
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS-2008/1 (Sheldrick, 2008)'
_exptl_special_details           
;
Reflection 1 0 1 was partially obstructed by the beam stop and was
omitted from the refinement.
The structure shows three fold disorder. The asymmetric molecule is
disordered around a crystallographic inversion center in the middle
of the molecule. leading to disorder of a lactone moiety from one
side of the molecule with a beta,beta-reduced pyrrole on the opposite
side in a 1:1 ratio. The lactone moiety is additionally disordered
with refined occupancy ratios of 0.249(4) to 0.251(4).
Due to the disorder bond distances were restrained and ADPs
constrained. C-C and C-O bond distances and C...C and C...O distances
in the disordered lactone parts of the molecule were restrained to
have lengths similar to equivalent values in not disordered well
defined molecules taken from the CSD. The C-C lactone bonds were
restrained to 1.465(20), the C-O bonds to 1.390(20), the 1,3 C...O
distances to 2.27(2) and the 1,3 C...C distances to 2.21 Angstroms.
The beta,beta-reduced pyrrole was restrained to be flat and the two
equivalent C-C bonds to be similar. All overlapping atoms were
constrained to have identical ADPs.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.88560
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_measurement_device_type  'Bruker AXS APEXII CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14751
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         33.53
_reflns_number_total             3227
_reflns_number_gt                2278
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'Bruker APEX2 v2010.3.0'
_computing_cell_refinement       'Bruker SAINT v7.60A'
_computing_data_reduction        'Bruker SAINT v7.60A'
_computing_structure_solution    
'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_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^)+(0.0578P)^2^+0.2585P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3227
_refine_ls_number_parameters     248
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.034
_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 0.24996(15) 0.4563(2) 0.62271(7) 0.0358(4) Uani 1 1 d . . .
C2 C 0.15667(15) 0.3133(2) 0.61743(7) 0.0344(4) Uani 1 1 d D . .
C3 C 0.1691(15) 0.147(2) 0.6639(8) 0.0465(13) Uani 0.50 1 d PD A 1
H3A H 0.1737 0.1966 0.7068 0.056 Uiso 0.50 1 calc PR A 1
H3B H 0.2432 0.0655 0.6624 0.056 Uiso 0.50 1 calc PR A 1
C4 C 0.0465(15) 0.026(2) 0.6411(7) 0.0428(13) Uani 0.50 1 d PD A 1
H4A H 0.0643 -0.1096 0.6283 0.051 Uiso 0.50 1 calc PR A 1
H4B H -0.0046 0.0188 0.6737 0.051 Uiso 0.50 1 calc PR A 1
C3A C 0.155(3) 0.138(6) 0.658(2) 0.0465(13) Uani 0.249(4) 1 d PD A 2
O1A O 0.2165(5) 0.0511(9) 0.6993(2) 0.0534(19) Uani 0.249(4) 1 d PD A 2
O2A O 0.046(2) 0.041(4) 0.6341(12) 0.0428(13) Uani 0.249(4) 1 d PD A 2
C3B C 0.057(3) 0.056(5) 0.6430(17) 0.0428(13) Uani 0.251(4) 1 d PD A 3
O1B O 0.0587(5) -0.0845(8) 0.6740(3) 0.061(2) Uani 0.251(4) 1 d PD A 3
O2B O 0.162(2) 0.169(4) 0.6597(13) 0.0465(13) Uani 0.251(4) 1 d PD A 3
C5 C -0.01535(14) 0.1481(2) 0.58621(7) 0.0327(4) Uani 1 1 d D . .
C6 C -0.13034(14) 0.0862(2) 0.55317(8) 0.0335(4) Uani 1 1 d . A .
C7 C -0.19494(15) 0.1715(2) 0.49809(8) 0.0342(4) Uani 1 1 d . . .
C8 C -0.31650(15) 0.1197(3) 0.46627(8) 0.0417(4) Uani 1 1 d . A .
H8 H -0.3659 0.0156 0.4772 0.050 Uiso 1 1 calc R . .
C9 C -0.34916(16) 0.2474(3) 0.41701(8) 0.0417(4) Uani 1 1 d . . .
H9 H -0.4250 0.2463 0.3878 0.050 Uiso 1 1 calc R A .
C10 C -0.24955(14) 0.3813(2) 0.41746(8) 0.0356(4) Uani 1 1 d . . .
C11 C 0.36149(15) 0.4335(3) 0.67368(8) 0.0377(4) Uani 1 1 d . . .
C12 C 0.43872(16) 0.2705(3) 0.67541(8) 0.0416(4) Uani 1 1 d . A .
H12 H 0.4209 0.1721 0.6441 0.050 Uiso 1 1 calc R . .
C13 C 0.54196(17) 0.2508(3) 0.72283(10) 0.0517(5) Uani 1 1 d . . .
H13 H 0.5938 0.1385 0.7237 0.062 Uiso 1 1 calc R A .
C14 C 0.56944(18) 0.3901(3) 0.76786(9) 0.0571(6) Uani 1 1 d . A .
H14 H 0.6402 0.3750 0.8000 0.068 Uiso 1 1 calc R . .
C15 C 0.4951(2) 0.5526(3) 0.76702(9) 0.0572(6) Uani 1 1 d . . .
H15 H 0.5147 0.6498 0.7986 0.069 Uiso 1 1 calc R A .
C16 C 0.39071(17) 0.5763(3) 0.72001(8) 0.0478(5) Uani 1 1 d . A .
H16 H 0.3397 0.6894 0.7196 0.057 Uiso 1 1 calc R . .
C17 C -0.19518(14) -0.0793(2) 0.57955(8) 0.0347(4) Uani 1 1 d . . .
C18 C -0.24083(18) -0.0515(3) 0.63391(9) 0.0506(5) Uani 1 1 d . A .
H18 H -0.2281 0.0712 0.6551 0.061 Uiso 1 1 calc R . .
C19 C -0.30455(18) -0.2001(3) 0.65752(9) 0.0537(5) Uani 1 1 d . . .
H19 H -0.3346 -0.1788 0.6949 0.064 Uiso 1 1 calc R A .
C20 C -0.32472(16) -0.3772(3) 0.62754(9) 0.0458(5) Uani 1 1 d . A .
H20 H -0.3694 -0.4783 0.6436 0.055 Uiso 1 1 calc R . .
C21 C -0.2798(2) -0.4073(3) 0.57415(11) 0.0587(6) Uani 1 1 d . . .
H21 H -0.2932 -0.5301 0.5531 0.070 Uiso 1 1 calc R A .
C22 C -0.2143(2) -0.2588(3) 0.55051(10) 0.0538(5) Uani 1 1 d . A .
H22 H -0.1826 -0.2823 0.5137 0.065 Uiso 1 1 calc R . .
N1 N 0.05093(12) 0.30754(19) 0.57374(6) 0.0332(3) Uani 1 1 d . A .
N2 N -0.15737(12) 0.32872(19) 0.46640(6) 0.0337(3) Uani 1 1 d . A .
H2 H -0.0849 0.3870 0.4761 0.040 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
C1 0.0310(8) 0.0425(9) 0.0336(9) 0.0016(7) 0.0056(7) 0.0004(7)
C2 0.0307(8) 0.0423(9) 0.0303(8) 0.0035(7) 0.0062(7) 0.0012(7)
C3 0.039(2) 0.060(4) 0.040(2) 0.014(3) 0.0083(14) 0.0097(17)
C4 0.049(2) 0.037(3) 0.046(3) 0.011(3) 0.0193(14) 0.0022(13)
C3A 0.039(2) 0.060(4) 0.040(2) 0.014(3) 0.0083(14) 0.0097(17)
O1A 0.042(3) 0.070(4) 0.043(3) 0.007(3) -0.004(2) -0.010(3)
O2A 0.049(2) 0.037(3) 0.046(3) 0.011(3) 0.0193(14) 0.0022(13)
C3B 0.049(2) 0.037(3) 0.046(3) 0.011(3) 0.0193(14) 0.0022(13)
O1B 0.055(3) 0.054(4) 0.069(4) 0.028(3) -0.001(3) -0.014(3)
O2B 0.039(2) 0.060(4) 0.040(2) 0.014(3) 0.0083(14) 0.0097(17)
C5 0.0327(8) 0.0329(8) 0.0350(9) 0.0034(7) 0.0130(7) 0.0010(7)
C6 0.0339(8) 0.0309(8) 0.0378(9) 0.0004(7) 0.0125(7) -0.0001(7)
C7 0.0344(9) 0.0320(8) 0.0379(9) -0.0013(7) 0.0110(7) -0.0020(7)
C8 0.0405(10) 0.0385(10) 0.0451(10) 0.0010(8) 0.0060(8) -0.0098(8)
C9 0.0350(9) 0.0430(10) 0.0441(10) 0.0030(8) 0.0002(8) -0.0064(8)
C10 0.0325(8) 0.0382(9) 0.0351(9) 0.0009(7) 0.0043(7) -0.0020(7)
C11 0.0329(9) 0.0453(10) 0.0349(9) 0.0064(8) 0.0065(7) -0.0064(7)
C12 0.0353(9) 0.0467(10) 0.0423(10) 0.0063(8) 0.0060(8) -0.0047(8)
C13 0.0369(10) 0.0591(12) 0.0571(12) 0.0195(10) 0.0038(9) -0.0028(9)
C14 0.0436(11) 0.0696(14) 0.0506(12) 0.0216(11) -0.0099(9) -0.0145(10)
C15 0.0624(13) 0.0666(14) 0.0386(10) -0.0005(10) -0.0009(9) -0.0211(11)
C16 0.0498(11) 0.0517(11) 0.0411(10) 0.0007(9) 0.0070(8) -0.0043(9)
C17 0.0308(8) 0.0355(9) 0.0388(9) 0.0036(7) 0.0090(7) -0.0020(7)
C18 0.0585(12) 0.0521(11) 0.0455(10) -0.0083(9) 0.0207(9) -0.0190(9)
C19 0.0558(12) 0.0640(13) 0.0465(11) -0.0026(10) 0.0232(9) -0.0184(10)
C20 0.0373(9) 0.0447(10) 0.0579(12) 0.0150(9) 0.0155(8) -0.0041(8)
C21 0.0740(14) 0.0316(10) 0.0804(15) -0.0019(10) 0.0395(12) -0.0067(9)
C22 0.0738(14) 0.0342(10) 0.0647(13) -0.0031(9) 0.0414(11) -0.0047(9)
N1 0.0301(7) 0.0367(8) 0.0339(7) 0.0020(6) 0.0090(6) -0.0026(6)
N2 0.0295(7) 0.0350(7) 0.0363(7) 0.0024(6) 0.0055(6) -0.0045(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
C1 C2 1.402(2) . ?
C1 C10 1.409(2) 3_566 ?
C1 C11 1.501(2) . ?
C2 O2B 1.338(16) . ?
C2 N1 1.359(2) . ?
C2 C3A 1.483(17) . ?
C2 C3 1.510(13) . ?
C3 C4 1.577(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.511(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3A O1A 1.182(15) . ?
C3A O2A 1.382(17) . ?
O2A C5 1.346(16) . ?
C3B O1B 1.169(15) . ?
C3B O2B 1.376(17) . ?
C3B C5 1.481(17) . ?
C5 N1 1.362(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.402(2) . ?
C6 C17 1.504(2) . ?
C7 N2 1.378(2) . ?
C7 C8 1.430(2) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.423(2) . ?
C9 H9 0.9500 . ?
C10 N2 1.375(2) . ?
C10 C1 1.409(2) 3_566 ?
C11 C12 1.391(2) . ?
C11 C16 1.394(3) . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.357(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.371(2) . ?
C17 C18 1.390(2) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.366(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N2 H2 0.8800 . ?
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 C10 125.09(15) . 3_566 ?
C2 C1 C11 118.25(14) . . ?
C10 C1 C11 116.63(14) 3_566 . ?
O2B C2 N1 112.6(7) . . ?
O2B C2 C1 120.9(7) . . ?
N1 C2 C1 126.46(15) . . ?
N1 C2 C3A 106.8(7) . . ?
C1 C2 C3A 126.7(7) . . ?
N1 C2 C3 114.1(5) . . ?
C1 C2 C3 119.5(5) . . ?
C2 C3 C4 102.4(8) . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
C4 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C5 C4 C3 101.2(8) . . ?
C5 C4 H4A 111.5 . . ?
C3 C4 H4A 111.5 . . ?
C5 C4 H4B 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
O1A C3A O2A 112.3(15) . . ?
O1A C3A C2 141.9(16) . . ?
O2A C3A C2 105.6(11) . . ?
C5 O2A C3A 107.7(12) . . ?
O1B C3B O2B 112.6(15) . . ?
O1B C3B C5 140.8(16) . . ?
O2B C3B C5 106.2(11) . . ?
C2 O2B C3B 107.4(12) . . ?
O2A C5 N1 112.2(7) . . ?
O2A C5 C6 120.7(7) . . ?
N1 C5 C6 127.06(14) . . ?
N1 C5 C3B 106.1(6) . . ?
C6 C5 C3B 126.8(7) . . ?
N1 C5 C4 114.7(5) . . ?
C6 C5 C4 118.2(5) . . ?
C5 C6 C7 125.57(15) . . ?
C5 C6 C17 118.40(14) . . ?
C7 C6 C17 115.96(14) . . ?
N2 C7 C6 126.86(15) . . ?
N2 C7 C8 106.78(14) . . ?
C6 C7 C8 126.24(15) . . ?
C9 C8 C7 107.88(15) . . ?
C9 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
C8 C9 C10 108.09(15) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
N2 C10 C1 127.07(14) . 3_566 ?
N2 C10 C9 107.07(14) . . ?
C1 C10 C9 125.76(15) 3_566 . ?
C12 C11 C16 118.51(16) . . ?
C12 C11 C1 120.75(15) . . ?
C16 C11 C1 120.74(16) . . ?
C11 C12 C13 120.32(18) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.02(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.89(19) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C22 C17 C18 117.93(16) . . ?
C22 C17 C6 121.84(15) . . ?
C18 C17 C6 120.20(15) . . ?
C19 C18 C17 120.86(18) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.58(18) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.26(17) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C22 120.40(18) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.95(18) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C2 N1 C5 107.60(13) . . ?
C10 N2 C7 110.15(13) . . ?
C10 N2 H2 124.9 . . ?
C7 N2 H2 124.9 . . ?
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
C10 C1 C2 O2B -177(2) 3_566 . . . ?
C11 C1 C2 O2B 5(2) . . . . ?
C10 C1 C2 N1 -0.6(3) 3_566 . . . ?
C11 C1 C2 N1 -178.64(15) . . . . ?
C10 C1 C2 C3A 179(4) 3_566 . . . ?
C11 C1 C2 C3A 1(4) . . . . ?
C10 C1 C2 C3 -180.0(10) 3_566 . . . ?
C11 C1 C2 C3 2.0(10) . . . . ?
O2B C2 C3 C4 63(26) . . . . ?
N1 C2 C3 C4 0.2(13) . . . . ?
C1 C2 C3 C4 179.6(8) . . . . ?
C3A C2 C3 C4 -9(26) . . . . ?
C2 C3 C4 C5 -1.1(13) . . . . ?
O2B C2 C3A O1A -41(22) . . . . ?
N1 C2 C3A O1A 173(9) . . . . ?
C1 C2 C3A O1A -6(12) . . . . ?
C3 C2 C3A O1A -15(17) . . . . ?
O2B C2 C3A O2A 146(35) . . . . ?
N1 C2 C3A O2A 0(5) . . . . ?
C1 C2 C3A O2A -179(2) . . . . ?
C3 C2 C3A O2A 172(31) . . . . ?
O1A C3A O2A C5 -178(5) . . . . ?
C2 C3A O2A C5 -3(6) . . . . ?
N1 C2 O2B C3B 2(4) . . . . ?
C1 C2 O2B C3B 179(3) . . . . ?
C3A C2 O2B C3B -34(29) . . . . ?
C3 C2 O2B C3B -116(28) . . . . ?
O1B C3B O2B C2 173(4) . . . . ?
C5 C3B O2B C2 -1(5) . . . . ?
C3A O2A C5 N1 4(4) . . . . ?
C3A O2A C5 C6 -179(4) . . . . ?
C3A O2A C5 C3B -37(20) . . . . ?
C3A O2A C5 C4 -138(33) . . . . ?
O1B C3B C5 O2A -31(15) . . . . ?
O2B C3B C5 O2A 140(25) . . . . ?
O1B C3B C5 N1 -172(7) . . . . ?
O2B C3B C5 N1 0(4) . . . . ?
O1B C3B C5 C6 10(9) . . . . ?
O2B C3B C5 C6 -179(2) . . . . ?
O1B C3B C5 C4 -11(10) . . . . ?
O2B C3B C5 C4 161(20) . . . . ?
C3 C4 C5 O2A 41(31) . . . . ?
C3 C4 C5 N1 1.8(12) . . . . ?
C3 C4 C5 C6 -179.6(8) . . . . ?
C3 C4 C5 C3B -18(16) . . . . ?
O2A C5 C6 C7 -171.5(19) . . . . ?
N1 C5 C6 C7 4.5(3) . . . . ?
C3B C5 C6 C7 -177(3) . . . . ?
C4 C5 C6 C7 -173.9(9) . . . . ?
O2A C5 C6 C17 11.7(19) . . . . ?
N1 C5 C6 C17 -172.32(14) . . . . ?
C3B C5 C6 C17 6(3) . . . . ?
C4 C5 C6 C17 9.3(9) . . . . ?
C5 C6 C7 N2 0.6(3) . . . . ?
C17 C6 C7 N2 177.50(14) . . . . ?
C5 C6 C7 C8 -175.01(16) . . . . ?
C17 C6 C7 C8 1.9(2) . . . . ?
N2 C7 C8 C9 -0.60(19) . . . . ?
C6 C7 C8 C9 175.72(16) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 N2 1.30(19) . . . . ?
C8 C9 C10 C1 -175.21(16) . . . 3_566 ?
C2 C1 C11 C12 62.1(2) . . . . ?
C10 C1 C11 C12 -116.13(18) 3_566 . . . ?
C2 C1 C11 C16 -118.57(18) . . . . ?
C10 C1 C11 C16 63.2(2) 3_566 . . . ?
C16 C11 C12 C13 0.6(2) . . . . ?
C1 C11 C12 C13 179.95(16) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
C1 C11 C16 C15 -179.88(16) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C5 C6 C17 C22 -113.6(2) . . . . ?
C7 C6 C17 C22 69.2(2) . . . . ?
C5 C6 C17 C18 68.2(2) . . . . ?
C7 C6 C17 C18 -108.93(19) . . . . ?
C22 C17 C18 C19 -0.6(3) . . . . ?
C6 C17 C18 C19 177.66(17) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C6 C17 C22 C21 -176.94(18) . . . . ?
C20 C21 C22 C17 -0.9(3) . . . . ?
O2B C2 N1 C5 -2(2) . . . . ?
C1 C2 N1 C5 -178.48(15) . . . . ?
C3A C2 N1 C5 2(3) . . . . ?
C3 C2 N1 C5 0.9(10) . . . . ?
O2A C5 N1 C2 -3.9(18) . . . . ?
C6 C5 N1 C2 179.80(15) . . . . ?
C3B C5 N1 C2 1(2) . . . . ?
C4 C5 N1 C2 -1.7(9) . . . . ?
C1 C10 N2 C7 174.75(16) 3_566 . . . ?
C9 C10 N2 C7 -1.70(18) . . . . ?
C6 C7 N2 C10 -174.84(16) . . . . ?
C8 C7 N2 C10 1.44(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        33.53
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033
# start Validation Reply Form
_vrf_DIFF020_I                   
;
PROBLEM: _diffrn_standards_interval_count and
RESPONSE: The data were collected with an area detector.
;
_vrf_DIFF022_I                   
;
PROBLEM: _diffrn_standards_decay_% is missing
RESPONSE: The data were collected with an area detector.
;
_vrf_PLAT430_I                   
;
PROBLEM: Short Inter D...A Contact O1A .. O1A .. 2.20 Ang.
RESPONSE: O1A is less than one quarter occupied, no short contacts
are present.
;


data_10mz486_0m
_database_code_depnum_ccdc_archive 'CCDC 919811'
#TrackingRef '16862_web_deposit_cif_file_1_ChristianBrueckner_1358220260.JH-A-23F1_10mz486_0m(8c).cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H38 F12 N6 O3'
_chemical_formula_weight         1010.87
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'
F F 0.0171 0.0103 '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                   12.801(4)
_cell_length_b                   12.814(4)
_cell_length_c                   14.782(5)
_cell_angle_alpha                81.419(5)
_cell_angle_beta                 75.271(5)
_cell_angle_gamma                84.415(5)
_cell_volume                     2314.3(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1268
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.38
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5941
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Apex2 v2009.7-0 (Bruker, 2009)'
_exptl_special_details           
;
The structure exhibits several types of disorder. Three of the four
trifluoromethyl groups show pronounced rotational disorder combined
with a slight sideways shifting of the adjacent phenyl rings. The
three units were refined as disordered over each two sites. The C-F
bonds, the F...F distances and the C-C(CF3) bonds within each site
were each restrained to be similar. The phenyl disordered phenyl
rings were constrained to resemble ideal hexagons with C-C distances
of 1.39 Angstrom. Overlapping disordered atoms were constrained to
have identical ADPs. The atoms C20 and C27b were constrained to be flat.
The occupancy ratios for the three groups refined to 0.798(5) to
0.202(5), 0.68(3) to 0.32(2), and 0.48(2) to 0.52(2).
The lactole moiety is flip disordered with the C=O and N-NH2 units
of the disordered units occupying mutually exclusive positions.
Associated with this disorder is disorder of two interstitial ethanol
molecules that are hydrogen bonded to the keto O and the amino groups.
The common occupancy ratio refined to 0.61(1) to 0.39(1).
The C-C(=O)-N(-N)-C units were each restrained to be flat and the
same for both moieties. The C=O and N-N distances were restrained to
be 1.2 and 1.44 Angstroms each. The overlapping atoms of each unit were
constrained to have identical ADPs, with the keto C atom also
restrained to be isotropic.
Equivalent bonds in the disordered ethanol molecules were restrained
to be similar. The 1,3 O...C distances were restrained to be 2.4
Angstrom. ADPs were restrained to be similar (SIMU and DELU commands
from the SHELXTL suite of programs) and to be close to isotropic.
Ethanol O-H and amine hydrogen atoms were placed based on hydrogen
bonding considerations and were initially refined using appropriate
restraints. In the final refinement cycles the O-H hydrogen atoms were
set to ride on their respective carrier O atom.
;
_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  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20289
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0880
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.03
_reflns_number_total             8112
_reflns_number_gt                4433
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'Apex2 v2009.7-0 (Bruker, 2009)'
_computing_cell_refinement       'Apex2 v2009.7-0'
_computing_data_reduction        'Apex2 v2009.7-0'
_computing_structure_solution    
'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_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^)+(0.0892P)^2^+1.7732P] 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_number_reflns         8112
_refine_ls_number_parameters     771
_refine_ls_number_restraints     327
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2130
_refine_ls_wR_factor_gt          0.1809
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.003
_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
C2 C 0.5083(3) 0.4492(3) 0.8278(2) 0.0401(9) Uani 1 1 d D . .
C3 C 0.5901(3) 0.3732(3) 0.7955(2) 0.0406(9) Uani 1 1 d D A .
C4 C 0.6149(3) 0.2783(3) 0.8500(2) 0.0390(9) Uani 1 1 d . . .
C5 C 0.6917(3) 0.1961(3) 0.8190(3) 0.0463(10) Uani 1 1 d . . .
H5 H 0.7347 0.1940 0.7565 0.056 Uiso 1 1 calc R . .
C6 C 0.6937(3) 0.1207(3) 0.8938(3) 0.0443(10) Uani 1 1 d . . .
H6 H 0.7392 0.0575 0.8928 0.053 Uiso 1 1 calc R B .
C7 C 0.6165(3) 0.1524(3) 0.9732(2) 0.0384(9) Uani 1 1 d . B .
C8 C 0.5893(3) 0.0979(3) 1.0649(2) 0.0409(10) Uani 1 1 d D . .
C9 C 0.5019(3) 0.1257(3) 1.1371(3) 0.0434(10) Uani 1 1 d . B .
C10 C 0.4721(4) 0.0616(3) 1.2289(3) 0.0543(12) Uani 1 1 d . . .
H10 H 0.5092 -0.0017 1.2496 0.065 Uiso 1 1 calc R B .
C11 C 0.3824(4) 0.1092(3) 1.2782(3) 0.0554(12) Uani 1 1 d . B .
H11 H 0.3439 0.0867 1.3410 0.066 Uiso 1 1 calc R . .
C12 C 0.3556(4) 0.2023(3) 1.2165(2) 0.0448(10) Uani 1 1 d . . .
C13 C 0.2641(3) 0.2699(3) 1.2432(2) 0.0446(10) Uani 1 1 d . B .
C14 C 0.2332(3) 0.3598(3) 1.1869(2) 0.0433(10) Uani 1 1 d . . .
C15 C 0.1355(3) 0.4232(3) 1.2076(3) 0.0453(10) Uani 1 1 d . B .
H15 H 0.0799 0.4144 1.2641 0.054 Uiso 1 1 calc R . .
C16 C 0.1348(4) 0.4993(3) 1.1325(3) 0.0473(11) Uani 1 1 d . . .
H16 H 0.0785 0.5522 1.1272 0.057 Uiso 1 1 calc R B .
C17 C 0.2345(3) 0.4850(3) 1.0631(2) 0.0410(10) Uani 1 1 d . B .
C18 C 0.2670(3) 0.5479(3) 0.9755(2) 0.0385(9) Uani 1 1 d . . .
C19 C 0.3634(3) 0.5281(3) 0.9092(2) 0.0384(9) Uani 1 1 d D B .
C41 C 0.1887(3) 0.6363(3) 0.9530(2) 0.0384(9) Uani 1 1 d . B .
C42 C 0.1620(3) 0.7201(3) 1.0053(2) 0.0416(10) Uani 1 1 d . . .
H42 H 0.1949 0.7222 1.0558 0.050 Uiso 1 1 calc R B .
C43 C 0.0882(3) 0.8008(3) 0.9854(3) 0.0462(10) Uani 1 1 d . B .
H43 H 0.0704 0.8577 1.0222 0.055 Uiso 1 1 calc R . .
C44 C 0.0400(3) 0.7987(3) 0.9114(3) 0.0406(10) Uani 1 1 d . . .
C45 C 0.0665(3) 0.7146(3) 0.8588(3) 0.0454(10) Uani 1 1 d . B .
H45 H 0.0342 0.7128 0.8079 0.054 Uiso 1 1 calc R . .
C46 C 0.1389(3) 0.6341(3) 0.8794(2) 0.0450(10) Uani 1 1 d . . .
H46 H 0.1553 0.5765 0.8435 0.054 Uiso 1 1 calc R B .
C47 C -0.0364(4) 0.8848(4) 0.8868(3) 0.0546(12) Uani 1 1 d . B .
C20 C 0.6529(13) 0.3881(5) 0.6930(5) 0.0471(11) Uani 0.68(3) 1 d PGD A 1
C21 C 0.6038(11) 0.3873(10) 0.6194(10) 0.0560(17) Uani 0.68(3) 1 d PGD A 1
H21 H 0.5286 0.3771 0.6326 0.067 Uiso 0.68(3) 1 calc PR A 1
C22 C 0.6646(14) 0.4013(12) 0.5266(8) 0.060(3) Uani 0.68(3) 1 d PG A 1
H22 H 0.6310 0.4007 0.4763 0.072 Uiso 0.68(3) 1 calc PR A 1
C23 C 0.7746(13) 0.4162(12) 0.5073(5) 0.057(3) Uani 0.68(3) 1 d PG A 1
C24 C 0.8237(10) 0.4170(17) 0.5809(9) 0.057(3) Uani 0.68(3) 1 d PG A 1
H24 H 0.8989 0.4272 0.5677 0.069 Uiso 0.68(3) 1 calc PR A 1
C25 C 0.7629(13) 0.4030(14) 0.6737(6) 0.0521(16) Uani 0.68(3) 1 d PGD A 1
H25 H 0.7965 0.4036 0.7240 0.062 Uiso 0.68(3) 1 calc PR A 1
C26 C 0.8388(16) 0.4289(9) 0.4038(9) 0.081(4) Uani 0.68(3) 1 d PD A 1
F1 F 0.8954(14) 0.3419(10) 0.3778(14) 0.094(2) Uani 0.68(3) 1 d PD A 1
F2 F 0.908(2) 0.5021(12) 0.3885(11) 0.173(7) Uani 0.68(3) 1 d PD A 1
F3 F 0.7757(15) 0.4570(12) 0.3450(6) 0.143(6) Uani 0.68(3) 1 d PD A 1
C20B C 0.650(3) 0.3916(13) 0.6959(11) 0.0471(11) Uani 0.32(3) 1 d PGD A 2
C21B C 0.584(2) 0.400(2) 0.633(2) 0.0560(17) Uani 0.32(3) 1 d PG A 2
H21B H 0.5079 0.3957 0.6569 0.067 Uiso 0.32(3) 1 calc PR A 2
C22B C 0.629(2) 0.413(3) 0.5368(19) 0.060(3) Uani 0.32(3) 1 d PG A 2
H22B H 0.5838 0.4188 0.4941 0.072 Uiso 0.32(3) 1 calc PR A 2
C23B C 0.740(2) 0.419(3) 0.5025(10) 0.057(3) Uani 0.32(3) 1 d PG A 2
C24B C 0.8064(19) 0.411(4) 0.5650(17) 0.057(3) Uani 0.32(3) 1 d PG A 2
H24B H 0.8824 0.4150 0.5415 0.069 Uiso 0.32(3) 1 calc PR A 2
C25B C 0.761(3) 0.397(3) 0.6616(15) 0.0521(16) Uani 0.32(3) 1 d PG A 2
H25B H 0.8066 0.3919 0.7043 0.062 Uiso 0.32(3) 1 calc PR A 2
C26B C 0.801(2) 0.4313(19) 0.4057(19) 0.081(4) Uani 0.32(3) 1 d PD A 2
F1B F 0.856(3) 0.516(2) 0.3785(16) 0.123(12) Uani 0.32(3) 1 d PD A 2
F2B F 0.737(2) 0.4348(19) 0.3477(14) 0.133(10) Uani 0.32(3) 1 d PD A 2
F3B F 0.871(3) 0.350(2) 0.387(3) 0.094(2) Uani 0.32(3) 1 d PD A 2
C27 C 0.6575(6) -0.0038(3) 1.0832(3) 0.0373(10) Uani 0.798(5) 1 d PG B 1
C28 C 0.6427(4) -0.0956(5) 1.0496(3) 0.0405(13) Uani 0.798(5) 1 d PG B 1
H28 H 0.5954 -0.0936 1.0091 0.049 Uiso 0.798(5) 1 calc PR B 1
C29 C 0.6970(4) -0.1903(3) 1.0753(3) 0.0456(14) Uani 0.798(5) 1 d PG B 1
H29 H 0.6868 -0.2530 1.0524 0.055 Uiso 0.798(5) 1 calc PR B 1
C30 C 0.7661(5) -0.1932(4) 1.1346(4) 0.0492(13) Uani 0.798(5) 1 d PGD B 1
C31 C 0.7810(7) -0.1014(5) 1.1682(5) 0.0540(16) Uani 0.798(5) 1 d PG B 1
H31 H 0.8283 -0.1034 1.2087 0.065 Uiso 0.798(5) 1 calc PR B 1
C32 C 0.7267(7) -0.0067(4) 1.1425(4) 0.0484(13) Uani 0.798(5) 1 d PG B 1
H32 H 0.7369 0.0560 1.1655 0.058 Uiso 0.798(5) 1 calc PR B 1
C33 C 0.8173(6) -0.2990(6) 1.1633(5) 0.0726(19) Uani 0.798(5) 1 d PD B 1
F4 F 0.8667(4) -0.3489(3) 1.0894(3) 0.0985(15) Uani 0.798(5) 1 d PD B 1
F5 F 0.8914(5) -0.2938(4) 1.2089(4) 0.119(3) Uani 0.798(5) 1 d PD B 1
F6 F 0.7446(4) -0.3645(3) 1.2165(4) 0.1014(19) Uani 0.798(5) 1 d PD B 1
C27B C 0.647(2) 0.0035(16) 1.0925(9) 0.0373(10) Uani 0.202(5) 1 d PGD B 2
C28B C 0.6157(16) -0.093(2) 1.0796(12) 0.0405(13) Uani 0.202(5) 1 d PGD B 2
H28B H 0.5562 -0.0949 1.0526 0.049 Uiso 0.202(5) 1 calc PR B 2
C29B C 0.6713(19) -0.1864(15) 1.1062(14) 0.0456(14) Uani 0.202(5) 1 d PG B 2
H29B H 0.6498 -0.2523 1.0973 0.055 Uiso 0.202(5) 1 calc PR B 2
C30B C 0.758(2) -0.1835(17) 1.1457(17) 0.0492(13) Uani 0.202(5) 1 d PGD B 2
C31B C 0.790(3) -0.087(2) 1.159(2) 0.0540(16) Uani 0.202(5) 1 d PG B 2
H31B H 0.8496 -0.0851 1.1856 0.065 Uiso 0.202(5) 1 calc PR B 2
C32B C 0.734(3) 0.0064(16) 1.132(2) 0.0484(13) Uani 0.202(5) 1 d PGD B 2
H32B H 0.7560 0.0723 1.1408 0.058 Uiso 0.202(5) 1 calc PR B 2
C33B C 0.8132(19) -0.280(2) 1.1864(15) 0.0726(19) Uani 0.202(5) 1 d PD B 2
F4B F 0.7810(15) -0.3035(12) 1.2793(11) 0.0985(15) Uani 0.202(5) 1 d PD B 2
F5B F 0.9186(15) -0.2725(18) 1.1717(16) 0.1014(19) Uani 0.202(5) 1 d PD B 2
F6B F 0.800(2) -0.3657(15) 1.1523(19) 0.119(3) Uani 0.202(5) 1 d PD B 2
F7 F 0.0627(12) 0.1068(13) 1.6685(8) 0.098(4) Uani 0.48(2) 1 d PD B 1
F8 F -0.0855(15) 0.1265(17) 1.6279(13) 0.120(7) Uani 0.48(2) 1 d PD B 1
F9 F -0.0261(17) 0.2540(14) 1.672(2) 0.073(4) Uani 0.48(2) 1 d PD B 1
C34 C 0.188(2) 0.250(3) 1.3371(19) 0.0442(16) Uani 0.48(2) 1 d PG B 1
C35 C 0.110(3) 0.176(3) 1.358(2) 0.055(4) Uani 0.48(2) 1 d PG B 1
H35 H 0.0988 0.1408 1.3092 0.066 Uiso 0.48(2) 1 calc PR B 1
C36 C 0.049(2) 0.153(3) 1.450(3) 0.063(4) Uani 0.48(2) 1 d PG B 1
H36 H -0.0039 0.1018 1.4641 0.075 Uiso 0.48(2) 1 calc PR B 1
C37 C 0.0656(18) 0.204(3) 1.521(2) 0.048(4) Uani 0.48(2) 1 d PG B 1
C38 C 0.1431(16) 0.279(2) 1.5003(19) 0.038(3) Uani 0.48(2) 1 d PG B 1
H38 H 0.1544 0.3137 1.5489 0.046 Uiso 0.48(2) 1 calc PR B 1
C39 C 0.2041(18) 0.302(2) 1.408(2) 0.044(3) Uani 0.48(2) 1 d PG B 1
H39 H 0.2571 0.3527 1.3940 0.053 Uiso 0.48(2) 1 calc PR B 1
C40 C 0.0034(16) 0.1730(14) 1.6225(16) 0.063(4) Uani 0.48(2) 1 d PD B 1
F7B F 0.0141(16) 0.0669(11) 1.6474(9) 0.116(6) Uani 0.52(2) 1 d PD B 2
F8B F -0.1210(13) 0.1491(13) 1.6086(11) 0.084(4) Uani 0.52(2) 1 d PD B 2
F9B F -0.022(2) 0.2267(16) 1.670(2) 0.096(5) Uani 0.52(2) 1 d PD B 2
C34B C 0.191(2) 0.243(3) 1.3408(18) 0.0442(16) Uani 0.52(2) 1 d PG B 2
C35B C 0.131(2) 0.155(3) 1.357(2) 0.055(4) Uani 0.52(2) 1 d PG B 2
H35B H 0.1381 0.1122 1.3078 0.066 Uiso 0.52(2) 1 calc PR B 2
C36B C 0.059(2) 0.130(2) 1.444(3) 0.063(4) Uani 0.52(2) 1 d PG B 2
H36B H 0.0178 0.0696 1.4543 0.075 Uiso 0.52(2) 1 calc PR B 2
C37B C 0.0485(17) 0.193(2) 1.515(2) 0.048(4) Uani 0.52(2) 1 d PG B 2
C38B C 0.1093(16) 0.281(2) 1.4990(17) 0.038(3) Uani 0.52(2) 1 d PG B 2
H38B H 0.1019 0.3235 1.5477 0.046 Uiso 0.52(2) 1 calc PR B 2
C39B C 0.1807(18) 0.306(2) 1.4120(19) 0.044(3) Uani 0.52(2) 1 d PG B 2
H39B H 0.2222 0.3661 1.4012 0.053 Uiso 0.52(2) 1 calc PR B 2
C40B C -0.0197(16) 0.1587(13) 1.6101(15) 0.063(4) Uani 0.52(2) 1 d PD B 2
F10 F -0.1270(2) 0.8507(2) 0.87536(19) 0.0731(8) Uani 1 1 d . . .
F11 F -0.0700(3) 0.9514(2) 0.9507(2) 0.0863(10) Uani 1 1 d . . .
F12 F 0.0046(3) 0.9417(2) 0.8048(2) 0.1018(12) Uani 1 1 d . . .
N1 N 0.4311(3) 0.4400(2) 0.91065(19) 0.0382(8) Uani 1 1 d . B .
N2 N 0.5705(3) 0.2488(2) 0.9439(2) 0.0394(8) Uani 1 1 d . B .
H2 H 0.5199 0.2861 0.9801 0.047 Uiso 1 1 calc R . .
N3 N 0.4296(3) 0.2108(2) 1.1318(2) 0.0416(8) Uani 1 1 d . B .
N4 N 0.2906(3) 0.4001(2) 1.09863(19) 0.0405(8) Uani 1 1 d . B .
H4 H 0.3545 0.3746 1.0694 0.049 Uiso 1 1 calc R . .
C1 C 0.4952(6) 0.5518(11) 0.7734(6) 0.0399(7) Uani 0.612(10) 1 d PDU B 1
N5 N 0.4065(6) 0.5976(7) 0.8250(7) 0.0399(7) Uani 0.612(10) 1 d PD B 1
N6 N 0.3651(11) 0.6998(9) 0.7980(8) 0.0526(10) Uani 0.612(10) 1 d PD B 1
H6A H 0.422(3) 0.742(3) 0.797(4) 0.063 Uiso 0.612(10) 1 d PD B 1
H6B H 0.376(5) 0.705(3) 0.7334(17) 0.063 Uiso 0.612(10) 1 d PD B 1
O1 O 0.5528(7) 0.5918(5) 0.6960(6) 0.0526(10) Uani 0.612(10) 1 d PD B 1
C1B C 0.3936(13) 0.6008(13) 0.8227(13) 0.0399(7) Uani 0.388(10) 1 d PD B 2
N5B N 0.4901(7) 0.5529(13) 0.7770(8) 0.0399(7) Uani 0.388(10) 1 d PD B 2
N6B N 0.5636(14) 0.6131(12) 0.7053(12) 0.0526(10) Uani 0.388(10) 1 d PD B 2
H6C H 0.563(6) 0.676(3) 0.731(4) 0.063 Uiso 0.388(10) 1 d PD B 2
H6D H 0.523(5) 0.641(6) 0.662(4) 0.063 Uiso 0.388(10) 1 d PD B 2
O1B O 0.3679(15) 0.6993(12) 0.8126(10) 0.0526(10) Uani 0.388(10) 1 d PD B 2
O2 O 0.5149(9) 0.7579(9) 0.5587(6) 0.121(3) Uani 0.612(10) 1 d PDU B 1
H2A H 0.5460 0.7122 0.5929 0.182 Uiso 0.612(10) 1 d PR B 1
C48 C 0.5918(14) 0.7712(14) 0.4759(8) 0.123(4) Uani 0.612(10) 1 d PDU B 1
H48A H 0.6216 0.7007 0.4584 0.148 Uiso 0.612(10) 1 calc PR B 1
H48B H 0.6517 0.8082 0.4856 0.148 Uiso 0.612(10) 1 calc PR B 1
C49 C 0.5513(11) 0.8321(11) 0.3963(7) 0.116(4) Uani 0.612(10) 1 d PDU B 1
H49A H 0.5425 0.9074 0.4038 0.173 Uiso 0.612(10) 1 calc PR B 1
H49B H 0.4814 0.8070 0.3962 0.173 Uiso 0.612(10) 1 calc PR B 1
H49C H 0.6034 0.8219 0.3365 0.173 Uiso 0.612(10) 1 calc PR B 1
O3 O 0.3572(10) 0.8406(12) 0.6423(8) 0.167(4) Uani 0.612(10) 1 d PDU B 1
H3 H 0.3789 0.7894 0.6115 0.250 Uiso 0.612(10) 1 d PR B 1
C50 C 0.2588(16) 0.8789(18) 0.6311(10) 0.133(4) Uani 0.612(10) 1 d PDU B 1
H50A H 0.2250 0.9239 0.6810 0.159 Uiso 0.612(10) 1 calc PR B 1
H50B H 0.2124 0.8192 0.6388 0.159 Uiso 0.612(10) 1 calc PR B 1
C51 C 0.2634(16) 0.9402(16) 0.5401(9) 0.151(5) Uani 0.612(10) 1 d PDU B 1
H51A H 0.3357 0.9666 0.5143 0.226 Uiso 0.612(10) 1 calc PR B 1
H51B H 0.2094 1.0000 0.5470 0.226 Uiso 0.612(10) 1 calc PR B 1
H51C H 0.2482 0.8954 0.4973 0.226 Uiso 0.612(10) 1 calc PR B 1
O2B O 0.5250(15) 0.7072(14) 0.5179(11) 0.122(5) Uani 0.388(10) 1 d PDU B 2
H2B H 0.4654 0.7357 0.5493 0.182 Uiso 0.388(10) 1 d PR B 2
C48B C 0.603(2) 0.7533(18) 0.4444(18) 0.131(5) Uani 0.388(10) 1 d PDU B 2
H48C H 0.6028 0.7223 0.3870 0.157 Uiso 0.388(10) 1 calc PR B 2
H48D H 0.6744 0.7327 0.4586 0.157 Uiso 0.388(10) 1 calc PR B 2
C49B C 0.595(2) 0.8682(17) 0.4222(19) 0.160(7) Uani 0.388(10) 1 d PDU B 2
H49D H 0.5224 0.8911 0.4132 0.240 Uiso 0.388(10) 1 calc PR B 2
H49E H 0.6492 0.8899 0.3642 0.240 Uiso 0.388(10) 1 calc PR B 2
H49F H 0.6070 0.9007 0.4742 0.240 Uiso 0.388(10) 1 calc PR B 2
O3B O 0.3097(14) 0.7884(13) 0.6292(10) 0.125(4) Uani 0.388(10) 1 d PDU B 2
H3B H 0.3185 0.7745 0.6856 0.188 Uiso 0.388(10) 1 d PR B 2
C50B C 0.258(3) 0.883(3) 0.6017(17) 0.140(4) Uani 0.388(10) 1 d PDU B 2
H50C H 0.2827 0.9405 0.6280 0.168 Uiso 0.388(10) 1 calc PR B 2
H50D H 0.1793 0.8795 0.6280 0.168 Uiso 0.388(10) 1 calc PR B 2
C51B C 0.280(3) 0.908(3) 0.5012(16) 0.160(8) Uani 0.388(10) 1 d PDU B 2
H51D H 0.2365 0.9716 0.4849 0.240 Uiso 0.388(10) 1 calc PR B 2
H51E H 0.2609 0.8485 0.4745 0.240 Uiso 0.388(10) 1 calc PR B 2
H51F H 0.3568 0.9193 0.4755 0.240 Uiso 0.388(10) 1 calc PR B 2
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
C2 0.051(3) 0.041(2) 0.0248(19) 0.0052(16) -0.0068(18) -0.0051(19)
C3 0.046(2) 0.041(2) 0.0327(19) -0.0011(17) -0.0079(18) -0.0033(19)
C4 0.042(2) 0.046(2) 0.0271(19) -0.0012(17) -0.0062(17) -0.0047(19)
C5 0.050(3) 0.048(2) 0.035(2) -0.0055(18) -0.0020(18) 0.005(2)
C6 0.044(3) 0.048(2) 0.037(2) -0.0018(18) -0.0070(18) 0.004(2)
C7 0.038(2) 0.040(2) 0.038(2) 0.0005(17) -0.0123(18) -0.0038(18)
C8 0.043(2) 0.043(2) 0.037(2) -0.0003(17) -0.0125(18) -0.0011(19)
C9 0.055(3) 0.038(2) 0.035(2) 0.0008(17) -0.0152(19) 0.007(2)
C10 0.064(3) 0.049(3) 0.037(2) 0.0096(19) -0.003(2) 0.012(2)
C11 0.076(3) 0.048(3) 0.029(2) 0.0096(18) -0.004(2) 0.013(2)
C12 0.063(3) 0.038(2) 0.029(2) 0.0002(16) -0.0073(19) 0.006(2)
C13 0.062(3) 0.042(2) 0.0245(18) 0.0018(16) -0.0064(18) 0.001(2)
C14 0.057(3) 0.040(2) 0.0283(19) -0.0034(16) -0.0058(18) 0.003(2)
C15 0.056(3) 0.045(2) 0.0294(19) 0.0006(17) -0.0057(18) 0.006(2)
C16 0.057(3) 0.043(2) 0.037(2) -0.0001(18) -0.010(2) 0.011(2)
C17 0.055(3) 0.038(2) 0.0284(19) -0.0040(16) -0.0103(18) 0.0041(19)
C18 0.051(3) 0.033(2) 0.0310(19) -0.0013(16) -0.0116(18) 0.0006(18)
C19 0.055(3) 0.033(2) 0.0258(18) 0.0010(15) -0.0102(18) -0.0017(19)
C41 0.050(2) 0.031(2) 0.0288(19) 0.0023(15) -0.0053(17) 0.0006(18)
C42 0.055(3) 0.037(2) 0.033(2) -0.0014(17) -0.0144(18) 0.002(2)
C43 0.062(3) 0.039(2) 0.036(2) -0.0082(17) -0.011(2) 0.004(2)
C44 0.049(3) 0.033(2) 0.037(2) 0.0020(16) -0.0105(18) 0.0030(19)
C45 0.061(3) 0.043(2) 0.034(2) 0.0015(17) -0.0203(19) 0.003(2)
C46 0.063(3) 0.041(2) 0.031(2) -0.0061(17) -0.0133(19) 0.004(2)
C47 0.066(3) 0.050(3) 0.048(3) -0.005(2) -0.019(2) 0.006(2)
C20 0.065(3) 0.037(2) 0.033(2) -0.0006(17) -0.005(2) 0.006(2)
C21 0.073(5) 0.061(4) 0.030(5) -0.013(3) -0.005(3) 0.005(4)
C22 0.076(9) 0.063(5) 0.029(3) -0.012(3) 0.000(5) 0.026(6)
C23 0.081(8) 0.042(3) 0.032(3) 0.004(2) 0.005(4) 0.019(6)
C24 0.074(5) 0.047(4) 0.036(5) 0.004(5) 0.006(3) 0.002(4)
C25 0.062(3) 0.051(3) 0.034(3) -0.002(3) 0.003(3) 0.003(2)
C26 0.118(11) 0.049(4) 0.045(3) 0.005(3) 0.022(6) 0.022(6)
F1 0.124(7) 0.081(3) 0.043(4) -0.009(2) 0.034(5) 0.023(3)
F2 0.268(17) 0.111(8) 0.082(9) -0.040(6) 0.109(8) -0.088(9)
F3 0.186(11) 0.139(9) 0.043(5) 0.034(5) 0.019(5) 0.086(9)
C20B 0.065(3) 0.037(2) 0.033(2) -0.0006(17) -0.005(2) 0.006(2)
C21B 0.073(5) 0.061(4) 0.030(5) -0.013(3) -0.005(3) 0.005(4)
C22B 0.076(9) 0.063(5) 0.029(3) -0.012(3) 0.000(5) 0.026(6)
C23B 0.081(8) 0.042(3) 0.032(3) 0.004(2) 0.005(4) 0.019(6)
C24B 0.074(5) 0.047(4) 0.036(5) 0.004(5) 0.006(3) 0.002(4)
C25B 0.062(3) 0.051(3) 0.034(3) -0.002(3) 0.003(3) 0.003(2)
C26B 0.118(11) 0.049(4) 0.045(3) 0.005(3) 0.022(6) 0.022(6)
F1B 0.26(3) 0.070(10) 0.027(8) 0.020(7) -0.006(15) -0.074(16)
F2B 0.21(2) 0.176(18) 0.024(8) -0.012(8) -0.023(10) -0.094(19)
F3B 0.124(7) 0.081(3) 0.043(4) -0.009(2) 0.034(5) 0.023(3)
C27 0.041(3) 0.035(2) 0.030(2) 0.0040(17) -0.0060(18) 0.0050(19)
C28 0.038(3) 0.046(3) 0.034(3) -0.004(3) -0.006(3) 0.004(3)
C29 0.050(4) 0.038(2) 0.046(4) -0.009(3) -0.006(3) 0.002(2)
C30 0.051(3) 0.035(3) 0.058(3) 0.007(2) -0.017(2) 0.007(2)
C31 0.060(3) 0.050(4) 0.054(3) 0.009(3) -0.028(3) 0.002(3)
C32 0.058(3) 0.047(3) 0.042(3) 0.001(2) -0.020(3) -0.004(2)
C33 0.090(5) 0.048(4) 0.088(5) 0.000(4) -0.041(4) -0.006(3)
F4 0.104(3) 0.049(2) 0.129(4) 0.001(2) -0.022(3) 0.027(2)
F5 0.150(6) 0.059(3) 0.188(7) 0.007(3) -0.134(6) 0.018(3)
F6 0.103(3) 0.062(3) 0.115(4) 0.047(3) -0.020(3) 0.000(2)
C27B 0.041(3) 0.035(2) 0.030(2) 0.0040(17) -0.0060(18) 0.0050(19)
C28B 0.038(3) 0.046(3) 0.034(3) -0.004(3) -0.006(3) 0.004(3)
C29B 0.050(4) 0.038(2) 0.046(4) -0.009(3) -0.006(3) 0.002(2)
C30B 0.051(3) 0.035(3) 0.058(3) 0.007(2) -0.017(2) 0.007(2)
C31B 0.060(3) 0.050(4) 0.054(3) 0.009(3) -0.028(3) 0.002(3)
C32B 0.058(3) 0.047(3) 0.042(3) 0.001(2) -0.020(3) -0.004(2)
C33B 0.090(5) 0.048(4) 0.088(5) 0.000(4) -0.041(4) -0.006(3)
F4B 0.104(3) 0.049(2) 0.129(4) 0.001(2) -0.022(3) 0.027(2)
F5B 0.103(3) 0.062(3) 0.115(4) 0.047(3) -0.020(3) 0.000(2)
F6B 0.150(6) 0.059(3) 0.188(7) 0.007(3) -0.134(6) 0.018(3)
F7 0.098(8) 0.123(9) 0.051(4) 0.041(5) -0.014(4) 0.001(6)
F8 0.082(11) 0.214(18) 0.061(7) 0.000(8) 0.000(7) -0.071(11)
F9 0.065(7) 0.110(8) 0.032(6) -0.001(6) 0.000(5) 0.010(7)
C34 0.055(3) 0.036(4) 0.034(2) 0.005(2) -0.007(2) 0.011(2)
C35 0.083(10) 0.043(11) 0.032(2) 0.002(5) -0.007(5) 0.007(7)
C36 0.093(6) 0.044(10) 0.043(5) 0.006(6) -0.005(4) -0.015(6)
C37 0.055(6) 0.052(6) 0.030(3) 0.006(4) -0.005(4) 0.000(5)
C38 0.016(10) 0.061(3) 0.034(2) -0.007(2) -0.006(7) 0.018(8)
C39 0.042(8) 0.047(3) 0.035(3) -0.006(2) 0.001(5) 0.012(5)
C40 0.078(8) 0.068(5) 0.038(5) 0.002(4) -0.010(5) 0.000(5)
F7B 0.142(12) 0.097(8) 0.056(6) 0.046(5) 0.028(6) 0.031(7)
F8B 0.074(8) 0.118(7) 0.052(6) -0.026(5) 0.017(5) -0.025(6)
F9B 0.128(13) 0.114(10) 0.037(6) -0.020(8) 0.008(7) -0.027(8)
C34B 0.055(3) 0.036(4) 0.034(2) 0.005(2) -0.007(2) 0.011(2)
C35B 0.083(10) 0.043(11) 0.032(2) 0.002(5) -0.007(5) 0.007(7)
C36B 0.093(6) 0.044(10) 0.043(5) 0.006(6) -0.005(4) -0.015(6)
C37B 0.055(6) 0.052(6) 0.030(3) 0.006(4) -0.005(4) 0.000(5)
C38B 0.016(10) 0.061(3) 0.034(2) -0.007(2) -0.006(7) 0.018(8)
C39B 0.042(8) 0.047(3) 0.035(3) -0.006(2) 0.001(5) 0.012(5)
C40B 0.078(8) 0.068(5) 0.038(5) 0.002(4) -0.010(5) 0.000(5)
F10 0.069(2) 0.0792(19) 0.0764(18) -0.0163(14) -0.0317(15) 0.0189(16)
F11 0.110(2) 0.0635(18) 0.100(2) -0.0366(16) -0.0562(19) 0.0415(17)
F12 0.090(2) 0.087(2) 0.094(2) 0.0522(18) -0.0061(18) 0.0220(18)
N1 0.050(2) 0.0337(18) 0.0282(16) -0.0003(13) -0.0094(15) 0.0021(16)
N2 0.044(2) 0.0388(18) 0.0319(16) 0.0007(13) -0.0079(14) 0.0030(15)
N3 0.051(2) 0.0388(18) 0.0300(16) 0.0003(13) -0.0067(15) 0.0046(16)
N4 0.052(2) 0.0353(18) 0.0271(16) 0.0012(13) -0.0050(14) 0.0106(16)
C1 0.0427(11) 0.0377(10) 0.0365(9) 0.0013(7) -0.0087(8) -0.0009(8)
N5 0.0427(11) 0.0377(10) 0.0365(9) 0.0013(7) -0.0087(8) -0.0009(8)
N6 0.066(2) 0.0417(18) 0.040(2) 0.0050(16) -0.0021(16) -0.0012(14)
O1 0.066(2) 0.0417(18) 0.040(2) 0.0050(16) -0.0021(16) -0.0012(14)
C1B 0.0427(11) 0.0377(10) 0.0365(9) 0.0013(7) -0.0087(8) -0.0009(8)
N5B 0.0427(11) 0.0377(10) 0.0365(9) 0.0013(7) -0.0087(8) -0.0009(8)
N6B 0.066(2) 0.0417(18) 0.040(2) 0.0050(16) -0.0021(16) -0.0012(14)
O1B 0.066(2) 0.0417(18) 0.040(2) 0.0050(16) -0.0021(16) -0.0012(14)
O2 0.128(6) 0.151(8) 0.064(5) 0.028(5) -0.022(5) 0.020(6)
C48 0.118(6) 0.158(8) 0.077(7) 0.029(6) -0.023(6) -0.004(6)
C49 0.130(9) 0.136(9) 0.077(6) 0.036(6) -0.038(6) -0.026(7)
O3 0.161(8) 0.232(10) 0.097(5) 0.062(6) -0.053(6) -0.032(7)
C50 0.130(7) 0.168(8) 0.082(7) 0.016(7) -0.012(7) -0.009(6)
C51 0.115(9) 0.237(12) 0.075(8) 0.026(8) -0.016(8) 0.022(8)
O2B 0.137(9) 0.156(11) 0.069(8) 0.024(7) -0.044(7) -0.003(8)
C48B 0.128(8) 0.165(9) 0.096(9) 0.013(8) -0.035(8) -0.016(8)
C49B 0.165(12) 0.177(10) 0.112(11) 0.042(10) -0.017(10) -0.024(11)
O3B 0.126(8) 0.163(9) 0.080(6) 0.043(7) -0.039(6) -0.024(7)
C50B 0.128(7) 0.176(9) 0.093(8) 0.037(8) -0.018(7) -0.006(6)
C51B 0.134(13) 0.210(15) 0.106(11) 0.047(12) -0.032(13) 0.036(12)
_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
C2 N1 1.362(5) . ?
C2 C3 1.400(5) . ?
C2 C1 1.454(16) . ?
C2 N5B 1.455(18) . ?
C3 C4 1.411(5) . ?
C3 C20B 1.473(14) . ?
C3 C20 1.518(7) . ?
C4 N2 1.370(4) . ?
C4 C5 1.414(5) . ?
C5 C6 1.359(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.412(5) . ?
C6 H6 0.9500 . ?
C7 N2 1.375(5) . ?
C7 C8 1.404(5) . ?
C8 C9 1.396(5) . ?
C8 C27B 1.419(16) . ?
C8 C27 1.526(5) . ?
C9 N3 1.366(5) . ?
C9 C10 1.457(5) . ?
C10 C11 1.339(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.459(5) . ?
C11 H11 0.9500 . ?
C12 N3 1.362(5) . ?
C12 C13 1.395(6) . ?
C13 C14 1.402(5) . ?
C13 C34 1.48(3) . ?
C13 C34B 1.51(3) . ?
C14 N4 1.376(5) . ?
C14 C15 1.414(5) . ?
C15 C16 1.364(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.436(6) . ?
C16 H16 0.9500 . ?
C17 N4 1.358(5) . ?
C17 C18 1.406(5) . ?
C18 C19 1.396(5) . ?
C18 C41 1.495(5) . ?
C19 N1 1.355(5) . ?
C19 N5 1.436(11) . ?
C19 C1B 1.45(2) . ?
C41 C42 1.382(5) . ?
C41 C46 1.398(5) . ?
C42 C43 1.382(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.390(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.388(5) . ?
C44 C47 1.469(6) . ?
C45 C46 1.370(5) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 F12 1.327(5) . ?
C47 F11 1.330(5) . ?
C47 F10 1.336(5) . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 C22 1.3900 . ?
C21 H21 0.9500 . ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 C24 1.3900 . ?
C23 C26 1.535(13) . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 F2 1.311(10) . ?
C26 F3 1.320(10) . ?
C26 F1 1.321(8) . ?
C20B C21B 1.3900 . ?
C20B C25B 1.3900 . ?
C21B C22B 1.3900 . ?
C21B H21B 0.9500 . ?
C22B C23B 1.3900 . ?
C22B H22B 0.9500 . ?
C23B C24B 1.3900 . ?
C23B C26B 1.44(3) . ?
C24B C25B 1.3900 . ?
C24B H24B 0.9500 . ?
C25B H25B 0.9500 . ?
C26B F1B 1.313(15) . ?
C26B F2B 1.318(15) . ?
C26B F3B 1.323(15) . ?
C27 C28 1.3900 . ?
C27 C32 1.3900 . ?
C28 C29 1.3900 . ?
C28 H28 0.9500 . ?
C29 C30 1.3900 . ?
C29 H29 0.9500 . ?
C30 C31 1.3900 . ?
C30 C33 1.498(8) . ?
C31 C32 1.3900 . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 F5 1.307(7) . ?
C33 F6 1.331(7) . ?
C33 F4 1.334(8) . ?
C27B C28B 1.3900 . ?
C27B C32B 1.3900 . ?
C28B C29B 1.3900 . ?
C28B H28B 0.9500 . ?
C29B C30B 1.3900 . ?
C29B H29B 0.9500 . ?
C30B C31B 1.3900 . ?
C30B C33B 1.48(3) . ?
C31B C32B 1.3900 . ?
C31B H31B 0.9500 . ?
C32B H32B 0.9500 . ?
C33B F5B 1.321(16) . ?
C33B F6B 1.323(16) . ?
C33B F4B 1.328(16) . ?
F7 C40 1.313(13) . ?
F8 C40 1.315(13) . ?
F9 C40 1.329(13) . ?
C34 C35 1.3900 . ?
C34 C39 1.3900 . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 C37 1.3900 . ?
C36 H36 0.9500 . ?
C37 C38 1.3900 . ?
C37 C40 1.52(4) . ?
C38 C39 1.3900 . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
F7B C40B 1.305(12) . ?
F8B C40B 1.319(13) . ?
F9B C40B 1.327(12) . ?
C34B C35B 1.3900 . ?
C34B C39B 1.3900 . ?
C35B C36B 1.3900 . ?
C35B H35B 0.9500 . ?
C36B C37B 1.3900 . ?
C36B H36B 0.9500 . ?
C37B C38B 1.3900 . ?
C37B C40B 1.48(3) . ?
C38B C39B 1.3900 . ?
C38B H38B 0.9500 . ?
C39B H39B 0.9500 . ?
N2 H2 0.8800 . ?
N4 H4 0.8800 . ?
C1 O1 1.258(10) . ?
C1 N5 1.334(8) . ?
N5 N6 1.405(10) . ?
N6 H6A 0.94(2) . ?
N6 H6B 0.923(19) . ?
O1 H6D 0.86(4) . ?
C1B O1B 1.270(13) . ?
C1B N5B 1.382(12) . ?
N5B N6B 1.412(13) . ?
N6B H6C 0.93(2) . ?
N6B H6D 0.93(2) . ?
O1B H6A 0.89(3) . ?
O2 C48 1.362(11) . ?
O2 H2A 0.8522 . ?
C48 C49 1.490(14) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
O3 C50 1.348(15) . ?
O3 H3 0.8400 . ?
C50 C51 1.443(13) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
O2B C48B 1.379(16) . ?
O2B H2B 0.8639 . ?
C48B C49B 1.460(17) . ?
C48B H48C 0.9900 . ?
C48B H48D 0.9900 . ?
C49B H49D 0.9800 . ?
C49B H49E 0.9800 . ?
C49B H49F 0.9800 . ?
O3B C50B 1.379(17) . ?
O3B H3B 0.8595 . ?
C50B C51B 1.433(16) . ?
C50B H50C 0.9900 . ?
C50B H50D 0.9900 . ?
C51B H51D 0.9800 . ?
C51B H51E 0.9800 . ?
C51B H51F 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
N1 C2 C3 127.0(3) . . ?
N1 C2 C1 110.5(4) . . ?
C3 C2 C1 122.5(4) . . ?
N1 C2 N5B 107.6(5) . . ?
C3 C2 N5B 125.4(5) . . ?
C2 C3 C4 124.7(3) . . ?
C2 C3 C20B 117.1(10) . . ?
C4 C3 C20B 118.1(9) . . ?
C2 C3 C20 118.9(4) . . ?
C4 C3 C20 116.3(4) . . ?
N2 C4 C3 126.6(3) . . ?
N2 C4 C5 106.6(3) . . ?
C3 C4 C5 126.8(3) . . ?
C6 C5 C4 108.4(3) . . ?
C6 C5 H5 125.8 . . ?
C4 C5 H5 125.8 . . ?
C5 C6 C7 108.3(3) . . ?
C5 C6 H6 125.9 . . ?
C7 C6 H6 125.9 . . ?
N2 C7 C8 125.3(3) . . ?
N2 C7 C6 106.7(3) . . ?
C8 C7 C6 128.0(3) . . ?
C9 C8 C7 125.4(3) . . ?
C9 C8 C27B 112.3(4) . . ?
C7 C8 C27B 122.2(4) . . ?
C9 C8 C27 118.4(3) . . ?
C7 C8 C27 116.1(3) . . ?
N3 C9 C8 126.3(3) . . ?
N3 C9 C10 110.5(3) . . ?
C8 C9 C10 123.1(3) . . ?
C11 C10 C9 106.8(3) . . ?
C11 C10 H10 126.6 . . ?
C9 C10 H10 126.6 . . ?
C10 C11 C12 106.4(3) . . ?
C10 C11 H11 126.8 . . ?
C12 C11 H11 126.8 . . ?
N3 C12 C13 126.4(3) . . ?
N3 C12 C11 110.8(3) . . ?
C13 C12 C11 122.8(3) . . ?
C12 C13 C14 125.5(3) . . ?
C12 C13 C34 121.3(13) . . ?
C14 C13 C34 113.2(13) . . ?
C12 C13 C34B 117.1(11) . . ?
C14 C13 C34B 117.3(12) . . ?
N4 C14 C13 126.2(4) . . ?
N4 C14 C15 106.8(3) . . ?
C13 C14 C15 126.9(4) . . ?
C16 C15 C14 108.4(3) . . ?
C16 C15 H15 125.8 . . ?
C14 C15 H15 125.8 . . ?
C15 C16 C17 107.6(3) . . ?
C15 C16 H16 126.2 . . ?
C17 C16 H16 126.2 . . ?
N4 C17 C18 127.2(4) . . ?
N4 C17 C16 106.8(3) . . ?
C18 C17 C16 126.0(3) . . ?
C19 C18 C17 123.5(3) . . ?
C19 C18 C41 120.1(3) . . ?
C17 C18 C41 116.3(3) . . ?
N1 C19 C18 126.8(3) . . ?
N1 C19 N5 107.9(4) . . ?
C18 C19 N5 125.3(4) . . ?
N1 C19 C1B 113.0(6) . . ?
C18 C19 C1B 119.8(6) . . ?
C42 C41 C46 118.7(3) . . ?
C42 C41 C18 121.1(3) . . ?
C46 C41 C18 120.2(3) . . ?
C43 C42 C41 121.1(4) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C42 C43 C44 119.9(4) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
C45 C44 C43 119.2(3) . . ?
C45 C44 C47 119.6(4) . . ?
C43 C44 C47 121.2(4) . . ?
C46 C45 C44 120.7(4) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C45 C46 C41 120.5(4) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
F12 C47 F11 107.5(4) . . ?
F12 C47 F10 104.1(4) . . ?
F11 C47 F10 104.8(4) . . ?
F12 C47 C44 112.1(4) . . ?
F11 C47 C44 114.3(4) . . ?
F10 C47 C44 113.3(4) . . ?
C21 C20 C25 120.0 . . ?
C21 C20 C3 122.0(11) . . ?
C25 C20 C3 118.0(11) . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 C26 118.1(8) . . ?
C24 C23 C26 121.9(8) . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.0 . . ?
C24 C25 H25 120.0 . . ?
C20 C25 H25 120.0 . . ?
F2 C26 F3 107.2(9) . . ?
F2 C26 F1 106.4(9) . . ?
F3 C26 F1 106.6(9) . . ?
F2 C26 C23 110.6(12) . . ?
F3 C26 C23 112.3(9) . . ?
F1 C26 C23 113.4(11) . . ?
C21B C20B C25B 120.0 . . ?
C21B C20B C3 113(3) . . ?
C25B C20B C3 127(3) . . ?
C22B C21B C20B 120.0 . . ?
C22B C21B H21B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C21B C22B C23B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
C22B C23B C24B 120.0 . . ?
C22B C23B C26B 128(2) . . ?
C24B C23B C26B 112(2) . . ?
C25B C24B C23B 120.0 . . ?
C25B C24B H24B 120.0 . . ?
C23B C24B H24B 120.0 . . ?
C24B C25B C20B 120.0 . . ?
C24B C25B H25B 120.0 . . ?
C20B C25B H25B 120.0 . . ?
F1B C26B F2B 106.2(15) . . ?
F1B C26B F3B 106.6(16) . . ?
F2B C26B F3B 105.5(15) . . ?
F1B C26B C23B 115(3) . . ?
F2B C26B C23B 111(2) . . ?
F3B C26B C23B 111(3) . . ?
C28 C27 C32 120.0 . . ?
C28 C27 C8 120.6(5) . . ?
C32 C27 C8 119.0(5) . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 120.0 . . ?
C29 C30 C33 117.0(5) . . ?
C31 C30 C33 122.9(5) . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C27 120.0 . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
F5 C33 F6 108.1(6) . . ?
F5 C33 F4 105.4(6) . . ?
F6 C33 F4 105.0(6) . . ?
F5 C33 C30 113.4(6) . . ?
F6 C33 C30 112.1(6) . . ?
F4 C33 C30 112.3(6) . . ?
C28B C27B C32B 120.0 . . ?
C28B C27B C8 119(2) . . ?
C32B C27B C8 121(2) . . ?
C27B C28B C29B 120.0 . . ?
C27B C28B H28B 120.0 . . ?
C29B C28B H28B 120.0 . . ?
C30B C29B C28B 120.0 . . ?
C30B C29B H29B 120.0 . . ?
C28B C29B H29B 120.0 . . ?
C29B C30B C31B 120.0 . . ?
C29B C30B C33B 123.2(16) . . ?
C31B C30B C33B 116.4(17) . . ?
C32B C31B C30B 120.0 . . ?
C32B C31B H31B 120.0 . . ?
C30B C31B H31B 120.0 . . ?
C31B C32B C27B 120.0 . . ?
C31B C32B H32B 120.0 . . ?
C27B C32B H32B 120.0 . . ?
F5B C33B F6B 106.8(18) . . ?
F5B C33B F4B 103.3(16) . . ?
F6B C33B F4B 104.7(17) . . ?
F5B C33B C30B 112.9(16) . . ?
F6B C33B C30B 112.7(16) . . ?
F4B C33B C30B 115.4(16) . . ?
C35 C34 C39 120.0 . . ?
C35 C34 C13 123(2) . . ?
C39 C34 C13 117(2) . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 C36 120.0 . . ?
C38 C37 C40 120.5(19) . . ?
C36 C37 C40 119(2) . . ?
C37 C38 C39 120.0 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C39 C34 120.0 . . ?
C38 C39 H39 120.0 . . ?
C34 C39 H39 120.0 . . ?
F7 C40 F8 107.1(13) . . ?
F7 C40 F9 105.7(12) . . ?
F8 C40 F9 106.5(13) . . ?
F7 C40 C37 110.8(17) . . ?
F8 C40 C37 112.5(19) . . ?
F9 C40 C37 114(2) . . ?
C35B C34B C39B 120.0 . . ?
C35B C34B C13 118(2) . . ?
C39B C34B C13 122(2) . . ?
C34B C35B C36B 120.0 . . ?
C34B C35B H35B 120.0 . . ?
C36B C35B H35B 120.0 . . ?
C37B C36B C35B 120.0 . . ?
C37B C36B H36B 120.0 . . ?
C35B C36B H36B 120.0 . . ?
C38B C37B C36B 120.0 . . ?
C38B C37B C40B 120.4(18) . . ?
C36B C37B C40B 119.3(18) . . ?
C37B C38B C39B 120.0 . . ?
C37B C38B H38B 120.0 . . ?
C39B C38B H38B 120.0 . . ?
C38B C39B C34B 120.0 . . ?
C38B C39B H39B 120.0 . . ?
C34B C39B H39B 120.0 . . ?
F7B C40B F8B 106.1(11) . . ?
F7B C40B F9B 106.8(12) . . ?
F8B C40B F9B 106.7(12) . . ?
F7B C40B C37B 112.4(16) . . ?
F8B C40B C37B 112.1(16) . . ?
F9B C40B C37B 112(2) . . ?
C19 N1 C2 107.0(3) . . ?
C4 N2 C7 110.0(3) . . ?
C4 N2 H2 125.0 . . ?
C7 N2 H2 125.0 . . ?
C12 N3 C9 105.5(3) . . ?
C17 N4 C14 110.4(3) . . ?
C17 N4 H4 124.8 . . ?
C14 N4 H4 124.8 . . ?
O1 C1 N5 126.3(16) . . ?
O1 C1 C2 129.7(9) . . ?
N5 C1 C2 104.1(10) . . ?
C1 N5 N6 122.9(15) . . ?
C1 N5 C19 110.2(10) . . ?
N6 N5 C19 126.9(9) . . ?
N5 N6 H6A 103(3) . . ?
N5 N6 H6B 105(3) . . ?
H6A N6 H6B 95(2) . . ?
C1 O1 H2A 139.9 . . ?
C1 O1 H6D 118(4) . . ?
O1B C1B N5B 125(2) . . ?
O1B C1B C19 126.1(15) . . ?
N5B C1B C19 101.9(14) . . ?
C1B N5B N6B 120(2) . . ?
C1B N5B C2 109.9(14) . . ?
N6B N5B C2 129.0(11) . . ?
N5B N6B H6C 103(3) . . ?
N5B N6B H6D 104(3) . . ?
H6C N6B H6D 96(3) . . ?
C1B O1B H3B 120.2 . . ?
C48 O2 H2A 102.6 . . ?
C48 O2 H2B 108.3 . . ?
O2 C48 C49 113.9(11) . . ?
O2 C48 H48A 108.8 . . ?
C49 C48 H48A 108.8 . . ?
O2 C48 H48B 108.8 . . ?
C49 C48 H48B 108.8 . . ?
H48A C48 H48B 107.7 . . ?
C50 O3 H3 109.9 . . ?
C50 O3 H3B 87.3 . . ?
O3 C50 C51 112.7(13) . . ?
O3 C50 H50A 109.0 . . ?
C51 C50 H50A 109.0 . . ?
O3 C50 H50B 109.0 . . ?
C51 C50 H50B 109.0 . . ?
H50A C50 H50B 107.8 . . ?
C48B O2B H2A 110.2 . . ?
C48B O2B H2B 129.1 . . ?
O2B C48B C49B 117.6(17) . . ?
O2B C48B H48C 107.9 . . ?
C49B C48B H48C 107.9 . . ?
O2B C48B H48D 107.9 . . ?
C49B C48B H48D 107.9 . . ?
H48C C48B H48D 107.2 . . ?
C48B C49B H49D 109.5 . . ?
C48B C49B H49E 109.5 . . ?
H49D C49B H49E 109.5 . . ?
C48B C49B H49F 109.5 . . ?
H49D C49B H49F 109.5 . . ?
H49E C49B H49F 109.5 . . ?
C50B O3B H2B 121.7 . . ?
C50B O3B H3 112.5 . . ?
C50B O3B H3B 120.0 . . ?
O3B C50B C51B 112.2(17) . . ?
O3B C50B H50C 109.2 . . ?
C51B C50B H50C 109.2 . . ?
O3B C50B H50D 109.2 . . ?
C51B C50B H50D 109.2 . . ?
H50C C50B H50D 107.9 . . ?
C50B C51B H51D 109.5 . . ?
C50B C51B H51E 109.5 . . ?
H51D C51B H51E 109.5 . . ?
C50B C51B H51F 109.5 . . ?
H51D C51B H51F 109.5 . . ?
H51E C51B H51F 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
N1 C2 C3 C4 -8.8(6) . . . . ?
C1 C2 C3 C4 171.6(4) . . . . ?
N5B C2 C3 C4 172.0(4) . . . . ?
N1 C2 C3 C20B 167.7(18) . . . . ?
C1 C2 C3 C20B -11.9(19) . . . . ?
N5B C2 C3 C20B -11.5(19) . . . . ?
N1 C2 C3 C20 166.8(8) . . . . ?
C1 C2 C3 C20 -12.8(9) . . . . ?
N5B C2 C3 C20 -12.4(9) . . . . ?
C2 C3 C4 N2 -5.8(6) . . . . ?
C20B C3 C4 N2 177.8(19) . . . . ?
C20 C3 C4 N2 178.6(8) . . . . ?
C2 C3 C4 C5 175.6(4) . . . . ?
C20B C3 C4 C5 -0.8(19) . . . . ?
C20 C3 C4 C5 -0.1(9) . . . . ?
N2 C4 C5 C6 -1.0(5) . . . . ?
C3 C4 C5 C6 177.8(4) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C5 C6 C7 N2 -1.0(4) . . . . ?
C5 C6 C7 C8 178.6(4) . . . . ?
N2 C7 C8 C9 9.2(6) . . . . ?
C6 C7 C8 C9 -170.3(4) . . . . ?
N2 C7 C8 C27B -173.8(18) . . . . ?
C6 C7 C8 C27B 6.7(18) . . . . ?
N2 C7 C8 C27 -175.2(5) . . . . ?
C6 C7 C8 C27 5.3(7) . . . . ?
C7 C8 C9 N3 -1.3(7) . . . . ?
C27B C8 C9 N3 -178.6(16) . . . . ?
C27 C8 C9 N3 -176.8(5) . . . . ?
C7 C8 C9 C10 174.9(4) . . . . ?
C27B C8 C9 C10 -2.4(17) . . . . ?
C27 C8 C9 C10 -0.7(7) . . . . ?
N3 C9 C10 C11 -0.4(5) . . . . ?
C8 C9 C10 C11 -177.1(4) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C10 C11 C12 N3 -0.9(5) . . . . ?
C10 C11 C12 C13 177.8(4) . . . . ?
N3 C12 C13 C14 -0.7(7) . . . . ?
C11 C12 C13 C14 -179.2(4) . . . . ?
N3 C12 C13 C34 178.2(17) . . . . ?
C11 C12 C13 C34 -0.3(18) . . . . ?
N3 C12 C13 C34B 178.5(15) . . . . ?
C11 C12 C13 C34B 0.0(16) . . . . ?
C12 C13 C14 N4 -4.3(7) . . . . ?
C34 C13 C14 N4 176.8(16) . . . . ?
C34B C13 C14 N4 176.5(15) . . . . ?
C12 C13 C14 C15 172.6(4) . . . . ?
C34 C13 C14 C15 -6.4(16) . . . . ?
C34B C13 C14 C15 -6.6(16) . . . . ?
N4 C14 C15 C16 0.5(5) . . . . ?
C13 C14 C15 C16 -176.9(4) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 N4 0.8(5) . . . . ?
C15 C16 C17 C18 -179.0(4) . . . . ?
N4 C17 C18 C19 2.6(6) . . . . ?
C16 C17 C18 C19 -177.7(4) . . . . ?
N4 C17 C18 C41 179.2(4) . . . . ?
C16 C17 C18 C41 -1.2(6) . . . . ?
C17 C18 C19 N1 10.9(6) . . . . ?
C41 C18 C19 N1 -165.5(4) . . . . ?
C17 C18 C19 N5 -171.2(4) . . . . ?
C41 C18 C19 N5 12.4(5) . . . . ?
C17 C18 C19 C1B -176.5(8) . . . . ?
C41 C18 C19 C1B 7.1(9) . . . . ?
C19 C18 C41 C42 -118.2(4) . . . . ?
C17 C18 C41 C42 65.1(5) . . . . ?
C19 C18 C41 C46 63.5(5) . . . . ?
C17 C18 C41 C46 -113.2(4) . . . . ?
C46 C41 C42 C43 -0.5(6) . . . . ?
C18 C41 C42 C43 -178.8(4) . . . . ?
C41 C42 C43 C44 -0.3(6) . . . . ?
C42 C43 C44 C45 0.4(6) . . . . ?
C42 C43 C44 C47 -178.2(4) . . . . ?
C43 C44 C45 C46 0.3(6) . . . . ?
C47 C44 C45 C46 178.9(4) . . . . ?
C44 C45 C46 C41 -1.1(6) . . . . ?
C42 C41 C46 C45 1.2(6) . . . . ?
C18 C41 C46 C45 179.6(4) . . . . ?
C45 C44 C47 F12 -68.3(6) . . . . ?
C43 C44 C47 F12 110.3(5) . . . . ?
C45 C44 C47 F11 169.1(4) . . . . ?
C43 C44 C47 F11 -12.3(6) . . . . ?
C45 C44 C47 F10 49.1(5) . . . . ?
C43 C44 C47 F10 -132.3(4) . . . . ?
C2 C3 C20 C21 -64.3(9) . . . . ?
C4 C3 C20 C21 111.6(7) . . . . ?
C20B C3 C20 C21 -88(71) . . . . ?
C2 C3 C20 C25 115.7(9) . . . . ?
C4 C3 C20 C25 -68.4(7) . . . . ?
C20B C3 C20 C25 92(71) . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
C3 C20 C21 C22 180.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C21 C22 C23 C26 178.7(10) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C26 C23 C24 C25 -178.7(10) . . . . ?
C23 C24 C25 C20 0.0 . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C3 C20 C25 C24 180.0 . . . . ?
C22 C23 C26 F2 139.7(13) . . . . ?
C24 C23 C26 F2 -41.6(13) . . . . ?
C22 C23 C26 F3 20.0(16) . . . . ?
C24 C23 C26 F3 -161.3(12) . . . . ?
C22 C23 C26 F1 -100.9(13) . . . . ?
C24 C23 C26 F1 77.8(13) . . . . ?
C2 C3 C20B C21B -59.0(19) . . . . ?
C4 C3 C20B C21B 117.7(13) . . . . ?
C20 C3 C20B C21B 97(72) . . . . ?
C2 C3 C20B C25B 123.4(19) . . . . ?
C4 C3 C20B C25B -59.9(18) . . . . ?
C20 C3 C20B C25B -80(72) . . . . ?
C25B C20B C21B C22B 0.0 . . . . ?
C3 C20B C21B C22B -177.8(9) . . . . ?
C20B C21B C22B C23B 0.0 . . . . ?
C21B C22B C23B C24B 0.0 . . . . ?
C21B C22B C23B C26B 179(3) . . . . ?
C22B C23B C24B C25B 0.0 . . . . ?
C26B C23B C24B C25B -179(3) . . . . ?
C23B C24B C25B C20B 0.0 . . . . ?
C21B C20B C25B C24B 0.0 . . . . ?
C3 C20B C25B C24B 177.4(11) . . . . ?
C22B C23B C26B F1B 120(3) . . . . ?
C24B C23B C26B F1B -61(2) . . . . ?
C22B C23B C26B F2B -1(4) . . . . ?
C24B C23B C26B F2B 177.6(19) . . . . ?
C22B C23B C26B F3B -119(3) . . . . ?
C24B C23B C26B F3B 60(2) . . . . ?
C9 C8 C27 C28 100.6(4) . . . . ?
C7 C8 C27 C28 -75.4(5) . . . . ?
C27B C8 C27 C28 115(16) . . . . ?
C9 C8 C27 C32 -72.6(5) . . . . ?
C7 C8 C27 C32 111.4(4) . . . . ?
C27B C8 C27 C32 -58(16) . . . . ?
C32 C27 C28 C29 0.0 . . . . ?
C8 C27 C28 C29 -173.1(3) . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C28 C29 C30 C33 176.9(5) . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C33 C30 C31 C32 -176.7(5) . . . . ?
C30 C31 C32 C27 0.0 . . . . ?
C28 C27 C32 C31 0.0 . . . . ?
C8 C27 C32 C31 173.2(4) . . . . ?
C29 C30 C33 F5 171.8(5) . . . . ?
C31 C30 C33 F5 -11.5(8) . . . . ?
C29 C30 C33 F6 -65.5(7) . . . . ?
C31 C30 C33 F6 111.2(6) . . . . ?
C29 C30 C33 F4 52.4(7) . . . . ?
C31 C30 C33 F4 -130.8(4) . . . . ?
C9 C8 C27B C28B 89.1(11) . . . . ?
C7 C8 C27B C28B -88.3(14) . . . . ?
C27 C8 C27B C28B -77(16) . . . . ?
C9 C8 C27B C32B -90.9(11) . . . . ?
C7 C8 C27B C32B 91.7(14) . . . . ?
C27 C8 C27B C32B 103(16) . . . . ?
C32B C27B C28B C29B 0.0 . . . . ?
C8 C27B C28B C29B 180.0 . . . . ?
C27B C28B C29B C30B 0.0 . . . . ?
C28B C29B C30B C31B 0.0 . . . . ?
C28B C29B C30B C33B 172.3(16) . . . . ?
C29B C30B C31B C32B 0.0 . . . . ?
C33B C30B C31B C32B -172.8(14) . . . . ?
C30B C31B C32B C27B 0.0 . . . . ?
C28B C27B C32B C31B 0.0 . . . . ?
C8 C27B C32B C31B 180.0 . . . . ?
C29B C30B C33B F5B 144(2) . . . . ?
C31B C30B C33B F5B -43.1(18) . . . . ?
C29B C30B C33B F6B 23(2) . . . . ?
C31B C30B C33B F6B -164.3(16) . . . . ?
C29B C30B C33B F4B -97(2) . . . . ?
C31B C30B C33B F4B 75.5(17) . . . . ?
C12 C13 C34 C35 -78.7(19) . . . . ?
C14 C13 C34 C35 100.3(16) . . . . ?
C12 C13 C34 C39 94.2(17) . . . . ?
C14 C13 C34 C39 -86.8(14) . . . . ?
C39 C34 C35 C36 0.0 . . . . ?
C13 C34 C35 C36 173(2) . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C35 C36 C37 C40 -176(2) . . . . ?
C36 C37 C38 C39 0.0 . . . . ?
C40 C37 C38 C39 176(2) . . . . ?
C37 C38 C39 C34 0.0 . . . . ?
C35 C34 C39 C38 0.0 . . . . ?
C13 C34 C39 C38 -173(2) . . . . ?
C38 C37 C40 F7 -78(2) . . . . ?
C36 C37 C40 F7 97.9(17) . . . . ?
C38 C37 C40 F8 161.9(17) . . . . ?
C36 C37 C40 F8 -22(2) . . . . ?
C38 C37 C40 F9 41(2) . . . . ?
C36 C37 C40 F9 -143.2(16) . . . . ?
C12 C13 C34B C35B -70.6(16) . . . . ?
C14 C13 C34B C35B 108.7(13) . . . . ?
C12 C13 C34B C39B 112.3(13) . . . . ?
C14 C13 C34B C39B -68.4(16) . . . . ?
C39B C34B C35B C36B 0.0 . . . . ?
C13 C34B C35B C36B -177(2) . . . . ?
C34B C35B C36B C37B 0.0 . . . . ?
C35B C36B C37B C38B 0.0 . . . . ?
C35B C36B C37B C40B -174.0(19) . . . . ?
C36B C37B C38B C39B 0.0 . . . . ?
C40B C37B C38B C39B 174(2) . . . . ?
C37B C38B C39B C34B 0.0 . . . . ?
C35B C34B C39B C38B 0.0 . . . . ?
C13 C34B C39B C38B 177(2) . . . . ?
C38B C37B C40B F7B -114.2(19) . . . . ?
C36B C37B C40B F7B 59.8(18) . . . . ?
C38B C37B C40B F8B 126.4(19) . . . . ?
C36B C37B C40B F8B -59.6(19) . . . . ?
C38B C37B C40B F9B 6(2) . . . . ?
C36B C37B C40B F9B -179.7(15) . . . . ?
C18 C19 N1 C2 173.4(4) . . . . ?
N5 C19 N1 C2 -4.8(4) . . . . ?
C1B C19 N1 C2 0.3(8) . . . . ?
C3 C2 N1 C19 -174.8(4) . . . . ?
C1 C2 N1 C19 4.9(4) . . . . ?
N5B C2 N1 C19 4.6(4) . . . . ?
C3 C4 N2 C7 -178.5(4) . . . . ?
C5 C4 N2 C7 0.4(4) . . . . ?
C8 C7 N2 C4 -179.2(4) . . . . ?
C6 C7 N2 C4 0.4(4) . . . . ?
C13 C12 N3 C9 -178.0(4) . . . . ?
C11 C12 N3 C9 0.6(5) . . . . ?
C8 C9 N3 C12 176.4(4) . . . . ?
C10 C9 N3 C12 -0.2(5) . . . . ?
C18 C17 N4 C14 179.2(4) . . . . ?
C16 C17 N4 C14 -0.5(4) . . . . ?
C13 C14 N4 C17 177.4(4) . . . . ?
C15 C14 N4 C17 0.0(5) . . . . ?
N1 C2 C1 O1 176.3(4) . . . . ?
C3 C2 C1 O1 -4.0(5) . . . . ?
N5B C2 C1 O1 -178(2) . . . . ?
N1 C2 C1 N5 -2.9(3) . . . . ?
C3 C2 C1 N5 176.7(4) . . . . ?
N5B C2 C1 N5 3(2) . . . . ?
O1 C1 N5 N6 0.2(4) . . . . ?
C2 C1 N5 N6 179.4(3) . . . . ?
O1 C1 N5 C19 -179.4(3) . . . . ?
C2 C1 N5 C19 -0.1(2) . . . . ?
N1 C19 N5 C1 3.1(3) . . . . ?
C18 C19 N5 C1 -175.2(4) . . . . ?
C1B C19 N5 C1 -134(7) . . . . ?
N1 C19 N5 N6 -176.4(4) . . . . ?
C18 C19 N5 N6 5.3(5) . . . . ?
C1B C19 N5 N6 46(7) . . . . ?
N5 C1 O1 H2A -15.9 . . . . ?
C2 C1 O1 H2A 165.1 . . . . ?
N1 C19 C1B O1B -157.2(12) . . . . ?
C18 C19 C1B O1B 29.2(17) . . . . ?
N5 C19 C1B O1B -113(7) . . . . ?
N1 C19 C1B N5B -5.2(12) . . . . ?
C18 C19 C1B N5B -178.8(5) . . . . ?
N5 C19 C1B N5B 39(6) . . . . ?
O1B C1B N5B N6B -7.4(19) . . . . ?
C19 C1B N5B N6B -159.7(11) . . . . ?
O1B C1B N5B C2 160.1(13) . . . . ?
C19 C1B N5B C2 7.8(11) . . . . ?
N1 C2 N5B C1B -8.2(9) . . . . ?
C3 C2 N5B C1B 171.1(7) . . . . ?
C1 C2 N5B C1B 178(2) . . . . ?
N1 C2 N5B N6B 157.8(11) . . . . ?
C3 C2 N5B N6B -22.9(13) . . . . ?
C1 C2 N5B N6B -16(2) . . . . ?
N5B C1B O1B H3B 75.8 . . . . ?
C19 C1B O1B H3B -138.5 . . . . ?
H3 O2 C48 C49 -2.2 . . . . ?
H2B O3B C50B C51B 34.1 . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N3 0.88 2.36 2.902(4) 120.5 .
N2 H2 N1 0.88 2.41 2.943(4) 119.7 .
N4 H4 N3 0.88 2.38 2.923(4) 120.3 .
N4 H4 N3 0.88 2.38 2.923(4) 120.3 .
N6 H6A N3 0.94(2) 2.56(3) 3.409(11) 150(4) 2_667
N6 H6B O3 0.923(19) 2.07(4) 2.721(13) 127(4) .
N6B H6D O2B 0.93(2) 2.17(4) 2.99(2) 147(5) .
O2 H2A O1 0.85 2.01 2.809(11) 155.4 .
O3 H3 O2 0.84 1.75 2.331(17) 124.3 .
O2B H2B O3B 0.86 2.15 3.01(3) 173.2 .
O3B H3B O1B 0.86 2.19 3.025(18) 163.4 .
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.055


data_10mz508_0m
_database_code_depnum_ccdc_archive 'CCDC 919812'
#TrackingRef '16863_web_deposit_cif_file_2_ChristianBrueckner_1358220260.JH-A-23F2_10mz508_0m(9c).cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H28 F12 N6 O, 2(C2 H6 O)'
_chemical_formula_sum            'C51 H40 F12 N6 O3'
_chemical_formula_weight         1012.89
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   12.6859(12)
_cell_length_b                   12.9511(12)
_cell_length_c                   14.5378(13)
_cell_angle_alpha                81.7260(10)
_cell_angle_beta                 76.306(2)
_cell_angle_gamma                84.1850(10)
_cell_volume                     2290.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4965
_cell_measurement_theta_min      2.2152
_cell_measurement_theta_max      27.9510
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6429
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Apex2 v2009.7-0 (Bruker, 2009)'
_exptl_special_details           
;
The structure is virtually isostructural with its counterpart with
a C=C double bond in place of the methylene group in the present
structure (JH-A-23F1_10mz486_0m) with similar unit cell parameters
and packing and also similar disorder of the heterocycle and the
ethanol solvate molecules).
The structure exhibits several types of disorder. Several of the
trifluoromethyl groups show pronounced rotational disorder combined
with a slight sideways shifting of the adjacent phenyl rings. For one
of the trifluoromethyl groups this disorder was refined as disordered
over each two sites. The C-F bonds, the F...F distances and the
C-C(CF3) bonds were each restrained to be similar. The disordered
phenyl ring was constrained to resemble an ideal hexagon with a C-C
distance of 1.39 Angstrom. Overlapping disordered atoms were constrained
to have identical ADPs. The occupancy ratio for refined to 0.817(4) to
0.183(4).
The lactole moiety is flip disordered with the C=O and N-NH2 units
of the disordered units occupying mutually exclusive positions.
Associated with this disorder is disorder of two interstitial ethanol
molecules that are hydrogen bonded to the keto O and the amino groups.
The common occupancy ratio refined to 0.725(5) to 0.275(5).
The C-C(=O)-N(-N)-C units were each restrained to be flat and equivalent
distances to be the same for both moieties. The overlapping atoms of each
unit were constrained to have identical ADPs.
Equivalent bonds in the disordered ethanol molecules were restrained
to be similar. The O-C and C-C distances were restrained to be 1.426(20)
and 1.50(2) Angstroms. ADPs were restrained to be close to isotropic.
Ethanol O-H and amine hydrogen atoms were placed based on hydrogen
bonding considerations and were initially refined using appropriate
restraints.
;
_diffrn_ambient_temperature      100(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  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19920
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         26.37
_reflns_number_total             9252
_reflns_number_gt                6298
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'Apex2 v2009.7-0 (Bruker, 2009)'
_computing_cell_refinement       'Apex2 v2009.7-0'
_computing_data_reduction        'Apex2 v2009.7-0'
_computing_structure_solution    
'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_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^)+(0.0977P)^2^+2.0358P] 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_number_reflns         9252
_refine_ls_number_parameters     703
_refine_ls_number_restraints     125
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.2038
_refine_ls_wR_factor_gt          0.1846
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.055
_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 -0.0046(2) 0.5546(2) 0.6647(2) 0.0315(6) Uani 1 1 d D . .
C2 C 0.0099(11) 0.4527(10) 0.7191(8) 0.0334(6) Uani 0.725(5) 1 d PD A 1
N5 N 0.1018(9) 0.4063(6) 0.6669(7) 0.0361(6) Uani 0.725(5) 1 d PD A 1
N6 N 0.1277(6) 0.3020(8) 0.6883(9) 0.0377(14) Uani 0.725(5) 1 d PD A 1
H6A H 0.070(2) 0.261(3) 0.704(3) 0.045 Uiso 0.725(5) 1 d PD A 1
H6B H 0.159(3) 0.277(3) 0.739(2) 0.045 Uiso 0.725(5) 1 d PD A 1
O1 O -0.0565(11) 0.4099(9) 0.7911(9) 0.0503(18) Uani 0.725(5) 1 d PD A 1
C2B C 0.103(3) 0.4031(18) 0.668(2) 0.0361(6) Uani 0.275(5) 1 d PD A 2
N5B N 0.012(2) 0.454(2) 0.7171(16) 0.0334(6) Uani 0.275(5) 1 d PD A 2
N6B N -0.045(4) 0.395(4) 0.797(3) 0.0503(18) Uani 0.275(5) 1 d PD A 2
H6C H -0.051(10) 0.327(5) 0.786(7) 0.060 Uiso 0.275(5) 1 d PD A 2
H6D H -0.008(9) 0.378(7) 0.844(6) 0.060 Uiso 0.275(5) 1 d PD A 2
O1B O 0.1520(17) 0.3121(18) 0.676(2) 0.0377(14) Uani 0.275(5) 1 d PD A 2
C3 C 0.1413(2) 0.4765(2) 0.58305(19) 0.0302(6) Uani 1 1 d D . .
C4 C 0.2380(2) 0.4565(2) 0.51628(19) 0.0299(6) Uani 1 1 d . A .
C5 C 0.2715(2) 0.5191(2) 0.42968(19) 0.0307(6) Uani 1 1 d . . .
C6 C 0.3710(2) 0.5052(2) 0.3601(2) 0.0356(7) Uani 1 1 d . A .
H6 H 0.4273 0.4520 0.3652 0.043 Uiso 1 1 calc R . .
C7 C 0.3707(2) 0.5820(2) 0.2850(2) 0.0346(6) Uani 1 1 d . . .
H7 H 0.4261 0.5903 0.2282 0.042 Uiso 1 1 calc R A .
C8 C 0.2731(2) 0.6472(2) 0.30660(19) 0.0307(6) Uani 1 1 d . A .
C9 C 0.2447(2) 0.7379(2) 0.24945(19) 0.0306(6) Uani 1 1 d . . .
C10 C 0.1538(2) 0.8076(2) 0.27346(19) 0.0319(6) Uani 1 1 d . A .
C11 C 0.1335(3) 0.9040(2) 0.2061(2) 0.0423(7) Uani 1 1 d . . .
H11A H 0.1919 0.9525 0.1958 0.051 Uiso 1 1 calc R A .
H11B H 0.1284 0.8852 0.1437 0.051 Uiso 1 1 calc R . .
C12 C 0.0264(3) 0.9515(2) 0.2576(2) 0.0388(7) Uani 1 1 d . A .
H12A H -0.0308 0.9502 0.2220 0.047 Uiso 1 1 calc R . .
H12B H 0.0328 1.0247 0.2670 0.047 Uiso 1 1 calc R . .
C13 C 0.0019(2) 0.8823(2) 0.35218(19) 0.0309(6) Uani 1 1 d D . .
C14 C -0.0861(2) 0.9064(2) 0.4257(2) 0.0303(6) Uani 1 1 d D A .
C15 C -0.1130(2) 0.8503(2) 0.5173(2) 0.0296(6) Uani 1 1 d D . .
C16 C -0.1895(2) 0.8834(2) 0.5983(2) 0.0335(6) Uani 1 1 d . A .
H16 H -0.2345 0.9467 0.5994 0.040 Uiso 1 1 calc R . .
C17 C -0.1870(2) 0.8084(2) 0.6740(2) 0.0354(6) Uani 1 1 d . . .
H17 H -0.2291 0.8112 0.7372 0.043 Uiso 1 1 calc R A .
C18 C -0.1104(2) 0.7250(2) 0.64251(19) 0.0318(6) Uani 1 1 d . A .
C19 C -0.0857(2) 0.6311(2) 0.6973(2) 0.0328(6) Uani 1 1 d . A .
C20 C 0.3153(2) 0.3666(2) 0.53906(19) 0.0313(6) Uani 1 1 d . . .
C21 C 0.3663(2) 0.3665(2) 0.6140(2) 0.0348(6) Uani 1 1 d . A .
H21 H 0.3507 0.4232 0.6510 0.042 Uiso 1 1 calc R . .
C22 C 0.4388(3) 0.2854(2) 0.6350(2) 0.0363(7) Uani 1 1 d . . .
H22 H 0.4725 0.2859 0.6867 0.044 Uiso 1 1 calc R A .
C23 C 0.4627(2) 0.2024(2) 0.5805(2) 0.0335(6) Uani 1 1 d . A .
C24 C 0.4124(2) 0.2018(2) 0.5054(2) 0.0360(7) Uani 1 1 d . . .
H24 H 0.4280 0.1452 0.4683 0.043 Uiso 1 1 calc R A .
C25 C 0.3395(2) 0.2838(2) 0.4851(2) 0.0326(6) Uani 1 1 d . A .
H25 H 0.3055 0.2834 0.4336 0.039 Uiso 1 1 calc R . .
C26 C 0.5387(3) 0.1142(2) 0.6058(2) 0.0410(7) Uani 1 1 d . . .
C27 C 0.3210(2) 0.7612(2) 0.15484(19) 0.0332(6) Uani 1 1 d . A .
C28 C 0.3193(3) 0.7056(2) 0.0802(2) 0.0395(7) Uani 1 1 d . . .
H28 H 0.2707 0.6519 0.0898 0.047 Uiso 1 1 calc R A .
C29 C 0.3889(3) 0.7289(3) -0.0088(2) 0.0453(8) Uani 1 1 d . A .
H29 H 0.3870 0.6918 -0.0602 0.054 Uiso 1 1 calc R . .
C30 C 0.4605(3) 0.8057(3) -0.0222(2) 0.0430(8) Uani 1 1 d . . .
C31 C 0.4649(3) 0.8597(3) 0.0520(2) 0.0449(8) Uani 1 1 d . A .
H31 H 0.5155 0.9116 0.0427 0.054 Uiso 1 1 calc R . .
C32 C 0.3947(3) 0.8374(2) 0.1403(2) 0.0398(7) Uani 1 1 d . . .
H32 H 0.3972 0.8748 0.1914 0.048 Uiso 1 1 calc R A .
C33 C 0.5318(4) 0.8375(3) -0.1183(3) 0.0621(11) Uani 1 1 d . A .
C41 C -0.1468(3) 0.6150(2) 0.7995(2) 0.0375(7) Uani 1 1 d . . .
C42 C -0.2564(3) 0.5996(2) 0.8242(2) 0.0449(8) Uani 1 1 d . A .
H42 H -0.2954 0.5996 0.7758 0.054 Uiso 1 1 calc R . .
C43 C -0.3103(3) 0.5840(3) 0.9204(3) 0.0556(10) Uani 1 1 d . . .
H43 H -0.3857 0.5729 0.9373 0.067 Uiso 1 1 calc R A .
C44 C -0.2544(4) 0.5848(3) 0.9909(2) 0.0557(10) Uani 1 1 d . A .
C45 C -0.1447(4) 0.5990(3) 0.9670(3) 0.0642(11) Uani 1 1 d . . .
H45 H -0.1060 0.5985 1.0155 0.077 Uiso 1 1 calc R A .
C46 C -0.0911(3) 0.6139(3) 0.8720(2) 0.0545(9) Uani 1 1 d . A .
H46 H -0.0154 0.6236 0.8557 0.065 Uiso 1 1 calc R . .
C47 C -0.3158(4) 0.5701(3) 1.0932(3) 0.0727(13) Uani 1 1 d . . .
F1 F 0.49443(18) 0.05390(17) 0.68553(17) 0.0715(7) Uani 1 1 d . A .
F2 F 0.62898(15) 0.14538(15) 0.62267(14) 0.0504(5) Uani 1 1 d . A .
F3 F 0.57426(19) 0.05128(16) 0.53786(16) 0.0648(6) Uani 1 1 d . A .
F4 F 0.6331(2) 0.8516(2) -0.11395(18) 0.0926(9) Uani 1 1 d . . .
F5 F 0.54091(19) 0.7678(2) -0.17909(14) 0.0705(7) Uani 1 1 d . . .
F6 F 0.4948(3) 0.9270(3) -0.1592(2) 0.1465(18) Uani 1 1 d . . .
C34 C -0.1549(4) 1.0063(3) 0.4071(3) 0.0307(6) Uani 0.817(4) 1 d PGD A 1
C35 C -0.2285(5) 1.0097(3) 0.3493(4) 0.0370(10) Uani 0.817(4) 1 d PG A 1
H35 H -0.2408 0.9477 0.3267 0.044 Uiso 0.817(4) 1 calc PR A 1
C36 C -0.2840(4) 1.1039(4) 0.3245(4) 0.0459(12) Uani 0.817(4) 1 d PG A 1
H36 H -0.3343 1.1062 0.2849 0.055 Uiso 0.817(4) 1 calc PR A 1
C37 C -0.2659(4) 1.1946(3) 0.3575(3) 0.0430(8) Uani 0.817(4) 1 d PGD A 1
C38 C -0.1924(3) 1.1912(3) 0.4153(3) 0.0357(10) Uani 0.817(4) 1 d PG A 1
H38 H -0.1800 1.2532 0.4379 0.043 Uiso 0.817(4) 1 calc PR A 1
C39 C -0.1369(3) 1.0970(4) 0.4402(2) 0.0328(9) Uani 0.817(4) 1 d PG A 1
H39 H -0.0866 1.0947 0.4797 0.039 Uiso 0.817(4) 1 calc PR A 1
C40 C -0.3183(4) 1.2999(4) 0.3304(4) 0.0600(13) Uani 0.817(4) 1 d PD A 1
F7 F -0.2467(3) 1.3656(2) 0.2790(3) 0.0892(13) Uani 0.817(4) 1 d PD A 1
F8 F -0.3948(3) 1.2960(2) 0.2833(3) 0.0842(13) Uani 0.817(4) 1 d PD A 1
F9 F -0.3679(3) 1.3490(2) 0.4069(3) 0.0801(10) Uani 0.817(4) 1 d PD A 1
C34B C -0.152(2) 1.0041(15) 0.4045(14) 0.0307(6) Uani 0.183(4) 1 d PGD A 2
C35B C -0.242(2) 1.0045(12) 0.3660(19) 0.0370(10) Uani 0.183(4) 1 d PG A 2
H35B H -0.2668 0.9404 0.3577 0.044 Uiso 0.183(4) 1 calc PR A 2
C36B C -0.297(2) 1.0988(18) 0.340(2) 0.0459(12) Uani 0.183(4) 1 d PG A 2
H36B H -0.3584 1.0991 0.3137 0.055 Uiso 0.183(4) 1 calc PR A 2
C37B C -0.2604(18) 1.1927(12) 0.3522(15) 0.0430(8) Uani 0.183(4) 1 d PGD A 2
C38B C -0.1699(17) 1.1922(15) 0.3906(14) 0.0357(10) Uani 0.183(4) 1 d PG A 2
H38B H -0.1452 1.2563 0.3990 0.043 Uiso 0.183(4) 1 calc PR A 2
C39B C -0.1155(14) 1.098(2) 0.4167(14) 0.0328(9) Uani 0.183(4) 1 d PG A 2
H39B H -0.0536 1.0976 0.4430 0.039 Uiso 0.183(4) 1 calc PR A 2
C40B C -0.3149(15) 1.2870(14) 0.3066(13) 0.0600(13) Uani 0.183(4) 1 d PD A 2
F7B F -0.3109(16) 1.3693(10) 0.3497(14) 0.0842(13) Uani 0.183(4) 1 d PD A 2
F8B F -0.4192(13) 1.2757(15) 0.3132(15) 0.0892(13) Uani 0.183(4) 1 d PD A 2
F9B F -0.2719(12) 1.3121(9) 0.2143(10) 0.0801(10) Uani 0.183(4) 1 d PD A 2
F10 F -0.3815(2) 0.65322(18) 1.11777(14) 0.0725(7) Uani 1 1 d . A .
F11 F -0.3726(4) 0.4898(2) 1.11493(18) 0.1316(16) Uani 1 1 d . A .
F12 F -0.2468(3) 0.5567(2) 1.15411(17) 0.1047(11) Uani 1 1 d . A .
N1 N 0.07373(19) 0.56421(17) 0.58220(16) 0.0296(5) Uani 1 1 d . A .
N2 N 0.21521(19) 0.60611(17) 0.39406(16) 0.0301(5) Uani 1 1 d . A .
H2 H 0.1511 0.6318 0.4233 0.036 Uiso 1 1 calc R . .
N3 N 0.07650(18) 0.79926(17) 0.35581(16) 0.0297(5) Uani 1 1 d . A .
N4 N -0.06718(18) 0.75431(17) 0.54746(16) 0.0301(5) Uani 1 1 d . A .
H4 H -0.0171 0.7168 0.5109 0.036 Uiso 1 1 calc R . .
O2 O 0.1769(6) 0.1631(6) 0.8383(4) 0.117(2) Uani 0.725(5) 1 d PDU A 1
H2A H 0.1164 0.1626 0.8773 0.176 Uiso 0.725(5) 1 calc PRD A 1
C48 C 0.2588(6) 0.1230(9) 0.8860(7) 0.093(2) Uani 0.725(5) 1 d PDU A 1
H48A H 0.2651 0.1720 0.9305 0.112 Uiso 0.725(5) 1 calc PR A 1
H48B H 0.3291 0.1183 0.8388 0.112 Uiso 0.725(5) 1 calc PR A 1
C49 C 0.2385(6) 0.0216(6) 0.9386(5) 0.092(2) Uani 0.725(5) 1 d PDU A 1
H49A H 0.1628 0.0218 0.9748 0.137 Uiso 0.725(5) 1 calc PR A 1
H49B H 0.2872 0.0048 0.9827 0.137 Uiso 0.725(5) 1 calc PR A 1
H49C H 0.2517 -0.0309 0.8942 0.137 Uiso 0.725(5) 1 calc PR A 1
O2B O 0.1265(17) 0.1922(17) 0.8689(11) 0.117(2) Uani 0.275(5) 1 d PD A 2
H2B H 0.1251 0.2106 0.8113 0.176 Uiso 0.275(5) 1 calc PR A 2
C48B C 0.2227(19) 0.126(3) 0.8746(12) 0.093(2) Uani 0.275(5) 1 d PD A 2
H48C H 0.2878 0.1650 0.8434 0.112 Uiso 0.275(5) 1 calc PR A 2
H48D H 0.2245 0.0645 0.8412 0.112 Uiso 0.275(5) 1 calc PR A 2
C49B C 0.2230(8) 0.0929(16) 0.9745(3) 0.092(2) Uani 0.275(5) 1 d PD A 2
H49D H 0.1592 0.0534 1.0045 0.137 Uiso 0.275(5) 1 calc PR A 2
H49E H 0.2207 0.1545 1.0072 0.137 Uiso 0.275(5) 1 calc PR A 2
H49F H 0.2893 0.0485 0.9790 0.137 Uiso 0.275(5) 1 calc PR A 2
O3 O -0.0158(4) 0.2394(4) 0.9291(3) 0.0887(14) Uani 0.725(5) 1 d PRDU A 1
H3 H -0.0333 0.2893 0.8906 0.133 Uiso 0.725(5) 1 calc PR A 1
C50 C -0.0883(5) 0.2435(6) 1.0216(5) 0.080(2) Uani 0.725(5) 1 d PDU A 1
H50A H -0.1608 0.2217 1.0212 0.097 Uiso 0.725(5) 1 calc PR A 1
H50B H -0.0971 0.3155 1.0391 0.097 Uiso 0.725(5) 1 calc PR A 1
C51 C -0.0391(8) 0.1719(5) 1.0896(7) 0.097(3) Uani 0.725(5) 1 d PDU A 1
H51A H 0.0278 0.1996 1.0956 0.146 Uiso 0.725(5) 1 calc PR A 1
H51B H -0.0217 0.1032 1.0667 0.146 Uiso 0.725(5) 1 calc PR A 1
H51C H -0.0902 0.1649 1.1519 0.146 Uiso 0.725(5) 1 calc PR A 1
O3B O -0.0455(11) 0.2884(11) 0.9809(10) 0.0887(14) Uani 0.275(5) 1 d PD A 2
H3B H 0.0113 0.2507 0.9618 0.133 Uiso 0.275(5) 1 calc PRD A 2
C50B C -0.1136(15) 0.2324(15) 1.0723(13) 0.080(2) Uani 0.275(5) 1 d PD A 2
H50C H -0.1174 0.2694 1.1282 0.097 Uiso 0.275(5) 1 calc PR A 2
H50D H -0.1881 0.2239 1.0659 0.097 Uiso 0.275(5) 1 calc PR A 2
C51B C -0.049(2) 0.1312(13) 1.078(2) 0.097(3) Uani 0.275(5) 1 d PD A 2
H51D H 0.0285 0.1430 1.0577 0.146 Uiso 0.275(5) 1 calc PR A 2
H51E H -0.0683 0.0862 1.0369 0.146 Uiso 0.275(5) 1 calc PR A 2
H51F H -0.0649 0.0972 1.1443 0.146 Uiso 0.275(5) 1 calc PR A 2
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 0.0368(15) 0.0265(14) 0.0302(14) -0.0003(11) -0.0066(12) -0.0040(11)
C2 0.0410(16) 0.0253(13) 0.0317(15) 0.0016(11) -0.0068(12) -0.0025(12)
N5 0.0458(15) 0.0268(14) 0.0345(14) -0.0010(11) -0.0082(12) -0.0032(12)
N6 0.033(4) 0.024(2) 0.045(4) 0.008(2) 0.006(3) -0.005(2)
O1 0.053(4) 0.035(4) 0.051(2) 0.006(2) 0.002(2) 0.006(3)
C2B 0.0458(15) 0.0268(14) 0.0345(14) -0.0010(11) -0.0082(12) -0.0032(12)
N5B 0.0410(16) 0.0253(13) 0.0317(15) 0.0016(11) -0.0068(12) -0.0025(12)
N6B 0.053(4) 0.035(4) 0.051(2) 0.006(2) 0.002(2) 0.006(3)
O1B 0.033(4) 0.024(2) 0.045(4) 0.008(2) 0.006(3) -0.005(2)
C3 0.0418(16) 0.0217(13) 0.0275(14) -0.0012(10) -0.0101(12) -0.0015(11)
C4 0.0402(15) 0.0192(12) 0.0312(14) -0.0032(11) -0.0109(12) 0.0008(11)
C5 0.0377(15) 0.0242(13) 0.0301(14) -0.0051(11) -0.0091(12) 0.0042(11)
C6 0.0367(15) 0.0312(15) 0.0364(16) -0.0029(12) -0.0071(12) 0.0051(12)
C7 0.0360(15) 0.0318(15) 0.0325(15) -0.0019(12) -0.0049(12) 0.0046(12)
C8 0.0357(15) 0.0262(14) 0.0293(14) -0.0029(11) -0.0067(12) -0.0007(11)
C9 0.0355(15) 0.0269(14) 0.0277(14) -0.0023(11) -0.0054(11) 0.0003(11)
C10 0.0367(15) 0.0270(14) 0.0308(15) -0.0014(11) -0.0070(12) -0.0009(12)
C11 0.0483(18) 0.0349(16) 0.0364(16) 0.0044(13) -0.0055(14) 0.0083(14)
C12 0.0440(17) 0.0329(15) 0.0331(16) 0.0031(12) -0.0042(13) 0.0060(13)
C13 0.0354(15) 0.0249(14) 0.0316(15) 0.0010(11) -0.0098(12) 0.0004(11)
C14 0.0329(14) 0.0244(13) 0.0342(15) -0.0036(11) -0.0099(12) 0.0011(11)
C15 0.0280(14) 0.0244(13) 0.0365(15) -0.0042(11) -0.0077(12) -0.0002(11)
C16 0.0319(15) 0.0310(15) 0.0358(15) -0.0074(12) -0.0040(12) 0.0024(12)
C17 0.0367(16) 0.0356(15) 0.0310(15) -0.0074(12) -0.0019(12) 0.0031(12)
C18 0.0330(15) 0.0312(14) 0.0298(15) -0.0029(11) -0.0051(12) -0.0020(12)
C19 0.0352(15) 0.0312(15) 0.0308(15) -0.0051(11) -0.0044(12) -0.0017(12)
C20 0.0369(15) 0.0266(14) 0.0297(14) -0.0020(11) -0.0086(12) 0.0018(12)
C21 0.0452(17) 0.0259(14) 0.0342(15) -0.0078(11) -0.0108(13) 0.0029(12)
C22 0.0463(17) 0.0334(15) 0.0323(15) -0.0036(12) -0.0163(13) 0.0004(13)
C23 0.0372(15) 0.0269(14) 0.0367(15) -0.0019(12) -0.0117(12) 0.0020(12)
C24 0.0469(17) 0.0249(14) 0.0383(16) -0.0081(12) -0.0142(13) 0.0042(12)
C25 0.0428(16) 0.0260(14) 0.0314(15) -0.0039(11) -0.0148(12) 0.0016(12)
C26 0.0493(19) 0.0332(16) 0.0428(18) -0.0039(13) -0.0188(15) 0.0052(14)
C27 0.0363(15) 0.0303(14) 0.0289(14) 0.0012(11) -0.0062(12) 0.0075(12)
C28 0.0441(17) 0.0342(16) 0.0367(16) -0.0046(13) -0.0048(13) 0.0033(13)
C29 0.055(2) 0.0433(18) 0.0333(16) -0.0080(14) -0.0053(14) 0.0109(16)
C30 0.0419(17) 0.0429(18) 0.0335(16) 0.0077(13) -0.0002(13) 0.0101(14)
C31 0.0465(18) 0.0444(18) 0.0380(17) 0.0067(14) -0.0043(14) -0.0057(15)
C32 0.0436(17) 0.0421(17) 0.0300(15) 0.0027(13) -0.0051(13) -0.0028(14)
C33 0.076(3) 0.059(2) 0.0367(19) 0.0024(17) 0.0048(18) 0.013(2)
C41 0.0518(18) 0.0267(14) 0.0298(15) -0.0033(11) -0.0028(13) 0.0021(13)
C42 0.052(2) 0.0387(17) 0.0370(17) 0.0003(13) -0.0003(14) -0.0007(15)
C43 0.062(2) 0.0412(19) 0.047(2) 0.0035(15) 0.0119(17) 0.0036(16)
C44 0.089(3) 0.0309(17) 0.0338(18) 0.0016(13) 0.0055(18) 0.0050(17)
C45 0.096(3) 0.062(2) 0.0340(19) -0.0083(17) -0.014(2) -0.004(2)
C46 0.068(2) 0.058(2) 0.0381(19) -0.0073(16) -0.0104(17) -0.0058(18)
C47 0.116(4) 0.047(2) 0.038(2) -0.0009(17) 0.007(2) 0.007(2)
F1 0.0631(14) 0.0543(13) 0.0834(16) 0.0321(12) -0.0187(12) 0.0072(11)
F2 0.0462(11) 0.0529(11) 0.0568(12) -0.0144(9) -0.0234(9) 0.0135(9)
F3 0.0821(15) 0.0458(11) 0.0807(15) -0.0314(11) -0.0479(12) 0.0329(11)
F4 0.0835(19) 0.118(2) 0.0650(16) -0.0325(15) 0.0328(14) -0.0443(17)
F5 0.0669(14) 0.1069(19) 0.0321(11) -0.0089(11) -0.0009(10) -0.0033(13)
F6 0.191(4) 0.107(2) 0.0652(17) 0.0505(17) 0.052(2) 0.069(2)
C34 0.0312(15) 0.0275(14) 0.0317(15) -0.0017(11) -0.0069(12) 0.0027(11)
C35 0.041(2) 0.0308(16) 0.042(3) -0.0053(15) -0.016(2) -0.0004(14)
C36 0.048(2) 0.0417(19) 0.053(3) 0.0005(18) -0.027(2) 0.0017(17)
C37 0.0414(18) 0.0287(15) 0.059(2) 0.0007(14) -0.0176(16) 0.0042(13)
C38 0.039(3) 0.0256(15) 0.041(3) -0.0048(17) -0.0049(19) 0.0004(16)
C39 0.032(2) 0.0322(16) 0.034(2) -0.006(2) -0.0080(18) 0.0032(17)
C40 0.064(3) 0.032(2) 0.091(4) 0.003(2) -0.042(3) 0.0013(19)
F7 0.083(2) 0.0469(17) 0.129(3) 0.0403(19) -0.037(2) -0.0052(16)
F8 0.102(3) 0.0383(19) 0.135(4) 0.0020(19) -0.088(3) 0.0144(16)
F9 0.090(2) 0.0358(14) 0.116(3) -0.0130(16) -0.035(2) 0.0231(15)
C34B 0.0312(15) 0.0275(14) 0.0317(15) -0.0017(11) -0.0069(12) 0.0027(11)
C35B 0.041(2) 0.0308(16) 0.042(3) -0.0053(15) -0.016(2) -0.0004(14)
C36B 0.048(2) 0.0417(19) 0.053(3) 0.0005(18) -0.027(2) 0.0017(17)
C37B 0.0414(18) 0.0287(15) 0.059(2) 0.0007(14) -0.0176(16) 0.0042(13)
C38B 0.039(3) 0.0256(15) 0.041(3) -0.0048(17) -0.0049(19) 0.0004(16)
C39B 0.032(2) 0.0322(16) 0.034(2) -0.006(2) -0.0080(18) 0.0032(17)
C40B 0.064(3) 0.032(2) 0.091(4) 0.003(2) -0.042(3) 0.0013(19)
F7B 0.102(3) 0.0383(19) 0.135(4) 0.0020(19) -0.088(3) 0.0144(16)
F8B 0.083(2) 0.0469(17) 0.129(3) 0.0403(19) -0.037(2) -0.0052(16)
F9B 0.090(2) 0.0358(14) 0.116(3) -0.0130(16) -0.035(2) 0.0231(15)
F10 0.0958(18) 0.0623(14) 0.0412(12) -0.0068(10) 0.0148(11) 0.0082(12)
F11 0.247(4) 0.0664(17) 0.0508(15) -0.0104(12) 0.052(2) -0.065(2)
F12 0.147(3) 0.109(2) 0.0369(13) 0.0049(13) -0.0043(15) 0.033(2)
N1 0.0363(13) 0.0229(11) 0.0288(12) -0.0026(9) -0.0074(10) 0.0014(9)
N2 0.0353(12) 0.0242(11) 0.0279(12) -0.0014(9) -0.0048(10) 0.0035(9)
N3 0.0331(12) 0.0254(11) 0.0278(12) -0.0017(9) -0.0045(10) 0.0026(9)
N4 0.0311(12) 0.0264(12) 0.0305(12) -0.0032(9) -0.0048(10) 0.0036(9)
O2 0.151(7) 0.122(5) 0.053(3) 0.016(3) -0.009(3) 0.038(4)
C48 0.068(6) 0.106(5) 0.107(5) -0.005(4) -0.023(4) -0.011(5)
C49 0.074(4) 0.102(6) 0.086(5) 0.017(4) -0.013(4) -0.002(4)
O2B 0.151(7) 0.122(5) 0.053(3) 0.016(3) -0.009(3) 0.038(4)
C48B 0.068(6) 0.106(5) 0.107(5) -0.005(4) -0.023(4) -0.011(5)
C49B 0.074(4) 0.102(6) 0.086(5) 0.017(4) -0.013(4) -0.002(4)
O3 0.098(3) 0.087(3) 0.069(3) 0.006(2) -0.015(3) 0.021(3)
C50 0.068(4) 0.089(4) 0.075(5) 0.039(4) -0.019(4) -0.024(3)
C51 0.113(5) 0.045(5) 0.137(6) 0.013(5) -0.046(4) -0.014(5)
O3B 0.098(3) 0.087(3) 0.069(3) 0.006(2) -0.015(3) 0.021(3)
C50B 0.068(4) 0.089(4) 0.075(5) 0.039(4) -0.019(4) -0.024(3)
C51B 0.113(5) 0.045(5) 0.137(6) 0.013(5) -0.046(4) -0.014(5)
_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 1.364(4) . ?
C1 C19 1.401(4) . ?
C1 N5B 1.44(2) . ?
C1 C2 1.456(13) . ?
C2 O1 1.273(11) . ?
C2 N5 1.366(7) . ?
N5 N6 1.366(10) . ?
N5 C3 1.432(10) . ?
N6 H6A 0.916(19) . ?
N6 H6B 0.919(19) . ?
O1 H6C 1.08(7) . ?
O1 H6D 1.11(7) . ?
C2B O1B 1.28(2) . ?
C2B N5B 1.369(14) . ?
C2B C3 1.46(3) . ?
N5B N6B 1.38(2) . ?
N6B H6C 0.92(2) . ?
N6B H6D 0.91(2) . ?
O1B H6A 1.25(3) . ?
O1B H6B 0.97(5) . ?
C3 N1 1.352(3) . ?
C3 C4 1.400(4) . ?
C4 C5 1.394(4) . ?
C4 C20 1.496(4) . ?
C5 N2 1.376(3) . ?
C5 C6 1.432(4) . ?
C6 C7 1.366(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.423(4) . ?
C7 H7 0.9500 . ?
C8 N2 1.371(3) . ?
C8 C9 1.406(4) . ?
C9 C10 1.398(4) . ?
C9 C27 1.493(4) . ?
C10 N3 1.354(4) . ?
C10 C11 1.512(4) . ?
C11 C12 1.506(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.513(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N3 1.362(3) . ?
C13 C14 1.395(4) . ?
C14 C15 1.406(4) . ?
C14 C34B 1.477(9) . ?
C14 C34 1.514(3) . ?
C15 N4 1.376(3) . ?
C15 C16 1.426(4) . ?
C16 C17 1.363(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.428(4) . ?
C17 H17 0.9500 . ?
C18 N4 1.374(4) . ?
C18 C19 1.405(4) . ?
C19 C41 1.500(4) . ?
C20 C25 1.386(4) . ?
C20 C21 1.392(4) . ?
C21 C22 1.374(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(4) . ?
C23 C26 1.481(4) . ?
C24 C25 1.382(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 F1 1.337(4) . ?
C26 F3 1.338(4) . ?
C26 F2 1.339(4) . ?
C27 C32 1.388(4) . ?
C27 C28 1.392(4) . ?
C28 C29 1.395(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.377(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(5) . ?
C30 C33 1.501(5) . ?
C31 C32 1.389(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 F6 1.320(4) . ?
C33 F5 1.330(5) . ?
C33 F4 1.333(5) . ?
C41 C42 1.380(5) . ?
C41 C46 1.398(5) . ?
C42 C43 1.400(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.379(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.376(6) . ?
C44 C47 1.502(5) . ?
C45 C46 1.383(5) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 F11 1.285(5) . ?
C47 F10 1.330(5) . ?
C47 F12 1.368(6) . ?
C34 C35 1.3900 . ?
C34 C39 1.3900 . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 C37 1.3900 . ?
C36 H36 0.9500 . ?
C37 C38 1.3900 . ?
C37 C40 1.498(5) . ?
C38 C39 1.3900 . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 F8 1.322(5) . ?
C40 F7 1.327(6) . ?
C40 F9 1.352(6) . ?
C34B C35B 1.3900 . ?
C34B C39B 1.3900 . ?
C35B C36B 1.3900 . ?
C35B H35B 0.9500 . ?
C36B C37B 1.3900 . ?
C36B H36B 0.9500 . ?
C37B C38B 1.3900 . ?
C37B C40B 1.491(16) . ?
C38B C39B 1.3900 . ?
C38B H38B 0.9500 . ?
C39B H39B 0.9500 . ?
C40B F7B 1.322(14) . ?
C40B F8B 1.325(14) . ?
C40B F9B 1.329(14) . ?
N2 H2 0.8800 . ?
N4 H4 0.8800 . ?
O2 C48 1.399(8) . ?
O2 H2A 0.8400 . ?
C48 C49 1.436(10) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
O2B C48B 1.428(14) . ?
O2B H2B 0.8400 . ?
C48B C49B 1.456(14) . ?
C48B H48C 0.9900 . ?
C48B H48D 0.9900 . ?
C49B H49D 0.9800 . ?
C49B H49E 0.9800 . ?
C49B H49F 0.9800 . ?
O3 C50 1.443(8) . ?
O3 H3 0.8400 . ?
C50 C51 1.462(9) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
O3B C50B 1.531(12) . ?
O3B H3B 0.8400 . ?
C50B C51B 1.476(13) . ?
C50B H50C 0.9900 . ?
C50B H50D 0.9900 . ?
C51B H51D 0.9800 . ?
C51B H51E 0.9800 . ?
C51B H51F 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
N1 C1 C19 126.6(2) . . ?
N1 C1 N5B 109.1(10) . . ?
C19 C1 N5B 124.2(11) . . ?
N1 C1 C2 110.2(6) . . ?
C19 C1 C2 123.2(5) . . ?
O1 C2 N5 127.0(14) . . ?
O1 C2 C1 127.6(12) . . ?
N5 C2 C1 104.6(9) . . ?
N6 N5 C2 119.8(11) . . ?
N6 N5 C3 130.1(8) . . ?
C2 N5 C3 108.4(8) . . ?
N5 N6 H6A 115(3) . . ?
N5 N6 H6B 122(3) . . ?
H6A N6 H6B 98(2) . . ?
O1B C2B N5B 136(3) . . ?
O1B C2B C3 119(3) . . ?
N5B C2B C3 104.4(19) . . ?
C2B N5B N6B 115(3) . . ?
C2B N5B C1 108(2) . . ?
N6B N5B C1 136(3) . . ?
N5B N6B H6C 112(7) . . ?
N5B N6B H6D 113(7) . . ?
H6C N6B H6D 97(3) . . ?
N1 C3 C4 126.9(2) . . ?
N1 C3 N5 109.4(5) . . ?
C4 C3 N5 123.7(4) . . ?
N1 C3 C2B 110.7(11) . . ?
C4 C3 C2B 122.4(11) . . ?
C5 C4 C3 124.1(2) . . ?
C5 C4 C20 116.3(2) . . ?
C3 C4 C20 119.6(2) . . ?
N2 C5 C4 126.8(3) . . ?
N2 C5 C6 106.4(2) . . ?
C4 C5 C6 126.8(2) . . ?
C7 C6 C5 108.1(3) . . ?
C7 C6 H6 126.0 . . ?
C5 C6 H6 126.0 . . ?
C6 C7 C8 108.2(3) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
N2 C8 C9 127.4(2) . . ?
N2 C8 C7 106.8(2) . . ?
C9 C8 C7 125.7(3) . . ?
C10 C9 C8 126.3(3) . . ?
C10 C9 C27 118.0(2) . . ?
C8 C9 C27 115.7(2) . . ?
N3 C10 C9 126.1(2) . . ?
N3 C10 C11 112.7(2) . . ?
C9 C10 C11 121.1(3) . . ?
C12 C11 C10 103.0(2) . . ?
C12 C11 H11A 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C12 C11 H11B 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C11 C12 C13 103.5(2) . . ?
C11 C12 H12A 111.1 . . ?
C13 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
C13 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
N3 C13 C14 126.2(2) . . ?
N3 C13 C12 112.1(2) . . ?
C14 C13 C12 121.7(2) . . ?
C13 C14 C15 126.3(2) . . ?
C13 C14 C34B 115.1(7) . . ?
C15 C14 C34B 118.5(7) . . ?
C13 C14 C34 116.8(3) . . ?
C15 C14 C34 116.8(3) . . ?
N4 C15 C14 126.6(2) . . ?
N4 C15 C16 106.5(2) . . ?
C14 C15 C16 126.9(2) . . ?
C17 C16 C15 108.1(2) . . ?
C17 C16 H16 125.9 . . ?
C15 C16 H16 125.9 . . ?
C16 C17 C18 108.6(2) . . ?
C16 C17 H17 125.7 . . ?
C18 C17 H17 125.7 . . ?
N4 C18 C19 126.9(2) . . ?
N4 C18 C17 106.1(2) . . ?
C19 C18 C17 126.9(3) . . ?
C1 C19 C18 124.7(3) . . ?
C1 C19 C41 118.0(2) . . ?
C18 C19 C41 117.2(2) . . ?
C25 C20 C21 118.9(2) . . ?
C25 C20 C4 121.1(2) . . ?
C21 C20 C4 120.0(2) . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 C26 121.0(3) . . ?
C22 C23 C26 119.2(3) . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C20 120.9(3) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
F1 C26 F3 107.0(3) . . ?
F1 C26 F2 105.1(2) . . ?
F3 C26 F2 104.8(3) . . ?
F1 C26 C23 112.3(3) . . ?
F3 C26 C23 113.9(2) . . ?
F2 C26 C23 113.0(3) . . ?
C32 C27 C28 119.3(3) . . ?
C32 C27 C9 120.8(3) . . ?
C28 C27 C9 120.0(3) . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 120.7(3) . . ?
C29 C30 C33 121.4(3) . . ?
C31 C30 C33 117.8(3) . . ?
C30 C31 C32 119.4(3) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
C27 C32 C31 120.7(3) . . ?
C27 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
F6 C33 F5 106.8(3) . . ?
F6 C33 F4 105.8(4) . . ?
F5 C33 F4 106.0(3) . . ?
F6 C33 C30 111.6(3) . . ?
F5 C33 C30 113.4(4) . . ?
F4 C33 C30 112.8(3) . . ?
C42 C41 C46 118.9(3) . . ?
C42 C41 C19 121.7(3) . . ?
C46 C41 C19 119.4(3) . . ?
C41 C42 C43 120.0(3) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C44 C43 C42 120.2(4) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C45 C44 C43 120.2(3) . . ?
C45 C44 C47 121.3(4) . . ?
C43 C44 C47 118.5(4) . . ?
C44 C45 C46 119.7(4) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C45 C46 C41 121.0(4) . . ?
C45 C46 H46 119.5 . . ?
C41 C46 H46 119.5 . . ?
F11 C47 F10 107.9(4) . . ?
F11 C47 F12 105.7(4) . . ?
F10 C47 F12 104.7(3) . . ?
F11 C47 C44 113.9(4) . . ?
F10 C47 C44 112.7(3) . . ?
F12 C47 C44 111.4(4) . . ?
C35 C34 C39 120.0 . . ?
C35 C34 C14 119.9(4) . . ?
C39 C34 C14 119.8(4) . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 C36 120.0 . . ?
C38 C37 C40 116.6(4) . . ?
C36 C37 C40 123.4(4) . . ?
C37 C38 C39 120.0 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C39 C34 120.0 . . ?
C38 C39 H39 120.0 . . ?
C34 C39 H39 120.0 . . ?
F8 C40 F7 108.5(4) . . ?
F8 C40 F9 105.1(4) . . ?
F7 C40 F9 104.2(4) . . ?
F8 C40 C37 113.2(4) . . ?
F7 C40 C37 112.4(4) . . ?
F9 C40 C37 112.8(4) . . ?
C35B C34B C39B 120.0 . . ?
C35B C34B C14 122(2) . . ?
C39B C34B C14 118(2) . . ?
C36B C35B C34B 120.0 . . ?
C36B C35B H35B 120.0 . . ?
C34B C35B H35B 120.0 . . ?
C35B C36B C37B 120.0 . . ?
C35B C36B H36B 120.0 . . ?
C37B C36B H36B 120.0 . . ?
C36B C37B C38B 120.0 . . ?
C36B C37B C40B 113.8(15) . . ?
C38B C37B C40B 125.4(15) . . ?
C37B C38B C39B 120.0 . . ?
C37B C38B H38B 120.0 . . ?
C39B C38B H38B 120.0 . . ?
C38B C39B C34B 120.0 . . ?
C38B C39B H39B 120.0 . . ?
C34B C39B H39B 120.0 . . ?
F7B C40B F8B 106.6(13) . . ?
F7B C40B F9B 107.1(13) . . ?
F8B C40B F9B 106.0(13) . . ?
F7B C40B C37B 110.2(12) . . ?
F8B C40B C37B 112.0(13) . . ?
F9B C40B C37B 114.4(13) . . ?
C3 N1 C1 107.3(2) . . ?
C8 N2 C5 110.4(2) . . ?
C8 N2 H2 124.8 . . ?
C5 N2 H2 124.8 . . ?
C10 N3 C13 108.4(2) . . ?
C18 N4 C15 110.7(2) . . ?
C18 N4 H4 124.7 . . ?
C15 N4 H4 124.7 . . ?
O2 C48 C49 112.7(7) . . ?
O2 C48 H48A 109.0 . . ?
C49 C48 H48A 109.0 . . ?
O2 C48 H48B 109.0 . . ?
C49 C48 H48B 109.0 . . ?
H48A C48 H48B 107.8 . . ?
C48B O2B H2B 109.5 . . ?
O2B C48B C49B 109.0(15) . . ?
O2B C48B H48C 109.9 . . ?
C49B C48B H48C 109.9 . . ?
O2B C48B H48D 109.9 . . ?
C49B C48B H48D 109.9 . . ?
H48C C48B H48D 108.3 . . ?
C48B C49B H49D 109.5 . . ?
C48B C49B H49E 109.5 . . ?
H49D C49B H49E 109.5 . . ?
C48B C49B H49F 109.5 . . ?
H49D C49B H49F 109.5 . . ?
H49E C49B H49F 109.5 . . ?
O3 C50 C51 106.7(6) . . ?
O3 C50 H50A 110.4 . . ?
C51 C50 H50A 110.4 . . ?
O3 C50 H50B 110.4 . . ?
C51 C50 H50B 110.4 . . ?
H50A C50 H50B 108.6 . . ?
C50B O3B H3B 109.5 . . ?
C51B C50B O3B 100.0(15) . . ?
C51B C50B H50C 111.8 . . ?
O3B C50B H50C 111.8 . . ?
C51B C50B H50D 111.8 . . ?
O3B C50B H50D 111.8 . . ?
H50C C50B H50D 109.5 . . ?
C50B C51B H51D 109.5 . . ?
C50B C51B H51E 109.5 . . ?
H51D C51B H51E 109.5 . . ?
C50B C51B H51F 109.5 . . ?
H51D C51B H51F 109.5 . . ?
H51E C51B H51F 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
N1 C1 C2 O1 -167.9(8) . . . . ?
C19 C1 C2 O1 14.7(12) . . . . ?
N5B C1 C2 O1 -175(100) . . . . ?
N1 C1 C2 N5 2.5(8) . . . . ?
C19 C1 C2 N5 -174.9(5) . . . . ?
N5B C1 C2 N5 -4(94) . . . . ?
O1 C2 N5 N6 2.7(12) . . . . ?
C1 C2 N5 N6 -167.8(9) . . . . ?
O1 C2 N5 C3 169.7(10) . . . . ?
C1 C2 N5 C3 -0.7(8) . . . . ?
O1B C2B N5B N6B 0(4) . . . . ?
C3 C2B N5B N6B 174(2) . . . . ?
O1B C2B N5B C1 -175(3) . . . . ?
C3 C2B N5B C1 -0.6(18) . . . . ?
N1 C1 N5B C2B 2.4(16) . . . . ?
C19 C1 N5B C2B -174.9(12) . . . . ?
C2 C1 N5B C2B 176(100) . . . . ?
N1 C1 N5B N6B -171(3) . . . . ?
C19 C1 N5B N6B 12(3) . . . . ?
C2 C1 N5B N6B 3(94) . . . . ?
N6 N5 C3 N1 164.0(8) . . . . ?
C2 N5 C3 N1 -1.3(7) . . . . ?
N6 N5 C3 C4 -18.7(12) . . . . ?
C2 N5 C3 C4 176.0(5) . . . . ?
N6 N5 C3 C2B -16(79) . . . . ?
C2 N5 C3 C2B 178(100) . . . . ?
O1B C2B C3 N1 173.9(19) . . . . ?
N5B C2B C3 N1 -1.3(18) . . . . ?
O1B C2B C3 C4 -9(3) . . . . ?
N5B C2B C3 C4 176.0(10) . . . . ?
O1B C2B C3 N5 174(81) . . . . ?
N5B C2B C3 N5 -2(78) . . . . ?
N1 C3 C4 C5 -10.1(5) . . . . ?
N5 C3 C4 C5 173.0(6) . . . . ?
C2B C3 C4 C5 173.0(16) . . . . ?
N1 C3 C4 C20 166.3(3) . . . . ?
N5 C3 C4 C20 -10.5(7) . . . . ?
C2B C3 C4 C20 -10.6(16) . . . . ?
C3 C4 C5 N2 -2.7(5) . . . . ?
C20 C4 C5 N2 -179.2(3) . . . . ?
C3 C4 C5 C6 177.5(3) . . . . ?
C20 C4 C5 C6 1.0(4) . . . . ?
N2 C5 C6 C7 -1.1(3) . . . . ?
C4 C5 C6 C7 178.7(3) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C6 C7 C8 N2 -1.4(3) . . . . ?
C6 C7 C8 C9 176.7(3) . . . . ?
N2 C8 C9 C10 3.7(5) . . . . ?
C7 C8 C9 C10 -174.1(3) . . . . ?
N2 C8 C9 C27 -177.1(3) . . . . ?
C7 C8 C9 C27 5.1(4) . . . . ?
C8 C9 C10 N3 -0.6(5) . . . . ?
C27 C9 C10 N3 -179.8(3) . . . . ?
C8 C9 C10 C11 178.8(3) . . . . ?
C27 C9 C10 C11 -0.4(4) . . . . ?
N3 C10 C11 C12 -3.4(3) . . . . ?
C9 C10 C11 C12 177.2(3) . . . . ?
C10 C11 C12 C13 4.6(3) . . . . ?
C11 C12 C13 N3 -4.8(3) . . . . ?
C11 C12 C13 C14 173.2(3) . . . . ?
N3 C13 C14 C15 0.9(5) . . . . ?
C12 C13 C14 C15 -176.9(3) . . . . ?
N3 C13 C14 C34B 177.1(16) . . . . ?
C12 C13 C14 C34B -0.6(16) . . . . ?
N3 C13 C14 C34 176.7(4) . . . . ?
C12 C13 C14 C34 -1.0(5) . . . . ?
C13 C14 C15 N4 -9.4(5) . . . . ?
C34B C14 C15 N4 174.4(16) . . . . ?
C34 C14 C15 N4 174.7(4) . . . . ?
C13 C14 C15 C16 167.6(3) . . . . ?
C34B C14 C15 C16 -8.5(16) . . . . ?
C34 C14 C15 C16 -8.2(5) . . . . ?
N4 C15 C16 C17 0.7(3) . . . . ?
C14 C15 C16 C17 -176.9(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 N4 1.2(3) . . . . ?
C16 C17 C18 C19 -177.8(3) . . . . ?
N1 C1 C19 C18 10.9(5) . . . . ?
N5B C1 C19 C18 -172.3(15) . . . . ?
C2 C1 C19 C18 -172.1(7) . . . . ?
N1 C1 C19 C41 -165.5(3) . . . . ?
N5B C1 C19 C41 11.2(15) . . . . ?
C2 C1 C19 C41 11.4(8) . . . . ?
N4 C18 C19 C1 5.6(5) . . . . ?
C17 C18 C19 C1 -175.5(3) . . . . ?
N4 C18 C19 C41 -177.9(3) . . . . ?
C17 C18 C19 C41 1.0(4) . . . . ?
C5 C4 C20 C25 -66.1(4) . . . . ?
C3 C4 C20 C25 117.2(3) . . . . ?
C5 C4 C20 C21 112.3(3) . . . . ?
C3 C4 C20 C21 -64.4(4) . . . . ?
C25 C20 C21 C22 -0.5(5) . . . . ?
C4 C20 C21 C22 -179.0(3) . . . . ?
C20 C21 C22 C23 0.6(5) . . . . ?
C21 C22 C23 C24 -0.5(5) . . . . ?
C21 C22 C23 C26 -178.3(3) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C26 C23 C24 C25 178.1(3) . . . . ?
C23 C24 C25 C20 -0.4(5) . . . . ?
C21 C20 C25 C24 0.4(4) . . . . ?
C4 C20 C25 C24 178.9(3) . . . . ?
C24 C23 C26 F1 -105.5(3) . . . . ?
C22 C23 C26 F1 72.2(4) . . . . ?
C24 C23 C26 F3 16.3(4) . . . . ?
C22 C23 C26 F3 -166.0(3) . . . . ?
C24 C23 C26 F2 135.8(3) . . . . ?
C22 C23 C26 F2 -46.5(4) . . . . ?
C10 C9 C27 C32 77.0(4) . . . . ?
C8 C9 C27 C32 -102.3(3) . . . . ?
C10 C9 C27 C28 -103.5(3) . . . . ?
C8 C9 C27 C28 77.2(3) . . . . ?
C32 C27 C28 C29 -1.9(4) . . . . ?
C9 C27 C28 C29 178.6(3) . . . . ?
C27 C28 C29 C30 1.0(4) . . . . ?
C28 C29 C30 C31 0.6(5) . . . . ?
C28 C29 C30 C33 -176.2(3) . . . . ?
C29 C30 C31 C32 -1.4(5) . . . . ?
C33 C30 C31 C32 175.6(3) . . . . ?
C28 C27 C32 C31 1.1(4) . . . . ?
C9 C27 C32 C31 -179.4(3) . . . . ?
C30 C31 C32 C27 0.5(5) . . . . ?
C29 C30 C33 F6 103.2(5) . . . . ?
C31 C30 C33 F6 -73.7(5) . . . . ?
C29 C30 C33 F5 -17.4(5) . . . . ?
C31 C30 C33 F5 165.7(3) . . . . ?
C29 C30 C33 F4 -137.8(3) . . . . ?
C31 C30 C33 F4 45.3(4) . . . . ?
C1 C19 C41 C42 -114.5(3) . . . . ?
C18 C19 C41 C42 68.8(4) . . . . ?
C1 C19 C41 C46 64.5(4) . . . . ?
C18 C19 C41 C46 -112.2(3) . . . . ?
C46 C41 C42 C43 0.5(5) . . . . ?
C19 C41 C42 C43 179.5(3) . . . . ?
C41 C42 C43 C44 0.4(5) . . . . ?
C42 C43 C44 C45 -1.1(5) . . . . ?
C42 C43 C44 C47 178.7(3) . . . . ?
C43 C44 C45 C46 0.8(6) . . . . ?
C47 C44 C45 C46 -179.0(3) . . . . ?
C44 C45 C46 C41 0.1(6) . . . . ?
C42 C41 C46 C45 -0.8(5) . . . . ?
C19 C41 C46 C45 -179.8(3) . . . . ?
C45 C44 C47 F11 -128.9(5) . . . . ?
C43 C44 C47 F11 51.3(5) . . . . ?
C45 C44 C47 F10 107.8(5) . . . . ?
C43 C44 C47 F10 -72.0(5) . . . . ?
C45 C44 C47 F12 -9.5(5) . . . . ?
C43 C44 C47 F12 170.7(3) . . . . ?
C13 C14 C34 C35 76.1(4) . . . . ?
C15 C14 C34 C35 -107.6(3) . . . . ?
C34B C14 C34 C35 64(54) . . . . ?
C13 C14 C34 C39 -97.5(3) . . . . ?
C15 C14 C34 C39 78.7(4) . . . . ?
C34B C14 C34 C39 -110(55) . . . . ?
C39 C34 C35 C36 0.0 . . . . ?
C14 C34 C35 C36 -173.7(3) . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C35 C36 C37 C40 177.0(4) . . . . ?
C36 C37 C38 C39 0.0 . . . . ?
C40 C37 C38 C39 -177.2(4) . . . . ?
C37 C38 C39 C34 0.0 . . . . ?
C35 C34 C39 C38 0.0 . . . . ?
C14 C34 C39 C38 173.7(3) . . . . ?
C38 C37 C40 F8 -173.8(4) . . . . ?
C36 C37 C40 F8 9.1(6) . . . . ?
C38 C37 C40 F7 62.8(5) . . . . ?
C36 C37 C40 F7 -114.3(4) . . . . ?
C38 C37 C40 F9 -54.6(5) . . . . ?
C36 C37 C40 F9 128.3(3) . . . . ?
C13 C14 C34B C35B 91.9(13) . . . . ?
C15 C14 C34B C35B -91.5(13) . . . . ?
C34 C14 C34B C35B -100(55) . . . . ?
C13 C14 C34B C39B -83.0(14) . . . . ?
C15 C14 C34B C39B 93.5(13) . . . . ?
C34 C14 C34B C39B 85(55) . . . . ?
C39B C34B C35B C36B 0.0 . . . . ?
C14 C34B C35B C36B -174.8(13) . . . . ?
C34B C35B C36B C37B 0.0 . . . . ?
C35B C36B C37B C38B 0.0 . . . . ?
C35B C36B C37B C40B 170.5(15) . . . . ?
C36B C37B C38B C39B 0.0 . . . . ?
C40B C37B C38B C39B -169.3(17) . . . . ?
C37B C38B C39B C34B 0.0 . . . . ?
C35B C34B C39B C38B 0.0 . . . . ?
C14 C34B C39B C38B 175.0(13) . . . . ?
C36B C37B C40B F7B 155.5(14) . . . . ?
C38B C37B C40B F7B -35(2) . . . . ?
C36B C37B C40B F8B 37.0(17) . . . . ?
C38B C37B C40B F8B -153.2(17) . . . . ?
C36B C37B C40B F9B -83.7(15) . . . . ?
C38B C37B C40B F9B 86.2(19) . . . . ?
C4 C3 N1 C1 -174.4(3) . . . . ?
N5 C3 N1 C1 2.8(5) . . . . ?
C2B C3 N1 C1 2.8(14) . . . . ?
C19 C1 N1 C3 174.0(3) . . . . ?
N5B C1 N1 C3 -3.2(13) . . . . ?
C2 C1 N1 C3 -3.3(6) . . . . ?
C9 C8 N2 C5 -177.4(3) . . . . ?
C7 C8 N2 C5 0.7(3) . . . . ?
C4 C5 N2 C8 -179.6(3) . . . . ?
C6 C5 N2 C8 0.2(3) . . . . ?
C9 C10 N3 C13 179.8(3) . . . . ?
C11 C10 N3 C13 0.4(3) . . . . ?
C14 C13 N3 C10 -175.1(3) . . . . ?
C12 C13 N3 C10 2.8(3) . . . . ?
C19 C18 N4 C15 178.3(3) . . . . ?
C17 C18 N4 C15 -0.8(3) . . . . ?
C14 C15 N4 C18 177.6(3) . . . . ?
C16 C15 N4 C18 0.1(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3B H3B O2B 0.84 1.92 2.70(2) 155.7 .
O3 H3 O1 0.84 2.02 2.855(9) 173.3 .
O2B H2B O1B 0.84 2.18 2.96(3) 156.1 .
O2 H2A O3 0.84 1.91 2.657(8) 147.4 .
N4 H4 N3 0.88 2.43 2.961(3) 118.8 .
N4 H4 N1 0.88 2.41 2.948(3) 119.5 .
N2 H2 N3 0.88 2.44 2.972(3) 119.0 .
N2 H2 N1 0.88 2.36 2.906(3) 120.0 .
N6B H6D O3B 0.91(2) 2.13(8) 2.83(4) 133(8) .
N6 H6B O2 0.919(19) 1.95(3) 2.769(13) 148(3) .
N6 H6A N3 0.916(19) 2.46(3) 3.250(12) 144(3) 2_566
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.061


data_12mz109_0m
_database_code_depnum_ccdc_archive 'CCDC 919813'
#TrackingRef '16864_web_deposit_cif_file_3_ChristianBrueckner_1358220260.JA-D-202F1-B_12mz109_0m(15a).cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H28 Cl N5'
_chemical_formula_weight         650.15
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   14.440(4)
_cell_length_b                   16.901(5)
_cell_length_c                   14.820(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.629(4)
_cell_angle_gamma                90.00
_cell_volume                     3204.4(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    937
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      23.80
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5716
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Apex2 v2011.2-0 (Bruker, 2011)'
_exptl_special_details           
;
The chloro-imidazole unit is disordered within the macrocycle over all
eight possible positions. Occupancy ratios refined to 0.121(2), 0.223(3),
0.040(2), 0.100(2), 0.060(2), 0.378(2), 0.032(1) and 0.0446(2). Positions
and ADPs of overlapping C and N atoms were not refined but constrained
to be each identical. The positions and ADPs of the two chlorine atoms
with the highest occupancy (22.3 and 37.8%) were freely refined. For the
other Cl atoms C-Cl bond distances were restrained to be 1.7 Ansgtroms,
and ADPs were restrained to be similar to that of the C atom they are
bonded to (DELU command in Shelxtl, for one Cl position an additional
SIMU restraint was applied).
Interaction of the Cl atoms with neighboring molecules induces visible
disorder of two of the four phenyl rings. One of the rings, with an
occupancy ratio of 0.67(2) to 0.33(2), one of the rings was constrained
to resemble an ideal hexagon with C-C distances of 1.39 Angstrom, and
the other was restrained to have a geometry similar to that of the first.
Substantially overlapping C atoms (the ipso and para atoms) were each
constrained to have identical ADPs. The C-macrocycle to C-ipso bond
distances were restrained to be similar.
For the other disordered phenyl ring the minor moiety is tied to a minor
occupied Cl atom in a neighboring molecule, and they were set to have
identical occupancies. This minor occupied phenyl ring was restrained to
have a similar geometry as its major occupied counterpart, and ADPs of all
equivalent atoms were constrained to be identical.
Occupancies of the N-H hydrogen atoms were set so that none of the
chloro-imidazole units are protonated, and that opposing pyrrole units
are protonated.
;
_diffrn_ambient_temperature      100(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  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16647
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_sigmaI/netI    0.1536
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         28.29
_reflns_number_total             7763
_reflns_number_gt                3130
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'Apex2 v2011.2-0 (Bruker, 2011)'
_computing_cell_refinement       'Apex2 v2011.2-0'
_computing_data_reduction        'Apex2 v2011.2-0'
_computing_structure_solution    'SHELXTL 6.14 (Bruker, 2003; Sheldrick, 2008)'
_computing_structure_refinement  
;
SHELXLE Rev548, Shelxle (H\"ubschle et al., 2011)
;
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_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^)+(0.0808P)^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       0.0018(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         7763
_refine_ls_number_parameters     563
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.1966
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2002
_refine_ls_wR_factor_gt          0.1599
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.983
_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
C1 C 0.8510(3) 0.61499(17) 0.1657(2) 0.0384(8) Uani 1 1 d . . .
C2 C 0.9268(3) 0.60711(18) 0.1300(2) 0.0468(8) Uani 0.655(3) 1 d P A 1
H2 H 1.0006 0.6103 0.1694 0.056 Uiso 0.655(3) 1 calc PR A 1
C3 C 0.8728(3) 0.59438(19) 0.0296(2) 0.0500(9) Uani 0.655(3) 1 d P A 1
H3 H 0.9017 0.5871 -0.0158 0.060 Uiso 0.655(3) 1 calc PR A 1
C4 C 0.7646(3) 0.59372(18) 0.0029(2) 0.0417(8) Uani 1 1 d . . .
C5 C 0.6830(3) 0.57970(18) -0.0962(2) 0.0436(8) Uani 1 1 d D A .
C6 C 0.5770(3) 0.58144(18) -0.1237(2) 0.0411(8) Uani 1 1 d . . .
C7 C 0.4934(3) 0.56511(18) -0.2218(2) 0.0530(9) Uani 0.859(2) 1 d P A 1
H7 H 0.4998 0.5497 -0.2803 0.064 Uiso 0.859(2) 1 calc PR A 1
C8 C 0.4041(3) 0.57537(19) -0.2168(2) 0.0536(10) Uani 0.859(2) 1 d P A 1
H8 H 0.3361 0.5683 -0.2719 0.064 Uiso 0.859(2) 1 calc PR A 1
C9 C 0.4262(3) 0.59836(17) -0.1169(2) 0.0405(8) Uani 1 1 d . . .
C10 C 0.3546(3) 0.61889(17) -0.0822(2) 0.0394(8) Uani 1 1 d . A .
C11 C 0.3823(3) 0.63539(17) 0.0212(2) 0.0409(8) Uani 1 1 d . . .
C12 C 0.3087(2) 0.66335(17) 0.0518(2) 0.0460(8) Uani 0.562(3) 1 d P A 1
H12 H 0.2370 0.6751 0.0096 0.055 Uiso 0.562(3) 1 calc PR A 1
C13 C 0.3626(3) 0.6696(2) 0.1534(2) 0.0488(9) Uani 0.562(3) 1 d P A 1
H13 H 0.3348 0.6871 0.1968 0.059 Uiso 0.562(3) 1 calc PR A 1
C14 C 0.4689(3) 0.64586(17) 0.1862(2) 0.0387(8) Uani 1 1 d . . .
C15 C 0.5485(3) 0.64657(17) 0.2872(2) 0.0384(8) Uani 1 1 d . A .
C16 C 0.6548(3) 0.63810(17) 0.3162(2) 0.0386(8) Uani 1 1 d . . .
C17 C 0.7391(3) 0.64645(19) 0.4163(2) 0.0460(9) Uani 0.923(3) 1 d P A 1
H17 H 0.7324 0.6542 0.4765 0.055 Uiso 0.923(3) 1 calc PR A 1
C18 C 0.8294(3) 0.64158(19) 0.4115(2) 0.0459(8) Uani 0.923(3) 1 d P A 1
H18 H 0.8974 0.6457 0.4675 0.055 Uiso 0.923(3) 1 calc PR A 1
C19 C 0.8054(3) 0.62901(17) 0.3073(2) 0.0393(8) Uani 1 1 d . . .
C20 C 0.8776(2) 0.62469(17) 0.2695(2) 0.0376(8) Uani 1 1 d . A .
C21 C 0.7099(7) 0.5618(5) -0.1805(4) 0.0461(15) Uani 0.67(2) 1 d PGD A 10
C22 C 0.7678(8) 0.4953(5) -0.1777(6) 0.050(3) Uani 0.67(2) 1 d PGD A 10
H22 H 0.7890 0.4589 -0.1229 0.060 Uiso 0.67(2) 1 calc PR A 10
C23 C 0.7949(8) 0.4822(5) -0.2550(8) 0.070(4) Uani 0.67(2) 1 d PGD A 10
H23 H 0.8346 0.4368 -0.2531 0.084 Uiso 0.67(2) 1 calc PR A 10
C24 C 0.7641(7) 0.5355(6) -0.3352(6) 0.066(2) Uani 0.67(2) 1 d PGD A 10
H24 H 0.7826 0.5265 -0.3881 0.079 Uiso 0.67(2) 1 calc PR A 10
C25 C 0.7061(9) 0.6020(7) -0.3381(5) 0.071(3) Uani 0.67(2) 1 d PGD A 10
H25 H 0.6850 0.6384 -0.3929 0.085 Uiso 0.67(2) 1 calc PR A 10
C26 C 0.6790(8) 0.6151(6) -0.2607(6) 0.064(3) Uani 0.67(2) 1 d PGD A 10
H26 H 0.6393 0.6606 -0.2627 0.077 Uiso 0.67(2) 1 calc PR A 10
C21B C 0.7209(17) 0.5746(14) -0.1764(12) 0.0461(15) Uani 0.33(2) 1 d PD A 11
C22B C 0.733(3) 0.5023(14) -0.211(2) 0.084(9) Uani 0.33(2) 1 d PD A 11
H22B H 0.7182 0.4565 -0.1823 0.101 Uiso 0.33(2) 1 calc PR A 11
C23B C 0.765(3) 0.4919(11) -0.283(3) 0.071(7) Uani 0.33(2) 1 d PD A 11
H23B H 0.7808 0.4405 -0.2978 0.086 Uiso 0.33(2) 1 calc PR A 11
C24B C 0.7727(19) 0.5562(16) -0.3350(16) 0.066(2) Uani 0.33(2) 1 d PD A 11
H24B H 0.7826 0.5495 -0.3936 0.079 Uiso 0.33(2) 1 calc PR A 11
C25B C 0.767(3) 0.6293(12) -0.302(2) 0.088(8) Uani 0.33(2) 1 d PD A 11
H25B H 0.7805 0.6746 -0.3317 0.106 Uiso 0.33(2) 1 calc PR A 11
C26B C 0.740(3) 0.6374(11) -0.223(2) 0.085(8) Uani 0.33(2) 1 d PD A 11
H26B H 0.7340 0.6892 -0.2014 0.102 Uiso 0.33(2) 1 calc PR A 11
C27 C 0.2418(3) 0.62571(18) -0.1585(2) 0.0425(8) Uani 1 1 d . . .
C28 C 0.2113(3) 0.67526(18) -0.2419(2) 0.0474(9) Uani 1 1 d . A .
H28 H 0.2623 0.7049 -0.2510 0.057 Uiso 1 1 calc R . .
C29 C 0.1056(3) 0.6819(2) -0.3130(2) 0.0529(10) Uani 1 1 d . . .
H29 H 0.0854 0.7154 -0.3705 0.064 Uiso 1 1 calc R A .
C30 C 0.0310(3) 0.6405(2) -0.3000(3) 0.0575(10) Uani 1 1 d . A .
H30 H -0.0407 0.6459 -0.3477 0.069 Uiso 1 1 calc R . .
C31 C 0.0607(3) 0.5908(2) -0.2171(3) 0.0573(10) Uani 1 1 d . . .
H31 H 0.0094 0.5617 -0.2079 0.069 Uiso 1 1 calc R A .
C32 C 0.1654(3) 0.58353(19) -0.1473(3) 0.0509(9) Uani 1 1 d . A .
H32 H 0.1853 0.5490 -0.0907 0.061 Uiso 1 1 calc R . .
C33 C 0.5190(3) 0.6619(2) 0.3701(2) 0.0429(8) Uani 0.940(2) 1 d PD A 1
C34 C 0.4673(3) 0.6071(2) 0.3978(3) 0.0559(11) Uani 0.940(2) 1 d PD A 1
H34 H 0.4494 0.5575 0.3638 0.067 Uiso 0.940(2) 1 calc PR A 1
C35 C 0.4407(4) 0.6223(3) 0.4738(3) 0.0735(14) Uani 0.940(2) 1 d PD A 1
H35 H 0.4052 0.5832 0.4922 0.088 Uiso 0.940(2) 1 calc PR A 1
C36 C 0.4650(3) 0.6930(3) 0.5230(3) 0.0748(13) Uani 0.940(2) 1 d PD A 1
H36 H 0.4437 0.7039 0.5735 0.090 Uiso 0.940(2) 1 calc PR A 1
C37 C 0.5199(4) 0.7488(3) 0.5002(3) 0.0714(13) Uani 0.940(2) 1 d PD A 1
H37 H 0.5396 0.7972 0.5368 0.086 Uiso 0.940(2) 1 calc PR A 1
C38 C 0.5466(3) 0.7338(2) 0.4229(3) 0.0565(11) Uani 0.940(2) 1 d PD A 1
H38 H 0.5837 0.7725 0.4059 0.068 Uiso 0.940(2) 1 calc PR A 1
C33E C 0.5190(3) 0.6619(2) 0.3701(2) 0.0429(8) Uani 0.060(2) 1 d PD A 6
C34E C 0.532(5) 0.6048(18) 0.440(3) 0.0559(11) Uani 0.060(2) 1 d PD A 6
H34E H 0.5534 0.5528 0.4336 0.067 Uiso 0.060(2) 1 calc PR A 6
C35E C 0.513(5) 0.624(2) 0.520(3) 0.0735(14) Uani 0.060(2) 1 d PD A 6
H35E H 0.5349 0.5888 0.5753 0.088 Uiso 0.060(2) 1 calc PR A 6
C36E C 0.4650(3) 0.6930(3) 0.5230(3) 0.0748(13) Uani 0.060(2) 1 d PD A 6
H36E H 0.4463 0.7024 0.5757 0.090 Uiso 0.060(2) 1 calc PR A 6
C37E C 0.444(5) 0.748(2) 0.448(3) 0.0714(13) Uani 0.060(2) 1 d PD A 6
H37E H 0.4137 0.7978 0.4493 0.086 Uiso 0.060(2) 1 calc PR A 6
C38E C 0.468(5) 0.731(2) 0.369(3) 0.0565(11) Uani 0.060(2) 1 d PD A 6
H38E H 0.4483 0.7672 0.3141 0.068 Uiso 0.060(2) 1 calc PR A 6
C39 C 0.9906(3) 0.63000(17) 0.3463(2) 0.0370(8) Uani 1 1 d . . .
C40 C 1.0376(3) 0.56852(18) 0.4141(2) 0.0411(8) Uani 1 1 d . A .
H40 H 0.9986 0.5220 0.4093 0.049 Uiso 1 1 calc R . .
C41 C 1.1404(3) 0.5740(2) 0.4889(2) 0.0450(8) Uani 1 1 d . . .
H41 H 1.1717 0.5313 0.5348 0.054 Uiso 1 1 calc R A .
C42 C 1.1969(3) 0.6410(2) 0.4966(3) 0.0481(9) Uani 1 1 d . A .
H42 H 1.2671 0.6451 0.5486 0.058 Uiso 1 1 calc R . .
C43 C 1.1523(3) 0.7022(2) 0.4295(3) 0.0606(10) Uani 1 1 d . . .
H43 H 1.1921 0.7482 0.4344 0.073 Uiso 1 1 calc R A .
C44 C 1.0493(3) 0.6972(2) 0.3546(3) 0.0555(10) Uani 1 1 d . A .
H44 H 1.0187 0.7400 0.3086 0.067 Uiso 1 1 calc R . .
N1 N 0.7516(2) 0.60744(14) 0.08756(18) 0.0406(7) Uani 1 1 d . A .
H1A H 0.6924 0.6107 0.0909 0.049 Uiso 0.218(2) 1 calc PR . .
N2 N 0.5335(2) 0.59938(14) -0.06132(18) 0.0392(7) Uani 1 1 d . A .
H2A H 0.5687 0.6099 0.0042 0.047 Uiso 0.782(2) 1 calc PR . .
N3 N 0.4795(2) 0.62597(14) 0.10207(17) 0.0376(6) Uani 1 1 d . A .
H3A H 0.5368 0.6104 0.1003 0.045 Uiso 0.218(2) 1 calc PR . .
N4 N 0.6982(2) 0.62616(14) 0.25225(18) 0.0384(6) Uani 1 1 d . A .
H4A H 0.6629 0.6179 0.1862 0.046 Uiso 0.782(2) 1 calc PR . .
C2A C 0.9268(3) 0.60711(18) 0.1300(2) 0.0468(8) Uani 0.1213(18) 1 d PDU A 2
N1A N 0.8728(3) 0.59438(19) 0.0296(2) 0.0500(9) Uani 0.1213(18) 1 d P A 2
Cl1A Cl 1.0594(3) 0.6047(7) 0.1846(5) 0.091(3) Uani 0.1213(18) 1 d PDU A 2
N1B N 0.9268(3) 0.60711(18) 0.1300(2) 0.0468(8) Uani 0.223(3) 1 d P A 3
C3B C 0.8728(3) 0.59438(19) 0.0296(2) 0.0500(9) Uani 0.223(3) 1 d P A 3
Cl1B Cl 0.9530(3) 0.5672(3) -0.0243(3) 0.0605(16) Uani 0.223(3) 1 d P A 3
C7C C 0.4934(3) 0.56511(18) -0.2218(2) 0.0530(9) Uani 0.0409(17) 1 d PDU A 4
N1C N 0.4041(3) 0.57537(19) -0.2168(2) 0.0536(10) Uani 0.0409(17) 1 d P A 4
Cl1C Cl 0.458(2) 0.5385(14) -0.3440(7) 0.073(9) Uani 0.0409(17) 1 d PDU A 4
N1D N 0.4934(3) 0.56511(18) -0.2218(2) 0.0530(9) Uani 0.100(2) 1 d P A 5
C8D C 0.4041(3) 0.57537(19) -0.2168(2) 0.0536(10) Uani 0.100(2) 1 d PDU A 5
Cl1D Cl 0.3044(6) 0.5386(5) -0.3247(5) 0.065(3) Uani 0.100(2) 1 d PDU A 5
C12E C 0.3087(2) 0.66335(17) 0.0518(2) 0.0460(8) Uani 0.060(2) 1 d PDU A 6
N1E N 0.3626(3) 0.6696(2) 0.1534(2) 0.0488(9) Uani 0.060(2) 1 d P A 6
Cl1E Cl 0.1840(8) 0.6942(18) 0.014(2) 0.146(13) Uani 0.060(2) 1 d PDU A 6
N1F N 0.3087(2) 0.66335(17) 0.0518(2) 0.0460(8) Uani 0.378(2) 1 d P A 7
C13F C 0.3626(3) 0.6696(2) 0.1534(2) 0.0488(9) Uani 0.378(2) 1 d P A 7
Cl1F Cl 0.29800(18) 0.71258(15) 0.21258(16) 0.0599(9) Uani 0.378(2) 1 d P A 7
C17G C 0.7391(3) 0.64645(19) 0.4163(2) 0.0460(9) Uani 0.0323(15) 1 d PDU A 8
N1G N 0.8294(3) 0.64158(19) 0.4115(2) 0.0459(8) Uani 0.0323(15) 1 d P A 8
Cl1G Cl 0.746(2) 0.6206(14) 0.5299(10) 0.0460(14) Uani 0.0323(15) 1 d PDU A 8
N1H N 0.7391(3) 0.64645(19) 0.4163(2) 0.0460(9) Uani 0.045(2) 1 d P A 9
C18H C 0.8294(3) 0.64158(19) 0.4115(2) 0.0459(8) Uani 0.045(2) 1 d PDU A 9
Cl1H Cl 0.9404(11) 0.6660(14) 0.5181(11) 0.079(9) Uani 0.045(2) 1 d PDU A 9
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 0.042(2) 0.0377(18) 0.0395(18) 0.0009(14) 0.0226(17) -0.0016(15)
C2 0.057(2) 0.0484(19) 0.0487(19) 0.0001(16) 0.0364(18) -0.0015(16)
C3 0.064(3) 0.054(2) 0.049(2) -0.0065(16) 0.0403(19) -0.0133(18)
C4 0.050(2) 0.0409(19) 0.0402(18) -0.0001(14) 0.0264(17) 0.0020(16)
C5 0.056(3) 0.0417(19) 0.0361(18) 0.0023(14) 0.0238(18) 0.0034(17)
C6 0.050(2) 0.0412(19) 0.0323(17) 0.0020(14) 0.0193(17) 0.0059(16)
C7 0.075(3) 0.047(2) 0.0421(19) -0.0054(16) 0.032(2) 0.0009(19)
C8 0.072(3) 0.046(2) 0.0385(19) -0.0004(15) 0.0221(18) 0.0017(19)
C9 0.051(2) 0.0328(17) 0.0357(17) 0.0004(14) 0.0185(17) 0.0000(16)
C10 0.046(2) 0.0319(17) 0.0368(17) -0.0006(14) 0.0167(17) -0.0011(15)
C11 0.041(2) 0.0355(18) 0.0429(19) 0.0010(14) 0.0165(17) 0.0013(15)
C12 0.044(2) 0.0510(19) 0.0418(18) -0.0006(14) 0.0184(16) 0.0041(15)
C13 0.046(2) 0.056(2) 0.053(2) -0.0044(17) 0.0306(19) 0.0012(17)
C14 0.040(2) 0.0404(18) 0.0374(18) -0.0008(14) 0.0196(16) 0.0018(15)
C15 0.042(2) 0.0395(18) 0.0348(17) 0.0010(14) 0.0191(16) 0.0056(15)
C16 0.042(2) 0.0438(19) 0.0317(17) -0.0015(14) 0.0188(16) 0.0027(15)
C17 0.050(2) 0.060(2) 0.0302(17) 0.0009(15) 0.0202(17) 0.0098(17)
C18 0.045(2) 0.058(2) 0.0378(18) 0.0024(15) 0.0219(17) 0.0084(17)
C19 0.044(2) 0.0397(18) 0.0346(17) -0.0014(14) 0.0186(17) 0.0044(16)
C20 0.042(2) 0.0340(17) 0.0421(18) -0.0003(14) 0.0246(17) -0.0006(15)
C21 0.053(3) 0.051(4) 0.040(2) -0.011(2) 0.027(2) -0.008(3)
C22 0.049(5) 0.056(5) 0.053(5) -0.007(4) 0.030(4) 0.006(4)
C23 0.048(5) 0.086(7) 0.077(7) -0.012(5) 0.030(5) 0.013(4)
C24 0.064(4) 0.096(7) 0.047(2) -0.014(4) 0.032(3) 0.005(4)
C25 0.073(7) 0.112(7) 0.040(4) 0.008(4) 0.037(4) 0.017(5)
C26 0.074(7) 0.089(6) 0.034(4) 0.012(4) 0.030(4) 0.016(5)
C21B 0.053(3) 0.051(4) 0.040(2) -0.011(2) 0.027(2) -0.008(3)
C22B 0.14(3) 0.055(11) 0.103(17) 0.013(11) 0.10(2) 0.003(12)
C23B 0.13(2) 0.039(9) 0.094(15) -0.020(9) 0.097(17) -0.013(9)
C24B 0.064(4) 0.096(7) 0.047(2) -0.014(4) 0.032(3) 0.005(4)
C25B 0.14(2) 0.083(12) 0.082(13) 0.024(10) 0.087(16) 0.015(13)
C26B 0.14(2) 0.073(10) 0.079(14) -0.003(9) 0.084(17) 0.010(12)
C27 0.048(2) 0.0364(18) 0.0389(18) -0.0044(15) 0.0171(17) 0.0005(17)
C28 0.051(2) 0.043(2) 0.0396(18) -0.0020(16) 0.0144(18) 0.0050(17)
C29 0.066(3) 0.046(2) 0.0363(19) -0.0016(16) 0.014(2) 0.015(2)
C30 0.050(3) 0.058(2) 0.047(2) -0.0085(18) 0.0079(19) 0.008(2)
C31 0.049(3) 0.055(2) 0.058(2) -0.0100(19) 0.017(2) -0.0102(19)
C32 0.051(3) 0.041(2) 0.046(2) -0.0012(16) 0.0102(19) -0.0032(18)
C33 0.036(2) 0.055(2) 0.0365(17) -0.0030(16) 0.0155(16) 0.0087(17)
C34 0.054(3) 0.069(3) 0.051(2) -0.015(2) 0.030(2) -0.010(2)
C35 0.073(4) 0.105(4) 0.058(3) -0.025(3) 0.044(3) -0.029(3)
C36 0.056(3) 0.123(4) 0.061(2) -0.034(3) 0.040(2) -0.014(3)
C37 0.054(3) 0.091(3) 0.073(3) -0.037(2) 0.033(3) -0.003(3)
C38 0.055(3) 0.064(3) 0.058(2) -0.011(2) 0.033(2) 0.004(2)
C33E 0.036(2) 0.055(2) 0.0365(17) -0.0030(16) 0.0155(16) 0.0087(17)
C34E 0.054(3) 0.069(3) 0.051(2) -0.015(2) 0.030(2) -0.010(2)
C35E 0.073(4) 0.105(4) 0.058(3) -0.025(3) 0.044(3) -0.029(3)
C36E 0.056(3) 0.123(4) 0.061(2) -0.034(3) 0.040(2) -0.014(3)
C37E 0.054(3) 0.091(3) 0.073(3) -0.037(2) 0.033(3) -0.003(3)
C38E 0.055(3) 0.064(3) 0.058(2) -0.011(2) 0.033(2) 0.004(2)
C39 0.043(2) 0.0357(18) 0.0369(17) -0.0030(14) 0.0221(16) 0.0005(16)
C40 0.044(2) 0.0388(19) 0.0456(19) -0.0030(15) 0.0255(18) -0.0021(16)
C41 0.045(2) 0.047(2) 0.050(2) 0.0000(16) 0.0280(19) 0.0039(17)
C42 0.038(2) 0.056(2) 0.054(2) -0.0062(18) 0.0238(18) -0.0006(18)
C43 0.053(3) 0.048(2) 0.075(3) 0.001(2) 0.025(2) -0.0144(19)
C44 0.056(3) 0.043(2) 0.061(2) 0.0047(17) 0.022(2) -0.0014(19)
N1 0.0479(19) 0.0403(15) 0.0368(14) 0.0011(12) 0.0223(14) 0.0054(13)
N2 0.0467(19) 0.0403(15) 0.0317(13) -0.0016(12) 0.0191(14) 0.0017(13)
N3 0.0387(17) 0.0382(15) 0.0364(14) -0.0022(11) 0.0177(13) 0.0007(12)
N4 0.0404(18) 0.0443(16) 0.0322(13) 0.0000(11) 0.0184(13) 0.0013(13)
C2A 0.057(2) 0.0484(19) 0.0487(19) 0.0001(16) 0.0364(18) -0.0015(16)
N1A 0.064(3) 0.054(2) 0.049(2) -0.0065(16) 0.0403(19) -0.0133(18)
Cl1A 0.056(2) 0.173(10) 0.054(5) -0.007(6) 0.033(4) -0.031(6)
N1B 0.057(2) 0.0484(19) 0.0487(19) 0.0001(16) 0.0364(18) -0.0015(16)
C3B 0.064(3) 0.054(2) 0.049(2) -0.0065(16) 0.0403(19) -0.0133(18)
Cl1B 0.042(3) 0.104(4) 0.043(2) -0.019(2) 0.027(2) 0.005(2)
C7C 0.075(3) 0.047(2) 0.0421(19) -0.0054(16) 0.032(2) 0.0009(19)
N1C 0.072(3) 0.046(2) 0.0385(19) -0.0004(15) 0.0221(18) 0.0017(19)
Cl1C 0.10(2) 0.080(17) 0.039(7) -0.004(10) 0.028(13) 0.016(14)
N1D 0.075(3) 0.047(2) 0.0421(19) -0.0054(16) 0.032(2) 0.0009(19)
C8D 0.072(3) 0.046(2) 0.0385(19) -0.0004(15) 0.0221(18) 0.0017(19)
Cl1D 0.066(7) 0.064(7) 0.052(5) -0.003(4) 0.016(3) 0.000(5)
C12E 0.044(2) 0.0510(19) 0.0418(18) -0.0006(14) 0.0184(16) 0.0041(15)
N1E 0.046(2) 0.056(2) 0.053(2) -0.0044(17) 0.0306(19) 0.0012(17)
Cl1E 0.051(9) 0.20(3) 0.15(2) -0.05(2) 0.013(14) 0.038(15)
N1F 0.044(2) 0.0510(19) 0.0418(18) -0.0006(14) 0.0184(16) 0.0041(15)
C13F 0.046(2) 0.056(2) 0.053(2) -0.0044(17) 0.0306(19) 0.0012(17)
Cl1F 0.0430(16) 0.0907(19) 0.0422(13) -0.0129(12) 0.0166(11) 0.0242(13)
C17G 0.050(2) 0.060(2) 0.0302(17) 0.0009(15) 0.0202(17) 0.0098(17)
N1G 0.045(2) 0.058(2) 0.0378(18) 0.0024(15) 0.0219(17) 0.0084(17)
Cl1G 0.050(3) 0.060(3) 0.030(2) 0.000(2) 0.020(2) 0.011(3)
N1H 0.050(2) 0.060(2) 0.0302(17) 0.0009(15) 0.0202(17) 0.0098(17)
C18H 0.045(2) 0.058(2) 0.0378(18) 0.0024(15) 0.0219(17) 0.0084(17)
Cl1H 0.087(15) 0.083(17) 0.049(11) -0.025(11) 0.017(7) -0.018(13)
_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 1.370(4) . ?
C1 C20 1.411(4) . ?
C1 C2 1.426(4) . ?
C2 C3 1.338(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(5) . ?
C3 H3 0.9500 . ?
C4 N1 1.373(4) . ?
C4 C5 1.413(4) . ?
C5 C6 1.390(5) . ?
C5 C21 1.500(6) . ?
C5 C21B 1.523(12) . ?
C6 N2 1.370(4) . ?
C6 C7 1.422(4) . ?
C7 C8 1.336(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.416(4) . ?
C8 H8 0.9500 . ?
C9 N2 1.377(4) . ?
C9 C10 1.396(4) . ?
C10 C11 1.420(4) . ?
C10 C27 1.496(4) . ?
C11 N3 1.368(4) . ?
C11 C12 1.416(4) . ?
C12 C13 1.340(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.437(4) . ?
C13 H13 0.9500 . ?
C14 N3 1.366(4) . ?
C14 C15 1.403(4) . ?
C15 C16 1.397(4) . ?
C15 C33 1.497(4) . ?
C16 N4 1.371(4) . ?
C16 C17 1.423(4) . ?
C17 C18 1.341(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.433(4) . ?
C18 H18 0.9500 . ?
C19 N4 1.376(4) . ?
C19 C20 1.396(4) . ?
C20 C39 1.498(4) . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C26 1.3900 . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C21B C26B 1.363(14) . ?
C21B C22B 1.366(13) . ?
C22B C23B 1.361(13) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.367(14) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.346(15) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.397(13) . ?
C25B H25B 0.9500 . ?
C26B H26B 0.9500 . ?
C27 C28 1.385(4) . ?
C27 C32 1.386(5) . ?
C28 C29 1.400(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.371(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(5) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.368(5) . ?
C33 C38 1.399(5) . ?
C34 C35 1.373(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.358(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.371(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.390(5) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C34E C35E 1.369(19) . ?
C34E H34E 0.9500 . ?
C35E H35E 0.9500 . ?
C37E C38E 1.387(19) . ?
C37E H37E 0.9500 . ?
C38E H38E 0.9500 . ?
C39 C40 1.385(4) . ?
C39 C44 1.388(4) . ?
C40 C41 1.384(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.369(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.371(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.386(5) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
N4 H4A 0.8800 . ?
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 C20 125.5(3) . . ?
N1 C1 C2 111.2(3) . . ?
C20 C1 C2 123.2(3) . . ?
C3 C2 C1 106.1(3) . . ?
C3 C2 H2 127.0 . . ?
C1 C2 H2 127.0 . . ?
C2 C3 C4 108.0(3) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
N1 C4 C5 125.2(3) . . ?
N1 C4 C3 110.1(3) . . ?
C5 C4 C3 124.7(3) . . ?
C6 C5 C4 125.1(3) . . ?
C6 C5 C21 115.8(4) . . ?
C4 C5 C21 119.1(4) . . ?
C6 C5 C21B 121.2(8) . . ?
C4 C5 C21B 113.1(9) . . ?
N2 C6 C5 126.5(3) . . ?
N2 C6 C7 107.2(3) . . ?
C5 C6 C7 126.4(3) . . ?
C8 C7 C6 107.6(3) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 C9 109.7(3) . . ?
C7 C8 H8 125.1 . . ?
C9 C8 H8 125.1 . . ?
N2 C9 C10 126.6(3) . . ?
N2 C9 C8 106.0(3) . . ?
C10 C9 C8 127.4(3) . . ?
C9 C10 C11 124.1(3) . . ?
C9 C10 C27 118.3(3) . . ?
C11 C10 C27 117.6(3) . . ?
N3 C11 C12 112.1(3) . . ?
N3 C11 C10 125.7(3) . . ?
C12 C11 C10 122.3(3) . . ?
C13 C12 C11 104.8(3) . . ?
C13 C12 H12 127.6 . . ?
C11 C12 H12 127.6 . . ?
C12 C13 C14 109.3(3) . . ?
C12 C13 H13 125.4 . . ?
C14 C13 H13 125.4 . . ?
N3 C14 C15 126.4(3) . . ?
N3 C14 C13 108.3(3) . . ?
C15 C14 C13 125.2(3) . . ?
C16 C15 C14 124.5(3) . . ?
C16 C15 C33 117.1(3) . . ?
C14 C15 C33 118.3(3) . . ?
N4 C16 C15 126.3(3) . . ?
N4 C16 C17 107.0(3) . . ?
C15 C16 C17 126.6(3) . . ?
C18 C17 C16 108.7(3) . . ?
C18 C17 H17 125.6 . . ?
C16 C17 H17 125.6 . . ?
C17 C18 C19 108.1(3) . . ?
C17 C18 H18 125.9 . . ?
C19 C18 H18 125.9 . . ?
N4 C19 C20 127.2(3) . . ?
N4 C19 C18 106.7(3) . . ?
C20 C19 C18 126.1(3) . . ?
C19 C20 C1 124.6(3) . . ?
C19 C20 C39 116.4(3) . . ?
C1 C20 C39 119.0(3) . . ?
C22 C21 C26 120.0 . . ?
C22 C21 C5 121.5(5) . . ?
C26 C21 C5 118.5(5) . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C26B C21B C22B 114.7(10) . . ?
C26B C21B C5 125.6(15) . . ?
C22B C21B C5 119.6(15) . . ?
C23B C22B C21B 123.8(12) . . ?
C23B C22B H22B 118.1 . . ?
C21B C22B H22B 118.1 . . ?
C22B C23B C24B 119.2(12) . . ?
C22B C23B H23B 120.4 . . ?
C24B C23B H23B 120.4 . . ?
C25B C24B C23B 119.3(11) . . ?
C25B C24B H24B 120.4 . . ?
C23B C24B H24B 120.4 . . ?
C24B C25B C26B 119.0(12) . . ?
C24B C25B H25B 120.5 . . ?
C26B C25B H25B 120.5 . . ?
C21B C26B C25B 123.2(12) . . ?
C21B C26B H26B 118.4 . . ?
C25B C26B H26B 118.4 . . ?
C28 C27 C32 118.4(3) . . ?
C28 C27 C10 120.4(3) . . ?
C32 C27 C10 121.2(3) . . ?
C27 C28 C29 120.3(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.7(4) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C32 119.9(4) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C27 121.2(3) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
C34 C33 C38 118.3(3) . . ?
C34 C33 C15 122.1(3) . . ?
C38 C33 C15 119.6(3) . . ?
C33 C34 C35 121.2(4) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C36 C35 C34 120.3(4) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C37 120.5(4) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C36 C37 C38 119.4(4) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
C37 C38 C33 120.2(4) . . ?
C37 C38 H38 119.9 . . ?
C33 C38 H38 119.9 . . ?
C35E C34E H34E 121.0 . . ?
C34E C35E H35E 118.5 . . ?
C38E C37E H37E 120.3 . . ?
C37E C38E H38E 119.7 . . ?
C40 C39 C44 118.5(3) . . ?
C40 C39 C20 120.0(3) . . ?
C44 C39 C20 121.4(3) . . ?
C41 C40 C39 120.9(3) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
C42 C41 C40 119.9(3) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 120.1(3) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C42 C43 C44 120.3(3) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C43 C44 C39 120.3(3) . . ?
C43 C44 H44 119.9 . . ?
C39 C44 H44 119.9 . . ?
C1 N1 C4 104.7(3) . . ?
C1 N1 H1A 127.6 . . ?
C4 N1 H1A 127.6 . . ?
C6 N2 C9 109.5(2) . . ?
C6 N2 H2A 125.2 . . ?
C9 N2 H2A 125.2 . . ?
C14 N3 C11 105.5(3) . . ?
C14 N3 H3A 127.3 . . ?
C11 N3 H3A 127.3 . . ?
C16 N4 C19 109.5(2) . . ?
C16 N4 H4A 125.3 . . ?
C19 N4 H4A 125.3 . . ?
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.051