# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#                                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_cd211527
_database_code_depnum_ccdc_archive 'CCDC 870941'
#TrackingRef 'cd211527.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 I N O3'
_chemical_formula_weight         405.18

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.5004(5)
_cell_length_b                   14.8567(7)
_cell_length_c                   21.8984(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3090.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6348
_cell_measurement_theta_min      4.621
_cell_measurement_theta_max      47.397

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.49889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18928
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6087
_reflns_number_gt                5546
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.7537P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6087
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
I1 I 0.48645(4) 0.52502(2) 0.979473(15) 0.06832(12) Uani 1 1 d . . .
I1' I 0.64820(4) 0.42439(2) 0.795726(17) 0.07005(12) Uani 1 1 d . . .
N1 N 0.0692(4) 0.5946(3) 0.92951(18) 0.0584(10) Uani 1 1 d . . .
N1' N 0.2579(4) 0.3035(3) 0.84158(18) 0.0555(10) Uani 1 1 d . . .
O1 O 0.1413(5) 0.4642(2) 0.97676(18) 0.0802(11) Uani 1 1 d . . .
O2 O -0.0249(6) 0.8613(3) 0.77702(19) 0.1009(15) Uani 1 1 d . . .
O3 O -0.1174(4) 0.5872(2) 0.79254(18) 0.0753(10) Uani 1 1 d . . .
O1' O 0.2996(5) 0.4537(3) 0.82357(19) 0.0803(12) Uani 1 1 d . . .
O2' O 0.2671(5) -0.0099(3) 0.9565(2) 0.0957(14) Uani 1 1 d . . .
O3' O 0.0927(4) 0.2314(3) 0.97541(16) 0.0674(9) Uani 1 1 d . . .
C1 C 0.1669(6) 0.5380(3) 0.9539(2) 0.0598(12) Uani 1 1 d . . .
C2 C 0.3041(5) 0.5823(3) 0.9458(2) 0.0528(11) Uani 1 1 d . . .
C3 C 0.2919(5) 0.6561(3) 0.91332(19) 0.0473(10) Uani 1 1 d . . .
C4 C 0.1395(5) 0.6681(3) 0.89607(19) 0.0465(10) Uani 1 1 d . . .
C5 C 0.0756(5) 0.7571(3) 0.9148(2) 0.0581(12) Uani 1 1 d . . .
H5 H 0.0730 0.7710 0.9562 0.070 Uiso 1 1 calc R . .
C6 C 0.0230(6) 0.8166(3) 0.8760(2) 0.0633(13) Uani 1 1 d . . .
H6 H -0.0198 0.8679 0.8917 0.076 Uiso 1 1 calc R . .
C7 C 0.0288(6) 0.8056(3) 0.8099(2) 0.0611(13) Uani 1 1 d . . .
C8 C 0.1035(5) 0.7257(3) 0.7852(2) 0.0549(11) Uani 1 1 d . . .
H8A H 0.2000 0.7422 0.7761 0.066 Uiso 1 1 calc R . .
H8B H 0.0591 0.7076 0.7472 0.066 Uiso 1 1 calc R . .
C9 C 0.1037(5) 0.6464(3) 0.8288(2) 0.0467(10) Uani 1 1 d . . .
H9 H 0.1739 0.6033 0.8141 0.056 Uiso 1 1 calc R . .
C10 C -0.0355(5) 0.5973(3) 0.8331(2) 0.0545(11) Uani 1 1 d . . .
C11 C -0.0566(6) 0.5635(4) 0.8982(3) 0.0699(15) Uani 1 1 d . . .
H11A H -0.1407 0.5892 0.9163 0.084 Uiso 1 1 calc R . .
H11B H -0.0635 0.4984 0.8993 0.084 Uiso 1 1 calc R . .
C12 C 0.4040(5) 0.7179(3) 0.8923(2) 0.0473(10) Uani 1 1 d . . .
C13 C 0.5110(6) 0.6852(3) 0.8546(2) 0.0594(12) Uani 1 1 d . . .
H13 H 0.5097 0.6252 0.8425 0.071 Uiso 1 1 calc R . .
C14 C 0.6177(6) 0.7400(4) 0.8351(3) 0.0725(15) Uani 1 1 d . . .
H14 H 0.6866 0.7175 0.8091 0.087 Uiso 1 1 calc R . .
C15 C 0.6235(6) 0.8268(4) 0.8536(3) 0.0797(18) Uani 1 1 d . . .
H15 H 0.6965 0.8638 0.8406 0.096 Uiso 1 1 calc R . .
C16 C 0.5209(7) 0.8601(4) 0.8918(3) 0.0828(18) Uani 1 1 d . . .
H16 H 0.5257 0.9196 0.9048 0.099 Uiso 1 1 calc R . .
C17 C 0.4126(6) 0.8071(3) 0.9107(3) 0.0663(14) Uani 1 1 d . . .
H17 H 0.3437 0.8308 0.9363 0.080 Uiso 1 1 calc R . .
C1' C 0.3389(6) 0.3766(3) 0.8275(2) 0.0566(12) Uani 1 1 d . . .
C2' C 0.4841(5) 0.3410(3) 0.82175(19) 0.0482(10) Uani 1 1 d . . .
C3' C 0.4913(5) 0.2557(3) 0.83940(16) 0.0419(9) Uani 1 1 d . . .
C4' C 0.3452(5) 0.2270(3) 0.85979(18) 0.0430(9) Uani 1 1 d . . .
C5' C 0.2922(5) 0.1415(4) 0.8315(2) 0.0590(13) Uani 1 1 d . . .
H5' H 0.2767 0.1404 0.7896 0.071 Uiso 1 1 calc R . .
C6' C 0.2662(6) 0.0674(4) 0.8633(3) 0.0708(16) Uani 1 1 d . . .
H6' H 0.2280 0.0181 0.8430 0.085 Uiso 1 1 calc R . .
C7' C 0.2947(5) 0.0594(3) 0.9287(3) 0.0626(14) Uani 1 1 d . . .
C8' C 0.3593(6) 0.1374(3) 0.9609(2) 0.0562(11) Uani 1 1 d . . .
H8'1 H 0.4607 0.1297 0.9621 0.067 Uiso 1 1 calc R . .
H8'2 H 0.3252 0.1393 1.0026 0.067 Uiso 1 1 calc R . .
C9' C 0.3247(4) 0.2249(3) 0.92958(18) 0.0418(9) Uani 1 1 d . . .
H9' H 0.3826 0.2725 0.9477 0.050 Uiso 1 1 calc R . .
C10' C 0.1699(5) 0.2520(3) 0.9355(2) 0.0512(11) Uani 1 1 d . . .
C11' C 0.1319(6) 0.3089(4) 0.8789(3) 0.0673(14) Uani 1 1 d . . .
H11C H 0.0513 0.2839 0.8576 0.081 Uiso 1 1 calc R . .
H11D H 0.1114 0.3707 0.8902 0.081 Uiso 1 1 calc R . .
C12' C 0.6122(5) 0.1937(3) 0.84376(18) 0.0406(9) Uani 1 1 d . . .
C13' C 0.6240(6) 0.1195(3) 0.80523(19) 0.0518(11) Uani 1 1 d . . .
H13' H 0.5557 0.1088 0.7757 0.062 Uiso 1 1 calc R . .
C14' C 0.7373(6) 0.0617(3) 0.8110(2) 0.0622(13) Uani 1 1 d . . .
H14' H 0.7458 0.0129 0.7847 0.075 Uiso 1 1 calc R . .
C15' C 0.8359(6) 0.0758(4) 0.8546(3) 0.0657(13) Uani 1 1 d . . .
H15' H 0.9112 0.0361 0.8585 0.079 Uiso 1 1 calc R . .
C16' C 0.8252(6) 0.1476(4) 0.8929(3) 0.0682(14) Uani 1 1 d . . .
H16' H 0.8924 0.1563 0.9232 0.082 Uiso 1 1 calc R . .
C17' C 0.7152(5) 0.2074(3) 0.8870(2) 0.0532(11) Uani 1 1 d . . .
H17' H 0.7105 0.2574 0.9125 0.064 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
I1 0.0730(2) 0.0699(2) 0.06210(19) 0.01466(15) -0.02111(17) 0.01300(18)
I1' 0.0838(3) 0.04773(17) 0.0787(2) 0.01280(17) 0.0199(2) -0.00868(17)
N1 0.057(2) 0.060(3) 0.058(2) 0.0137(19) -0.0035(19) -0.010(2)
N1' 0.052(2) 0.061(2) 0.054(2) 0.0057(18) -0.0081(18) 0.0052(19)
O1 0.096(3) 0.068(2) 0.076(2) 0.034(2) -0.019(2) -0.021(2)
O2 0.135(4) 0.077(3) 0.091(3) 0.023(2) -0.006(3) 0.045(3)
O3 0.064(2) 0.079(2) 0.083(2) 0.009(2) -0.032(2) -0.0081(19)
O1' 0.092(3) 0.062(2) 0.087(3) 0.0222(19) -0.007(2) 0.020(2)
O2' 0.100(3) 0.052(2) 0.135(4) 0.014(2) 0.054(3) -0.008(2)
O3' 0.0533(19) 0.091(3) 0.058(2) -0.0143(19) 0.0135(17) -0.0068(18)
C1 0.071(3) 0.060(3) 0.048(2) 0.011(2) -0.009(2) -0.007(3)
C2 0.054(3) 0.047(2) 0.057(3) 0.006(2) -0.017(2) 0.002(2)
C3 0.053(3) 0.044(2) 0.045(2) -0.0057(18) -0.0026(19) 0.005(2)
C4 0.051(3) 0.044(2) 0.044(2) 0.0023(17) 0.001(2) 0.001(2)
C5 0.054(3) 0.064(3) 0.056(3) -0.011(2) 0.001(2) 0.006(2)
C6 0.060(3) 0.050(3) 0.081(3) -0.005(2) -0.006(3) 0.021(3)
C7 0.058(3) 0.049(3) 0.076(3) 0.013(2) -0.003(3) 0.008(2)
C8 0.062(3) 0.053(2) 0.050(3) 0.010(2) 0.001(2) 0.010(2)
C9 0.044(2) 0.046(2) 0.051(2) 0.0037(19) -0.0014(19) 0.0071(19)
C10 0.052(3) 0.045(2) 0.067(3) 0.001(2) -0.010(2) 0.004(2)
C11 0.053(3) 0.071(3) 0.085(4) 0.019(3) -0.008(3) -0.013(3)
C12 0.048(2) 0.042(2) 0.051(2) 0.0060(19) -0.012(2) 0.0057(19)
C13 0.061(3) 0.053(3) 0.065(3) -0.003(2) 0.005(3) 0.007(3)
C14 0.051(3) 0.082(4) 0.084(4) 0.004(3) 0.011(3) 0.008(3)
C15 0.047(3) 0.070(4) 0.122(5) 0.025(4) 0.008(3) 0.001(3)
C16 0.071(4) 0.041(3) 0.136(5) 0.005(3) -0.010(4) -0.007(3)
C17 0.058(3) 0.050(3) 0.092(4) -0.007(3) 0.007(3) 0.008(2)
C1' 0.072(3) 0.052(3) 0.046(2) 0.006(2) -0.008(2) 0.009(3)
C2' 0.057(3) 0.039(2) 0.048(2) 0.0030(17) 0.003(2) -0.006(2)
C3' 0.048(2) 0.044(2) 0.0339(18) -0.0049(15) -0.0056(18) -0.004(2)
C4' 0.042(2) 0.045(2) 0.041(2) -0.0037(17) -0.0048(18) -0.003(2)
C5' 0.052(3) 0.071(3) 0.054(3) -0.022(2) -0.002(2) -0.009(2)
C6' 0.058(3) 0.056(3) 0.098(4) -0.027(3) 0.020(3) -0.022(3)
C7' 0.052(3) 0.047(3) 0.089(4) 0.001(2) 0.034(3) -0.002(2)
C8' 0.055(3) 0.059(3) 0.055(3) 0.010(2) 0.007(2) -0.001(2)
C9' 0.040(2) 0.041(2) 0.044(2) -0.0045(17) -0.0025(17) -0.0058(18)
C10' 0.054(3) 0.048(2) 0.051(3) -0.0153(19) -0.005(2) -0.003(2)
C11' 0.053(3) 0.077(3) 0.072(3) 0.007(3) -0.007(3) 0.008(3)
C12' 0.049(3) 0.0318(19) 0.041(2) 0.0036(16) 0.0102(18) -0.0090(17)
C13' 0.068(3) 0.043(2) 0.044(2) -0.0039(18) 0.001(2) -0.007(2)
C14' 0.079(4) 0.040(2) 0.068(3) -0.002(2) 0.018(3) 0.000(2)
C15' 0.057(3) 0.057(3) 0.083(4) 0.014(3) 0.009(3) 0.010(3)
C16' 0.053(3) 0.073(3) 0.079(4) 0.009(3) -0.009(3) -0.003(3)
C17' 0.059(3) 0.052(3) 0.049(3) -0.008(2) -0.003(2) -0.011(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2 2.066(4) . ?
I1' C2' 2.072(4) . ?
N1 C1 1.361(7) . ?
N1 C11 1.453(6) . ?
N1 C4 1.475(6) . ?
N1' C1' 1.365(7) . ?
N1' C11' 1.452(7) . ?
N1' C4' 1.463(6) . ?
O1 C1 1.230(6) . ?
O2 C7 1.210(6) . ?
O3 C10 1.191(6) . ?
O1' C1' 1.208(6) . ?
O2' C7' 1.223(6) . ?
O3' C10' 1.182(6) . ?
C1 C2 1.471(7) . ?
C2 C3 1.312(6) . ?
C3 C12 1.480(7) . ?
C3 C4 1.506(7) . ?
C4 C5 1.512(6) . ?
C4 C9 1.546(6) . ?
C5 C6 1.323(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.459(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.485(7) . ?
C8 C9 1.517(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.513(7) . ?
C9 H9 0.9800 . ?
C10 C11 1.525(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.388(7) . ?
C12 C13 1.397(7) . ?
C13 C14 1.369(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.353(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.361(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C1' C2' 1.482(7) . ?
C2' C3' 1.326(6) . ?
C3' C12' 1.476(6) . ?
C3' C4' 1.519(6) . ?
C4' C5' 1.500(6) . ?
C4' C9' 1.541(6) . ?
C5' C6' 1.326(8) . ?
C5' H5' 0.9300 . ?
C6' C7' 1.463(8) . ?
C6' H6' 0.9300 . ?
C7' C8' 1.488(7) . ?
C8' C9' 1.507(6) . ?
C8' H8'1 0.9700 . ?
C8' H8'2 0.9700 . ?
C9' C10' 1.530(7) . ?
C9' H9' 0.9800 . ?
C10' C11' 1.544(7) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' C17' 1.377(6) . ?
C12' C13' 1.393(6) . ?
C13' C14' 1.382(7) . ?
C13' H13' 0.9300 . ?
C14' C15' 1.355(8) . ?
C14' H14' 0.9300 . ?
C15' C16' 1.360(8) . ?
C15' H15' 0.9300 . ?
C16' C17' 1.378(7) . ?
C16' H16' 0.9300 . ?
C17' H17' 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 123.4(4) . . ?
C1 N1 C4 110.1(4) . . ?
C11 N1 C4 111.9(4) . . ?
C1' N1' C11' 123.2(4) . . ?
C1' N1' C4' 111.1(4) . . ?
C11' N1' C4' 110.9(4) . . ?
O1 C1 N1 125.1(5) . . ?
O1 C1 C2 128.5(5) . . ?
N1 C1 C2 106.3(4) . . ?
C3 C2 C1 111.1(4) . . ?
C3 C2 I1 127.7(4) . . ?
C1 C2 I1 121.1(3) . . ?
C2 C3 C12 128.6(4) . . ?
C2 C3 C4 108.7(4) . . ?
C12 C3 C4 122.7(4) . . ?
N1 C4 C3 102.9(4) . . ?
N1 C4 C5 109.3(4) . . ?
C3 C4 C5 115.0(4) . . ?
N1 C4 C9 102.6(4) . . ?
C3 C4 C9 115.2(4) . . ?
C5 C4 C9 110.7(4) . . ?
C6 C5 C4 124.1(5) . . ?
C6 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C5 C6 C7 123.3(4) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
O2 C7 C6 119.9(5) . . ?
O2 C7 C8 122.2(5) . . ?
C6 C7 C8 118.0(4) . . ?
C7 C8 C9 113.1(4) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 114.4(4) . . ?
C10 C9 C4 103.5(4) . . ?
C8 C9 C4 116.0(4) . . ?
C10 C9 H9 107.5 . . ?
C8 C9 H9 107.5 . . ?
C4 C9 H9 107.5 . . ?
O3 C10 C9 125.8(5) . . ?
O3 C10 C11 124.8(5) . . ?
C9 C10 C11 109.4(4) . . ?
N1 C11 C10 103.2(4) . . ?
N1 C11 H11A 111.1 . . ?
C10 C11 H11A 111.1 . . ?
N1 C11 H11B 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C17 C12 C13 117.5(5) . . ?
C17 C12 C3 123.0(4) . . ?
C13 C12 C3 119.5(4) . . ?
C14 C13 C12 121.1(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 120.3(6) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.7(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 120.6(5) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
O1' C1' N1' 126.5(5) . . ?
O1' C1' C2' 128.3(5) . . ?
N1' C1' C2' 105.1(4) . . ?
C3' C2' C1' 111.4(4) . . ?
C3' C2' I1' 127.8(4) . . ?
C1' C2' I1' 120.7(3) . . ?
C2' C3' C12' 130.9(4) . . ?
C2' C3' C4' 107.9(4) . . ?
C12' C3' C4' 121.1(3) . . ?
N1' C4' C5' 110.8(4) . . ?
N1' C4' C3' 102.7(3) . . ?
C5' C4' C3' 115.1(4) . . ?
N1' C4' C9' 102.3(3) . . ?
C5' C4' C9' 110.5(4) . . ?
C3' C4' C9' 114.4(3) . . ?
C6' C5' C4' 123.3(5) . . ?
C6' C5' H5' 118.4 . . ?
C4' C5' H5' 118.4 . . ?
C5' C6' C7' 123.2(5) . . ?
C5' C6' H6' 118.4 . . ?
C7' C6' H6' 118.4 . . ?
O2' C7' C6' 121.0(5) . . ?
O2' C7' C8' 120.6(6) . . ?
C6' C7' C8' 118.5(4) . . ?
C7' C8' C9' 111.5(4) . . ?
C7' C8' H8'1 109.3 . . ?
C9' C8' H8'1 109.3 . . ?
C7' C8' H8'2 109.3 . . ?
C9' C8' H8'2 109.3 . . ?
H8'1 C8' H8'2 108.0 . . ?
C8' C9' C10' 113.4(4) . . ?
C8' C9' C4' 116.1(4) . . ?
C10' C9' C4' 101.6(3) . . ?
C8' C9' H9' 108.4 . . ?
C10' C9' H9' 108.4 . . ?
C4' C9' H9' 108.4 . . ?
O3' C10' C9' 126.3(4) . . ?
O3' C10' C11' 126.2(5) . . ?
C9' C10' C11' 107.5(4) . . ?
N1' C11' C10' 103.2(4) . . ?
N1' C11' H11C 111.1 . . ?
C10' C11' H11C 111.1 . . ?
N1' C11' H11D 111.1 . . ?
C10' C11' H11D 111.1 . . ?
H11C C11' H11D 109.1 . . ?
C17' C12' C13' 118.5(4) . . ?
C17' C12' C3' 120.4(4) . . ?
C13' C12' C3' 121.1(4) . . ?
C14' C13' C12' 119.9(4) . . ?
C14' C13' H13' 120.0 . . ?
C12' C13' H13' 120.0 . . ?
C15' C14' C13' 120.5(5) . . ?
C15' C14' H14' 119.7 . . ?
C13' C14' H14' 119.7 . . ?
C14' C15' C16' 120.2(5) . . ?
C14' C15' H15' 119.9 . . ?
C16' C15' H15' 119.9 . . ?
C15' C16' C17' 120.4(5) . . ?
C15' C16' H16' 119.8 . . ?
C17' C16' H16' 119.8 . . ?
C12' C17' C16' 120.5(4) . . ?
C12' C17' H17' 119.8 . . ?
C16' C17' H17' 119.8 . . ?

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
C11 N1 C1 O1 -33.4(8) . . . . ?
C4 N1 C1 O1 -169.2(5) . . . . ?
C11 N1 C1 C2 145.4(5) . . . . ?
C4 N1 C1 C2 9.6(5) . . . . ?
O1 C1 C2 C3 172.7(5) . . . . ?
N1 C1 C2 C3 -6.1(6) . . . . ?
O1 C1 C2 I1 -4.2(7) . . . . ?
N1 C1 C2 I1 177.1(3) . . . . ?
C1 C2 C3 C12 -176.8(4) . . . . ?
I1 C2 C3 C12 -0.2(7) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
I1 C2 C3 C4 176.6(3) . . . . ?
C1 N1 C4 C3 -9.5(5) . . . . ?
C11 N1 C4 C3 -150.6(4) . . . . ?
C1 N1 C4 C5 -132.1(4) . . . . ?
C11 N1 C4 C5 86.8(5) . . . . ?
C1 N1 C4 C9 110.4(4) . . . . ?
C11 N1 C4 C9 -30.7(5) . . . . ?
C2 C3 C4 N1 5.5(5) . . . . ?
C12 C3 C4 N1 -177.4(4) . . . . ?
C2 C3 C4 C5 124.2(4) . . . . ?
C12 C3 C4 C5 -58.7(6) . . . . ?
C2 C3 C4 C9 -105.3(4) . . . . ?
C12 C3 C4 C9 71.8(5) . . . . ?
N1 C4 C5 C6 -125.7(5) . . . . ?
C3 C4 C5 C6 119.2(6) . . . . ?
C9 C4 C5 C6 -13.4(7) . . . . ?
C4 C5 C6 C7 -4.1(9) . . . . ?
C5 C6 C7 O2 177.9(6) . . . . ?
C5 C6 C7 C8 -3.0(8) . . . . ?
O2 C7 C8 C9 -153.7(6) . . . . ?
C6 C7 C8 C9 27.3(7) . . . . ?
C7 C8 C9 C10 75.0(6) . . . . ?
C7 C8 C9 C4 -45.5(6) . . . . ?
N1 C4 C9 C10 28.4(4) . . . . ?
C3 C4 C9 C10 139.3(4) . . . . ?
C5 C4 C9 C10 -88.1(4) . . . . ?
N1 C4 C9 C8 154.5(4) . . . . ?
C3 C4 C9 C8 -94.6(5) . . . . ?
C5 C4 C9 C8 38.0(6) . . . . ?
C8 C9 C10 O3 33.7(7) . . . . ?
C4 C9 C10 O3 160.9(5) . . . . ?
C8 C9 C10 C11 -145.4(4) . . . . ?
C4 C9 C10 C11 -18.3(5) . . . . ?
C1 N1 C11 C10 -115.9(5) . . . . ?
C4 N1 C11 C10 19.2(6) . . . . ?
O3 C10 C11 N1 -178.6(5) . . . . ?
C9 C10 C11 N1 0.6(5) . . . . ?
C2 C3 C12 C17 -116.7(6) . . . . ?
C4 C3 C12 C17 66.8(6) . . . . ?
C2 C3 C12 C13 59.9(7) . . . . ?
C4 C3 C12 C13 -116.5(5) . . . . ?
C17 C12 C13 C14 -2.0(8) . . . . ?
C3 C12 C13 C14 -178.8(5) . . . . ?
C12 C13 C14 C15 1.8(9) . . . . ?
C13 C14 C15 C16 -0.4(10) . . . . ?
C14 C15 C16 C17 -0.7(10) . . . . ?
C15 C16 C17 C12 0.5(9) . . . . ?
C13 C12 C17 C16 0.8(8) . . . . ?
C3 C12 C17 C16 177.5(5) . . . . ?
C11' N1' C1' O1' -28.0(8) . . . . ?
C4' N1' C1' O1' -163.3(5) . . . . ?
C11' N1' C1' C2' 149.0(4) . . . . ?
C4' N1' C1' C2' 13.8(5) . . . . ?
O1' C1' C2' C3' 168.8(5) . . . . ?
N1' C1' C2' C3' -8.2(5) . . . . ?
O1' C1' C2' I1' -6.5(7) . . . . ?
N1' C1' C2' I1' 176.5(3) . . . . ?
C1' C2' C3' C12' -177.6(4) . . . . ?
I1' C2' C3' C12' -2.7(7) . . . . ?
C1' C2' C3' C4' -0.6(5) . . . . ?
I1' C2' C3' C4' 174.3(3) . . . . ?
C1' N1' C4' C5' -137.3(4) . . . . ?
C11' N1' C4' C5' 81.7(5) . . . . ?
C1' N1' C4' C3' -14.0(4) . . . . ?
C11' N1' C4' C3' -154.9(4) . . . . ?
C1' N1' C4' C9' 104.9(4) . . . . ?
C11' N1' C4' C9' -36.1(5) . . . . ?
C2' C3' C4' N1' 8.4(4) . . . . ?
C12' C3' C4' N1' -174.2(3) . . . . ?
C2' C3' C4' C5' 128.9(4) . . . . ?
C12' C3' C4' C5' -53.7(5) . . . . ?
C2' C3' C4' C9' -101.6(4) . . . . ?
C12' C3' C4' C9' 75.8(5) . . . . ?
N1' C4' C5' C6' -128.7(5) . . . . ?
C3' C4' C5' C6' 115.4(5) . . . . ?
C9' C4' C5' C6' -16.0(7) . . . . ?
C4' C5' C6' C7' -3.9(8) . . . . ?
C5' C6' C7' O2' 178.9(5) . . . . ?
C5' C6' C7' C8' -1.6(8) . . . . ?
O2' C7' C8' C9' -153.8(5) . . . . ?
C6' C7' C8' C9' 26.7(6) . . . . ?
C7' C8' C9' C10' 69.6(5) . . . . ?
C7' C8' C9' C4' -47.6(5) . . . . ?
N1' C4' C9' C8' 160.1(4) . . . . ?
C5' C4' C9' C8' 42.1(5) . . . . ?
C3' C4' C9' C8' -89.7(5) . . . . ?
N1' C4' C9' C10' 36.6(4) . . . . ?
C5' C4' C9' C10' -81.5(4) . . . . ?
C3' C4' C9' C10' 146.8(4) . . . . ?
C8' C9' C10' O3' 26.9(6) . . . . ?
C4' C9' C10' O3' 152.2(4) . . . . ?
C8' C9' C10' C11' -151.6(4) . . . . ?
C4' C9' C10' C11' -26.3(4) . . . . ?
C1' N1' C11' C10' -116.2(5) . . . . ?
C4' N1' C11' C10' 19.1(5) . . . . ?
O3' C10' C11' N1' -172.7(5) . . . . ?
C9' C10' C11' N1' 5.8(5) . . . . ?
C2' C3' C12' C17' 68.9(6) . . . . ?
C4' C3' C12' C17' -107.9(5) . . . . ?
C2' C3' C12' C13' -112.3(5) . . . . ?
C4' C3' C12' C13' 71.0(5) . . . . ?
C17' C12' C13' C14' -0.1(6) . . . . ?
C3' C12' C13' C14' -178.9(4) . . . . ?
C12' C13' C14' C15' 1.2(7) . . . . ?
C13' C14' C15' C16' -0.7(8) . . . . ?
C14' C15' C16' C17' -1.0(8) . . . . ?
C13' C12' C17' C16' -1.6(7) . . . . ?
C3' C12' C17' C16' 177.3(4) . . . . ?
C15' C16' C17' C12' 2.2(8) . . . . ?

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
C16' H16' O3' 0.93 2.48 3.358(7) 156.5 1_655
C17 H17 O2' 0.93 2.52 3.211(6) 131.8 1_565
C14' H14' O1' 0.93 2.57 3.374(6) 145.6 3_646
C5' H5' O3 0.93 2.48 3.284(6) 144.9 3_546
C8' H8'1 O1 0.97 2.58 3.364(7) 137.5 4_557

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.073