# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2008
data_global
_journal_name_full Chem.Commun.
_journal_coden_Cambridge 0182
_publ_contact_author_name 'Viktor Zhdankin'
_publ_contact_author_email VZHDANKI@D.UMN.EDU
_publ_section_title
;
Preparation and X-ray crystal structure of
2-iodyl-N,N-dialkylaniline oxides: first entry into the heterocyclic
system of benziodoxazole
;
loop_
_publ_author_name
'Viktor Zhdankin'
'Rashad R Karimov'
'Zeinul-Gabiden Kazhkenov'
'Victor Nemykin'
# Attachment '5b.cif'
#==============================================================================
data_1
_database_code_depnum_ccdc_archive 'CCDC 696745'
_publ_section_exptl_refinement
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were merged.
The absolute configuration was arbitrarily assigned.
The relatively large ratio of minimum to maximum corrections applied in the
multiscan process (1:nnn) reflect changes in the illuminated volume of the
crystal.
Changes in illuminated volume were kept to a minimum, and were taken into
account (G\"orbitz, 1999) by the multi-scan inter-frame scaling
(DENZO/SCALEPACK, Otwinowski & Minor, 1997).
G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090--1098.
The H atoms were all located in a difference map, but those attached to carbon
atoms were repositioned geometrically. The H atoms were initially refined with
soft restraints on the bond lengths and angles to regularize their geometry
(C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86
O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2--1.5 times
U~eq~ of the parent atom), after which the positions were refined with
riding constraints.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
(type here to add preparation details)
;
# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example
#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a 8.1788(16)
_cell_length_b 10.512(2)
_cell_length_c 15.850(3)
_cell_angle_alpha 71.58(3)
_cell_angle_beta 82.16(3)
_cell_angle_gamma 78.02(3)
_cell_volume 1261.1(5)
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M 'P -1 '
_symmetry_space_group_name_Hall '-P 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C11 H16 I1 N1 O3
# Dc = 1.78 Fooo = 664.00 Mu = 25.33 M = 674.31
# Found Formula = C11 H16 I1 N1 O3
# Dc = 1.78 FOOO = 664.00 Mu = 25.32 M = 674.31
_chemical_formula_sum 'C11 H16 I1 N1 O3'
_chemical_formula_moiety 'C11 H16 I1 N1 O3'
_chemical_compound_source ?
_chemical_formula_weight 337.15
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 15
_cell_measurement_theta_max 18
_cell_measurement_temperature 298
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_min 0.11
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_max 0.31
_exptl_crystal_density_diffrn 1.776
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 664
_exptl_absorpt_coefficient_mu 2.532
# Sheldrick geometric approximatio 0.56 0.76
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_process_details '(North et al., 1968)'
_exptl_absorpt_correction_T_min 0.51
_exptl_absorpt_correction_T_max 0.76
_diffrn_measurement_device 'Rigaku AFC-7R'
_diffrn_measurement_device_type 'Rigaku AFC-7R'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method \w/2\q
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'Rigaku AFC-7R'
_computing_cell_refinement 'Win AFC'
_computing_data_reduction 'TexSan 10.3b'
_computing_structure_solution 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count 150
_diffrn_standards_number 3
_diffrn_standards_decay_% 0.00
_diffrn_ambient_temperature 298
_diffrn_reflns_number 4429
_reflns_number_total 4429
_diffrn_reflns_av_R_equivalents 0.000
# Number of reflections with Friedels Law is 4429
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 4439
_diffrn_reflns_theta_min 2.074
_diffrn_reflns_theta_max 24.993
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 24.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 0
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 17
_reflns_limit_h_min -9
_reflns_limit_h_max 9
_reflns_limit_k_min -11
_reflns_limit_k_max 12
_reflns_limit_l_min 0
_reflns_limit_l_max 18
_oxford_diffrn_Wilson_B_factor 0.00
_oxford_diffrn_Wilson_scale 0.00
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -1.14
_refine_diff_density_max 1.49
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns 2367
_refine_ls_number_restraints 1
_refine_ls_number_parameters 289
_oxford_refine_ls_R_factor_ref 0.0698
_refine_ls_wR_factor_ref 0.0886
_refine_ls_goodness_of_fit_ref 1.3471
_refine_ls_shift/su_max 0.000177
# The values computed from all data
_oxford_reflns_number_all 4409
_refine_ls_R_factor_all 0.1645
_refine_ls_wR_factor_all 0.0991
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 2367
_refine_ls_R_factor_gt 0.0698
_refine_ls_wR_factor_gt 0.0886
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
10.2 -1.95 5.80
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
User-defined data collection reference
User defined data reduction
User defined cell refinement
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J.
(2003). J. Appl. Cryst. 36, 1487--?.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst.
A24, 351--359.
Prince, E. Mathematical Techniques in Crystallography and Materials Science
Springer-Verlag, New York, 1982.
Sheldrick, G. M. (1986). SHELXS86. Program for the solution of crystal
structures. Univ. of G\"ottingen, Federal Republic of Germany.
Watkin, D. J. (1994). Acta Cryst. A50, 411--437.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
I1 I 0.16925(13) 0.70029(11) 0.29087(8) 0.0453 1.0000 Uani . . . . . . .
I2 I 0.08128(12) 0.35960(10) 0.45300(8) 0.0366 1.0000 Uani . . . . . . .
O3 O 0.0262(11) 0.1993(9) 0.3889(7) 0.0437 1.0000 Uani . . . . . . .
O4 O 0.0866(12) 0.2379(10) 0.5599(7) 0.0458 1.0000 Uani . . . . . . .
O5 O 0.0947(14) 0.8432(11) 0.2047(9) 0.0673 1.0000 Uani . . . . . . .
N6 N 0.5635(14) 0.7300(13) 0.2762(9) 0.0415 1.0000 Uani . . . . . . .
O7 O 0.0491(14) 0.5753(11) 0.2834(8) 0.0562 1.0000 Uani . . . . . . .
O8 O 0.4114(12) 0.8026(10) 0.2967(7) 0.0506 1.0000 Uani . . . . . . .
O9 O 0.1735(14) 0.4908(11) 0.4700(8) 0.0446 1.0000 Uani . . . . . . .
N10 N 0.1662(14) 0.1123(13) 0.3635(9) 0.0471 1.0000 Uani . . . . . . .
C11 C 0.620(2) 0.9247(16) 0.1391(12) 0.0604 1.0000 Uani . . . . . . .
C12 C 0.3213(19) 0.1627(14) 0.3664(11) 0.0385 1.0000 Uani . . . . . . .
C13 C 0.546(2) 0.6388(17) 0.2236(13) 0.0477 1.0000 Uani . . . . . . .
C14 C 0.387(2) 0.6167(18) 0.2204(11) 0.0487 1.0000 Uani . . . . . . .
C15 C 0.4570(19) 0.3175(16) 0.4045(10) 0.0393 1.0000 Uani . . . . . . .
C16 C 0.177(2) -0.0292(14) 0.4312(12) 0.0624 1.0000 Uani . . . . . . .
C17 C 0.6766(19) 0.8316(16) 0.2241(11) 0.0509 1.0000 Uani . . . . . . .
C18 C 0.612(2) 0.2553(18) 0.3731(12) 0.0561 1.0000 Uani . . . . . . .
C19 C 0.3108(18) 0.2697(15) 0.3966(10) 0.0321 1.0000 Uani . . . . . . .
C20 C 0.682(2) 0.573(2) 0.1852(14) 0.0714 1.0000 Uani . . . . . . .
C21 C 0.142(2) 0.233(2) 0.2027(12) 0.0713 1.0000 Uani . . . . . . .
C22 C 0.662(2) 0.490(2) 0.1374(14) 0.0752 1.0000 Uani . . . . . . .
C23 C 0.621(2) 0.144(2) 0.3452(12) 0.0675 1.0000 Uani . . . . . . .
C24 C 0.364(3) 0.5299(18) 0.1758(13) 0.0637 1.0000 Uani . . . . . . .
C25 C 0.635(2) 0.6496(16) 0.3611(11) 0.0620 1.0000 Uani . . . . . . .
C26 C 0.144(2) 0.1000(18) 0.2748(12) 0.0580 1.0000 Uani . . . . . . .
C27 C 0.505(3) 0.4674(19) 0.1333(14) 0.0775 1.0000 Uani . . . . . . .
C28 C 0.479(2) 0.0989(19) 0.3370(12) 0.0633 1.0000 Uani . . . . . . .
C29 C 0.098(4) 0.218(3) 0.1206(19) 0.1500 1.0000 Uani D . . . . . .
C30 C 0.676(4) 1.140(3) 0.0211(18) 0.1676 1.0000 Uani . . . . . . .
C31 C 0.720(3) 1.038(3) 0.1014(18) 0.1235 1.0000 Uani . . . . . . .
C32 C 0.110(4) 0.306(4) 0.037(2) 0.2571 1.0000 Uani D . . . . . .
H111 H 0.5047 0.9659 0.1489 0.0800 1.0000 Uiso R . . . . . .
H112 H 0.6282 0.8731 0.0972 0.0800 1.0000 Uiso R . . . . . .
H151 H 0.4496 0.3889 0.4284 0.0521 1.0000 Uiso R . . . . . .
H161 H 0.2792 -0.0856 0.4173 0.0911 1.0000 Uiso R . . . . . .
H162 H 0.1783 -0.0201 0.4896 0.0910 1.0000 Uiso R . . . . . .
H163 H 0.0830 -0.0692 0.4294 0.0910 1.0000 Uiso R . . . . . .
H171 H 0.6864 0.8866 0.2616 0.0660 1.0000 Uiso R . . . . . .
H172 H 0.7863 0.7808 0.2122 0.0660 1.0000 Uiso R . . . . . .
H181 H 0.7090 0.2884 0.3735 0.0611 1.0000 Uiso R . . . . . .
H201 H 0.7890 0.5859 0.1901 0.0860 1.0000 Uiso R . . . . . .
H211 H 0.0588 0.3026 0.2198 0.0840 1.0000 Uiso R . . . . . .
H212 H 0.2517 0.2588 0.1933 0.0841 1.0000 Uiso R . . . . . .
H221 H 0.7534 0.4429 0.1116 0.0931 1.0000 Uiso R . . . . . .
H231 H 0.7256 0.1012 0.3280 0.0759 1.0000 Uiso R . . . . . .
H241 H 0.2582 0.5093 0.1761 0.0810 1.0000 Uiso R . . . . . .
H251 H 0.7363 0.5911 0.3488 0.0871 1.0000 Uiso R . . . . . .
H252 H 0.6609 0.7109 0.3892 0.0870 1.0000 Uiso R . . . . . .
H253 H 0.5577 0.5958 0.4002 0.0870 1.0000 Uiso R . . . . . .
H261 H 0.2362 0.0348 0.2596 0.0880 1.0000 Uiso R . . . . . .
H262 H 0.0393 0.0691 0.2773 0.0881 1.0000 Uiso R . . . . . .
H271 H 0.4896 0.4165 0.0974 0.0860 1.0000 Uiso R . . . . . .
H281 H 0.4840 0.0265 0.3142 0.0771 1.0000 Uiso R . . . . . .
H301 H 0.7619 1.1944 -0.0034 0.2260 1.0000 Uiso R . . . . . .
H302 H 0.5732 1.1970 0.0330 0.2260 1.0000 Uiso R . . . . . .
H303 H 0.6595 1.0952 -0.0206 0.2260 1.0000 Uiso R . . . . . .
H311 H 0.7146 1.0839 0.1462 0.1340 1.0000 Uiso R . . . . . .
H312 H 0.8337 0.9939 0.0909 0.1340 1.0000 Uiso R . . . . . .
H291 H -0.0168 0.2029 0.1308 0.2021 1.0000 Uiso R . . . . . .
H292 H 0.1719 0.1359 0.1133 0.2021 1.0000 Uiso R . . . . . .
H321 H 0.0789 0.2799 -0.0103 0.2462 1.0000 Uiso R . . . . . .
H322 H 0.0370 0.3882 0.0420 0.2462 1.0000 Uiso R . . . . . .
H323 H 0.2238 0.3219 0.0247 0.2462 1.0000 Uiso 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 0.0353(9) 0.0446(10) 0.0605(11) -0.0205(8) 0.0042(8) -0.0145(7)
I2 0.0352(8) 0.0316(8) 0.0464(10) -0.0157(7) -0.0001(7) -0.0088(7)
O3 0.018(5) 0.041(7) 0.073(9) -0.026(6) 0.017(6) -0.007(5)
O4 0.034(6) 0.060(7) 0.053(8) -0.030(6) 0.007(5) -0.014(5)
O5 0.054(8) 0.037(7) 0.099(11) -0.002(7) 0.005(8) -0.019(6)
N6 0.023(7) 0.046(8) 0.056(10) -0.022(8) 0.005(7) -0.004(6)
O7 0.056(8) 0.048(8) 0.076(9) -0.029(7) 0.002(7) -0.021(6)
O8 0.034(6) 0.045(6) 0.083(9) -0.038(6) 0.004(6) -0.007(5)
O9 0.042(7) 0.036(7) 0.064(9) -0.030(6) 0.001(6) -0.006(5)
N10 0.029(7) 0.050(9) 0.065(10) -0.027(8) 0.012(7) -0.008(6)
C11 0.053(11) 0.047(11) 0.059(13) 0.009(10) 0.005(10) -0.006(9)
C12 0.042(10) 0.022(8) 0.049(11) -0.011(8) 0.000(8) -0.002(7)
C13 0.037(11) 0.040(10) 0.063(13) -0.009(10) -0.001(9) -0.014(8)
C14 0.063(13) 0.056(12) 0.034(11) -0.018(10) 0.013(9) -0.030(10)
C15 0.036(10) 0.039(10) 0.036(11) 0.004(8) 0.001(8) -0.017(8)
C16 0.053(11) 0.024(9) 0.094(15) -0.002(10) 0.014(10) -0.007(8)
C17 0.050(10) 0.046(10) 0.058(13) -0.016(10) 0.016(9) -0.024(9)
C18 0.045(11) 0.054(11) 0.072(14) -0.011(10) 0.000(10) -0.029(9)
C19 0.033(9) 0.046(10) 0.026(9) -0.021(8) 0.012(7) -0.017(8)
C20 0.048(12) 0.076(15) 0.105(18) -0.049(14) 0.009(12) -0.018(11)
C21 0.081(14) 0.090(16) 0.044(13) -0.015(12) -0.016(11) -0.017(12)
C22 0.036(11) 0.077(14) 0.117(19) -0.044(14) 0.025(11) -0.015(10)
C23 0.028(10) 0.107(17) 0.066(14) -0.018(13) -0.013(9) -0.013(10)
C24 0.075(14) 0.055(12) 0.072(15) -0.025(11) -0.003(12) -0.026(11)
C25 0.080(13) 0.048(11) 0.056(13) -0.004(10) -0.021(11) -0.016(10)
C26 0.054(12) 0.067(13) 0.065(14) -0.044(11) 0.018(10) -0.015(9)
C27 0.084(15) 0.079(15) 0.095(17) -0.063(13) 0.033(13) -0.038(12)
C28 0.053(12) 0.073(13) 0.080(15) -0.055(12) -0.006(11) 0.005(10)
C29 0.15(3) 0.19(3) 0.09(2) 0.03(2) 0.00(2) -0.10(2)
C30 0.25(4) 0.12(2) 0.11(2) 0.06(2) -0.02(2) -0.12(3)
C31 0.11(2) 0.10(2) 0.13(2) 0.007(19) 0.026(18) -0.033(17)
C32 0.09(3) 0.54(8) 0.12(3) -0.04(4) -0.01(2) -0.12(4)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.17390(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 . O5 . 1.745(12) yes
I1 . O7 . 1.836(10) yes
I1 . O8 . 2.466(9) yes
I1 . C14 . 2.149(18) yes
I2 . O9 2_566 2.732(10) yes
I2 . O3 . 2.366(10) yes
I2 . O4 . 1.771(11) yes
I2 . O9 . 1.807(10) yes
I2 . C19 . 2.135(14) yes
O3 . N10 . 1.407(14) yes
N6 . O8 . 1.374(14) yes
N6 . C13 . 1.49(2) yes
N6 . C17 . 1.524(17) yes
N6 . C25 . 1.469(19) yes
N10 . C12 . 1.484(18) yes
N10 . C16 . 1.528(18) yes
N10 . C26 . 1.490(19) yes
C11 . C17 . 1.46(2) yes
C11 . C31 . 1.50(2) yes
C11 . H111 . 0.969 no
C11 . H112 . 0.970 no
C12 . C19 . 1.337(18) yes
C12 . C28 . 1.41(2) yes
C13 . C14 . 1.38(2) yes
C13 . C20 . 1.36(2) yes
C14 . C24 . 1.37(2) yes
C15 . C18 . 1.40(2) yes
C15 . C19 . 1.424(19) yes
C15 . H151 . 0.930 no
C16 . H161 . 0.961 no
C16 . H162 . 0.961 no
C16 . H163 . 0.960 no
C17 . H171 . 0.972 no
C17 . H172 . 0.971 no
C18 . C23 . 1.36(2) yes
C18 . H181 . 0.932 no
C20 . C22 . 1.37(2) yes
C20 . H201 . 0.930 no
C21 . C26 . 1.50(2) yes
C21 . C29 . 1.46(3) yes
C21 . H211 . 0.972 no
C21 . H212 . 0.972 no
C22 . C27 . 1.37(2) yes
C22 . H221 . 0.929 no
C23 . C28 . 1.38(2) yes
C23 . H231 . 0.932 no
C24 . C27 . 1.40(2) yes
C24 . H241 . 0.931 no
C25 . H251 . 0.961 no
C25 . H252 . 0.960 no
C25 . H253 . 0.961 no
C26 . H261 . 0.969 no
C26 . H262 . 0.969 no
C27 . H271 . 0.930 no
C28 . H281 . 0.931 no
C29 . C32 . 1.361(17) yes
C29 . H291 . 0.970 no
C29 . H292 . 0.970 no
C30 . C31 . 1.41(3) yes
C30 . H301 . 0.961 no
C30 . H302 . 0.960 no
C30 . H303 . 0.961 no
C31 . H311 . 0.970 no
C31 . H312 . 0.970 no
C32 . H321 . 0.960 no
C32 . H322 . 0.960 no
C32 . H323 . 0.960 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 . I1 . O7 . 101.7(5) yes
O5 . I1 . O8 . 90.5(5) yes
O7 . I1 . O8 . 159.9(4) yes
O5 . I1 . C14 . 99.3(6) yes
O7 . I1 . C14 . 92.2(6) yes
O8 . I1 . C14 . 69.8(5) yes
O9 2_566 I2 . O3 . 120.8(3) yes
O9 2_566 I2 . O4 . 85.2(4) yes
O3 . I2 . O4 . 91.1(4) yes
O9 2_566 I2 . O9 . 74.8(5) yes
O3 . I2 . O9 . 160.8(4) yes
O4 . I2 . O9 . 101.9(5) yes
O9 2_566 I2 . C19 . 168.3(4) yes
O3 . I2 . C19 . 70.8(4) yes
O4 . I2 . C19 . 96.8(5) yes
O9 . I2 . C19 . 93.5(5) yes
I2 . O3 . N10 . 116.6(7) yes
O8 . N6 . C13 . 111.9(11) yes
O8 . N6 . C17 . 107.8(11) yes
C13 . N6 . C17 . 110.6(12) yes
O8 . N6 . C25 . 107.0(12) yes
C13 . N6 . C25 . 110.4(12) yes
C17 . N6 . C25 . 109.0(12) yes
N6 . O8 . I1 . 113.9(7) yes
I2 . O9 . I2 2_566 105.2(5) yes
O3 . N10 . C12 . 109.3(10) yes
O3 . N10 . C16 . 109.1(11) yes
C12 . N10 . C16 . 106.9(12) yes
O3 . N10 . C26 . 109.3(12) yes
C12 . N10 . C26 . 114.0(12) yes
C16 . N10 . C26 . 108.1(13) yes
C17 . C11 . C31 . 112.6(17) yes
C17 . C11 . H111 . 108.4 no
C31 . C11 . H111 . 107.3 no
C17 . C11 . H112 . 108.7 no
C31 . C11 . H112 . 110.0 no
H111 . C11 . H112 . 109.7 no
N10 . C12 . C19 . 119.4(13) yes
N10 . C12 . C28 . 120.3(13) yes
C19 . C12 . C28 . 120.3(15) yes
N6 . C13 . C14 . 117.2(15) yes
N6 . C13 . C20 . 121.7(15) yes
C14 . C13 . C20 . 121.0(17) yes
I1 . C14 . C13 . 123.2(13) yes
I1 . C14 . C24 . 116.7(13) yes
C13 . C14 . C24 . 119.9(18) yes
C18 . C15 . C19 . 117.7(15) yes
C18 . C15 . H151 . 121.2 no
C19 . C15 . H151 . 121.1 no
N10 . C16 . H161 . 108.9 no
N10 . C16 . H162 . 108.3 no
H161 . C16 . H162 . 109.9 no
N10 . C16 . H163 . 110.4 no
H161 . C16 . H163 . 109.6 no
H162 . C16 . H163 . 109.7 no
N6 . C17 . C11 . 116.4(13) yes
N6 . C17 . H171 . 107.5 no
C11 . C17 . H171 . 107.4 no
N6 . C17 . H172 . 108.2 no
C11 . C17 . H172 . 107.8 no
H171 . C17 . H172 . 109.5 no
C15 . C18 . C23 . 119.9(15) yes
C15 . C18 . H181 . 119.7 no
C23 . C18 . H181 . 120.3 no
C15 . C19 . I2 . 115.8(11) yes
C15 . C19 . C12 . 121.3(14) yes
I2 . C19 . C12 . 122.3(11) yes
C13 . C20 . C22 . 120.3(18) yes
C13 . C20 . H201 . 120.1 no
C22 . C20 . H201 . 119.6 no
C26 . C21 . C29 . 109.1(18) yes
C26 . C21 . H211 . 109.5 no
C29 . C21 . H211 . 109.3 no
C26 . C21 . H212 . 109.8 no
C29 . C21 . H212 . 109.7 no
H211 . C21 . H212 . 109.4 no
C20 . C22 . C27 . 119.3(17) yes
C20 . C22 . H221 . 121.6 no
C27 . C22 . H221 . 118.9 no
C18 . C23 . C28 . 121.8(17) yes
C18 . C23 . H231 . 118.6 no
C28 . C23 . H231 . 119.5 no
C14 . C24 . C27 . 118.2(18) yes
C14 . C24 . H241 . 121.0 no
C27 . C24 . H241 . 120.7 no
N6 . C25 . H251 . 108.6 no
N6 . C25 . H252 . 108.5 no
H251 . C25 . H252 . 109.3 no
N6 . C25 . H253 . 111.3 no
H251 . C25 . H253 . 109.8 no
H252 . C25 . H253 . 109.3 no
C21 . C26 . N10 . 112.1(14) yes
C21 . C26 . H261 . 108.0 no
N10 . C26 . H261 . 109.1 no
C21 . C26 . H262 . 108.6 no
N10 . C26 . H262 . 109.6 no
H261 . C26 . H262 . 109.5 no
C24 . C27 . C22 . 121.2(18) yes
C24 . C27 . H271 . 119.1 no
C22 . C27 . H271 . 119.5 no
C12 . C28 . C23 . 118.5(16) yes
C12 . C28 . H281 . 119.6 no
C23 . C28 . H281 . 121.9 no
C21 . C29 . C32 . 127(3) yes
C21 . C29 . H291 . 106.8 no
C32 . C29 . H291 . 105.3 no
C21 . C29 . H292 . 105.4 no
C32 . C29 . H292 . 102.0 no
H291 . C29 . H292 . 109.5 no
C31 . C30 . H301 . 111.9 no
C31 . C30 . H302 . 108.5 no
H301 . C30 . H302 . 109.5 no
C31 . C30 . H303 . 107.7 no
H301 . C30 . H303 . 109.6 no
H302 . C30 . H303 . 109.6 no
C11 . C31 . C30 . 120(2) yes
C11 . C31 . H311 . 107.9 no
C30 . C31 . H311 . 106.9 no
C11 . C31 . H312 . 105.5 no
C30 . C31 . H312 . 107.0 no
H311 . C31 . H312 . 109.9 no
C29 . C32 . H321 . 116.7 no
C29 . C32 . H322 . 104.1 no
H321 . C32 . H322 . 109.5 no
C29 . C32 . H323 . 107.4 no
H321 . C32 . H323 . 109.5 no
H322 . C32 . H323 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C16 . H161 . O8 1_545 140 0.96 2.56 3.35(3) yes
C16 . H163 . O4 2_556 161 0.96 2.42 3.34(3) yes
C18 . H181 . O3 1_655 139 0.93 2.59 3.35(3) yes
C25 . H252 . O4 2_666 139 0.96 2.53 3.31(3) yes
C26 . H261 . O8 1_545 150 0.97 2.50 3.37(3) yes