# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FIO3_CH2Cl2
_audit_block_doi                 10.5517/cc14n3ws
_database_code_depnum_ccdc_archive 'CCDC 1062025'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (FIO)3:CH2Cl2
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H21 F3 N6 O6, C H2 Cl2'
_chemical_formula_sum            'C40 H23 Cl2 F3 N6 O6'
_chemical_formula_weight         811.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.6181(1)
_cell_length_b                   12.7879(1)
_cell_length_c                   24.7200(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.4752(6)
_cell_angle_gamma                90.00
_cell_volume                     3671.46(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9159
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      63.1

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    2.228
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.3792
_exptl_absorpt_correction_T_max  0.8779
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         9159
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_reflns_number            20793
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         63.23
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        62.50
_diffrn_measured_fraction_theta_full 1.000
_reflns_number_total             5942
_reflns_number_gt                5051
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.0418P)²+0.9316P] where P=(Fo²+2Fc²)/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       0.00071(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5942
_refine_ls_number_parameters     526
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.032

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39811(10) 0.13438(10) 0.34042(5) 0.0547(3) Uani 1 1 d . . .
C1 C 0.34704(13) 0.12948(13) 0.29718(7) 0.0418(4) Uani 1 1 d . . .
N1 N 0.32934(11) 0.03297(11) 0.27025(5) 0.0429(3) Uani 1 1 d . . .
O2 O 0.39302(12) -0.13433(11) 0.28111(6) 0.0644(4) Uani 1 1 d . . .
C2 C 0.33964(14) -0.06207(13) 0.29937(7) 0.0451(4) Uani 1 1 d . . .
O3 O -0.07120(11) 0.01081(10) 0.43323(6) 0.0589(3) Uani 1 1 d . . .
C3 C 0.02209(14) 0.04641(13) 0.42153(6) 0.0432(4) Uani 1 1 d . . .
N2 N 0.03756(11) 0.15388(11) 0.41963(5) 0.0421(3) Uani 1 1 d . . .
O4 O -0.07322(12) 0.27901(11) 0.46002(5) 0.0608(3) Uani 1 1 d . . .
C4 C -0.06382(14) 0.21841(13) 0.42331(7) 0.0440(4) Uani 1 1 d . . .
O5 O -0.23547(10) 0.13149(11) 0.19470(5) 0.0563(3) Uani 1 1 d . . .
C5 C -0.17050(14) 0.17538(13) 0.22609(7) 0.0429(4) Uani 1 1 d . . .
N3 N -0.05907(11) 0.20569(11) 0.21054(5) 0.0416(3) Uani 1 1 d . . .
O6 O -0.07112(10) 0.37387(9) 0.24231(5) 0.0523(3) Uani 1 1 d . . .
C6 C -0.01032(14) 0.30166(12) 0.22991(6) 0.0404(4) Uani 1 1 d . . .
C11 C 0.11705(13) 0.30405(12) 0.23823(6) 0.0386(3) Uani 1 1 d . . .
C12 C 0.17738(13) 0.21435(12) 0.25289(6) 0.0386(3) Uani 1 1 d . . .
H12 H 0.1416 0.1494 0.2505 0.046 Uiso 1 1 calc R . .
C13 C 0.29123(13) 0.22154(13) 0.27114(6) 0.0398(4) Uani 1 1 d . . .
C14 C 0.34701(14) 0.31760(14) 0.27096(7) 0.0471(4) Uani 1 1 d . . .
H14 H 0.4234 0.3226 0.2829 0.057 Uiso 1 1 calc R . .
C15 C 0.28875(15) 0.40591(14) 0.25302(7) 0.0507(4) Uani 1 1 d . . .
H15 H 0.3272 0.4695 0.2510 0.061 Uiso 1 1 calc R . .
C16 C 0.17376(15) 0.39967(13) 0.23808(7) 0.0464(4) Uani 1 1 d . . .
H16 H 0.1339 0.4599 0.2278 0.056 Uiso 1 1 calc R . .
C11A C 0.36019(14) 0.03311(13) 0.21431(7) 0.0452(4) Uani 1 1 d . . .
N12A N 0.45824(13) 0.08160(13) 0.20459(7) 0.0590(4) Uani 1 1 d . . .
C13A C 0.4881(2) 0.09033(19) 0.15310(10) 0.0735(6) Uani 1 1 d . . .
H13A H 0.5565 0.1239 0.1449 0.088 Uiso 1 1 calc R . .
C14A C 0.4202(2) 0.05101(18) 0.11218(9) 0.0725(6) Uani 1 1 d . . .
F14A F 0.45183(17) 0.06508(14) 0.06047(6) 0.1141(6) Uani 1 1 d . . .
C15A C 0.3212(2) -0.00254(19) 0.12217(9) 0.0733(6) Uani 1 1 d . . .
H15A H 0.2767 -0.0316 0.0942 0.088 Uiso 1 1 calc R . .
C16A C 0.28965(18) -0.01185(16) 0.17553(8) 0.0591(5) Uani 1 1 d . . .
H16A H 0.2231 -0.0473 0.1848 0.071 Uiso 1 1 calc R . .
C21 C 0.27529(14) -0.07054(13) 0.35031(7) 0.0423(4) Uani 1 1 d . . .
C22 C 0.18510(13) -0.00416(12) 0.36287(6) 0.0400(4) Uani 1 1 d . . .
H22 H 0.1672 0.0521 0.3404 0.048 Uiso 1 1 calc R . .
C23 C 0.12186(14) -0.02136(12) 0.40863(6) 0.0417(4) Uani 1 1 d . . .
C24 C 0.14776(18) -0.10601(15) 0.44195(8) 0.0578(5) Uani 1 1 d . . .
H24 H 0.1040 -0.1189 0.4722 0.069 Uiso 1 1 calc R . .
C25 C 0.2381(2) -0.17063(16) 0.43019(8) 0.0680(6) Uani 1 1 d . . .
H25 H 0.2565 -0.2263 0.4530 0.082 Uiso 1 1 calc R . .
C26 C 0.30155(17) -0.15351(15) 0.38469(8) 0.0569(5) Uani 1 1 d . . .
H26 H 0.3624 -0.1979 0.3770 0.068 Uiso 1 1 calc R . .
C21A C 0.14534(14) 0.20680(13) 0.42630(7) 0.0433(4) Uani 1 1 d . . .
N22A N 0.15312(14) 0.29216(12) 0.39604(6) 0.0552(4) Uani 1 1 d . . .
C23A C 0.2517(2) 0.34576(17) 0.40025(9) 0.0693(6) Uani 1 1 d . . .
H23A H 0.2596 0.4069 0.3803 0.083 Uiso 1 1 calc R . .
C24A C 0.34120(19) 0.31331(19) 0.43305(10) 0.0721(6) Uani 1 1 d . . .
F24A F 0.44077(14) 0.36738(15) 0.43339(8) 0.1193(6) Uani 1 1 d . . .
C25A C 0.33232(18) 0.22691(19) 0.46453(9) 0.0685(6) Uani 1 1 d . . .
H25A H 0.3932 0.2052 0.4870 0.082 Uiso 1 1 calc R . .
C26A C 0.22998(15) 0.17257(15) 0.46207(7) 0.0524(4) Uani 1 1 d . . .
H26A H 0.2184 0.1145 0.4839 0.063 Uiso 1 1 calc R . .
C31 C -0.15054(14) 0.20875(13) 0.37854(7) 0.0426(4) Uani 1 1 d . . .
C32 C -0.11750(13) 0.19320(13) 0.32576(7) 0.0421(4) Uani 1 1 d . . .
H32 H -0.0401 0.1838 0.3183 0.051 Uiso 1 1 calc R . .
C33 C -0.19976(14) 0.19158(13) 0.28388(7) 0.0419(4) Uani 1 1 d . . .
C34 C -0.31569(14) 0.20014(14) 0.29625(8) 0.0497(4) Uani 1 1 d . . .
H34 H -0.3717 0.1945 0.2689 0.060 Uiso 1 1 calc R . .
C35 C -0.34795(15) 0.21696(16) 0.34880(8) 0.0561(5) Uani 1 1 d . . .
H35 H -0.4255 0.2240 0.3566 0.067 Uiso 1 1 calc R . .
C36 C -0.26584(15) 0.22333(15) 0.38985(8) 0.0515(4) Uani 1 1 d . . .
H36 H -0.2876 0.2374 0.4251 0.062 Uiso 1 1 calc R . .
C31A C -0.01636(14) 0.16684(13) 0.16034(6) 0.0427(4) Uani 1 1 d . . .
N32A N 0.02932(13) 0.23910(12) 0.12933(6) 0.0529(4) Uani 1 1 d . . .
C33A C 0.07231(19) 0.20785(18) 0.08229(8) 0.0630(5) Uani 1 1 d . . .
H33A H 0.1068 0.2568 0.0601 0.076 Uiso 1 1 calc R . .
C34A C 0.06680(18) 0.10663(19) 0.06621(7) 0.0632(5) Uani 1 1 d . . .
F34A F 0.11221(13) 0.07927(13) 0.01835(5) 0.0920(4) Uani 1 1 d . . .
C35A C 0.01800(19) 0.03172(17) 0.09759(8) 0.0656(5) Uani 1 1 d . . .
H35A H 0.0129 -0.0374 0.0861 0.079 Uiso 1 1 calc R . .
C36A C -0.02349(17) 0.06221(15) 0.14691(8) 0.0558(5) Uani 1 1 d . . .
H36A H -0.0552 0.0139 0.1704 0.067 Uiso 1 1 calc R . .
Cl1S Cl 0.35705(11) 0.31983(7) 0.11648(4) 0.0963(5) Uani 0.904(6) 1 d P A 1
Cl2S Cl 0.40790(13) 0.50390(9) 0.05297(5) 0.1078(5) Uani 0.904(6) 1 d P A 1
C1S C 0.3521(3) 0.4563(2) 0.11231(11) 0.0879(10) Uani 0.904(6) 1 d P A 1
H1S1 H 0.2728 0.4791 0.1148 0.106 Uiso 0.904(6) 1 calc PR A 1
H1S2 H 0.3951 0.4858 0.1428 0.106 Uiso 0.904(6) 1 calc PR A 1
Cl3S Cl 0.307(4) 0.340(3) 0.1077(13) 0.279(12) Uiso 0.096(6) 1 d PD A 2
C2S C 0.404(7) 0.438(6) 0.1153(17) 0.279(12) Uiso 0.096(6) 1 d PD A 2
H2S1 H 0.3737 0.4926 0.1382 0.335 Uiso 0.096(6) 1 calc PR A 2
H2S2 H 0.4749 0.4119 0.1322 0.335 Uiso 0.096(6) 1 calc PR A 2
Cl4S Cl 0.431(3) 0.487(3) 0.0534(15) 0.279(12) Uiso 0.096(6) 1 d PD A 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
O1 C1 1.211(2) . ?
C1 N1 1.415(2) . ?
C1 C13 1.483(2) . ?
N1 C2 1.416(2) . ?
N1 C11A 1.437(2) . ?
O2 C2 1.207(2) . ?
C2 C21 1.485(2) . ?
O3 C3 1.217(2) . ?
C3 N2 1.387(2) . ?
C3 C23 1.488(2) . ?
N2 C21A 1.429(2) . ?
N2 C4 1.443(2) . ?
O4 C4 1.200(2) . ?
C4 C31 1.482(2) . ?
O5 C5 1.207(2) . ?
C5 N3 1.414(2) . ?
C5 C33 1.491(2) . ?
N3 C6 1.429(2) . ?
N3 C31A 1.437(2) . ?
O6 C6 1.207(2) . ?
C6 C11 1.489(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.389(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(2) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11A N12A 1.324(2) . ?
C11A C16A 1.372(3) . ?
N12A C13A 1.332(3) . ?
C13A C14A 1.363(3) . ?
C13A H13A 0.9300 . ?
C14A F14A 1.351(2) . ?
C14A C15A 1.367(3) . ?
C15A C16A 1.383(3) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21 C26 1.388(2) . ?
C21 C22 1.390(2) . ?
C22 C23 1.382(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(2) . ?
C24 C25 1.373(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21A N22A 1.328(2) . ?
C21A C26A 1.377(3) . ?
N22A C23A 1.337(3) . ?
C23A C24A 1.366(3) . ?
C23A H23A 0.9300 . ?
C24A F24A 1.348(2) . ?
C24A C25A 1.357(3) . ?
C25A C26A 1.377(3) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
C31 C32 1.384(2) . ?
C31 C36 1.388(2) . ?
C32 C33 1.391(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.393(2) . ?
C34 C35 1.378(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.377(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C31A N32A 1.321(2) . ?
C31A C36A 1.381(3) . ?
N32A C33A 1.338(2) . ?
C33A C34A 1.355(3) . ?
C33A H33A 0.9300 . ?
C34A F34A 1.354(2) . ?
C34A C35A 1.365(3) . ?
C35A C36A 1.379(3) . ?
C35A H35A 0.9300 . ?
C36A H36A 0.9300 . ?
Cl1S C1S 1.749(3) . ?
Cl2S C1S 1.730(3) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?
Cl3S C2S 1.69(2) . ?
C2S Cl4S 1.69(2) . ?
C2S H2S1 0.9700 . ?
C2S H2S2 0.9700 . ?

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
O1 C1 N1 121.50(16) . . ?
O1 C1 C13 122.75(15) . . ?
N1 C1 C13 115.58(14) . . ?
C1 N1 C2 120.01(14) . . ?
C1 N1 C11A 114.50(13) . . ?
C2 N1 C11A 118.05(13) . . ?
O2 C2 N1 120.29(16) . . ?
O2 C2 C21 122.43(16) . . ?
N1 C2 C21 117.12(14) . . ?
O3 C3 N2 119.71(16) . . ?
O3 C3 C23 122.42(16) . . ?
N2 C3 C23 117.87(14) . . ?
C3 N2 C21A 125.39(14) . . ?
C3 N2 C4 117.25(13) . . ?
C21A N2 C4 115.86(13) . . ?
O4 C4 N2 120.47(16) . . ?
O4 C4 C31 123.02(16) . . ?
N2 C4 C31 116.45(14) . . ?
O5 C5 N3 120.97(15) . . ?
O5 C5 C33 121.74(15) . . ?
N3 C5 C33 117.08(14) . . ?
C5 N3 C6 120.14(14) . . ?
C5 N3 C31A 118.62(13) . . ?
C6 N3 C31A 116.32(13) . . ?
O6 C6 N3 120.83(15) . . ?
O6 C6 C11 122.37(15) . . ?
N3 C6 C11 116.60(14) . . ?
C12 C11 C16 119.47(15) . . ?
C12 C11 C6 120.84(14) . . ?
C16 C11 C6 119.17(14) . . ?
C11 C12 C13 120.02(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.86(15) . . ?
C14 C13 C1 120.31(15) . . ?
C12 C13 C1 119.36(14) . . ?
C15 C14 C13 119.89(16) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.07(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.43(16) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N12A C11A C16A 124.79(17) . . ?
N12A C11A N1 114.34(15) . . ?
C16A C11A N1 120.84(16) . . ?
C11A N12A C13A 117.31(19) . . ?
N12A C13A C14A 121.2(2) . . ?
N12A C13A H13A 119.4 . . ?
C14A C13A H13A 119.4 . . ?
F14A C14A C13A 119.1(2) . . ?
F14A C14A C15A 119.2(2) . . ?
C13A C14A C15A 121.64(19) . . ?
C14A C15A C16A 117.4(2) . . ?
C14A C15A H15A 121.3 . . ?
C16A C15A H15A 121.3 . . ?
C11A C16A C15A 117.5(2) . . ?
C11A C16A H16A 121.2 . . ?
C15A C16A H16A 121.2 . . ?
C26 C21 C22 119.02(16) . . ?
C26 C21 C2 117.86(15) . . ?
C22 C21 C2 122.95(15) . . ?
C23 C22 C21 120.36(15) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.85(16) . . ?
C22 C23 C3 121.07(14) . . ?
C24 C23 C3 119.01(15) . . ?
C25 C24 C23 119.93(18) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.34(18) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.47(18) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
N22A C21A C26A 124.43(17) . . ?
N22A C21A N2 113.35(15) . . ?
C26A C21A N2 122.19(15) . . ?
C21A N22A C23A 116.64(18) . . ?
N22A C23A C24A 121.9(2) . . ?
N22A C23A H23A 119.1 . . ?
C24A C23A H23A 119.1 . . ?
F24A C24A C25A 119.5(2) . . ?
F24A C24A C23A 119.2(2) . . ?
C25A C24A C23A 121.31(19) . . ?
C24A C25A C26A 117.6(2) . . ?
C24A C25A H25A 121.2 . . ?
C26A C25A H25A 121.2 . . ?
C21A C26A C25A 117.99(19) . . ?
C21A C26A H26A 121.0 . . ?
C25A C26A H26A 121.0 . . ?
C32 C31 C36 120.12(16) . . ?
C32 C31 C4 121.07(14) . . ?
C36 C31 C4 118.64(15) . . ?
C31 C32 C33 120.13(15) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C34 119.02(16) . . ?
C32 C33 C5 123.08(14) . . ?
C34 C33 C5 117.83(15) . . ?
C35 C34 C33 120.48(16) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 120.25(16) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C31 119.83(17) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
N32A C31A C36A 124.13(16) . . ?
N32A C31A N3 114.35(15) . . ?
C36A C31A N3 121.52(15) . . ?
C31A N32A C33A 117.38(17) . . ?
N32A C33A C34A 121.62(19) . . ?
N32A C33A H33A 119.2 . . ?
C34A C33A H33A 119.2 . . ?
F34A C34A C33A 119.1(2) . . ?
F34A C34A C35A 119.5(2) . . ?
C33A C34A C35A 121.38(18) . . ?
C34A C35A C36A 117.64(19) . . ?
C34A C35A H35A 121.2 . . ?
C36A C35A H35A 121.2 . . ?
C35A C36A C31A 117.81(18) . . ?
C35A C36A H36A 121.1 . . ?
C31A C36A H36A 121.1 . . ?
Cl2S C1S Cl1S 112.87(16) . . ?
Cl2S C1S H1S1 109.0 . . ?
Cl1S C1S H1S1 109.0 . . ?
Cl2S C1S H1S2 109.0 . . ?
Cl1S C1S H1S2 109.0 . . ?
H1S1 C1S H1S2 107.8 . . ?
Cl4S C2S Cl3S 108(2) . . ?
Cl4S C2S H2S1 110.0 . . ?
Cl3S C2S H2S1 110.0 . . ?
Cl4S C2S H2S2 110.0 . . ?
Cl3S C2S H2S2 110.0 . . ?
H2S1 C2S H2S2 108.4 . . ?

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
O1 C1 N1 C2 18.8(2) . . . . ?
C13 C1 N1 C2 -156.51(14) . . . . ?
O1 C1 N1 C11A -130.50(16) . . . . ?
C13 C1 N1 C11A 54.17(18) . . . . ?
C1 N1 C2 O2 -134.25(17) . . . . ?
C11A N1 C2 O2 14.0(2) . . . . ?
C1 N1 C2 C21 50.2(2) . . . . ?
C11A N1 C2 C21 -161.52(14) . . . . ?
O3 C3 N2 C21A 155.73(16) . . . . ?
C23 C3 N2 C21A -24.6(2) . . . . ?
O3 C3 N2 C4 -9.7(2) . . . . ?
C23 C3 N2 C4 169.98(14) . . . . ?
C3 N2 C4 O4 118.66(18) . . . . ?
C21A N2 C4 O4 -48.1(2) . . . . ?
C3 N2 C4 C31 -64.12(19) . . . . ?
C21A N2 C4 C31 129.08(15) . . . . ?
O5 C5 N3 C6 143.01(16) . . . . ?
C33 C5 N3 C6 -42.2(2) . . . . ?
O5 C5 N3 C31A -11.3(2) . . . . ?
C33 C5 N3 C31A 163.53(14) . . . . ?
C5 N3 C6 O6 -26.8(2) . . . . ?
C31A N3 C6 O6 128.00(16) . . . . ?
C5 N3 C6 C11 148.14(14) . . . . ?
C31A N3 C6 C11 -57.02(18) . . . . ?
O6 C6 C11 C12 144.00(16) . . . . ?
N3 C6 C11 C12 -30.9(2) . . . . ?
O6 C6 C11 C16 -27.7(2) . . . . ?
N3 C6 C11 C16 157.40(15) . . . . ?
C16 C11 C12 C13 4.8(2) . . . . ?
C6 C11 C12 C13 -166.88(14) . . . . ?
C11 C12 C13 C14 -4.7(2) . . . . ?
C11 C12 C13 C1 167.45(14) . . . . ?
O1 C1 C13 C14 42.6(2) . . . . ?
N1 C1 C13 C14 -142.09(15) . . . . ?
O1 C1 C13 C12 -129.43(17) . . . . ?
N1 C1 C13 C12 45.8(2) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C1 C13 C14 C15 -171.52(16) . . . . ?
C13 C14 C15 C16 3.5(3) . . . . ?
C14 C15 C16 C11 -3.3(3) . . . . ?
C12 C11 C16 C15 -0.8(2) . . . . ?
C6 C11 C16 C15 171.00(16) . . . . ?
C1 N1 C11A N12A 42.7(2) . . . . ?
C2 N1 C11A N12A -107.25(17) . . . . ?
C1 N1 C11A C16A -135.69(17) . . . . ?
C2 N1 C11A C16A 74.3(2) . . . . ?
C16A C11A N12A C13A 2.5(3) . . . . ?
N1 C11A N12A C13A -175.84(17) . . . . ?
C11A N12A C13A C14A 0.1(3) . . . . ?
N12A C13A C14A F14A 177.6(2) . . . . ?
N12A C13A C14A C15A -2.6(4) . . . . ?
F14A C14A C15A C16A -177.65(19) . . . . ?
C13A C14A C15A C16A 2.6(3) . . . . ?
N12A C11A C16A C15A -2.5(3) . . . . ?
N1 C11A C16A C15A 175.75(17) . . . . ?
C14A C15A C16A C11A -0.1(3) . . . . ?
O2 C2 C21 C26 17.0(3) . . . . ?
N1 C2 C21 C26 -167.55(16) . . . . ?
O2 C2 C21 C22 -158.08(17) . . . . ?
N1 C2 C21 C22 17.3(2) . . . . ?
C26 C21 C22 C23 -0.7(2) . . . . ?
C2 C21 C22 C23 174.36(15) . . . . ?
C21 C22 C23 C24 -0.7(2) . . . . ?
C21 C22 C23 C3 -177.55(15) . . . . ?
O3 C3 C23 C22 130.82(18) . . . . ?
N2 C3 C23 C22 -48.8(2) . . . . ?
O3 C3 C23 C24 -46.1(2) . . . . ?
N2 C3 C23 C24 134.27(17) . . . . ?
C22 C23 C24 C25 1.8(3) . . . . ?
C3 C23 C24 C25 178.78(19) . . . . ?
C23 C24 C25 C26 -1.6(3) . . . . ?
C24 C25 C26 C21 0.3(3) . . . . ?
C22 C21 C26 C25 0.9(3) . . . . ?
C2 C21 C26 C25 -174.40(18) . . . . ?
C3 N2 C21A N22A 145.24(16) . . . . ?
C4 N2 C21A N22A -49.18(19) . . . . ?
C3 N2 C21A C26A -36.5(2) . . . . ?
C4 N2 C21A C26A 129.03(17) . . . . ?
C26A C21A N22A C23A 1.8(3) . . . . ?
N2 C21A N22A C23A 179.93(16) . . . . ?
C21A N22A C23A C24A 1.5(3) . . . . ?
N22A C23A C24A F24A 176.36(19) . . . . ?
N22A C23A C24A C25A -2.5(3) . . . . ?
F24A C24A C25A C26A -178.57(19) . . . . ?
C23A C24A C25A C26A 0.3(3) . . . . ?
N22A C21A C26A C25A -3.9(3) . . . . ?
N2 C21A C26A C25A 178.11(17) . . . . ?
C24A C25A C26A C21A 2.6(3) . . . . ?
O4 C4 C31 C32 140.87(18) . . . . ?
N2 C4 C31 C32 -36.3(2) . . . . ?
O4 C4 C31 C36 -34.4(3) . . . . ?
N2 C4 C31 C36 148.44(16) . . . . ?
C36 C31 C32 C33 -0.3(3) . . . . ?
C4 C31 C32 C33 -175.55(15) . . . . ?
C31 C32 C33 C34 -3.4(2) . . . . ?
C31 C32 C33 C5 179.91(15) . . . . ?
O5 C5 C33 C32 148.06(17) . . . . ?
N3 C5 C33 C32 -26.7(2) . . . . ?
O5 C5 C33 C34 -28.6(2) . . . . ?
N3 C5 C33 C34 156.60(15) . . . . ?
C32 C33 C34 C35 4.3(3) . . . . ?
C5 C33 C34 C35 -178.88(16) . . . . ?
C33 C34 C35 C36 -1.3(3) . . . . ?
C34 C35 C36 C31 -2.5(3) . . . . ?
C32 C31 C36 C35 3.3(3) . . . . ?
C4 C31 C36 C35 178.64(17) . . . . ?
C5 N3 C31A N32A 132.13(15) . . . . ?
C6 N3 C31A N32A -23.1(2) . . . . ?
C5 N3 C31A C36A -48.0(2) . . . . ?
C6 N3 C31A C36A 156.72(16) . . . . ?
C36A C31A N32A C33A -0.8(3) . . . . ?
N3 C31A N32A C33A 179.04(16) . . . . ?
C31A N32A C33A C34A 1.7(3) . . . . ?
N32A C33A C34A F34A -179.67(18) . . . . ?
N32A C33A C34A C35A -0.6(3) . . . . ?
F34A C34A C35A C36A 177.69(19) . . . . ?
C33A C34A C35A C36A -1.3(3) . . . . ?
C34A C35A C36A C31A 2.1(3) . . . . ?
N32A C31A C36A C35A -1.1(3) . . . . ?
N3 C31A C36A C35A 179.04(17) . . . . ?


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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
#   C24  H24  O4    0.93      2.68      3.410(2)  137       3_556  yes
C34 H34 O2 0.93 2.52 2.976(2) 110 2 yes
C35 H35 O1 0.93 2.37 3.135(2) 139 1_455 yes
C12 H12 N3 0.93 2.61 2.917(2) 100 . yes
C22 H22 N1 0.93 2.60 2.911(2) 100 . yes
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FIO3_DMSO
_audit_block_doi                 10.5517/cc14n3xt
_database_code_depnum_ccdc_archive 'CCDC 1062026'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (FIO)3:DMSO
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H21 F3 N6 O6, C2 H6 O S'
_chemical_formula_sum            'C41 H27 F3 N6 O7 S'
_chemical_formula_weight         804.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   11.4994(1)
_cell_length_b                   18.9382(1)
_cell_length_c                   17.4326(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.599(2)
_cell_angle_gamma                90.00
_cell_volume                     3794.96(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    11255
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      63.11

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         22562
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_reflns_number            22562
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         63.20
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        62.50
_diffrn_measured_fraction_theta_full 1.000
_reflns_number_total             6142
_reflns_number_gt                5343
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.0544P)²+0.826P] where P=(Fo²+2Fc²)/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       0.00064(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6142
_refine_ls_number_parameters     564
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.031

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
F14A F 0.74629(14) -0.00112(8) 0.24214(9) 0.1073(5) Uani 1 1 d . . .
F24A F 0.05527(16) 0.46207(10) 0.11337(9) 0.1201(6) Uani 1 1 d . . .
F34A F 0.97555(17) 0.03386(8) 0.10735(9) 0.1159(6) Uani 1 1 d . . .
O1 O 0.31205(10) 0.24593(7) 0.12843(7) 0.0570(3) Uani 1 1 d . . .
C1 C 0.40805(14) 0.22503(8) 0.11488(8) 0.0425(4) Uani 1 1 d . . .
N1 N 0.42503(11) 0.15588(7) 0.08419(7) 0.0418(3) Uani 1 1 d . . .
O2 O 0.31923(11) 0.06060(7) 0.04411(8) 0.0636(3) Uani 1 1 d . . .
C2 C 0.33737(13) 0.12366(8) 0.03889(9) 0.0442(4) Uani 1 1 d . . .
O3 O 0.35086(12) 0.32518(8) -0.21527(7) 0.0668(4) Uani 1 1 d . . .
C3 C 0.33074(14) 0.32398(9) -0.14791(9) 0.0469(4) Uani 1 1 d . . .
N2 N 0.36548(11) 0.37950(7) -0.09859(8) 0.0476(3) Uani 1 1 d . . .
O4 O 0.43479(13) 0.49185(7) -0.10940(10) 0.0778(4) Uani 1 1 d . . .
C4 C 0.44682(15) 0.43018(9) -0.12371(10) 0.0529(4) Uani 1 1 d . . .
O5 O 0.84716(14) 0.23025(10) -0.15639(9) 0.0887(5) Uani 1 1 d . . .
C5 C 0.79312(15) 0.27135(12) -0.11716(11) 0.0621(5) Uani 1 1 d . . .
N3 N 0.78911(12) 0.26331(8) -0.03764(8) 0.0546(4) Uani 1 1 d . . .
O6 O 0.81980(12) 0.37919(8) -0.00348(9) 0.0748(4) Uani 1 1 d . . .
C6 C 0.77351(14) 0.32388(10) 0.01115(10) 0.0537(4) Uani 1 1 d . . .
C11 C 0.69111(14) 0.31603(9) 0.07437(9) 0.0463(4) Uani 1 1 d . . .
C12 C 0.60140(13) 0.26659(8) 0.07087(9) 0.0430(4) Uani 1 1 d . . .
H12 H 0.6000 0.2320 0.0329 0.052 Uiso 1 1 calc R . .
C13 C 0.51409(13) 0.26911(8) 0.12425(9) 0.0413(3) Uani 1 1 d . . .
C14 C 0.51939(16) 0.31860(9) 0.18311(9) 0.0511(4) Uani 1 1 d . . .
H14 H 0.4609 0.3203 0.2189 0.061 Uiso 1 1 calc R . .
C15 C 0.61114(18) 0.36508(9) 0.18845(10) 0.0589(5) Uani 1 1 d . . .
H15 H 0.6164 0.3968 0.2292 0.071 Uiso 1 1 calc R . .
C16 C 0.69538(16) 0.36485(9) 0.13363(11) 0.0559(4) Uani 1 1 d . . .
H16 H 0.7555 0.3977 0.1365 0.067 Uiso 1 1 calc R . .
C11A C 0.51047(13) 0.11265(8) 0.12251(9) 0.0415(3) Uani 1 1 d . . .
N12A N 0.52218(12) 0.12368(7) 0.19725(7) 0.0468(3) Uani 1 1 d . . .
C13A C 0.60218(16) 0.08566(10) 0.23613(10) 0.0582(4) Uani 1 1 d . . .
H13A H 0.6133 0.0929 0.2886 0.070 Uiso 1 1 calc R . .
C14A C 0.66758(17) 0.03647(10) 0.19996(12) 0.0656(5) Uani 1 1 d . . .
C15A C 0.65504(17) 0.02409(11) 0.12327(13) 0.0660(5) Uani 1 1 d . . .
H15A H 0.6990 -0.0102 0.0993 0.079 Uiso 1 1 calc R . .
C16A C 0.57500(15) 0.06415(10) 0.08247(10) 0.0539(4) Uani 1 1 d . . .
H16A H 0.5646 0.0588 0.0297 0.065 Uiso 1 1 calc R . .
C21 C 0.27555(13) 0.16815(8) -0.01947(9) 0.0423(3) Uani 1 1 d . . .
C22 C 0.32499(13) 0.22861(8) -0.04985(9) 0.0428(4) Uani 1 1 d . . .
H22 H 0.3947 0.2459 -0.0290 0.051 Uiso 1 1 calc R . .
C23 C 0.27103(13) 0.26326(8) -0.11105(9) 0.0433(4) Uani 1 1 d . . .
C24 C 0.16631(15) 0.23831(10) -0.14138(10) 0.0539(4) Uani 1 1 d . . .
H24 H 0.1307 0.2609 -0.1832 0.065 Uiso 1 1 calc R . .
C25 C 0.11500(15) 0.17990(10) -0.10953(11) 0.0573(4) Uani 1 1 d . . .
H25 H 0.0431 0.1644 -0.1285 0.069 Uiso 1 1 calc R . .
C26 C 0.16961(14) 0.14440(9) -0.04971(10) 0.0503(4) Uani 1 1 d . . .
H26 H 0.1353 0.1043 -0.0295 0.060 Uiso 1 1 calc R . .
C21A C 0.28715(14) 0.40147(9) -0.04048(9) 0.0482(4) Uani 1 1 d . . .
N22A N 0.17577(12) 0.40069(8) -0.06116(8) 0.0558(4) Uani 1 1 d . . .
C23A C 0.09994(18) 0.41991(12) -0.00805(12) 0.0695(5) Uani 1 1 d . . .
H23A H 0.0207 0.4183 -0.0200 0.083 Uiso 1 1 calc R . .
C24A C 0.1360(2) 0.44152(13) 0.06244(13) 0.0765(6) Uani 1 1 d . . .
C25A C 0.2504(2) 0.44362(14) 0.08361(13) 0.0846(7) Uani 1 1 d . . .
H25A H 0.2744 0.4590 0.1322 0.101 Uiso 1 1 calc R . .
C26A C 0.32986(19) 0.42211(11) 0.03045(11) 0.0671(5) Uani 1 1 d . . .
H26A H 0.4092 0.4216 0.0422 0.081 Uiso 1 1 calc R . .
C31 C 0.55283(14) 0.40290(9) -0.16031(10) 0.0513(4) Uani 1 1 d . . .
C32 C 0.61538(14) 0.34879(10) -0.12533(10) 0.0527(4) Uani 1 1 d . . .
H32 H 0.5851 0.3253 -0.0835 0.063 Uiso 1 1 calc R . .
C33 C 0.72323(15) 0.32949(11) -0.15247(10) 0.0559(4) Uani 1 1 d . . .
C34 C 0.76452(17) 0.36269(12) -0.21719(11) 0.0653(5) Uani 1 1 d . . .
H34 H 0.8357 0.3493 -0.2366 0.078 Uiso 1 1 calc R . .
C35 C 0.70046(19) 0.41541(12) -0.25287(11) 0.0702(6) Uani 1 1 d . . .
H35 H 0.7279 0.4366 -0.2970 0.084 Uiso 1 1 calc R . .
C36 C 0.59650(18) 0.43687(11) -0.22379(11) 0.0623(5) Uani 1 1 d . . .
H36 H 0.5556 0.4740 -0.2466 0.075 Uiso 1 1 calc R . .
C31A C 0.83502(15) 0.20125(11) -0.00161(10) 0.0556(4) Uani 1 1 d . . .
N32A N 0.89649(15) 0.21267(10) 0.06240(10) 0.0714(5) Uani 1 1 d . . .
C33A C 0.9406(2) 0.15567(14) 0.09877(13) 0.0847(7) Uani 1 1 d . . .
H33A H 0.9821 0.1616 0.1449 0.102 Uiso 1 1 calc R . .
C34A C 0.9259(2) 0.08934(12) 0.06979(13) 0.0746(6) Uani 1 1 d . . .
C35A C 0.86319(19) 0.07790(12) 0.00417(13) 0.0726(6) Uani 1 1 d . . .
H35A H 0.8535 0.0326 -0.0157 0.087 Uiso 1 1 calc R . .
C36A C 0.81428(17) 0.13540(12) -0.03212(12) 0.0666(5) Uani 1 1 d . . .
H36A H 0.7681 0.1299 -0.0764 0.080 Uiso 1 1 calc R . .
S1S S 0.51405(8) 0.13740(5) -0.17839(6) 0.0734(2) Uani 0.77 1 d P A -1
O1S O 0.5656(5) 0.1784(3) -0.1134(4) 0.0792(12) Uani 0.77 1 d P A -1
C1S C 0.5367(6) 0.1910(3) -0.2585(4) 0.1180(19) Uani 0.77 1 d P A -1
H1S1 H 0.4980 0.2355 -0.2520 0.177 Uiso 0.77 1 calc PR A -1
H1S2 H 0.5058 0.1681 -0.3038 0.177 Uiso 0.77 1 calc PR A -1
H1S3 H 0.6185 0.1989 -0.2637 0.177 Uiso 0.77 1 calc PR A -1
C2S C 0.6135(3) 0.06876(16) -0.19921(18) 0.0825(9) Uani 0.77 1 d P A -1
H2S1 H 0.6209 0.0376 -0.1559 0.124 Uiso 0.77 1 calc PR A -1
H2S2 H 0.6880 0.0888 -0.2097 0.124 Uiso 0.77 1 calc PR A -1
H2S3 H 0.5853 0.0428 -0.2432 0.124 Uiso 0.77 1 calc PR A -1
S1T S 0.5622(9) 0.1537(7) -0.1963(5) 0.237(5) Uani 0.23 1 d PDU B -2
O1T O 0.561(3) 0.1627(16) -0.109(2) 0.130(9) Uani 0.23 1 d PU B -2
C1T C 0.4242(15) 0.1382(13) -0.2305(13) 0.171(7) Uani 0.23 1 d PDU B -2
H1T1 H 0.3982 0.0932 -0.2123 0.256 Uiso 0.23 1 calc PR B -2
H1T2 H 0.4235 0.1380 -0.2856 0.256 Uiso 0.23 1 calc PR B -2
H1T3 H 0.3734 0.1746 -0.2129 0.256 Uiso 0.23 1 calc PR B -2
C2T C 0.593(2) 0.1993(15) -0.2708(13) 0.154(9) Uani 0.23 1 d PDU B -2
H2T1 H 0.5751 0.2480 -0.2621 0.232 Uiso 0.23 1 calc PR B -2
H2T2 H 0.5486 0.1823 -0.3144 0.232 Uiso 0.23 1 calc PR B -2
H2T3 H 0.6747 0.1946 -0.2805 0.232 Uiso 0.23 1 calc PR B -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
F14A C14A 1.353(2) . ?
F24A C24A 1.359(3) . ?
F34A C34A 1.356(2) . ?
O1 C1 1.2024(19) . ?
C1 N1 1.430(2) . ?
C1 C13 1.483(2) . ?
N1 C2 1.403(2) . ?
N1 C11A 1.4301(19) . ?
O2 C2 1.216(2) . ?
C2 C21 1.487(2) . ?
O3 C3 1.203(2) . ?
C3 N2 1.409(2) . ?
C3 C23 1.494(2) . ?
N2 C4 1.418(2) . ?
N2 C21A 1.436(2) . ?
O4 C4 1.203(2) . ?
C4 C31 1.484(3) . ?
O5 C5 1.218(2) . ?
C5 N3 1.397(2) . ?
C5 C33 1.486(3) . ?
N3 C31A 1.427(2) . ?
N3 C6 1.442(2) . ?
O6 C6 1.206(2) . ?
C6 C11 1.481(2) . ?
C11 C16 1.386(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(2) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11A N12A 1.323(2) . ?
C11A C16A 1.382(2) . ?
N12A C13A 1.338(2) . ?
C13A C14A 1.363(3) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.361(3) . ?
C15A C16A 1.376(3) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21 C26 1.389(2) . ?
C21 C22 1.390(2) . ?
C22 C23 1.385(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(2) . ?
C24 C25 1.378(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21A N22A 1.321(2) . ?
C21A C26A 1.374(3) . ?
N22A C23A 1.340(2) . ?
C23A C24A 1.349(3) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.357(4) . ?
C25A C26A 1.381(3) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
C31 C32 1.384(2) . ?
C31 C36 1.386(2) . ?
C32 C33 1.389(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.387(3) . ?
C34 C35 1.379(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C31A N32A 1.322(2) . ?
C31A C36A 1.374(3) . ?
N32A C33A 1.344(3) . ?
C33A C34A 1.363(3) . ?
C33A H33A 0.9300 . ?
C34A C35A 1.353(3) . ?
C35A C36A 1.372(3) . ?
C35A H35A 0.9300 . ?
C36A H36A 0.9300 . ?
S1S O1S 1.483(6) . ?
S1S C1S 1.752(5) . ?
S1S C2S 1.775(3) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?
S1T O1T 1.52(3) . ?
S1T C2T 1.61(2) . ?
S1T C1T 1.705(16) . ?
C1T H1T1 0.9600 . ?
C1T H1T2 0.9600 . ?
C1T H1T3 0.9600 . ?
C2T H2T1 0.9600 . ?
C2T H2T2 0.9600 . ?
C2T H2T3 0.9600 . ?

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
O1 C1 N1 120.70(15) . . ?
O1 C1 C13 123.35(15) . . ?
N1 C1 C13 115.86(13) . . ?
C2 N1 C11A 119.18(13) . . ?
C2 N1 C1 120.36(13) . . ?
C11A N1 C1 116.65(12) . . ?
O2 C2 N1 120.47(14) . . ?
O2 C2 C21 121.87(14) . . ?
N1 C2 C21 117.47(13) . . ?
O3 C3 N2 121.48(15) . . ?
O3 C3 C23 122.52(16) . . ?
N2 C3 C23 115.97(14) . . ?
C3 N2 C4 119.67(14) . . ?
C3 N2 C21A 118.30(13) . . ?
C4 N2 C21A 117.00(14) . . ?
O4 C4 N2 120.82(17) . . ?
O4 C4 C31 121.84(16) . . ?
N2 C4 C31 117.00(15) . . ?
O5 C5 N3 121.27(18) . . ?
O5 C5 C33 121.29(17) . . ?
N3 C5 C33 117.34(16) . . ?
C5 N3 C31A 120.31(15) . . ?
C5 N3 C6 120.44(16) . . ?
C31A N3 C6 116.50(14) . . ?
O6 C6 N3 120.23(17) . . ?
O6 C6 C11 122.69(17) . . ?
N3 C6 C11 116.86(15) . . ?
C16 C11 C12 119.46(16) . . ?
C16 C11 C6 118.53(15) . . ?
C12 C11 C6 121.54(15) . . ?
C13 C12 C11 119.72(15) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.02(15) . . ?
C12 C13 C1 120.96(14) . . ?
C14 C13 C1 118.68(14) . . ?
C15 C14 C13 119.96(16) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.22(16) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.48(16) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N12A C11A C16A 124.14(15) . . ?
N12A C11A N1 114.80(13) . . ?
C16A C11A N1 121.06(14) . . ?
C11A N12A C13A 117.62(15) . . ?
N12A C13A C14A 120.95(17) . . ?
N12A C13A H13A 119.5 . . ?
C14A C13A H13A 119.5 . . ?
F14A C14A C15A 119.62(19) . . ?
F14A C14A C13A 118.54(19) . . ?
C15A C14A C13A 121.83(17) . . ?
C14A C15A C16A 117.64(17) . . ?
C14A C15A H15A 121.2 . . ?
C16A C15A H15A 121.2 . . ?
C15A C16A C11A 117.79(17) . . ?
C15A C16A H16A 121.1 . . ?
C11A C16A H16A 121.1 . . ?
C26 C21 C22 119.08(15) . . ?
C26 C21 C2 118.30(14) . . ?
C22 C21 C2 122.33(13) . . ?
C23 C22 C21 120.32(14) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.92(15) . . ?
C22 C23 C3 119.66(14) . . ?
C24 C23 C3 120.25(14) . . ?
C25 C24 C23 119.86(16) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 120.37(15) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 120.40(16) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
N22A C21A C26A 124.62(17) . . ?
N22A C21A N2 115.26(14) . . ?
C26A C21A N2 120.11(16) . . ?
C21A N22A C23A 116.94(16) . . ?
N22A C23A C24A 121.5(2) . . ?
N22A C23A H23A 119.2 . . ?
C24A C23A H23A 119.2 . . ?
C23A C24A C25A 121.8(2) . . ?
C23A C24A F24A 118.9(2) . . ?
C25A C24A F24A 119.2(2) . . ?
C24A C25A C26A 117.6(2) . . ?
C24A C25A H25A 121.2 . . ?
C26A C25A H25A 121.2 . . ?
C21A C26A C25A 117.5(2) . . ?
C21A C26A H26A 121.3 . . ?
C25A C26A H26A 121.3 . . ?
C32 C31 C36 119.99(17) . . ?
C32 C31 C4 119.44(15) . . ?
C36 C31 C4 120.12(16) . . ?
C31 C32 C33 120.20(16) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C34 C33 C32 119.15(18) . . ?
C34 C33 C5 118.63(17) . . ?
C32 C33 C5 122.11(16) . . ?
C35 C34 C33 120.30(19) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C36 C35 C34 120.50(18) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C31 119.73(19) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
N32A C31A C36A 123.94(19) . . ?
N32A C31A N3 114.79(17) . . ?
C36A C31A N3 121.27(17) . . ?
C31A N32A C33A 116.90(19) . . ?
N32A C33A C34A 121.6(2) . . ?
N32A C33A H33A 119.2 . . ?
C34A C33A H33A 119.2 . . ?
C35A C34A F34A 119.5(2) . . ?
C35A C34A C33A 121.2(2) . . ?
F34A C34A C33A 119.3(2) . . ?
C34A C35A C36A 117.7(2) . . ?
C34A C35A H35A 121.1 . . ?
C36A C35A H35A 121.1 . . ?
C35A C36A C31A 118.51(19) . . ?
C35A C36A H36A 120.7 . . ?
C31A C36A H36A 120.7 . . ?
O1S S1S C1S 103.9(4) . . ?
O1S S1S C2S 107.1(3) . . ?
C1S S1S C2S 98.7(2) . . ?
O1T S1T C2T 138.7(18) . . ?
O1T S1T C1T 109.5(15) . . ?
C2T S1T C1T 92.0(13) . . ?
S1T C1T H1T1 109.5 . . ?
S1T C1T H1T2 109.5 . . ?
H1T1 C1T H1T2 109.5 . . ?
S1T C1T H1T3 109.5 . . ?
H1T1 C1T H1T3 109.5 . . ?
H1T2 C1T H1T3 109.5 . . ?
S1T C2T H2T1 109.5 . . ?
S1T C2T H2T2 109.5 . . ?
H2T1 C2T H2T2 109.5 . . ?
S1T C2T H2T3 109.5 . . ?
H2T1 C2T H2T3 109.5 . . ?
H2T2 C2T H2T3 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
O1 C1 N1 C2 28.2(2) . . . . ?
C13 C1 N1 C2 -148.52(14) . . . . ?
O1 C1 N1 C11A -129.62(15) . . . . ?
C13 C1 N1 C11A 53.62(17) . . . . ?
C11A N1 C2 O2 14.9(2) . . . . ?
C1 N1 C2 O2 -142.43(16) . . . . ?
C11A N1 C2 C21 -160.11(13) . . . . ?
C1 N1 C2 C21 42.6(2) . . . . ?
O3 C3 N2 C4 -14.0(2) . . . . ?
C23 C3 N2 C4 164.36(14) . . . . ?
O3 C3 N2 C21A 140.20(17) . . . . ?
C23 C3 N2 C21A -41.48(19) . . . . ?
C3 N2 C4 O4 139.24(18) . . . . ?
C21A N2 C4 O4 -15.2(2) . . . . ?
C3 N2 C4 C31 -47.4(2) . . . . ?
C21A N2 C4 C31 158.15(15) . . . . ?
O5 C5 N3 C31A -8.6(3) . . . . ?
C33 C5 N3 C31A 167.87(16) . . . . ?
O5 C5 N3 C6 151.9(2) . . . . ?
C33 C5 N3 C6 -31.6(2) . . . . ?
C5 N3 C6 O6 -38.0(2) . . . . ?
C31A N3 C6 O6 123.26(19) . . . . ?
C5 N3 C6 C11 136.76(16) . . . . ?
C31A N3 C6 C11 -62.0(2) . . . . ?
O6 C6 C11 C16 -21.8(3) . . . . ?
N3 C6 C11 C16 163.57(15) . . . . ?
O6 C6 C11 C12 150.28(18) . . . . ?
N3 C6 C11 C12 -24.4(2) . . . . ?
C16 C11 C12 C13 3.4(2) . . . . ?
C6 C11 C12 C13 -168.60(15) . . . . ?
C11 C12 C13 C14 -3.1(2) . . . . ?
C11 C12 C13 C1 170.08(14) . . . . ?
O1 C1 C13 C12 -139.55(16) . . . . ?
N1 C1 C13 C12 37.1(2) . . . . ?
O1 C1 C13 C14 33.8(2) . . . . ?
N1 C1 C13 C14 -149.59(14) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C1 C13 C14 C15 -173.38(16) . . . . ?
C13 C14 C15 C16 2.9(3) . . . . ?
C14 C15 C16 C11 -2.6(3) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C6 C11 C16 C15 171.69(17) . . . . ?
C2 N1 C11A N12A -126.42(15) . . . . ?
C1 N1 C11A N12A 31.71(19) . . . . ?
C2 N1 C11A C16A 54.2(2) . . . . ?
C1 N1 C11A C16A -147.66(15) . . . . ?
C16A C11A N12A C13A 0.4(2) . . . . ?
N1 C11A N12A C13A -178.91(14) . . . . ?
C11A N12A C13A C14A -1.2(3) . . . . ?
N12A C13A C14A F14A -179.23(18) . . . . ?
N12A C13A C14A C15A 0.3(3) . . . . ?
F14A C14A C15A C16A -179.20(19) . . . . ?
C13A C14A C15A C16A 1.3(3) . . . . ?
C14A C15A C16A C11A -1.9(3) . . . . ?
N12A C11A C16A C15A 1.1(3) . . . . ?
N1 C11A C16A C15A -179.57(16) . . . . ?
O2 C2 C21 C26 22.6(2) . . . . ?
N1 C2 C21 C26 -162.48(15) . . . . ?
O2 C2 C21 C22 -151.06(17) . . . . ?
N1 C2 C21 C22 23.9(2) . . . . ?
C26 C21 C22 C23 -2.1(2) . . . . ?
C2 C21 C22 C23 171.55(15) . . . . ?
C21 C22 C23 C24 1.1(2) . . . . ?
C21 C22 C23 C3 -174.11(15) . . . . ?
O3 C3 C23 C22 123.15(18) . . . . ?
N2 C3 C23 C22 -55.1(2) . . . . ?
O3 C3 C23 C24 -52.0(2) . . . . ?
N2 C3 C23 C24 129.67(16) . . . . ?
C22 C23 C24 C25 1.3(3) . . . . ?
C3 C23 C24 C25 176.48(16) . . . . ?
C23 C24 C25 C26 -2.7(3) . . . . ?
C24 C25 C26 C21 1.7(3) . . . . ?
C22 C21 C26 C25 0.7(3) . . . . ?
C2 C21 C26 C25 -173.19(16) . . . . ?
C3 N2 C21A N22A -37.3(2) . . . . ?
C4 N2 C21A N22A 117.54(16) . . . . ?
C3 N2 C21A C26A 143.40(17) . . . . ?
C4 N2 C21A C26A -61.8(2) . . . . ?
C26A C21A N22A C23A -1.7(3) . . . . ?
N2 C21A N22A C23A 179.08(16) . . . . ?
C21A N22A C23A C24A 2.3(3) . . . . ?
N22A C23A C24A C25A -1.3(4) . . . . ?
N22A C23A C24A F24A 178.4(2) . . . . ?
C23A C24A C25A C26A -0.6(4) . . . . ?
F24A C24A C25A C26A 179.8(2) . . . . ?
N22A C21A C26A C25A -0.1(3) . . . . ?
N2 C21A C26A C25A 179.12(19) . . . . ?
C24A C25A C26A C21A 1.2(3) . . . . ?
O4 C4 C31 C32 125.5(2) . . . . ?
N2 C4 C31 C32 -47.8(2) . . . . ?
O4 C4 C31 C36 -46.8(3) . . . . ?
N2 C4 C31 C36 139.91(17) . . . . ?
C36 C31 C32 C33 1.6(3) . . . . ?
C4 C31 C32 C33 -170.70(17) . . . . ?
C31 C32 C33 C34 -3.2(3) . . . . ?
C31 C32 C33 C5 -179.51(18) . . . . ?
O5 C5 C33 C34 -35.9(3) . . . . ?
N3 C5 C33 C34 147.61(18) . . . . ?
O5 C5 C33 C32 140.4(2) . . . . ?
N3 C5 C33 C32 -36.1(3) . . . . ?
C32 C33 C34 C35 1.6(3) . . . . ?
C5 C33 C34 C35 178.08(19) . . . . ?
C33 C34 C35 C36 1.6(3) . . . . ?
C34 C35 C36 C31 -3.2(3) . . . . ?
C32 C31 C36 C35 1.6(3) . . . . ?
C4 C31 C36 C35 173.87(18) . . . . ?
C5 N3 C31A N32A 137.37(18) . . . . ?
C6 N3 C31A N32A -23.9(2) . . . . ?
C5 N3 C31A C36A -43.3(2) . . . . ?
C6 N3 C31A C36A 155.40(17) . . . . ?
C36A C31A N32A C33A 0.1(3) . . . . ?
N3 C31A N32A C33A 179.37(19) . . . . ?
C31A N32A C33A C34A 2.1(4) . . . . ?
N32A C33A C34A C35A -2.0(4) . . . . ?
N32A C33A C34A F34A 177.7(2) . . . . ?
F34A C34A C35A C36A 180.0(2) . . . . ?
C33A C34A C35A C36A -0.3(4) . . . . ?
C34A C35A C36A C31A 2.3(3) . . . . ?
N32A C31A C36A C35A -2.3(3) . . . . ?
N3 C31A C36A C35A 178.42(17) . . . . ?


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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
C2S H2S3 F24A 0.96 2.52 3.368(4) 148 4_665 yes
C15 H15 F14A 0.93 2.54 3.235(2) 132 2_655 yes
C23A H23A O6 0.93 2.45 3.316(3) 155 1_455 yes
C34 H34 N12A 0.93 2.51 3.364(2) 152 4_665 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FIO4_CHCl3
_audit_block_doi                 10.5517/cc14n3yv
_database_code_depnum_ccdc_archive 'CCDC 1062027'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (FIO)4
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H28 F4 N8 O8, C H Cl3'
_chemical_formula_sum            'C53 H29 Cl3 F4 N8 O8'
_chemical_formula_weight         1088.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.0070(10)
_cell_length_b                   12.0935(9)
_cell_length_c                   17.6041(14)
_cell_angle_alpha                100.016(7)
_cell_angle_beta                 103.607(7)
_cell_angle_gamma                90.467(7)
_cell_volume                     2443.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3446
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      63.4

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1108
_exptl_absorpt_coefficient_mu    2.399
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.5743
_exptl_absorpt_correction_T_max  0.8895
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         13841
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_reflns_number            13850
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         63.23
_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        62.50
_diffrn_measured_fraction_theta_full 0.999
_reflns_number_total             7799
_reflns_number_gt                5375
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.0981P)²+0.2116P] where P=(Fo²+2Fc²)/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         7799
_refine_ls_number_parameters     721
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1839
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046

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
F14A F 1.0359(3) 0.3249(3) 0.11536(17) 0.1164(9) Uani 1 1 d . . .
C11 C 0.4729(3) -0.0380(2) 0.26123(18) 0.0600(7) Uani 1 1 d . . .
C12 C 0.5792(3) -0.0088(2) 0.25192(16) 0.0579(7) Uani 1 1 d . . .
H12 H 0.6139 0.0617 0.2760 0.069 Uiso 1 1 calc R . .
C13 C 0.6347(3) -0.0851(2) 0.20632(17) 0.0603(7) Uani 1 1 d . . .
C14 C 0.5848(3) -0.1910(3) 0.17351(19) 0.0697(9) Uani 1 1 d . . .
H14 H 0.6222 -0.2421 0.1436 0.084 Uiso 1 1 calc R . .
C15 C 0.4795(3) -0.2219(3) 0.1847(2) 0.0725(9) Uani 1 1 d . . .
H15 H 0.4472 -0.2940 0.1636 0.087 Uiso 1 1 calc R . .
C16 C 0.4231(3) -0.1450(3) 0.22728(19) 0.0686(8) Uani 1 1 d . . .
H16 H 0.3511 -0.1646 0.2334 0.082 Uiso 1 1 calc R . .
O1 O 0.7542(3) -0.0836(3) 0.11852(16) 0.0988(9) Uani 1 1 d . . .
C1 C 0.7393(3) -0.0508(3) 0.18367(19) 0.0673(8) Uani 1 1 d . . .
N1 N 0.8183(2) 0.0297(2) 0.23905(15) 0.0636(6) Uani 1 1 d . . .
O2 O 0.8320(3) -0.0666(2) 0.34029(15) 0.0845(7) Uani 1 1 d . . .
C2 C 0.8514(3) 0.0200(3) 0.31900(19) 0.0647(8) Uani 1 1 d . . .
C11A C 0.8809(3) 0.1047(3) 0.20689(18) 0.0636(8) Uani 1 1 d . . .
N12A N 0.8159(3) 0.1691(2) 0.16311(16) 0.0692(7) Uani 1 1 d . . .
C13A C 0.8708(4) 0.2404(3) 0.1319(2) 0.0764(10) Uani 1 1 d . . .
H13A H 0.8280 0.2855 0.0993 0.092 Uiso 1 1 calc R . .
C14A C 0.9865(4) 0.2485(3) 0.1465(2) 0.0801(10) Uani 1 1 d . . .
C15A C 1.0545(4) 0.1816(4) 0.1915(2) 0.0849(11) Uani 1 1 d . . .
H15A H 1.1340 0.1870 0.2009 0.102 Uiso 1 1 calc R . .
C16A C 0.9987(3) 0.1061(3) 0.2219(2) 0.0740(9) Uani 1 1 d . . .
H16A H 1.0398 0.0571 0.2519 0.089 Uiso 1 1 calc R . .
F24A F 0.4493(2) 0.7522(2) 0.37721(14) 0.0963(7) Uani 1 1 d . . .
C21 C 0.9075(3) 0.1219(3) 0.37641(18) 0.0611(7) Uani 1 1 d . . .
C22 C 0.8644(3) 0.2268(3) 0.37269(17) 0.0580(7) Uani 1 1 d . . .
H22 H 0.8076 0.2372 0.3288 0.070 Uiso 1 1 calc R . .
C23 C 0.9053(3) 0.3165(3) 0.43379(18) 0.0597(7) Uani 1 1 d . . .
C24 C 0.9944(3) 0.3012(3) 0.4972(2) 0.0710(9) Uani 1 1 d . . .
H24 H 1.0223 0.3610 0.5386 0.085 Uiso 1 1 calc R . .
C25 C 1.0416(3) 0.1974(3) 0.4989(2) 0.0768(9) Uani 1 1 d . . .
H25 H 1.1033 0.1884 0.5402 0.092 Uiso 1 1 calc R . .
C26 C 0.9979(3) 0.1086(3) 0.4399(2) 0.0710(9) Uani 1 1 d . . .
H26 H 1.0284 0.0384 0.4420 0.085 Uiso 1 1 calc R . .
O3 O 0.8311(3) 0.4706(2) 0.50329(13) 0.0814(7) Uani 1 1 d . . .
C3 C 0.8441(3) 0.4228(3) 0.44050(18) 0.0632(8) Uani 1 1 d . . .
N2 N 0.7901(2) 0.4601(2) 0.36936(14) 0.0592(6) Uani 1 1 d . . .
O4 O 0.9534(2) 0.4556(3) 0.32439(16) 0.0887(8) Uani 1 1 d . . .
C4 C 0.8518(3) 0.4653(3) 0.31041(19) 0.0635(8) Uani 1 1 d . . .
C21A C 0.6989(3) 0.5355(2) 0.37408(17) 0.0589(7) Uani 1 1 d . . .
N22A N 0.7173(3) 0.6364(2) 0.35921(15) 0.0641(7) Uani 1 1 d . . .
C23A C 0.6323(3) 0.7074(3) 0.36010(19) 0.0694(9) Uani 1 1 d . . .
H23A H 0.6417 0.7790 0.3493 0.083 Uiso 1 1 calc R . .
C24A C 0.5319(3) 0.6764(3) 0.37659(19) 0.0696(9) Uani 1 1 d . . .
C25A C 0.5153(3) 0.5738(3) 0.3942(2) 0.0740(9) Uani 1 1 d . . .
H25A H 0.4479 0.5543 0.4071 0.089 Uiso 1 1 calc R . .
C26A C 0.6010(3) 0.4994(3) 0.3925(2) 0.0661(8) Uani 1 1 d . . .
H26A H 0.5932 0.4275 0.4033 0.079 Uiso 1 1 calc R . .
F34A F 0.2246(4) -0.1004(3) 0.03230(19) 0.1608(16) Uani 1 1 d . . .
C31 C 0.7822(3) 0.4777(3) 0.23008(18) 0.0615(7) Uani 1 1 d . . .
C32 C 0.6794(3) 0.4175(2) 0.19535(17) 0.0578(7) Uani 1 1 d . . .
H32 H 0.6450 0.3780 0.2253 0.069 Uiso 1 1 calc R . .
C33 C 0.6273(3) 0.4158(3) 0.11603(18) 0.0615(7) Uani 1 1 d . . .
C34 C 0.6752(3) 0.4816(3) 0.0729(2) 0.0743(9) Uani 1 1 d . . .
H34 H 0.6396 0.4825 0.0201 0.089 Uiso 1 1 calc R . .
C35 C 0.7744(4) 0.5444(4) 0.1087(2) 0.0853(11) Uani 1 1 d . . .
H35 H 0.8052 0.5893 0.0800 0.102 Uiso 1 1 calc R . .
C36 C 0.8304(4) 0.5426(3) 0.1869(2) 0.0789(10) Uani 1 1 d . . .
H36 H 0.8992 0.5842 0.2101 0.095 Uiso 1 1 calc R . .
O5 O 0.5235(3) 0.2853(3) 0.00664(14) 0.1030(10) Uani 1 1 d . . .
C5 C 0.5302(3) 0.3350(3) 0.07279(18) 0.0670(8) Uani 1 1 d . . .
N3 N 0.4508(2) 0.3092(2) 0.11690(15) 0.0611(6) Uani 1 1 d . . .
O6 O 0.4090(2) 0.4927(2) 0.13986(17) 0.0845(7) Uani 1 1 d . . .
C6 C 0.4015(3) 0.4004(3) 0.15688(19) 0.0629(8) Uani 1 1 d . . .
C31A C 0.3929(3) 0.2006(3) 0.09304(18) 0.0658(8) Uani 1 1 d . . .
N32A N 0.2802(3) 0.1984(3) 0.07755(19) 0.0866(9) Uani 1 1 d . . .
C33A C 0.2246(5) 0.0958(4) 0.0573(2) 0.1025(15) Uani 1 1 d . . .
H33A H 0.1450 0.0901 0.0469 0.123 Uiso 1 1 calc R . .
C34A C 0.2852(6) 0.0003(4) 0.0522(2) 0.1022(16) Uani 1 1 d . . .
C35A C 0.3997(6) 0.0034(3) 0.0655(2) 0.0979(14) Uani 1 1 d . . .
H35A H 0.4392 -0.0623 0.0598 0.117 Uiso 1 1 calc R . .
C36A C 0.4568(4) 0.1072(3) 0.0881(2) 0.0776(10) Uani 1 1 d . . .
H36A H 0.5365 0.1140 0.0997 0.093 Uiso 1 1 calc R . .
F44A F 0.8435(2) 0.1275(2) 0.59382(15) 0.1063(8) Uani 1 1 d . . .
C41 C 0.3481(3) 0.3804(2) 0.22157(18) 0.0588(7) Uani 1 1 d . . .
C42 C 0.3847(3) 0.3007(2) 0.26777(17) 0.0566(7) Uani 1 1 d . . .
H42 H 0.4405 0.2522 0.2562 0.068 Uiso 1 1 calc R . .
C43 C 0.3375(3) 0.2932(2) 0.33216(18) 0.0591(7) Uani 1 1 d . . .
C44 C 0.2530(3) 0.3660(3) 0.3485(2) 0.0696(9) Uani 1 1 d . . .
H44 H 0.2214 0.3611 0.3913 0.084 Uiso 1 1 calc R . .
C45 C 0.2163(3) 0.4444(3) 0.3020(2) 0.0753(9) Uani 1 1 d . . .
H45 H 0.1592 0.4919 0.3128 0.090 Uiso 1 1 calc R . .
O7 O 0.3585(3) 0.2217(2) 0.45078(15) 0.0858(8) Uani 1 1 d . . .
C7 C 0.3789(3) 0.2149(3) 0.38667(19) 0.0637(8) Uani 1 1 d . . .
N4 N 0.4531(2) 0.1276(2) 0.36182(15) 0.0618(6) Uani 1 1 d . . .
C8 C 0.4006(3) 0.0447(3) 0.29875(19) 0.0620(8) Uani 1 1 d . . .
O8 O 0.2969(2) 0.0429(2) 0.27299(17) 0.0851(7) Uani 1 1 d . . .
C46 C 0.2641(3) 0.4531(3) 0.2390(2) 0.0705(9) Uani 1 1 d . . .
H46 H 0.2402 0.5076 0.2082 0.085 Uiso 1 1 calc R . .
C41A C 0.5573(3) 0.1195(2) 0.41985(17) 0.0590(7) Uani 1 1 d . . .
N42A N 0.6147(3) 0.2173(2) 0.45118(16) 0.0687(7) Uani 1 1 d . . .
C43A C 0.7090(3) 0.2184(3) 0.5098(2) 0.0734(9) Uani 1 1 d . . .
H43A H 0.7495 0.2862 0.5339 0.088 Uiso 1 1 calc R . .
C44A C 0.7466(3) 0.1215(3) 0.5349(2) 0.0746(9) Uani 1 1 d . . .
C45A C 0.6901(3) 0.0208(3) 0.5017(2) 0.0770(10) Uani 1 1 d . . .
H45A H 0.7177 -0.0452 0.5177 0.092 Uiso 1 1 calc R . .
C46A C 0.5901(3) 0.0196(3) 0.44354(19) 0.0650(8) Uani 1 1 d . . .
H46A H 0.5461 -0.0468 0.4210 0.078 Uiso 1 1 calc R . .
Cl1A Cl 0.1236(2) 0.7358(2) 0.23071(15) 0.1362(8) Uani 0.77 1 d P A 1
Cl2A Cl -0.0283(2) 0.7998(3) 0.0947(3) 0.1733(13) Uani 0.77 1 d P A 1
Cl3A Cl 0.1057(5) 0.6201(4) 0.0761(2) 0.242(2) Uani 0.77 1 d P A 1
C1A C 0.1070(7) 0.7592(8) 0.1329(5) 0.118(3) Uani 0.77 1 d P A 1
H1A H 0.1676 0.8099 0.1275 0.142 Uiso 0.77 1 calc PR A 1
Cl1B Cl 0.0345(19) 0.8440(13) 0.0907(11) 0.256(7) Uani 0.23 1 d PDU B 2
Cl2B Cl 0.0620(13) 0.7871(9) 0.2257(7) 0.178(4) Uani 0.23 1 d PDU B 2
Cl3B Cl 0.1742(7) 0.6687(6) 0.0943(6) 0.117(2) Uani 0.23 1 d PDU B 2
C1B C 0.060(3) 0.721(3) 0.1287(18) 0.187(12) Uani 0.23 1 d PDU B 2
H1B H -0.0070 0.6685 0.1078 0.225 Uiso 0.23 1 calc PR B 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
F14A C14A 1.352(4) . ?
C11 C12 1.376(5) . ?
C11 C16 1.392(4) . ?
C11 C8 1.498(4) . ?
C12 C13 1.394(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(4) . ?
C13 C1 1.480(5) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O1 C1 1.201(4) . ?
C1 N1 1.421(4) . ?
N1 C2 1.396(4) . ?
N1 C11A 1.440(4) . ?
O2 C2 1.211(4) . ?
C2 C21 1.492(5) . ?
C11A N12A 1.321(4) . ?
C11A C16A 1.376(5) . ?
N12A C13A 1.345(4) . ?
C13A C14A 1.351(6) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.369(6) . ?
C15A C16A 1.378(5) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
F24A C24A 1.356(4) . ?
C21 C22 1.380(4) . ?
C21 C26 1.396(5) . ?
C22 C23 1.383(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(5) . ?
C23 C3 1.487(4) . ?
C24 C25 1.384(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.362(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
O3 C3 1.200(4) . ?
C3 N2 1.418(4) . ?
N2 C4 1.418(4) . ?
N2 C21A 1.439(4) . ?
O4 C4 1.197(4) . ?
C4 C31 1.497(5) . ?
C21A N22A 1.320(4) . ?
C21A C26A 1.378(5) . ?
N22A C23A 1.340(4) . ?
C23A C24A 1.368(5) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.355(5) . ?
C25A C26A 1.375(5) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
F34A C34A 1.361(5) . ?
C31 C32 1.379(5) . ?
C31 C36 1.392(4) . ?
C32 C33 1.386(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.395(4) . ?
C33 C5 1.483(5) . ?
C34 C35 1.363(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
O5 C5 1.198(4) . ?
C5 N3 1.427(4) . ?
N3 C6 1.414(4) . ?
N3 C31A 1.428(4) . ?
O6 C6 1.213(4) . ?
C6 C41 1.484(4) . ?
C31A N32A 1.315(5) . ?
C31A C36A 1.372(5) . ?
N32A C33A 1.355(6) . ?
C33A C34A 1.371(7) . ?
C33A H33A 0.9300 . ?
C34A C35A 1.339(7) . ?
C35A C36A 1.375(6) . ?
C35A H35A 0.9300 . ?
C36A H36A 0.9300 . ?
F44A C44A 1.357(4) . ?
C41 C42 1.376(4) . ?
C41 C46 1.398(4) . ?
C42 C43 1.397(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.398(4) . ?
C43 C7 1.470(4) . ?
C44 C45 1.368(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.381(5) . ?
C45 H45 0.9300 . ?
O7 C7 1.200(4) . ?
C7 N4 1.462(4) . ?
N4 C8 1.382(4) . ?
N4 C41A 1.433(4) . ?
C8 O8 1.220(4) . ?
C46 H46 0.9300 . ?
C41A N42A 1.326(4) . ?
C41A C46A 1.377(4) . ?
N42A C43A 1.339(5) . ?
C43A C44A 1.366(5) . ?
C43A H43A 0.9300 . ?
C44A C45A 1.355(6) . ?
C45A C46A 1.381(5) . ?
C45A H45A 0.9300 . ?
C46A H46A 0.9300 . ?
Cl1A C1A 1.759(8) . ?
Cl2A C1A 1.716(8) . ?
Cl3A C1A 1.799(10) . ?
C1A H1A 0.9800 . ?
Cl1B C1B 1.73(3) . ?
Cl2B C1B 1.75(3) . ?
Cl3B C1B 1.71(3) . ?
C1B H1B 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
C12 C11 C16 119.7(3) . . ?
C12 C11 C8 122.7(3) . . ?
C16 C11 C8 117.1(3) . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 C1 118.4(3) . . ?
C12 C13 C1 121.4(3) . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O1 C1 N1 120.1(3) . . ?
O1 C1 C13 121.6(3) . . ?
N1 C1 C13 118.1(3) . . ?
C2 N1 C1 120.6(3) . . ?
C2 N1 C11A 121.0(3) . . ?
C1 N1 C11A 117.0(3) . . ?
O2 C2 N1 120.9(3) . . ?
O2 C2 C21 122.1(3) . . ?
N1 C2 C21 117.0(3) . . ?
N12A C11A C16A 124.6(3) . . ?
N12A C11A N1 114.4(3) . . ?
C16A C11A N1 121.0(3) . . ?
C11A N12A C13A 116.4(3) . . ?
N12A C13A C14A 121.9(4) . . ?
N12A C13A H13A 119.1 . . ?
C14A C13A H13A 119.1 . . ?
C13A C14A F14A 118.5(4) . . ?
C13A C14A C15A 122.1(4) . . ?
F14A C14A C15A 119.4(4) . . ?
C14A C15A C16A 116.4(4) . . ?
C14A C15A H15A 121.8 . . ?
C16A C15A H15A 121.8 . . ?
C11A C16A C15A 118.6(4) . . ?
C11A C16A H16A 120.7 . . ?
C15A C16A H16A 120.7 . . ?
C22 C21 C26 119.4(3) . . ?
C22 C21 C2 121.3(3) . . ?
C26 C21 C2 118.9(3) . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 119.3(3) . . ?
C22 C23 C3 121.4(3) . . ?
C24 C23 C3 118.5(3) . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.5(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
O3 C3 N2 120.2(3) . . ?
O3 C3 C23 121.4(3) . . ?
N2 C3 C23 118.0(3) . . ?
C3 N2 C4 119.8(3) . . ?
C3 N2 C21A 116.4(2) . . ?
C4 N2 C21A 118.2(2) . . ?
O4 C4 N2 120.9(3) . . ?
O4 C4 C31 122.7(3) . . ?
N2 C4 C31 116.4(3) . . ?
N22A C21A C26A 125.0(3) . . ?
N22A C21A N2 115.3(3) . . ?
C26A C21A N2 119.7(3) . . ?
C21A N22A C23A 116.9(3) . . ?
N22A C23A C24A 121.2(3) . . ?
N22A C23A H23A 119.4 . . ?
C24A C23A H23A 119.4 . . ?
C25A C24A F24A 120.0(3) . . ?
C25A C24A C23A 121.5(3) . . ?
F24A C24A C23A 118.5(3) . . ?
C24A C25A C26A 118.1(3) . . ?
C24A C25A H25A 121.0 . . ?
C26A C25A H25A 121.0 . . ?
C25A C26A C21A 117.3(3) . . ?
C25A C26A H26A 121.3 . . ?
C21A C26A H26A 121.3 . . ?
C32 C31 C36 120.0(3) . . ?
C32 C31 C4 121.9(3) . . ?
C36 C31 C4 117.8(3) . . ?
C31 C32 C33 120.3(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C34 119.6(3) . . ?
C32 C33 C5 121.5(3) . . ?
C34 C33 C5 118.5(3) . . ?
C35 C34 C33 119.7(3) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 121.3(3) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C31 119.1(4) . . ?
C35 C36 H36 120.5 . . ?
C31 C36 H36 120.5 . . ?
O5 C5 N3 120.7(3) . . ?
O5 C5 C33 122.3(3) . . ?
N3 C5 C33 116.6(3) . . ?
C6 N3 C5 117.4(3) . . ?
C6 N3 C31A 120.8(3) . . ?
C5 N3 C31A 116.9(3) . . ?
O6 C6 N3 119.2(3) . . ?
O6 C6 C41 122.4(3) . . ?
N3 C6 C41 118.3(3) . . ?
N32A C31A C36A 124.8(4) . . ?
N32A C31A N3 116.3(3) . . ?
C36A C31A N3 118.9(3) . . ?
C31A N32A C33A 116.8(4) . . ?
N32A C33A C34A 120.3(5) . . ?
N32A C33A H33A 119.8 . . ?
C34A C33A H33A 119.8 . . ?
C35A C34A F34A 119.9(5) . . ?
C35A C34A C33A 122.5(4) . . ?
F34A C34A C33A 117.6(6) . . ?
C34A C35A C36A 117.5(4) . . ?
C34A C35A H35A 121.3 . . ?
C36A C35A H35A 121.3 . . ?
C31A C36A C35A 118.1(4) . . ?
C31A C36A H36A 120.9 . . ?
C35A C36A H36A 120.9 . . ?
C42 C41 C46 120.0(3) . . ?
C42 C41 C6 122.7(3) . . ?
C46 C41 C6 117.0(3) . . ?
C41 C42 C43 119.7(3) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
C42 C43 C44 119.6(3) . . ?
C42 C43 C7 121.9(3) . . ?
C44 C43 C7 118.4(3) . . ?
C45 C44 C43 120.5(3) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C44 C45 C46 120.0(3) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
O7 C7 N4 119.0(3) . . ?
O7 C7 C43 123.6(3) . . ?
N4 C7 C43 117.3(3) . . ?
C8 N4 C41A 126.5(3) . . ?
C8 N4 C7 115.6(3) . . ?
C41A N4 C7 114.7(2) . . ?
O8 C8 N4 119.3(3) . . ?
O8 C8 C11 121.4(3) . . ?
N4 C8 C11 119.3(3) . . ?
C45 C46 C41 120.2(3) . . ?
C45 C46 H46 119.9 . . ?
C41 C46 H46 119.9 . . ?
N42A C41A C46A 123.8(3) . . ?
N42A C41A N4 113.9(3) . . ?
C46A C41A N4 122.3(3) . . ?
C41A N42A C43A 117.7(3) . . ?
N42A C43A C44A 121.1(3) . . ?
N42A C43A H43A 119.5 . . ?
C44A C43A H43A 119.5 . . ?
C45A C44A F44A 120.0(4) . . ?
C45A C44A C43A 121.5(4) . . ?
F44A C44A C43A 118.5(4) . . ?
C44A C45A C46A 117.8(3) . . ?
C44A C45A H45A 121.1 . . ?
C46A C45A H45A 121.1 . . ?
C41A C46A C45A 118.1(3) . . ?
C41A C46A H46A 121.0 . . ?
C45A C46A H46A 121.0 . . ?
Cl2A C1A Cl1A 111.7(5) . . ?
Cl2A C1A Cl3A 102.1(5) . . ?
Cl1A C1A Cl3A 103.5(4) . . ?
Cl2A C1A H1A 112.9 . . ?
Cl1A C1A H1A 112.9 . . ?
Cl3A C1A H1A 112.9 . . ?
Cl3B C1B Cl1B 104.1(17) . . ?
Cl3B C1B Cl2B 127(2) . . ?
Cl1B C1B Cl2B 93.6(15) . . ?
Cl3B C1B H1B 110.0 . . ?
Cl1B C1B H1B 110.0 . . ?
Cl2B C1B H1B 110.0 . . ?

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
C16 C11 C12 C13 2.2(5) . . . . ?
C8 C11 C12 C13 -170.6(3) . . . . ?
C11 C12 C13 C14 -2.6(5) . . . . ?
C11 C12 C13 C1 169.6(3) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C1 C13 C14 C15 -171.8(3) . . . . ?
C13 C14 C15 C16 1.7(5) . . . . ?
C14 C15 C16 C11 -2.1(5) . . . . ?
C12 C11 C16 C15 0.2(5) . . . . ?
C8 C11 C16 C15 173.4(3) . . . . ?
C14 C13 C1 O1 32.9(5) . . . . ?
C12 C13 C1 O1 -139.5(4) . . . . ?
C14 C13 C1 N1 -152.2(3) . . . . ?
C12 C13 C1 N1 35.5(4) . . . . ?
O1 C1 N1 C2 -139.3(4) . . . . ?
C13 C1 N1 C2 45.7(4) . . . . ?
O1 C1 N1 C11A 27.2(5) . . . . ?
C13 C1 N1 C11A -147.8(3) . . . . ?
C1 N1 C2 O2 14.4(5) . . . . ?
C11A N1 C2 O2 -151.5(3) . . . . ?
C1 N1 C2 C21 -163.6(3) . . . . ?
C11A N1 C2 C21 30.5(4) . . . . ?
C2 N1 C11A N12A -132.5(3) . . . . ?
C1 N1 C11A N12A 61.1(4) . . . . ?
C2 N1 C11A C16A 47.7(4) . . . . ?
C1 N1 C11A C16A -118.7(3) . . . . ?
C16A C11A N12A C13A -0.2(5) . . . . ?
N1 C11A N12A C13A -180.0(3) . . . . ?
C11A N12A C13A C14A -2.0(5) . . . . ?
N12A C13A C14A F14A -177.7(3) . . . . ?
N12A C13A C14A C15A 2.5(6) . . . . ?
C13A C14A C15A C16A -0.6(6) . . . . ?
F14A C14A C15A C16A 179.6(3) . . . . ?
N12A C11A C16A C15A 2.0(5) . . . . ?
N1 C11A C16A C15A -178.2(3) . . . . ?
C14A C15A C16A C11A -1.5(5) . . . . ?
O2 C2 C21 C22 -133.1(4) . . . . ?
N1 C2 C21 C22 44.9(4) . . . . ?
O2 C2 C21 C26 40.1(5) . . . . ?
N1 C2 C21 C26 -141.9(3) . . . . ?
C26 C21 C22 C23 -4.1(5) . . . . ?
C2 C21 C22 C23 169.1(3) . . . . ?
C21 C22 C23 C24 3.3(5) . . . . ?
C21 C22 C23 C3 -166.2(3) . . . . ?
C22 C23 C24 C25 0.1(5) . . . . ?
C3 C23 C24 C25 169.9(3) . . . . ?
C23 C24 C25 C26 -2.7(6) . . . . ?
C24 C25 C26 C21 1.8(6) . . . . ?
C22 C21 C26 C25 1.6(5) . . . . ?
C2 C21 C26 C25 -171.8(3) . . . . ?
C22 C23 C3 O3 136.9(4) . . . . ?
C24 C23 C3 O3 -32.6(5) . . . . ?
C22 C23 C3 N2 -36.2(4) . . . . ?
C24 C23 C3 N2 154.2(3) . . . . ?
O3 C3 N2 C4 137.6(3) . . . . ?
C23 C3 N2 C4 -49.2(4) . . . . ?
O3 C3 N2 C21A -15.6(5) . . . . ?
C23 C3 N2 C21A 157.6(3) . . . . ?
C3 N2 C4 O4 -11.7(5) . . . . ?
C21A N2 C4 O4 141.0(3) . . . . ?
C3 N2 C4 C31 165.4(3) . . . . ?
C21A N2 C4 C31 -41.8(4) . . . . ?
C3 N2 C21A N22A 117.4(3) . . . . ?
C4 N2 C21A N22A -36.3(4) . . . . ?
C3 N2 C21A C26A -63.1(4) . . . . ?
C4 N2 C21A C26A 143.2(3) . . . . ?
C26A C21A N22A C23A -1.9(5) . . . . ?
N2 C21A N22A C23A 177.5(3) . . . . ?
C21A N22A C23A C24A 0.7(5) . . . . ?
N22A C23A C24A C25A 1.3(5) . . . . ?
N22A C23A C24A F24A 179.5(3) . . . . ?
F24A C24A C25A C26A 179.7(3) . . . . ?
C23A C24A C25A C26A -2.2(5) . . . . ?
C24A C25A C26A C21A 1.0(5) . . . . ?
N22A C21A C26A C25A 1.1(5) . . . . ?
N2 C21A C26A C25A -178.4(3) . . . . ?
O4 C4 C31 C32 134.6(4) . . . . ?
N2 C4 C31 C32 -42.5(4) . . . . ?
O4 C4 C31 C36 -38.2(5) . . . . ?
N2 C4 C31 C36 144.7(3) . . . . ?
C36 C31 C32 C33 4.0(5) . . . . ?
C4 C31 C32 C33 -168.6(3) . . . . ?
C31 C32 C33 C34 -4.5(5) . . . . ?
C31 C32 C33 C5 167.7(3) . . . . ?
C32 C33 C34 C35 1.9(5) . . . . ?
C5 C33 C34 C35 -170.6(4) . . . . ?
C33 C34 C35 C36 1.3(6) . . . . ?
C34 C35 C36 C31 -1.8(6) . . . . ?
C32 C31 C36 C35 -0.9(6) . . . . ?
C4 C31 C36 C35 172.1(3) . . . . ?
C32 C33 C5 O5 -136.9(4) . . . . ?
C34 C33 C5 O5 35.3(5) . . . . ?
C32 C33 C5 N3 36.1(4) . . . . ?
C34 C33 C5 N3 -151.6(3) . . . . ?
O5 C5 N3 C6 -133.6(4) . . . . ?
C33 C5 N3 C6 53.2(4) . . . . ?
O5 C5 N3 C31A 21.9(5) . . . . ?
C33 C5 N3 C31A -151.3(3) . . . . ?
C5 N3 C6 O6 14.9(5) . . . . ?
C31A N3 C6 O6 -139.6(3) . . . . ?
C5 N3 C6 C41 -161.7(3) . . . . ?
C31A N3 C6 C41 43.8(4) . . . . ?
C6 N3 C31A N32A 28.6(4) . . . . ?
C5 N3 C31A N32A -126.0(3) . . . . ?
C6 N3 C31A C36A -151.1(3) . . . . ?
C5 N3 C31A C36A 54.3(4) . . . . ?
C36A C31A N32A C33A 1.8(5) . . . . ?
N3 C31A N32A C33A -178.0(3) . . . . ?
C31A N32A C33A C34A -1.3(6) . . . . ?
N32A C33A C34A C35A -0.9(7) . . . . ?
N32A C33A C34A F34A 179.4(4) . . . . ?
F34A C34A C35A C36A -177.8(3) . . . . ?
C33A C34A C35A C36A 2.5(6) . . . . ?
N32A C31A C36A C35A -0.1(5) . . . . ?
N3 C31A C36A C35A 179.6(3) . . . . ?
C34A C35A C36A C31A -2.0(6) . . . . ?
O6 C6 C41 C42 -146.9(3) . . . . ?
N3 C6 C41 C42 29.5(5) . . . . ?
O6 C6 C41 C46 27.6(5) . . . . ?
N3 C6 C41 C46 -155.9(3) . . . . ?
C46 C41 C42 C43 -0.1(5) . . . . ?
C6 C41 C42 C43 174.3(3) . . . . ?
C41 C42 C43 C44 0.6(5) . . . . ?
C41 C42 C43 C7 -175.7(3) . . . . ?
C42 C43 C44 C45 0.0(5) . . . . ?
C7 C43 C44 C45 176.4(3) . . . . ?
C43 C44 C45 C46 -0.9(6) . . . . ?
C42 C43 C7 O7 163.9(3) . . . . ?
C44 C43 C7 O7 -12.4(5) . . . . ?
C42 C43 C7 N4 -13.3(5) . . . . ?
C44 C43 C7 N4 170.3(3) . . . . ?
O7 C7 N4 C8 113.4(4) . . . . ?
C43 C7 N4 C8 -69.2(4) . . . . ?
O7 C7 N4 C41A -47.9(4) . . . . ?
C43 C7 N4 C41A 129.5(3) . . . . ?
C41A N4 C8 O8 152.1(3) . . . . ?
C7 N4 C8 O8 -6.6(4) . . . . ?
C41A N4 C8 C11 -30.6(4) . . . . ?
C7 N4 C8 C11 170.7(3) . . . . ?
C12 C11 C8 O8 140.6(3) . . . . ?
C16 C11 C8 O8 -32.3(5) . . . . ?
C12 C11 C8 N4 -36.7(4) . . . . ?
C16 C11 C8 N4 150.4(3) . . . . ?
C44 C45 C46 C41 1.4(6) . . . . ?
C42 C41 C46 C45 -0.9(5) . . . . ?
C6 C41 C46 C45 -175.6(3) . . . . ?
C8 N4 C41A N42A 152.4(3) . . . . ?
C7 N4 C41A N42A -48.7(4) . . . . ?
C8 N4 C41A C46A -31.2(4) . . . . ?
C7 N4 C41A C46A 127.6(3) . . . . ?
C46A C41A N42A C43A -0.8(5) . . . . ?
N4 C41A N42A C43A 175.5(3) . . . . ?
C41A N42A C43A C44A 1.9(5) . . . . ?
N42A C43A C44A C45A -0.2(5) . . . . ?
N42A C43A C44A F44A 179.2(3) . . . . ?
F44A C44A C45A C46A 178.2(3) . . . . ?
C43A C44A C45A C46A -2.4(5) . . . . ?
N42A C41A C46A C45A -1.9(5) . . . . ?
N4 C41A C46A C45A -177.9(3) . . . . ?
C44A C45A C46A C41A 3.4(5) . . . . ?


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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
C1A H1A F34A 0.98 2.37 3.193(8) 141 1_565 yes
C15 H15 O6 0.93 2.56 3.456(4) 162 1_545 yes
C42 H42 N4 0.93 2.57 2.897(4) 101 . yes
C45 H45 O4 0.93 2.57 3.273(4) 133 1_455 yes
C45A H45A O7 0.93 2.51 3.270(5) 139 2_656 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FIO4_Acetone
_audit_block_doi                 10.5517/cc14n3zw
_database_code_depnum_ccdc_archive 'CCDC 1062028'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (FIO)4:2(Acetone)
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H28 F4 N8 O18, 2(C2 H6 O)'
_chemical_formula_sum            'C58 H40 F4 N8 O10'
_chemical_formula_weight         1084.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   12.8052(1)
_cell_length_b                   23.0739(1)
_cell_length_c                   18.4579(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.394(1)
_cell_angle_gamma                90.00
_cell_volume                     5204.29(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    15569
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      63.04

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.7386
_exptl_absorpt_correction_T_max  0.8342
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         31733
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_reflns_number            31733
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         63.27
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        62.50
_diffrn_measured_fraction_theta_full 0.997
_reflns_number_total             8393
_reflns_number_gt                7604
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.092P)²+3.2921P] where P=(Fo²+2Fc²)/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       0.00062(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8393
_refine_ls_number_parameters     764
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1931
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.047
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
C11 C 0.2062(2) 0.22382(13) 0.42739(16) 0.0566(7) Uani 1 1 d . . .
C12 C 0.1540(2) 0.19238(11) 0.47013(15) 0.0517(6) Uani 1 1 d . . .
H12 H 0.0788 0.1959 0.4608 0.062 Uiso 1 1 calc R . .
C13 C 0.2136(2) 0.15552(12) 0.52697(16) 0.0558(6) Uani 1 1 d . . .
C14 C 0.3257(2) 0.14994(15) 0.5402(2) 0.0694(8) Uani 1 1 d . . .
H14 H 0.3662 0.1258 0.5787 0.083 Uiso 1 1 calc R . .
C15 C 0.3769(3) 0.18025(18) 0.4962(2) 0.0816(10) Uani 1 1 d . . .
H15 H 0.4516 0.1754 0.5041 0.098 Uiso 1 1 calc R . .
C16 C 0.3188(2) 0.21745(16) 0.44070(19) 0.0717(9) Uani 1 1 d . . .
H16 H 0.3544 0.2384 0.4120 0.086 Uiso 1 1 calc R . .
O1 O 0.21556(19) 0.10716(13) 0.64026(14) 0.0929(8) Uani 1 1 d . . .
C1 C 0.1637(2) 0.12485(13) 0.57909(17) 0.0605(7) Uani 1 1 d . . .
N1 N 0.04661(17) 0.11988(10) 0.55584(13) 0.0548(5) Uani 1 1 d . . .
O2 O 0.05105(17) 0.06316(9) 0.45739(13) 0.0699(6) Uani 1 1 d . . .
C2 C -0.0038(2) 0.08931(12) 0.49022(16) 0.0543(6) Uani 1 1 d . . .
C11A C -0.0024(2) 0.12852(14) 0.61605(16) 0.0614(7) Uani 1 1 d . . .
N12A N 0.0095(2) 0.18169(13) 0.64478(15) 0.0761(8) Uani 1 1 d . . .
C13A C -0.0313(4) 0.1912(2) 0.7023(2) 0.0960(13) Uani 1 1 d . . .
H13A H -0.0235 0.2278 0.7245 0.115 Uiso 1 1 calc R . .
C14A C -0.0840(4) 0.1493(3) 0.7295(2) 0.1058(16) Uani 1 1 d . . .
F14A F -0.1241(3) 0.1626(2) 0.78667(16) 0.1639(15) Uani 1 1 d . . .
C15A C -0.0943(4) 0.0956(3) 0.7004(3) 0.1108(16) Uani 1 1 d . . .
H15A H -0.1301 0.0668 0.7192 0.133 Uiso 1 1 calc R . .
C16A C -0.0505(3) 0.08388(19) 0.6418(2) 0.0849(10) Uani 1 1 d . . .
H16A H -0.0539 0.0470 0.6210 0.102 Uiso 1 1 calc R . .
C21 C -0.1251(2) 0.08995(11) 0.46022(15) 0.0527(6) Uani 1 1 d . . .
C22 C -0.1870(2) 0.13913(11) 0.46226(14) 0.0504(6) Uani 1 1 d . . .
H22 H -0.1536 0.1718 0.4888 0.060 Uiso 1 1 calc R . .
C23 C -0.2986(2) 0.13948(12) 0.42471(15) 0.0533(6) Uani 1 1 d . . .
C24 C -0.3482(2) 0.08987(13) 0.38819(17) 0.0637(7) Uani 1 1 d . . .
H24 H -0.4231 0.0898 0.3638 0.076 Uiso 1 1 calc R . .
C25 C -0.2877(3) 0.04060(13) 0.38766(19) 0.0725(9) Uani 1 1 d . . .
H25 H -0.3220 0.0072 0.3639 0.087 Uiso 1 1 calc R . .
C26 C -0.1768(3) 0.04080(12) 0.42225(18) 0.0660(8) Uani 1 1 d . . .
H26 H -0.1358 0.0079 0.4203 0.079 Uiso 1 1 calc R . .
O3 O -0.4479(2) 0.19985(11) 0.36496(15) 0.0958(9) Uani 1 1 d . . .
C3 C -0.3649(2) 0.19284(13) 0.41585(16) 0.0598(7) Uani 1 1 d . . .
N2 N -0.32399(18) 0.23946(10) 0.46815(13) 0.0553(5) Uani 1 1 d . . .
O4 O -0.3391(2) 0.18324(11) 0.56453(13) 0.0806(7) Uani 1 1 d . . .
C4 C -0.3084(2) 0.22836(14) 0.54483(16) 0.0601(7) Uani 1 1 d . . .
C21A C -0.3402(2) 0.29594(13) 0.43630(17) 0.0607(7) Uani 1 1 d . . .
N22A N -0.2895(2) 0.30535(14) 0.38403(17) 0.0797(8) Uani 1 1 d . . .
C23A C -0.3034(4) 0.3570(2) 0.3513(3) 0.1118(17) Uani 1 1 d . . .
H23A H -0.2709 0.3647 0.3135 0.134 Uiso 1 1 calc R . .
C24A C -0.3638(6) 0.3991(2) 0.3714(4) 0.131(3) Uani 1 1 d . . .
F24A F -0.3726(4) 0.45147(14) 0.3386(3) 0.219(3) Uani 1 1 d . . .
C25A C -0.4155(6) 0.3897(2) 0.4239(4) 0.139(2) Uani 1 1 d . . .
H25A H -0.4572 0.4186 0.4369 0.166 Uiso 1 1 calc R . .
C26A C -0.4048(3) 0.33533(18) 0.4583(2) 0.0920(12) Uani 1 1 d . . .
H26A H -0.4397 0.3263 0.4944 0.110 Uiso 1 1 calc R . .
C31 C -0.2505(2) 0.27323(14) 0.60059(15) 0.0584(7) Uani 1 1 d . . .
C32 C -0.1611(2) 0.30320(13) 0.59216(15) 0.0547(7) Uani 1 1 d . . .
H32 H -0.1413 0.2991 0.5479 0.066 Uiso 1 1 calc R . .
C33 C -0.1013(2) 0.33924(14) 0.64962(15) 0.0583(7) Uani 1 1 d . . .
C34 C -0.1338(3) 0.34718(17) 0.71458(17) 0.0739(9) Uani 1 1 d . . .
H34 H -0.0941 0.3716 0.7531 0.089 Uiso 1 1 calc R . .
C35 C -0.2251(3) 0.3186(2) 0.72146(18) 0.0838(11) Uani 1 1 d . . .
H35 H -0.2480 0.3247 0.7641 0.101 Uiso 1 1 calc R . .
C36 C -0.2825(3) 0.28109(18) 0.66580(18) 0.0748(9) Uani 1 1 d . . .
H36 H -0.3425 0.2610 0.6717 0.090 Uiso 1 1 calc R . .
O5 O 0.07434(19) 0.37836(15) 0.70432(13) 0.1004(10) Uani 1 1 d . . .
C5 C 0.0029(2) 0.36555(15) 0.64780(16) 0.0640(8) Uani 1 1 d . . .
N3 N 0.02178(18) 0.37115(10) 0.57551(13) 0.0563(6) Uani 1 1 d . . .
O6 O -0.1227(2) 0.43263(11) 0.53964(15) 0.0849(7) Uani 1 1 d . . .
C6 C -0.0529(2) 0.40602(12) 0.52171(18) 0.0617(7) Uani 1 1 d . . .
C31A C 0.1327(2) 0.36305(12) 0.57558(15) 0.0527(6) Uani 1 1 d . . .
N32A N 0.1827(2) 0.40850(12) 0.55834(16) 0.0714(7) Uani 1 1 d . . .
C33A C 0.2878(3) 0.40065(19) 0.5597(2) 0.0861(11) Uani 1 1 d . . .
H33A H 0.3257 0.4314 0.5469 0.103 Uiso 1 1 calc R . .
C34A C 0.3393(3) 0.3493(2) 0.5793(2) 0.0778(10) Uani 1 1 d . . .
F34A F 0.44485(17) 0.34486(15) 0.58054(16) 0.1246(10) Uani 1 1 d . . .
C35A C 0.2882(3) 0.30313(16) 0.59825(18) 0.0711(9) Uani 1 1 d . . .
H35A H 0.3245 0.2681 0.6123 0.085 Uiso 1 1 calc R . .
C36A C 0.1805(2) 0.30984(13) 0.59595(16) 0.0600(7) Uani 1 1 d . . .
H36A H 0.1412 0.2793 0.6078 0.072 Uiso 1 1 calc R . .
C41 C -0.0463(2) 0.40748(12) 0.44302(17) 0.0572(7) Uani 1 1 d . . .
C42 C -0.0199(2) 0.35902(12) 0.40757(16) 0.0555(7) Uani 1 1 d . . .
H42 H 0.0042 0.3254 0.4353 0.067 Uiso 1 1 calc R . .
C43 C -0.0295(3) 0.36082(12) 0.33038(16) 0.0604(7) Uani 1 1 d . . .
C44 C -0.0629(3) 0.41176(14) 0.29025(19) 0.0781(10) Uani 1 1 d . . .
H44 H -0.0696 0.4132 0.2387 0.094 Uiso 1 1 calc R . .
C45 C -0.0862(3) 0.46027(14) 0.3261(2) 0.0828(10) Uani 1 1 d . . .
H45 H -0.1059 0.4947 0.2992 0.099 Uiso 1 1 calc R . .
C46 C -0.0803(3) 0.45785(13) 0.4016(2) 0.0737(9) Uani 1 1 d . . .
H46 H -0.0992 0.4902 0.4250 0.088 Uiso 1 1 calc R . .
O7 O -0.0612(3) 0.30277(12) 0.22116(14) 0.1228(13) Uani 1 1 d . . .
C7 C -0.0186(3) 0.30816(14) 0.28809(16) 0.0705(8) Uani 1 1 d . . .
N4 N 0.0390(2) 0.26001(10) 0.33105(13) 0.0574(6) Uani 1 1 d . . .
O8 O 0.1942(2) 0.31329(11) 0.36405(17) 0.0904(8) Uani 1 1 d . . .
C8 C 0.1497(3) 0.26884(13) 0.37209(17) 0.0617(7) Uani 1 1 d . . .
C41A C -0.0060(2) 0.20392(12) 0.30782(14) 0.0530(6) Uani 1 1 d . . .
N42A N 0.0603(2) 0.16590(12) 0.29138(15) 0.0688(7) Uani 1 1 d . . .
C43A C 0.0201(4) 0.11274(16) 0.2719(2) 0.0844(10) Uani 1 1 d . . .
H43A H 0.0653 0.0845 0.2614 0.101 Uiso 1 1 calc R . .
C44A C -0.0855(4) 0.09885(15) 0.2668(2) 0.0821(10) Uani 1 1 d . . .
F44A F -0.1205(3) 0.04457(11) 0.24724(17) 0.1400(12) Uani 1 1 d . . .
C45A C -0.1544(3) 0.13863(16) 0.28166(18) 0.0753(9) Uani 1 1 d . . .
H45A H -0.2268 0.1295 0.2770 0.090 Uiso 1 1 calc R . .
C46A C -0.1132(2) 0.19288(14) 0.30386(16) 0.0613(7) Uani 1 1 d . . .
H46A H -0.1566 0.2214 0.3159 0.074 Uiso 1 1 calc R . .
O1A O 0.1828(7) 0.0105(3) 0.2190(4) 0.127(3) Uani 0.50 1 d PD A -1
C1A C 0.2021(6) 0.0042(3) 0.1597(4) 0.0770(19) Uani 0.50 1 d PD A -1
C2A C 0.1535(10) 0.0438(5) 0.0957(6) 0.107(3) Uani 0.50 1 d PD A -1
H2A1 H 0.1988 0.0446 0.0625 0.160 Uiso 0.50 1 calc PR A -1
H2A2 H 0.1486 0.0820 0.1148 0.160 Uiso 0.50 1 calc PR A -1
H2A3 H 0.0817 0.0304 0.0680 0.160 Uiso 0.50 1 calc PR A -1
C3A C 0.2894(19) -0.0363(11) 0.1533(12) 0.152(8) Uani 0.50 1 d PD A -1
H3A1 H 0.2685 -0.0535 0.1037 0.227 Uiso 0.50 1 calc PR A -1
H3A2 H 0.2995 -0.0661 0.1910 0.227 Uiso 0.50 1 calc PR A -1
H3A3 H 0.3566 -0.0153 0.1611 0.227 Uiso 0.50 1 calc PR A -1
O2A O 0.0940(7) -0.0153(4) 0.0435(6) 0.165(3) Uani 0.50 1 d PD B -2
C4A C 0.1679(7) -0.0027(4) 0.0983(5) 0.102(3) Uani 0.50 1 d PD B -2
C5A C 0.1690(17) 0.0515(7) 0.1407(11) 0.197(10) Uani 0.50 1 d PD B -2
H5A1 H 0.1996 0.0442 0.1941 0.295 Uiso 0.50 1 calc PR B -2
H5A2 H 0.0956 0.0657 0.1307 0.295 Uiso 0.50 1 calc PR B -2
H5A3 H 0.2126 0.0799 0.1251 0.295 Uiso 0.50 1 calc PR B -2
C6A C 0.2637(17) -0.0418(10) 0.1293(11) 0.138(8) Uani 0.50 1 d PD B -2
H6A1 H 0.2992 -0.0488 0.0911 0.206 Uiso 0.50 1 calc PR B -2
H6A2 H 0.2392 -0.0780 0.1442 0.206 Uiso 0.50 1 calc PR B -2
H6A3 H 0.3144 -0.0239 0.1727 0.206 Uiso 0.50 1 calc PR B -2
O1B O 0.4259(9) 0.0208(5) 0.3369(5) 0.366(7) Uani 1 1 d D . .
C1B C 0.3745(6) 0.0014(3) 0.3770(4) 0.171(3) Uani 1 1 d D . .
C2B C 0.3962(9) -0.0584(4) 0.3997(8) 0.289(7) Uani 1 1 d D . .
H2B1 H 0.4139 -0.0796 0.3602 0.434 Uiso 1 1 calc R . .
H2B2 H 0.3326 -0.0751 0.4088 0.434 Uiso 1 1 calc R . .
H2B3 H 0.4567 -0.0603 0.4454 0.434 Uiso 1 1 calc R . .
C3B C 0.2956(11) 0.0329(5) 0.4053(9) 0.347(10) Uani 1 1 d D . .
H3B1 H 0.2264 0.0345 0.3663 0.521 Uiso 1 1 calc R . .
H3B2 H 0.3217 0.0715 0.4192 0.521 Uiso 1 1 calc R . .
H3B3 H 0.2868 0.0132 0.4489 0.521 Uiso 1 1 calc R . .


_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
C11 C12 1.382(4) . ?
C11 C16 1.397(4) . ?
C11 C8 1.484(4) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(4) . ?
C13 C1 1.484(4) . ?
C14 C15 1.377(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O1 C1 1.198(4) . ?
C1 N1 1.435(4) . ?
N1 C2 1.383(4) . ?
N1 C11A 1.444(4) . ?
O2 C2 1.216(3) . ?
C2 C21 1.485(4) . ?
C11A N12A 1.327(4) . ?
C11A C16A 1.357(5) . ?
N12A C13A 1.334(5) . ?
C13A C14A 1.358(7) . ?
C13A H13A 0.9300 . ?
C14A F14A 1.341(5) . ?
C14A C15A 1.342(7) . ?
C15A C16A 1.386(6) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21 C22 1.391(4) . ?
C21 C26 1.392(4) . ?
C22 C23 1.390(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(4) . ?
C23 C3 1.477(4) . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
O3 C3 1.200(3) . ?
C3 N2 1.436(4) . ?
N2 C4 1.393(4) . ?
N2 C21A 1.419(4) . ?
O4 C4 1.207(4) . ?
C4 C31 1.491(4) . ?
C21A N22A 1.332(4) . ?
C21A C26A 1.370(5) . ?
N22A C23A 1.324(5) . ?
C23A C24A 1.361(9) . ?
C23A H23A 0.9300 . ?
C24A F24A 1.341(5) . ?
C24A C25A 1.345(9) . ?
C25A C26A 1.394(8) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
C31 C32 1.386(4) . ?
C31 C36 1.394(4) . ?
C32 C33 1.385(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.394(4) . ?
C33 C5 1.475(4) . ?
C34 C35 1.382(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.376(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
O5 C5 1.201(4) . ?
C5 N3 1.431(4) . ?
N3 C6 1.407(4) . ?
N3 C31A 1.433(3) . ?
O6 C6 1.210(4) . ?
C6 C41 1.480(4) . ?
C31A N32A 1.316(4) . ?
C31A C36A 1.373(4) . ?
N32A C33A 1.350(5) . ?
C33A C34A 1.352(6) . ?
C33A H33A 0.9300 . ?
C34A F34A 1.348(4) . ?
C34A C35A 1.350(5) . ?
C35A C36A 1.377(4) . ?
C35A H35A 0.9300 . ?
C36A H36A 0.9300 . ?
C41 C42 1.387(4) . ?
C41 C46 1.388(4) . ?
C42 C43 1.394(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.387(4) . ?
C43 C7 1.473(4) . ?
C44 C45 1.378(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.373(5) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
O7 C7 1.198(4) . ?
C7 N4 1.435(4) . ?
N4 C8 1.408(4) . ?
N4 C41A 1.430(4) . ?
O8 C8 1.204(4) . ?
C41A N42A 1.318(4) . ?
C41A C46A 1.376(4) . ?
N42A C43A 1.337(5) . ?
C43A C44A 1.365(6) . ?
C43A H43A 0.9300 . ?
C44A F44A 1.343(4) . ?
C44A C45A 1.357(5) . ?
C45A C46A 1.372(5) . ?
C45A H45A 0.9300 . ?
C46A H46A 0.9300 . ?
O1A C1A 1.200(7) . ?
C1A C2A 1.477(8) . ?
C1A C3A 1.488(8) . ?
C2A H2A1 0.9600 . ?
C2A H2A2 0.9600 . ?
C2A H2A3 0.9600 . ?
C3A H3A1 0.9600 . ?
C3A H3A2 0.9600 . ?
C3A H3A3 0.9600 . ?
O2A C4A 1.195(7) . ?
C4A C5A 1.474(8) . ?
C4A C6A 1.493(9) . ?
C5A H5A1 0.9600 . ?
C5A H5A2 0.9600 . ?
C5A H5A3 0.9600 . ?
C6A H6A1 0.9600 . ?
C6A H6A2 0.9600 . ?
C6A H6A3 0.9600 . ?
O1B C1B 1.214(7) . ?
C1B C2B 1.446(7) . ?
C1B C3B 1.462(8) . ?
C2B H2B1 0.9600 . ?
C2B H2B2 0.9600 . ?
C2B H2B3 0.9600 . ?
C3B H3B1 0.9600 . ?
C3B H3B2 0.9600 . ?
C3B H3B3 0.9600 . ?

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
C12 C11 C16 119.6(3) . . ?
C12 C11 C8 122.7(2) . . ?
C16 C11 C8 117.4(3) . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 C1 122.4(2) . . ?
C14 C13 C1 117.7(3) . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
O1 C1 N1 119.4(3) . . ?
O1 C1 C13 123.3(3) . . ?
N1 C1 C13 117.3(2) . . ?
C2 N1 C1 118.3(2) . . ?
C2 N1 C11A 123.2(2) . . ?
C1 N1 C11A 114.5(2) . . ?
O2 C2 N1 120.1(3) . . ?
O2 C2 C21 121.0(3) . . ?
N1 C2 C21 118.9(2) . . ?
N12A C11A C16A 124.9(3) . . ?
N12A C11A N1 114.3(3) . . ?
C16A C11A N1 120.8(3) . . ?
C11A N12A C13A 116.4(4) . . ?
N12A C13A C14A 122.2(5) . . ?
N12A C13A H13A 118.9 . . ?
C14A C13A H13A 118.9 . . ?
F14A C14A C15A 120.7(6) . . ?
F14A C14A C13A 118.5(6) . . ?
C15A C14A C13A 120.7(4) . . ?
C14A C15A C16A 118.5(4) . . ?
C14A C15A H15A 120.8 . . ?
C16A C15A H15A 120.8 . . ?
C11A C16A C15A 117.3(4) . . ?
C11A C16A H16A 121.4 . . ?
C15A C16A H16A 121.4 . . ?
C22 C21 C26 119.3(2) . . ?
C22 C21 C2 122.6(2) . . ?
C26 C21 C2 117.8(3) . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 C3 118.1(2) . . ?
C22 C23 C3 122.1(2) . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.5(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
O3 C3 N2 119.0(3) . . ?
O3 C3 C23 123.0(3) . . ?
N2 C3 C23 117.9(2) . . ?
C4 N2 C21A 123.3(2) . . ?
C4 N2 C3 117.3(2) . . ?
C21A N2 C3 115.5(2) . . ?
O4 C4 N2 120.3(3) . . ?
O4 C4 C31 122.0(3) . . ?
N2 C4 C31 117.7(3) . . ?
N22A C21A C26A 125.1(3) . . ?
N22A C21A N2 114.1(3) . . ?
C26A C21A N2 120.8(3) . . ?
C23A N22A C21A 116.7(4) . . ?
N22A C23A C24A 121.9(5) . . ?
N22A C23A H23A 119.1 . . ?
C24A C23A H23A 119.1 . . ?
F24A C24A C25A 118.6(8) . . ?
F24A C24A C23A 119.8(8) . . ?
C25A C24A C23A 121.6(5) . . ?
C24A C25A C26A 118.1(5) . . ?
C24A C25A H25A 120.9 . . ?
C26A C25A H25A 120.9 . . ?
C21A C26A C25A 116.6(5) . . ?
C21A C26A H26A 121.7 . . ?
C25A C26A H26A 121.7 . . ?
C32 C31 C36 119.8(3) . . ?
C32 C31 C4 121.7(2) . . ?
C36 C31 C4 118.2(3) . . ?
C33 C32 C31 120.0(2) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 119.9(3) . . ?
C32 C33 C5 121.8(2) . . ?
C34 C33 C5 118.0(3) . . ?
C35 C34 C33 119.7(3) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C36 C35 C34 120.6(3) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C31 119.8(3) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
O5 C5 N3 119.4(3) . . ?
O5 C5 C33 122.7(3) . . ?
N3 C5 C33 117.7(2) . . ?
C6 N3 C5 116.2(2) . . ?
C6 N3 C31A 122.7(2) . . ?
C5 N3 C31A 115.6(2) . . ?
O6 C6 N3 119.9(3) . . ?
O6 C6 C41 121.4(3) . . ?
N3 C6 C41 118.7(2) . . ?
N32A C31A C36A 124.7(3) . . ?
N32A C31A N3 116.7(3) . . ?
C36A C31A N3 118.5(3) . . ?
C31A N32A C33A 116.3(3) . . ?
N32A C33A C34A 121.8(3) . . ?
N32A C33A H33A 119.1 . . ?
C34A C33A H33A 119.1 . . ?
F34A C34A C35A 119.8(4) . . ?
F34A C34A C33A 118.6(4) . . ?
C35A C34A C33A 121.6(3) . . ?
C34A C35A C36A 117.6(3) . . ?
C34A C35A H35A 121.2 . . ?
C36A C35A H35A 121.2 . . ?
C31A C36A C35A 118.0(3) . . ?
C31A C36A H36A 121.0 . . ?
C35A C36A H36A 121.0 . . ?
C42 C41 C46 119.7(3) . . ?
C42 C41 C6 122.5(3) . . ?
C46 C41 C6 117.4(3) . . ?
C41 C42 C43 119.9(3) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C44 C43 C42 119.4(3) . . ?
C44 C43 C7 118.6(3) . . ?
C42 C43 C7 121.6(2) . . ?
C45 C44 C43 120.5(3) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C46 C45 C44 120.0(3) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C41 120.4(3) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
O7 C7 N4 119.3(3) . . ?
O7 C7 C43 123.1(3) . . ?
N4 C7 C43 117.4(2) . . ?
C8 N4 C41A 122.9(2) . . ?
C8 N4 C7 117.0(2) . . ?
C41A N4 C7 116.2(2) . . ?
O8 C8 N4 119.7(3) . . ?
O8 C8 C11 121.9(3) . . ?
N4 C8 C11 118.3(2) . . ?
N42A C41A C46A 124.5(3) . . ?
N42A C41A N4 116.2(3) . . ?
C46A C41A N4 119.3(3) . . ?
C41A N42A C43A 116.7(3) . . ?
N42A C43A C44A 121.8(3) . . ?
N42A C43A H43A 119.1 . . ?
C44A C43A H43A 119.1 . . ?
F44A C44A C45A 120.0(4) . . ?
F44A C44A C43A 118.8(4) . . ?
C45A C44A C43A 121.2(3) . . ?
C44A C45A C46A 117.6(3) . . ?
C44A C45A H45A 121.2 . . ?
C46A C45A H45A 121.2 . . ?
C45A C46A C41A 118.2(3) . . ?
C45A C46A H46A 120.9 . . ?
C41A C46A H46A 120.9 . . ?
O1A C1A C2A 120.1(7) . . ?
O1A C1A C3A 120.9(9) . . ?
C2A C1A C3A 118.1(9) . . ?
O2A C4A C5A 122.3(10) . . ?
O2A C4A C6A 122.0(10) . . ?
C5A C4A C6A 115.6(9) . . ?
C4A C5A H5A1 109.5 . . ?
C4A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C4A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
C4A C6A H6A1 109.5 . . ?
C4A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C4A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
O1B C1B C2B 116.0(9) . . ?
O1B C1B C3B 126.4(9) . . ?
C2B C1B C3B 117.6(8) . . ?
C1B C2B H2B1 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 109.5 . . ?
C1B C2B H2B3 109.5 . . ?
H2B1 C2B H2B3 109.5 . . ?
H2B2 C2B H2B3 109.5 . . ?
C1B C3B H3B1 109.5 . . ?
C1B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C1B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 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
C16 C11 C12 C13 1.3(4) . . . . ?
C8 C11 C12 C13 -172.8(3) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C11 C12 C13 C1 174.3(3) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C1 C13 C14 C15 -176.2(3) . . . . ?
C13 C14 C15 C16 2.1(6) . . . . ?
C14 C15 C16 C11 -1.5(5) . . . . ?
C12 C11 C16 C15 -0.2(5) . . . . ?
C8 C11 C16 C15 174.1(3) . . . . ?
C12 C13 C1 O1 -157.4(3) . . . . ?
C14 C13 C1 O1 17.6(5) . . . . ?
C12 C13 C1 N1 18.5(4) . . . . ?
C14 C13 C1 N1 -166.4(3) . . . . ?
O1 C1 N1 C2 -121.5(3) . . . . ?
C13 C1 N1 C2 62.3(3) . . . . ?
O1 C1 N1 C11A 36.8(4) . . . . ?
C13 C1 N1 C11A -139.3(3) . . . . ?
C1 N1 C2 O2 6.5(4) . . . . ?
C11A N1 C2 O2 -149.8(3) . . . . ?
C1 N1 C2 C21 -172.4(2) . . . . ?
C11A N1 C2 C21 31.2(4) . . . . ?
C2 N1 C11A N12A -137.7(3) . . . . ?
C1 N1 C11A N12A 65.2(3) . . . . ?
C2 N1 C11A C16A 45.6(4) . . . . ?
C1 N1 C11A C16A -111.5(3) . . . . ?
C16A C11A N12A C13A -1.3(5) . . . . ?
N1 C11A N12A C13A -177.9(3) . . . . ?
C11A N12A C13A C14A -1.1(5) . . . . ?
N12A C13A C14A F14A -179.0(3) . . . . ?
N12A C13A C14A C15A 1.9(7) . . . . ?
F14A C14A C15A C16A -179.4(4) . . . . ?
C13A C14A C15A C16A -0.3(7) . . . . ?
N12A C11A C16A C15A 2.8(5) . . . . ?
N1 C11A C16A C15A 179.1(3) . . . . ?
C14A C15A C16A C11A -1.9(6) . . . . ?
O2 C2 C21 C22 -140.8(3) . . . . ?
N1 C2 C21 C22 38.1(4) . . . . ?
O2 C2 C21 C26 32.9(4) . . . . ?
N1 C2 C21 C26 -148.2(3) . . . . ?
C26 C21 C22 C23 -1.9(4) . . . . ?
C2 C21 C22 C23 171.7(3) . . . . ?
C21 C22 C23 C24 2.7(4) . . . . ?
C21 C22 C23 C3 -171.1(3) . . . . ?
C22 C23 C24 C25 -1.1(5) . . . . ?
C3 C23 C24 C25 173.0(3) . . . . ?
C23 C24 C25 C26 -1.3(5) . . . . ?
C24 C25 C26 C21 2.1(5) . . . . ?
C22 C21 C26 C25 -0.5(5) . . . . ?
C2 C21 C26 C25 -174.4(3) . . . . ?
C24 C23 C3 O3 -19.8(5) . . . . ?
C22 C23 C3 O3 154.2(3) . . . . ?
C24 C23 C3 N2 164.1(3) . . . . ?
C22 C23 C3 N2 -21.9(4) . . . . ?
O3 C3 N2 C4 122.9(3) . . . . ?
C23 C3 N2 C4 -60.8(3) . . . . ?
O3 C3 N2 C21A -35.5(4) . . . . ?
C23 C3 N2 C21A 140.8(3) . . . . ?
C21A N2 C4 O4 149.2(3) . . . . ?
C3 N2 C4 O4 -7.5(4) . . . . ?
C21A N2 C4 C31 -32.3(4) . . . . ?
C3 N2 C4 C31 171.1(2) . . . . ?
C4 N2 C21A N22A 140.6(3) . . . . ?
C3 N2 C21A N22A -62.4(3) . . . . ?
C4 N2 C21A C26A -40.6(4) . . . . ?
C3 N2 C21A C26A 116.4(3) . . . . ?
C26A C21A N22A C23A 0.0(5) . . . . ?
N2 C21A N22A C23A 178.8(3) . . . . ?
C21A N22A C23A C24A 1.8(6) . . . . ?
N22A C23A C24A F24A 177.7(4) . . . . ?
N22A C23A C24A C25A -2.2(8) . . . . ?
F24A C24A C25A C26A -179.2(4) . . . . ?
C23A C24A C25A C26A 0.6(8) . . . . ?
N22A C21A C26A C25A -1.5(6) . . . . ?
N2 C21A C26A C25A 179.9(3) . . . . ?
C24A C25A C26A C21A 1.1(7) . . . . ?
O4 C4 C31 C32 138.5(3) . . . . ?
N2 C4 C31 C32 -40.0(4) . . . . ?
O4 C4 C31 C36 -35.9(4) . . . . ?
N2 C4 C31 C36 145.6(3) . . . . ?
C36 C31 C32 C33 2.4(5) . . . . ?
C4 C31 C32 C33 -172.0(3) . . . . ?
C31 C32 C33 C34 -2.6(5) . . . . ?
C31 C32 C33 C5 171.4(3) . . . . ?
C32 C33 C34 C35 0.5(5) . . . . ?
C5 C33 C34 C35 -173.7(3) . . . . ?
C33 C34 C35 C36 1.8(6) . . . . ?
C34 C35 C36 C31 -2.1(6) . . . . ?
C32 C31 C36 C35 0.0(5) . . . . ?
C4 C31 C36 C35 174.6(3) . . . . ?
C32 C33 C5 O5 -152.1(3) . . . . ?
C34 C33 C5 O5 22.1(5) . . . . ?
C32 C33 C5 N3 22.5(5) . . . . ?
C34 C33 C5 N3 -163.4(3) . . . . ?
O5 C5 N3 C6 -123.9(3) . . . . ?
C33 C5 N3 C6 61.3(4) . . . . ?
O5 C5 N3 C31A 30.4(4) . . . . ?
C33 C5 N3 C31A -144.3(3) . . . . ?
C5 N3 C6 O6 5.5(4) . . . . ?
C31A N3 C6 O6 -146.8(3) . . . . ?
C5 N3 C6 C41 -172.2(2) . . . . ?
C31A N3 C6 C41 35.4(4) . . . . ?
C6 N3 C31A N32A 38.1(4) . . . . ?
C5 N3 C31A N32A -114.4(3) . . . . ?
C6 N3 C31A C36A -144.2(3) . . . . ?
C5 N3 C31A C36A 63.3(3) . . . . ?
C36A C31A N32A C33A 1.4(5) . . . . ?
N3 C31A N32A C33A 179.0(3) . . . . ?
C31A N32A C33A C34A -1.3(5) . . . . ?
N32A C33A C34A F34A -179.0(3) . . . . ?
N32A C33A C34A C35A 0.2(6) . . . . ?
F34A C34A C35A C36A -179.9(3) . . . . ?
C33A C34A C35A C36A 0.9(5) . . . . ?
N32A C31A C36A C35A -0.4(4) . . . . ?
N3 C31A C36A C35A -177.9(2) . . . . ?
C34A C35A C36A C31A -0.8(4) . . . . ?
O6 C6 C41 C42 -141.4(3) . . . . ?
N3 C6 C41 C42 36.3(4) . . . . ?
O6 C6 C41 C46 31.2(4) . . . . ?
N3 C6 C41 C46 -151.1(3) . . . . ?
C46 C41 C42 C43 -1.2(4) . . . . ?
C6 C41 C42 C43 171.2(3) . . . . ?
C41 C42 C43 C44 1.6(5) . . . . ?
C41 C42 C43 C7 -170.6(3) . . . . ?
C42 C43 C44 C45 0.1(5) . . . . ?
C7 C43 C44 C45 172.6(3) . . . . ?
C43 C44 C45 C46 -2.4(6) . . . . ?
C44 C45 C46 C41 2.8(6) . . . . ?
C42 C41 C46 C45 -1.1(5) . . . . ?
C6 C41 C46 C45 -173.8(3) . . . . ?
C44 C43 C7 O7 -18.7(6) . . . . ?
C42 C43 C7 O7 153.5(4) . . . . ?
C44 C43 C7 N4 166.1(3) . . . . ?
C42 C43 C7 N4 -21.6(5) . . . . ?
O7 C7 N4 C8 122.9(4) . . . . ?
C43 C7 N4 C8 -61.8(4) . . . . ?
O7 C7 N4 C41A -35.5(5) . . . . ?
C43 C7 N4 C41A 139.9(3) . . . . ?
C41A N4 C8 O8 149.5(3) . . . . ?
C7 N4 C8 O8 -7.3(4) . . . . ?
C41A N4 C8 C11 -33.7(4) . . . . ?
C7 N4 C8 C11 169.5(3) . . . . ?
C12 C11 C8 O8 141.6(3) . . . . ?
C16 C11 C8 O8 -32.6(4) . . . . ?
C12 C11 C8 N4 -35.1(4) . . . . ?
C16 C11 C8 N4 150.7(3) . . . . ?
C8 N4 C41A N42A -32.7(4) . . . . ?
C7 N4 C41A N42A 124.3(3) . . . . ?
C8 N4 C41A C46A 147.4(3) . . . . ?
C7 N4 C41A C46A -55.6(3) . . . . ?
C46A C41A N42A C43A -2.1(4) . . . . ?
N4 C41A N42A C43A 178.0(3) . . . . ?
C41A N42A C43A C44A 2.0(5) . . . . ?
N42A C43A C44A F44A -179.7(3) . . . . ?
N42A C43A C44A C45A -0.2(6) . . . . ?
F44A C44A C45A C46A 177.8(3) . . . . ?
C43A C44A C45A C46A -1.6(5) . . . . ?
C44A C45A C46A C41A 1.6(4) . . . . ?
N42A C41A C46A C45A 0.3(4) . . . . ?
N4 C41A C46A C45A -179.8(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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
C2B H2B2 O4 0.96 2.54 3.091(10) 117 3_556 yes
C15 H15 O4 0.93 2.58 3.475(5) 161 1_655 yes
C15A H15A O1A 0.93 2.32 3.240(10) 168 3_556 yes
C24 H24 O1B 0.93 2.44 3.189(12) 138 1_455 yes
C25A H25A O2A 0.93 2.43 3.349(12) 170 2_455 yes
C26A H26A F34A 0.93 2.51 3.383(5) 156 1_455 yes
C33A H33A O2A 0.93 2.53 3.377(11) 152 2_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ClIO3_DMSO_H2O_SQ
_audit_block_doi                 10.5517/cc14n40y
_database_code_depnum_ccdc_archive 'CCDC 1062029'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (ClIO)3:DMSO:H2O
_chemical_melting_point          ?
_chemical_formula_moiety         
'4(C39 H21 Cl3 N6 O6), 2(C1.60 H4.80 O0.80 S0.80), 5.92(C2 H6 O)'
_chemical_formula_sum            'C171.04 H129.12 Cl12 N24 O36.52 S7.52'
_chemical_formula_weight         3771.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   55.0537(10)
_cell_length_b                   36.3597(5)
_cell_length_c                   10.6018(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     21222.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8469
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      63.3

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             7759.4
_exptl_absorpt_coefficient_mu    2.695
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.4438
_exptl_absorpt_correction_T_max  0.9235
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         33213
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4574
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       63
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         63.43
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        62.50
_diffrn_measured_fraction_theta_full 0.995
_reflns_number_total             4574
_reflns_number_gt                4009
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.1092P)²] where P=(Fo²+2Fc²)/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, 1983)'
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_number_reflns         4574
_refine_ls_number_parameters     664
_refine_ls_number_restraints     170
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.058

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
Cl14 Cl -0.00251(3) 0.08419(6) 0.3762(2) 0.1244(7) Uani 1 1 d . . .
Cl24 Cl 0.18488(4) 0.20844(5) 1.05061(12) 0.1119(6) Uani 1 1 d . . .
Cl34 Cl 0.01898(3) 0.03268(6) 0.6510(2) 0.1183(6) Uani 1 1 d . . .
O1 O 0.07446(7) 0.24659(9) 0.4271(4) 0.0856(10) Uani 1 1 d . . .
C1 C 0.07734(8) 0.21437(12) 0.4477(4) 0.0636(10) Uani 1 1 d . . .
N1 N 0.07778(6) 0.18869(10) 0.3434(3) 0.0596(8) Uani 1 1 d . . .
O2 O 0.08326(7) 0.18458(12) 0.1309(3) 0.0900(11) Uani 1 1 d . . .
C2 C 0.08942(8) 0.19764(13) 0.2308(4) 0.0648(10) Uani 1 1 d . . .
O3 O 0.16998(8) 0.27348(9) 0.5000(4) 0.0871(10) Uani 1 1 d . . .
C3 C 0.16289(9) 0.24559(12) 0.4519(4) 0.0642(10) Uani 1 1 d . . .
N2 N 0.16827(6) 0.21058(9) 0.5081(3) 0.0554(7) Uani 1 1 d . . .
O4 O 0.18744(7) 0.19129(10) 0.3289(3) 0.0811(9) Uani 1 1 d . . .
C4 C 0.17957(7) 0.18357(11) 0.4323(4) 0.0585(9) Uani 1 1 d . . .
O5 O 0.13375(6) 0.04089(7) 0.5871(4) 0.0830(10) Uani 1 1 d . . .
C5 C 0.13593(8) 0.07336(11) 0.6031(4) 0.0628(10) Uani 1 1 d . . .
N3 N 0.11628(6) 0.09512(8) 0.6448(3) 0.0551(7) Uani 1 1 d . . .
O6 O 0.13613(6) 0.12528(9) 0.8041(3) 0.0730(8) Uani 1 1 d . . .
C6 C 0.11981(7) 0.12510(11) 0.7282(4) 0.0570(9) Uani 1 1 d . . .
C11 C 0.10272(7) 0.15627(10) 0.7116(4) 0.0539(8) Uani 1 1 d . . .
C12 C 0.09541(7) 0.16667(10) 0.5906(4) 0.0514(8) Uani 1 1 d . . .
H12 H 0.0990 0.1520 0.5214 0.062 Uiso 1 1 calc R . .
C13 C 0.08266(7) 0.19928(11) 0.5752(4) 0.0576(9) Uani 1 1 d . . .
C14 C 0.07624(10) 0.22022(13) 0.6804(5) 0.0737(12) Uani 1 1 d . . .
H14 H 0.0677 0.2421 0.6702 0.088 Uiso 1 1 calc R . .
C15 C 0.08260(10) 0.20857(13) 0.7988(5) 0.0766(12) Uani 1 1 d . . .
H15 H 0.0775 0.2219 0.8689 0.092 Uiso 1 1 calc R . .
C16 C 0.09633(8) 0.17776(12) 0.8153(4) 0.0646(10) Uani 1 1 d . . .
H16 H 0.1014 0.1711 0.8957 0.078 Uiso 1 1 calc R . .
C11A C 0.05905(8) 0.16114(12) 0.3460(4) 0.0649(10) Uani 1 1 d . . .
N12A N 0.04064(7) 0.16984(13) 0.4208(5) 0.0829(11) Uani 1 1 d . . .
C13A C 0.02236(10) 0.14508(19) 0.4287(7) 0.0964(17) Uani 1 1 d . . .
H13A H 0.0094 0.1501 0.4820 0.116 Uiso 1 1 calc R . .
C14A C 0.02228(10) 0.11346(16) 0.3624(6) 0.0852(15) Uani 1 1 d . . .
C15A C 0.04133(11) 0.10523(16) 0.2855(6) 0.0858(14) Uani 1 1 d . . .
H15A H 0.0414 0.0836 0.2389 0.103 Uiso 1 1 calc R . .
C16A C 0.06019(9) 0.12906(13) 0.2778(5) 0.0751(12) Uani 1 1 d . . .
H16A H 0.0736 0.1238 0.2276 0.090 Uiso 1 1 calc R . .
C21 C 0.11065(8) 0.22312(12) 0.2419(4) 0.0632(10) Uani 1 1 d . . .
C22 C 0.12777(8) 0.22019(11) 0.3352(4) 0.0587(9) Uani 1 1 d . . .
H22 H 0.1267 0.2013 0.3940 0.070 Uiso 1 1 calc R . .
C23 C 0.14675(8) 0.24534(11) 0.3423(4) 0.0598(9) Uani 1 1 d . . .
C24 C 0.14814(9) 0.27375(13) 0.2536(5) 0.0733(12) Uani 1 1 d . . .
H24 H 0.1605 0.2912 0.2586 0.088 Uiso 1 1 calc R . .
C25 C 0.13124(10) 0.27572(14) 0.1594(5) 0.0833(14) Uani 1 1 d . . .
H25 H 0.1325 0.2943 0.0994 0.100 Uiso 1 1 calc R . .
C26 C 0.11272(10) 0.25126(15) 0.1515(4) 0.0778(12) Uani 1 1 d . . .
H26 H 0.1014 0.2531 0.0866 0.093 Uiso 1 1 calc R . .
C21A C 0.17164(7) 0.21000(10) 0.6414(4) 0.0522(8) Uani 1 1 d . . .
N22A N 0.19346(7) 0.19991(11) 0.6825(4) 0.0683(9) Uani 1 1 d . . .
C23A C 0.19673(10) 0.19971(16) 0.8062(5) 0.0777(12) Uani 1 1 d . . .
H23A H 0.2118 0.1926 0.8375 0.093 Uiso 1 1 calc R . .
C24A C 0.17882(10) 0.20960(13) 0.8910(4) 0.0726(12) Uani 1 1 d . . .
C25A C 0.15649(9) 0.22021(12) 0.8465(4) 0.0683(11) Uani 1 1 d . . .
H25A H 0.1442 0.2271 0.9016 0.082 Uiso 1 1 calc R . .
C26A C 0.15287(8) 0.22036(11) 0.7191(4) 0.0619(9) Uani 1 1 d . . .
H26A H 0.1380 0.2273 0.6855 0.074 Uiso 1 1 calc R . .
C31 C 0.17973(7) 0.14562(12) 0.4823(4) 0.0596(9) Uani 1 1 d . . .
C32 C 0.15905(7) 0.12997(11) 0.5334(4) 0.0561(9) Uani 1 1 d . . .
H32 H 0.1451 0.1441 0.5442 0.067 Uiso 1 1 calc R . .
C33 C 0.15898(7) 0.09319(10) 0.5687(4) 0.0584(9) Uani 1 1 d . . .
C34 C 0.17993(9) 0.07249(13) 0.5550(6) 0.0792(13) Uani 1 1 d . . .
H34 H 0.1800 0.0479 0.5793 0.095 Uiso 1 1 calc R . .
C35 C 0.20056(10) 0.08789(15) 0.5061(8) 0.0963(18) Uani 1 1 d . . .
H35 H 0.2147 0.0739 0.5003 0.116 Uiso 1 1 calc R . .
C36 C 0.20065(8) 0.12365(14) 0.4656(6) 0.0779(12) Uani 1 1 d . . .
H36 H 0.2144 0.1334 0.4273 0.094 Uiso 1 1 calc R . .
C31A C 0.09241(7) 0.07983(10) 0.6387(4) 0.0552(8) Uani 1 1 d . . .
N32A N 0.08089(7) 0.07971(10) 0.7487(4) 0.0660(9) Uani 1 1 d . . .
C33A C 0.05851(9) 0.06572(15) 0.7501(5) 0.0787(13) Uani 1 1 d . . .
H33A H 0.0498 0.0655 0.8254 0.094 Uiso 1 1 calc R . .
C34A C 0.04778(8) 0.05136(13) 0.6418(6) 0.0767(13) Uani 1 1 d . . .
C35A C 0.05972(9) 0.05181(13) 0.5309(6) 0.0762(12) Uani 1 1 d . . .
H35A H 0.0525 0.0424 0.4583 0.091 Uiso 1 1 calc R . .
C36A C 0.08293(8) 0.06657(12) 0.5272(5) 0.0659(10) Uani 1 1 d . . .
H36A H 0.0918 0.0675 0.4525 0.079 Uiso 1 1 calc R . .
S1A S 0.12461(4) 0.10642(6) 0.20247(19) 0.0904(5) Uani 0.75 1 d P A 1
O1A O 0.11894(16) 0.1259(4) 0.3270(9) 0.081(2) Uani 0.75 1 d P A 1
C1A C 0.1418(2) 0.0701(4) 0.2416(15) 0.115(4) Uani 0.75 1 d P A 1
H1A1 H 0.1546 0.0673 0.1809 0.173 Uiso 0.75 1 calc PR A 1
H1A2 H 0.1320 0.0484 0.2428 0.173 Uiso 0.75 1 calc PR A 1
H1A3 H 0.1487 0.0740 0.3237 0.173 Uiso 0.75 1 calc PR A 1
C2A C 0.1438(2) 0.1373(3) 0.1214(10) 0.128(4) Uani 0.75 1 d P A 1
H2A1 H 0.1595 0.1261 0.1095 0.192 Uiso 0.75 1 calc PR A 1
H2A2 H 0.1456 0.1594 0.1698 0.192 Uiso 0.75 1 calc PR A 1
H2A3 H 0.1369 0.1430 0.0407 0.192 Uiso 0.75 1 calc PR A 1
S1B S 0.14067(12) 0.11538(18) 0.2448(6) 0.0887(14) Uani 0.25 1 d PDU B 2
O1B O 0.1202(8) 0.1205(15) 0.324(5) 0.135(16) Uani 0.25 1 d PDU B 2
C1B C 0.1518(7) 0.0723(9) 0.225(5) 0.123(13) Uani 0.25 1 d PDU B 2
H1B1 H 0.1376 0.0562 0.1988 0.185 Uiso 0.25 1 d P C 2
H1B2 H 0.1592 0.0631 0.2922 0.185 Uiso 0.25 1 d P D 2
H1B3 H 0.1622 0.0722 0.1485 0.185 Uiso 0.25 1 d P E 2
C2B C 0.1648(9) 0.1444(15) 0.229(8) 0.24(2) Uani 0.25 1 d PDU B 2
H2B1 H 0.1797 0.1308 0.2395 0.356 Uiso 0.25 1 d P F 2
H2B2 H 0.1636 0.1651 0.2714 0.356 Uiso 0.25 1 d P G 2
H2B3 H 0.1654 0.1509 0.1320 0.356 Uiso 0.25 1 d P H 2
S1C S 0.01891(11) 0.01057(18) 0.0272(7) 0.1369(18) Uani 0.40 1 d PDU I -1
O1C O 0.0285(4) 0.0474(5) 0.031(2) 0.091(5) Uani 0.20 1 d PDU I -1
C1C C 0.0147(3) -0.0042(5) 0.1764(19) 0.119(5) Uani 0.40 1 d PDU I -1
H1C1 H 0.0237 -0.0264 0.1897 0.178 Uiso 0.40 1 calc PR I -1
H1C2 H -0.0023 -0.0090 0.1900 0.178 Uiso 0.40 1 calc PR I -1
H1C3 H 0.0201 0.0143 0.2343 0.178 Uiso 0.40 1 calc PR I -1
C2C C 0.0077(6) -0.0175(7) -0.059(3) 0.174(9) Uani 0.40 1 d PDU I -1
H2C1 H 0.0202 -0.0294 -0.1068 0.261 Uiso 0.40 1 calc PR I -1
H2C2 H -0.0035 -0.0056 -0.1147 0.261 Uiso 0.40 1 calc PR I -1
H2C3 H -0.0008 -0.0355 -0.0092 0.261 Uiso 0.40 1 calc PR I -1
O2C O -0.0019(7) 0.0295(11) 0.083(4) 0.173(11) Uani 0.20 1 d PDU J -2
S1D S 0.01002(17) 0.1206(4) 0.9905(10) 0.212(4) Uani 0.48 1 d PDU K 1
O1D O 0.0024(5) 0.1557(7) 1.051(4) 0.290(12) Uani 0.48 1 d PDU K 1
C1D C 0.0354(3) 0.1409(5) 0.944(2) 0.136(5) Uani 0.48 1 d PDU K 1
H1D1 H 0.0357 0.1423 0.8537 0.204 Uiso 0.48 1 calc PR K 1
H1D2 H 0.0491 0.1270 0.9732 0.204 Uiso 0.48 1 calc PR K 1
H1D3 H 0.0361 0.1653 0.9787 0.204 Uiso 0.48 1 calc PR K 1
C2D C -0.0105(5) 0.1105(9) 0.876(3) 0.203(11) Uani 0.48 1 d PDU K 1
H2D1 H -0.0225 0.1296 0.8719 0.304 Uiso 0.48 1 calc PR K 1
H2D2 H -0.0182 0.0875 0.8948 0.304 Uiso 0.48 1 calc PR K 1
H2D3 H -0.0023 0.1088 0.7961 0.304 Uiso 0.48 1 calc PR K 1
O1W O 0.0215(5) 0.0733(15) 1.023(4) 0.33(2) Uani 0.45 1 d P L 2
O2W O 0.0176(6) 0.1414(6) 0.830(3) 0.350(13) Uani 0.80 1 d P M 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
Cl14 C14A 1.737(5) . ?
Cl24 C24A 1.725(5) . ?
Cl34 C34A 1.727(5) . ?
O1 C1 1.202(5) . ?
C1 N1 1.448(6) . ?
C1 C13 1.488(6) . ?
N1 C2 1.393(6) . ?
N1 C11A 1.438(6) . ?
O2 C2 1.209(6) . ?
C2 C21 1.496(6) . ?
O3 C3 1.200(5) . ?
C3 N2 1.436(5) . ?
C3 C23 1.463(6) . ?
N2 C4 1.413(5) . ?
N2 C21A 1.426(5) . ?
O4 C4 1.212(5) . ?
C4 C31 1.478(6) . ?
O5 C5 1.199(5) . ?
C5 N3 1.411(5) . ?
C5 C33 1.504(6) . ?
N3 C6 1.417(5) . ?
N3 C31A 1.428(5) . ?
O6 C6 1.207(5) . ?
C6 C11 1.483(6) . ?
C11 C16 1.394(6) . ?
C11 C12 1.397(6) . ?
C12 C13 1.387(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.396(6) . ?
C14 C15 1.370(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11A N12A 1.326(6) . ?
C11A C16A 1.373(7) . ?
N12A C13A 1.352(7) . ?
C13A C14A 1.348(9) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.361(9) . ?
C15A C16A 1.355(7) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21 C22 1.370(6) . ?
C21 C26 1.406(6) . ?
C22 C23 1.391(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.400(6) . ?
C24 C25 1.366(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.356(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21A N22A 1.330(5) . ?
C21A C26A 1.374(6) . ?
N22A C23A 1.324(6) . ?
C23A C24A 1.382(7) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.372(8) . ?
C25A C26A 1.365(7) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
C31 C32 1.383(6) . ?
C31 C36 1.413(6) . ?
C32 C33 1.389(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.385(6) . ?
C34 C35 1.368(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.369(8) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C31A N32A 1.328(6) . ?
C31A C36A 1.379(6) . ?
N32A C33A 1.333(6) . ?
C33A C34A 1.394(8) . ?
C33A H33A 0.9300 . ?
C34A C35A 1.347(8) . ?
C35A C36A 1.386(7) . ?
C35A H35A 0.9300 . ?
C36A H36A 0.9300 . ?
S1A O1A 1.529(10) . ?
S1A C1A 1.676(14) . ?
S1A C2A 1.765(12) . ?
S1B O1B 1.42(3) . ?
S1B C1B 1.69(2) . ?
S1B C2B 1.71(3) . ?
S1C O1C 1.441(16) . ?
S1C C2C 1.50(2) . ?
S1C C1C 1.687(19) . ?
S1D O1D 1.49(2) . ?
S1D C1D 1.656(18) . ?
S1D C2D 1.70(2) . ?

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
O1 C1 N1 119.4(4) . . ?
O1 C1 C13 123.4(4) . . ?
N1 C1 C13 116.9(3) . . ?
C2 N1 C11A 120.6(3) . . ?
C2 N1 C1 120.8(4) . . ?
C11A N1 C1 115.0(4) . . ?
O2 C2 N1 122.0(4) . . ?
O2 C2 C21 122.1(4) . . ?
N1 C2 C21 115.9(4) . . ?
O3 C3 N2 120.4(4) . . ?
O3 C3 C23 122.7(4) . . ?
N2 C3 C23 116.7(3) . . ?
C4 N2 C21A 119.7(3) . . ?
C4 N2 C3 118.1(3) . . ?
C21A N2 C3 116.8(3) . . ?
O4 C4 N2 120.7(4) . . ?
O4 C4 C31 122.6(4) . . ?
N2 C4 C31 116.6(3) . . ?
O5 C5 N3 121.3(4) . . ?
O5 C5 C33 121.5(4) . . ?
N3 C5 C33 117.0(3) . . ?
C5 N3 C6 121.5(3) . . ?
C5 N3 C31A 118.2(3) . . ?
C6 N3 C31A 117.0(3) . . ?
O6 C6 N3 121.5(4) . . ?
O6 C6 C11 123.2(4) . . ?
N3 C6 C11 115.3(3) . . ?
C16 C11 C12 120.0(4) . . ?
C16 C11 C6 119.7(4) . . ?
C12 C11 C6 119.9(3) . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 C1 121.4(4) . . ?
C14 C13 C1 118.3(4) . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
N12A C11A C16A 123.5(4) . . ?
N12A C11A N1 113.2(4) . . ?
C16A C11A N1 123.3(4) . . ?
C11A N12A C13A 116.5(5) . . ?
C14A C13A N12A 122.6(6) . . ?
C14A C13A H13A 118.7 . . ?
N12A C13A H13A 118.7 . . ?
C13A C14A C15A 119.8(5) . . ?
C13A C14A Cl14 118.8(5) . . ?
C15A C14A Cl14 121.4(5) . . ?
C16A C15A C14A 119.1(5) . . ?
C16A C15A H15A 120.5 . . ?
C14A C15A H15A 120.5 . . ?
C15A C16A C11A 118.5(5) . . ?
C15A C16A H16A 120.8 . . ?
C11A C16A H16A 120.8 . . ?
C22 C21 C26 119.5(4) . . ?
C22 C21 C2 123.1(4) . . ?
C26 C21 C2 117.4(4) . . ?
C21 C22 C23 120.3(4) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 C3 120.3(3) . . ?
C24 C23 C3 119.7(4) . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C26 C25 C24 121.5(4) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C21 119.7(4) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
N22A C21A C26A 124.0(4) . . ?
N22A C21A N2 116.5(4) . . ?
C26A C21A N2 119.5(4) . . ?
C23A N22A C21A 116.7(4) . . ?
N22A C23A C24A 123.1(5) . . ?
N22A C23A H23A 118.5 . . ?
C24A C23A H23A 118.5 . . ?
C25A C24A C23A 119.2(4) . . ?
C25A C24A Cl24 121.2(4) . . ?
C23A C24A Cl24 119.6(4) . . ?
C26A C25A C24A 118.2(4) . . ?
C26A C25A H25A 120.9 . . ?
C24A C25A H25A 120.9 . . ?
C25A C26A C21A 118.8(4) . . ?
C25A C26A H26A 120.6 . . ?
C21A C26A H26A 120.6 . . ?
C32 C31 C36 119.2(4) . . ?
C32 C31 C4 121.3(4) . . ?
C36 C31 C4 119.2(4) . . ?
C31 C32 C33 120.2(4) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C34 C33 C32 119.5(4) . . ?
C34 C33 C5 117.9(4) . . ?
C32 C33 C5 121.9(4) . . ?
C35 C34 C33 120.6(5) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 120.7(5) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C31 119.6(5) . . ?
C35 C36 H36 120.2 . . ?
C31 C36 H36 120.2 . . ?
N32A C31A C36A 124.8(4) . . ?
N32A C31A N3 113.6(4) . . ?
C36A C31A N3 121.6(4) . . ?
C31A N32A C33A 116.9(4) . . ?
N32A C33A C34A 121.7(5) . . ?
N32A C33A H33A 119.2 . . ?
C34A C33A H33A 119.2 . . ?
C35A C34A C33A 120.5(4) . . ?
C35A C34A Cl34 120.1(4) . . ?
C33A C34A Cl34 119.3(4) . . ?
C34A C35A C36A 118.6(5) . . ?
C34A C35A H35A 120.7 . . ?
C36A C35A H35A 120.7 . . ?
C31A C36A C35A 117.4(4) . . ?
C31A C36A H36A 121.3 . . ?
C35A C36A H36A 121.3 . . ?
O1A S1A C1A 105.4(7) . . ?
O1A S1A C2A 104.4(6) . . ?
C1A S1A C2A 106.4(6) . . ?
S1A C1A H1B1 102.4(15) . . ?
S1A C1A H1B2 140.9(10) . . ?
S1A C1A H1B3 102.7(9) . . ?
S1A C2A H2B3 138.8(9) . . ?
O1B S1B C1B 119(3) . . ?
O1B S1B C2B 127(3) . . ?
C1B S1B C2B 106(2) . . ?
S1B C1B H1B1 107(2) . . ?
S1B C1B H1B2 115(4) . . ?
H1B1 C1B H1B2 111(4) . . ?
S1B C1B H1B3 108(3) . . ?
H1B1 C1B H1B3 102(4) . . ?
H1B2 C1B H1B3 113(3) . . ?
S1B C2B H2B1 110(4) . . ?
S1B C2B H2B2 115(4) . . ?
H2B1 C2B H2B2 116(7) . . ?
S1B C2B H2B3 105(5) . . ?
H2B1 C2B H2B3 102(6) . . ?
H2B2 C2B H2B3 108(7) . . ?
O1C S1C C2C 143.0(16) . . ?
O1C S1C C1C 108.9(12) . . ?
C2C S1C C1C 107.1(13) . . ?
O1D S1D C1D 89.2(14) . . ?
O1D S1D C2D 107.9(18) . . ?
C1D S1D C2D 116.5(14) . . ?

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
O1 C1 N1 C2 39.9(6) . . . . ?
C13 C1 N1 C2 -135.0(4) . . . . ?
O1 C1 N1 C11A -118.8(5) . . . . ?
C13 C1 N1 C11A 66.3(5) . . . . ?
C11A N1 C2 O2 4.9(7) . . . . ?
C1 N1 C2 O2 -152.6(5) . . . . ?
C11A N1 C2 C21 -172.6(4) . . . . ?
C1 N1 C2 C21 29.9(6) . . . . ?
O3 C3 N2 C4 -126.0(5) . . . . ?
C23 C3 N2 C4 59.5(5) . . . . ?
O3 C3 N2 C21A 28.1(6) . . . . ?
C23 C3 N2 C21A -146.3(4) . . . . ?
C21A N2 C4 O4 -143.6(4) . . . . ?
C3 N2 C4 O4 9.8(6) . . . . ?
C21A N2 C4 C31 40.3(5) . . . . ?
C3 N2 C4 C31 -166.3(4) . . . . ?
O5 C5 N3 C6 143.8(4) . . . . ?
C33 C5 N3 C6 -41.4(5) . . . . ?
O5 C5 N3 C31A -14.9(6) . . . . ?
C33 C5 N3 C31A 159.8(4) . . . . ?
C5 N3 C6 O6 -29.8(6) . . . . ?
C31A N3 C6 O6 129.2(4) . . . . ?
C5 N3 C6 C11 148.1(3) . . . . ?
C31A N3 C6 C11 -53.0(4) . . . . ?
O6 C6 C11 C16 -32.7(6) . . . . ?
N3 C6 C11 C16 149.6(4) . . . . ?
O6 C6 C11 C12 139.7(4) . . . . ?
N3 C6 C11 C12 -38.1(5) . . . . ?
C16 C11 C12 C13 2.6(6) . . . . ?
C6 C11 C12 C13 -169.7(3) . . . . ?
C11 C12 C13 C14 -3.2(6) . . . . ?
C11 C12 C13 C1 171.5(4) . . . . ?
O1 C1 C13 C12 -152.8(4) . . . . ?
N1 C1 C13 C12 21.9(6) . . . . ?
O1 C1 C13 C14 22.0(7) . . . . ?
N1 C1 C13 C14 -163.3(4) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C1 C13 C14 C15 -174.8(5) . . . . ?
C13 C14 C15 C16 3.7(8) . . . . ?
C14 C15 C16 C11 -4.3(8) . . . . ?
C12 C11 C16 C15 1.1(6) . . . . ?
C6 C11 C16 C15 173.5(4) . . . . ?
C2 N1 C11A N12A -140.3(4) . . . . ?
C1 N1 C11A N12A 18.4(5) . . . . ?
C2 N1 C11A C16A 39.8(6) . . . . ?
C1 N1 C11A C16A -161.5(4) . . . . ?
C16A C11A N12A C13A 0.3(7) . . . . ?
N1 C11A N12A C13A -179.6(5) . . . . ?
C11A N12A C13A C14A -1.5(9) . . . . ?
N12A C13A C14A C15A 1.2(10) . . . . ?
N12A C13A C14A Cl14 -178.2(5) . . . . ?
C13A C14A C15A C16A 0.4(9) . . . . ?
Cl14 C14A C15A C16A 179.8(4) . . . . ?
C14A C15A C16A C11A -1.5(8) . . . . ?
N12A C11A C16A C15A 1.2(8) . . . . ?
N1 C11A C16A C15A -178.9(4) . . . . ?
O2 C2 C21 C22 -135.3(5) . . . . ?
N1 C2 C21 C22 42.2(6) . . . . ?
O2 C2 C21 C26 44.9(7) . . . . ?
N1 C2 C21 C26 -137.6(5) . . . . ?
C26 C21 C22 C23 1.5(7) . . . . ?
C2 C21 C22 C23 -178.3(4) . . . . ?
C21 C22 C23 C24 0.2(7) . . . . ?
C21 C22 C23 C3 170.9(4) . . . . ?
O3 C3 C23 C22 -139.3(5) . . . . ?
N2 C3 C23 C22 35.1(6) . . . . ?
O3 C3 C23 C24 31.4(7) . . . . ?
N2 C3 C23 C24 -154.3(4) . . . . ?
C22 C23 C24 C25 -1.8(8) . . . . ?
C3 C23 C24 C25 -172.5(5) . . . . ?
C23 C24 C25 C26 1.6(9) . . . . ?
C24 C25 C26 C21 0.1(9) . . . . ?
C22 C21 C26 C25 -1.6(8) . . . . ?
C2 C21 C26 C25 178.1(5) . . . . ?
C4 N2 C21A N22A 36.5(5) . . . . ?
C3 N2 C21A N22A -117.2(4) . . . . ?
C4 N2 C21A C26A -144.9(4) . . . . ?
C3 N2 C21A C26A 61.4(5) . . . . ?
C26A C21A N22A C23A 0.7(7) . . . . ?
N2 C21A N22A C23A 179.3(4) . . . . ?
C21A N22A C23A C24A -0.5(8) . . . . ?
N22A C23A C24A C25A 0.0(8) . . . . ?
N22A C23A C24A Cl24 -180.0(5) . . . . ?
C23A C24A C25A C26A 0.3(7) . . . . ?
Cl24 C24A C25A C26A -179.7(4) . . . . ?
C24A C25A C26A C21A -0.1(7) . . . . ?
N22A C21A C26A C25A -0.4(6) . . . . ?
N2 C21A C26A C25A -179.0(4) . . . . ?
O4 C4 C31 C32 -130.1(5) . . . . ?
N2 C4 C31 C32 45.9(5) . . . . ?
O4 C4 C31 C36 43.2(6) . . . . ?
N2 C4 C31 C36 -140.8(4) . . . . ?
C36 C31 C32 C33 0.5(6) . . . . ?
C4 C31 C32 C33 173.8(4) . . . . ?
C31 C32 C33 C34 1.5(7) . . . . ?
C31 C32 C33 C5 -169.1(4) . . . . ?
O5 C5 C33 C34 -19.4(7) . . . . ?
N3 C5 C33 C34 165.8(4) . . . . ?
O5 C5 C33 C32 151.3(5) . . . . ?
N3 C5 C33 C32 -23.5(6) . . . . ?
C32 C33 C34 C35 -0.6(8) . . . . ?
C5 C33 C34 C35 170.3(6) . . . . ?
C33 C34 C35 C36 -2.3(10) . . . . ?
C34 C35 C36 C31 4.3(10) . . . . ?
C32 C31 C36 C35 -3.4(8) . . . . ?
C4 C31 C36 C35 -176.8(5) . . . . ?
C5 N3 C31A N32A 123.9(4) . . . . ?
C6 N3 C31A N32A -35.8(5) . . . . ?
C5 N3 C31A C36A -55.8(5) . . . . ?
C6 N3 C31A C36A 144.5(4) . . . . ?
C36A C31A N32A C33A -0.1(6) . . . . ?
N3 C31A N32A C33A -179.8(4) . . . . ?
C31A N32A C33A C34A 0.9(7) . . . . ?
N32A C33A C34A C35A -1.1(8) . . . . ?
N32A C33A C34A Cl34 178.5(4) . . . . ?
C33A C34A C35A C36A 0.5(7) . . . . ?
Cl34 C34A C35A C36A -179.2(3) . . . . ?
N32A C31A C36A C35A -0.5(6) . . . . ?
N3 C31A C36A C35A 179.2(4) . . . . ?
C34A C35A C36A C31A 0.3(7) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ClIO4_CH2Cl2
_audit_block_doi                 10.5517/cc14n41z
_database_code_depnum_ccdc_archive 'CCDC 1062030'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (ClIO)4:CH2Cl2
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C52 H28 CL4 N8 O8), C2 H4 CL4'
_chemical_formula_sum            'C106 H60 Cl12 N16 O16'
_chemical_formula_weight         2239.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c c n'
_symmetry_space_group_name_Hall  '-p 2ab 2ac'

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

_cell_length_a                   13.8337(1)
_cell_length_b                   19.0181(1)
_cell_length_c                   19.0737(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5018.11(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9475
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      63.2

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2280
_exptl_absorpt_coefficient_mu    3.670
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.3684
_exptl_absorpt_correction_T_max  0.7219
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         30152
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_reflns_number            28390
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.95
_diffrn_reflns_theta_max         63.30
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        62.50
_diffrn_measured_fraction_theta_full 1.000
_reflns_number_total             4062
_reflns_number_gt                3420
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.0628P)²+1.3728P] where P=(Fo²+2Fc²)/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         4062
_refine_ls_number_parameters     487
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.032

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
Cl14 Cl 0.88323(7) -0.01673(4) -0.11396(4) 0.0935(3) Uani 1 1 d D . .
Cl24 Cl 0.36596(6) 0.14441(6) 0.28989(5) 0.1215(4) Uani 1 1 d D . .
O1 O 0.9631(2) 0.30854(10) -0.10245(9) 0.1170(10) Uani 1 1 d . . .
C1 C 0.9456(2) 0.31744(11) -0.04165(12) 0.0692(7) Uani 1 1 d . A .
N1 N 0.95540(14) 0.26004(9) 0.00646(8) 0.0558(4) Uani 1 1 d D . .
O2 O 1.05440(16) 0.32456(9) 0.07544(10) 0.0842(6) Uani 1 1 d . . .
C2 C 1.00937(18) 0.27050(11) 0.06728(11) 0.0598(5) Uani 1 1 d . A .
O3 O 0.82376(15) 0.08886(14) 0.28887(9) 0.1001(7) Uani 1 1 d . . .
C3 C 0.83318(17) 0.10477(13) 0.22835(11) 0.0630(6) Uani 1 1 d . A .
N2 N 0.75408(15) 0.09577(9) 0.18087(9) 0.0564(4) Uani 1 1 d D . .
O4 O 0.84514(15) 0.01918(10) 0.11937(11) 0.0895(6) Uani 1 1 d . . .
C4 C 0.77118(18) 0.05302(11) 0.12248(12) 0.0619(6) Uani 1 1 d . . .
C11 C 0.79990(17) 0.44602(10) 0.06435(11) 0.0564(5) Uani 1 1 d . . .
C12 C 0.84730(17) 0.38499(10) 0.04494(10) 0.0555(5) Uani 1 1 d . A .
H12 H 0.8400 0.3445 0.0717 0.067 Uiso 1 1 calc R . .
C13 C 0.90538(18) 0.38390(11) -0.01402(11) 0.0585(5) Uani 1 1 d . . .
C14 C 0.9182(2) 0.44533(12) -0.05276(12) 0.0673(6) Uani 1 1 d . A .
H14 H 0.9577 0.4450 -0.0922 0.081 Uiso 1 1 calc R . .
C15 C 0.8729(2) 0.50625(12) -0.03305(13) 0.0734(7) Uani 1 1 d . . .
H15 H 0.8829 0.5473 -0.0585 0.088 Uiso 1 1 calc R A .
C16 C 0.8125(2) 0.50682(11) 0.02447(13) 0.0690(6) Uani 1 1 d . A .
H16 H 0.7801 0.5479 0.0367 0.083 Uiso 1 1 calc R . .
C11A C 0.9419(11) 0.1895(6) -0.0205(8) 0.038(3) Uani 0.50 1 d PD A 1
N12A N 0.8550(10) 0.1799(7) -0.0463(8) 0.052(3) Uani 0.50 1 d PD A 1
C13A C 0.8441(12) 0.1172(9) -0.0751(10) 0.058(4) Uani 0.50 1 d PD A 1
H13A H 0.7828 0.1064 -0.0920 0.070 Uiso 0.50 1 calc PR A 1
C14A C 0.9138(10) 0.0665(7) -0.0828(9) 0.043(3) Uani 0.50 1 d PD A 1
C15A C 1.0012(9) 0.0752(6) -0.0491(7) 0.0427(19) Uani 0.50 1 d PD A 1
H15A H 1.0466 0.0393 -0.0459 0.051 Uiso 0.50 1 calc PR A 1
C16A C 1.0171(16) 0.1414(8) -0.0202(13) 0.055(4) Uani 0.50 1 d PD A 1
H16A H 1.0768 0.1531 -0.0010 0.066 Uiso 0.50 1 calc PR A 1
C11B C 0.9336(14) 0.1938(6) -0.0249(10) 0.060(6) Uani 0.50 1 d PD A 2
N12B N 1.0057(12) 0.1487(8) -0.0247(10) 0.055(3) Uani 0.50 1 d PD A 2
C13B C 0.9833(11) 0.0867(7) -0.0524(9) 0.069(4) Uani 0.50 1 d PD A 2
H13B H 1.0342 0.0554 -0.0580 0.083 Uiso 0.50 1 calc PR A 2
C14B C 0.8940(11) 0.0632(8) -0.0738(10) 0.050(3) Uani 0.50 1 d PD A 2
C15B C 0.8234(12) 0.1132(8) -0.0815(9) 0.047(2) Uani 0.50 1 d PD A 2
H15B H 0.7658 0.1039 -0.1048 0.056 Uiso 0.50 1 calc PR A 2
C16B C 0.8431(15) 0.1788(10) -0.0523(10) 0.062(4) Uani 0.50 1 d PD A 2
H16B H 0.7949 0.2129 -0.0512 0.074 Uiso 0.50 1 calc PR A 2
C21 C 1.00714(16) 0.21561(11) 0.12316(10) 0.0547(5) Uani 1 1 d . . .
C22 C 0.92355(16) 0.18017(10) 0.14149(10) 0.0523(5) Uani 1 1 d . A .
H22 H 0.8681 0.1850 0.1144 0.063 Uiso 1 1 calc R . .
C23 C 0.92271(16) 0.13710(11) 0.20078(10) 0.0530(5) Uani 1 1 d . . .
C24 C 1.00686(18) 0.12884(12) 0.23964(11) 0.0616(6) Uani 1 1 d . A .
H24 H 1.0065 0.1004 0.2793 0.074 Uiso 1 1 calc R . .
C25 C 1.09049(19) 0.16227(14) 0.22008(12) 0.0674(6) Uani 1 1 d . . .
H25 H 1.1471 0.1551 0.2453 0.081 Uiso 1 1 calc R A .
C26 C 1.09035(18) 0.20665(12) 0.16280(12) 0.0644(6) Uani 1 1 d . A .
H26 H 1.1464 0.2307 0.1507 0.077 Uiso 1 1 calc R . .
C21A C 0.6599(6) 0.1097(11) 0.2111(9) 0.042(4) Uani 0.50 1 d PD B 1
N22A N 0.6437(11) 0.1666(9) 0.2375(9) 0.078(5) Uani 0.50 1 d P B 1
C23A C 0.5527(16) 0.1802(12) 0.2696(11) 0.063(6) Uani 0.50 1 d P B 1
H23A H 0.5395 0.2198 0.2966 0.075 Uiso 0.50 1 calc PR B 1
C24A C 0.4768(12) 0.1200(11) 0.2536(12) 0.053(3) Uani 0.50 1 d PD B 1
C25A C 0.5000(16) 0.0715(13) 0.2335(13) 0.071(5) Uani 0.50 1 d P B 1
H25A H 0.4538 0.0361 0.2306 0.085 Uiso 0.50 1 calc PR B 1
C26A C 0.596(3) 0.0540(13) 0.2099(12) 0.060(4) Uani 0.50 1 d P B 1
H26A H 0.6137 0.0092 0.1953 0.072 Uiso 0.50 1 calc PR B 1
C21B C 0.6576(9) 0.1018(13) 0.2054(10) 0.065(6) Uani 0.50 1 d PD B 2
N22B N 0.590(2) 0.0566(11) 0.1931(10) 0.055(3) Uani 0.50 1 d P B 2
C23B C 0.5055(16) 0.0644(13) 0.2176(12) 0.065(4) Uani 0.50 1 d P B 2
H23B H 0.4571 0.0312 0.2105 0.078 Uiso 0.50 1 calc PR B 2
C24B C 0.4863(11) 0.1388(10) 0.2638(12) 0.051(4) Uani 0.50 1 d PD B 2
C25B C 0.548(2) 0.1786(12) 0.2654(13) 0.085(9) Uani 0.50 1 d P B 2
H25B H 0.5327 0.2225 0.2839 0.102 Uiso 0.50 1 calc PR B 2
C26B C 0.6385(12) 0.1693(5) 0.2436(8) 0.056(5) Uani 0.50 1 d P B 2
H26B H 0.6867 0.2025 0.2516 0.067 Uiso 0.50 1 calc PR B 2
Cl1A Cl 0.1709(8) 0.3108(5) -0.1028(3) 0.107(3) Uani 0.20 1 d PD C -1
C1A C 0.2244(13) 0.2417(10) -0.0474(10) 0.104(13) Uani 0.20 1 d PD C -1
H1A1 H 0.1781 0.2050 -0.0362 0.125 Uiso 0.20 1 calc PR C -1
H1A2 H 0.2812 0.2210 -0.0688 0.125 Uiso 0.20 1 calc PR C -1
Cl2A Cl 0.2538(4) 0.2922(5) 0.0261(2) 0.127(3) Uani 0.20 1 d PD C -1
Cl1B Cl 0.3121(7) 0.1992(5) -0.0946(5) 0.173(4) Uani 0.30 1 d PD D -2
C2B C 0.2200(18) 0.2467(16) -0.0602(12) 0.29(3) Uani 0.30 1 d PD D -2
H2B1 H 0.1574 0.2388 -0.0818 0.346 Uiso 0.30 1 calc PR D -2
H2B2 H 0.2334 0.2964 -0.0538 0.346 Uiso 0.30 1 calc PR D -2
Cl2B Cl 0.2445(9) 0.1942(7) 0.0119(8) 0.310(7) Uani 0.30 1 d PD D -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
Cl14 C14B 1.709(14) . ?
Cl14 C14A 1.742(12) . ?
Cl24 C24B 1.741(15) . ?
Cl24 C24A 1.746(15) . ?
O1 C1 1.197(3) . ?
C1 N1 1.432(3) . ?
C1 C13 1.478(3) . ?
N1 C2 1.394(3) . ?
N1 C11B 1.426(9) . ?
N1 C11A 1.449(7) . ?
O2 C2 1.212(3) . ?
C2 C21 1.492(3) . ?
O3 C3 1.200(3) . ?
C3 N2 1.431(3) . ?
C3 C23 1.479(3) . ?
N2 C4 1.399(3) . ?
N2 C21B 1.419(9) . ?
N2 C21A 1.449(7) . ?
O4 C4 1.210(3) . ?
C4 C11 1.482(3) 2_655 ?
C11 C12 1.384(3) . ?
C11 C16 1.395(3) . ?
C11 C4 1.482(3) 2_655 ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(3) . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11A N12A 1.311(9) . ?
C11A C16A 1.384(10) . ?
N12A C13A 1.322(9) . ?
C13A C14A 1.372(9) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.380(9) . ?
C15A C16A 1.392(9) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C11B N12B 1.315(9) . ?
C11B C16B 1.387(10) . ?
N12B C13B 1.329(9) . ?
C13B C14B 1.375(9) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.372(9) . ?
C15B C16B 1.391(9) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21 C22 1.383(3) . ?
C21 C26 1.388(3) . ?
C22 C23 1.396(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(3) . ?
C24 C25 1.372(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21A N22A 1.22(2) . ?
C21A C26A 1.38(4) . ?
N22A C23A 1.42(3) . ?
C23A C24A 1.58(3) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.05(3) . ?
C25A C26A 1.44(4) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
C21B N22B 1.29(3) . ?
C21B C26B 1.50(3) . ?
N22B C23B 1.26(3) . ?
C23B C24B 1.69(3) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.13(4) . ?
C25B C26B 1.34(3) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?
Cl1A C1A 1.842(15) . ?
C1A Cl2A 1.75(2) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
Cl1B C2B 1.69(2) . ?
C2B Cl2B 1.734(19) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?

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
O1 C1 N1 119.6(2) . . ?
O1 C1 C13 122.9(2) . . ?
N1 C1 C13 117.31(18) . . ?
C2 N1 C11B 126.1(8) . . ?
C2 N1 C1 118.37(18) . . ?
C11B N1 C1 112.6(8) . . ?
C2 N1 C11A 119.8(7) . . ?
C1 N1 C11A 117.8(7) . . ?
O2 C2 N1 120.2(2) . . ?
O2 C2 C21 120.8(2) . . ?
N1 C2 C21 118.92(18) . . ?
O3 C3 N2 119.7(2) . . ?
O3 C3 C23 122.5(2) . . ?
N2 C3 C23 117.71(18) . . ?
C4 N2 C21B 117.9(10) . . ?
C4 N2 C3 116.4(2) . . ?
C21B N2 C3 120.1(9) . . ?
C4 N2 C21A 125.1(9) . . ?
C3 N2 C21A 114.5(7) . . ?
O4 C4 N2 119.4(2) . . ?
O4 C4 C11 122.1(2) . 2_655 ?
N2 C4 C11 118.43(19) . 2_655 ?
C12 C11 C16 119.3(2) . . ?
C12 C11 C4 121.67(19) . 2_655 ?
C16 C11 C4 118.7(2) . 2_655 ?
C13 C12 C11 120.38(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 C1 121.44(18) . . ?
C14 C13 C1 118.7(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N12A C11A C16A 126.7(11) . . ?
N12A C11A N1 112.3(11) . . ?
C16A C11A N1 120.9(10) . . ?
C11A N12A C13A 112.8(12) . . ?
N12A C13A C14A 126.7(14) . . ?
N12A C13A H13A 116.6 . . ?
C14A C13A H13A 116.6 . . ?
C13A C14A C15A 118.8(12) . . ?
C13A C14A Cl14 120.3(10) . . ?
C15A C14A Cl14 118.7(10) . . ?
C14A C15A C16A 115.6(14) . . ?
C14A C15A H15A 122.2 . . ?
C16A C15A H15A 122.2 . . ?
C11A C16A C15A 118.5(15) . . ?
C11A C16A H16A 120.7 . . ?
C15A C16A H16A 120.7 . . ?
N12B C11B C16B 123.4(12) . . ?
N12B C11B N1 114.4(13) . . ?
C16B C11B N1 122.1(13) . . ?
C11B N12B C13B 113.6(12) . . ?
N12B C13B C14B 128.0(14) . . ?
N12B C13B H13B 116.0 . . ?
C14B C13B H13B 116.0 . . ?
C15B C14B C13B 116.5(13) . . ?
C15B C14B Cl14 120.5(12) . . ?
C13B C14B Cl14 120.1(12) . . ?
C14B C15B C16B 116.0(16) . . ?
C14B C15B H15B 122.0 . . ?
C16B C15B H15B 122.0 . . ?
C11B C16B C15B 120.8(17) . . ?
C11B C16B H16B 119.6 . . ?
C15B C16B H16B 119.6 . . ?
C22 C21 C26 119.73(19) . . ?
C22 C21 C2 122.6(2) . . ?
C26 C21 C2 117.2(2) . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 119.4(2) . . ?
C24 C23 C3 117.71(19) . . ?
C22 C23 C3 122.60(19) . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
N22A C21A C26A 125.0(15) . . ?
N22A C21A N2 119.6(15) . . ?
C26A C21A N2 115.4(19) . . ?
C21A N22A C23A 120.2(15) . . ?
N22A C23A C24A 111.9(17) . . ?
N22A C23A H23A 124.1 . . ?
C24A C23A H23A 124.1 . . ?
C25A C24A C23A 120.3(17) . . ?
C25A C24A Cl24 130.3(17) . . ?
C23A C24A Cl24 108.3(10) . . ?
C24A C25A C26A 127(2) . . ?
C24A C25A H25A 116.7 . . ?
C26A C25A H25A 116.7 . . ?
C21A C26A C25A 114(2) . . ?
C21A C26A H26A 122.9 . . ?
C25A C26A H26A 122.9 . . ?
N22B C21B N2 125(2) . . ?
N22B C21B C26B 122.0(14) . . ?
N2 C21B C26B 113.2(16) . . ?
C23B N22B C21B 122(2) . . ?
N22B C23B C24B 116(2) . . ?
N22B C23B H23B 122.1 . . ?
C24B C23B H23B 122.1 . . ?
C25B C24B C23B 117.0(18) . . ?
C25B C24B Cl24 131.7(17) . . ?
C23B C24B Cl24 110.5(11) . . ?
C24B C25B C26B 127(2) . . ?
C24B C25B H25B 116.3 . . ?
C26B C25B H25B 116.3 . . ?
C25B C26B C21B 115.4(15) . . ?
C25B C26B H26B 122.3 . . ?
C21B C26B H26B 122.3 . . ?
Cl2A C1A Cl1A 99.3(9) . . ?
Cl2A C1A H1A1 111.9 . . ?
Cl1A C1A H1A1 111.9 . . ?
Cl2A C1A H1A2 111.9 . . ?
Cl1A C1A H1A2 111.9 . . ?
H1A1 C1A H1A2 109.6 . . ?
Cl1B C2B H2B1 115.0 . . ?
Cl2B C2B H2B1 115.0 . . ?
Cl1B C2B H2B2 115.0 . . ?
Cl2B C2B H2B2 115.0 . . ?
H2B1 C2B H2B2 112.1 . . ?

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
O1 C1 N1 C2 129.2(3) . . . . ?
C13 C1 N1 C2 -56.2(3) . . . . ?
O1 C1 N1 C11B -32.4(9) . . . . ?
C13 C1 N1 C11B 142.2(9) . . . . ?
O1 C1 N1 C11A -28.0(8) . . . . ?
C13 C1 N1 C11A 146.6(7) . . . . ?
C11B N1 C2 O2 151.7(10) . . . . ?
C1 N1 C2 O2 -7.1(3) . . . . ?
C11A N1 C2 O2 149.6(7) . . . . ?
C11B N1 C2 C21 -31.0(10) . . . . ?
C1 N1 C2 C21 170.2(2) . . . . ?
C11A N1 C2 C21 -33.1(8) . . . . ?
O3 C3 N2 C4 -122.4(3) . . . . ?
C23 C3 N2 C4 60.6(3) . . . . ?
O3 C3 N2 C21B 30.6(11) . . . . ?
C23 C3 N2 C21B -146.4(11) . . . . ?
O3 C3 N2 C21A 36.0(8) . . . . ?
C23 C3 N2 C21A -140.9(8) . . . . ?
C21B N2 C4 O4 -144.2(10) . . . . ?
C3 N2 C4 O4 9.4(3) . . . . ?
C21A N2 C4 O4 -146.5(8) . . . . ?
C21B N2 C4 C11 39.3(10) . . . 2_655 ?
C3 N2 C4 C11 -167.12(18) . . . 2_655 ?
C21A N2 C4 C11 37.0(8) . . . 2_655 ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C4 C11 C12 C13 173.1(2) 2_655 . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C11 C12 C13 C1 -171.2(2) . . . . ?
O1 C1 C13 C12 150.7(3) . . . . ?
N1 C1 C13 C12 -23.7(4) . . . . ?
O1 C1 C13 C14 -22.4(4) . . . . ?
N1 C1 C13 C14 163.2(2) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C1 C13 C14 C15 172.6(2) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C14 C15 C16 C11 2.3(4) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
C4 C11 C16 C15 -175.4(2) 2_655 . . . ?
C2 N1 C11A N12A 142.1(9) . . . . ?
C11B N1 C11A N12A -23(12) . . . . ?
C1 N1 C11A N12A -61.0(12) . . . . ?
C2 N1 C11A C16A -40.4(14) . . . . ?
C11B N1 C11A C16A 155(13) . . . . ?
C1 N1 C11A C16A 116.5(13) . . . . ?
C16A C11A N12A C13A -1.4(16) . . . . ?
N1 C11A N12A C13A 175.9(14) . . . . ?
C11A N12A C13A C14A -3(2) . . . . ?
N12A C13A C14A C15A 10(3) . . . . ?
N12A C13A C14A Cl14 173.3(15) . . . . ?
C14B Cl14 C14A C13A -44(6) . . . . ?
C14B Cl14 C14A C15A 119(7) . . . . ?
C13A C14A C15A C16A -11(2) . . . . ?
Cl14 C14A C15A C16A -174.5(14) . . . . ?
N12A C11A C16A C15A -1(2) . . . . ?
N1 C11A C16A C15A -177.7(17) . . . . ?
C14A C15A C16A C11A 7(2) . . . . ?
C2 N1 C11B N12B -40.6(15) . . . . ?
C1 N1 C11B N12B 119.3(11) . . . . ?
C11A N1 C11B N12B -24(12) . . . . ?
C2 N1 C11B C16B 138.6(13) . . . . ?
C1 N1 C11B C16B -61.5(17) . . . . ?
C11A N1 C11B C16B 155(13) . . . . ?
C16B C11B N12B C13B -0.9(17) . . . . ?
N1 C11B N12B C13B 178.3(16) . . . . ?
C11B N12B C13B C14B -7.0(19) . . . . ?
N12B C13B C14B C15B 15(3) . . . . ?
N12B C13B C14B Cl14 175.3(14) . . . . ?
C14A Cl14 C14B C15B 118(7) . . . . ?
C14A Cl14 C14B C13B -41(5) . . . . ?
C13B C14B C15B C16B -14(2) . . . . ?
Cl14 C14B C15B C16B -174.1(13) . . . . ?
N12B C11B C16B C15B 0(2) . . . . ?
N1 C11B C16B C15B -178.8(17) . . . . ?
C14B C15B C16B C11B 7.4(19) . . . . ?
O2 C2 C21 C22 137.6(2) . . . . ?
N1 C2 C21 C22 -39.7(3) . . . . ?
O2 C2 C21 C26 -34.8(3) . . . . ?
N1 C2 C21 C26 147.9(2) . . . . ?
C26 C21 C22 C23 1.7(3) . . . . ?
C2 C21 C22 C23 -170.58(19) . . . . ?
C21 C22 C23 C24 -1.8(3) . . . . ?
C21 C22 C23 C3 172.2(2) . . . . ?
O3 C3 C23 C24 20.2(4) . . . . ?
N2 C3 C23 C24 -162.89(19) . . . . ?
O3 C3 C23 C22 -153.9(2) . . . . ?
N2 C3 C23 C22 23.0(3) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C3 C23 C24 C25 -174.6(2) . . . . ?
C23 C24 C25 C26 2.4(4) . . . . ?
C24 C25 C26 C21 -2.5(4) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C2 C21 C26 C25 173.1(2) . . . . ?
C4 N2 C21A N22A -146.8(12) . . . . ?
C21B N2 C21A N22A -163(12) . . . . ?
C3 N2 C21A N22A 56.9(16) . . . . ?
C4 N2 C21A C26A 36.1(17) . . . . ?
C21B N2 C21A C26A 20(10) . . . . ?
C3 N2 C21A C26A -120.2(14) . . . . ?
C26A C21A N22A C23A -1(3) . . . . ?
N2 C21A N22A C23A -177.8(14) . . . . ?
C21A N22A C23A C24A -10(2) . . . . ?
N22A C23A C24A C25A 15(3) . . . . ?
N22A C23A C24A Cl24 -176.0(15) . . . . ?
C24B Cl24 C24A C25A 163(9) . . . . ?
C24B Cl24 C24A C23A -5(6) . . . . ?
C23A C24A C25A C26A -8(4) . . . . ?
Cl24 C24A C25A C26A -174(2) . . . . ?
N22A C21A C26A C25A 9(3) . . . . ?
N2 C21A C26A C25A -173.8(16) . . . . ?
C24A C25A C26A C21A -4(4) . . . . ?
C4 N2 C21B N22B 22(2) . . . . ?
C3 N2 C21B N22B -130.6(17) . . . . ?
C21A N2 C21B N22B -173(12) . . . . ?
C4 N2 C21B C26B -154.0(10) . . . . ?
C3 N2 C21B C26B 53.4(15) . . . . ?
C21A N2 C21B C26B 11(10) . . . . ?
N2 C21B N22B C23B 178.7(17) . . . . ?
C26B C21B N22B C23B -6(3) . . . . ?
C21B N22B C23B C24B 3(3) . . . . ?
N22B C23B C24B C25B 6(3) . . . . ?
N22B C23B C24B Cl24 176.8(17) . . . . ?
C24A Cl24 C24B C25B 167(9) . . . . ?
C24A Cl24 C24B C23B -3(6) . . . . ?
C23B C24B C25B C26B -11(4) . . . . ?
Cl24 C24B C25B C26B -180(2) . . . . ?
C24B C25B C26B C21B 8(3) . . . . ?
N22B C21B C26B C25B 1(3) . . . . ?
N2 C21B C26B C25B 177.6(15) . . . . ?


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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
C13B H13B O4 0.93 2.48 3.365(15) 158 5_755 yes
C12 H12 N1 0.93 2.58 2.902(3) 101 . yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MIO4_CH2Cl2
_audit_block_doi                 10.5517/cc14n420
_database_code_depnum_ccdc_archive 'CCDC 1062031'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            MIO4:CH2Cl2
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H40 N8 O8, C H2 Cl2'
_chemical_formula_sum            'C57 H42 Cl2 N8 O8'
_chemical_formula_weight         1037.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'

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

_cell_length_a                   13.9556(3)
_cell_length_b                   19.0850(4)
_cell_length_c                   19.1230(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5093.27(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6192
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      63.46

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2152
_exptl_absorpt_coefficient_mu    1.684
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.7627
_exptl_absorpt_correction_T_max  0.9057
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         32023
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_reflns_number            30192
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         63.57
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        62.50
_diffrn_measured_fraction_theta_full 1.000
_reflns_number_total             4140
_reflns_number_gt                3245
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.0317P)²+6.873P] where P=(Fo²+2Fc²)/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       0.00078(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4140
_refine_ls_number_parameters     473
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.041

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9665(3) 0.30799(15) -0.10225(14) 0.1033(12) Uani 1 1 d . . .
C1 C 0.9478(3) 0.31674(18) -0.04184(18) 0.0593(9) Uani 1 1 d . A .
N1 N 0.9558(2) 0.25974(15) 0.00630(13) 0.0491(7) Uani 1 1 d . . .
O2 O 1.0548(2) 0.32300(14) 0.07560(15) 0.0755(8) Uani 1 1 d . . .
C2 C 1.0090(2) 0.26980(17) 0.06718(18) 0.0522(8) Uani 1 1 d . A .
O3 O 0.8235(2) 0.08506(19) 0.28573(14) 0.0941(11) Uani 1 1 d . . .
C3 C 0.8328(3) 0.10265(19) 0.22581(18) 0.0581(9) Uani 1 1 d . A .
N2 N 0.7542(2) 0.09522(14) 0.17792(14) 0.0513(7) Uani 1 1 d . . .
O4 O 0.8440(2) 0.01917(14) 0.11517(15) 0.0788(8) Uani 1 1 d . . .
C4 C 0.7709(3) 0.05333(17) 0.11926(18) 0.0552(9) Uani 1 1 d . . .
C11 C 0.8008(2) 0.44529(16) 0.06166(16) 0.0486(8) Uani 1 1 d . . .
C12 C 0.8479(2) 0.38411(16) 0.04328(16) 0.0464(8) Uani 1 1 d . A .
H12 H 0.8397 0.3437 0.0698 0.056 Uiso 1 1 calc R . .
C13 C 0.9075(3) 0.38325(17) -0.01503(16) 0.0507(8) Uani 1 1 d . . .
C14 C 0.9212(3) 0.44403(18) -0.05323(19) 0.0614(10) Uani 1 1 d . A .
H14 H 0.9609 0.4435 -0.0922 0.074 Uiso 1 1 calc R . .
C15 C 0.8762(3) 0.50512(19) -0.0338(2) 0.0685(11) Uani 1 1 d . . .
H15 H 0.8871 0.5462 -0.0588 0.082 Uiso 1 1 calc R A .
C16 C 0.8152(3) 0.50540(18) 0.02260(19) 0.0621(10) Uani 1 1 d . A .
H16 H 0.7833 0.5464 0.0346 0.075 Uiso 1 1 calc R . .
C11A C 0.9397(15) 0.1887(11) -0.0254(13) 0.055(8) Uani 0.50 1 d PD A -1
N12A N 0.8517(13) 0.1782(11) -0.0489(10) 0.071(7) Uani 0.50 1 d PD A -1
C13A C 0.840(2) 0.1154(11) -0.0769(12) 0.093(9) Uani 0.50 1 d PD A -1
H13A H 0.7796 0.1058 -0.0943 0.112 Uiso 0.50 1 calc PR A -1
C14A C 0.9057(19) 0.0628(11) -0.084(2) 0.058(8) Uani 0.50 1 d PDU A -1
C15A C 0.9958(16) 0.0791(10) -0.0595(12) 0.056(5) Uani 0.50 1 d PD A -1
H15A H 1.0442 0.0459 -0.0635 0.067 Uiso 0.50 1 calc PR A -1
C16A C 1.0172(16) 0.1436(12) -0.0292(14) 0.062(7) Uani 0.50 1 d PD A -1
H16A H 1.0780 0.1553 -0.0130 0.074 Uiso 0.50 1 calc PR A -1
C17 C 0.8816(4) -0.0057(2) -0.1118(2) 0.0885(14) Uani 1 1 d D A -1
H17A H 0.8183 -0.0043 -0.1315 0.133 Uiso 1 1 calc R A -1
H17B H 0.8836 -0.0400 -0.0751 0.133 Uiso 1 1 calc R A -1
H17C H 0.9268 -0.0181 -0.1475 0.133 Uiso 1 1 calc R A -1
C11B C 0.9372(11) 0.1943(10) -0.0202(11) 0.042(6) Uani 0.50 1 d PD A -2
N12B N 1.0022(11) 0.1444(8) -0.0182(10) 0.046(4) Uani 0.50 1 d PD A -2
C13B C 0.9827(14) 0.0816(10) -0.0431(11) 0.055(5) Uani 0.50 1 d PD A -2
H13B H 1.0283 0.0465 -0.0375 0.066 Uiso 0.50 1 calc PR A -2
C14B C 0.8989(17) 0.0650(10) -0.077(2) 0.051(6) Uani 0.50 1 d PDU A -2
C15B C 0.8285(15) 0.1157(5) -0.0793(7) 0.036(3) Uani 0.50 1 d PD A -2
H15B H 0.7700 0.1067 -0.1007 0.044 Uiso 0.50 1 calc PR A -2
C16B C 0.8471(13) 0.1811(8) -0.0487(8) 0.038(5) Uani 0.50 1 d PD A -2
H16B H 0.7997 0.2153 -0.0474 0.046 Uiso 0.50 1 calc PR A -2
C21 C 1.0060(2) 0.21479(17) 0.12270(17) 0.0484(8) Uani 1 1 d . . .
C22 C 0.9229(2) 0.17913(16) 0.14047(16) 0.0464(8) Uani 1 1 d . A .
H22 H 0.8681 0.1839 0.1132 0.056 Uiso 1 1 calc R . .
C23 C 0.9216(2) 0.13606(17) 0.19934(16) 0.0494(8) Uani 1 1 d . . .
C24 C 1.0048(3) 0.12802(19) 0.23870(18) 0.0571(9) Uani 1 1 d . A .
H24 H 1.0041 0.0998 0.2783 0.068 Uiso 1 1 calc R . .
C25 C 1.0882(3) 0.1616(2) 0.21945(19) 0.0634(10) Uani 1 1 d . . .
H25 H 1.1441 0.1545 0.2449 0.076 Uiso 1 1 calc R A .
C26 C 1.0885(3) 0.20536(19) 0.16275(19) 0.0583(9) Uani 1 1 d . A .
H26 H 1.1443 0.2291 0.1508 0.070 Uiso 1 1 calc R . .
C21A C 0.648(3) 0.1085(19) 0.2103(15) 0.059(8) Uani 0.50 1 d PD B -1
N22A N 0.637(2) 0.1695(11) 0.2426(13) 0.106(8) Uani 0.50 1 d PD B -1
C23A C 0.560(3) 0.1775(12) 0.2648(13) 0.053(6) Uani 0.50 1 d PD B -1
H23A H 0.5478 0.2189 0.2890 0.064 Uiso 0.50 1 calc PR B -1
C24A C 0.4709(18) 0.123(2) 0.2571(10) 0.052(5) Uani 0.50 1 d PD B -1
C25A C 0.502(2) 0.065(2) 0.2256(17) 0.078(9) Uani 0.50 1 d PD B -1
H25A H 0.4603 0.0280 0.2181 0.094 Uiso 0.50 1 calc PR B -1
C26A C 0.594(3) 0.0612(18) 0.2047(15) 0.054(6) Uani 0.50 1 d PD B -1
H26A H 0.6156 0.0195 0.1850 0.064 Uiso 0.50 1 calc PR B -1
C27A C 0.3657(16) 0.1309(16) 0.2751(16) 0.096(7) Uani 0.50 1 d PD B -1
H27A H 0.3275 0.1132 0.2373 0.144 Uiso 0.50 1 calc PR B -1
H27B H 0.3511 0.1795 0.2825 0.144 Uiso 0.50 1 calc PR B -1
H27C H 0.3518 0.1049 0.3169 0.144 Uiso 0.50 1 calc PR B -1
C21B C 0.668(2) 0.1032(10) 0.2022(11) 0.028(4) Uani 0.50 1 d PD B -2
N22B N 0.597(2) 0.0491(13) 0.1916(11) 0.042(4) Uani 0.50 1 d PD B -2
C23B C 0.512(2) 0.0655(16) 0.2168(15) 0.068(8) Uani 0.50 1 d PD B -2
H23B H 0.4636 0.0331 0.2103 0.082 Uiso 0.50 1 calc PR B -2
C24B C 0.489(2) 0.127(3) 0.2526(16) 0.085(10) Uani 0.50 1 d PD B -2
C25B C 0.535(3) 0.1733(18) 0.2663(17) 0.079(11) Uani 0.50 1 d PD B -2
H25B H 0.5134 0.2117 0.2918 0.094 Uiso 0.50 1 calc PR B -2
C26B C 0.6423(10) 0.1656(8) 0.2368(10) 0.039(4) Uani 0.50 1 d PD B -2
H26B H 0.6865 0.2016 0.2426 0.047 Uiso 0.50 1 calc PR B -2
C27B C 0.3936(18) 0.1422(18) 0.2876(17) 0.122(11) Uani 0.50 1 d PD B -2
H27D H 0.4025 0.1758 0.3243 0.183 Uiso 0.50 1 calc PR B -2
H27E H 0.3684 0.0995 0.3069 0.183 Uiso 0.50 1 calc PR B -2
H27F H 0.3494 0.1605 0.2537 0.183 Uiso 0.50 1 calc PR B -2
Cl1S Cl 0.1914(3) 0.3094(2) -0.0986(2) 0.1405(13) Uani 0.50 1 d PD C -1
C1S C 0.2851(10) 0.2616(14) -0.0699(14) 0.311(16) Uani 0.50 1 d PD C -1
H1S1 H 0.3353 0.2933 -0.0549 0.373 Uiso 0.50 1 calc PR C -1
H1S2 H 0.3101 0.2345 -0.1088 0.373 Uiso 0.50 1 calc PR C -1
Cl2S Cl 0.2595(4) 0.2056(2) -0.0027(3) 0.191(2) Uani 0.50 1 d PD C -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.196(4) . ?
C1 N1 1.429(4) . ?
C1 C13 1.480(5) . ?
N1 C11B 1.37(2) . ?
N1 C2 1.394(4) . ?
N1 C11A 1.50(2) . ?
O2 C2 1.211(4) . ?
C2 C21 1.494(4) . ?
O3 C3 1.201(4) . ?
C3 N2 1.436(4) . ?
C3 C23 1.483(5) . ?
N2 C21B 1.30(3) . ?
N2 C4 1.397(4) . ?
N2 C21A 1.62(4) . ?
O4 C4 1.213(4) . ?
C4 C11 1.488(5) 2_655 ?
C11 C16 1.384(5) . ?
C11 C12 1.385(4) . ?
C11 C4 1.488(5) 2_655 ?
C12 C13 1.391(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C14 C15 1.375(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11A N12A 1.322(13) . ?
C11A C16A 1.384(13) . ?
N12A C13A 1.323(13) . ?
C13A C14A 1.361(13) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.374(13) . ?
C14A C17 1.454(14) . ?
C15A C16A 1.392(12) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C11B N12B 1.316(11) . ?
C11B C16B 1.393(12) . ?
N12B C13B 1.319(12) . ?
C13B C14B 1.374(12) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.378(13) . ?
C15B C16B 1.402(10) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21 C22 1.387(4) . ?
C21 C26 1.394(5) . ?
C22 C23 1.394(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(5) . ?
C24 C25 1.378(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21A C26A 1.19(6) . ?
C21A N22A 1.33(4) . ?
N22A C23A 1.17(5) . ?
C23A C24A 1.62(6) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.33(4) . ?
C24A C27A 1.515(17) . ?
C25A C26A 1.35(5) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
C27A H27A 0.9600 . ?
C27A H27B 0.9600 . ?
C27A H27C 0.9600 . ?
C21B C26B 1.41(3) . ?
C21B N22B 1.44(4) . ?
N22B C23B 1.32(5) . ?
C23B C24B 1.40(5) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.12(6) . ?
C24B C27B 1.515(17) . ?
C25B C26B 1.61(5) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?
C27B H27D 0.9600 . ?
C27B H27E 0.9600 . ?
C27B H27F 0.9600 . ?
Cl1S C1S 1.687(17) . ?
C1S Cl2S 1.709(15) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?

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
O1 C1 N1 119.9(3) . . ?
O1 C1 C13 122.5(3) . . ?
N1 C1 C13 117.3(3) . . ?
C11B N1 C2 122.3(7) . . ?
C11B N1 C1 116.1(8) . . ?
C2 N1 C1 118.3(3) . . ?
C2 N1 C11A 122.7(9) . . ?
C1 N1 C11A 114.6(9) . . ?
O2 C2 N1 120.5(3) . . ?
O2 C2 C21 120.6(3) . . ?
N1 C2 C21 118.8(3) . . ?
O3 C3 N2 119.9(3) . . ?
O3 C3 C23 122.4(3) . . ?
N2 C3 C23 117.6(3) . . ?
C21B N2 C4 120.6(9) . . ?
C21B N2 C3 117.9(9) . . ?
C4 N2 C3 116.2(3) . . ?
C4 N2 C21A 123.2(13) . . ?
C3 N2 C21A 115.9(11) . . ?
O4 C4 N2 119.9(3) . . ?
O4 C4 C11 121.8(3) . 2_655 ?
N2 C4 C11 118.2(3) . 2_655 ?
C16 C11 C12 119.5(3) . . ?
C16 C11 C4 118.9(3) . 2_655 ?
C12 C11 C4 121.4(3) . 2_655 ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 C1 118.9(3) . . ?
C12 C13 C1 121.0(3) . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.7(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N12A C11A C16A 128(2) . . ?
N12A C11A N1 114.3(18) . . ?
C16A C11A N1 117.8(15) . . ?
C11A N12A C13A 113(2) . . ?
N12A C13A C14A 129(2) . . ?
N12A C13A H13A 115.6 . . ?
C14A C13A H13A 115.6 . . ?
C13A C14A C15A 114.4(17) . . ?
C13A C14A C17 122.8(18) . . ?
C15A C14A C17 122.7(17) . . ?
C14A C15A C16A 122.4(14) . . ?
C14A C15A H15A 118.8 . . ?
C16A C15A H15A 118.8 . . ?
C11A C16A C15A 113.8(16) . . ?
C11A C16A H16A 123.1 . . ?
C15A C16A H16A 123.1 . . ?
N12B C11B N1 121.2(12) . . ?
N12B C11B C16B 120.1(17) . . ?
N1 C11B C16B 118.7(13) . . ?
C11B N12B C13B 120.3(13) . . ?
N12B C13B C14B 123.7(14) . . ?
N12B C13B H13B 118.2 . . ?
C14B C13B H13B 118.2 . . ?
C13B C14B C15B 117.5(13) . . ?
C14B C15B C16B 118.6(18) . . ?
C14B C15B H15B 120.7 . . ?
C16B C15B H15B 120.7 . . ?
C11B C16B C15B 119.5(18) . . ?
C11B C16B H16B 120.3 . . ?
C15B C16B H16B 120.3 . . ?
C22 C21 C26 119.5(3) . . ?
C22 C21 C2 122.9(3) . . ?
C26 C21 C2 117.3(3) . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 C3 117.7(3) . . ?
C22 C23 C3 122.7(3) . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 120.8(3) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C26A C21A N22A 129(4) . . ?
C26A C21A N2 116(3) . . ?
N22A C21A N2 115(3) . . ?
C23A N22A C21A 113(3) . . ?
N22A C23A C24A 126.1(19) . . ?
N22A C23A H23A 117.0 . . ?
C24A C23A H23A 117.0 . . ?
C25A C24A C27A 120(3) . . ?
C25A C24A C23A 109(2) . . ?
C27A C24A C23A 131(3) . . ?
C24A C25A C26A 120(3) . . ?
C24A C25A H25A 120.2 . . ?
C26A C25A H25A 120.2 . . ?
C21A C26A C25A 123(4) . . ?
C21A C26A H26A 118.7 . . ?
C25A C26A H26A 118.7 . . ?
N2 C21B C26B 120.3(19) . . ?
N2 C21B N22B 120(2) . . ?
C26B C21B N22B 120(3) . . ?
C23B N22B C21B 113(2) . . ?
N22B C23B C24B 126(3) . . ?
N22B C23B H23B 116.9 . . ?
C24B C23B H23B 116.9 . . ?
C25B C24B C23B 130(3) . . ?
C25B C24B C27B 105(4) . . ?
C23B C24B C27B 125(4) . . ?
C24B C25B C26B 112(3) . . ?
C24B C25B H25B 123.8 . . ?
C26B C25B H25B 123.8 . . ?
C21B C26B C25B 118.7(19) . . ?
C21B C26B H26B 120.7 . . ?
C25B C26B H26B 120.7 . . ?
C24B C27B H27D 109.5 . . ?
C24B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C24B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
Cl1S C1S Cl2S 114.9(10) . . ?
Cl1S C1S H1S1 108.5 . . ?
Cl2S C1S H1S1 108.5 . . ?
Cl1S C1S H1S2 108.5 . . ?
Cl2S C1S H1S2 108.5 . . ?
H1S1 C1S H1S2 107.5 . . ?

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
O1 C1 N1 C11B -31.7(10) . . . . ?
C13 C1 N1 C11B 142.7(9) . . . . ?
O1 C1 N1 C2 128.3(4) . . . . ?
C13 C1 N1 C2 -57.3(4) . . . . ?
O1 C1 N1 C11A -28.8(11) . . . . ?
C13 C1 N1 C11A 145.5(10) . . . . ?
C11B N1 C2 O2 151.6(10) . . . . ?
C1 N1 C2 O2 -7.1(5) . . . . ?
C11A N1 C2 O2 148.0(11) . . . . ?
C11B N1 C2 C21 -30.3(11) . . . . ?
C1 N1 C2 C21 171.0(3) . . . . ?
C11A N1 C2 C21 -33.8(11) . . . . ?
O3 C3 N2 C21B 33.1(11) . . . . ?
C23 C3 N2 C21B -143.4(10) . . . . ?
O3 C3 N2 C4 -121.3(4) . . . . ?
C23 C3 N2 C4 62.2(4) . . . . ?
O3 C3 N2 C21A 35.3(15) . . . . ?
C23 C3 N2 C21A -141.3(14) . . . . ?
C21B N2 C4 O4 -145.1(10) . . . . ?
C3 N2 C4 O4 8.6(5) . . . . ?
C21A N2 C4 O4 -146.0(13) . . . . ?
C21B N2 C4 C11 37.7(10) . . . 2_655 ?
C3 N2 C4 C11 -168.6(3) . . . 2_655 ?
C21A N2 C4 C11 36.7(13) . . . 2_655 ?
C16 C11 C12 C13 -1.4(5) . . . . ?
C4 C11 C12 C13 173.9(3) 2_655 . . . ?
C11 C12 C13 C14 1.6(5) . . . . ?
C11 C12 C13 C1 -171.3(3) . . . . ?
O1 C1 C13 C14 -22.4(6) . . . . ?
N1 C1 C13 C14 163.4(3) . . . . ?
O1 C1 C13 C12 150.5(4) . . . . ?
N1 C1 C13 C12 -23.6(5) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C1 C13 C14 C15 173.1(4) . . . . ?
C13 C14 C15 C16 -1.9(6) . . . . ?
C14 C15 C16 C11 2.1(6) . . . . ?
C12 C11 C16 C15 -0.5(5) . . . . ?
C4 C11 C16 C15 -175.9(3) 2_655 . . . ?
C2 N1 C11A N12A 138.8(13) . . . . ?
C1 N1 C11A N12A -65.3(19) . . . . ?
C2 N1 C11A C16A -44(2) . . . . ?
C1 N1 C11A C16A 112.4(18) . . . . ?
C16A C11A N12A C13A 2(3) . . . . ?
N1 C11A N12A C13A 180(2) . . . . ?
C11A N12A C13A C14A 0(4) . . . . ?
N12A C13A C14A C15A -2(5) . . . . ?
N12A C13A C14A C17 176(3) . . . . ?
C13A C14A C15A C16A 2(5) . . . . ?
C17 C14A C15A C16A -177(3) . . . . ?
N12A C11A C16A C15A -3(3) . . . . ?
N1 C11A C16A C15A -180(2) . . . . ?
C14A C15A C16A C11A 0(4) . . . . ?
C2 N1 C11B N12B -38(2) . . . . ?
C1 N1 C11B N12B 120.9(15) . . . . ?
C11A N1 C11B N12B 61(27) . . . . ?
C2 N1 C11B C16B 140.9(12) . . . . ?
C1 N1 C11B C16B -59.9(18) . . . . ?
C11A N1 C11B C16B -120(29) . . . . ?
N1 C11B N12B C13B 179(2) . . . . ?
C16B C11B N12B C13B 0(2) . . . . ?
C11B N12B C13B C14B 5(3) . . . . ?
N12B C13B C14B C15B -6(5) . . . . ?
C13B C14B C15B C16B 1(4) . . . . ?
N12B C11B C16B C15B -4(2) . . . . ?
N1 C11B C16B C15B 176.7(16) . . . . ?
C14B C15B C16B C11B 3(3) . . . . ?
O2 C2 C21 C22 138.9(4) . . . . ?
N1 C2 C21 C22 -39.3(5) . . . . ?
O2 C2 C21 C26 -34.0(5) . . . . ?
N1 C2 C21 C26 147.9(3) . . . . ?
C26 C21 C22 C23 2.1(5) . . . . ?
C2 C21 C22 C23 -170.6(3) . . . . ?
C21 C22 C23 C24 -1.6(5) . . . . ?
C21 C22 C23 C3 173.1(3) . . . . ?
O3 C3 C23 C24 19.2(6) . . . . ?
N2 C3 C23 C24 -164.4(3) . . . . ?
O3 C3 C23 C22 -155.6(4) . . . . ?
N2 C3 C23 C22 20.9(5) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C3 C23 C24 C25 -175.7(3) . . . . ?
C23 C24 C25 C26 2.6(6) . . . . ?
C24 C25 C26 C21 -2.1(6) . . . . ?
C22 C21 C26 C25 -0.2(5) . . . . ?
C2 C21 C26 C25 172.8(3) . . . . ?
C4 N2 C21A C26A 32(3) . . . . ?
C3 N2 C21A C26A -122(2) . . . . ?
C4 N2 C21A N22A -151.1(14) . . . . ?
C3 N2 C21A N22A 54(2) . . . . ?
C26A C21A N22A C23A -5(4) . . . . ?
N2 C21A N22A C23A 179(2) . . . . ?
C21A N22A C23A C24A -2(3) . . . . ?
N22A C23A C24A C25A 4(4) . . . . ?
N22A C23A C24A C27A -171(3) . . . . ?
C27A C24A C25A C26A 175(3) . . . . ?
C23A C24A C25A C26A -2(3) . . . . ?
N22A C21A C26A C25A 8(4) . . . . ?
N2 C21A C26A C25A -176(2) . . . . ?
C24A C25A C26A C21A -3(4) . . . . ?
C4 N2 C21B C26B -150.5(12) . . . . ?
C3 N2 C21B C26B 56.2(17) . . . . ?
C4 N2 C21B N22B 27.4(19) . . . . ?
C3 N2 C21B N22B -125.9(14) . . . . ?
N2 C21B N22B C23B -177.7(19) . . . . ?
C26B C21B N22B C23B 0(2) . . . . ?
C21B N22B C23B C24B -2(3) . . . . ?
N22B C23B C24B C25B 0(6) . . . . ?
N22B C23B C24B C27B -173(3) . . . . ?
C23B C24B C25B C26B 2(5) . . . . ?
C27B C24B C25B C26B 177(2) . . . . ?
N2 C21B C26B C25B -179.9(18) . . . . ?
N22B C21B C26B C25B 2(2) . . . . ?
C24B C25B C26B C21B -4(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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
C12 H12 N1 0.93 2.58 2.898(4) 100 . yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MIO4_CHCl3
_audit_block_doi                 10.5517/cc14n431
_database_code_depnum_ccdc_archive 'CCDC 1062032'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            MIO4:CHCl3
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H40 N8 O8, C H Cl3'
_chemical_formula_sum            'C57 H41 Cl3 N8 O8'
_chemical_formula_weight         1072.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'

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

_cell_length_a                   14.1849(2)
_cell_length_b                   19.0890(2)
_cell_length_c                   19.1396(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5182.54(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6232
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      63.18

_exptl_crystal_description       Orthorhombic
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2216
_exptl_absorpt_coefficient_mu    2.137
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.4745
_exptl_absorpt_correction_T_max  0.8476
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         32485
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_reflns_number            30587
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         63.36
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        60.00
_diffrn_measured_fraction_theta_full 1.000
_reflns_number_total             4220
_reflns_number_gt                3190
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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     
'w=1/[σ²(Fo²)+(0.0578P)²+1.548P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.00025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4220
_refine_ls_number_parameters     457
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.033

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17721(14) 0.41724(14) -0.28450(9) 0.0969(7) Uani 1 1 d . . .
C1 C 0.16857(18) 0.39897(13) -0.22499(12) 0.0609(6) Uani 1 1 d . . .
N1 N 0.24591(13) 0.40668(9) -0.17718(9) 0.0538(5) Uani 1 1 d . A .
O2 O 0.15811(14) 0.48255(10) -0.11436(11) 0.0822(6) Uani 1 1 d . . .
C2 C 0.23008(17) 0.44833(11) -0.11851(12) 0.0566(6) Uani 1 1 d . . .
O3 O 0.04123(18) 0.19273(10) 0.10337(9) 0.0921(7) Uani 1 1 d . . .
C3 C 0.05796(18) 0.18354(11) 0.04282(11) 0.0558(6) Uani 1 1 d . . .
N2 N 0.04924(13) 0.24047(9) -0.00565(8) 0.0484(4) Uani 1 1 d . B .
O4 O -0.04580(13) 0.17585(9) -0.07591(9) 0.0693(5) Uani 1 1 d . . .
C4 C -0.00217(16) 0.22965(11) -0.06688(11) 0.0505(5) Uani 1 1 d . . .
C11 C 0.00029(15) 0.28460(11) -0.12225(10) 0.0483(5) Uani 1 1 d . . .
C12 C 0.08145(16) 0.32155(11) -0.13997(11) 0.0496(5) Uani 1 1 d . . .
H12 H 0.1354 0.3173 -0.1127 0.059 Uiso 1 1 calc R . .
C13 C 0.08179(16) 0.36482(11) -0.19855(10) 0.0509(5) Uani 1 1 d . . .
C14 C -0.00017(18) 0.37202(13) -0.23750(12) 0.0591(6) Uani 1 1 d . . .
H14 H -0.0002 0.4006 -0.2769 0.071 Uiso 1 1 calc R . .
C15 C -0.08097(18) 0.33763(14) -0.21873(12) 0.0638(6) Uani 1 1 d . . .
H15 H -0.1361 0.3444 -0.2441 0.077 Uiso 1 1 calc R . .
C16 C -0.08062(17) 0.29309(13) -0.16230(12) 0.0581(6) Uani 1 1 d . . .
H16 H -0.1350 0.2684 -0.1508 0.070 Uiso 1 1 calc R . .
C11A C 0.33911(17) 0.39622(11) -0.20502(11) 0.0515(5) Uani 1 1 d . . .
N12A N 0.4050(8) 0.4459(6) -0.1950(4) 0.058(2) Uani 0.78 1 d P A -1
C13A C 0.4922(9) 0.4371(5) -0.2164(7) 0.062(2) Uani 0.78 1 d P A -1
H13A H 0.5363 0.4719 -0.2070 0.075 Uiso 0.78 1 calc PR A -1
C14A C 0.5218(5) 0.3760(7) -0.2537(6) 0.061(2) Uani 0.78 1 d P A -1
C15A C 0.4435(9) 0.3225(8) -0.2639(5) 0.068(3) Uani 0.78 1 d P A -1
H15A H 0.4544 0.2807 -0.2875 0.082 Uiso 0.78 1 calc PR A -1
C16A C 0.3613(13) 0.3373(9) -0.2386(9) 0.068(4) Uani 0.78 1 d P A -1
H16A H 0.3138 0.3042 -0.2444 0.081 Uiso 0.78 1 calc PR A -1
N12B N 0.346(3) 0.330(2) -0.239(2) 0.044(6) Uani 0.22 1 d PD A -2
C13B C 0.459(3) 0.338(3) -0.2668(18) 0.063(12) Uani 0.22 1 d PD A -2
H13B H 0.4842 0.3003 -0.2916 0.075 Uiso 0.22 1 calc PR A -2
C14B C 0.4925(16) 0.371(3) -0.261(2) 0.061(10) Uani 0.22 1 d PD A -2
C15B C 0.482(4) 0.426(2) -0.233(2) 0.074(11) Uani 0.22 1 d PD A -2
H15B H 0.5338 0.4562 -0.2333 0.089 Uiso 0.22 1 calc PR A -2
C16B C 0.390(4) 0.455(3) -0.197(2) 0.080(13) Uani 0.22 1 d PD A -2
H16B H 0.3760 0.4982 -0.1775 0.096 Uiso 0.22 1 calc PR A -2
C17A C 0.6154(3) 0.3644(2) -0.2799(2) 0.1277(16) Uani 1 1 d . . .
H17A H 0.6396 0.3213 -0.2613 0.192 Uiso 0.50 1 calc PR A .
H17B H 0.6555 0.4024 -0.2658 0.192 Uiso 0.50 1 calc PR . .
H17C H 0.6138 0.3619 -0.3299 0.192 Uiso 0.50 1 calc PR . .
H17D H 0.6330 0.4025 -0.3100 0.192 Uiso 0.50 1 calc PR . .
H17E H 0.6171 0.3213 -0.3056 0.192 Uiso 0.50 1 calc PR . .
H17F H 0.6588 0.3619 -0.2414 0.192 Uiso 0.50 1 calc PR . .
C21 C 0.19976(16) 0.05355(11) -0.06136(11) 0.0504(5) Uani 1 1 d . . .
C22 C 0.15462(16) 0.11497(10) -0.04235(11) 0.0478(5) Uani 1 1 d . . .
H22 H 0.1637 0.1554 -0.0687 0.057 Uiso 1 1 calc R . .
C23 C 0.09609(16) 0.11681(11) 0.01554(10) 0.0491(5) Uani 1 1 d . . .
C24 C 0.08049(18) 0.05556(12) 0.05354(12) 0.0601(6) Uani 1 1 d . . .
H24 H 0.0409 0.0563 0.0923 0.072 Uiso 1 1 calc R . .
C25 C 0.1233(2) -0.00584(12) 0.03402(14) 0.0685(7) Uani 1 1 d . . .
H25 H 0.1115 -0.0468 0.0588 0.082 Uiso 1 1 calc R . .
C26 C 0.18387(19) -0.00680(12) -0.02221(13) 0.0632(6) Uani 1 1 d . . .
H26 H 0.2145 -0.0482 -0.0342 0.076 Uiso 1 1 calc R . .
C21A C 0.06501(18) 0.30900(11) 0.02295(11) 0.0463(5) Uani 1 1 d . . .
N22A N 0.0009(12) 0.3557(16) 0.0264(13) 0.046(3) Uani 0.55 1 d P B -1
C23A C 0.0116(13) 0.4218(9) 0.0516(8) 0.061(5) Uani 0.55 1 d P B -1
H23A H -0.0369 0.4541 0.0460 0.074 Uiso 0.55 1 calc PR B -1
C24A C 0.087(2) 0.4402(15) 0.0829(16) 0.053(4) Uani 0.55 1 d P B -1
C25A C 0.1632(13) 0.3889(10) 0.0801(10) 0.071(6) Uani 0.55 1 d P B -1
H25A H 0.2215 0.4012 0.0987 0.085 Uiso 0.55 1 calc PR B -1
C26A C 0.1533(10) 0.3242(8) 0.0516(8) 0.047(4) Uani 0.55 1 d P B -1
H26A H 0.2023 0.2918 0.0511 0.056 Uiso 0.55 1 calc PR B -1
N22B N 0.1490(13) 0.3194(8) 0.0462(9) 0.061(5) Uani 0.45 1 d P B -2
C23B C 0.1678(11) 0.3836(11) 0.0760(10) 0.049(6) Uani 0.45 1 d P B -2
H23B H 0.2268 0.3910 0.0959 0.059 Uiso 0.45 1 calc PR B -2
C24B C 0.108(2) 0.4333(17) 0.077(2) 0.045(5) Uani 0.45 1 d P B -2
C25B C 0.0099(12) 0.4144(12) 0.0532(11) 0.068(7) Uani 0.45 1 d P B -2
H25B H -0.0362 0.4483 0.0606 0.082 Uiso 0.45 1 calc PR B -2
C26B C -0.0214(19) 0.351(2) 0.020(2) 0.052(4) Uani 0.45 1 d P B -2
H26B H -0.0803 0.3404 0.0021 0.062 Uiso 0.45 1 calc PR B -2
C27A C 0.1137(3) 0.50724(15) 0.11160(16) 0.0975(11) Uani 1 1 d . . .
H27A H 0.0683 0.5420 0.0982 0.146 Uiso 0.50 1 calc PR B .
H27B H 0.1747 0.5201 0.0941 0.146 Uiso 0.50 1 calc PR . .
H27C H 0.1160 0.5041 0.1616 0.146 Uiso 0.50 1 calc PR . .
H27D H 0.1710 0.5022 0.1378 0.146 Uiso 0.50 1 calc PR . .
H27E H 0.0646 0.5240 0.1418 0.146 Uiso 0.50 1 calc PR . .
H27F H 0.1233 0.5401 0.0743 0.146 Uiso 0.50 1 calc PR . .
Cl1S Cl 0.7973(5) 0.1973(3) 0.0869(4) 0.227(3) Uani 0.50 1 d P . .
Cl2S Cl 0.6840(4) 0.3125(3) 0.10489(18) 0.1308(13) Uani 0.50 1 d P . .
Cl3S Cl 0.74945(16) 0.20814(14) -0.02464(10) 0.1382(9) Uani 0.50 1 d P . .
C1S C 0.7148(5) 0.2354(5) 0.0544(4) 0.107(2) Uani 0.50 1 d PD . .
H1S H 0.669(4) 0.199(3) 0.039(4) 0.128 Uiso 0.50 1 d PD . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.197(3) . ?
C1 N1 1.436(3) . ?
C1 C13 1.482(3) . ?
N1 C2 1.394(3) . ?
N1 C11A 1.439(3) . ?
O2 C2 1.215(3) . ?
C2 C21 1.479(3) 2 ?
O3 C3 1.196(3) . ?
C3 N2 1.434(3) . ?
C3 C23 1.479(3) . ?
N2 C4 1.396(3) . ?
N2 C21A 1.436(3) . ?
O4 C4 1.211(3) . ?
C4 C11 1.491(3) . ?
C11 C16 1.390(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.393(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(3) . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11A C16A 1.333(15) . ?
C11A N12A 1.345(9) . ?
C11A C16B 1.34(4) . ?
C11A N12B 1.43(4) . ?
N12A C13A 1.315(19) . ?
C13A C14A 1.431(18) . ?
C13A H13A 0.9300 . ?
C14A C17A 1.436(9) . ?
C14A C15A 1.52(2) . ?
C15A C16A 1.29(2) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
N12B C13B 1.69(6) . ?
C13B C14B 0.79(7) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.20(7) . ?
C14B C17A 1.79(3) . ?
C15B C16B 1.57(9) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C21 C22 1.385(3) . ?
C21 C26 1.393(3) . ?
C21 C2 1.479(3) 2 ?
C22 C23 1.385(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.395(3) . ?
C24 C25 1.372(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21A N22A 1.27(3) . ?
C21A N22B 1.29(2) . ?
C21A C26A 1.397(17) . ?
C21A C26B 1.47(4) . ?
N22A C23A 1.36(3) . ?
C23A C24A 1.27(4) . ?
C23A H23A 0.9300 . ?
C24A C27A 1.44(3) . ?
C24A C25A 1.46(3) . ?
C25A C26A 1.36(3) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
N22B C23B 1.38(3) . ?
C23B C24B 1.28(4) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.51(4) . ?
C24B C27A 1.56(3) . ?
C25B C26B 1.43(5) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?
C27A H27A 0.9600 . ?
C27A H27B 0.9600 . ?
C27A H27C 0.9600 . ?
C27A H27D 0.9600 . ?
C27A H27E 0.9600 . ?
C27A H27F 0.9600 . ?
Cl1S C1S 1.511(10) . ?
Cl2S C1S 1.814(10) . ?
Cl3S C1S 1.674(8) . ?
C1S H1S 1.00(2) . ?

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
O1 C1 N1 119.9(2) . . ?
O1 C1 C13 122.5(2) . . ?
N1 C1 C13 117.51(19) . . ?
C2 N1 C1 116.7(2) . . ?
C2 N1 C11A 121.7(2) . . ?
C1 N1 C11A 116.84(18) . . ?
O2 C2 N1 119.6(2) . . ?
O2 C2 C21 122.0(2) . 2 ?
N1 C2 C21 118.26(19) . 2 ?
O3 C3 N2 119.9(2) . . ?
O3 C3 C23 122.7(2) . . ?
N2 C3 C23 117.11(18) . . ?
C4 N2 C3 118.43(18) . . ?
C4 N2 C21A 122.44(18) . . ?
C3 N2 C21A 115.49(17) . . ?
O4 C4 N2 120.8(2) . . ?
O4 C4 C11 120.5(2) . . ?
N2 C4 C11 118.70(19) . . ?
C16 C11 C12 119.3(2) . . ?
C16 C11 C4 117.0(2) . . ?
C12 C11 C4 123.3(2) . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 C1 117.9(2) . . ?
C12 C13 C1 122.6(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C16A C11A N12A 119.9(10) . . ?
C16A C11A C16B 129(2) . . ?
N12A C11A N12B 130.0(19) . . ?
C16B C11A N12B 139(3) . . ?
C16A C11A N1 120.8(9) . . ?
N12A C11A N1 119.2(5) . . ?
C16B C11A N1 110(2) . . ?
N12B C11A N1 110.8(18) . . ?
C13A N12A C11A 121.4(9) . . ?
N12A C13A C14A 122.4(9) . . ?
N12A C13A H13A 118.8 . . ?
C14A C13A H13A 118.8 . . ?
C13A C14A C17A 124.8(9) . . ?
C13A C14A C15A 113.4(9) . . ?
C17A C14A C15A 121.8(10) . . ?
C16A C15A C14A 117.6(14) . . ?
C16A C15A H15A 121.2 . . ?
C14A C15A H15A 121.2 . . ?
C15A C16A C11A 125.3(17) . . ?
C15A C16A H16A 117.4 . . ?
C11A C16A H16A 117.4 . . ?
C14B C13B N12B 126(5) . . ?
C14B C13B H13B 116.8 . . ?
N12B C13B H13B 116.8 . . ?
C13B C14B C15B 134(5) . . ?
C14B C15B C16B 127(4) . . ?
C14B C15B H15B 116.4 . . ?
C16B C15B H15B 116.4 . . ?
C15B C16B H16B 131.9 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C22 C21 C26 119.0(2) . . ?
C22 C21 C2 121.73(19) . 2 ?
C26 C21 C2 119.1(2) . 2 ?
C21 C22 C23 120.59(19) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 119.4(2) . . ?
C22 C23 C3 121.57(18) . . ?
C24 C23 C3 118.7(2) . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.0(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
N22A C21A N22B 122.3(11) . . ?
N22A C21A C26A 118.3(11) . . ?
N22A C21A N2 123.1(9) . . ?
N22B C21A N2 114.7(7) . . ?
C26A C21A N2 118.6(7) . . ?
N22B C21A C26B 134.3(15) . . ?
C26A C21A C26B 130.3(15) . . ?
N2 C21A C26B 111.1(14) . . ?
C21A N22A C23A 126.0(13) . . ?
C24A C23A N22A 121(2) . . ?
C24A C23A H23A 119.4 . . ?
N22A C23A H23A 119.4 . . ?
C23A C24A C27A 130(2) . . ?
C23A C24A C25A 115(2) . . ?
C27A C24A C25A 114(2) . . ?
C26A C25A C24A 123(2) . . ?
C26A C25A H25A 118.4 . . ?
C24A C25A H25A 118.4 . . ?
C25A C26A C21A 116.1(12) . . ?
C25A C26A H26A 122.0 . . ?
C21A C26A H26A 122.0 . . ?
C24B C23B N22B 123(2) . . ?
C24B C23B H23B 118.7 . . ?
N22B C23B H23B 118.7 . . ?
C23B C24B C25B 116(3) . . ?
C26B C25B C24B 129(2) . . ?
C26B C25B H25B 115.7 . . ?
C24B C25B H25B 115.7 . . ?
C24B C27A H27A 118.5 . . ?
H27A C27A H27B 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
H27D C27A H27E 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
Cl1S C1S Cl3S 89.7(5) . . ?
Cl1S C1S Cl2S 111.0(5) . . ?
Cl3S C1S Cl2S 143.5(6) . . ?
Cl1S C1S Cl3S 112.9(5) . 2_655 ?
Cl2S C1S Cl2S 107.1(4) . 2_655 ?
Cl1S C1S H1S 107(5) . . ?
Cl2S C1S H1S 125(5) . . ?
Cl3S C1S H1S 109(4) 2_655 . ?

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
O1 C1 N1 C2 120.5(3) . . . . ?
C13 C1 N1 C2 -62.6(3) . . . . ?
O1 C1 N1 C11A -35.4(3) . . . . ?
C13 C1 N1 C11A 141.6(2) . . . . ?
C1 N1 C2 O2 -8.9(3) . . . . ?
C11A N1 C2 O2 145.7(2) . . . . ?
C1 N1 C2 C21 168.07(19) . . . 2 ?
C11A N1 C2 C21 -37.3(3) . . . 2 ?
O3 C3 N2 C4 -130.4(3) . . . . ?
C23 C3 N2 C4 54.9(3) . . . . ?
O3 C3 N2 C21A 28.6(3) . . . . ?
C23 C3 N2 C21A -146.0(2) . . . . ?
C3 N2 C4 O4 6.9(3) . . . . ?
C21A N2 C4 O4 -150.6(2) . . . . ?
C3 N2 C4 C11 -171.00(19) . . . . ?
C21A N2 C4 C11 31.5(3) . . . . ?
O4 C4 C11 C16 34.6(3) . . . . ?
N2 C4 C11 C16 -147.5(2) . . . . ?
O4 C4 C11 C12 -138.4(2) . . . . ?
N2 C4 C11 C12 39.5(3) . . . . ?
C16 C11 C12 C13 -1.9(3) . . . . ?
C4 C11 C12 C13 170.91(19) . . . . ?
C11 C12 C13 C14 1.8(3) . . . . ?
C11 C12 C13 C1 -172.7(2) . . . . ?
O1 C1 C13 C14 -18.5(4) . . . . ?
N1 C1 C13 C14 164.6(2) . . . . ?
O1 C1 C13 C12 156.1(3) . . . . ?
N1 C1 C13 C12 -20.8(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C1 C13 C14 C15 175.2(2) . . . . ?
C13 C14 C15 C16 -2.7(4) . . . . ?
C14 C15 C16 C11 2.5(4) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
C4 C11 C16 C15 -173.5(2) . . . . ?
C2 N1 C11A C16A 150.9(8) . . . . ?
C1 N1 C11A C16A -54.5(9) . . . . ?
C2 N1 C11A N12A -27.1(6) . . . . ?
C1 N1 C11A N12A 127.5(5) . . . . ?
C2 N1 C11A C16B -35(2) . . . . ?
C1 N1 C11A C16B 120(2) . . . . ?
C2 N1 C11A N12B 151.5(17) . . . . ?
C1 N1 C11A N12B -53.9(17) . . . . ?
C16A C11A N12A C13A -1.5(14) . . . . ?
C16B C11A N12A C13A -144(10) . . . . ?
N12B C11A N12A C13A -2(2) . . . . ?
N1 C11A N12A C13A 176.6(8) . . . . ?
C11A N12A C13A C14A 2.3(16) . . . . ?
N12A C13A C14A C17A 178.4(9) . . . . ?
N12A C13A C14A C15A -1.5(14) . . . . ?
C13A C14A C15A C16A -0.1(13) . . . . ?
C17A C14A C15A C16A -180.0(11) . . . . ?
C14A C15A C16A C11A 0.9(18) . . . . ?
N12A C11A C16A C15A -0.2(18) . . . . ?
N1 C11A C16A C15A -178.3(10) . . . . ?
C11A N12B C13B C14B -1(4) . . . . ?
N12B C13B C14B C15B -2(7) . . . . ?
C13B C14B C15B C16B 0(8) . . . . ?
N1 C11A C16B C15B -179(2) . . . . ?
C26 C21 C22 C23 1.3(3) . . . . ?
C2 C21 C22 C23 -173.8(2) 2 . . . ?
C21 C22 C23 C24 -2.0(3) . . . . ?
C21 C22 C23 C3 171.2(2) . . . . ?
O3 C3 C23 C22 -149.1(3) . . . . ?
N2 C3 C23 C22 25.4(3) . . . . ?
O3 C3 C23 C24 24.1(4) . . . . ?
N2 C3 C23 C24 -161.4(2) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C3 C23 C24 C25 -172.9(2) . . . . ?
C23 C24 C25 C26 1.7(4) . . . . ?
C24 C25 C26 C21 -2.3(4) . . . . ?
C22 C21 C26 C25 0.8(4) . . . . ?
C2 C21 C26 C25 176.1(2) 2 . . . ?
C4 N2 C21A N22A 42.8(15) . . . . ?
C3 N2 C21A N22A -115.3(14) . . . . ?
C4 N2 C21A N22B -138.4(8) . . . . ?
C3 N2 C21A N22B 63.5(8) . . . . ?
C4 N2 C21A C26A -140.5(6) . . . . ?
C3 N2 C21A C26A 61.4(6) . . . . ?
N22B C21A N22A C23A 2(3) . . . . ?
C26A C21A N22A C23A 4(3) . . . . ?
N2 C21A N22A C23A -178.8(17) . . . . ?
C21A N22A C23A C24A -9(4) . . . . ?
N22A C23A C24A C27A 178(2) . . . . ?
N22A C23A C24A C25A 8(3) . . . . ?
C23A C24A C25A C26A -5(4) . . . . ?
C27A C24A C25A C26A -176.5(16) . . . . ?
C24A C25A C26A C21A 1(3) . . . . ?
N22A C21A C26A C25A -1(2) . . . . ?
N2 C21A C26A C25A -177.7(11) . . . . ?
N22B C23B C24B C25B 8(4) . . . . ?
C23B C24B C25B C26B -9(5) . . . . ?


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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
C22 H22 N2 0.93 2.59 2.910(3) 100 . yes
C23A H23A O2 0.93 2.48 3.251(14) 141 5_565 yes
#   C1S  H1S  N22A  1.00(2)   2.64(4)   3.56(2)   154(6)    2      yes



#========================================================================




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12-007
_audit_block_doi                 10.5517/cc14n9nr
_database_code_depnum_ccdc_archive 'CCDC 1062204'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'ClIO4 chloroform solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H28 Cl4 N8 O8, 0.8(C H Cl3)'
_chemical_formula_sum            'C52.80 H28.80 Cl6.40 N8 O8'
_chemical_formula_weight         1130.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.9915(6)
_cell_length_b                   19.1005(8)
_cell_length_c                   19.0658(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5095.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2229
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      63.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             2297.6
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.809
_shelx_estimated_absorpt_T_min   0.581
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            27221
_diffrn_reflns_av_unetI/netI     0.1626
_diffrn_reflns_av_R_equivalents  0.1877
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.552
_diffrn_reflns_theta_max         63.718
_diffrn_reflns_theta_full        60.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_standards_number         2229
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_reflns_number_total             4130
_reflns_number_gt                1275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/6
_refine_special_details          'disordered solvent'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.00013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4130
_refine_ls_number_parameters     357
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   0.703
_refine_ls_restrained_S_all      0.704
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl14 Cl 0.63043(12) 0.35934(10) -0.28516(9) 0.1317(8) Uani 1 1 d . . . . .
Cl24 Cl 0.11575(12) 0.51681(8) 0.11405(7) 0.0992(6) Uani 1 1 d . . . . .
O1 O 0.1761(2) 0.4115(2) -0.28702(17) 0.1031(15) Uani 1 1 d . . . . .
C1 C 0.1667(4) 0.3970(3) -0.2265(3) 0.0648(16) Uani 1 1 d . . . . .
N1 N 0.2446(3) 0.4050(2) -0.1787(2) 0.0576(11) Uani 1 1 d . . . . .
O2 O 0.1542(3) 0.48039(19) -0.11590(19) 0.0895(13) Uani 1 1 d . . . . .
C2 C 0.2274(4) 0.4463(3) -0.1197(3) 0.0617(15) Uani 1 1 d . . . . .
O3 O 0.0431(3) 0.19232(18) 0.10510(17) 0.1068(16) Uani 1 1 d . . . . .
C3 C 0.0592(4) 0.1831(3) 0.0441(3) 0.0644(16) Uani 1 1 d . . . . .
N2 N 0.0481(3) 0.2400(2) -0.00468(19) 0.0540(11) Uani 1 1 d . . . . .
O4 O -0.0493(3) 0.17494(18) -0.07445(18) 0.0763(12) Uani 1 1 d . . . . .
C4 C -0.0053(4) 0.2291(3) -0.0664(3) 0.0572(14) Uani 1 1 d . . . . .
C11 C -0.0032(4) 0.2841(2) -0.1220(2) 0.0530(13) Uani 1 1 d . . . . .
C12 C 0.0789(4) 0.3200(2) -0.1403(2) 0.0510(14) Uani 1 1 d . . . . .
H12 H 0.1338 0.3155 -0.1132 0.061 Uiso 1 1 calc R U . . .
C13 C 0.0791(4) 0.3629(3) -0.1992(2) 0.0535(14) Uani 1 1 d . . . . .
C14 C -0.0042(4) 0.3701(3) -0.2382(2) 0.0627(15) Uani 1 1 d . . . . .
H14 H -0.0037 0.3979 -0.2783 0.075 Uiso 1 1 calc R U . . .
C15 C -0.0872(4) 0.3372(3) -0.2188(3) 0.0691(17) Uani 1 1 d . . . . .
H15 H -0.1434 0.3449 -0.2437 0.083 Uiso 1 1 calc R U . . .
C16 C -0.0863(4) 0.2920(3) -0.1614(3) 0.0667(16) Uani 1 1 d . . . . .
H16 H -0.1411 0.2672 -0.1494 0.080 Uiso 1 1 calc R U . . .
C11A C 0.3389(4) 0.3938(3) -0.2066(2) 0.0562(14) Uani 1 1 d . . . . .
N12A N 0.4045(4) 0.4469(2) -0.1980(2) 0.0805(15) Uani 1 1 d . . . . .
C13A C 0.4943(4) 0.4332(3) -0.2224(3) 0.0774(18) Uani 1 1 d . . . . .
H13A H 0.5421 0.4665 -0.2161 0.093 Uiso 1 1 calc R U . . .
C14A C 0.5155(4) 0.3729(4) -0.2553(3) 0.0695(17) Uani 1 1 d . . . . .
C15A C 0.4461(5) 0.3235(3) -0.2650(3) 0.0733(18) Uani 1 1 d . . . . .
H15A H 0.4600 0.2826 -0.2894 0.088 Uiso 1 1 calc R U . . .
C16A C 0.3573(4) 0.3341(3) -0.2390(2) 0.0565(14) Uani 1 1 d . . . . .
H16A H 0.3101 0.3001 -0.2439 0.068 Uiso 1 1 calc R U . . .
C21 C 0.2020(4) 0.0544(3) -0.0621(3) 0.0555(14) Uani 1 1 d . . . . .
C22 C 0.1554(3) 0.1159(3) -0.0432(2) 0.0512(13) Uani 1 1 d . . . . .
H22 H 0.1630 0.1562 -0.0699 0.061 Uiso 1 1 calc R U . . .
C23 C 0.0973(3) 0.1168(3) 0.0158(2) 0.0534(14) Uani 1 1 d . . . . .
C24 C 0.0825(4) 0.0554(3) 0.0541(2) 0.0622(15) Uani 1 1 d . . . . .
H24 H 0.0428 0.0560 0.0932 0.075 Uiso 1 1 calc R U . . .
C25 C 0.1264(4) -0.0057(3) 0.0343(3) 0.0730(17) Uani 1 1 d . . . . .
H25 H 0.1154 -0.0469 0.0591 0.088 Uiso 1 1 calc R U . . .
C26 C 0.1872(4) -0.0054(3) -0.0231(3) 0.0677(17) Uani 1 1 d . . . . .
H26 H 0.2187 -0.0465 -0.0356 0.081 Uiso 1 1 calc R U . . .
C21A C 0.0662(4) 0.3090(3) 0.0243(2) 0.0509(14) Uani 1 1 d . . . . .
N22A N -0.0089(3) 0.3540(3) 0.0231(2) 0.0779(14) Uani 1 1 d . . . . .
C23A C 0.0090(4) 0.4203(3) 0.0514(2) 0.0665(16) Uani 1 1 d . . . . .
H23A H -0.0384 0.4544 0.0508 0.080 Uiso 1 1 calc R U . . .
C24A C 0.0953(4) 0.4345(3) 0.0795(2) 0.0536(14) Uani 1 1 d . . . . .
C25A C 0.1667(4) 0.3848(3) 0.0795(2) 0.0644(16) Uani 1 1 d . . . . .
H25A H 0.2260 0.3946 0.0991 0.077 Uiso 1 1 calc R U . . .
C26A C 0.1494(4) 0.3226(3) 0.0510(2) 0.0470(13) Uani 1 1 d . . . . .
H26A H 0.1971 0.2888 0.0501 0.056 Uiso 1 1 calc R U . . .
Cl1S Cl 0.3169(7) 0.6945(6) -0.1046(4) 0.128(2) Uani 0.4 1 d D . P A -1
Cl2S Cl 0.2177(15) 0.7965(9) -0.0622(7) 0.358(12) Uani 0.4 1 d D . P A -1
Cl3S Cl 0.2466(4) 0.7019(3) 0.0231(2) 0.156(3) Uani 0.4 1 d D . P A -1
C1S C 0.219(2) 0.7110(17) -0.0600(13) 0.37(4) Uiso 0.4 1 d D . P A -1
H1S H 0.1611 0.6872 -0.0759 0.440 Uiso 0.4 1 calc R U P A -1


_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
Cl14 C14A 1.726(5) . ?
Cl24 C24A 1.729(5) . ?
O1 C1 1.194(5) . ?
C1 N1 1.430(5) . ?
C1 C13 1.482(6) . ?
N1 C2 1.395(6) . ?
N1 C11A 1.439(5) . ?
O2 C2 1.217(5) . ?
C2 C21 1.476(6) 2 ?
O3 C3 1.197(5) . ?
C3 N2 1.438(5) . ?
C3 C23 1.476(6) . ?
N2 C4 1.408(5) . ?
N2 C21A 1.450(6) . ?
O4 C4 1.214(5) . ?
C4 C11 1.492(6) . ?
C11 C12 1.382(6) . ?
C11 C16 1.393(6) . ?
C12 C13 1.391(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(6) . ?
C14 C15 1.372(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11A C16A 1.322(6) . ?
C11A N12A 1.377(6) . ?
N12A C13A 1.366(6) . ?
C13A C14A 1.345(6) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.367(7) . ?
C15A C16A 1.353(6) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21 C26 1.380(6) . ?
C21 C22 1.392(6) . ?
C21 C2 1.476(6) 2 ?
C22 C23 1.388(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(6) . ?
C24 C25 1.373(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.386(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21A C26A 1.297(6) . ?
C21A N22A 1.357(6) . ?
N22A C23A 1.399(6) . ?
C23A C24A 1.348(6) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.378(6) . ?
C25A C26A 1.328(6) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
Cl1S C1S 1.64(3) . ?
Cl2S C1S 1.63(3) . ?
Cl2S Cl3S 2.464(17) . ?
Cl3S C1S 1.64(3) . ?
C1S H1S 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
O1 C1 N1 120.5(5) . . ?
O1 C1 C13 122.1(5) . . ?
N1 C1 C13 117.0(4) . . ?
C2 N1 C1 116.3(5) . . ?
C2 N1 C11A 122.7(5) . . ?
C1 N1 C11A 116.6(4) . . ?
O2 C2 N1 119.8(6) . . ?
O2 C2 C21 121.6(5) . 2 ?
N1 C2 C21 118.6(5) . 2 ?
O3 C3 N2 119.8(5) . . ?
O3 C3 C23 123.2(5) . . ?
N2 C3 C23 116.8(4) . . ?
C4 N2 C3 119.1(4) . . ?
C4 N2 C21A 123.0(4) . . ?
C3 N2 C21A 114.9(4) . . ?
O4 C4 N2 120.0(5) . . ?
O4 C4 C11 121.3(5) . . ?
N2 C4 C11 118.6(5) . . ?
C12 C11 C16 120.2(5) . . ?
C12 C11 C4 123.0(5) . . ?
C16 C11 C4 116.3(5) . . ?
C11 C12 C13 119.9(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 C1 117.5(5) . . ?
C12 C13 C1 123.0(5) . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.2(5) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 119.9(5) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16A C11A N12A 124.2(5) . . ?
C16A C11A N1 118.6(6) . . ?
N12A C11A N1 117.2(5) . . ?
C13A N12A C11A 115.6(5) . . ?
C14A C13A N12A 121.7(6) . . ?
C14A C13A H13A 119.2 . . ?
N12A C13A H13A 119.2 . . ?
C13A C14A C15A 119.9(6) . . ?
C13A C14A Cl14 119.2(6) . . ?
C15A C14A Cl14 120.9(6) . . ?
C16A C15A C14A 120.0(5) . . ?
C16A C15A H15A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C11A C16A C15A 118.6(5) . . ?
C11A C16A H16A 120.7 . . ?
C15A C16A H16A 120.7 . . ?
C26 C21 C22 119.2(5) . . ?
C26 C21 C2 119.6(5) . 2 ?
C22 C21 C2 121.0(5) . 2 ?
C23 C22 C21 119.7(5) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.0(5) . . ?
C22 C23 C3 121.2(5) . . ?
C24 C23 C3 118.4(5) . . ?
C25 C24 C23 120.3(5) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.2(5) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C21 C26 C25 121.4(5) . . ?
C21 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26A C21A N22A 125.0(5) . . ?
C26A C21A N2 119.3(5) . . ?
N22A C21A N2 115.7(5) . . ?
C21A N22A C23A 115.4(5) . . ?
C24A C23A N22A 119.7(5) . . ?
C24A C23A H23A 120.2 . . ?
N22A C23A H23A 120.2 . . ?
C23A C24A C25A 120.7(5) . . ?
C23A C24A Cl24 118.9(5) . . ?
C25A C24A Cl24 120.4(5) . . ?
C26A C25A C24A 118.9(5) . . ?
C26A C25A H25A 120.5 . . ?
C24A C25A H25A 120.5 . . ?
C21A C26A C25A 120.3(5) . . ?
C21A C26A H26A 119.8 . . ?
C25A C26A H26A 119.8 . . ?
Cl2S C1S Cl1S 101.0(18) . . ?
Cl2S C1S Cl3S 97.6(18) . . ?
Cl1S C1S Cl3S 106.7(17) . . ?
Cl2S C1S H1S 116.3 . . ?
Cl1S C1S H1S 116.3 . . ?
Cl3S C1S H1S 116.3 . . ?

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
O1 C1 N1 C2 124.9(6) . . . . ?
C13 C1 N1 C2 -61.8(6) . . . . ?
O1 C1 N1 C11A -32.2(8) . . . . ?
C13 C1 N1 C11A 141.1(5) . . . . ?
C1 N1 C2 O2 -9.5(7) . . . . ?
C11A N1 C2 O2 146.0(5) . . . . ?
C1 N1 C2 C21 168.5(5) . . . 2 ?
C11A N1 C2 C21 -36.0(7) . . . 2 ?
O3 C3 N2 C4 -130.4(5) . . . . ?
C23 C3 N2 C4 54.0(6) . . . . ?
O3 C3 N2 C21A 30.4(7) . . . . ?
C23 C3 N2 C21A -145.2(5) . . . . ?
C3 N2 C4 O4 7.6(7) . . . . ?
C21A N2 C4 O4 -151.5(5) . . . . ?
C3 N2 C4 C11 -170.1(4) . . . . ?
C21A N2 C4 C11 30.8(7) . . . . ?
O4 C4 C11 C12 -137.6(5) . . . . ?
N2 C4 C11 C12 40.0(7) . . . . ?
O4 C4 C11 C16 34.7(7) . . . . ?
N2 C4 C11 C16 -147.6(4) . . . . ?
C16 C11 C12 C13 -1.5(7) . . . . ?
C4 C11 C12 C13 170.5(4) . . . . ?
C11 C12 C13 C14 1.3(7) . . . . ?
C11 C12 C13 C1 -173.3(4) . . . . ?
O1 C1 C13 C14 -22.5(8) . . . . ?
N1 C1 C13 C14 164.4(4) . . . . ?
O1 C1 C13 C12 152.1(5) . . . . ?
N1 C1 C13 C12 -21.0(7) . . . . ?
C12 C13 C14 C15 1.6(7) . . . . ?
C1 C13 C14 C15 176.4(5) . . . . ?
C13 C14 C15 C16 -4.2(8) . . . . ?
C12 C11 C16 C15 -1.1(7) . . . . ?
C4 C11 C16 C15 -173.6(4) . . . . ?
C14 C15 C16 C11 3.9(7) . . . . ?
C2 N1 C11A C16A 150.0(5) . . . . ?
C1 N1 C11A C16A -54.5(6) . . . . ?
C2 N1 C11A N12A -30.4(6) . . . . ?
C1 N1 C11A N12A 125.1(5) . . . . ?
C16A C11A N12A C13A -3.2(7) . . . . ?
N1 C11A N12A C13A 177.2(4) . . . . ?
C11A N12A C13A C14A 2.8(8) . . . . ?
N12A C13A C14A C15A 0.0(8) . . . . ?
N12A C13A C14A Cl14 179.7(4) . . . . ?
C13A C14A C15A C16A -2.6(8) . . . . ?
Cl14 C14A C15A C16A 177.7(4) . . . . ?
N12A C11A C16A C15A 0.8(8) . . . . ?
N1 C11A C16A C15A -179.6(4) . . . . ?
C14A C15A C16A C11A 2.2(8) . . . . ?
C26 C21 C22 C23 2.2(7) . . . . ?
C2 C21 C22 C23 -173.0(4) 2 . . . ?
C21 C22 C23 C24 -2.9(7) . . . . ?
C21 C22 C23 C3 170.1(5) . . . . ?
O3 C3 C23 C22 -149.3(5) . . . . ?
N2 C3 C23 C22 26.1(7) . . . . ?
O3 C3 C23 C24 23.8(8) . . . . ?
N2 C3 C23 C24 -160.8(4) . . . . ?
C22 C23 C24 C25 1.0(8) . . . . ?
C3 C23 C24 C25 -172.1(5) . . . . ?
C23 C24 C25 C26 1.5(8) . . . . ?
C22 C21 C26 C25 0.4(7) . . . . ?
C2 C21 C26 C25 175.7(4) 2 . . . ?
C24 C25 C26 C21 -2.2(8) . . . . ?
C4 N2 C21A C26A -140.7(5) . . . . ?
C3 N2 C21A C26A 59.3(6) . . . . ?
C4 N2 C21A N22A 41.4(6) . . . . ?
C3 N2 C21A N22A -118.5(5) . . . . ?
C26A C21A N22A C23A 2.1(8) . . . . ?
N2 C21A N22A C23A 179.8(4) . . . . ?
C21A N22A C23A C24A -2.3(7) . . . . ?
N22A C23A C24A C25A 1.2(7) . . . . ?
N22A C23A C24A Cl24 180.0(3) . . . . ?
C23A C24A C25A C26A 0.3(7) . . . . ?
Cl24 C24A C25A C26A -178.4(4) . . . . ?
N22A C21A C26A C25A -0.6(8) . . . . ?
N2 C21A C26A C25A -178.2(4) . . . . ?
C24A C25A C26A C21A -0.7(7) . . . . ?
Cl3S Cl2S C1S Cl1S -109(2) . . . . ?
Cl2S Cl3S C1S Cl1S 104(2) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H    H...A   D...A     D-H...A   symm   publ
#   -    -    -     ---    -----   -----     -------   ----   ----
C22 H22 N2 0.93 2.59 2.900(6) 100 . yes
C23A H23A O2 0.93 2.39 3.213(6) 147 5_565 yes
C25A H25A O1 0.93 2.59 3.403(6) 147 8_656 yes



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14-029
_audit_block_doi                 10.5517/cc14n9ps
_database_code_depnum_ccdc_archive 'CCDC 1062205'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'ClIO4 dichloromethane solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H28 Cl4 N8 O8, 0.305(C2 H4 Cl4)'
_chemical_formula_sum            'C52.61 H29.22 Cl5.22 N8 O8'
_chemical_formula_weight         1086.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.6868(9)
_cell_length_b                   19.0571(11)
_cell_length_c                   19.0700(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4974.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2750
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      70.30

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             2214.5
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    3.308
_shelx_estimated_absorpt_T_min   0.399
_shelx_estimated_absorpt_T_max   0.744
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            27344
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.977
_diffrn_reflns_theta_max         70.335
_diffrn_reflns_theta_full        62.500
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_standards_number         2750
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_reflns_number_total             3977
_reflns_number_gt                2658
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/6
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0811P)²+1.338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.00031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3977
_refine_ls_number_parameters     407
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1723
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl14 Cl 0.88105(11) -0.01542(6) -0.11415(6) 0.1007(5) Uani 1 1 d . . . . .
Cl24 Cl 0.36309(11) 0.14570(10) 0.29234(9) 0.1362(7) Uani 1 1 d . . . . .
O1 O 0.9701(3) 0.30917(16) -0.10236(16) 0.1244(15) Uani 1 1 d . . . . .
C1 C 0.9506(3) 0.31732(18) -0.04196(19) 0.0710(10) Uani 1 1 d . . . . .
N1 N 0.9595(2) 0.26001(14) 0.00621(14) 0.0604(7) Uani 1 1 d D . . . .
O2 O 1.0615(2) 0.32336(14) 0.07439(17) 0.0905(9) Uani 1 1 d . . . . .
C2 C 1.0148(3) 0.26950(18) 0.0667(2) 0.0655(9) Uani 1 1 d . . . . .
O3 O 0.8242(2) 0.0911(2) 0.28865(15) 0.1076(11) Uani 1 1 d . . . . .
C3 C 0.8345(3) 0.1065(2) 0.22788(19) 0.0669(9) Uani 1 1 d . . . . .
N2 N 0.7542(2) 0.09772(14) 0.18048(14) 0.0598(7) Uani 1 1 d D . . . .
O4 O 0.8460(2) 0.02095(16) 0.11903(18) 0.0967(10) Uani 1 1 d . . . . .
C4 C 0.7708(3) 0.05449(17) 0.12230(19) 0.0649(9) Uani 1 1 d . . . . .
C11 C 0.8004(3) 0.44471(16) 0.06429(18) 0.0606(9) Uani 1 1 d . . . . .
C12 C 0.8495(3) 0.38401(16) 0.04468(17) 0.0580(8) Uani 1 1 d . . . . .
H12 H 0.8428 0.3435 0.0715 0.070 Uiso 1 1 calc R U . . .
C13 C 0.9083(3) 0.38330(16) -0.01442(18) 0.0614(9) Uani 1 1 d . . . . .
C14 C 0.9203(3) 0.44410(18) -0.05366(19) 0.0707(10) Uani 1 1 d . . . . .
H14 H 0.9598 0.4439 -0.0933 0.085 Uiso 1 1 calc R U . . .
C15 C 0.8729(3) 0.50514(19) -0.0332(2) 0.0769(11) Uani 1 1 d . . . . .
H15 H 0.8818 0.5463 -0.0587 0.092 Uiso 1 1 calc R U . . .
C16 C 0.8130(3) 0.50499(18) 0.0243(2) 0.0724(11) Uani 1 1 d . . . . .
H16 H 0.7803 0.5459 0.0368 0.087 Uiso 1 1 calc R U . . .
C11A C 0.9438(13) 0.1917(6) -0.0221(10) 0.060(9) Uani 0.5 1 d D . P A -1
N12A N 0.8560(11) 0.1815(5) -0.0476(8) 0.059(5) Uani 0.5 1 d D . P A -1
C13A C 0.8333(13) 0.1205(8) -0.0753(13) 0.079(9) Uani 0.5 1 d D . P A -1
H13A H 0.7733 0.1148 -0.0975 0.095 Uiso 0.5 1 calc R U P A -1
C14A C 0.8980(13) 0.0647(13) -0.0717(13) 0.052(5) Uani 0.5 1 d D . P A -1
C15A C 0.9933(14) 0.0782(7) -0.0516(10) 0.067(7) Uani 0.5 1 d D . P A -1
H15A H 1.0400 0.0429 -0.0549 0.081 Uiso 0.5 1 calc R U P A -1
C16A C 1.0201(17) 0.1439(8) -0.0265(17) 0.066(7) Uani 0.5 1 d D . P A -1
H16A H 1.0839 0.1549 -0.0137 0.079 Uiso 0.5 1 calc R U P A -1
C11B C 0.9376(13) 0.1919(6) -0.0233(9) 0.055(9) Uani 0.5 1 d D . P A -2
N12B N 1.0087(13) 0.1457(8) -0.0185(14) 0.063(6) Uani 0.5 1 d D . P A -2
C13B C 0.9952(12) 0.0838(9) -0.0473(10) 0.083(9) Uani 0.5 1 d D . P A -2
H13B H 1.0432 0.0497 -0.0416 0.099 Uiso 0.5 1 calc R U P A -2
C14B C 0.9125(12) 0.0671(13) -0.0856(13) 0.059(6) Uani 0.5 1 d D . P A -2
C15B C 0.8344(14) 0.1136(7) -0.0818(10) 0.060(6) Uani 0.5 1 d D . P A -2
H15B H 0.7736 0.1005 -0.0993 0.072 Uiso 0.5 1 calc R U P A -2
C16B C 0.8465(15) 0.1794(9) -0.0519(12) 0.075(8) Uani 0.5 1 d D . P A -2
H16B H 0.7968 0.2126 -0.0511 0.089 Uiso 0.5 1 calc R U P A -2
C21 C 1.0122(2) 0.21548(17) 0.12248(17) 0.0573(8) Uani 1 1 d . . . . .
C22 C 0.9269(3) 0.18097(17) 0.14108(17) 0.0565(8) Uani 1 1 d . . . . .
H22 H 0.8709 0.1865 0.1140 0.068 Uiso 1 1 calc R U . . .
C23 C 0.9249(3) 0.13795(17) 0.20038(17) 0.0569(8) Uani 1 1 d . . . . .
C24 C 1.0101(3) 0.12873(19) 0.23884(19) 0.0663(9) Uani 1 1 d . . . . .
H24 H 1.0095 0.1002 0.2784 0.080 Uiso 1 1 calc R U . . .
C25 C 1.0952(3) 0.1613(2) 0.2192(2) 0.0737(10) Uani 1 1 d . . . . .
H25 H 1.1524 0.1534 0.2443 0.088 Uiso 1 1 calc R U . . .
C26 C 1.0957(3) 0.2059(2) 0.1618(2) 0.0698(10) Uani 1 1 d . . . . .
H26 H 1.1527 0.2295 0.1497 0.084 Uiso 1 1 calc R U . . .
C21A C 0.6581(2) 0.10809(17) 0.20836(18) 0.0592(9) Uani 1 1 d D . . . .
N22A N 0.5914(3) 0.05659(18) 0.20143(19) 0.0836(10) Uani 1 1 d . . . . .
C23A C 0.5006(3) 0.0692(2) 0.2274(3) 0.0858(12) Uani 1 1 d . . . . .
H23A H 0.4526 0.0349 0.2230 0.103 Uiso 1 1 calc R U . . .
C24A C 0.4783(3) 0.1314(2) 0.2601(2) 0.0787(12) Uani 1 1 d . . . . .
C25A C 0.5497(3) 0.1808(2) 0.2672(2) 0.0796(12) Uani 1 1 d . . . . .
H25A H 0.5365 0.2223 0.2910 0.096 Uiso 1 1 calc R U . . .
C26A C 0.6403(3) 0.16978(18) 0.23968(19) 0.0623(9) Uani 1 1 d . . . . .
H26A H 0.6885 0.2041 0.2425 0.075 Uiso 1 1 calc R U . . .
Cl1S Cl 0.1813(5) 0.3097(4) -0.0944(4) 0.166(2) Uani 0.305 1 d D . P . .
C1S C 0.272(2) 0.2707(17) -0.0548(15) 0.188(18) Uani 0.305 1 d D . P . .
H1S1 H 0.2616 0.3000 -0.0958 0.225 Uiso 0.305 1 calc R U P . .
H1S2 H 0.3399 0.2580 -0.0509 0.225 Uiso 0.305 1 calc R U P . .
Cl2S Cl 0.2575(6) 0.2036(5) -0.0047(5) 0.195(4) Uani 0.305 1 d D . P . .


_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
Cl14 C14B 1.72(2) . ?
Cl14 C14A 1.74(3) . ?
Cl24 C24A 1.714(4) . ?
O1 C1 1.193(4) . ?
C1 N1 1.432(4) . ?
C1 C13 1.481(5) . ?
N1 C2 1.392(5) . ?
N1 C11A 1.425(9) . ?
N1 C11B 1.446(7) . ?
O2 C2 1.218(4) . ?
C2 C21 1.480(5) . ?
O3 C3 1.203(4) . ?
C3 N2 1.433(5) . ?
C3 C23 1.472(5) . ?
N2 C4 1.400(4) . ?
N2 C21A 1.433(4) . ?
O4 C4 1.213(4) . ?
C4 C11 1.475(5) 2_655 ?
C11 C12 1.389(5) . ?
C11 C16 1.390(5) . ?
C11 C4 1.475(5) 2_655 ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(5) . ?
C14 C15 1.388(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11A N12A 1.312(9) . ?
C11A C16A 1.389(10) . ?
N12A C13A 1.313(9) . ?
C13A C14A 1.387(9) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.384(9) . ?
C15A C16A 1.389(10) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C11B N12B 1.315(9) . ?
C11B C16B 1.382(9) . ?
N12B C13B 1.315(9) . ?
C13B C14B 1.385(9) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.390(9) . ?
C15B C16B 1.387(10) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21 C26 1.379(5) . ?
C21 C22 1.385(5) . ?
C22 C23 1.397(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(5) . ?
C24 C25 1.371(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21A C26A 1.341(5) . ?
C21A N22A 1.346(5) . ?
N22A C23A 1.360(5) . ?
C23A C24A 1.374(6) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.364(6) . ?
C25A C26A 1.363(6) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
Cl1S C1S 1.63(2) . ?
C1S C1S 0.98(6) 2 ?
C1S Cl2S 1.15(3) 2 ?
C1S Cl2S 1.61(2) . ?
C1S Cl1S 1.83(4) 2 ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?
Cl2S Cl2S 1.78(2) 2 ?
Cl2S Cl1S 1.922(13) 2 ?

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
O1 C1 N1 120.1(3) . . ?
O1 C1 C13 122.7(3) . . ?
N1 C1 C13 117.0(3) . . ?
C2 N1 C11A 121.0(8) . . ?
C2 N1 C1 118.6(3) . . ?
C11A N1 C1 116.1(8) . . ?
C2 N1 C11B 123.5(8) . . ?
C1 N1 C11B 114.7(8) . . ?
O2 C2 N1 119.6(3) . . ?
O2 C2 C21 120.8(3) . . ?
N1 C2 C21 119.5(3) . . ?
O3 C3 N2 119.3(4) . . ?
O3 C3 C23 122.7(4) . . ?
N2 C3 C23 117.9(3) . . ?
C4 N2 C3 116.3(3) . . ?
C4 N2 C21A 121.6(3) . . ?
C3 N2 C21A 117.0(3) . . ?
O4 C4 N2 119.2(4) . . ?
O4 C4 C11 121.9(3) . 2_655 ?
N2 C4 C11 118.7(3) . 2_655 ?
C12 C11 C16 118.7(4) . . ?
C12 C11 C4 122.0(3) . 2_655 ?
C16 C11 C4 119.0(3) . 2_655 ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 C1 121.6(3) . . ?
C14 C13 C1 118.1(3) . . ?
C15 C14 C13 119.5(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N12A C11A C16A 124.7(11) . . ?
N12A C11A N1 114.5(11) . . ?
C16A C11A N1 120.6(12) . . ?
C11A N12A C13A 119.9(11) . . ?
N12A C13A C14A 120.5(19) . . ?
N12A C13A H13A 119.7 . . ?
C14A C13A H13A 119.7 . . ?
C15A C14A C13A 118(2) . . ?
C15A C14A Cl14 114.7(13) . . ?
C13A C14A Cl14 124.4(15) . . ?
C14A C15A C16A 120.9(18) . . ?
C14A C15A H15A 119.6 . . ?
C16A C15A H15A 119.6 . . ?
C11A C16A C15A 114.4(15) . . ?
C11A C16A H16A 122.8 . . ?
C15A C16A H16A 122.8 . . ?
N12B C11B C16B 125.4(11) . . ?
N12B C11B N1 114.9(12) . . ?
C16B C11B N1 119.7(12) . . ?
C13B N12B C11B 117.9(12) . . ?
N12B C13B C14B 122.8(17) . . ?
N12B C13B H13B 118.6 . . ?
C14B C13B H13B 118.6 . . ?
C13B C14B C15B 117(2) . . ?
C13B C14B Cl14 125.5(16) . . ?
C15B C14B Cl14 114.0(13) . . ?
C16B C15B C14B 120.3(19) . . ?
C16B C15B H15B 119.8 . . ?
C14B C15B H15B 119.8 . . ?
C11B C16B C15B 115.3(15) . . ?
C11B C16B H16B 122.4 . . ?
C15B C16B H16B 122.4 . . ?
C26 C21 C22 119.7(3) . . ?
C26 C21 C2 117.6(3) . . ?
C22 C21 C2 122.3(3) . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 119.0(3) . . ?
C24 C23 C3 117.8(3) . . ?
C22 C23 C3 123.0(3) . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 119.8(4) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.5(4) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26A C21A N22A 124.1(3) . . ?
C26A C21A N2 116.9(3) . . ?
N22A C21A N2 119.0(3) . . ?
C21A N22A C23A 117.1(4) . . ?
N22A C23A C24A 121.4(4) . . ?
N22A C23A H23A 119.3 . . ?
C24A C23A H23A 119.3 . . ?
C25A C24A C23A 118.7(4) . . ?
C25A C24A Cl24 121.0(4) . . ?
C23A C24A Cl24 120.3(4) . . ?
C26A C25A C24A 120.6(4) . . ?
C26A C25A H25A 119.7 . . ?
C24A C25A H25A 119.7 . . ?
C21A C26A C25A 118.1(4) . . ?
C21A C26A H26A 120.9 . . ?
C25A C26A H26A 120.9 . . ?
Cl2S C1S Cl2S 78.6(17) 2 . ?
C1S C1S Cl1S 85(3) 2 . ?
Cl2S C1S Cl1S 86(2) 2 . ?
Cl2S C1S Cl1S 123.3(17) . . ?
Cl2S C1S Cl1S 67.7(13) . 2 ?
Cl1S C1S Cl1S 117.4(19) . 2 ?
C1S C1S H1S1 112.2 2 . ?
Cl2S C1S H1S1 112.2 2 . ?
Cl2S C1S H1S1 157.0 . . ?
Cl1S C1S H1S1 101.5 2 . ?
C1S C1S H1S2 112.2 2 . ?
Cl2S C1S H1S2 112.2 2 . ?
Cl2S C1S H1S2 82.6 . . ?
Cl1S C1S H1S2 151.9 . . ?
Cl1S C1S H1S2 58.7 2 . ?
H1S1 C1S H1S2 109.8 . . ?
C1S Cl2S Cl1S 61.5(13) . 2 ?
Cl2S Cl2S Cl1S 100.4(5) 2 2 ?

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
O1 C1 N1 C2 126.9(5) . . . . ?
C13 C1 N1 C2 -58.5(5) . . . . ?
O1 C1 N1 C11A -30.1(10) . . . . ?
C13 C1 N1 C11A 144.5(9) . . . . ?
O1 C1 N1 C11B -33.6(10) . . . . ?
C13 C1 N1 C11B 141.1(9) . . . . ?
C11A N1 C2 O2 149.1(10) . . . . ?
C1 N1 C2 O2 -6.8(5) . . . . ?
C11B N1 C2 O2 151.8(10) . . . . ?
C11A N1 C2 C21 -33.9(10) . . . . ?
C1 N1 C2 C21 170.2(3) . . . . ?
C11B N1 C2 C21 -31.1(10) . . . . ?
O3 C3 N2 C4 -122.7(4) . . . . ?
C23 C3 N2 C4 60.8(4) . . . . ?
O3 C3 N2 C21A 32.7(5) . . . . ?
C23 C3 N2 C21A -143.8(3) . . . . ?
C3 N2 C4 O4 8.3(5) . . . . ?
C21A N2 C4 O4 -145.8(4) . . . . ?
C3 N2 C4 C11 -167.1(3) . . . 2_655 ?
C21A N2 C4 C11 38.8(4) . . . 2_655 ?
C16 C11 C12 C13 -1.3(5) . . . . ?
C4 C11 C12 C13 173.3(3) 2_655 . . . ?
C11 C12 C13 C14 1.5(5) . . . . ?
C11 C12 C13 C1 -171.6(4) . . . . ?
O1 C1 C13 C12 152.3(5) . . . . ?
N1 C1 C13 C12 -22.2(6) . . . . ?
O1 C1 C13 C14 -21.0(7) . . . . ?
N1 C1 C13 C14 164.6(3) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C1 C13 C14 C15 173.2(4) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
C14 C15 C16 C11 1.6(6) . . . . ?
C12 C11 C16 C15 -0.3(6) . . . . ?
C4 C11 C16 C15 -175.1(4) 2_655 . . . ?
C2 N1 C11A N12A 141.7(12) . . . . ?
C1 N1 C11A N12A -61.8(17) . . . . ?
C2 N1 C11A C16A -43.5(19) . . . . ?
C1 N1 C11A C16A 113.0(17) . . . . ?
C16A C11A N12A C13A 5(2) . . . . ?
N1 C11A N12A C13A 179.8(17) . . . . ?
C11A N12A C13A C14A 6(3) . . . . ?
N12A C13A C14A C15A -13(3) . . . . ?
N12A C13A C14A Cl14 -173.1(17) . . . . ?
C13A C14A C15A C16A 9(3) . . . . ?
Cl14 C14A C15A C16A 170.7(19) . . . . ?
N12A C11A C16A C15A -9(3) . . . . ?
N1 C11A C16A C15A 177(2) . . . . ?
C14A C15A C16A C11A 2(3) . . . . ?
C2 N1 C11B N12B -36.9(18) . . . . ?
C1 N1 C11B N12B 122.5(14) . . . . ?
C2 N1 C11B C16B 141.5(15) . . . . ?
C1 N1 C11B C16B -59(2) . . . . ?
C16B C11B N12B C13B 5(3) . . . . ?
N1 C11B N12B C13B -177(2) . . . . ?
C11B N12B C13B C14B 4(3) . . . . ?
N12B C13B C14B C15B -12(3) . . . . ?
N12B C13B C14B Cl14 -170.1(19) . . . . ?
C13B C14B C15B C16B 12(3) . . . . ?
Cl14 C14B C15B C16B 172.4(17) . . . . ?
N12B C11B C16B C15B -5(3) . . . . ?
N1 C11B C16B C15B 177.0(17) . . . . ?
C14B C15B C16B C11B -4(3) . . . . ?
O2 C2 C21 C26 -34.8(5) . . . . ?
N1 C2 C21 C26 148.3(3) . . . . ?
O2 C2 C21 C22 137.8(4) . . . . ?
N1 C2 C21 C22 -39.2(5) . . . . ?
C26 C21 C22 C23 1.6(5) . . . . ?
C2 C21 C22 C23 -170.8(3) . . . . ?
C21 C22 C23 C24 -2.0(5) . . . . ?
C21 C22 C23 C3 172.6(3) . . . . ?
O3 C3 C23 C24 21.4(6) . . . . ?
N2 C3 C23 C24 -162.2(3) . . . . ?
O3 C3 C23 C22 -153.2(4) . . . . ?
N2 C3 C23 C22 23.2(5) . . . . ?
C22 C23 C24 C25 0.1(5) . . . . ?
C3 C23 C24 C25 -174.8(4) . . . . ?
C23 C24 C25 C26 2.3(6) . . . . ?
C22 C21 C26 C25 0.8(5) . . . . ?
C2 C21 C26 C25 173.5(3) . . . . ?
C24 C25 C26 C21 -2.7(6) . . . . ?
C4 N2 C21A C26A -150.5(3) . . . . ?
C3 N2 C21A C26A 55.5(4) . . . . ?
C4 N2 C21A N22A 29.0(5) . . . . ?
C3 N2 C21A N22A -124.9(4) . . . . ?
C26A C21A N22A C23A 0.7(6) . . . . ?
N2 C21A N22A C23A -178.7(3) . . . . ?
C21A N22A C23A C24A -0.8(6) . . . . ?
N22A C23A C24A C25A -0.9(7) . . . . ?
N22A C23A C24A Cl24 180.0(3) . . . . ?
C23A C24A C25A C26A 2.8(6) . . . . ?
Cl24 C24A C25A C26A -178.1(3) . . . . ?
N22A C21A C26A C25A 1.0(6) . . . . ?
N2 C21A C26A C25A -179.4(3) . . . . ?
C24A C25A C26A C21A -2.8(6) . . . . ?
C1S C1S Cl2S Cl2S -113(4) 2 . . 2 ?
Cl1S C1S Cl2S Cl2S -77(3) . . . 2 ?
Cl1S C1S Cl2S Cl2S 174(2) 2 . . 2 ?
C1S C1S Cl2S Cl1S 73(3) 2 . . 2 ?
Cl2S C1S Cl2S Cl1S -174(2) 2 . . 2 ?
Cl1S C1S Cl2S Cl1S 109(3) . . . 2 ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H    H...A   D...A     D-H...A   symm   publ
#   -    -    -     ---    -----   -----     -------   ----   ----
C13B H13B O4 0.93 2.51 3.252(14) 137 5_755 yes
C12 H12 N1 0.93 2.57 2.896(4) 101 . yes







_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
