# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_H2L2I2_H2O
_database_code_depnum_ccdc_archive 'CCDC 1518139'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT027_H2L2I2_H2O          
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......       I Checked 
RESPONSE: Data have been collected up to theta max = 24 deg due to low intensity above theta = 22 deg.
;
_vrf_PLAT029_H2L2I2_H2O          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low ......       I Checked 
RESPONSE: Data completeness is 99 % up to theta = 23 deg. Intensity falls down above theta = 22 deg.
;
_vrf_PLAT306_H2L2I2_H2O          
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) (OW1)......         I Checked 
RESPONSE: Analysis of the deltaF map didn?t allow to localized the water hydrogen atoms.
Two residual peaks, found in the deltaF map near the OW1 atom, were tentatively introduced as hydrogen atoms
in the calculation and then removed because of serious problems concerning molecular geometry and ADPs.
;
_vrf_PLAT910_H2L2I2_H2O          
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)......         I Checked 
RESPONSE: Few reflections were lost due to too high beamstop limit. This problem do not affect the final observed reflections/parameters ratio 
(observed reflections/parameters ratio above 10). 
;
_vrf_PLAT911_H2L2I2_H2O          
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L= 0.600......         I Checked 
RESPONSE: Data have been collected up to theta max = 24 deg due to low intensity above theta = 22 deg. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H28 I2 N6 O3'
_chemical_formula_weight         582.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.7303(6)
_cell_length_b                   7.7864(6)
_cell_length_c                   22.0222(19)
_cell_angle_alpha                86.949(7)
_cell_angle_beta                 87.158(7)
_cell_angle_gamma                60.575(8)
_cell_volume                     1152.49(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2179
_cell_measurement_theta_min      4.7940
_cell_measurement_theta_max      23.6020

_exptl_crystal_description       prismatic
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.751
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.94380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.4547
_diffrn_reflns_number            7075
_diffrn_reflns_av_unetI/netI     0.1101
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.001
_diffrn_reflns_theta_max         26.356
_diffrn_reflns_theta_full        24.000
_diffrn_measured_fraction_theta_max 0.777
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.777
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.777
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             3664
_reflns_number_gt                2505
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Data have been collected up to theta max = 24 deg due to low intensity above theta = 22 deg 

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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.8'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_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)+(0.0031P)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_number_reflns         3664
_refine_ls_number_parameters     226
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.2377(12) 0.6353(10) -0.1835(4) 0.029(2) Uani 1 1 d . . . . .
H1A H 0.3706 0.6178 -0.1817 0.035 Uiso 1 1 calc R U . . .
H1B H 0.2482 0.5199 -0.2019 0.035 Uiso 1 1 calc R U . . .
C2 C 0.1109(13) 0.8184(11) -0.2235(4) 0.037(2) Uani 1 1 d . . . . .
H2A H 0.1785 0.8091 -0.2625 0.044 Uiso 1 1 calc R U . . .
H2B H -0.0153 0.8256 -0.2307 0.044 Uiso 1 1 calc R U . . .
O1 O 0.0772(8) 0.9918(7) -0.1944(3) 0.0385(16) Uani 1 1 d . . . . .
C3 C -0.0247(12) 1.0119(11) -0.1350(4) 0.037(2) Uani 1 1 d . . . . .
H3A H -0.1502 1.0159 -0.1407 0.044 Uiso 1 1 calc R U . . .
H3B H -0.0537 1.1363 -0.1183 0.044 Uiso 1 1 calc R U . . .
C4 C 0.0963(12) 0.8438(9) -0.0889(4) 0.029(2) Uani 1 1 d . . . . .
H4A H 0.2157 0.8465 -0.0790 0.034 Uiso 1 1 calc R U . . .
H4B H 0.0182 0.8581 -0.0518 0.034 Uiso 1 1 calc R U . . .
N1 N 0.1502(9) 0.6502(8) -0.1182(3) 0.0261(18) Uani 1 1 d . . . . .
H1 H 0.0257 0.6474 -0.1215 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2768(12) 0.4824(10) -0.0735(4) 0.027(2) Uani 1 1 d . . . . .
H5A H 0.2056 0.5012 -0.0347 0.032 Uiso 1 1 calc R U . . .
H5B H 0.3993 0.4836 -0.0669 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3253(12) 0.2815(9) -0.0986(4) 0.030(2) Uani 1 1 d . . . . .
H6A H 0.4188 0.2482 -0.1328 0.037 Uiso 1 1 calc R U . . .
H6B H 0.2055 0.2855 -0.1118 0.037 Uiso 1 1 calc R U . . .
C7 C 0.4177(12) 0.1275(11) -0.0450(4) 0.027(2) Uani 1 1 d . . . . .
N2 N 0.6045(10) 0.0807(9) -0.0295(3) 0.0301(19) Uani 1 1 d . . . . .
N3 N 0.3112(10) 0.0529(9) -0.0171(3) 0.0298(19) Uani 1 1 d . . . . .
C8 C 0.1313(12) -0.3163(10) 0.3145(4) 0.026(2) Uani 1 1 d . . . . .
H8A H 0.1214 -0.4359 0.3159 0.032 Uiso 1 1 calc R U . . .
H8B H 0.0104 -0.2107 0.2972 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3087(13) -0.3458(11) 0.2735(4) 0.037(2) Uani 1 1 d . . . . .
H9A H 0.2963 -0.3869 0.2339 0.044 Uiso 1 1 calc R U . . .
H9B H 0.3100 -0.2221 0.2680 0.044 Uiso 1 1 calc R U . . .
O2 O 0.4882(8) -0.4901(8) 0.2994(3) 0.0419(17) Uani 1 1 d . . . . .
C10 C 0.5111(12) -0.4364(11) 0.3606(4) 0.040(3) Uani 1 1 d . . . . .
H10A H 0.5137 -0.3130 0.3572 0.048 Uiso 1 1 calc R U . . .
H10B H 0.6381 -0.5369 0.3761 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3475(11) -0.4142(10) 0.4065(4) 0.027(2) Uani 1 1 d . . . . .
H11A H 0.3649 -0.3685 0.4446 0.033 Uiso 1 1 calc R U . . .
H11B H 0.3521 -0.5402 0.4142 0.033 Uiso 1 1 calc R U . . .
N4 N 0.1499(10) -0.2654(8) 0.3796(3) 0.0287(18) Uani 1 1 d . . . . .
H4 H 0.1479 -0.1384 0.3766 0.034 Uiso 1 1 calc R U . . .
C12 C -0.0129(11) -0.2424(10) 0.4251(4) 0.024(2) Uani 1 1 d . . . . .
H12A H 0.0139 -0.2103 0.4643 0.029 Uiso 1 1 calc R U . . .
H12B H -0.0146 -0.3662 0.4300 0.029 Uiso 1 1 calc R U . . .
C13 C -0.2148(11) -0.0804(10) 0.4039(4) 0.030(2) Uani 1 1 d . . . . .
H13A H -0.2070 0.0374 0.3920 0.037 Uiso 1 1 calc R U . . .
H13B H -0.2532 -0.1229 0.3688 0.037 Uiso 1 1 calc R U . . .
C14 C -0.3688(11) -0.0345(11) 0.4550(4) 0.024(2) Uani 1 1 d . . . . .
N5 N -0.4473(10) 0.1407(8) 0.4828(3) 0.0298(19) Uani 1 1 d . . . . .
N6 N -0.4180(9) -0.1774(8) 0.4715(3) 0.0270(18) Uani 1 1 d . . . . .
I1 I 0.12437(8) 0.19363(7) 0.38211(3) 0.0339(2) Uani 1 1 d . . . . .
I2 I 0.28156(8) 0.37819(7) 0.11739(3) 0.03316(19) Uani 1 1 d . . . . .
OW1 O -0.4458(13) -0.0430(11) 0.2541(4) 0.116(3) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.533(9) . ?
C1 N1 1.544(9) . ?
C2 O1 1.425(8) . ?
O1 C3 1.469(9) . ?
C3 C4 1.539(10) . ?
C4 N1 1.523(8) . ?
N1 C5 1.528(8) . ?
C5 C6 1.545(9) . ?
C6 C7 1.559(10) . ?
C7 N3 1.332(10) . ?
C7 N2 1.362(9) . ?
N2 N3 1.358(8) 2_655 ?
N3 N2 1.358(8) 2_655 ?
C8 C9 1.529(10) . ?
C8 N4 1.540(9) . ?
C9 O2 1.411(8) . ?
O2 C10 1.475(9) . ?
C10 C11 1.526(11) . ?
C11 N4 1.518(8) . ?
N4 C12 1.514(9) . ?
C12 C13 1.523(9) . ?
C13 C14 1.517(10) . ?
C14 N5 1.358(9) . ?
C14 N6 1.368(9) . ?
N5 N6 1.347(9) 2_456 ?
N6 N5 1.347(9) 2_456 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 112.5(6) . . ?
O1 C2 C1 110.1(6) . . ?
C2 O1 C3 111.6(6) . . ?
O1 C3 C4 113.6(6) . . ?
N1 C4 C3 107.5(6) . . ?
C4 N1 C5 107.7(6) . . ?
C4 N1 C1 113.2(6) . . ?
C5 N1 C1 116.0(5) . . ?
N1 C5 C6 110.4(6) . . ?
C5 C6 C7 105.9(6) . . ?
N3 C7 N2 124.3(8) . . ?
N3 C7 C6 119.2(7) . . ?
N2 C7 C6 116.4(8) . . ?
C7 N2 N3 117.8(7) . 2_655 ?
C7 N3 N2 117.9(6) . 2_655 ?
C9 C8 N4 112.0(7) . . ?
O2 C9 C8 110.5(7) . . ?
C9 O2 C10 111.5(6) . . ?
O2 C10 C11 114.2(7) . . ?
C10 C11 N4 107.6(6) . . ?
C12 N4 C11 107.8(6) . . ?
C12 N4 C8 116.7(6) . . ?
C11 N4 C8 111.6(6) . . ?
N4 C12 C13 110.8(6) . . ?
C14 C13 C12 109.7(6) . . ?
N5 C14 N6 123.3(8) . . ?
N5 C14 C13 119.6(8) . . ?
N6 C14 C13 117.2(7) . . ?
N6 N5 C14 118.6(7) 2_456 . ?
N5 N6 C14 118.2(6) 2_456 . ?

_refine_diff_density_max         1.342
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.150

####################################################################### 
# 
# 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_H2L2_2I3_2H2O
_database_code_depnum_ccdc_archive 'CCDC 1518138'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT972_H2L2_2I3_2H2O       
;
PROBLEM: Check Calcd Residual Density ...... (I1, I2, I3, I4, I5 and I6)        I Checked 
RESPONSE: residual electron density remained at the end of refinements close to 
iodine atoms most likely due to series truncation errors.
;
_vrf_THETM01_H2L2_2I3_2H2O       
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575 ......      I Checked 
RESPONSE: Data have been collected up to 0.87 Angstrom. Completeness at theta max was 96 %.
 The relative low resolution and completeness do not affect the final observed reflections/parameters ratio 
 (observed reflections/parameters ratio = 12.
;
_vrf_PLAT306_H2L2_2I3_2H2O       
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) (OW1 and OW2)......         I Checked 
RESPONSE: Analysis of the deltaF map didn?t allow to localized the water hydrogen atoms
;
_vrf_PLAT342_H2L2_2I3_2H2O       
;
PROBLEM: Low Bond Precision on C-C Bonds ......         I Checked 
RESPONSE: The quality of this structure is poor, as denoted even by the high values for the agreement factors
at the end of refinement. Nevertheless the overall connectivity is clear. 
Bond precision on C-C bonds is 0.031 for four C-C bonds and below 0.03 for the remaining ten C-C bonds. The mean
precision is 0.0288 
;
_vrf_PLAT430_H2L2_2I3_2H2O       
;
PROBLEM: Short Inter D...A Contact (O1 .. Ow2, Ow1 .. O2)......         I Checked 
RESPONSE: The short contacts are hydrogen-bonding contacts. Analysis of the deltaF map didn?t 
allow to localized the water hydrogen atoms
;
_vrf_PLAT971_H2L2_2I3_2H2O       
;
PROBLEM: Check Calcd Residual Density (I3, I4, I5 and I6)......         I Checked 
RESPONSE: residual electron density remained at the end of refinements close to 
iodine atoms most likely due to series truncation errors
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H30 I6 N6 O4'
_chemical_formula_weight         1107.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.5053(6)
_cell_length_b                   13.5410(7)
_cell_length_c                   14.5928(9)
_cell_angle_alpha                99.590(5)
_cell_angle_beta                 102.045(6)
_cell_angle_gamma                94.974(5)
_cell_volume                     1418.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3099
_cell_measurement_theta_min      2.310
_cell_measurement_theta_max      23.97

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.593
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    6.598
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.08107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.4547
_diffrn_reflns_number            7992
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         24.052
_diffrn_reflns_theta_full        24.052
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             4334
_reflns_number_gt                3251
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data have been collected up to 0.87 Angstrom. Completeness at theta max was 96 %.
 The relative low resolution and completeness do not affect the final observed reflections/parameters ratio 
 (observed reflections/parameters ratio = 12).

 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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.8'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_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)+(0.1969P)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_number_reflns         4334
_refine_ls_number_parameters     271
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.1013
_refine_ls_wR_factor_ref         0.2694
_refine_ls_wR_factor_gt          0.2418
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C -0.163(3) 0.3433(16) 0.7495(13) 0.028(5) Uani 1 1 d . . . . .
H1C H -0.1676 0.3849 0.7012 0.034 Uiso 1 1 calc R U . . .
H1D H -0.2663 0.2904 0.7281 0.034 Uiso 1 1 calc R U . . .
C2 C -0.177(3) 0.4060(17) 0.8408(16) 0.032(5) Uani 1 1 d . . . . .
H2A H -0.2915 0.4352 0.8312 0.038 Uiso 1 1 calc R U . . .
H2B H -0.1793 0.3633 0.8879 0.038 Uiso 1 1 calc R U . . .
O1 O -0.028(2) 0.4850(12) 0.8764(11) 0.041(4) Uani 1 1 d . . . . .
C3 C 0.143(3) 0.4423(18) 0.8920(14) 0.035(5) Uani 1 1 d . . . . .
H3E H 0.1417 0.3987 0.9383 0.042 Uiso 1 1 calc R U . . .
H3F H 0.2432 0.4964 0.9185 0.042 Uiso 1 1 calc R U . . .
C4 C 0.178(3) 0.3807(18) 0.7995(16) 0.037(5) Uani 1 1 d . . . . .
H4A H 0.2913 0.3511 0.8130 0.045 Uiso 1 1 calc R U . . .
H4B H 0.1859 0.4236 0.7531 0.045 Uiso 1 1 calc R U . . .
N1 N 0.011(2) 0.2972(15) 0.7614(11) 0.030(4) Uani 1 1 d . . . . .
H1 H 0.0115 0.2528 0.8080 0.035 Uiso 1 1 calc R U . . .
C5 C 0.037(3) 0.2354(17) 0.6681(15) 0.034(5) Uani 1 1 d . . . . .
H5A H -0.0125 0.2664 0.6146 0.040 Uiso 1 1 calc R U . . .
H5B H 0.1665 0.2315 0.6708 0.040 Uiso 1 1 calc R U . . .
C6 C -0.062(3) 0.1338(17) 0.6573(16) 0.032(5) Uani 1 1 d . . . . .
H6G H -0.1927 0.1377 0.6485 0.039 Uiso 1 1 calc R U . . .
H6H H -0.0215 0.1066 0.7146 0.039 Uiso 1 1 calc R U . . .
C7 C -0.025(3) 0.0649(16) 0.5717(15) 0.030(5) Uani 1 1 d . . . . .
N2 N -0.030(2) -0.0361(14) 0.5743(13) 0.032(4) Uani 1 1 d . . . . .
N3 N -0.003(2) -0.0994(14) 0.5055(12) 0.030(4) Uani 1 1 d . . . . .
C8 C -0.207(3) 0.1185(16) 0.1956(14) 0.030(5) Uani 1 1 d . . . . .
H8C H -0.2092 0.0766 0.2432 0.036 Uiso 1 1 calc R U . . .
H8D H -0.3231 0.1460 0.1839 0.036 Uiso 1 1 calc R U . . .
C9 C -0.184(3) 0.0562(17) 0.1056(14) 0.026(5) Uani 1 1 d . . . . .
H9A H -0.2872 0.0034 0.0813 0.031 Uiso 1 1 calc R U . . .
H9B H -0.1821 0.0982 0.0580 0.031 Uiso 1 1 calc R U . . .
O2 O -0.0158(19) 0.0114(11) 0.1222(10) 0.030(3) Uani 1 1 d . . . . .
C10 C 0.140(3) 0.0911(16) 0.1530(14) 0.026(4) Uani 1 1 d . U . . .
H10E H 0.1403 0.1313 0.1039 0.031 Uiso 1 1 calc R U . . .
H10F H 0.2535 0.0612 0.1629 0.031 Uiso 1 1 calc R U . . .
C11 C 0.128(3) 0.1559(16) 0.2419(13) 0.026(5) Uani 1 1 d . . . . .
H11A H 0.2321 0.2081 0.2614 0.031 Uiso 1 1 calc R U . . .
H11B H 0.1339 0.1158 0.2915 0.031 Uiso 1 1 calc R U . . .
N4 N -0.048(2) 0.2054(14) 0.2330(12) 0.027(4) Uani 1 1 d . . . . .
H4 H -0.0509 0.2487 0.1853 0.032 Uiso 1 1 calc R U . . .
C12 C -0.069(3) 0.2662(17) 0.3223(15) 0.030(5) Uani 1 1 d . U . . .
H12C H -0.0336 0.2307 0.3744 0.036 Uiso 1 1 calc R U . . .
H12D H -0.1972 0.2765 0.3171 0.036 Uiso 1 1 calc R U . . .
C13 C 0.048(3) 0.3668(16) 0.3426(15) 0.030(5) Uani 1 1 d . . . . .
H13C H 0.1764 0.3560 0.3537 0.036 Uiso 1 1 calc R U . . .
H13D H 0.0211 0.3983 0.2871 0.036 Uiso 1 1 calc R U . . .
C14 C 0.018(3) 0.4360(15) 0.4266(12) 0.023(4) Uani 1 1 d . . . . .
N5 N 0.044(2) 0.5361(13) 0.4266(12) 0.026(4) Uani 1 1 d . . . . .
N6 N 0.026(2) 0.6005(14) 0.4991(12) 0.032(4) Uani 1 1 d . . . . .
I1 I 0.50357(17) 0.62605(9) 0.81273(8) 0.0232(4) Uani 1 1 d . . . . .
I2 I 0.46166(17) 0.48966(10) 0.62833(8) 0.0253(4) Uani 1 1 d . . . . .
I3 I -0.48613(17) 0.06746(10) 0.38373(8) 0.0237(4) Uani 1 1 d . . . . .
I4 I 0.54383(19) 0.75586(10) 0.99803(9) 0.0296(4) Uani 1 1 d . . . . .
I5 I -0.46765(18) -0.11898(10) 0.23246(9) 0.0265(4) Uani 1 1 d . . . . .
I6 I -0.51644(19) 0.24519(10) 0.50499(9) 0.0303(4) Uani 1 1 d . . . . .
OW1 O -0.0710(19) 0.1824(11) 0.9015(9) 0.028(3) Uani 1 1 d . . . . .
OW2 O -0.0219(19) 0.3073(11) 0.0886(9) 0.029(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.48(3) . ?
C1 N1 1.49(3) . ?
C2 O1 1.43(3) . ?
O1 C3 1.44(3) . ?
C3 C4 1.55(3) . ?
C4 N1 1.55(3) . ?
N1 C5 1.53(3) . ?
C5 C6 1.47(3) . ?
C6 C7 1.52(3) . ?
C7 N3 1.34(3) 2_556 ?
C7 N2 1.37(3) . ?
N2 N3 1.27(3) . ?
N3 C7 1.34(3) 2_556 ?
C8 C9 1.49(3) . ?
C8 N4 1.54(3) . ?
C9 O2 1.44(2) . ?
O2 C10 1.46(2) . ?
C10 C11 1.46(3) . ?
C11 N4 1.52(3) . ?
N4 C12 1.47(3) . ?
C12 C13 1.51(3) . ?
C13 C14 1.48(3) . ?
C14 N5 1.35(3) . ?
C14 N6 1.35(2) 2_566 ?
N5 N6 1.29(3) . ?
N6 C14 1.35(2) 2_566 ?
I1 I4 2.9114(17) . ?
I1 I2 2.9396(16) . ?
I3 I6 2.7963(18) . ?
I3 I5 3.0979(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 110.8(16) . . ?
O1 C2 C1 112.1(17) . . ?
C2 O1 C3 109.6(17) . . ?
O1 C3 C4 112.8(17) . . ?
C3 C4 N1 105.6(16) . . ?
C1 N1 C5 113.0(16) . . ?
C1 N1 C4 110.1(17) . . ?
C5 N1 C4 107.7(15) . . ?
C6 C5 N1 106.8(16) . . ?
C5 C6 C7 109.6(16) . . ?
N3 C7 N2 120.5(19) 2_556 . ?
N3 C7 C6 122.0(18) 2_556 . ?
N2 C7 C6 117.4(17) . . ?
N3 N2 C7 121.8(18) . . ?
N2 N3 C7 117.7(18) . 2_556 ?
C9 C8 N4 110.2(16) . . ?
O2 C9 C8 110.5(16) . . ?
C9 O2 C10 109.4(15) . . ?
O2 C10 C11 110.1(16) . . ?
C10 C11 N4 113.1(16) . . ?
C12 N4 C11 114.4(15) . . ?
C12 N4 C8 110.3(15) . . ?
C11 N4 C8 105.9(16) . . ?
N4 C12 C13 110.0(17) . . ?
C14 C13 C12 112.6(17) . . ?
N5 C14 N6 122.2(17) . 2_566 ?
N5 C14 C13 117.0(17) . . ?
N6 C14 C13 120.8(18) 2_566 . ?
N6 N5 C14 120.0(16) . . ?
N5 N6 C14 117.8(18) . 2_566 ?
I4 I1 I2 178.28(6) . . ?
I6 I3 I5 174.25(6) . . ?

_refine_diff_density_max         4.447
_refine_diff_density_min         -3.765
_refine_diff_density_rms         0.679

####################################################################### 
# 
# 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_2H2L2_3I3_I_4H2O
_database_code_depnum_ccdc_archive 'CCDC 1518137'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_2H2L_3I3_I_4H2O     
;
PROBLEM: Check Calcd Residual Density ...... (I4, I2, I5, I6, I1, I10 and I3)        I Checked 
RESPONSE: residual electron density remained at the end of refinements close to 
iodine atoms most likely due to series truncation errors.
;
_vrf_PLAT214_2H2L2_3I3_I_4H2O    
;
PROBLEM: Atom Ow2 (Anion/Solvent) ADP max/min Ratio ......         I Checked 
RESPONSE: This oxygen atom belongs to a cocrystallized water molecule most likely affected by positional disorder.
Nevertheless, analysis of the principal mean square atomic displacements U didn't allow to split on different positions
;
_vrf_PLAT306_2H2L2_3I3_I_4H2O    
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) (OW1 and OW2)......         I Checked 
RESPONSE: Analysis of the deltaF map didn?t allow to localized the water hydrogen atoms
;
_vrf_PLAT430_2H2L2_3I3_I_4H2O    
;
PROBLEM: Short Inter D...A Contact (O1 .. Ow2, Ow1 .. O2, Ow1 .. Ow2)......         I Checked 
RESPONSE: The short contacts are hydrogen-bonding contacts. Analysis of the deltaF map didn?t 
allow to localized the water hydrogen atoms
;
_vrf_PLAT971_2H2L2_3I3_I_4H2O    
;
PROBLEM: Check Calcd Residual Density (I2, I4, I6 and I3)......         I Checked 
RESPONSE: residual electron density remained at the end of refinements close to 
iodine atoms most likely due to series truncation errors
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H34 I5 N6 O4'
_chemical_formula_weight         984.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3403(3)
_cell_length_b                   14.3161(2)
_cell_length_c                   13.8619(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.228(2)
_cell_angle_gamma                90
_cell_volume                     2732.42(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5916
_cell_measurement_theta_min      2.077
_cell_measurement_theta_max      26.026

_exptl_crystal_description       prismatic
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.394
_exptl_crystal_F_000             1828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    5.721
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.01579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.4547
_diffrn_reflns_number            17772
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_av_R_equivalents  0.1171
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.052
_diffrn_reflns_theta_max         26.058
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5256
_reflns_number_gt                3668
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.8'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_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)+(0.1241P)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_number_reflns         5256
_refine_ls_number_parameters     268
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.2057
_refine_ls_wR_factor_gt          0.1709
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
I10 I -0.5000 0.5000 0.5000 0.0439(4) Uani 1 2 d S . P . .
I1 I 0.21011(6) 0.02452(5) 0.03673(6) 0.0297(3) Uani 1 1 d . . . . .
I2 I -0.01035(6) 0.01638(5) 0.28655(6) 0.0261(2) Uani 1 1 d . . . . .
I3 I 0.29913(6) -0.01947(6) 0.51028(7) 0.0307(3) Uani 1 1 d . . . . .
I4 I 0.0000 0.0000 0.5000 0.0190(3) Uani 1 2 d S . P . .
I5 I 0.0000 0.0000 0.0000 0.0269(3) Uani 1 2 d S . P . .
I6 I 0.5000 0.0000 0.5000 0.0295(3) Uani 1 2 d S . P . .
O2 O 0.4003(5) 0.7543(5) 0.1841(7) 0.0242(19) Uani 1 1 d . . . . .
C8 C -0.0583(7) 0.7610(7) 0.5222(9) 0.015(2) Uani 1 1 d . . . . .
N5 N 0.1034(6) 0.7380(6) 0.5580(8) 0.017(2) Uani 1 1 d . . . . .
N4 N 0.0266(6) 0.7502(6) 0.5920(7) 0.0149(18) Uani 1 1 d . U . . .
C6 C 0.1772(8) 0.7174(9) 0.4208(11) 0.032(3) Uani 1 1 d . . . . .
H6A H 0.1771 0.6523 0.4014 0.038 Uiso 1 1 calc R U . . .
H6B H 0.2355 0.7285 0.4753 0.038 Uiso 1 1 calc R U . . .
N2 N -0.0719(6) 0.7593(6) 0.4224(8) 0.017(2) Uani 1 1 d . . . . .
C7 C 0.0904(7) 0.7365(7) 0.4564(8) 0.0110(19) Uani 1 1 d . U . . .
N6 N 0.2765(5) 0.7720(6) 0.3128(7) 0.0169(19) Uani 1 1 d . . . . .
H6 H 0.3257 0.7789 0.3776 0.020 Uiso 1 1 calc R U . . .
C5 C 0.1788(7) 0.7787(8) 0.3320(9) 0.020(2) Uani 1 1 d . . . . .
H5A H 0.1287 0.7586 0.2729 0.025 Uiso 1 1 calc R U . . .
H5B H 0.1658 0.8430 0.3461 0.025 Uiso 1 1 calc R U . . .
C10 C -0.1460(7) 0.7244(8) 0.6511(9) 0.017(2) Uani 1 1 d . . . . .
H10A H -0.1293 0.6597 0.6436 0.021 Uiso 1 1 calc R U . . .
H10B H -0.0972 0.7506 0.7077 0.021 Uiso 1 1 calc R U . . .
N3 N 0.0045(6) 0.7466(6) 0.3895(7) 0.017(2) Uani 1 1 d . . . . .
O1 O -0.3678(5) 0.7446(5) 0.7988(7) 0.0205(17) Uani 1 1 d . . . . .
C3 C 0.2933(7) 0.6789(8) 0.2693(9) 0.021(2) Uani 1 1 d . . . . .
H3A H 0.2426 0.6678 0.2074 0.025 Uiso 1 1 calc R U . . .
H3B H 0.2903 0.6295 0.3162 0.025 Uiso 1 1 calc R U . . .
C1 C 0.2916(7) 0.8493(8) 0.2461(9) 0.021(2) Uani 1 1 d . . . . .
H1A H 0.2867 0.9091 0.2774 0.025 Uiso 1 1 calc R U . . .
H1B H 0.2414 0.8468 0.1826 0.025 Uiso 1 1 calc R U . . .
C12 C -0.3602(7) 0.6582(8) 0.7511(10) 0.023(3) Uani 1 1 d . . . . .
H12A H -0.4101 0.6549 0.6874 0.027 Uiso 1 1 calc R U . . .
H12B H -0.3706 0.6072 0.7929 0.027 Uiso 1 1 calc R U . . .
N1 N -0.2447(6) 0.7295(6) 0.6706(7) 0.0121(17) Uani 1 1 d . U . . .
H1 H -0.2940 0.7255 0.6055 0.015 Uiso 1 1 calc R U . . .
C14 C -0.2581(7) 0.8202(7) 0.7172(9) 0.019(2) Uani 1 1 d . . . . .
H14A H -0.2535 0.8712 0.6726 0.023 Uiso 1 1 calc R U . . .
H14B H -0.2078 0.8283 0.7799 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3916(7) 0.6770(8) 0.2482(10) 0.025(3) Uani 1 1 d . . . . .
H4A H 0.4427 0.6808 0.3110 0.030 Uiso 1 1 calc R U . . .
H4B H 0.3992 0.6186 0.2157 0.030 Uiso 1 1 calc R U . . .
C9 C -0.1477(7) 0.7785(7) 0.5558(8) 0.013(2) Uani 1 1 d . . . . .
H9A H -0.2046 0.7604 0.5025 0.016 Uiso 1 1 calc R U . . .
H9B H -0.1527 0.8448 0.5680 0.016 Uiso 1 1 calc R U . . .
C13 C -0.3584(7) 0.8208(8) 0.7366(10) 0.023(2) Uani 1 1 d . . . . .
H13A H -0.3671 0.8790 0.7689 0.027 Uiso 1 1 calc R U . . .
H13B H -0.4086 0.8169 0.6732 0.027 Uiso 1 1 calc R U . . .
C11 C -0.2595(7) 0.6480(8) 0.7329(9) 0.019(2) Uani 1 1 d . . . . .
H11A H -0.2093 0.6472 0.7965 0.022 Uiso 1 1 calc R U . . .
H11B H -0.2561 0.5899 0.6980 0.022 Uiso 1 1 calc R U . . .
C2 C 0.3894(7) 0.8410(8) 0.2277(9) 0.020(2) Uani 1 1 d . . . . .
H2A H 0.3974 0.8909 0.1834 0.024 Uiso 1 1 calc R U . . .
H2B H 0.4395 0.8477 0.2908 0.024 Uiso 1 1 calc R U . . .
OW1 O 0.4208(5) 0.7536(6) -0.0081(7) 0.030(2) Uani 1 1 d . . . . .
OW2 O -0.3874(6) 0.7329(12) 0.4906(8) 0.076(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I5 2.9331(9) . ?
I2 I4 2.9302(9) . ?
I3 I6 2.9369(9) . ?
I4 I2 2.9302(9) 3_556 ?
I5 I1 2.9331(9) 3 ?
I6 I3 2.9368(9) 3_656 ?
O2 C2 1.407(14) . ?
O2 C4 1.446(15) . ?
C8 N2 1.342(16) . ?
C8 N4 1.336(13) . ?
C8 C9 1.502(13) . ?
N5 N4 1.324(13) . ?
N5 C7 1.368(15) . ?
C6 C7 1.488(14) . ?
C6 C5 1.517(17) . ?
N2 N3 1.311(13) . ?
C7 N3 1.326(13) . ?
N6 C1 1.496(14) . ?
N6 C5 1.500(12) . ?
N6 C3 1.510(14) . ?
C10 N1 1.514(12) . ?
C10 C9 1.526(15) . ?
O1 C12 1.420(14) . ?
O1 C13 1.420(14) . ?
C3 C4 1.518(15) . ?
C1 C2 1.498(15) . ?
C12 C11 1.541(14) . ?
N1 C14 1.486(14) . ?
N1 C11 1.502(14) . ?
C14 C13 1.536(14) . ?

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
I2 I4 I2 180.0 3_556 . ?
I1 I5 I1 180.0 3 . ?
I3 I6 I3 180.0 3_656 . ?
C2 O2 C4 111.8(9) . . ?
N2 C8 N4 125.8(10) . . ?
N2 C8 C9 115.6(8) . . ?
N4 C8 C9 118.6(10) . . ?
N4 N5 C7 118.7(8) . . ?
N5 N4 C8 116.0(10) . . ?
C7 C6 C5 111.4(9) . . ?
N3 N2 C8 117.8(8) . . ?
N3 C7 N5 123.5(9) . . ?
N3 C7 C6 119.2(10) . . ?
N5 C7 C6 117.2(9) . . ?
C1 N6 C5 111.5(8) . . ?
C1 N6 C3 109.8(9) . . ?
C5 N6 C3 112.9(8) . . ?
N6 C5 C6 109.4(9) . . ?
N1 C10 C9 109.9(8) . . ?
N2 N3 C7 118.3(10) . . ?
C12 O1 C13 110.8(9) . . ?
N6 C3 C4 110.7(9) . . ?
N6 C1 C2 110.5(9) . . ?
O1 C12 C11 110.8(8) . . ?
C14 N1 C11 111.8(8) . . ?
C14 N1 C10 111.2(8) . . ?
C11 N1 C10 110.7(8) . . ?
N1 C14 C13 108.8(8) . . ?
O2 C4 C3 110.4(9) . . ?
C8 C9 C10 112.1(8) . . ?
O1 C13 C14 110.7(9) . . ?
N1 C11 C12 108.0(8) . . ?
O2 C2 C1 111.5(9) . . ?

_refine_diff_density_max         2.895
_refine_diff_density_min         -3.840
_refine_diff_density_rms         0.437

