# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shrv307
_database_code_depnum_ccdc_archive 'CCDC 1424001'
_audit_update_record             
;
2015-09-12 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5
_chemical_name_common            5
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 I2 N7 O4'
_chemical_formula_sum            'C8 H5 I2 N7 O4'
_chemical_formula_weight         516.99

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'
I I -0.3257 6.8362 '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                   16.6797(6)
_cell_length_b                   8.9136(3)
_cell_length_c                   9.1213(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.956(2)
_cell_angle_gamma                90
_cell_volume                     1339.59(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2729
_cell_measurement_theta_min      5.37
_cell_measurement_theta_max      68.50

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.563
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    37.190
_shelx_estimated_absorpt_T_min   0.048
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.5155
_exptl_absorpt_correction_T_max  0.7531

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7543
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         68.705
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2389
_reflns_number_gt                1769
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0343P)²+0.2369P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2389
_refine_ls_number_parameters     193
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
I1 I 0.48846(2) 0.63007(4) 1.23653(4) 0.02233(13) Uani 1 1 d . . . . .
C2 C 0.4002(4) 0.7415(6) 1.0915(6) 0.0206(14) Uani 1 1 d . . . . .
N3 N 0.3906(3) 0.8887(5) 1.0986(5) 0.0202(12) Uani 1 1 d . . . . .
N4 N 0.3282(3) 0.9235(5) 0.9836(5) 0.0163(11) Uani 1 1 d . . . . .
C5 C 0.2938(4) 1.0735(6) 0.9722(6) 0.0256(16) Uani 1 1 d . . . . .
H5A H 0.3281 1.1408 1.0421 0.031 Uiso 1 1 calc R U . . .
H5B H 0.2390 1.0708 1.0012 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2878(4) 1.1354(6) 0.8171(6) 0.0287(16) Uani 1 1 d . . . . .
H6A H 0.2740 1.2434 0.8183 0.034 Uiso 1 1 calc R U . . .
H6B H 0.3412 1.1260 0.7836 0.034 Uiso 1 1 calc R U . . .
N7 N 0.2268(3) 1.0583(6) 0.7124(5) 0.0219(13) Uani 1 1 d . . . . .
N8 N 0.1840(3) 1.1439(5) 0.5985(5) 0.0232(12) Uani 1 1 d . . . . .
C9 C 0.1386(4) 1.0475(7) 0.5135(6) 0.0242(15) Uani 1 1 d . . . . .
I10 I 0.06316(3) 1.12694(5) 0.32801(4) 0.02983(15) Uani 1 1 d . . . . .
C11 C 0.1508(4) 0.9021(6) 0.5688(6) 0.0185(13) Uani 1 1 d . . . . .
N12 N 0.1185(3) 0.7651(6) 0.5081(5) 0.0243(12) Uani 1 1 d . . . . .
O13 O 0.0672(3) 0.7677(5) 0.3956(5) 0.0364(12) Uani 1 1 d . . . . .
O14 O 0.1451(3) 0.6462(4) 0.5688(4) 0.0274(11) Uani 1 1 d . . . . .
C15 C 0.2076(4) 0.9144(6) 0.6966(6) 0.0163(13) Uani 1 1 d . . . . .
N16 N 0.2410(3) 0.7980(5) 0.7868(5) 0.0164(11) Uani 1 1 d D . . . .
H16 H 0.221(3) 0.710(3) 0.764(6) 0.020 Uiso 1 1 d D U . . .
C17 C 0.3003(4) 0.8003(6) 0.9072(6) 0.0151(13) Uani 1 1 d . . . . .
C18 C 0.3446(4) 0.6792(6) 0.9738(6) 0.0174(13) Uani 1 1 d . . . . .
N19 N 0.3304(3) 0.5284(5) 0.9316(5) 0.0173(11) Uani 1 1 d . . . . .
O20 O 0.2790(3) 0.5040(4) 0.8195(4) 0.0229(10) Uani 1 1 d . . . . .
O21 O 0.3672(3) 0.4280(4) 1.0052(4) 0.0268(11) 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 C2 2.072(6) . ?
C2 N3 1.325(7) . ?
C2 C18 1.419(8) . ?
N3 N4 1.393(6) . ?
N4 C17 1.344(7) . ?
N4 C5 1.452(7) . ?
C5 C6 1.507(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.454(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C15 1.325(7) . ?
N7 N8 1.392(6) . ?
N8 C9 1.315(8) . ?
C9 C11 1.394(8) . ?
C9 I10 2.070(6) . ?
C11 C15 1.387(7) . ?
C11 N12 1.412(7) . ?
N12 O13 1.230(6) . ?
N12 O14 1.244(6) . ?
C15 N16 1.387(7) . ?
N16 C17 1.359(7) . ?
N16 H16 0.867(10) . ?
C17 C18 1.393(8) . ?
C18 N19 1.408(7) . ?
N19 O21 1.225(6) . ?
N19 O20 1.247(6) . ?

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
N3 C2 C18 110.8(5) . . ?
N3 C2 I1 121.5(4) . . ?
C18 C2 I1 127.7(4) . . ?
C2 N3 N4 105.4(4) . . ?
C17 N4 N3 111.5(4) . . ?
C17 N4 C5 127.9(5) . . ?
N3 N4 C5 120.0(4) . . ?
N4 C5 C6 111.9(5) . . ?
N4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N7 C6 C5 112.4(5) . . ?
N7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C15 N7 N8 111.2(5) . . ?
C15 N7 C6 131.4(5) . . ?
N8 N7 C6 117.1(5) . . ?
C9 N8 N7 105.2(5) . . ?
N8 C9 C11 110.9(5) . . ?
N8 C9 I10 118.6(4) . . ?
C11 C9 I10 130.5(5) . . ?
C15 C11 C9 105.8(5) . . ?
C15 C11 N12 124.5(5) . . ?
C9 C11 N12 129.6(5) . . ?
O13 N12 O14 122.7(5) . . ?
O13 N12 C11 118.9(5) . . ?
O14 N12 C11 118.3(5) . . ?
N7 C15 N16 126.3(5) . . ?
N7 C15 C11 106.9(5) . . ?
N16 C15 C11 126.8(5) . . ?
C17 N16 C15 130.0(5) . . ?
C17 N16 H16 114(4) . . ?
C15 N16 H16 116(4) . . ?
N4 C17 N16 125.5(5) . . ?
N4 C17 C18 106.8(5) . . ?
N16 C17 C18 127.6(5) . . ?
C17 C18 N19 124.4(5) . . ?
C17 C18 C2 105.5(5) . . ?
N19 C18 C2 130.0(5) . . ?
O21 N19 O20 122.9(5) . . ?
O21 N19 C18 119.9(5) . . ?
O20 N19 C18 117.1(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
C18 C2 N3 N4 -0.3(7) . . . . ?
I1 C2 N3 N4 178.6(4) . . . . ?
C2 N3 N4 C17 -0.2(6) . . . . ?
C2 N3 N4 C5 171.1(5) . . . . ?
C17 N4 C5 C6 -58.5(8) . . . . ?
N3 N4 C5 C6 131.7(6) . . . . ?
N4 C5 C6 N7 69.4(7) . . . . ?
C5 C6 N7 C15 -40.7(9) . . . . ?
C5 C6 N7 N8 145.5(5) . . . . ?
C15 N7 N8 C9 -0.2(7) . . . . ?
C6 N7 N8 C9 174.8(5) . . . . ?
N7 N8 C9 C11 0.0(7) . . . . ?
N7 N8 C9 I10 179.7(4) . . . . ?
N8 C9 C11 C15 0.1(7) . . . . ?
I10 C9 C11 C15 -179.5(5) . . . . ?
N8 C9 C11 N12 -175.7(6) . . . . ?
I10 C9 C11 N12 4.7(10) . . . . ?
C15 C11 N12 O13 178.6(6) . . . . ?
C9 C11 N12 O13 -6.2(10) . . . . ?
C15 C11 N12 O14 -3.2(9) . . . . ?
C9 C11 N12 O14 171.9(6) . . . . ?
N8 N7 C15 N16 177.4(5) . . . . ?
C6 N7 C15 N16 3.3(10) . . . . ?
N8 N7 C15 C11 0.3(7) . . . . ?
C6 N7 C15 C11 -173.8(6) . . . . ?
C9 C11 C15 N7 -0.3(7) . . . . ?
N12 C11 C15 N7 175.9(5) . . . . ?
C9 C11 C15 N16 -177.3(6) . . . . ?
N12 C11 C15 N16 -1.2(10) . . . . ?
N7 C15 N16 C17 -1.2(10) . . . . ?
C11 C15 N16 C17 175.3(6) . . . . ?
N3 N4 C17 N16 -178.3(5) . . . . ?
C5 N4 C17 N16 11.2(9) . . . . ?
N3 N4 C17 C18 0.7(6) . . . . ?
C5 N4 C17 C18 -169.9(6) . . . . ?
C15 N16 C17 N4 14.6(10) . . . . ?
C15 N16 C17 C18 -164.1(6) . . . . ?
N4 C17 C18 N19 176.1(5) . . . . ?
N16 C17 C18 N19 -5.0(10) . . . . ?
N4 C17 C18 C2 -0.8(6) . . . . ?
N16 C17 C18 C2 178.1(6) . . . . ?
N3 C2 C18 C17 0.7(7) . . . . ?
I1 C2 C18 C17 -178.1(4) . . . . ?
N3 C2 C18 N19 -176.0(6) . . . . ?
I1 C2 C18 N19 5.2(10) . . . . ?
C17 C18 N19 O21 -173.1(6) . . . . ?
C2 C18 N19 O21 3.0(9) . . . . ?
C17 C18 N19 O20 6.1(8) . . . . ?
C2 C18 N19 O20 -177.8(6) . . . . ?

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
C6 H6A O20 0.99 2.32 3.289(7) 164.5 1_565
N16 H16 O14 0.867(10) 2.09(5) 2.712(6) 128(5) .
N16 H16 O20 0.867(10) 2.10(5) 2.701(6) 126(5) .

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.150


# start Validation Reply Form
_vrf_PLAT015_shrv307             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinley not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form_exptl_crystal_recrystallization_method 
####################################################################### 
# 
# 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_shrv334
_database_code_depnum_ccdc_archive 'CCDC 1424002'
_audit_update_record             
;
2015-09-12 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        10
_chemical_name_common            10
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H2 I2 N4 O4, C2 H6 O S'
_chemical_formula_sum            'C9 H8 I2 N4 O5 S'
_chemical_formula_weight         538.05


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'
S S 0.1246 0.1234 '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                   5.34160(10)
_cell_length_b                   25.7684(6)
_cell_length_c                   11.3694(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.2720(10)
_cell_angle_gamma                90
_cell_volume                     1552.35(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4429
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      26.11

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.302
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    4.211
_shelx_estimated_absorpt_T_min   0.625
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6221
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14724
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.613
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3168
_reflns_number_gt                2566
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0713P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_restrained_S_all      0.827
_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 0.9849(9) 0.20482(18) 0.1657(4) 0.0435(11) Uani 1 1 d . . . . .
H1 H 1.0188 0.1706 0.1473 0.052 Uiso 1 1 calc R U . . .
N2 N 0.8286(8) 0.21795(14) 0.2453(4) 0.0367(8) Uani 1 1 d . . . . .
C3 C 0.8260(8) 0.27071(16) 0.2511(4) 0.0310(9) Uani 1 1 d . . . . .
C4 C 0.7127(8) 0.30547(17) 0.3222(4) 0.0329(9) Uani 1 1 d . . . . .
I5 I 0.46144(5) 0.27948(2) 0.43728(2) 0.04016(12) Uani 1 1 d . . . . .
C6 C 0.7704(8) 0.35666(16) 0.3082(4) 0.0330(9) Uani 1 1 d . . . . .
N7 N 0.6673(8) 0.39585(15) 0.3842(4) 0.0427(9) Uani 1 1 d . . . . .
O8 O 0.7556(8) 0.39600(17) 0.4880(3) 0.0707(12) Uani 1 1 d . . . . .
O9 O 0.5035(7) 0.42394(16) 0.3381(4) 0.0666(11) Uani 1 1 d . . . . .
C10 C 0.9176(8) 0.37454(17) 0.2217(4) 0.0332(9) Uani 1 1 d . . . . .
N11 N 0.9516(7) 0.43101(15) 0.2100(4) 0.0423(9) Uani 1 1 d . . . . .
O12 O 1.0009(7) 0.45574(13) 0.3011(4) 0.0599(10) Uani 1 1 d . . . . .
O13 O 0.9320(8) 0.44908(14) 0.1131(4) 0.0691(11) Uani 1 1 d . . . . .
C14 C 1.0267(8) 0.33990(17) 0.1493(4) 0.0317(9) Uani 1 1 d . . . . .
I15 I 1.25395(6) 0.35944(2) 0.01888(3) 0.04248(12) Uani 1 1 d . . . . .
C16 C 0.9885(8) 0.28738(16) 0.1695(4) 0.0305(9) Uani 1 1 d . . . . .
N17 N 1.0855(7) 0.24487(14) 0.1163(4) 0.0390(8) Uani 1 1 d . . . . .
S1S S 0.6028(2) 0.08326(5) 0.25231(12) 0.0491(3) Uani 1 1 d . . . . .
O4S O 0.5391(9) 0.13291(13) 0.3119(4) 0.0677(12) Uani 1 1 d . . . . .
C3S C 0.5716(14) 0.0328(2) 0.3548(6) 0.0721(17) Uani 1 1 d . . . . .
H3S1 H 0.7043 0.0355 0.4199 0.108 Uiso 1 1 calc R U . . .
H3S2 H 0.5825 -0.0001 0.3164 0.108 Uiso 1 1 calc R U . . .
H3S3 H 0.4111 0.0357 0.3839 0.108 Uiso 1 1 calc R U . . .
C2S C 0.3355(12) 0.0668(3) 0.1489(6) 0.0722(17) Uani 1 1 d . . . . .
H2S1 H 0.1865 0.0673 0.1881 0.108 Uiso 1 1 calc R U . . .
H2S2 H 0.3581 0.0327 0.1178 0.108 Uiso 1 1 calc R U . . .
H2S3 H 0.3180 0.0915 0.0852 0.108 Uiso 1 1 calc R U . . .
H2 H 0.735(13) 0.196(3) 0.271(6) 0.087 Uiso 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 N17 1.322(6) . ?
C1 N2 1.349(6) . ?
C1 H1 0.9300 . ?
N2 C3 1.361(5) . ?
N2 H2 0.83(7) . ?
C3 C4 1.395(6) . ?
C3 C16 1.415(6) . ?
C4 C6 1.369(6) . ?
C4 I5 2.099(4) . ?
C6 C10 1.412(6) . ?
C6 N7 1.480(6) . ?
N7 O9 1.203(5) . ?
N7 O8 1.214(5) . ?
C10 C14 1.391(6) . ?
C10 N11 1.474(6) . ?
N11 O13 1.188(5) . ?
N11 O12 1.217(5) . ?
C14 C16 1.392(6) . ?
C14 I15 2.093(4) . ?
C16 N17 1.383(5) . ?
S1S O4S 1.507(4) . ?
S1S C3S 1.768(6) . ?
S1S C2S 1.782(6) . ?
C3S H3S1 0.9600 . ?
C3S H3S2 0.9600 . ?
C3S H3S3 0.9600 . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 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
N17 C1 N2 114.1(4) . . ?
N17 C1 H1 122.9 . . ?
N2 C1 H1 122.9 . . ?
C1 N2 C3 107.1(4) . . ?
C1 N2 H2 121(5) . . ?
C3 N2 H2 130(5) . . ?
N2 C3 C4 132.6(4) . . ?
N2 C3 C16 105.1(4) . . ?
C4 C3 C16 122.1(4) . . ?
C6 C4 C3 115.5(4) . . ?
C6 C4 I5 123.5(3) . . ?
C3 C4 I5 121.0(3) . . ?
C4 C6 C10 123.3(4) . . ?
C4 C6 N7 118.9(4) . . ?
C10 C6 N7 117.7(4) . . ?
O9 N7 O8 126.4(4) . . ?
O9 N7 C6 117.4(4) . . ?
O8 N7 C6 116.2(4) . . ?
C14 C10 C6 121.0(4) . . ?
C14 C10 N11 120.9(4) . . ?
C6 C10 N11 118.1(4) . . ?
O13 N11 O12 124.6(4) . . ?
O13 N11 C10 118.2(4) . . ?
O12 N11 C10 117.1(4) . . ?
C10 C14 C16 116.4(4) . . ?
C10 C14 I15 126.1(3) . . ?
C16 C14 I15 117.5(3) . . ?
N17 C16 C14 128.8(4) . . ?
N17 C16 C3 110.0(4) . . ?
C14 C16 C3 121.2(4) . . ?
C1 N17 C16 103.7(4) . . ?
O4S S1S C3S 106.4(3) . . ?
O4S S1S C2S 106.9(3) . . ?
C3S S1S C2S 97.2(3) . . ?
S1S C3S H3S1 109.5 . . ?
S1S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
S1S C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?
S1S C2S H2S1 109.5 . . ?
S1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
S1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 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
N17 C1 N2 C3 -0.8(6) . . . . ?
C1 N2 C3 C4 -175.4(5) . . . . ?
C1 N2 C3 C16 0.4(5) . . . . ?
N2 C3 C4 C6 175.0(5) . . . . ?
C16 C3 C4 C6 -0.3(6) . . . . ?
N2 C3 C4 I5 -7.2(7) . . . . ?
C16 C3 C4 I5 177.5(3) . . . . ?
C3 C4 C6 C10 4.9(6) . . . . ?
I5 C4 C6 C10 -172.9(3) . . . . ?
C3 C4 C6 N7 -177.2(4) . . . . ?
I5 C4 C6 N7 4.9(6) . . . . ?
C4 C6 N7 O9 -108.5(5) . . . . ?
C10 C6 N7 O9 69.5(6) . . . . ?
C4 C6 N7 O8 70.7(6) . . . . ?
C10 C6 N7 O8 -111.3(5) . . . . ?
C4 C6 C10 C14 -4.0(7) . . . . ?
N7 C6 C10 C14 178.2(4) . . . . ?
C4 C6 C10 N11 175.8(4) . . . . ?
N7 C6 C10 N11 -2.1(6) . . . . ?
C14 C10 N11 O13 43.7(6) . . . . ?
C6 C10 N11 O13 -136.0(5) . . . . ?
C14 C10 N11 O12 -135.5(4) . . . . ?
C6 C10 N11 O12 44.8(6) . . . . ?
C6 C10 C14 C16 -1.8(6) . . . . ?
N11 C10 C14 C16 178.4(4) . . . . ?
C6 C10 C14 I15 -179.0(3) . . . . ?
N11 C10 C14 I15 1.3(6) . . . . ?
C10 C14 C16 N17 -175.9(4) . . . . ?
I15 C14 C16 N17 1.5(6) . . . . ?
C10 C14 C16 C3 6.3(6) . . . . ?
I15 C14 C16 C3 -176.3(3) . . . . ?
N2 C3 C16 N17 0.0(5) . . . . ?
C4 C3 C16 N17 176.4(4) . . . . ?
N2 C3 C16 C14 178.2(4) . . . . ?
C4 C3 C16 C14 -5.4(6) . . . . ?
N2 C1 N17 C16 0.8(5) . . . . ?
C14 C16 N17 C1 -178.5(4) . . . . ?
C3 C16 N17 C1 -0.5(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
C3S H3S1 O13 0.96 2.41 3.334(9) 162.6 4_566
N2 H2 O4S 0.83(7) 2.02(7) 2.840(5) 168(7) .

_refine_diff_density_max         0.855
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.096

# start Validation Reply Form
_vrf_PLAT015_shrv334             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
_vrf_PLAT430_shrv334             
;
PROBLEM: Short Inter D...A Contact  O9     ..  O12     ..       2.79 Ang.  
RESPONSE: High density energetic materials often display close contacts.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_shrv328
_database_code_depnum_ccdc_archive 'CCDC 1424003'
_audit_update_record             
;
2015-09-12 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        14
_chemical_name_common            14
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H2 N6 O9, C4 H8 O2'
_chemical_formula_sum            'C11 H10 N6 O11'
_chemical_formula_weight         402.25

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'

_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                   7.8304(7)
_cell_length_b                   9.3182(8)
_cell_length_c                   12.2176(11)
_cell_angle_alpha                102.459(3)
_cell_angle_beta                 104.030(3)
_cell_angle_gamma                100.776(3)
_cell_volume                     817.12(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2912
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      26.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6848
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7885
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.506
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3321
_reflns_number_gt                2534
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0605P)²+0.1904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3321
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
O1 O 0.14117(18) -0.05141(14) -0.08777(12) 0.0539(4) Uani 1 1 d . . . . .
C2 C 0.2400(2) 0.06994(19) -0.02491(15) 0.0383(4) Uani 1 1 d . . . . .
N3 N 0.40720(19) 0.14030(15) -0.03215(13) 0.0368(3) Uani 1 1 d . . . . .
H3 H 0.453(3) 0.104(2) -0.0874(18) 0.044 Uiso 1 1 d . U . . .
C4 C 0.4796(2) 0.27346(17) 0.05395(13) 0.0318(3) Uani 1 1 d . . . . .
C5 C 0.6408(2) 0.38294(18) 0.08616(14) 0.0335(4) Uani 1 1 d . . . . .
N6 N 0.7756(2) 0.36174(16) 0.02227(14) 0.0425(4) Uani 1 1 d . . . . .
O7 O 0.93452(18) 0.40062(17) 0.07906(13) 0.0562(4) Uani 1 1 d . . . . .
O8 O 0.7162(2) 0.3052(2) -0.08139(14) 0.0841(6) Uani 1 1 d . . . . .
C9 C 0.6779(2) 0.50759(18) 0.18368(14) 0.0349(4) Uani 1 1 d . . . . .
N10 N 0.8427(2) 0.63216(16) 0.21392(14) 0.0439(4) Uani 1 1 d . . . . .
O11 O 0.8655(2) 0.68806(16) 0.13585(14) 0.0635(4) Uani 1 1 d . . . . .
O12 O 0.9400(2) 0.67050(19) 0.31425(14) 0.0717(5) Uani 1 1 d . . . . .
C13 C 0.5571(2) 0.52026(18) 0.24820(14) 0.0358(4) Uani 1 1 d . . . . .
N14 N 0.6057(2) 0.64986(18) 0.35416(15) 0.0506(4) Uani 1 1 d . . . . .
O15 O 0.6180(2) 0.77474(16) 0.33823(16) 0.0778(5) Uani 1 1 d . . . . .
O16 O 0.6339(3) 0.6199(2) 0.44707(14) 0.0770(5) Uani 1 1 d . . . . .
C17 C 0.3919(2) 0.41004(18) 0.21636(14) 0.0341(4) Uani 1 1 d . . . . .
N18 N 0.2585(2) 0.42510(18) 0.28111(13) 0.0435(4) Uani 1 1 d . . . . .
O19 O 0.2597(2) 0.55111(18) 0.33281(16) 0.0772(5) Uani 1 1 d . . . . .
O20 O 0.1528(2) 0.30926(17) 0.27514(13) 0.0619(4) Uani 1 1 d . . . . .
C21 C 0.3529(2) 0.28735(17) 0.11966(13) 0.0316(3) Uani 1 1 d . . . . .
N22 N 0.2092(2) 0.16403(15) 0.06825(12) 0.0357(3) Uani 1 1 d . . . . .
H22 H 0.115(3) 0.141(2) 0.0869(17) 0.043 Uiso 1 1 d . U . . .
O1S O 0.5023(2) 0.03709(16) 0.21072(11) 0.0574(4) Uani 1 1 d . . . . .
C2S C 0.3061(3) -0.0181(3) 0.3266(2) 0.0688(6) Uani 1 1 d . . . . .
H2S1 H 0.2108 -0.0592 0.2536 0.103 Uiso 1 1 calc R U . . .
H2S2 H 0.2710 0.0561 0.3784 0.103 Uiso 1 1 calc R U . . .
H2S3 H 0.3270 -0.0984 0.3618 0.103 Uiso 1 1 calc R U . . .
C3S C 0.4742(3) 0.0543(2) 0.30486(17) 0.0486(5) Uani 1 1 d . . . . .
O4SA O 0.5902(3) 0.1551(4) 0.4008(2) 0.0608(8) Uani 0.785(8) 1 d . . P A 1
C5SA C 0.7684(5) 0.2281(5) 0.3940(3) 0.0687(11) Uani 0.785(8) 1 d . . P A 1
H5S1 H 0.8178 0.3241 0.4543 0.082 Uiso 0.785(8) 1 calc R U P A 1
H5S2 H 0.7546 0.2490 0.3184 0.082 Uiso 0.785(8) 1 calc R U P A 1
C6SA C 0.8967(5) 0.1304(4) 0.4096(3) 0.0698(11) Uani 0.785(8) 1 d . . P A 1
H6S1 H 0.8950 0.0956 0.4779 0.105 Uiso 0.785(8) 1 calc R U P A 1
H6S2 H 1.0173 0.1877 0.4193 0.105 Uiso 0.785(8) 1 calc R U P A 1
H6S3 H 0.8608 0.0446 0.3419 0.105 Uiso 0.785(8) 1 calc R U P A 1
O4SB O 0.6122(16) 0.0988(14) 0.4046(10) 0.064(3) Uiso 0.215(8) 1 d . . P A 2
C5SB C 0.795(3) 0.1568(19) 0.4028(14) 0.076(5) Uiso 0.215(8) 1 d . . P A 2
H5S3 H 0.8118 0.1010 0.3310 0.091 Uiso 0.215(8) 1 calc R U P A 2
H5S4 H 0.8801 0.1399 0.4682 0.091 Uiso 0.215(8) 1 calc R U P A 2
C6SB C 0.836(2) 0.319(2) 0.4101(13) 0.086(5) Uiso 0.215(8) 1 d . . P A 2
H6S4 H 0.7759 0.3332 0.3364 0.130 Uiso 0.215(8) 1 calc R U P A 2
H6S5 H 0.9654 0.3574 0.4276 0.130 Uiso 0.215(8) 1 calc R U P A 2
H6S6 H 0.7950 0.3718 0.4709 0.130 Uiso 0.215(8) 1 calc R U P 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 C2 1.215(2) . ?
C2 N22 1.380(2) . ?
C2 N3 1.383(2) . ?
N3 C4 1.361(2) . ?
N3 H3 0.87(2) . ?
C4 C5 1.376(2) . ?
C4 C21 1.426(2) . ?
C5 C9 1.401(2) . ?
C5 N6 1.474(2) . ?
N6 O8 1.197(2) . ?
N6 O7 1.211(2) . ?
C9 C13 1.376(2) . ?
C9 N10 1.474(2) . ?
N10 O12 1.211(2) . ?
N10 O11 1.215(2) . ?
C13 C17 1.402(2) . ?
C13 N14 1.481(2) . ?
N14 O16 1.206(2) . ?
N14 O15 1.211(2) . ?
C17 C21 1.381(2) . ?
C17 N18 1.464(2) . ?
N18 O19 1.205(2) . ?
N18 O20 1.207(2) . ?
C21 N22 1.358(2) . ?
N22 H22 0.83(2) . ?
O1S C3S 1.206(2) . ?
C2S C3S 1.474(3) . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?
C3S O4SA 1.331(3) . ?
C3S O4SB 1.342(11) . ?
O4SA C5SA 1.463(5) . ?
C5SA C6SA 1.482(6) . ?
C5SA H5S1 0.9700 . ?
C5SA H5S2 0.9700 . ?
C6SA H6S1 0.9600 . ?
C6SA H6S2 0.9600 . ?
C6SA H6S3 0.9600 . ?
O4SB C5SB 1.44(2) . ?
C5SB C6SB 1.46(2) . ?
C5SB H5S3 0.9700 . ?
C5SB H5S4 0.9700 . ?
C6SB H6S4 0.9600 . ?
C6SB H6S5 0.9600 . ?
C6SB H6S6 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 C2 N22 127.11(16) . . ?
O1 C2 N3 126.54(16) . . ?
N22 C2 N3 106.35(14) . . ?
C4 N3 C2 109.95(14) . . ?
C4 N3 H3 127.2(13) . . ?
C2 N3 H3 122.8(13) . . ?
N3 C4 C5 133.15(15) . . ?
N3 C4 C21 106.70(13) . . ?
C5 C4 C21 120.11(14) . . ?
C4 C5 C9 119.07(15) . . ?
C4 C5 N6 119.41(14) . . ?
C9 C5 N6 121.40(14) . . ?
O8 N6 O7 126.21(16) . . ?
O8 N6 C5 116.32(15) . . ?
O7 N6 C5 117.46(15) . . ?
C13 C9 C5 120.95(15) . . ?
C13 C9 N10 119.04(15) . . ?
C5 C9 N10 119.90(15) . . ?
O12 N10 O11 126.45(17) . . ?
O12 N10 C9 117.06(16) . . ?
O11 N10 C9 116.47(15) . . ?
C9 C13 C17 120.70(15) . . ?
C9 C13 N14 119.18(15) . . ?
C17 C13 N14 120.09(15) . . ?
O16 N14 O15 127.10(18) . . ?
O16 N14 C13 116.41(17) . . ?
O15 N14 C13 116.46(17) . . ?
C21 C17 C13 118.92(14) . . ?
C21 C17 N18 119.66(14) . . ?
C13 C17 N18 121.39(14) . . ?
O19 N18 O20 125.52(16) . . ?
O19 N18 C17 117.80(15) . . ?
O20 N18 C17 116.64(14) . . ?
N22 C21 C17 132.91(15) . . ?
N22 C21 C4 106.86(13) . . ?
C17 C21 C4 120.23(14) . . ?
C21 N22 C2 110.11(14) . . ?
C21 N22 H22 128.9(14) . . ?
C2 N22 H22 121.0(13) . . ?
C3S C2S H2S1 109.5 . . ?
C3S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C3S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
O1S C3S O4SA 121.8(2) . . ?
O1S C3S O4SB 121.0(5) . . ?
O1S C3S C2S 125.7(2) . . ?
O4SA C3S C2S 112.18(19) . . ?
O4SB C3S C2S 109.7(5) . . ?
C3S O4SA C5SA 118.0(2) . . ?
O4SA C5SA C6SA 111.3(4) . . ?
O4SA C5SA H5S1 109.4 . . ?
C6SA C5SA H5S1 109.4 . . ?
O4SA C5SA H5S2 109.4 . . ?
C6SA C5SA H5S2 109.4 . . ?
H5S1 C5SA H5S2 108.0 . . ?
C5SA C6SA H6S1 109.5 . . ?
C5SA C6SA H6S2 109.5 . . ?
H6S1 C6SA H6S2 109.5 . . ?
C5SA C6SA H6S3 109.5 . . ?
H6S1 C6SA H6S3 109.5 . . ?
H6S2 C6SA H6S3 109.5 . . ?
C3S O4SB C5SB 120.0(10) . . ?
O4SB C5SB C6SB 112.5(18) . . ?
O4SB C5SB H5S3 109.1 . . ?
C6SB C5SB H5S3 109.1 . . ?
O4SB C5SB H5S4 109.1 . . ?
C6SB C5SB H5S4 109.1 . . ?
H5S3 C5SB H5S4 107.8 . . ?
C5SB C6SB H6S4 109.5 . . ?
C5SB C6SB H6S5 109.5 . . ?
H6S4 C6SB H6S5 109.5 . . ?
C5SB C6SB H6S6 109.5 . . ?
H6S4 C6SB H6S6 109.5 . . ?
H6S5 C6SB H6S6 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 C2 N3 C4 -179.00(19) . . . . ?
N22 C2 N3 C4 0.39(19) . . . . ?
C2 N3 C4 C5 178.63(17) . . . . ?
C2 N3 C4 C21 0.62(18) . . . . ?
N3 C4 C5 C9 -178.00(17) . . . . ?
C21 C4 C5 C9 -0.2(2) . . . . ?
N3 C4 C5 N6 -1.9(3) . . . . ?
C21 C4 C5 N6 175.89(14) . . . . ?
C4 C5 N6 O8 38.0(2) . . . . ?
C9 C5 N6 O8 -145.95(18) . . . . ?
C4 C5 N6 O7 -140.89(16) . . . . ?
C9 C5 N6 O7 35.1(2) . . . . ?
C4 C5 C9 C13 1.1(2) . . . . ?
N6 C5 C9 C13 -174.91(15) . . . . ?
C4 C5 C9 N10 -175.05(14) . . . . ?
N6 C5 C9 N10 8.9(2) . . . . ?
C13 C9 N10 O12 54.9(2) . . . . ?
C5 C9 N10 O12 -128.83(18) . . . . ?
C13 C9 N10 O11 -123.75(18) . . . . ?
C5 C9 N10 O11 52.5(2) . . . . ?
C5 C9 C13 C17 -1.3(2) . . . . ?
N10 C9 C13 C17 174.85(15) . . . . ?
C5 C9 C13 N14 176.92(15) . . . . ?
N10 C9 C13 N14 -6.9(2) . . . . ?
C9 C13 N14 O16 -111.5(2) . . . . ?
C17 C13 N14 O16 66.8(2) . . . . ?
C9 C13 N14 O15 66.4(2) . . . . ?
C17 C13 N14 O15 -115.29(19) . . . . ?
C9 C13 C17 C21 0.7(2) . . . . ?
N14 C13 C17 C21 -177.60(15) . . . . ?
C9 C13 C17 N18 -177.38(15) . . . . ?
N14 C13 C17 N18 4.4(2) . . . . ?
C21 C17 N18 O19 -152.46(18) . . . . ?
C13 C17 N18 O19 25.6(3) . . . . ?
C21 C17 N18 O20 25.5(2) . . . . ?
C13 C17 N18 O20 -156.46(17) . . . . ?
C13 C17 C21 N22 179.29(17) . . . . ?
N18 C17 C21 N22 -2.6(3) . . . . ?
C13 C17 C21 C4 0.2(2) . . . . ?
N18 C17 C21 C4 178.31(14) . . . . ?
N3 C4 C21 N22 -1.41(17) . . . . ?
C5 C4 C21 N22 -179.73(14) . . . . ?
N3 C4 C21 C17 177.86(15) . . . . ?
C5 C4 C21 C17 -0.5(2) . . . . ?
C17 C21 N22 C2 -177.44(18) . . . . ?
C4 C21 N22 C2 1.70(18) . . . . ?
O1 C2 N22 C21 178.06(19) . . . . ?
N3 C2 N22 C21 -1.32(19) . . . . ?
O1S C3S O4SA C5SA -9.9(5) . . . . ?
C2S C3S O4SA C5SA 175.8(3) . . . . ?
C3S O4SA C5SA C6SA -82.4(4) . . . . ?
O1S C3S O4SB C5SB 12.8(16) . . . . ?
C2S C3S O4SB C5SB 172.8(12) . . . . ?
C3S O4SB C5SB C6SB 84.7(16) . . . . ?

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
C6SB H6S6 O19 0.96 2.51 3.428(15) 159.1 2_666
N3 H3 O1S 0.87(2) 1.92(2) 2.7613(19) 161.0(18) 2_655
N22 H22 O1 0.83(2) 2.02(2) 2.8346(19) 164.8(19) 2

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042

# start Validation Reply Form
_vrf_PLAT015_shrv328             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
