# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_jstvo213
_database_code_depnum_ccdc_archive 'CCDC 1008325'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;
_audit_creation_date             2013-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C5 H9 N5 O4'
_chemical_formula_sum            'C5 H9 N5 O4'
_chemical_formula_weight         203.17
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.68570(10)
_cell_length_b                   6.89930(10)
_cell_length_c                   10.2681(2)
_cell_angle_alpha                76.7114(10)
_cell_angle_beta                 79.0212(10)
_cell_angle_gamma                75.8661(10)
_cell_volume                     442.447(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3327
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.825
_cell_measurement_theta_min      6.744
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    1.147
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0560 before and 0.0414 after correction. The Ratio of minimum to maximum transmission is 0.8571. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.074
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6216
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.819
_diffrn_reflns_theta_min         4.470
_diffrn_ambient_temperature      173.09
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1430
_reflns_number_total             1680
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 (BRUKER, V2012.10-0, 2012)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT (BRUKER, V8.27BA, 20112)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2013 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.0823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3C,H3D,H3E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.21920(19) 0.58341(16) -0.30233(11) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.0644(2) 0.89960(17) -0.32812(12) 0.0459(3) Uani 1 1 d . . . . .
O3 O 0.24028(18) 0.96066(15) 0.00249(10) 0.0342(3) Uani 1 1 d . . . . .
O4 O 0.2473(2) 1.08334(15) -0.21205(11) 0.0405(3) Uani 1 1 d . . . . .
N1 N 0.28861(18) 0.40354(17) 0.18915(12) 0.0277(3) Uani 1 1 d . . . . .
N2 N 0.25206(17) 0.58400(17) 0.09487(11) 0.0241(3) Uani 1 1 d . . . . .
H2 H 0.242(3) 0.703(3) 0.109(2) 0.042(5) Uiso 1 1 d . . . . .
N3 N 0.25006(18) 0.38977(17) -0.05580(14) 0.0268(3) Uani 1 1 d . . . . .
H3A H 0.250(3) 0.372(3) -0.136(2) 0.034(5) Uiso 1 1 d . . . . .
H3B H 0.268(3) 0.284(3) 0.013(2) 0.037(5) Uiso 1 1 d . . . . .
N4 N 0.16231(19) 0.74816(17) -0.26266(12) 0.0279(3) Uani 1 1 d . . . . .
N5 N 0.23049(18) 0.94115(17) -0.11542(12) 0.0262(3) Uani 1 1 d . . . . .
C1 C 0.2453(3) 0.6275(3) 0.35202(17) 0.0466(4) Uani 1 1 d . . . . .
H1A H 0.3590 0.6974 0.3085 0.070 Uiso 1 1 calc GR . . . .
H1B H 0.2371 0.6060 0.4504 0.070 Uiso 1 1 calc GR . . . .
H1C H 0.1134 0.7109 0.3247 0.070 Uiso 1 1 calc GR . . . .
C2 C 0.2856(2) 0.4266(2) 0.31006(15) 0.0315(3) Uani 1 1 d . . . . .
C3 C 0.3281(3) 0.2352(3) 0.41398(18) 0.0446(4) Uani 1 1 d . . . . .
H3C H 0.3668 0.1171 0.3697 0.067 Uiso 1 1 calc GR . . . .
H3D H 0.2028 0.2249 0.4803 0.067 Uiso 1 1 calc GR . . . .
H3E H 0.4427 0.2385 0.4599 0.067 Uiso 1 1 calc GR . . . .
C4 C 0.23864(19) 0.57122(19) -0.03094(13) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.2090(2) 0.75426(19) -0.13366(13) 0.0232(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
O1 N4 1.2431(16) . ?
O2 N4 1.2177(16) . ?
O3 N5 1.2640(15) . ?
O4 N5 1.2342(15) . ?
N1 N2 1.3908(16) . ?
N1 C2 1.283(2) . ?
N2 H2 0.85(2) . ?
N2 C4 1.3360(18) . ?
N3 H3A 0.86(2) . ?
N3 H3B 0.89(2) . ?
N3 C4 1.3157(18) . ?
N4 C5 1.4295(18) . ?
N5 C5 1.3892(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.492(2) . ?
C2 C3 1.499(2) . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C4 C5 1.4462(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 N1 N2 114.81(12) . . ?
N1 N2 H2 126.1(13) . . ?
C4 N2 N1 117.83(11) . . ?
C4 N2 H2 116.0(13) . . ?
H3A N3 H3B 121.3(17) . . ?
C4 N3 H3A 121.5(13) . . ?
C4 N3 H3B 117.0(12) . . ?
O1 N4 C5 117.83(11) . . ?
O2 N4 O1 122.09(12) . . ?
O2 N4 C5 120.04(12) . . ?
O3 N5 C5 118.39(11) . . ?
O4 N5 O3 120.29(11) . . ?
O4 N5 C5 121.27(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 124.67(13) . . ?
N1 C2 C3 116.29(14) . . ?
C1 C2 C3 119.04(14) . . ?
C2 C3 H3C 109.5 . . ?
C2 C3 H3D 109.5 . . ?
C2 C3 H3E 109.5 . . ?
H3C C3 H3D 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
N2 C4 C5 119.75(11) . . ?
N3 C4 N2 117.86(12) . . ?
N3 C4 C5 122.38(12) . . ?
N4 C5 C4 120.52(11) . . ?
N5 C5 N4 116.58(11) . . ?
N5 C5 C4 122.86(12) . . ?

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
N2 H2 O3 0.85(2) 1.86(2) 2.5405(15) 136.4(18) .
N3 H3A O1 0.86(2) 1.98(2) 2.5971(17) 127.8(16) .
N3 H3B O3 0.89(2) 2.312(19) 2.8970(15) 122.9(15) 1_545

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 N4 C5 N5 152.72(12) . . . . ?
O1 N4 C5 C4 -25.23(18) . . . . ?
O2 N4 C5 N5 -29.41(19) . . . . ?
O2 N4 C5 C4 152.64(13) . . . . ?
O3 N5 C5 N4 169.46(11) . . . . ?
O3 N5 C5 C4 -12.6(2) . . . . ?
O4 N5 C5 N4 -13.1(2) . . . . ?
O4 N5 C5 C4 164.79(13) . . . . ?
N1 N2 C4 N3 3.45(17) . . . . ?
N1 N2 C4 C5 -177.56(11) . . . . ?
N2 N1 C2 C1 0.4(2) . . . . ?
N2 N1 C2 C3 -178.95(12) . . . . ?
N2 C4 C5 N4 -170.32(12) . . . . ?
N2 C4 C5 N5 11.86(19) . . . . ?
N3 C4 C5 N4 8.63(19) . . . . ?
N3 C4 C5 N5 -169.19(13) . . . . ?
C2 N1 N2 C4 -175.42(12) . . . . ?

_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'

####################################################################### 
# 
# 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_shrv200
_database_code_depnum_ccdc_archive 'CCDC 1008326'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H5 F3 N4 O7 S'
_chemical_formula_weight         298.17

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   7.5409(4)
_cell_length_b                   11.4812(6)
_cell_length_c                   12.3048(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.8020(10)
_cell_angle_gamma                90.00
_cell_volume                     1019.85(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          1.28
_exptl_crystal_size_mid          1.01
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_T_max  0.8423
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16143
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         30.52
_reflns_number_total             3116
_reflns_number_gt                2860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.4738P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3116
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.24782(15) 0.58915(10) 0.27049(9) 0.0164(2) Uani 1 1 d . . .
C2 C 1.13717(14) 0.55474(10) 0.35075(9) 0.01579(19) Uani 1 1 d . . .
H2 H 1.1950 0.4839 0.3940 0.019 Uiso 1 1 calc R . .
N3 N 1.41166(13) 0.54170(9) 0.29063(8) 0.01884(19) Uani 1 1 d . . .
H3A H 1.4824 0.5585 0.2471 0.023 Uiso 1 1 calc R . .
H3B H 1.4512 0.4930 0.3477 0.023 Uiso 1 1 calc R . .
N4 N 1.17914(15) 0.66200(10) 0.18781(9) 0.0251(2) Uani 1 1 d . . .
H4A H 1.2440 0.6818 0.1417 0.030 Uiso 1 1 calc R . .
H4B H 1.0679 0.6914 0.1781 0.030 Uiso 1 1 calc R . .
N5 N 1.13306(14) 0.65035(9) 0.43439(9) 0.01968(19) Uani 1 1 d . . .
O6 O 1.13137(18) 0.61875(11) 0.52839(9) 0.0366(3) Uani 1 1 d . . .
O7 O 1.13006(16) 0.75030(8) 0.40221(10) 0.0305(2) Uani 1 1 d . . .
N8 N 0.93842(14) 0.52656(9) 0.28557(9) 0.0213(2) Uani 1 1 d . . .
O9 O 0.92202(17) 0.46217(11) 0.20559(10) 0.0413(3) Uani 1 1 d . . .
O10 O 0.81635(13) 0.56683(10) 0.31998(9) 0.0302(2) Uani 1 1 d . . .
S11 S 0.62613(4) 0.75009(2) 0.07366(2) 0.01526(8) Uani 1 1 d . . .
C12 C 0.63399(17) 0.66564(11) -0.05155(10) 0.0210(2) Uani 1 1 d . . .
O13 O 0.81737(13) 0.75761(9) 0.14111(8) 0.0255(2) Uani 1 1 d . . .
O14 O 0.54776(13) 0.86189(8) 0.02868(8) 0.02353(19) Uani 1 1 d . . .
O15 O 0.50829(13) 0.68148(9) 0.12225(8) 0.02453(19) Uani 1 1 d . . .
F16 F 0.70010(19) 0.56064(9) -0.02121(9) 0.0506(3) Uani 1 1 d . . .
F17 F 0.73895(17) 0.71660(12) -0.10573(9) 0.0517(3) Uani 1 1 d . . .
F18 F 0.46732(13) 0.65388(11) -0.12353(8) 0.0463(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 N4 1.3032(15) . ?
C1 N3 1.3068(14) . ?
C1 C2 1.5179(15) . ?
C2 N5 1.5111(15) . ?
C2 N8 1.5164(14) . ?
C2 H2 1.0000 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 O7 1.2119(14) . ?
N5 O6 1.2158(14) . ?
N8 O9 1.2082(16) . ?
N8 O10 1.2107(15) . ?
S11 O15 1.4405(9) . ?
S11 O13 1.4436(9) . ?
S11 O14 1.4539(9) . ?
S11 C12 1.8358(12) . ?
C12 F17 1.3108(15) . ?
C12 F16 1.3167(16) . ?
C12 F18 1.3186(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
N4 C1 N3 123.79(11) . . ?
N4 C1 C2 120.39(10) . . ?
N3 C1 C2 115.82(10) . . ?
N5 C2 N8 107.67(9) . . ?
N5 C2 C1 112.17(9) . . ?
N8 C2 C1 110.89(9) . . ?
N5 C2 H2 108.7 . . ?
N8 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O7 N5 O6 126.09(12) . . ?
O7 N5 C2 117.87(10) . . ?
O6 N5 C2 116.04(10) . . ?
O9 N8 O10 127.54(11) . . ?
O9 N8 C2 114.47(11) . . ?
O10 N8 C2 117.95(10) . . ?
O15 S11 O13 115.32(6) . . ?
O15 S11 O14 114.15(6) . . ?
O13 S11 O14 113.24(6) . . ?
O15 S11 C12 103.47(6) . . ?
O13 S11 C12 104.18(6) . . ?
O14 S11 C12 104.77(6) . . ?
F17 C12 F16 108.54(12) . . ?
F17 C12 F18 107.62(12) . . ?
F16 C12 F18 107.81(12) . . ?
F17 C12 S11 111.21(9) . . ?
F16 C12 S11 110.30(9) . . ?
F18 C12 S11 111.23(9) . . ?

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
N4 C1 C2 N5 -74.97(13) . . . . ?
N3 C1 C2 N5 104.86(12) . . . . ?
N4 C1 C2 N8 45.45(15) . . . . ?
N3 C1 C2 N8 -134.72(10) . . . . ?
N8 C2 N5 O7 -87.62(12) . . . . ?
C1 C2 N5 O7 34.65(14) . . . . ?
N8 C2 N5 O6 91.72(12) . . . . ?
C1 C2 N5 O6 -146.01(11) . . . . ?
N5 C2 N8 O9 170.76(11) . . . . ?
C1 C2 N8 O9 47.70(14) . . . . ?
N5 C2 N8 O10 -11.35(14) . . . . ?
C1 C2 N8 O10 -134.41(11) . . . . ?
O15 S11 C12 F17 -179.41(10) . . . . ?
O13 S11 C12 F17 -58.47(11) . . . . ?
O14 S11 C12 F17 60.70(11) . . . . ?
O15 S11 C12 F16 -58.92(11) . . . . ?
O13 S11 C12 F16 62.02(11) . . . . ?
O14 S11 C12 F16 -178.80(10) . . . . ?
O15 S11 C12 F18 60.66(11) . . . . ?
O13 S11 C12 F18 -178.41(10) . . . . ?
O14 S11 C12 F18 -59.23(11) . . . . ?

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
N3 H3A O15 0.88 2.14 2.8760(14) 141.2 1_655
N3 H3B O14 0.88 2.14 2.9842(14) 161.1 2_745
N4 H4A O15 0.88 2.07 2.8318(14) 143.7 1_655
N4 H4B O13 0.88 1.96 2.8411(14) 174.6 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.52
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_shrv199
_database_code_depnum_ccdc_archive 'CCDC 1008327'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H5 Cl N4 O8'
_chemical_formula_weight         248.55

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   10.3533(11)
_cell_length_b                   13.0615(14)
_cell_length_c                   20.060(2)
_cell_angle_alpha                107.534(2)
_cell_angle_beta                 94.518(2)
_cell_angle_gamma                95.584(2)
_cell_volume                     2557.6(5)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1512
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41318
_diffrn_reflns_av_R_equivalents  0.1209
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         30.56
_reflns_number_total             15578
_reflns_number_gt                12724
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0461P)²+1.3989P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         15578
_refine_ls_number_parameters     870
_refine_ls_number_restraints     53
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.85492(14) 0.09061(12) 0.07441(8) 0.0176(3) Uani 1 1 d . . .
C2A C 0.71686(14) 0.03544(12) 0.04730(7) 0.0169(3) Uani 1 1 d . . .
H2A H 0.6891 0.0492 0.0022 0.020 Uiso 1 1 calc R . .
N3A N 0.91504(14) 0.07402(14) 0.12932(8) 0.0276(3) Uani 1 1 d . . .
H3AA H 0.9958 0.1043 0.1450 0.033 Uiso 1 1 calc R . .
H3AB H 0.8747 0.0325 0.1506 0.033 Uiso 1 1 calc R . .
N4A N 0.90681(14) 0.15047(12) 0.03981(7) 0.0250(3) Uani 1 1 d . . .
H4AA H 0.9874 0.1829 0.0530 0.030 Uiso 1 1 calc R . .
H4AB H 0.8614 0.1586 0.0032 0.030 Uiso 1 1 calc R . .
N5A N 0.62176(13) 0.07711(11) 0.09991(7) 0.0206(3) Uani 1 1 d . . .
O6A O 0.66393(12) 0.15138(10) 0.15270(7) 0.0282(3) Uani 1 1 d . . .
O7A O 0.50942(12) 0.03417(13) 0.08373(7) 0.0359(3) Uani 1 1 d . . .
N8A N 0.71369(15) -0.08578(11) 0.03380(7) 0.0245(3) Uani 1 1 d . . .
O9A O 0.7482(3) -0.13409(15) -0.02081(11) 0.0911(8) Uani 1 1 d . . .
O10A O 0.68184(19) -0.12407(11) 0.07785(8) 0.0490(4) Uani 1 1 d . . .
C1B C 0.16720(14) 0.43574(11) 0.41134(7) 0.0159(3) Uani 1 1 d . . .
C2B C 0.05941(15) 0.34575(12) 0.37148(8) 0.0185(3) Uani 1 1 d . . .
H2B H 0.0067 0.3713 0.3371 0.022 Uiso 1 1 calc R . .
N3B N 0.18047(14) 0.51798(11) 0.38820(7) 0.0230(3) Uani 1 1 d . . .
H3BA H 0.2416 0.5726 0.4089 0.028 Uiso 1 1 calc R . .
H3BB H 0.1284 0.5193 0.3517 0.028 Uiso 1 1 calc R . .
N4B N 0.24094(15) 0.42814(11) 0.46526(8) 0.0256(3) Uani 1 1 d . . .
H4BA H 0.3034 0.4807 0.4877 0.031 Uiso 1 1 calc R . .
H4BB H 0.2281 0.3704 0.4790 0.031 Uiso 1 1 calc R . .
N5B N -0.03046(13) 0.31560(11) 0.42053(7) 0.0218(3) Uani 1 1 d . . .
O6B O -0.07643(14) 0.39082(12) 0.45816(7) 0.0363(3) Uani 1 1 d . . .
O7B O -0.05179(16) 0.22147(11) 0.41662(7) 0.0380(3) Uani 1 1 d . . .
N8B N 0.11180(19) 0.24368(13) 0.33165(10) 0.0392(4) Uani 1 1 d . . .
O9B O 0.0508(3) 0.19409(14) 0.27515(9) 0.0741(7) Uani 1 1 d . . .
O10B O 0.20484(19) 0.21698(15) 0.36181(14) 0.0831(9) Uani 1 1 d . . .
C1C C 0.42254(14) 0.69466(12) 0.16174(7) 0.0171(3) Uani 1 1 d . . .
C2C C 0.41989(16) 0.72187(12) 0.24046(8) 0.0193(3) Uani 1 1 d . . .
H2C H 0.4391 0.8021 0.2625 0.023 Uiso 1 1 calc R . .
N3C N 0.45971(14) 0.77445(11) 0.13881(7) 0.0220(3) Uani 1 1 d . . .
H3CA H 0.4618 0.7632 0.0934 0.026 Uiso 1 1 calc R . .
H3CB H 0.4828 0.8398 0.1687 0.026 Uiso 1 1 calc R . .
N4C N 0.38662(16) 0.59517(11) 0.12120(7) 0.0281(3) Uani 1 1 d . . .
H4CA H 0.3867 0.5790 0.0753 0.034 Uiso 1 1 calc R . .
H4CB H 0.3623 0.5443 0.1398 0.034 Uiso 1 1 calc R . .
N5C N 0.51629(15) 0.66811(13) 0.27483(8) 0.0285(3) Uani 1 1 d . . .
O6C O 0.55652(16) 0.71620(14) 0.33577(7) 0.0465(4) Uani 1 1 d . . .
O7C O 0.54173(17) 0.57980(13) 0.23976(9) 0.0468(4) Uani 1 1 d . . .
N8C N 0.28448(16) 0.68428(12) 0.25549(8) 0.0283(3) Uani 1 1 d . . .
O9C O 0.19526(16) 0.70578(17) 0.22136(12) 0.0598(5) Uani 1 1 d . . .
O10C O 0.27626(16) 0.63819(13) 0.29910(7) 0.0442(4) Uani 1 1 d . . .
C1D C 0.24936(15) 0.01143(12) 0.50900(8) 0.0194(3) Uani 1 1 d . A .
C2D C 0.2526(2) 0.02307(10) 0.43612(9) 0.0279(4) Uani 1 1 d D . .
H2D H 0.266(2) 0.0997(3) 0.4356(6) 0.033 Uiso 1 1 d D . .
N3D N 0.2796(2) 0.10051(12) 0.56098(8) 0.0376(4) Uani 1 1 d . . .
H3DA H 0.2799 0.0993 0.6046 0.045 Uiso 1 1 calc R A .
H3DB H 0.2997 0.1621 0.5526 0.045 Uiso 1 1 calc R . .
N4D N 0.21873(18) -0.08213(12) 0.51642(8) 0.0313(4) Uani 1 1 d . . .
H4DA H 0.2174 -0.0885 0.5588 0.038 Uiso 1 1 calc R A .
H4DB H 0.1991 -0.1397 0.4791 0.038 Uiso 1 1 calc R . .
N5D N 0.3348(3) -0.0411(2) 0.39020(14) 0.0275(6) Uani 0.555(3) 1 d P A 1
O6D O 0.3308(4) -0.1356(2) 0.38504(18) 0.0645(11) Uani 0.555(3) 1 d P A 1
O7D O 0.4070(6) -0.0099(7) 0.3587(3) 0.081(2) Uani 0.555(3) 1 d P A 1
N5D' N 0.3939(5) -0.0167(3) 0.4142(2) 0.0365(10) Uani 0.445(3) 1 d P A 2
O6D' O 0.4674(4) -0.0375(4) 0.4555(3) 0.0608(12) Uani 0.445(3) 1 d P . 2
O7D' O 0.4097(7) 0.0017(6) 0.3571(3) 0.0458(16) Uani 0.445(3) 1 d P A 2
N8D N 0.1535(4) -0.0392(3) 0.3865(2) 0.0306(7) Uani 0.423(3) 1 d PDU A 3
O9D O 0.1671(4) -0.1215(3) 0.34242(19) 0.0420(8) Uani 0.423(3) 1 d PDU A 3
O10D O 0.0558(6) 0.0029(5) 0.3974(3) 0.0654(12) Uani 0.423(3) 1 d PDU A 3
N8D' N 0.1071(4) -0.0173(3) 0.39353(16) 0.0308(6) Uani 0.577(3) 1 d PDU A 4
O9D' O 0.1004(3) -0.0675(3) 0.33140(16) 0.0512(7) Uani 0.577(3) 1 d PDU A 4
O10' O 0.0179(3) 0.0048(2) 0.42799(16) 0.0414(6) Uani 0.577(3) 1 d PDU A 4
C1E C 0.89052(14) 0.64051(12) 0.16885(8) 0.0173(3) Uani 1 1 d . . .
C2E C 0.88004(15) 0.60020(12) 0.08906(8) 0.0186(3) Uani 1 1 d . . .
H2E H 0.8892 0.5212 0.0731 0.022 Uiso 1 1 calc R . .
N3E N 0.86402(15) 0.56668(11) 0.19877(7) 0.0242(3) Uani 1 1 d . . .
H3EA H 0.8662 0.5849 0.2448 0.029 Uiso 1 1 calc R . .
H3EB H 0.8439 0.4985 0.1730 0.029 Uiso 1 1 calc R . .
N4E N 0.92129(15) 0.74339(11) 0.20288(7) 0.0232(3) Uani 1 1 d . . .
H4EA H 0.9251 0.7665 0.2491 0.028 Uiso 1 1 calc R . .
H4EB H 0.9382 0.7896 0.1796 0.028 Uiso 1 1 calc R . .
N5E N 0.98231(14) 0.66037(12) 0.06033(7) 0.0229(3) Uani 1 1 d . . .
O6E O 0.95948(14) 0.74784(10) 0.05569(7) 0.0332(3) Uani 1 1 d . . .
O7E O 1.07864(14) 0.61703(14) 0.04466(8) 0.0412(4) Uani 1 1 d . . .
N8E N 0.74886(14) 0.61747(11) 0.05770(7) 0.0229(3) Uani 1 1 d . . .
O9E O 0.73415(14) 0.59640(12) -0.00593(7) 0.0356(3) Uani 1 1 d . . .
O10E O 0.66896(13) 0.64764(12) 0.09848(7) 0.0344(3) Uani 1 1 d . . .
C1F C 0.47507(14) 0.25338(12) 0.25113(8) 0.0161(3) Uani 1 1 d . . .
C2F C 0.57092(14) 0.35609(11) 0.27155(7) 0.0164(3) Uani 1 1 d . . .
H2F H 0.5640 0.3888 0.2325 0.020 Uiso 1 1 calc R . .
N3F N 0.38999(14) 0.24060(12) 0.19671(8) 0.0245(3) Uani 1 1 d . . .
H3FA H 0.3307 0.1832 0.1822 0.029 Uiso 1 1 calc R . .
H3FB H 0.3920 0.2894 0.1745 0.029 Uiso 1 1 calc R . .
N4F N 0.47878(14) 0.18535(11) 0.28670(7) 0.0218(3) Uani 1 1 d . . .
H4FA H 0.4217 0.1265 0.2745 0.026 Uiso 1 1 calc R . .
H4FB H 0.5383 0.1980 0.3230 0.026 Uiso 1 1 calc R . .
N5F N 0.53950(15) 0.43823(11) 0.33848(7) 0.0235(3) Uani 1 1 d . . .
O6F O 0.63027(15) 0.49803(11) 0.37698(7) 0.0370(3) Uani 1 1 d . . .
O7F O 0.42356(14) 0.43932(13) 0.34417(8) 0.0395(4) Uani 1 1 d . . .
N8F N 0.71083(13) 0.33802(11) 0.28484(7) 0.0213(3) Uani 1 1 d . . .
O9F O 0.78965(13) 0.37544(11) 0.25376(7) 0.0323(3) Uani 1 1 d . . .
O10F O 0.73503(13) 0.29009(13) 0.32673(8) 0.0394(3) Uani 1 1 d . . .
Cl1A Cl 0.54019(4) 0.28434(3) 0.487765(18) 0.01848(7) Uani 1 1 d . . .
O1A O 0.54898(14) 0.38511(11) 0.47253(8) 0.0384(3) Uani 1 1 d . . .
O2A O 0.57679(19) 0.20173(14) 0.42969(7) 0.0518(5) Uani 1 1 d . . .
O3A O 0.62676(13) 0.29452(11) 0.54962(7) 0.0308(3) Uani 1 1 d . . .
O4A O 0.40791(13) 0.25525(12) 0.49805(8) 0.0377(3) Uani 1 1 d . . .
Cl1B Cl 0.93318(4) 0.69321(3) 0.391029(19) 0.02145(8) Uani 1 1 d . . .
O1B O 0.91867(14) 0.57977(11) 0.35101(8) 0.0389(4) Uani 1 1 d . . .
O2B O 0.86307(14) 0.71142(12) 0.45173(7) 0.0329(3) Uani 1 1 d . . .
O3B O 1.06885(13) 0.73089(11) 0.41202(8) 0.0341(3) Uani 1 1 d . . .
O4B O 0.88043(15) 0.75042(14) 0.34578(7) 0.0401(3) Uani 1 1 d . . .
Cl1C Cl 0.71555(4) -0.03092(3) 0.266667(18) 0.01829(7) Uani 1 1 d . . .
O1C O 0.69646(15) -0.13154(11) 0.28248(8) 0.0347(3) Uani 1 1 d . . .
O2C O 0.73864(17) 0.05768(12) 0.33092(7) 0.0441(4) Uani 1 1 d . . .
O3C O 0.59906(13) -0.01990(10) 0.22662(7) 0.0289(3) Uani 1 1 d . . .
O4C O 0.82420(14) -0.03205(13) 0.22670(9) 0.0411(3) Uani 1 1 d . . .
Cl1D Cl 0.20750(3) -0.04345(3) 0.157618(18) 0.01832(7) Uani 1 1 d . . .
O1D O 0.19580(13) 0.05742(11) 0.14279(8) 0.0352(3) Uani 1 1 d . . .
O2D O 0.08650(13) -0.07956(11) 0.17741(8) 0.0323(3) Uani 1 1 d . . .
O3D O 0.31191(13) -0.02611(10) 0.21323(7) 0.0301(3) Uani 1 1 d . . .
O4D O 0.23868(13) -0.12147(12) 0.09520(7) 0.0344(3) Uani 1 1 d . . .
Cl1E Cl 0.13172(3) 0.38805(3) 0.167080(18) 0.01787(7) Uani 1 1 d . . .
O1E O 0.06071(14) 0.42639(13) 0.11705(7) 0.0361(3) Uani 1 1 d . . .
O2E O 0.26803(12) 0.43256(10) 0.17704(7) 0.0267(3) Uani 1 1 d . . .
O3E O 0.07856(14) 0.41918(11) 0.23287(7) 0.0320(3) Uani 1 1 d . . .
O4E O 0.12385(12) 0.27160(10) 0.14036(7) 0.0291(3) Uani 1 1 d . . .
Cl1F Cl 0.61728(4) 0.34081(3) 0.062519(17) 0.01945(7) Uani 1 1 d . . .
O1F O 0.58877(16) 0.22974(11) 0.01854(8) 0.0389(4) Uani 1 1 d . . .
O2F O 0.53766(14) 0.36277(12) 0.11882(7) 0.0353(3) Uani 1 1 d . . .
O3F O 0.5928(2) 0.41018(13) 0.02106(8) 0.0521(5) Uani 1 1 d . . .
O4F O 0.75250(15) 0.36240(14) 0.09011(8) 0.0471(4) 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
C1A N4A 1.298(2) . ?
C1A N3A 1.308(2) . ?
C1A C2A 1.516(2) . ?
C2A N5A 1.517(2) . ?
C2A N8A 1.520(2) . ?
C2A H2A 1.0000 . ?
N3A H3AA 0.8800 . ?
N3A H3AB 0.8800 . ?
N4A H4AA 0.8800 . ?
N4A H4AB 0.8800 . ?
N5A O7A 1.2151(17) . ?
N5A O6A 1.2161(17) . ?
N8A O9A 1.189(2) . ?
N8A O10A 1.192(2) . ?
C1B N3B 1.292(2) . ?
C1B N4B 1.309(2) . ?
C1B C2B 1.5179(19) . ?
C2B N8B 1.509(2) . ?
C2B N5B 1.515(2) . ?
C2B H2B 1.0000 . ?
N3B H3BA 0.8800 . ?
N3B H3BB 0.8800 . ?
N4B H4BA 0.8800 . ?
N4B H4BB 0.8800 . ?
N5B O7B 1.2054(19) . ?
N5B O6B 1.209(2) . ?
N8B O9B 1.212(2) . ?
N8B O10B 1.231(3) . ?
C1C N3C 1.298(2) . ?
C1C N4C 1.3077(19) . ?
C1C C2C 1.514(2) . ?
C2C N5C 1.511(2) . ?
C2C N8C 1.523(2) . ?
C2C H2C 1.0000 . ?
N3C H3CA 0.8800 . ?
N3C H3CB 0.8800 . ?
N4C H4CA 0.8800 . ?
N4C H4CB 0.8800 . ?
N5C O6C 1.2119(19) . ?
N5C O7C 1.222(2) . ?
N8C O10C 1.206(2) . ?
N8C O9C 1.211(2) . ?
C1D N4D 1.288(2) . ?
C1D N3D 1.2983(19) . ?
C1D C2D 1.517(2) . ?
C2D N8D 1.376(4) . ?
C2D N5D 1.440(3) . ?
C2D N8D' 1.627(4) . ?
C2D N5D' 1.648(5) . ?
C2D H2D 0.9999(11) . ?
N3D H3DA 0.8800 . ?
N3D H3DB 0.8800 . ?
N4D H4DA 0.8800 . ?
N4D H4DB 0.8800 . ?
N5D O7D 1.137(7) . ?
N5D O6D 1.204(4) . ?
N5D' O6D' 1.190(7) . ?
N5D' O7D' 1.259(8) . ?
O6D' O6D' 1.797(10) 2_656 ?
N8D O9D 1.198(5) . ?
N8D O10D 1.201(7) . ?
N8D' O10' 1.203(5) . ?
N8D' O9D' 1.214(4) . ?
C1E N3E 1.299(2) . ?
C1E N4E 1.3049(19) . ?
C1E C2E 1.518(2) . ?
C2E N5E 1.509(2) . ?
C2E N8E 1.517(2) . ?
C2E H2E 1.0000 . ?
N3E H3EA 0.8800 . ?
N3E H3EB 0.8800 . ?
N4E H4EA 0.8800 . ?
N4E H4EB 0.8800 . ?
N5E O7E 1.211(2) . ?
N5E O6E 1.218(2) . ?
N8E O9E 1.2156(18) . ?
N8E O10E 1.218(2) . ?
C1F N4F 1.298(2) . ?
C1F N3F 1.3060(19) . ?
C1F C2F 1.5159(19) . ?
C2F N8F 1.506(2) . ?
C2F N5F 1.5259(19) . ?
C2F H2F 1.0000 . ?
N3F H3FA 0.8800 . ?
N3F H3FB 0.8800 . ?
N4F H4FA 0.8800 . ?
N4F H4FB 0.8800 . ?
N5F O6F 1.2120(19) . ?
N5F O7F 1.216(2) . ?
N8F O10F 1.215(2) . ?
N8F O9F 1.2163(19) . ?
Cl1A O4A 1.4329(14) . ?
Cl1A O2A 1.4341(15) . ?
Cl1A O1A 1.4344(14) . ?
Cl1A O3A 1.4363(13) . ?
Cl1B O3B 1.4283(13) . ?
Cl1B O2B 1.4368(14) . ?
Cl1B O1B 1.4434(14) . ?
Cl1B O4B 1.4459(15) . ?
Cl1C O4C 1.4305(14) . ?
Cl1C O2C 1.4341(14) . ?
Cl1C O3C 1.4392(13) . ?
Cl1C O1C 1.4414(14) . ?
Cl1D O2D 1.4232(13) . ?
Cl1D O4D 1.4386(13) . ?
Cl1D O3D 1.4403(12) . ?
Cl1D O1D 1.4493(14) . ?
Cl1E O3E 1.4299(13) . ?
Cl1E O1E 1.4341(14) . ?
Cl1E O4E 1.4441(12) . ?
Cl1E O2E 1.4476(12) . ?
Cl1F O2F 1.4264(14) . ?
Cl1F O3F 1.4292(16) . ?
Cl1F O4F 1.4328(15) . ?
Cl1F O1F 1.4403(13) . ?

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
N4A C1A N3A 124.15(14) . . ?
N4A C1A C2A 116.72(13) . . ?
N3A C1A C2A 119.12(14) . . ?
C1A C2A N5A 111.49(11) . . ?
C1A C2A N8A 109.31(13) . . ?
N5A C2A N8A 108.60(12) . . ?
C1A C2A H2A 109.1 . . ?
N5A C2A H2A 109.1 . . ?
N8A C2A H2A 109.1 . . ?
C1A N3A H3AA 120.0 . . ?
C1A N3A H3AB 120.0 . . ?
H3AA N3A H3AB 120.0 . . ?
C1A N4A H4AA 120.0 . . ?
C1A N4A H4AB 120.0 . . ?
H4AA N4A H4AB 120.0 . . ?
O7A N5A O6A 126.55(15) . . ?
O7A N5A C2A 116.01(12) . . ?
O6A N5A C2A 117.41(12) . . ?
O9A N8A O10A 125.52(18) . . ?
O9A N8A C2A 115.13(16) . . ?
O10A N8A C2A 119.31(14) . . ?
N3B C1B N4B 123.36(13) . . ?
N3B C1B C2B 115.69(13) . . ?
N4B C1B C2B 120.95(14) . . ?
N8B C2B N5B 106.93(13) . . ?
N8B C2B C1B 112.53(13) . . ?
N5B C2B C1B 111.60(11) . . ?
N8B C2B H2B 108.6 . . ?
N5B C2B H2B 108.6 . . ?
C1B C2B H2B 108.6 . . ?
C1B N3B H3BA 120.0 . . ?
C1B N3B H3BB 120.0 . . ?
H3BA N3B H3BB 120.0 . . ?
C1B N4B H4BA 120.0 . . ?
C1B N4B H4BB 120.0 . . ?
H4BA N4B H4BB 120.0 . . ?
O7B N5B O6B 127.38(16) . . ?
O7B N5B C2B 118.06(14) . . ?
O6B N5B C2B 114.51(14) . . ?
O9B N8B O10B 127.8(2) . . ?
O9B N8B C2B 115.1(2) . . ?
O10B N8B C2B 116.92(16) . . ?
N3C C1C N4C 124.07(14) . . ?
N3C C1C C2C 116.37(13) . . ?
N4C C1C C2C 119.56(14) . . ?
N5C C2C C1C 113.52(13) . . ?
N5C C2C N8C 107.10(13) . . ?
C1C C2C N8C 109.34(12) . . ?
N5C C2C H2C 108.9 . . ?
C1C C2C H2C 108.9 . . ?
N8C C2C H2C 108.9 . . ?
C1C N3C H3CA 120.0 . . ?
C1C N3C H3CB 120.0 . . ?
H3CA N3C H3CB 120.0 . . ?
C1C N4C H4CA 120.0 . . ?
C1C N4C H4CB 120.0 . . ?
H4CA N4C H4CB 120.0 . . ?
O6C N5C O7C 126.85(18) . . ?
O6C N5C C2C 115.70(16) . . ?
O7C N5C C2C 117.38(14) . . ?
O10C N8C O9C 127.06(18) . . ?
O10C N8C C2C 118.46(16) . . ?
O9C N8C C2C 114.48(17) . . ?
N4D C1D N3D 124.17(16) . . ?
N4D C1D C2D 120.35(13) . . ?
N3D C1D C2D 115.49(14) . . ?
N8D C2D N5D 83.5(2) . . ?
N8D C2D C1D 115.1(2) . . ?
N5D C2D C1D 117.58(18) . . ?
N8D C2D N8D' 20.42(19) . . ?
N5D C2D N8D' 103.5(2) . . ?
C1D C2D N8D' 108.37(17) . . ?
N8D C2D N5D' 109.7(3) . . ?
N5D C2D N5D' 26.21(16) . . ?
C1D C2D N5D' 102.8(2) . . ?
N8D' C2D N5D' 129.7(2) . . ?
N8D C2D H2D 112.6(11) . . ?
N5D C2D H2D 110.1(10) . . ?
C1D C2D H2D 114.3(7) . . ?
N8D' C2D H2D 101.0(12) . . ?
N5D' C2D H2D 100.8(12) . . ?
C1D N3D H3DA 120.0 . . ?
C1D N3D H3DB 120.0 . . ?
H3DA N3D H3DB 120.0 . . ?
C1D N4D H4DA 120.0 . . ?
C1D N4D H4DB 120.0 . . ?
H4DA N4D H4DB 120.0 . . ?
O7D N5D O6D 115.8(5) . . ?
O7D N5D C2D 125.6(5) . . ?
O6D N5D C2D 118.6(3) . . ?
O6D' N5D' O7D' 131.9(6) . . ?
O6D' N5D' C2D 120.4(4) . . ?
O7D' N5D' C2D 106.3(5) . . ?
N5D' O6D' O6D' 131.7(5) . 2_656 ?
O9D N8D O10D 128.5(5) . . ?
O9D N8D C2D 123.6(4) . . ?
O10D N8D C2D 107.8(4) . . ?
O10' N8D' O9D' 127.3(4) . . ?
O10' N8D' C2D 115.7(3) . . ?
O9D' N8D' C2D 117.0(3) . . ?
N3E C1E N4E 124.18(14) . . ?
N3E C1E C2E 115.42(13) . . ?
N4E C1E C2E 120.39(14) . . ?
N5E C2E N8E 106.20(13) . . ?
N5E C2E C1E 112.38(12) . . ?
N8E C2E C1E 110.34(12) . . ?
N5E C2E H2E 109.3 . . ?
N8E C2E H2E 109.3 . . ?
C1E C2E H2E 109.3 . . ?
C1E N3E H3EA 120.0 . . ?
C1E N3E H3EB 120.0 . . ?
H3EA N3E H3EB 120.0 . . ?
C1E N4E H4EA 120.0 . . ?
C1E N4E H4EB 120.0 . . ?
H4EA N4E H4EB 120.0 . . ?
O7E N5E O6E 126.81(16) . . ?
O7E N5E C2E 116.73(15) . . ?
O6E N5E C2E 116.47(14) . . ?
O9E N8E O10E 127.28(16) . . ?
O9E N8E C2E 115.88(14) . . ?
O10E N8E C2E 116.80(13) . . ?
N4F C1F N3F 123.83(14) . . ?
N4F C1F C2F 121.11(13) . . ?
N3F C1F C2F 115.06(14) . . ?
N8F C2F C1F 113.70(12) . . ?
N8F C2F N5F 106.75(11) . . ?
C1F C2F N5F 111.19(12) . . ?
N8F C2F H2F 108.4 . . ?
C1F C2F H2F 108.4 . . ?
N5F C2F H2F 108.4 . . ?
C1F N3F H3FA 120.0 . . ?
C1F N3F H3FB 120.0 . . ?
H3FA N3F H3FB 120.0 . . ?
C1F N4F H4FA 120.0 . . ?
C1F N4F H4FB 120.0 . . ?
H4FA N4F H4FB 120.0 . . ?
O6F N5F O7F 127.87(15) . . ?
O6F N5F C2F 117.38(14) . . ?
O7F N5F C2F 114.59(13) . . ?
O10F N8F O9F 126.11(16) . . ?
O10F N8F C2F 117.24(14) . . ?
O9F N8F C2F 116.62(14) . . ?
O4A Cl1A O2A 109.24(11) . . ?
O4A Cl1A O1A 108.74(9) . . ?
O2A Cl1A O1A 109.56(11) . . ?
O4A Cl1A O3A 110.41(9) . . ?
O2A Cl1A O3A 108.84(9) . . ?
O1A Cl1A O3A 110.03(8) . . ?
O3B Cl1B O2B 110.21(8) . . ?
O3B Cl1B O1B 108.90(8) . . ?
O2B Cl1B O1B 111.28(9) . . ?
O3B Cl1B O4B 109.79(10) . . ?
O2B Cl1B O4B 108.94(9) . . ?
O1B Cl1B O4B 107.69(9) . . ?
O4C Cl1C O2C 110.60(10) . . ?
O4C Cl1C O3C 110.05(9) . . ?
O2C Cl1C O3C 108.74(9) . . ?
O4C Cl1C O1C 108.97(9) . . ?
O2C Cl1C O1C 109.58(9) . . ?
O3C Cl1C O1C 108.88(8) . . ?
O2D Cl1D O4D 110.59(8) . . ?
O2D Cl1D O3D 110.96(9) . . ?
O4D Cl1D O3D 108.94(8) . . ?
O2D Cl1D O1D 108.61(9) . . ?
O4D Cl1D O1D 108.49(10) . . ?
O3D Cl1D O1D 109.21(8) . . ?
O3E Cl1E O1E 110.07(9) . . ?
O3E Cl1E O4E 109.92(9) . . ?
O1E Cl1E O4E 109.32(8) . . ?
O3E Cl1E O2E 109.62(8) . . ?
O1E Cl1E O2E 109.86(9) . . ?
O4E Cl1E O2E 108.02(8) . . ?
O2F Cl1F O3F 108.84(10) . . ?
O2F Cl1F O4F 109.94(9) . . ?
O3F Cl1F O4F 108.63(12) . . ?
O2F Cl1F O1F 111.06(9) . . ?
O3F Cl1F O1F 109.16(9) . . ?
O4F Cl1F O1F 109.18(10) . . ?

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
N4A C1A C2A N5A -115.26(16) . . . . ?
N3A C1A C2A N5A 66.08(19) . . . . ?
N4A C1A C2A N8A 124.66(15) . . . . ?
N3A C1A C2A N8A -54.00(19) . . . . ?
C1A C2A N5A O7A -177.15(15) . . . . ?
N8A C2A N5A O7A -56.65(18) . . . . ?
C1A C2A N5A O6A 4.8(2) . . . . ?
N8A C2A N5A O6A 125.30(15) . . . . ?
C1A C2A N8A O9A -81.6(2) . . . . ?
N5A C2A N8A O9A 156.6(2) . . . . ?
C1A C2A N8A O10A 96.22(19) . . . . ?
N5A C2A N8A O10A -25.6(2) . . . . ?
N3B C1B C2B N8B 111.74(17) . . . . ?
N4B C1B C2B N8B -67.9(2) . . . . ?
N3B C1B C2B N5B -128.04(15) . . . . ?
N4B C1B C2B N5B 52.3(2) . . . . ?
N8B C2B N5B O7B -5.0(2) . . . . ?
C1B C2B N5B O7B -128.47(15) . . . . ?
N8B C2B N5B O6B 177.37(14) . . . . ?
C1B C2B N5B O6B 53.91(19) . . . . ?
N5B C2B N8B O9B 93.8(2) . . . . ?
C1B C2B N8B O9B -143.34(18) . . . . ?
N5B C2B N8B O10B -81.6(2) . . . . ?
C1B C2B N8B O10B 41.3(3) . . . . ?
N3C C1C C2C N5C -115.37(16) . . . . ?
N4C C1C C2C N5C 65.54(19) . . . . ?
N3C C1C C2C N8C 125.11(15) . . . . ?
N4C C1C C2C N8C -54.0(2) . . . . ?
C1C C2C N5C O6C 151.60(15) . . . . ?
N8C C2C N5C O6C -87.62(17) . . . . ?
C1C C2C N5C O7C -31.1(2) . . . . ?
N8C C2C N5C O7C 89.69(18) . . . . ?
N5C C2C N8C O10C 12.55(19) . . . . ?
C1C C2C N8C O10C 135.95(16) . . . . ?
N5C C2C N8C O9C -167.96(16) . . . . ?
C1C C2C N8C O9C -44.6(2) . . . . ?
N4D C1D C2D N8D 40.0(3) . . . . ?
N3D C1D C2D N8D -140.3(3) . . . . ?
N4D C1D C2D N5D -56.0(3) . . . . ?
N3D C1D C2D N5D 123.7(2) . . . . ?
N4D C1D C2D N8D' 60.7(2) . . . . ?
N3D C1D C2D N8D' -119.5(2) . . . . ?
N4D C1D C2D N5D' -79.2(2) . . . . ?
N3D C1D C2D N5D' 100.5(2) . . . . ?
N8D C2D N5D O7D 113.2(5) . . . . ?
C1D C2D N5D O7D -131.8(5) . . . . ?
N8D' C2D N5D O7D 108.8(5) . . . . ?
N5D' C2D N5D O7D -71.4(7) . . . . ?
N8D C2D N5D O6D -68.7(4) . . . . ?
C1D C2D N5D O6D 46.4(4) . . . . ?
N8D' C2D N5D O6D -73.0(4) . . . . ?
N5D' C2D N5D O6D 106.7(6) . . . . ?
N8D C2D N5D' O6D' -128.3(5) . . . . ?
N5D C2D N5D' O6D' -133.2(7) . . . . ?
C1D C2D N5D' O6D' -5.4(5) . . . . ?
N8D' C2D N5D' O6D' -132.9(4) . . . . ?
N8D C2D N5D' O7D' 63.9(5) . . . . ?
N5D C2D N5D' O7D' 59.0(5) . . . . ?
C1D C2D N5D' O7D' -173.2(4) . . . . ?
N8D' C2D N5D' O7D' 59.3(5) . . . . ?
O7D' N5D' O6D' O6D' 112.5(8) . . . 2_656 ?
C2D N5D' O6D' O6D' -51.7(8) . . . 2_656 ?
N5D C2D N8D O9D 15.1(5) . . . . ?
C1D C2D N8D O9D -102.4(5) . . . . ?
N8D' C2D N8D O9D -177.2(11) . . . . ?
N5D' C2D N8D O9D 13.0(5) . . . . ?
N5D C2D N8D O10D -166.5(5) . . . . ?
C1D C2D N8D O10D 76.0(5) . . . . ?
N8D' C2D N8D O10D 1.2(6) . . . . ?
N5D' C2D N8D O10D -168.6(4) . . . . ?
N8D C2D N8D' O10' 150.0(9) . . . . ?
N5D C2D N8D' O10' 162.5(3) . . . . ?
C1D C2D N8D' O10' 37.0(4) . . . . ?
N5D' C2D N8D' O10' 162.4(3) . . . . ?
N8D C2D N8D' O9D' -28.8(6) . . . . ?
N5D C2D N8D' O9D' -16.2(4) . . . . ?
C1D C2D N8D' O9D' -141.8(3) . . . . ?
N5D' C2D N8D' O9D' -16.4(5) . . . . ?
N3E C1E C2E N5E -144.02(15) . . . . ?
N4E C1E C2E N5E 37.5(2) . . . . ?
N3E C1E C2E N8E 97.66(16) . . . . ?
N4E C1E C2E N8E -80.77(18) . . . . ?
N8E C2E N5E O7E -140.80(14) . . . . ?
C1E C2E N5E O7E 98.47(17) . . . . ?
N8E C2E N5E O6E 39.57(17) . . . . ?
C1E C2E N5E O6E -81.16(17) . . . . ?
N5E C2E N8E O9E 52.01(17) . . . . ?
C1E C2E N8E O9E 174.06(14) . . . . ?
N5E C2E N8E O10E -130.07(15) . . . . ?
C1E C2E N8E O10E -8.03(19) . . . . ?
N4F C1F C2F N8F 47.91(19) . . . . ?
N3F C1F C2F N8F -132.88(14) . . . . ?
N4F C1F C2F N5F -72.60(18) . . . . ?
N3F C1F C2F N5F 106.60(16) . . . . ?
N8F C2F N5F O6F 23.76(19) . . . . ?
C1F C2F N5F O6F 148.29(15) . . . . ?
N8F C2F N5F O7F -160.45(15) . . . . ?
C1F C2F N5F O7F -35.9(2) . . . . ?
C1F C2F N8F O10F -53.38(18) . . . . ?
N5F C2F N8F O10F 69.59(17) . . . . ?
C1F C2F N8F O9F 128.44(14) . . . . ?
N5F C2F N8F O9F -108.59(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
N3A H3AA O1D 0.88 2.22 2.933(2) 138.5 1_655
N3A H3AB O4C 0.88 2.03 2.879(2) 161.1 .
N4A H4AA O4E 0.88 2.12 2.8797(17) 144.7 1_655
N4A H4AB O4D 0.88 2.05 2.8940(19) 160.1 2_655
N3B H3BA O3A 0.88 2.01 2.8902(18) 174.3 2_666
N3B H3BB O3E 0.88 2.34 3.0467(19) 137.9 .
N4B H4BA O1A 0.88 2.12 2.9905(19) 171.0 2_666
N4B H4BB O2B 0.88 2.21 2.998(2) 149.5 2_666
N3C H3CA O1F 0.88 2.30 3.140(2) 160.4 2_665
N3C H3CB O3C 0.88 2.06 2.8972(17) 159.8 1_565
N4C H4CA O3F 0.88 2.01 2.859(2) 162.7 2_665
N4C H4CB O2E 0.88 2.03 2.9010(19) 168.1 .
N3D H3DA O1C 0.88 2.16 3.029(2) 167.4 2_656
N3D H3DB O4A 0.88 2.16 2.953(2) 149.9 .
N4D H4DA O2C 0.88 2.13 2.974(2) 160.8 2_656
N4D H4DB O3B 0.88 2.09 2.9029(18) 152.4 1_445
N3E H3EA O1B 0.88 2.18 3.012(2) 157.8 .
N3E H3EB O4F 0.88 2.11 2.950(2) 158.9 .
N4E H4EA O4B 0.88 2.10 2.906(2) 152.8 .
N4E H4EB O2D 0.88 2.20 2.9351(19) 141.3 1_665
N3F H3FA O1D 0.88 1.97 2.8458(18) 175.5 .
N3F H3FB O2F 0.88 2.25 2.954(2) 136.7 .
N4F H4FA O3D 0.88 2.15 3.0006(17) 161.1 .
N4F H4FB O2A 0.88 2.13 2.904(2) 146.2 .

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.158
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_shrv192
_database_code_depnum_ccdc_archive 'CCDC 1008328'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;

_audit_creation_date             2012-05-08
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
; 
 2,2-dinitroacetohydrazonammonium trifluoromethanesulfonate acetonitrile 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H6 N5 O4 1+, C1 F3 O3 S1 1-, C2 H3 N1'
_chemical_formula_sum            'C5 H9 F3 N6 O7 S'
_chemical_formula_weight         354.24

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.2235(9)
_cell_length_b                   10.5855(15)
_cell_length_c                   11.8361(17)
_cell_angle_alpha                111.318(2)
_cell_angle_beta                 93.653(2)
_cell_angle_gamma                102.778(2)
_cell_volume                     699.44(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.8344
_exptl_absorpt_correction_T_max  0.9258

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            6266
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.47
_reflns_number_total             2825
_reflns_number_gt                2487
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_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     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.2732P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2825
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4443(3) 0.46417(17) 0.76176(15) 0.0232(3) Uani 1 1 d . . .
H1 H 0.4492 0.3848 0.7878 0.028 Uiso 1 1 calc R . .
C2 C 0.5815(3) 0.60001(16) 0.86199(14) 0.0196(3) Uani 1 1 d . . .
N3 N 0.2052(2) 0.46959(15) 0.74307(14) 0.0277(3) Uani 1 1 d . . .
O4 O 0.1068(2) 0.46770(16) 0.82792(14) 0.0421(4) Uani 1 1 d . . .
O5 O 0.1307(2) 0.47577(17) 0.64887(14) 0.0436(4) Uani 1 1 d . . .
N6 N 0.5274(3) 0.43469(17) 0.63947(14) 0.0324(4) Uani 1 1 d . . .
O7 O 0.4458(3) 0.31569(16) 0.56321(14) 0.0587(5) Uani 1 1 d . . .
O8 O 0.6618(3) 0.52628(18) 0.62543(13) 0.0472(4) Uani 1 1 d . . .
N9 N 0.7242(3) 0.58442(17) 0.94071(14) 0.0255(3) Uani 1 1 d . . .
H9A H 0.731(3) 0.502(2) 0.9287(19) 0.031 Uiso 1 1 d . . .
H9B H 0.812(4) 0.654(2) 0.996(2) 0.031 Uiso 1 1 d . . .
N10 N 0.5354(2) 0.71066(14) 0.85573(12) 0.0219(3) Uani 1 1 d . . .
N11 N 0.6708(3) 0.83968(15) 0.95101(14) 0.0215(3) Uani 1 1 d . . .
H11C H 0.814(4) 0.845(2) 0.9563(18) 0.026 Uiso 1 1 d . . .
H11B H 0.649(3) 0.905(2) 0.9314(18) 0.026 Uiso 1 1 d . . .
H11A H 0.624(3) 0.850(2) 1.0218(19) 0.026 Uiso 1 1 d . . .
C12 C 0.3003(3) 0.9125(2) 1.32857(16) 0.0329(4) Uani 1 1 d . . .
F13 F 0.1775(3) 0.82159(16) 1.36708(11) 0.0578(4) Uani 1 1 d . . .
F14 F 0.5125(2) 0.93317(14) 1.37176(11) 0.0505(3) Uani 1 1 d . . .
F15 F 0.2465(3) 1.03276(14) 1.37475(12) 0.0584(4) Uani 1 1 d . . .
S16 S 0.25865(6) 0.84542(4) 1.16152(3) 0.01912(12) Uani 1 1 d . . .
O17 O 0.02440(19) 0.82653(13) 1.12848(11) 0.0283(3) Uani 1 1 d . . .
O18 O 0.4046(2) 0.95625(12) 1.13706(11) 0.0274(3) Uani 1 1 d . . .
O19 O 0.3329(2) 0.71882(13) 1.12568(12) 0.0318(3) Uani 1 1 d . . .
C21 C 0.1151(3) 0.82112(19) 0.76132(17) 0.0297(4) Uani 1 1 d . . .
C20 C 0.1515(4) 0.7719(2) 0.63448(19) 0.0485(6) Uani 1 1 d . . .
H20A H 0.3007 0.7562 0.6304 0.058 Uiso 1 1 calc R . .
H20B H 0.1393 0.8427 0.6010 0.058 Uiso 1 1 calc R . .
H20C H 0.0390 0.6837 0.5863 0.058 Uiso 1 1 calc R . .
N22 N 0.0869(3) 0.86050(19) 0.86016(15) 0.0375(4) 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 N3 1.507(2) . ?
C1 C2 1.514(2) . ?
C1 N6 1.516(2) . ?
C1 H1 1.0000 . ?
C2 N10 1.292(2) . ?
C2 N9 1.325(2) . ?
N3 O5 1.209(2) . ?
N3 O4 1.213(2) . ?
N6 O8 1.202(2) . ?
N6 O7 1.221(2) . ?
N9 H9A 0.84(2) . ?
N9 H9B 0.83(2) . ?
N10 N11 1.4482(19) . ?
N11 H11C 0.88(2) . ?
N11 H11B 0.84(2) . ?
N11 H11A 0.88(2) . ?
C12 F15 1.318(2) . ?
C12 F13 1.325(2) . ?
C12 F14 1.326(2) . ?
C12 S16 1.8202(18) . ?
S16 O17 1.4352(12) . ?
S16 O19 1.4404(12) . ?
S16 O18 1.4473(12) . ?
C21 N22 1.130(2) . ?
C21 C20 1.450(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
N3 C1 C2 109.80(13) . . ?
N3 C1 N6 107.87(13) . . ?
C2 C1 N6 113.06(14) . . ?
N3 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
N6 C1 H1 108.7 . . ?
N10 C2 N9 131.67(16) . . ?
N10 C2 C1 113.51(14) . . ?
N9 C2 C1 114.81(14) . . ?
O5 N3 O4 126.67(16) . . ?
O5 N3 C1 119.00(15) . . ?
O4 N3 C1 114.32(14) . . ?
O8 N6 O7 126.33(18) . . ?
O8 N6 C1 119.30(15) . . ?
O7 N6 C1 114.37(17) . . ?
C2 N9 H9A 117.4(14) . . ?
C2 N9 H9B 120.5(14) . . ?
H9A N9 H9B 122(2) . . ?
C2 N10 N11 112.75(13) . . ?
N10 N11 H11C 112.9(13) . . ?
N10 N11 H11B 106.1(14) . . ?
H11C N11 H11B 108.1(19) . . ?
N10 N11 H11A 109.9(14) . . ?
H11C N11 H11A 111.7(18) . . ?
H11B N11 H11A 107.8(18) . . ?
F15 C12 F13 108.67(17) . . ?
F15 C12 F14 108.49(16) . . ?
F13 C12 F14 107.91(16) . . ?
F15 C12 S16 110.85(13) . . ?
F13 C12 S16 110.85(13) . . ?
F14 C12 S16 109.99(13) . . ?
O17 S16 O19 115.82(8) . . ?
O17 S16 O18 115.24(7) . . ?
O19 S16 O18 112.79(8) . . ?
O17 S16 C12 103.69(8) . . ?
O19 S16 C12 104.22(8) . . ?
O18 S16 C12 103.00(8) . . ?
N22 C21 C20 179.4(2) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
N3 C1 C2 N10 -42.01(19) . . . . ?
N6 C1 C2 N10 78.50(18) . . . . ?
N3 C1 C2 N9 137.17(15) . . . . ?
N6 C1 C2 N9 -102.31(17) . . . . ?
C2 C1 N3 O5 110.94(17) . . . . ?
N6 C1 N3 O5 -12.7(2) . . . . ?
C2 C1 N3 O4 -68.78(18) . . . . ?
N6 C1 N3 O4 167.61(15) . . . . ?
N3 C1 N6 O8 109.22(18) . . . . ?
C2 C1 N6 O8 -12.4(2) . . . . ?
N3 C1 N6 O7 -70.51(19) . . . . ?
C2 C1 N6 O7 167.88(16) . . . . ?
N9 C2 N10 N11 2.0(3) . . . . ?
C1 C2 N10 N11 -179.02(13) . . . . ?
F15 C12 S16 O17 -60.81(16) . . . . ?
F13 C12 S16 O17 59.96(16) . . . . ?
F14 C12 S16 O17 179.21(12) . . . . ?
F15 C12 S16 O19 177.57(14) . . . . ?
F13 C12 S16 O19 -61.65(16) . . . . ?
F14 C12 S16 O19 57.60(15) . . . . ?
F15 C12 S16 O18 59.63(16) . . . . ?
F13 C12 S16 O18 -179.60(14) . . . . ?
F14 C12 S16 O18 -60.35(14) . . . . ?

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
N9 H9A O19 0.84(2) 2.12(2) 2.945(2) 166(2) 2_667
N9 H9B O17 0.83(2) 2.03(2) 2.865(2) 179(2) 1_655
N11 H11A O18 0.88(2) 2.19(2) 2.917(2) 140.0(17) .
N11 H11B O18 0.84(2) 1.99(2) 2.828(2) 172.7(19) 2_677
N11 H11C N22 0.88(2) 2.12(2) 2.861(2) 142.7(17) 1_655

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.052
