# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145
#TrackingRef 'shrv162-final.cif'

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

_audit_creation_date             2011-05-10
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_audit_update_record             
;

;

#===========================================================================
# 1. SUBMISSION DETAILS
#===========================================================================

_publ_contact_author_name        'Dr Damon A. Parrish'

_publ_contact_author_address     
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;

_publ_contact_author_email       damon.parrish@nrl.navy.mil
_publ_contact_author_fax         202-767-6874
_publ_contact_author_phone       202-404-2141
_publ_requested_category         ?
_publ_requested_coeditor_name    ?

_publ_contact_letter             
;
;

#===========================================================================
# 2. PROCESSING SUMMARY (IUCr Office Use Only)
# Do NOT alter anthing in this section.
#===========================================================================
_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
; ?
;
_journal_techeditor_code         ?
_journal_techeditor_notes        
; ?
;
_journal_coden_ASTM              ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#===========================================================================
# 3. TITLE AND AUTHOR LIST
#===========================================================================

_publ_section_title              
;
title
;

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
"Jean'ne M. Shreeve"
;
Laboratory for the Structure of Matter, Code 6910
Naval Research Laboratory
Washington, DC 20375
;
?
'Zanqiang Zhang'
;
Chemsitry Department
University of Idaho
Moscow, ID, 83843
;
?
'Damon A. Parrish'
;
Chemsitry Department
University of Idaho
Moscow, ID, 83843
;
?

#===========================================================================
# 4. TEXT
#===========================================================================

_publ_section_abstract           
;

;

_publ_section_comment            
;
;

_publ_section_exptl_prep         
;
;

_publ_section_exptl_refinement   
;
;

_publ_section_references         
;
Bruker (2009). APEX2 v2010.3-0. Bruker AXS Inc., Madison, Wisconsin,
USA.

Bruker (2009). SAINT v7.68A. Bruker AXS Inc., Madison, Wisconsin,
USA.

Bruker (2008). SADABS v2008/1, Bruker AXS Inc., Madison, Wisconsin,
USA.

Bruker (2008). XPREP v2008/2. Bruker AXS Inc., Madison, Wisconsin,
USA.

Bruker (2008). SHELXTL v2008/4. Bruker AXS Inc., Madison, Wisconsin,
USA.
;

_publ_section_figure_captions    
;
;

_publ_section_table_legends      
;
;

_publ_section_acknowledgements   
;
Crystallographic studies were supported in part by the Office of Naval
Research (ONR) and the Naval Research Laboratory (NRL).
;

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

data_shrv162
_database_code_depnum_ccdc_archive 'CCDC 863655'
#TrackingRef 'shrv162-final.cif'

_audit_creation_date             2011-05-10
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
;
ammonium 3,4,5-trinitro-1H-pyrazol-1-olate ethyl acetate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'N1 H4 1+, C3 N5 O7 1-, C4 H8 O2'
_chemical_formula_sum            'C7 H12 N6 O9'
_chemical_formula_weight         324.23

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'

_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                   4.9047(19)
_cell_length_b                   10.001(4)
_cell_length_c                   14.952(6)
_cell_angle_alpha                80.849(5)
_cell_angle_beta                 84.181(5)
_cell_angle_gamma                78.460(6)
_cell_volume                     707.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.8993
_exptl_absorpt_correction_T_max  0.9643

_exptl_special_details           
;
?
;

_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       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6393
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.46
_reflns_number_total             2863
_reflns_number_gt                2354
_reflns_threshold_expression     I>2\s(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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0651P)^2^+0.1589P] where P=(Fo^2^+2Fc^2^)/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         2863
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N1 N 0.7000(3) 0.76039(13) 0.92775(8) 0.0357(3) Uani 1 1 d . . .
N2 N 0.4851(3) 0.86003(13) 0.94333(9) 0.0391(3) Uani 1 1 d . . .
C3 C 0.5163(3) 0.96507(16) 0.87679(10) 0.0367(3) Uani 1 1 d . . .
C4 C 0.7451(3) 0.93374(16) 0.81847(10) 0.0364(3) Uani 1 1 d . . .
C5 C 0.8641(3) 0.79998(16) 0.85240(10) 0.0366(3) Uani 1 1 d . . .
O6 O 0.7359(3) 0.64388(11) 0.98165(8) 0.0439(3) Uani 1 1 d . . .
N7 N 0.3287(3) 1.09505(14) 0.87766(9) 0.0431(3) Uani 1 1 d . . .
O8 O 0.1111(3) 1.09867(14) 0.92564(10) 0.0570(4) Uani 1 1 d . . .
O9 O 0.4019(3) 1.19498(13) 0.83013(9) 0.0583(4) Uani 1 1 d . . .
N10 N 0.8322(3) 1.01786(15) 0.73566(9) 0.0449(4) Uani 1 1 d . . .
O11 O 0.6953(4) 1.03052(19) 0.67165(9) 0.0758(5) Uani 1 1 d . . .
O12 O 1.0278(4) 1.0720(2) 0.73560(11) 0.0972(7) Uani 1 1 d . . .
N13 N 1.1129(3) 0.71563(16) 0.82024(10) 0.0470(4) Uani 1 1 d . . .
O14 O 1.2241(3) 0.76432(18) 0.74905(11) 0.0772(5) Uani 1 1 d . . .
O15 O 1.2026(3) 0.60467(15) 0.86444(11) 0.0676(4) Uani 1 1 d . . .
O16 O 0.2020(4) 0.4713(2) 1.27933(11) 0.0833(5) Uani 1 1 d . . .
C17 C 0.3210(5) 0.4787(2) 1.34418(14) 0.0650(6) Uani 1 1 d . . .
O18 O 0.3296(4) 0.38639(18) 1.41779(10) 0.0821(5) Uani 1 1 d . . .
C19 C 0.1939(9) 0.2698(4) 1.4174(2) 0.1154(13) Uani 1 1 d . . .
H19A H 0.0004 0.3030 1.4042 0.138 Uiso 1 1 calc R . .
H19B H 0.2850 0.2166 1.3702 0.138 Uiso 1 1 calc R . .
C20 C 0.2070(12) 0.1858(5) 1.5014(3) 0.157(2) Uani 1 1 d . . .
H20A H 0.1058 0.1130 1.5015 0.235 Uiso 1 1 calc R . .
H20B H 0.1258 0.2398 1.5484 0.235 Uiso 1 1 calc R . .
H20C H 0.3982 0.1470 1.5121 0.235 Uiso 1 1 calc R . .
C21 C 0.4801(8) 0.5873(3) 1.3514(2) 0.1010(10) Uani 1 1 d . . .
H21A H 0.3599 0.6760 1.3424 0.151 Uiso 1 1 calc R . .
H21B H 0.6333 0.5842 1.3059 0.151 Uiso 1 1 calc R . .
H21C H 0.5503 0.5721 1.4105 0.151 Uiso 1 1 calc R . .
N22 N 0.2305(4) 0.60718(17) 1.09505(11) 0.0449(4) Uani 1 1 d . . .
H22A H 0.227(5) 0.580(2) 1.1596(17) 0.067 Uiso 1 1 d . . .
H22B H 0.391(6) 0.633(2) 1.0656(16) 0.067 Uiso 1 1 d . . .
H22C H 0.183(5) 0.544(3) 1.0712(16) 0.067 Uiso 1 1 d . . .
H22D H 0.106(6) 0.671(3) 1.0892(16) 0.067 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0385(7) 0.0306(6) 0.0364(6) 0.0010(5) -0.0033(5) -0.0071(5)
N2 0.0414(7) 0.0324(7) 0.0407(7) -0.0004(5) 0.0010(6) -0.0057(6)
C3 0.0401(8) 0.0305(8) 0.0380(8) 0.0005(6) -0.0046(6) -0.0061(6)
C4 0.0380(8) 0.0361(8) 0.0347(7) 0.0027(6) -0.0056(6) -0.0108(6)
C5 0.0369(8) 0.0359(8) 0.0358(8) -0.0010(6) -0.0026(6) -0.0071(6)
O6 0.0518(7) 0.0304(6) 0.0445(6) 0.0082(5) -0.0028(5) -0.0068(5)
N7 0.0499(8) 0.0324(7) 0.0443(7) -0.0011(6) -0.0048(6) -0.0045(6)
O8 0.0509(8) 0.0478(7) 0.0633(8) -0.0041(6) 0.0079(6) 0.0031(6)
O9 0.0745(9) 0.0329(6) 0.0626(8) 0.0048(6) -0.0003(7) -0.0096(6)
N10 0.0487(8) 0.0458(8) 0.0379(7) 0.0056(6) -0.0029(6) -0.0126(7)
O11 0.0918(12) 0.0949(12) 0.0442(7) 0.0153(7) -0.0224(8) -0.0371(10)
O12 0.0968(13) 0.1392(17) 0.0677(10) 0.0377(10) -0.0224(9) -0.0837(13)
N13 0.0390(8) 0.0490(9) 0.0486(8) -0.0019(7) 0.0014(6) -0.0044(7)
O14 0.0600(9) 0.0834(11) 0.0673(9) 0.0111(8) 0.0237(7) 0.0053(8)
O15 0.0568(8) 0.0520(8) 0.0764(10) 0.0093(7) 0.0048(7) 0.0126(7)
O16 0.0773(11) 0.1070(14) 0.0534(9) 0.0182(9) -0.0066(8) -0.0108(10)
C17 0.0682(14) 0.0653(13) 0.0501(11) 0.0097(10) 0.0039(10) -0.0035(11)
O18 0.1270(15) 0.0724(11) 0.0503(8) 0.0157(7) -0.0195(9) -0.0395(11)
C19 0.179(4) 0.107(2) 0.0783(18) 0.0220(16) -0.033(2) -0.085(3)
C20 0.255(6) 0.126(3) 0.108(3) 0.031(2) -0.024(3) -0.113(4)
C21 0.135(3) 0.0740(18) 0.0881(19) 0.0179(15) -0.0042(18) -0.0317(19)
N22 0.0451(9) 0.0413(8) 0.0448(8) -0.0007(7) -0.0026(7) -0.0046(7)

_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
N1 O6 1.2985(17) . ?
N1 N2 1.327(2) . ?
N1 C5 1.370(2) . ?
N2 C3 1.348(2) . ?
C3 C4 1.366(2) . ?
C3 N7 1.436(2) . ?
C4 C5 1.385(2) . ?
C4 N10 1.459(2) . ?
C5 N13 1.425(2) . ?
N7 O8 1.222(2) . ?
N7 O9 1.2241(19) . ?
N10 O12 1.192(2) . ?
N10 O11 1.200(2) . ?
N13 O14 1.221(2) . ?
N13 O15 1.222(2) . ?
O16 C17 1.200(3) . ?
C17 O18 1.317(2) . ?
C17 C21 1.481(4) . ?
O18 C19 1.455(3) . ?
C19 C20 1.395(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N22 H22A 0.96(3) . ?
N22 H22B 0.93(3) . ?
N22 H22C 0.86(3) . ?
N22 H22D 0.79(3) . ?

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
O6 N1 N2 120.53(13) . . ?
O6 N1 C5 128.05(13) . . ?
N2 N1 C5 111.41(13) . . ?
N1 N2 C3 104.69(13) . . ?
N2 C3 C4 112.80(14) . . ?
N2 C3 N7 119.31(14) . . ?
C4 C3 N7 127.73(14) . . ?
C3 C4 C5 104.11(13) . . ?
C3 C4 N10 127.90(15) . . ?
C5 C4 N10 127.85(15) . . ?
N1 C5 C4 106.98(14) . . ?
N1 C5 N13 124.06(14) . . ?
C4 C5 N13 128.93(14) . . ?
O8 N7 O9 124.85(15) . . ?
O8 N7 C3 118.41(14) . . ?
O9 N7 C3 116.74(15) . . ?
O12 N10 O11 123.93(16) . . ?
O12 N10 C4 119.14(14) . . ?
O11 N10 C4 116.91(14) . . ?
O14 N13 O15 124.92(16) . . ?
O14 N13 C5 115.20(15) . . ?
O15 N13 C5 119.86(15) . . ?
O16 C17 O18 122.8(2) . . ?
O16 C17 C21 125.4(2) . . ?
O18 C17 C21 111.8(2) . . ?
C17 O18 C19 117.3(2) . . ?
C20 C19 O18 110.5(3) . . ?
C20 C19 H19A 109.6 . . ?
O18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
O18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A N22 H22B 118(2) . . ?
H22A N22 H22C 108(2) . . ?
H22B N22 H22C 112(2) . . ?
H22A N22 H22D 103(2) . . ?
H22B N22 H22D 109(2) . . ?
H22C N22 H22D 106(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 N1 N2 C3 178.49(13) . . . . ?
C5 N1 N2 C3 -0.58(17) . . . . ?
N1 N2 C3 C4 0.73(18) . . . . ?
N1 N2 C3 N7 -175.01(13) . . . . ?
N2 C3 C4 C5 -0.58(18) . . . . ?
N7 C3 C4 C5 174.72(15) . . . . ?
N2 C3 C4 N10 175.26(14) . . . . ?
N7 C3 C4 N10 -9.4(3) . . . . ?
O6 N1 C5 C4 -178.74(14) . . . . ?
N2 N1 C5 C4 0.25(17) . . . . ?
O6 N1 C5 N13 -0.4(2) . . . . ?
N2 N1 C5 N13 178.54(14) . . . . ?
C3 C4 C5 N1 0.20(17) . . . . ?
N10 C4 C5 N1 -175.65(14) . . . . ?
C3 C4 C5 N13 -177.99(16) . . . . ?
N10 C4 C5 N13 6.2(3) . . . . ?
N2 C3 N7 O8 -16.2(2) . . . . ?
C4 C3 N7 O8 168.75(16) . . . . ?
N2 C3 N7 O9 163.17(15) . . . . ?
C4 C3 N7 O9 -11.9(2) . . . . ?
C3 C4 N10 O12 106.7(2) . . . . ?
C5 C4 N10 O12 -78.4(3) . . . . ?
C3 C4 N10 O11 -71.7(2) . . . . ?
C5 C4 N10 O11 103.2(2) . . . . ?
N1 C5 N13 O14 175.86(16) . . . . ?
C4 C5 N13 O14 -6.2(3) . . . . ?
N1 C5 N13 O15 -5.6(3) . . . . ?
C4 C5 N13 O15 172.28(17) . . . . ?
O16 C17 O18 C19 1.7(4) . . . . ?
C21 C17 O18 C19 -176.7(3) . . . . ?
C17 O18 C19 C20 -176.6(4) . . . . ?

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
N22 H22A O16 0.96(3) 1.95(3) 2.875(2) 162(2) .
N22 H22B O6 0.93(3) 2.01(3) 2.910(2) 163(2) .
N22 H22C O6 0.86(3) 2.10(3) 2.891(2) 153(2) 2_667

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        26.46
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044

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

data_shrv162
_database_code_depnum_ccdc_archive 'CCDC 863656'
#TrackingRef 'shrv162-final.cif'

_audit_creation_date             2011-05-10
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
;
ammonium 3,4,5-trinitro-1H-pyrazol-1-olate ethyl acetate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'N1 H4 1+, C3 N5 O7 1-, C4 H8 O2'
_chemical_formula_sum            'C7 H12 N6 O9'
_chemical_formula_weight         324.23

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'

_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                   4.9047(19)
_cell_length_b                   10.001(4)
_cell_length_c                   14.952(6)
_cell_angle_alpha                80.849(5)
_cell_angle_beta                 84.181(5)
_cell_angle_gamma                78.460(6)
_cell_volume                     707.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.8993
_exptl_absorpt_correction_T_max  0.9643

_exptl_special_details           
;
?
;

_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       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6393
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.46
_reflns_number_total             2863
_reflns_number_gt                2354
_reflns_threshold_expression     I>2\s(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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0651P)^2^+0.1589P] where P=(Fo^2^+2Fc^2^)/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         2863
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N1 N 0.7000(3) 0.76039(13) 0.92775(8) 0.0357(3) Uani 1 1 d . . .
N2 N 0.4851(3) 0.86003(13) 0.94333(9) 0.0391(3) Uani 1 1 d . . .
C3 C 0.5163(3) 0.96507(16) 0.87679(10) 0.0367(3) Uani 1 1 d . . .
C4 C 0.7451(3) 0.93374(16) 0.81847(10) 0.0364(3) Uani 1 1 d . . .
C5 C 0.8641(3) 0.79998(16) 0.85240(10) 0.0366(3) Uani 1 1 d . . .
O6 O 0.7359(3) 0.64388(11) 0.98165(8) 0.0439(3) Uani 1 1 d . . .
N7 N 0.3287(3) 1.09505(14) 0.87766(9) 0.0431(3) Uani 1 1 d . . .
O8 O 0.1111(3) 1.09867(14) 0.92564(10) 0.0570(4) Uani 1 1 d . . .
O9 O 0.4019(3) 1.19498(13) 0.83013(9) 0.0583(4) Uani 1 1 d . . .
N10 N 0.8322(3) 1.01786(15) 0.73566(9) 0.0449(4) Uani 1 1 d . . .
O11 O 0.6953(4) 1.03052(19) 0.67165(9) 0.0758(5) Uani 1 1 d . . .
O12 O 1.0278(4) 1.0720(2) 0.73560(11) 0.0972(7) Uani 1 1 d . . .
N13 N 1.1129(3) 0.71563(16) 0.82024(10) 0.0470(4) Uani 1 1 d . . .
O14 O 1.2241(3) 0.76432(18) 0.74905(11) 0.0772(5) Uani 1 1 d . . .
O15 O 1.2026(3) 0.60467(15) 0.86444(11) 0.0676(4) Uani 1 1 d . . .
O16 O 0.2020(4) 0.4713(2) 1.27933(11) 0.0833(5) Uani 1 1 d . . .
C17 C 0.3210(5) 0.4787(2) 1.34418(14) 0.0650(6) Uani 1 1 d . . .
O18 O 0.3296(4) 0.38639(18) 1.41779(10) 0.0821(5) Uani 1 1 d . . .
C19 C 0.1939(9) 0.2698(4) 1.4174(2) 0.1154(13) Uani 1 1 d . . .
H19A H 0.0004 0.3030 1.4042 0.138 Uiso 1 1 calc R . .
H19B H 0.2850 0.2166 1.3702 0.138 Uiso 1 1 calc R . .
C20 C 0.2070(12) 0.1858(5) 1.5014(3) 0.157(2) Uani 1 1 d . . .
H20A H 0.1058 0.1130 1.5015 0.235 Uiso 1 1 calc R . .
H20B H 0.1258 0.2398 1.5484 0.235 Uiso 1 1 calc R . .
H20C H 0.3982 0.1470 1.5121 0.235 Uiso 1 1 calc R . .
C21 C 0.4801(8) 0.5873(3) 1.3514(2) 0.1010(10) Uani 1 1 d . . .
H21A H 0.3599 0.6760 1.3424 0.151 Uiso 1 1 calc R . .
H21B H 0.6333 0.5842 1.3059 0.151 Uiso 1 1 calc R . .
H21C H 0.5503 0.5721 1.4105 0.151 Uiso 1 1 calc R . .
N22 N 0.2305(4) 0.60718(17) 1.09505(11) 0.0449(4) Uani 1 1 d . . .
H22A H 0.227(5) 0.580(2) 1.1596(17) 0.067 Uiso 1 1 d . . .
H22B H 0.391(6) 0.633(2) 1.0656(16) 0.067 Uiso 1 1 d . . .
H22C H 0.183(5) 0.544(3) 1.0712(16) 0.067 Uiso 1 1 d . . .
H22D H 0.106(6) 0.671(3) 1.0892(16) 0.067 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0385(7) 0.0306(6) 0.0364(6) 0.0010(5) -0.0033(5) -0.0071(5)
N2 0.0414(7) 0.0324(7) 0.0407(7) -0.0004(5) 0.0010(6) -0.0057(6)
C3 0.0401(8) 0.0305(8) 0.0380(8) 0.0005(6) -0.0046(6) -0.0061(6)
C4 0.0380(8) 0.0361(8) 0.0347(7) 0.0027(6) -0.0056(6) -0.0108(6)
C5 0.0369(8) 0.0359(8) 0.0358(8) -0.0010(6) -0.0026(6) -0.0071(6)
O6 0.0518(7) 0.0304(6) 0.0445(6) 0.0082(5) -0.0028(5) -0.0068(5)
N7 0.0499(8) 0.0324(7) 0.0443(7) -0.0011(6) -0.0048(6) -0.0045(6)
O8 0.0509(8) 0.0478(7) 0.0633(8) -0.0041(6) 0.0079(6) 0.0031(6)
O9 0.0745(9) 0.0329(6) 0.0626(8) 0.0048(6) -0.0003(7) -0.0096(6)
N10 0.0487(8) 0.0458(8) 0.0379(7) 0.0056(6) -0.0029(6) -0.0126(7)
O11 0.0918(12) 0.0949(12) 0.0442(7) 0.0153(7) -0.0224(8) -0.0371(10)
O12 0.0968(13) 0.1392(17) 0.0677(10) 0.0377(10) -0.0224(9) -0.0837(13)
N13 0.0390(8) 0.0490(9) 0.0486(8) -0.0019(7) 0.0014(6) -0.0044(7)
O14 0.0600(9) 0.0834(11) 0.0673(9) 0.0111(8) 0.0237(7) 0.0053(8)
O15 0.0568(8) 0.0520(8) 0.0764(10) 0.0093(7) 0.0048(7) 0.0126(7)
O16 0.0773(11) 0.1070(14) 0.0534(9) 0.0182(9) -0.0066(8) -0.0108(10)
C17 0.0682(14) 0.0653(13) 0.0501(11) 0.0097(10) 0.0039(10) -0.0035(11)
O18 0.1270(15) 0.0724(11) 0.0503(8) 0.0157(7) -0.0195(9) -0.0395(11)
C19 0.179(4) 0.107(2) 0.0783(18) 0.0220(16) -0.033(2) -0.085(3)
C20 0.255(6) 0.126(3) 0.108(3) 0.031(2) -0.024(3) -0.113(4)
C21 0.135(3) 0.0740(18) 0.0881(19) 0.0179(15) -0.0042(18) -0.0317(19)
N22 0.0451(9) 0.0413(8) 0.0448(8) -0.0007(7) -0.0026(7) -0.0046(7)

_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
N1 O6 1.2985(17) . ?
N1 N2 1.327(2) . ?
N1 C5 1.370(2) . ?
N2 C3 1.348(2) . ?
C3 C4 1.366(2) . ?
C3 N7 1.436(2) . ?
C4 C5 1.385(2) . ?
C4 N10 1.459(2) . ?
C5 N13 1.425(2) . ?
N7 O8 1.222(2) . ?
N7 O9 1.2241(19) . ?
N10 O12 1.192(2) . ?
N10 O11 1.200(2) . ?
N13 O14 1.221(2) . ?
N13 O15 1.222(2) . ?
O16 C17 1.200(3) . ?
C17 O18 1.317(2) . ?
C17 C21 1.481(4) . ?
O18 C19 1.455(3) . ?
C19 C20 1.395(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N22 H22A 0.96(3) . ?
N22 H22B 0.93(3) . ?
N22 H22C 0.86(3) . ?
N22 H22D 0.79(3) . ?

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
O6 N1 N2 120.53(13) . . ?
O6 N1 C5 128.05(13) . . ?
N2 N1 C5 111.41(13) . . ?
N1 N2 C3 104.69(13) . . ?
N2 C3 C4 112.80(14) . . ?
N2 C3 N7 119.31(14) . . ?
C4 C3 N7 127.73(14) . . ?
C3 C4 C5 104.11(13) . . ?
C3 C4 N10 127.90(15) . . ?
C5 C4 N10 127.85(15) . . ?
N1 C5 C4 106.98(14) . . ?
N1 C5 N13 124.06(14) . . ?
C4 C5 N13 128.93(14) . . ?
O8 N7 O9 124.85(15) . . ?
O8 N7 C3 118.41(14) . . ?
O9 N7 C3 116.74(15) . . ?
O12 N10 O11 123.93(16) . . ?
O12 N10 C4 119.14(14) . . ?
O11 N10 C4 116.91(14) . . ?
O14 N13 O15 124.92(16) . . ?
O14 N13 C5 115.20(15) . . ?
O15 N13 C5 119.86(15) . . ?
O16 C17 O18 122.8(2) . . ?
O16 C17 C21 125.4(2) . . ?
O18 C17 C21 111.8(2) . . ?
C17 O18 C19 117.3(2) . . ?
C20 C19 O18 110.5(3) . . ?
C20 C19 H19A 109.6 . . ?
O18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
O18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A N22 H22B 118(2) . . ?
H22A N22 H22C 108(2) . . ?
H22B N22 H22C 112(2) . . ?
H22A N22 H22D 103(2) . . ?
H22B N22 H22D 109(2) . . ?
H22C N22 H22D 106(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 N1 N2 C3 178.49(13) . . . . ?
C5 N1 N2 C3 -0.58(17) . . . . ?
N1 N2 C3 C4 0.73(18) . . . . ?
N1 N2 C3 N7 -175.01(13) . . . . ?
N2 C3 C4 C5 -0.58(18) . . . . ?
N7 C3 C4 C5 174.72(15) . . . . ?
N2 C3 C4 N10 175.26(14) . . . . ?
N7 C3 C4 N10 -9.4(3) . . . . ?
O6 N1 C5 C4 -178.74(14) . . . . ?
N2 N1 C5 C4 0.25(17) . . . . ?
O6 N1 C5 N13 -0.4(2) . . . . ?
N2 N1 C5 N13 178.54(14) . . . . ?
C3 C4 C5 N1 0.20(17) . . . . ?
N10 C4 C5 N1 -175.65(14) . . . . ?
C3 C4 C5 N13 -177.99(16) . . . . ?
N10 C4 C5 N13 6.2(3) . . . . ?
N2 C3 N7 O8 -16.2(2) . . . . ?
C4 C3 N7 O8 168.75(16) . . . . ?
N2 C3 N7 O9 163.17(15) . . . . ?
C4 C3 N7 O9 -11.9(2) . . . . ?
C3 C4 N10 O12 106.7(2) . . . . ?
C5 C4 N10 O12 -78.4(3) . . . . ?
C3 C4 N10 O11 -71.7(2) . . . . ?
C5 C4 N10 O11 103.2(2) . . . . ?
N1 C5 N13 O14 175.86(16) . . . . ?
C4 C5 N13 O14 -6.2(3) . . . . ?
N1 C5 N13 O15 -5.6(3) . . . . ?
C4 C5 N13 O15 172.28(17) . . . . ?
O16 C17 O18 C19 1.7(4) . . . . ?
C21 C17 O18 C19 -176.7(3) . . . . ?
C17 O18 C19 C20 -176.6(4) . . . . ?

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
N22 H22A O16 0.96(3) 1.95(3) 2.875(2) 162(2) .
N22 H22B O6 0.93(3) 2.01(3) 2.910(2) 163(2) .
N22 H22C O6 0.86(3) 2.10(3) 2.891(2) 153(2) 2_667

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        26.46
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044

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

data_shrv162
_database_code_depnum_ccdc_archive 'CCDC 863657'
#TrackingRef 'shrv162-final.cif'

_audit_creation_date             2011-05-10
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
;
ammonium 3,4,5-trinitro-1H-pyrazol-1-olate ethyl acetate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'N1 H4 1+, C3 N5 O7 1-, C4 H8 O2'
_chemical_formula_sum            'C7 H12 N6 O9'
_chemical_formula_weight         324.23

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'

_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                   4.9047(19)
_cell_length_b                   10.001(4)
_cell_length_c                   14.952(6)
_cell_angle_alpha                80.849(5)
_cell_angle_beta                 84.181(5)
_cell_angle_gamma                78.460(6)
_cell_volume                     707.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.8993
_exptl_absorpt_correction_T_max  0.9643

_exptl_special_details           
;
?
;

_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       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6393
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.46
_reflns_number_total             2863
_reflns_number_gt                2354
_reflns_threshold_expression     I>2\s(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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0651P)^2^+0.1589P] where P=(Fo^2^+2Fc^2^)/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         2863
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N1 N 0.7000(3) 0.76039(13) 0.92775(8) 0.0357(3) Uani 1 1 d . . .
N2 N 0.4851(3) 0.86003(13) 0.94333(9) 0.0391(3) Uani 1 1 d . . .
C3 C 0.5163(3) 0.96507(16) 0.87679(10) 0.0367(3) Uani 1 1 d . . .
C4 C 0.7451(3) 0.93374(16) 0.81847(10) 0.0364(3) Uani 1 1 d . . .
C5 C 0.8641(3) 0.79998(16) 0.85240(10) 0.0366(3) Uani 1 1 d . . .
O6 O 0.7359(3) 0.64388(11) 0.98165(8) 0.0439(3) Uani 1 1 d . . .
N7 N 0.3287(3) 1.09505(14) 0.87766(9) 0.0431(3) Uani 1 1 d . . .
O8 O 0.1111(3) 1.09867(14) 0.92564(10) 0.0570(4) Uani 1 1 d . . .
O9 O 0.4019(3) 1.19498(13) 0.83013(9) 0.0583(4) Uani 1 1 d . . .
N10 N 0.8322(3) 1.01786(15) 0.73566(9) 0.0449(4) Uani 1 1 d . . .
O11 O 0.6953(4) 1.03052(19) 0.67165(9) 0.0758(5) Uani 1 1 d . . .
O12 O 1.0278(4) 1.0720(2) 0.73560(11) 0.0972(7) Uani 1 1 d . . .
N13 N 1.1129(3) 0.71563(16) 0.82024(10) 0.0470(4) Uani 1 1 d . . .
O14 O 1.2241(3) 0.76432(18) 0.74905(11) 0.0772(5) Uani 1 1 d . . .
O15 O 1.2026(3) 0.60467(15) 0.86444(11) 0.0676(4) Uani 1 1 d . . .
O16 O 0.2020(4) 0.4713(2) 1.27933(11) 0.0833(5) Uani 1 1 d . . .
C17 C 0.3210(5) 0.4787(2) 1.34418(14) 0.0650(6) Uani 1 1 d . . .
O18 O 0.3296(4) 0.38639(18) 1.41779(10) 0.0821(5) Uani 1 1 d . . .
C19 C 0.1939(9) 0.2698(4) 1.4174(2) 0.1154(13) Uani 1 1 d . . .
H19A H 0.0004 0.3030 1.4042 0.138 Uiso 1 1 calc R . .
H19B H 0.2850 0.2166 1.3702 0.138 Uiso 1 1 calc R . .
C20 C 0.2070(12) 0.1858(5) 1.5014(3) 0.157(2) Uani 1 1 d . . .
H20A H 0.1058 0.1130 1.5015 0.235 Uiso 1 1 calc R . .
H20B H 0.1258 0.2398 1.5484 0.235 Uiso 1 1 calc R . .
H20C H 0.3982 0.1470 1.5121 0.235 Uiso 1 1 calc R . .
C21 C 0.4801(8) 0.5873(3) 1.3514(2) 0.1010(10) Uani 1 1 d . . .
H21A H 0.3599 0.6760 1.3424 0.151 Uiso 1 1 calc R . .
H21B H 0.6333 0.5842 1.3059 0.151 Uiso 1 1 calc R . .
H21C H 0.5503 0.5721 1.4105 0.151 Uiso 1 1 calc R . .
N22 N 0.2305(4) 0.60718(17) 1.09505(11) 0.0449(4) Uani 1 1 d . . .
H22A H 0.227(5) 0.580(2) 1.1596(17) 0.067 Uiso 1 1 d . . .
H22B H 0.391(6) 0.633(2) 1.0656(16) 0.067 Uiso 1 1 d . . .
H22C H 0.183(5) 0.544(3) 1.0712(16) 0.067 Uiso 1 1 d . . .
H22D H 0.106(6) 0.671(3) 1.0892(16) 0.067 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0385(7) 0.0306(6) 0.0364(6) 0.0010(5) -0.0033(5) -0.0071(5)
N2 0.0414(7) 0.0324(7) 0.0407(7) -0.0004(5) 0.0010(6) -0.0057(6)
C3 0.0401(8) 0.0305(8) 0.0380(8) 0.0005(6) -0.0046(6) -0.0061(6)
C4 0.0380(8) 0.0361(8) 0.0347(7) 0.0027(6) -0.0056(6) -0.0108(6)
C5 0.0369(8) 0.0359(8) 0.0358(8) -0.0010(6) -0.0026(6) -0.0071(6)
O6 0.0518(7) 0.0304(6) 0.0445(6) 0.0082(5) -0.0028(5) -0.0068(5)
N7 0.0499(8) 0.0324(7) 0.0443(7) -0.0011(6) -0.0048(6) -0.0045(6)
O8 0.0509(8) 0.0478(7) 0.0633(8) -0.0041(6) 0.0079(6) 0.0031(6)
O9 0.0745(9) 0.0329(6) 0.0626(8) 0.0048(6) -0.0003(7) -0.0096(6)
N10 0.0487(8) 0.0458(8) 0.0379(7) 0.0056(6) -0.0029(6) -0.0126(7)
O11 0.0918(12) 0.0949(12) 0.0442(7) 0.0153(7) -0.0224(8) -0.0371(10)
O12 0.0968(13) 0.1392(17) 0.0677(10) 0.0377(10) -0.0224(9) -0.0837(13)
N13 0.0390(8) 0.0490(9) 0.0486(8) -0.0019(7) 0.0014(6) -0.0044(7)
O14 0.0600(9) 0.0834(11) 0.0673(9) 0.0111(8) 0.0237(7) 0.0053(8)
O15 0.0568(8) 0.0520(8) 0.0764(10) 0.0093(7) 0.0048(7) 0.0126(7)
O16 0.0773(11) 0.1070(14) 0.0534(9) 0.0182(9) -0.0066(8) -0.0108(10)
C17 0.0682(14) 0.0653(13) 0.0501(11) 0.0097(10) 0.0039(10) -0.0035(11)
O18 0.1270(15) 0.0724(11) 0.0503(8) 0.0157(7) -0.0195(9) -0.0395(11)
C19 0.179(4) 0.107(2) 0.0783(18) 0.0220(16) -0.033(2) -0.085(3)
C20 0.255(6) 0.126(3) 0.108(3) 0.031(2) -0.024(3) -0.113(4)
C21 0.135(3) 0.0740(18) 0.0881(19) 0.0179(15) -0.0042(18) -0.0317(19)
N22 0.0451(9) 0.0413(8) 0.0448(8) -0.0007(7) -0.0026(7) -0.0046(7)

_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
N1 O6 1.2985(17) . ?
N1 N2 1.327(2) . ?
N1 C5 1.370(2) . ?
N2 C3 1.348(2) . ?
C3 C4 1.366(2) . ?
C3 N7 1.436(2) . ?
C4 C5 1.385(2) . ?
C4 N10 1.459(2) . ?
C5 N13 1.425(2) . ?
N7 O8 1.222(2) . ?
N7 O9 1.2241(19) . ?
N10 O12 1.192(2) . ?
N10 O11 1.200(2) . ?
N13 O14 1.221(2) . ?
N13 O15 1.222(2) . ?
O16 C17 1.200(3) . ?
C17 O18 1.317(2) . ?
C17 C21 1.481(4) . ?
O18 C19 1.455(3) . ?
C19 C20 1.395(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N22 H22A 0.96(3) . ?
N22 H22B 0.93(3) . ?
N22 H22C 0.86(3) . ?
N22 H22D 0.79(3) . ?

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
O6 N1 N2 120.53(13) . . ?
O6 N1 C5 128.05(13) . . ?
N2 N1 C5 111.41(13) . . ?
N1 N2 C3 104.69(13) . . ?
N2 C3 C4 112.80(14) . . ?
N2 C3 N7 119.31(14) . . ?
C4 C3 N7 127.73(14) . . ?
C3 C4 C5 104.11(13) . . ?
C3 C4 N10 127.90(15) . . ?
C5 C4 N10 127.85(15) . . ?
N1 C5 C4 106.98(14) . . ?
N1 C5 N13 124.06(14) . . ?
C4 C5 N13 128.93(14) . . ?
O8 N7 O9 124.85(15) . . ?
O8 N7 C3 118.41(14) . . ?
O9 N7 C3 116.74(15) . . ?
O12 N10 O11 123.93(16) . . ?
O12 N10 C4 119.14(14) . . ?
O11 N10 C4 116.91(14) . . ?
O14 N13 O15 124.92(16) . . ?
O14 N13 C5 115.20(15) . . ?
O15 N13 C5 119.86(15) . . ?
O16 C17 O18 122.8(2) . . ?
O16 C17 C21 125.4(2) . . ?
O18 C17 C21 111.8(2) . . ?
C17 O18 C19 117.3(2) . . ?
C20 C19 O18 110.5(3) . . ?
C20 C19 H19A 109.6 . . ?
O18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
O18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A N22 H22B 118(2) . . ?
H22A N22 H22C 108(2) . . ?
H22B N22 H22C 112(2) . . ?
H22A N22 H22D 103(2) . . ?
H22B N22 H22D 109(2) . . ?
H22C N22 H22D 106(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 N1 N2 C3 178.49(13) . . . . ?
C5 N1 N2 C3 -0.58(17) . . . . ?
N1 N2 C3 C4 0.73(18) . . . . ?
N1 N2 C3 N7 -175.01(13) . . . . ?
N2 C3 C4 C5 -0.58(18) . . . . ?
N7 C3 C4 C5 174.72(15) . . . . ?
N2 C3 C4 N10 175.26(14) . . . . ?
N7 C3 C4 N10 -9.4(3) . . . . ?
O6 N1 C5 C4 -178.74(14) . . . . ?
N2 N1 C5 C4 0.25(17) . . . . ?
O6 N1 C5 N13 -0.4(2) . . . . ?
N2 N1 C5 N13 178.54(14) . . . . ?
C3 C4 C5 N1 0.20(17) . . . . ?
N10 C4 C5 N1 -175.65(14) . . . . ?
C3 C4 C5 N13 -177.99(16) . . . . ?
N10 C4 C5 N13 6.2(3) . . . . ?
N2 C3 N7 O8 -16.2(2) . . . . ?
C4 C3 N7 O8 168.75(16) . . . . ?
N2 C3 N7 O9 163.17(15) . . . . ?
C4 C3 N7 O9 -11.9(2) . . . . ?
C3 C4 N10 O12 106.7(2) . . . . ?
C5 C4 N10 O12 -78.4(3) . . . . ?
C3 C4 N10 O11 -71.7(2) . . . . ?
C5 C4 N10 O11 103.2(2) . . . . ?
N1 C5 N13 O14 175.86(16) . . . . ?
C4 C5 N13 O14 -6.2(3) . . . . ?
N1 C5 N13 O15 -5.6(3) . . . . ?
C4 C5 N13 O15 172.28(17) . . . . ?
O16 C17 O18 C19 1.7(4) . . . . ?
C21 C17 O18 C19 -176.7(3) . . . . ?
C17 O18 C19 C20 -176.6(4) . . . . ?

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
N22 H22A O16 0.96(3) 1.95(3) 2.875(2) 162(2) .
N22 H22B O6 0.93(3) 2.01(3) 2.910(2) 163(2) .
N22 H22C O6 0.86(3) 2.10(3) 2.891(2) 153(2) 2_667

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        26.46
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044