# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_Cambridge         1145
_publ_contact_author_name        'J. M. Shreeve'
_publ_contact_author_address     
;
Department of Chemistry
University of Idaho
Box 442343
Moscow
ID
83844-2343
UNITED STATES OF AMERICA
;
_publ_contact_author_email       JSHREEVE@UIDAHO.EDU

loop_
_publ_author_name
_publ_author_address
Z.Zeng
;Department of Chemistry,
University of Idaho,
Moscow,
ID 83844-2343,
USA
;
H.Gao
;Department of Chemistry,
University of Idaho,
Moscow,
ID 83844-2343,
USA
;
B.Twamley
;Department of Chemistry,
University of Idaho,
Moscow,
ID 83844-2343,
USA
;
J.M.Shreeve
;Department of Chemistry,
University of Idaho,
Moscow,
ID 83844-2343,
USA
;
_publ_section_title              
;
Energetic mono- and di-basic
5-dinitromethyltetrazolates: synthesis, properties, and particle
processing
;

data_compound10 #####bt1030
_database_code_depnum_ccdc_archive 'CCDC 646498'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'C2HN6O4, C2H5N4, 2(C2H4N4), H2O'
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H N6 O4, C2 H5 N4, 2(C2 H4 N4), H2 O'
_chemical_formula_sum            'C8 H16 N18 O5'
_chemical_formula_weight         444.39

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           Monoclinic
_symmetry_space_group_name_H-M   Cc
_symmetry_space_group_name_Hall  'C -2yc'

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

_cell_length_a                   11.9753(8)
_cell_length_b                   23.2559(16)
_cell_length_c                   6.8413(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.3840(10)
_cell_angle_gamma                90.00
_cell_volume                     1786.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    6381
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      30.03

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS-2004/1 (Bruker, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker/Siemens SMART APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12564
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2372
_reflns_number_gt                2186
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART v. 5.632 (Bruker, 2006)'
_computing_cell_refinement       'SAINT+ v. 7.23a (Bruker, 2006)'
_computing_data_reduction        'SAINT+ v. 7.23a (Bruker, 2006)'
_computing_structure_solution    'XS, SHELXTL v. 6.14 (Bruker, 2003) '
_computing_structure_refinement  'XL,SHELXTL v. 6.14 (Bruker, 2003)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_publication_material  'XCIF, SHELXTL, v. 6.14 (Bruker, 2001) '

_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^)+(0.0433P)^2^+0.6517P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         2372
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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
C3 C 0.95397(19) 0.16166(10) 0.4711(3) 0.0181(4) Uani 1 1 d . . .
H3 H 0.9356 0.1231 0.4259 0.022 Uiso 1 1 calc R . .
C6 C 0.9420(2) 0.25067(10) 0.5583(4) 0.0187(4) Uani 1 1 d . . .
H6 H 0.9096 0.2859 0.5845 0.022 Uiso 1 1 calc R . .
C9 C 0.54555(19) 0.46592(9) 0.4519(3) 0.0162(4) Uani 1 1 d . . .
C10 C 0.58889(19) 0.40718(9) 0.4939(3) 0.0154(4) Uani 1 1 d . . .
C17 C 0.8578(2) 0.37709(10) 0.0811(3) 0.0173(4) Uani 1 1 d . . .
H17 H 0.8399 0.4167 0.0859 0.021 Uiso 1 1 calc R . .
C20 C 0.9511(2) 0.29776(9) 0.0764(3) 0.0194(4) Uani 1 1 d . . .
H20 H 1.0114 0.2712 0.0766 0.023 Uiso 1 1 calc R . .
C23 C 0.6015(2) 0.09626(9) 0.0899(4) 0.0193(4) Uani 1 1 d . . .
H23 H 0.6739 0.1172 0.1236 0.023 Uiso 1 1 calc R . .
C26 C 0.46861(19) 0.03003(9) -0.0235(3) 0.0166(4) Uani 1 1 d . . .
H26 H 0.4292 -0.0044 -0.0850 0.020 Uiso 1 1 calc R . .
N1 N 0.75461(17) 0.19136(8) 0.4355(3) 0.0207(4) Uani 1 1 d . . .
H1A H 0.7407 0.1923 0.5572 0.031 Uiso 1 1 d . . .
H1B H 0.7146 0.2208 0.3597 0.031 Uiso 1 1 d . . .
N2 N 0.87748(16) 0.20157(8) 0.4850(3) 0.0165(4) Uani 1 1 d . . .
N4 N 1.05948(17) 0.18567(8) 0.5317(3) 0.0189(4) Uani 1 1 d . . .
H4 H 1.1253 0.1679 0.5362 0.023 Uiso 1 1 calc R . .
N5 N 1.05418(18) 0.24189(8) 0.5870(3) 0.0204(4) Uani 1 1 d . . .
N7 N 0.42548(17) 0.47662(8) 0.3423(3) 0.0172(4) Uani 1 1 d . . .
N8 N 0.62514(17) 0.51173(8) 0.5251(3) 0.0178(4) Uani 1 1 d . . .
N11 N 0.52548(17) 0.36064(8) 0.5039(3) 0.0187(4) Uani 1 1 d . . .
N12 N 0.60360(17) 0.31580(8) 0.5439(3) 0.0197(4) Uani 1 1 d . . .
N13 N 0.70883(18) 0.33327(8) 0.5579(3) 0.0196(4) Uani 1 1 d . . .
N14 N 0.70143(17) 0.39027(8) 0.5269(3) 0.0165(4) Uani 1 1 d . . .
H14 H 0.7605 0.4129 0.5279 0.020 Uiso 1 1 calc R . .
N15 N 1.06543(16) 0.38896(8) 0.1011(3) 0.0183(4) Uani 1 1 d . . .
H15A H 1.1283 0.3758 0.2049 0.027 Uiso 1 1 d . . .
H15B H 1.0734 0.3910 -0.0240 0.027 Uiso 1 1 d . . .
N16 N 0.96443(16) 0.35577(8) 0.0866(3) 0.0161(4) Uani 1 1 d . . .
N18 N 0.78381(17) 0.33487(8) 0.0684(3) 0.0188(4) Uani 1 1 d . . .
N19 N 0.84370(18) 0.28368(8) 0.0661(3) 0.0216(4) Uani 1 1 d . . .
N21 N 0.65512(17) 0.01035(9) -0.0795(3) 0.0196(4) Uani 1 1 d . . .
H21A H 0.6776 0.0300 -0.1721 0.029 Uiso 1 1 d . . .
H21B H 0.7244 0.0094 0.0278 0.029 Uiso 1 1 d . . .
N22 N 0.58040(15) 0.04458(8) -0.0080(3) 0.0159(4) Uani 1 1 d . . .
N24 N 0.50783(17) 0.11314(8) 0.1315(3) 0.0198(4) Uani 1 1 d . . .
N25 N 0.42250(16) 0.06998(8) 0.0582(3) 0.0184(4) Uani 1 1 d . . .
O1 O 0.36058(14) 0.43461(7) 0.2622(3) 0.0234(4) Uani 1 1 d . . .
O2 O 0.38252(15) 0.52585(7) 0.3262(3) 0.0266(4) Uani 1 1 d . . .
O3 O 0.72762(15) 0.49933(7) 0.6453(3) 0.0260(4) Uani 1 1 d . . .
O4 O 0.59739(15) 0.56199(7) 0.4706(3) 0.0267(4) Uani 1 1 d . . .
O5 O 0.77389(15) 0.17301(7) 0.8854(3) 0.0236(4) Uani 1 1 d . . .
H5A H 0.8414 0.1579 0.9063 0.035 Uiso 1 1 d . . .
H5B H 0.7880 0.2059 0.9417 0.035 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
C3 0.0183(11) 0.0155(10) 0.0192(11) 0.0010(8) 0.0051(9) 0.0021(8)
C6 0.0192(10) 0.0159(10) 0.0189(11) -0.0001(8) 0.0039(8) -0.0007(8)
C9 0.0158(10) 0.0122(10) 0.0193(10) -0.0009(8) 0.0045(8) 0.0003(8)
C10 0.0144(10) 0.0165(10) 0.0145(10) -0.0010(8) 0.0039(8) -0.0024(8)
C17 0.0163(10) 0.0172(10) 0.0181(10) -0.0020(8) 0.0057(8) 0.0016(8)
C20 0.0202(10) 0.0148(10) 0.0228(11) -0.0015(9) 0.0070(9) 0.0020(9)
C23 0.0198(11) 0.0185(10) 0.0194(11) -0.0020(8) 0.0064(9) -0.0044(9)
C26 0.0136(9) 0.0171(10) 0.0169(10) 0.0011(8) 0.0023(8) -0.0020(8)
N1 0.0117(8) 0.0200(9) 0.0277(10) -0.0001(8) 0.0036(7) -0.0005(7)
N2 0.0147(9) 0.0137(8) 0.0197(9) -0.0006(7) 0.0043(7) -0.0004(7)
N4 0.0172(9) 0.0163(9) 0.0223(10) -0.0009(7) 0.0055(7) 0.0019(7)
N5 0.0205(9) 0.0156(9) 0.0240(10) -0.0011(8) 0.0062(8) -0.0002(8)
N7 0.0146(8) 0.0178(9) 0.0185(9) 0.0005(7) 0.0049(7) -0.0002(7)
N8 0.0159(8) 0.0154(9) 0.0228(9) -0.0013(7) 0.0073(7) 0.0011(7)
N11 0.0186(9) 0.0144(9) 0.0238(10) 0.0008(7) 0.0082(8) -0.0013(7)
N12 0.0184(9) 0.0160(9) 0.0246(10) 0.0011(7) 0.0073(8) 0.0009(7)
N13 0.0187(9) 0.0138(9) 0.0252(10) -0.0001(7) 0.0063(8) -0.0007(7)
N14 0.0158(9) 0.0123(8) 0.0220(9) -0.0001(7) 0.0072(7) -0.0010(7)
N15 0.0152(9) 0.0210(9) 0.0191(9) 0.0006(7) 0.0067(7) -0.0020(7)
N16 0.0155(9) 0.0161(8) 0.0173(9) -0.0012(7) 0.0062(7) 0.0000(7)
N18 0.0186(9) 0.0158(9) 0.0217(10) -0.0019(7) 0.0065(7) 0.0006(7)
N19 0.0202(9) 0.0167(9) 0.0265(10) -0.0002(7) 0.0067(8) 0.0023(8)
N21 0.0153(9) 0.0241(10) 0.0196(9) 0.0002(8) 0.0065(7) 0.0045(7)
N22 0.0147(8) 0.0177(9) 0.0151(8) -0.0004(7) 0.0049(7) -0.0004(7)
N24 0.0222(10) 0.0180(9) 0.0201(9) -0.0025(7) 0.0083(8) -0.0035(7)
N25 0.0176(9) 0.0165(9) 0.0203(9) 0.0010(7) 0.0055(7) -0.0015(7)
O1 0.0171(8) 0.0200(8) 0.0279(9) -0.0018(6) 0.0012(7) -0.0034(6)
O2 0.0181(8) 0.0175(8) 0.0384(10) -0.0003(7) 0.0026(7) 0.0037(7)
O3 0.0158(8) 0.0185(8) 0.0347(10) -0.0005(7) -0.0025(7) -0.0028(6)
O4 0.0215(9) 0.0115(8) 0.0447(11) 0.0014(7) 0.0083(8) 0.0014(6)
O5 0.0166(8) 0.0198(8) 0.0335(9) -0.0066(7) 0.0077(7) -0.0010(6)

_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
C3 N4 1.310(3) . ?
C3 N2 1.330(3) . ?
C3 H3 0.9500 . ?
C6 N5 1.305(3) . ?
C6 N2 1.372(3) . ?
C6 H6 0.9500 . ?
C9 N7 1.393(3) . ?
C9 N8 1.401(3) . ?
C9 C10 1.454(3) . ?
C10 N11 1.337(3) . ?
C10 N14 1.345(3) . ?
C17 N18 1.305(3) . ?
C17 N16 1.357(3) . ?
C17 H17 0.9500 . ?
C20 N19 1.306(3) . ?
C20 N16 1.357(3) . ?
C20 H20 0.9500 . ?
C23 N24 1.310(3) . ?
C23 N22 1.356(3) . ?
C23 H23 0.9500 . ?
C26 N25 1.302(3) . ?
C26 N22 1.349(3) . ?
C26 H26 0.9500 . ?
N1 N2 1.410(3) . ?
N1 H1A 0.9043 . ?
N1 H1B 0.8918 . ?
N4 N5 1.369(3) . ?
N4 H4 0.8800 . ?
N7 O2 1.244(2) . ?
N7 O1 1.250(3) . ?
N8 O4 1.237(2) . ?
N8 O3 1.250(3) . ?
N11 N12 1.364(3) . ?
N12 N13 1.296(3) . ?
N13 N14 1.340(3) . ?
N14 H14 0.8800 . ?
N15 N16 1.409(2) . ?
N15 H15A 0.8901 . ?
N15 H15B 0.8949 . ?
N18 N19 1.393(3) . ?
N21 N22 1.407(3) . ?
N21 H21A 0.8948 . ?
N21 H21B 0.8962 . ?
N24 N25 1.395(3) . ?
O5 H5A 0.8466 . ?
O5 H5B 0.8469 . ?

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 C3 N2 107.0(2) . . ?
N4 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N5 C6 N2 110.10(19) . . ?
N5 C6 H6 125.0 . . ?
N2 C6 H6 125.0 . . ?
N7 C9 N8 120.19(19) . . ?
N7 C9 C10 120.31(19) . . ?
N8 C9 C10 119.49(19) . . ?
N11 C10 N14 107.96(19) . . ?
N11 C10 C9 126.9(2) . . ?
N14 C10 C9 125.1(2) . . ?
N18 C17 N16 109.71(19) . . ?
N18 C17 H17 125.1 . . ?
N16 C17 H17 125.1 . . ?
N19 C20 N16 110.34(19) . . ?
N19 C20 H20 124.8 . . ?
N16 C20 H20 124.8 . . ?
N24 C23 N22 110.27(19) . . ?
N24 C23 H23 124.9 . . ?
N22 C23 H23 124.9 . . ?
N25 C26 N22 110.18(19) . . ?
N25 C26 H26 124.9 . . ?
N22 C26 H26 124.9 . . ?
N2 N1 H1A 106.6 . . ?
N2 N1 H1B 108.3 . . ?
H1A N1 H1B 106.4 . . ?
C3 N2 C6 107.04(18) . . ?
C3 N2 N1 123.51(19) . . ?
C6 N2 N1 129.43(18) . . ?
C3 N4 N5 111.24(19) . . ?
C3 N4 H4 124.4 . . ?
N5 N4 H4 124.4 . . ?
C6 N5 N4 104.63(18) . . ?
O2 N7 O1 120.38(18) . . ?
O2 N7 C9 121.96(18) . . ?
O1 N7 C9 117.65(18) . . ?
O4 N8 O3 121.03(19) . . ?
O4 N8 C9 122.22(19) . . ?
O3 N8 C9 116.73(18) . . ?
C10 N11 N12 105.49(18) . . ?
N13 N12 N11 110.89(17) . . ?
N12 N13 N14 106.83(18) . . ?
N13 N14 C10 108.82(18) . . ?
N13 N14 H14 125.6 . . ?
C10 N14 H14 125.6 . . ?
N16 N15 H15A 109.5 . . ?
N16 N15 H15B 109.7 . . ?
H15A N15 H15B 116.0 . . ?
C20 N16 C17 105.63(18) . . ?
C20 N16 N15 129.08(18) . . ?
C17 N16 N15 125.29(17) . . ?
C17 N18 N19 107.66(18) . . ?
C20 N19 N18 106.66(18) . . ?
N22 N21 H21A 110.0 . . ?
N22 N21 H21B 104.4 . . ?
H21A N21 H21B 99.8 . . ?
C26 N22 C23 105.68(18) . . ?
C26 N22 N21 124.40(19) . . ?
C23 N22 N21 129.91(18) . . ?
C23 N24 N25 106.36(18) . . ?
C26 N25 N24 107.50(17) . . ?
H5A O5 H5B 105.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O5 0.90 2.19 3.036(3) 156 .
N1 H1B N5 0.89 2.33 3.142(3) 151 4_454
N4 H4 N18 0.88 1.83 2.653(3) 154 4
N4 H4 O4 0.88 2.51 2.964(2) 113 3_545
N14 H14 N25 0.88 1.92 2.741(3) 155 4
N15 H15A O5 0.89 2.09 2.951(3) 164 4_554
N15 H15B N24 0.89 2.21 3.042(3) 154 4_554
N21 H21A N15 0.89 2.51 3.127(3) 126 4_454
N21 H21A O1 0.89 2.52 3.274(3) 142 4_554
N21 H21B O2 0.90 2.28 3.160(3) 166 3_545
N21 H21B O1 0.90 2.54 3.258(3) 138 3_545
O5 H5A N11 0.85 2.11 2.940(3) 166 4
O5 H5A O1 0.85 2.41 2.943(2) 121 4
O5 H5B N19 0.85 2.01 2.851(3) 172 1_556
C3 H3 O2 0.95 2.38 3.331(3) 177 3_545
C3 H3 O4 0.95 2.34 2.886(3) 116 3_545

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.050

data_compound7 ####bt1041
_database_code_depnum_ccdc_archive 'CCDC 646499'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            (C4H7N2)2(C2N6O4)
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 N10 O4'
_chemical_formula_weight         338.31

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   15.7214(10)
_cell_length_b                   12.7935(8)
_cell_length_c                   8.1458(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.096(1)
_cell_angle_gamma                90.00
_cell_volume                     1402.95(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3486
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      29.99

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   'SADABS-2004/1 (Bruker, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker/Siemens SMART APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10924
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1276
_reflns_number_gt                1086
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART v. 5.632 (Bruker, 2006)'
_computing_cell_refinement       'SAINT+ v. 7.23a (Bruker, 2006)'
_computing_data_reduction        'SAINT+ v. 7.23a (Bruker, 2006)'
_computing_structure_solution    'XS, SHELXTL v. 6.14 (Bruker, 2003) '
_computing_structure_refinement  'XL,SHELXTL v. 6.14 (Bruker, 2003)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_publication_material  'XCIF, SHELXTL, v. 6.14 (Bruker, 2001) '

_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^)+(0.0467P)^2^+1.1055P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1276
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.22873(12) 0.17561(13) 1.2970(2) 0.0208(4) Uani 1 1 d . . .
H1A H 0.2380 0.2496 1.3336 0.031 Uiso 1 1 calc R . .
H1B H 0.2933 0.1402 1.3612 0.031 Uiso 1 1 calc R . .
H1C H 0.1853 0.1430 1.3355 0.031 Uiso 1 1 calc R . .
N2 N 0.18333(9) 0.16675(10) 1.08913(18) 0.0161(3) Uani 1 1 d . . .
C3 C 0.13949(11) 0.24365(12) 0.9623(2) 0.0167(4) Uani 1 1 d . . .
H3 H 0.1330 0.3141 0.9912 0.020 Uiso 1 1 calc R . .
N4 N 0.10645(9) 0.20463(10) 0.78866(18) 0.0173(3) Uani 1 1 d . . .
H4 H 0.0756 0.2403 0.6809 0.021 Uiso 1 1 calc R . .
C5 C 0.12789(12) 0.10024(13) 0.8036(2) 0.0203(4) Uani 1 1 d . . .
H5 H 0.1115 0.0534 0.7009 0.024 Uiso 1 1 calc R . .
C6 C 0.17688(12) 0.07649(12) 0.9923(2) 0.0202(4) Uani 1 1 d . . .
H6 H 0.2021 0.0098 1.0475 0.024 Uiso 1 1 calc R . .
C7 C 0.5000 0.19542(17) 0.7500 0.0149(5) Uani 1 2 d S . .
N8 N 0.47613(9) 0.25461(10) 0.59664(18) 0.0166(3) Uani 1 1 d . . .
N9 N 0.48601(10) 0.35438(10) 0.65861(18) 0.0180(3) Uani 1 1 d . . .
C10 C 0.5000 0.08142(17) 0.7500 0.0169(5) Uani 1 2 d S . .
N11 N 0.42795(10) 0.02831(10) 0.76597(18) 0.0177(3) Uani 1 1 d . . .
O12 O 0.35914(8) 0.08371(9) 0.75865(16) 0.0219(3) Uani 1 1 d . . .
O13 O 0.42976(9) -0.06774(8) 0.79003(16) 0.0241(3) Uani 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
C1 0.0217(8) 0.0256(9) 0.0142(8) 0.0013(6) 0.0087(7) 0.0005(7)
N2 0.0149(6) 0.0188(7) 0.0152(7) 0.0007(5) 0.0081(5) 0.0002(5)
C3 0.0166(8) 0.0181(8) 0.0175(8) 0.0004(6) 0.0104(7) -0.0008(6)
N4 0.0179(7) 0.0203(7) 0.0139(7) 0.0030(5) 0.0083(6) 0.0019(5)
C5 0.0235(8) 0.0196(8) 0.0187(8) -0.0027(6) 0.0115(7) 0.0003(7)
C6 0.0237(9) 0.0172(8) 0.0197(8) 0.0008(7) 0.0113(7) 0.0016(7)
C7 0.0125(10) 0.0183(11) 0.0136(11) 0.000 0.0066(9) 0.000
N8 0.0172(7) 0.0156(7) 0.0169(7) 0.0005(5) 0.0088(6) 0.0008(5)
N9 0.0199(7) 0.0159(7) 0.0172(6) -0.0002(5) 0.0087(6) 0.0000(5)
C10 0.0198(11) 0.0167(11) 0.0151(11) 0.000 0.0097(9) 0.000
N11 0.0224(7) 0.0157(7) 0.0129(7) -0.0027(5) 0.0077(6) -0.0028(5)
O12 0.0204(6) 0.0230(6) 0.0245(6) -0.0044(5) 0.0130(5) -0.0018(5)
O13 0.0343(7) 0.0137(6) 0.0260(7) -0.0004(5) 0.0168(6) -0.0050(5)

_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 N2 1.4634(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C3 1.332(2) . ?
N2 C6 1.373(2) . ?
C3 N4 1.327(2) . ?
C3 H3 0.9500 . ?
N4 C5 1.367(2) . ?
N4 H4 0.8800 . ?
C5 C6 1.351(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N8 1.3382(18) 2_656 ?
C7 N8 1.3382(18) . ?
C7 C10 1.458(3) . ?
N8 N9 1.3517(18) . ?
N9 N9 1.317(3) 2_656 ?
C10 N11 1.3835(17) 2_656 ?
C10 N11 1.3835(17) . ?
N11 O13 1.2423(16) . ?
N11 O12 1.2687(17) . ?

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
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N2 C6 108.69(13) . . ?
C3 N2 C1 126.02(14) . . ?
C6 N2 C1 125.27(13) . . ?
N4 C3 N2 108.05(14) . . ?
N4 C3 H3 126.0 . . ?
N2 C3 H3 126.0 . . ?
C3 N4 C5 109.25(13) . . ?
C3 N4 H4 125.4 . . ?
C5 N4 H4 125.4 . . ?
C6 C5 N4 106.89(14) . . ?
C6 C5 H5 126.6 . . ?
N4 C5 H5 126.6 . . ?
C5 C6 N2 107.11(14) . . ?
C5 C6 H6 126.4 . . ?
N2 C6 H6 126.4 . . ?
N8 C7 N8 111.07(19) 2_656 . ?
N8 C7 C10 124.47(10) 2_656 . ?
N8 C7 C10 124.47(10) . . ?
C7 N8 N9 105.25(13) . . ?
N9 N9 N8 109.22(8) 2_656 . ?
N11 C10 N11 121.16(19) 2_656 . ?
N11 C10 C7 119.42(9) 2_656 . ?
N11 C10 C7 119.42(9) . . ?
O13 N11 O12 120.64(13) . . ?
O13 N11 C10 123.19(14) . . ?
O12 N11 C10 116.16(13) . . ?

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
N4 H4 N8 0.88 1.97 2.7566(18) 148 7_556
N4 H4 O13 0.88 2.47 2.9730(17) 117 4_556
C1 H1A O12 0.98 2.50 3.309(2) 139 7_557
C3 H3 O13 0.95 2.48 2.9869(19) 113 4_556
C3 H3 O12 0.95 2.37 3.1615(19) 141 7_557
C6 H6 O12 0.95 2.47 3.2706(19) 142 6_556

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.045