# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

data_CCDC606097

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,2'-Bipyridinium picrate mono-acetonitrile solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C10 H9 N2, C2 H3 N'
_chemical_formula_sum            'C18 H14 N6 O7'
_chemical_formula_weight         426.35

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P_-1
_symmetry_int_tables_number      2
_symmetry_space_group_name_Hall  -P_1

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

_cell_length_a                   3.7068(10)
_cell_length_b                   13.382(3)
_cell_length_c                   18.423(5)
_cell_angle_alpha                98.732(4)
_cell_angle_beta                 93.699(4)
_cell_angle_gamma                95.739(4)
_cell_volume                     895.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2828
_cell_measurement_theta_min      2.516
_cell_measurement_theta_max      28.47

_exptl_crystal_description       rhomb
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8120
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.12
_diffrn_reflns_theta_max         29.01
_reflns_number_total             4238
_reflns_number_gt                3104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.0966P)²+0.8107P] 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         4238
_refine_ls_number_parameters     321
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.2008
_refine_ls_wR_factor_gt          0.1871
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.103
_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
O1 O 0.6618(5) 0.61679(13) 0.21668(10) 0.0272(4) Uani 1 1 d . . .
C1 C 0.8469(6) 0.70097(17) 0.22181(13) 0.0205(5) Uani 1 1 d . . .
C2 C 0.8984(7) 0.75929(18) 0.16150(13) 0.0221(5) Uani 1 1 d . . .
C3 C 1.0797(7) 0.85711(19) 0.17089(15) 0.0258(5) Uani 1 1 d . . .
H3 H 1.095(10) 0.886(3) 0.127(2) 0.046(9) Uiso 1 1 d . . .
C4 C 1.2341(7) 0.90271(18) 0.24012(15) 0.0261(5) Uani 1 1 d . . .
C5 C 1.2015(7) 0.85374(18) 0.30183(15) 0.0249(5) Uani 1 1 d . . .
H5 H 1.303(8) 0.890(2) 0.3514(17) 0.030(8) Uiso 1 1 d . . .
C6 C 1.0196(7) 0.75742(18) 0.29174(13) 0.0221(5) Uani 1 1 d . . .
N2 N 0.7365(6) 0.71723(17) 0.08789(12) 0.0268(5) Uani 1 1 d . . .
O21 O 0.6815(6) 0.62372(15) 0.06945(11) 0.0396(5) Uani 1 1 d . . .
O22 O 0.6570(7) 0.77635(16) 0.04554(11) 0.0470(6) Uani 1 1 d . . .
N4 N 1.4377(6) 1.00304(17) 0.24882(15) 0.0348(6) Uani 1 1 d . . .
O41 O 1.4456(7) 1.04846(17) 0.19506(15) 0.0545(7) Uani 1 1 d . . .
O42 O 1.5988(6) 1.03853(15) 0.30949(14) 0.0461(6) Uani 1 1 d . . .
N6 N 0.9884(6) 0.70745(17) 0.35713(12) 0.0286(5) Uani 1 1 d . . .
O61 O 0.8801(8) 0.75588(19) 0.41220(12) 0.0522(6) Uani 1 1 d . . .
O62 O 1.0751(6) 0.62077(15) 0.35391(12) 0.0401(5) Uani 1 1 d . . .
N011 N 0.2189(6) 0.43439(15) 0.20877(11) 0.0210(4) Uani 1 1 d . . .
H011 H 0.334(9) 0.482(3) 0.2397(19) 0.038(9) Uiso 1 1 d . . .
C012 C 0.1058(7) 0.45124(19) 0.14090(14) 0.0241(5) Uani 1 1 d . . .
H012 H 0.172(8) 0.514(2) 0.1286(16) 0.025(7) Uiso 1 1 d . . .
C013 C -0.0951(7) 0.3737(2) 0.09227(14) 0.0268(5) Uani 1 1 d . . .
H013 H -0.175(9) 0.385(2) 0.0440(18) 0.036(8) Uiso 1 1 d . . .
C014 C -0.1686(7) 0.2790(2) 0.11407(15) 0.0278(6) Uani 1 1 d . . .
H014 H -0.302(9) 0.223(2) 0.0835(17) 0.033(8) Uiso 1 1 d . . .
C015 C -0.0444(7) 0.26328(19) 0.18447(14) 0.0249(5) Uani 1 1 d . . .
H015 H -0.097(9) 0.195(3) 0.1998(18) 0.043(9) Uiso 1 1 d . . .
C016 C 0.1517(6) 0.34372(17) 0.23256(13) 0.0200(5) Uani 1 1 d . . .
N021 N 0.5009(6) 0.42614(15) 0.34263(11) 0.0232(4) Uani 1 1 d . . .
C022 C 0.6282(7) 0.4297(2) 0.41306(15) 0.0271(5) Uani 1 1 d . . .
H022 H 0.775(8) 0.492(2) 0.4362(15) 0.020(7) Uiso 1 1 d . . .
C023 C 0.5603(7) 0.3491(2) 0.45239(15) 0.0294(6) Uani 1 1 d . . .
H023 H 0.666(9) 0.356(2) 0.5015(19) 0.039(9) Uiso 1 1 d . . .
C024 C 0.3570(8) 0.2606(2) 0.41690(15) 0.0299(6) Uani 1 1 d . . .
H024 H 0.307(9) 0.210(3) 0.4407(19) 0.041(9) Uiso 1 1 d . . .
C025 C 0.2216(7) 0.25474(19) 0.34370(15) 0.0256(5) Uani 1 1 d . . .
H025 H 0.077(8) 0.196(2) 0.3182(17) 0.031(8) Uiso 1 1 d . . .
C026 C 0.2971(6) 0.33983(18) 0.30938(13) 0.0207(5) Uani 1 1 d . . .
N11S N 1.175(11) -0.019(2) -0.013(2) 0.252(11) Uani 0.50 1 d PGU . .
C12S C 0.872(12) -0.011(3) -0.003(2) 0.252(11) Uani 0.50 1 d PGU . .
C13S C 0.492(13) 0.000(6) 0.008(4) 0.252(11) Uani 0.50 1 d PGU . .
H1S1 H 0.4722 0.0577 0.0564 0.378 Uiso 0.50 1 d PG . .
H1S2 H 0.3514 -0.0726 0.0174 0.378 Uiso 0.50 1 d PG . .
H1S3 H 0.3557 0.0232 -0.0402 0.378 Uiso 0.50 1 d PG . .
N21S N 0.724(14) 0.016(3) 0.495(3) 0.237(18) Uani 0.50 1 d PGU . .
C22S C 0.417(14) 0.010(4) 0.505(3) 0.237(18) Uani 0.50 1 d PGU . .
C23S C 0.032(14) 0.002(5) 0.517(4) 0.237(18) Uani 0.50 1 d PGU . .
H2S1 H -0.0978 0.0624 0.4952 0.355 Uiso 0.50 1 d PG . .
H2S2 H -0.0027 0.0086 0.5763 0.355 Uiso 0.50 1 d PG . .
H2S3 H -0.1043 -0.0721 0.4895 0.355 Uiso 0.50 1 d PG . .


_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 C1 1.246(3) . ?
C1 C2 1.463(3) . ?
C1 C6 1.463(3) . ?
C2 C3 1.391(3) . ?
C2 N2 1.453(3) . ?
C3 C4 1.388(4) . ?
C3 H3 0.95(4) . ?
C4 C5 1.402(4) . ?
C4 N4 1.454(3) . ?
C5 C6 1.374(3) . ?
C5 H5 1.00(3) . ?
C6 N6 1.469(3) . ?
N2 O22 1.235(3) . ?
N2 O21 1.238(3) . ?
N4 O42 1.236(3) . ?
N4 O41 1.239(4) . ?
N6 O62 1.228(3) . ?
N6 O61 1.231(3) . ?
N011 C012 1.351(3) . ?
N011 C016 1.357(3) . ?
N011 H011 0.84(3) . ?
C012 C013 1.382(4) . ?
C012 H012 0.92(3) . ?
C013 C014 1.394(4) . ?
C013 H013 0.96(3) . ?
C014 C015 1.401(4) . ?
C014 H014 0.94(3) . ?
C015 C016 1.394(3) . ?
C015 H015 1.00(4) . ?
C016 C026 1.492(3) . ?
N021 C022 1.344(3) . ?
N021 C026 1.353(3) . ?
C022 C023 1.400(4) . ?
C022 H022 0.97(3) . ?
C023 C024 1.385(4) . ?
C023 H023 0.95(3) . ?
C024 C025 1.396(4) . ?
C024 H024 0.88(4) . ?
C025 C026 1.397(3) . ?
C025 H025 0.95(3) . ?
N11S C12S 1.1623 . ?
N11S N11S 1.52(5) 2_755 ?
C12S C13S 1.4534 . ?
C13S H1S1 1.0978 . ?
C13S H1S2 1.0978 . ?
C13S H1S3 1.0978 . ?
N21S C22S 1.1623 . ?
C22S C23S 1.4534 . ?
C23S H2S1 1.0978 . ?
C23S H2S2 1.0978 . ?
C23S H2S3 1.0978 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 125.4(2) . . ?
O1 C1 C6 123.1(2) . . ?
C2 C1 C6 111.3(2) . . ?
C3 C2 N2 116.7(2) . . ?
C3 C2 C1 123.6(2) . . ?
N2 C2 C1 119.6(2) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 125(2) . . ?
C2 C3 H3 115(2) . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 N4 119.4(2) . . ?
C5 C4 N4 119.2(2) . . ?
C6 C5 C4 118.1(2) . . ?
C6 C5 H5 122.2(18) . . ?
C4 C5 H5 119.7(18) . . ?
C5 C6 C1 125.7(2) . . ?
C5 C6 N6 117.2(2) . . ?
C1 C6 N6 117.0(2) . . ?
O22 N2 O21 122.0(2) . . ?
O22 N2 C2 118.6(2) . . ?
O21 N2 C2 119.4(2) . . ?
O42 N4 O41 123.0(2) . . ?
O42 N4 C4 118.3(2) . . ?
O41 N4 C4 118.7(3) . . ?
O62 N6 O61 124.0(2) . . ?
O62 N6 C6 118.3(2) . . ?
O61 N6 C6 117.6(2) . . ?
C012 N011 C016 123.6(2) . . ?
C012 N011 H011 121(2) . . ?
C016 N011 H011 116(2) . . ?
N011 C012 C013 119.5(2) . . ?
N011 C012 H012 117.9(18) . . ?
C013 C012 H012 122.5(18) . . ?
C012 C013 C014 118.8(2) . . ?
C012 C013 H013 119.8(19) . . ?
C014 C013 H013 121.3(19) . . ?
C013 C014 C015 120.4(2) . . ?
C013 C014 H014 123.1(19) . . ?
C015 C014 H014 116.5(19) . . ?
C016 C015 C014 119.2(2) . . ?
C016 C015 H015 120.7(19) . . ?
C014 C015 H015 120.1(19) . . ?
N011 C016 C015 118.4(2) . . ?
N011 C016 C026 115.9(2) . . ?
C015 C016 C026 125.7(2) . . ?
C022 N021 C026 117.3(2) . . ?
N021 C022 C023 123.1(2) . . ?
N021 C022 H022 116.4(16) . . ?
C023 C022 H022 120.4(16) . . ?
C024 C023 C022 118.6(3) . . ?
C024 C023 H023 123(2) . . ?
C022 C023 H023 118(2) . . ?
C023 C024 C025 119.5(3) . . ?
C023 C024 H024 120(2) . . ?
C025 C024 H024 120(2) . . ?
C024 C025 C026 117.8(2) . . ?
C024 C025 H025 121.6(18) . . ?
C026 C025 H025 120.6(18) . . ?
N021 C026 C025 123.6(2) . . ?
N021 C026 C016 114.0(2) . . ?
C025 C026 C016 122.4(2) . . ?
N11S C12S C13S 180.0 . . ?
C12S C13S H1S1 110.3 . . ?
C12S C13S H1S2 110.3 . . ?
H1S1 C13S H1S2 108.6 . . ?
C12S C13S H1S3 110.3 . . ?
H1S1 C13S H1S3 108.6 . . ?
H1S2 C13S H1S3 108.6 . . ?
N21S C22S C23S 180.0 . . ?
C22S C23S H2S1 110.3 . . ?
C22S C23S H2S2 110.3 . . ?
H2S1 C23S H2S2 108.6 . . ?
C22S C23S H2S3 110.3 . . ?
H2S1 C23S H2S3 108.6 . . ?
H2S2 C23S H2S3 108.6 . . ?

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 C1 C2 C3 173.9(2) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
O1 C1 C2 N2 -2.4(4) . . . . ?
C6 C1 C2 N2 -178.1(2) . . . . ?
N2 C2 C3 C4 178.7(2) . . . . ?
C1 C2 C3 C4 2.3(4) . . . . ?
C2 C3 C4 C5 -2.2(4) . . . . ?
C2 C3 C4 N4 177.2(2) . . . . ?
C3 C4 C5 C6 1.7(4) . . . . ?
N4 C4 C5 C6 -177.6(2) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C4 C5 C6 N6 -180.0(2) . . . . ?
O1 C1 C6 C5 -174.4(2) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
O1 C1 C6 N6 4.1(3) . . . . ?
C2 C1 C6 N6 179.9(2) . . . . ?
C3 C2 N2 O22 -24.1(3) . . . . ?
C1 C2 N2 O22 152.4(2) . . . . ?
C3 C2 N2 O21 156.0(2) . . . . ?
C1 C2 N2 O21 -27.4(3) . . . . ?
C3 C4 N4 O42 -173.9(2) . . . . ?
C5 C4 N4 O42 5.4(4) . . . . ?
C3 C4 N4 O41 5.2(4) . . . . ?
C5 C4 N4 O41 -175.5(3) . . . . ?
C5 C6 N6 O62 -129.7(3) . . . . ?
C1 C6 N6 O62 51.6(3) . . . . ?
C5 C6 N6 O61 49.5(3) . . . . ?
C1 C6 N6 O61 -129.1(3) . . . . ?
C016 N011 C012 C013 1.1(4) . . . . ?
N011 C012 C013 C014 -1.5(4) . . . . ?
C012 C013 C014 C015 0.8(4) . . . . ?
C013 C014 C015 C016 0.4(4) . . . . ?
C012 N011 C016 C015 0.1(4) . . . . ?
C012 N011 C016 C026 -179.7(2) . . . . ?
C014 C015 C016 N011 -0.8(4) . . . . ?
C014 C015 C016 C026 179.0(2) . . . . ?
C026 N021 C022 C023 0.2(4) . . . . ?
N021 C022 C023 C024 1.0(4) . . . . ?
C022 C023 C024 C025 -0.9(4) . . . . ?
C023 C024 C025 C026 -0.3(4) . . . . ?
C022 N021 C026 C025 -1.6(4) . . . . ?
C022 N021 C026 C016 177.2(2) . . . . ?
C024 C025 C026 N021 1.7(4) . . . . ?
C024 C025 C026 C016 -177.1(2) . . . . ?
N011 C016 C026 N021 -4.8(3) . . . . ?
C015 C016 C026 N021 175.4(2) . . . . ?
N011 C016 C026 C025 174.1(2) . . . . ?
C015 C016 C026 C025 -5.7(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
N011 H011 O1 0.84(3) 2.19(3) 2.781(3) 127(3) .
N011 H011 N021 0.84(3) 2.21(3) 2.638(3) 111(3) .

_diffrn_measured_fraction_theta_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.085

_database_code_depnum_ccdc_archive 'CCDC 606097'
data_CCDC606098

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Morpholinium picrate hemihydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H2 N3 O7), 2(C4 H10 N O), H2 O'
_chemical_formula_sum            'C20 H26 N8 O17'
_chemical_formula_weight         650.49

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   C_2/c
_symmetry_int_tables_number      15
_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                   17.8023(10)
_cell_length_b                   15.2063(9)
_cell_length_c                   20.3551(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.3310(10)
_cell_angle_gamma                90.00
_cell_volume                     5383.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9598
_cell_measurement_theta_min      2.174
_cell_measurement_theta_max      33.2385

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2704
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37364
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         33.41
_reflns_number_total             9892
_reflns_number_gt                6865
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.0912P)²+2.5578P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9892
_refine_ls_number_parameters     511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1657
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
O11 O 0.34977(6) 0.20532(7) 0.35976(5) 0.0238(2) Uani 1 1 d . . .
C11 C 0.31792(7) 0.21848(8) 0.29904(6) 0.0177(2) Uani 1 1 d . . .
C12 C 0.30418(7) 0.30416(8) 0.26728(6) 0.0187(2) Uani 1 1 d . . .
C13 C 0.26744(8) 0.31656(9) 0.20124(7) 0.0202(2) Uani 1 1 d . . .
C14 C 0.24192(8) 0.24456(9) 0.16146(6) 0.0202(2) Uani 1 1 d . . .
C15 C 0.25601(8) 0.15932(9) 0.18530(6) 0.0194(2) Uani 1 1 d . . .
C16 C 0.29308(7) 0.14802(8) 0.25158(6) 0.0178(2) Uani 1 1 d . . .
N12 N 0.33156(7) 0.38376(8) 0.30474(6) 0.0248(2) Uani 1 1 d . . .
O121 O 0.34661(9) 0.38271(9) 0.36595(6) 0.0488(4) Uani 1 1 d . . .
O122 O 0.34019(9) 0.44984(8) 0.27239(7) 0.0448(3) Uani 1 1 d . . .
N14 N 0.19935(8) 0.25827(9) 0.09306(6) 0.0287(3) Uani 1 1 d . . .
O141 O 0.20020(12) 0.33113(10) 0.06830(8) 0.0679(5) Uani 1 1 d . . .
O142 O 0.16188(7) 0.19720(8) 0.06358(6) 0.0352(3) Uani 1 1 d . . .
N16 N 0.31006(7) 0.05706(8) 0.27273(6) 0.0236(2) Uani 1 1 d . . .
O161 O 0.30824(7) 0.03515(7) 0.33044(5) 0.0341(3) Uani 1 1 d . . .
O162 O 0.32516(8) 0.00569(8) 0.23081(6) 0.0379(3) Uani 1 1 d . . .
O21 O 0.47115(7) 0.25015(10) 0.55568(5) 0.0418(3) Uani 1 1 d . . .
C21 C 0.51278(8) 0.25689(11) 0.61391(7) 0.0255(3) Uani 1 1 d . . .
C22 C 0.54322(8) 0.18203(9) 0.65395(7) 0.0226(3) Uani 1 1 d . . .
C23 C 0.58265(7) 0.18611(9) 0.71966(7) 0.0194(2) Uani 1 1 d . . .
C24 C 0.59741(7) 0.26806(8) 0.74918(6) 0.0177(2) Uani 1 1 d . . .
C25 C 0.57157(8) 0.34495(9) 0.71458(7) 0.0223(3) Uani 1 1 d . . .
C26 C 0.53093(8) 0.33845(10) 0.64953(7) 0.0252(3) Uani 1 1 d . . .
N22 N 0.52946(8) 0.09434(10) 0.62490(8) 0.0376(3) Uani 1 1 d . . .
O221 O 0.53131(9) 0.08391(12) 0.56542(8) 0.0601(5) Uani 1 1 d . . .
O222 O 0.51639(9) 0.03492(9) 0.66151(9) 0.0536(4) Uani 1 1 d . . .
N24 N 0.64038(7) 0.27348(9) 0.81767(6) 0.0254(2) Uani 1 1 d . . .
O241 O 0.65957(9) 0.20569(10) 0.84873(6) 0.0449(3) Uani 1 1 d . . .
O242 O 0.65598(7) 0.34673(9) 0.84215(6) 0.0425(3) Uani 1 1 d . . .
N26 N 0.50221(10) 0.42075(11) 0.61612(8) 0.0442(4) Uani 1 1 d . . .
O261 O 0.49654(15) 0.42639(14) 0.55548(9) 0.0920(7) Uani 1 1 d . . .
O262 O 0.48437(9) 0.47947(9) 0.65072(9) 0.0535(4) Uani 1 1 d . . .
N011 N 0.50083(8) 0.23518(9) 0.43125(6) 0.0261(3) Uani 1 1 d . . .
C012 C 0.53544(10) 0.31786(11) 0.41139(8) 0.0303(3) Uani 1 1 d . . .
C013 C 0.53535(10) 0.31305(10) 0.33698(8) 0.0280(3) Uani 1 1 d . . .
O014 O 0.57585(6) 0.23767(7) 0.32169(6) 0.0278(2) Uani 1 1 d . . .
C015 C 0.54176(9) 0.15905(10) 0.33964(7) 0.0262(3) Uani 1 1 d . . .
C016 C 0.54270(9) 0.15635(10) 0.41425(8) 0.0280(3) Uani 1 1 d . . .
N021 N 0.22846(8) 0.40360(8) 0.54178(6) 0.0244(2) Uani 1 1 d . . .
C022 C 0.27984(13) 0.48242(11) 0.55531(9) 0.0396(4) Uani 1 1 d . . .
C023 C 0.29322(12) 0.51917(13) 0.49018(9) 0.0411(4) Uani 1 1 d . . .
O024 O 0.22230(7) 0.54228(8) 0.44586(6) 0.0355(3) Uani 1 1 d . . .
C025 C 0.17680(11) 0.46617(11) 0.43064(8) 0.0352(4) Uani 1 1 d . . .
C026 C 0.15633(9) 0.42623(13) 0.49262(9) 0.0341(3) Uani 1 1 d . . .
O01W O 0.32394(7) 0.29054(8) 0.48699(6) 0.0335(3) Uani 1 1 d . . .
H13 H 0.2598(11) 0.3715(14) 0.1854(9) 0.030(5) Uiso 1 1 d . . .
H15 H 0.2405(11) 0.1119(13) 0.1563(10) 0.031(5) Uiso 1 1 d . . .
H23 H 0.5991(11) 0.1353(13) 0.7411(10) 0.034(5) Uiso 1 1 d . . .
H25 H 0.5800(11) 0.4011(13) 0.7343(10) 0.034(5) Uiso 1 1 d . . .
H01A H 0.4542(13) 0.2332(13) 0.4105(11) 0.036(5) Uiso 1 1 d . . .
H01B H 0.5001(13) 0.2347(14) 0.4731(12) 0.039(5) Uiso 1 1 d . . .
H01C H 0.5879(13) 0.3212(14) 0.4392(11) 0.037(5) Uiso 1 1 d . . .
H01D H 0.5073(12) 0.3652(15) 0.4216(11) 0.041(6) Uiso 1 1 d . . .
H01E H 0.4830(11) 0.3111(12) 0.3102(10) 0.027(4) Uiso 1 1 d . . .
H01F H 0.5636(11) 0.3628(14) 0.3242(10) 0.036(5) Uiso 1 1 d . . .
H01G H 0.5705(12) 0.1159(15) 0.3262(10) 0.040(5) Uiso 1 1 d . . .
H01H H 0.4888(12) 0.1560(13) 0.3124(10) 0.032(5) Uiso 1 1 d . . .
H01I H 0.5159(12) 0.1071(15) 0.4268(11) 0.040(5) Uiso 1 1 d . . .
H01J H 0.5936(12) 0.1568(13) 0.4450(10) 0.033(5) Uiso 1 1 d . . .
H02A H 0.2497(11) 0.3618(14) 0.5261(10) 0.027(5) Uiso 1 1 d . . .
H02B H 0.2181(12) 0.3824(15) 0.5802(12) 0.045(6) Uiso 1 1 d . . .
H02C H 0.2510(15) 0.5248(17) 0.5774(12) 0.056(7) Uiso 1 1 d . . .
H02D H 0.3277(16) 0.4670(18) 0.5853(14) 0.067(8) Uiso 1 1 d . . .
H02E H 0.3217(16) 0.5783(19) 0.4989(13) 0.066(7) Uiso 1 1 d . . .
H02F H 0.3166(11) 0.4721(14) 0.4682(10) 0.032(5) Uiso 1 1 d . . .
H02G H 0.2035(14) 0.4208(17) 0.4078(12) 0.056(7) Uiso 1 1 d . . .
H02H H 0.1283(13) 0.4839(15) 0.4005(12) 0.047(6) Uiso 1 1 d . . .
H02I H 0.1343(14) 0.4679(16) 0.5154(11) 0.048(6) Uiso 1 1 d . . .
H02J H 0.1301(13) 0.3746(16) 0.4817(11) 0.046(6) Uiso 1 1 d . . .
H0WA H 0.3283(16) 0.2941(17) 0.4410(15) 0.065(8) Uiso 1 1 d . . .
H0WB H 0.3728(17) 0.2843(17) 0.5162(14) 0.065(8) Uiso 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
O11 C11 1.2608(15) . ?
C11 C16 1.4472(18) . ?
C11 C12 1.4519(18) . ?
C12 C13 1.3766(18) . ?
C12 N12 1.4578(17) . ?
C13 C14 1.3796(19) . ?
C13 H13 0.90(2) . ?
C14 C15 1.3881(19) . ?
C14 N14 1.4511(17) . ?
C15 C16 1.3802(17) . ?
C15 H15 0.94(2) . ?
C16 N16 1.4608(17) . ?
N12 O121 1.2173(17) . ?
N12 O122 1.2288(17) . ?
N14 O141 1.2186(19) . ?
N14 O142 1.2233(18) . ?
N16 O162 1.2283(16) . ?
N16 O161 1.2281(15) . ?
O21 C21 1.2606(17) . ?
C21 C22 1.437(2) . ?
C21 C26 1.438(2) . ?
C22 C23 1.3729(18) . ?
C22 N22 1.4580(19) . ?
C23 C24 1.3841(18) . ?
C23 H23 0.90(2) . ?
C24 C25 1.3915(18) . ?
C24 N24 1.4423(17) . ?
C25 C26 1.370(2) . ?
C25 H25 0.94(2) . ?
C26 N26 1.4635(19) . ?
N22 O222 1.225(2) . ?
N22 O221 1.229(2) . ?
N24 O241 1.2194(18) . ?
N24 O242 1.2275(17) . ?
N26 O262 1.220(2) . ?
N26 O261 1.220(2) . ?
N011 C016 1.491(2) . ?
N011 C012 1.493(2) . ?
N011 H01A 0.85(2) . ?
N011 H01B 0.85(2) . ?
C012 C013 1.516(2) . ?
C012 H01C 0.98(2) . ?
C012 H01D 0.93(2) . ?
C013 O014 1.4234(18) . ?
C013 H01E 0.974(19) . ?
C013 H01F 0.97(2) . ?
O014 C015 1.4233(18) . ?
C015 C016 1.516(2) . ?
C015 H01G 0.91(2) . ?
C015 H01H 0.99(2) . ?
C016 H01I 0.95(2) . ?
C016 H01J 0.99(2) . ?
N021 C026 1.490(2) . ?
N021 C022 1.497(2) . ?
N021 H02A 0.84(2) . ?
N021 H02B 0.90(2) . ?
C022 C023 1.504(3) . ?
C022 H02C 0.99(3) . ?
C022 H02D 0.96(3) . ?
C023 O024 1.430(2) . ?
C023 H02E 1.03(3) . ?
C023 H02F 0.98(2) . ?
O024 C025 1.409(2) . ?
C025 C026 1.513(2) . ?
C025 H02G 1.01(3) . ?
C025 H02H 0.98(2) . ?
C026 H02I 0.92(2) . ?
C026 H02J 0.92(2) . ?
O01W H0WA 0.96(3) . ?
O01W H0WB 0.95(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
O11 C11 C16 123.11(12) . . ?
O11 C11 C12 125.21(12) . . ?
C16 C11 C12 111.64(11) . . ?
C13 C12 C11 123.88(12) . . ?
C13 C12 N12 115.67(11) . . ?
C11 C12 N12 120.43(11) . . ?
C12 C13 C14 119.52(12) . . ?
C12 C13 H13 118.9(12) . . ?
C14 C13 H13 121.6(12) . . ?
C13 C14 C15 121.57(12) . . ?
C13 C14 N14 119.22(12) . . ?
C15 C14 N14 119.21(12) . . ?
C16 C15 C14 118.10(12) . . ?
C16 C15 H15 122.5(12) . . ?
C14 C15 H15 119.4(12) . . ?
C15 C16 C11 125.06(12) . . ?
C15 C16 N16 115.57(11) . . ?
C11 C16 N16 119.32(11) . . ?
O121 N12 O122 122.26(13) . . ?
O121 N12 C12 120.02(12) . . ?
O122 N12 C12 117.70(12) . . ?
O141 N14 O142 122.75(14) . . ?
O141 N14 C14 118.51(13) . . ?
O142 N14 C14 118.68(12) . . ?
O162 N16 O161 123.12(12) . . ?
O162 N16 C16 117.36(11) . . ?
O161 N16 C16 119.52(11) . . ?
O21 C21 C22 122.93(15) . . ?
O21 C21 C26 124.59(14) . . ?
C22 C21 C26 112.35(12) . . ?
C23 C22 C21 124.70(13) . . ?
C23 C22 N22 116.29(13) . . ?
C21 C22 N22 118.96(12) . . ?
C22 C23 C24 118.28(12) . . ?
C22 C23 H23 118.5(13) . . ?
C24 C23 H23 123.2(13) . . ?
C23 C24 C25 121.69(12) . . ?
C23 C24 N24 118.91(12) . . ?
C25 C24 N24 119.40(12) . . ?
C26 C25 C24 118.54(13) . . ?
C26 C25 H25 118.7(12) . . ?
C24 C25 H25 122.7(12) . . ?
C25 C26 C21 124.39(12) . . ?
C25 C26 N26 116.58(14) . . ?
C21 C26 N26 118.98(14) . . ?
O222 N22 O221 123.57(16) . . ?
O222 N22 C22 117.73(14) . . ?
O221 N22 C22 118.70(17) . . ?
O241 N24 O242 122.87(13) . . ?
O241 N24 C24 119.00(12) . . ?
O242 N24 C24 118.13(13) . . ?
O262 N26 O261 123.86(17) . . ?
O262 N26 C26 117.74(15) . . ?
O261 N26 C26 118.40(18) . . ?
C016 N011 C012 111.00(12) . . ?
C016 N011 H01A 109.9(14) . . ?
C012 N011 H01A 108.1(14) . . ?
C016 N011 H01B 109.8(14) . . ?
C012 N011 H01B 111.8(14) . . ?
H01A N011 H01B 106(2) . . ?
N011 C012 C013 108.51(12) . . ?
N011 C012 H01C 106.4(12) . . ?
C013 C012 H01C 112.0(12) . . ?
N011 C012 H01D 108.6(14) . . ?
C013 C012 H01D 112.1(13) . . ?
H01C C012 H01D 108.9(18) . . ?
O014 C013 C012 111.39(12) . . ?
O014 C013 H01E 108.7(11) . . ?
C012 C013 H01E 110.9(11) . . ?
O014 C013 H01F 104.6(12) . . ?
C012 C013 H01F 109.8(12) . . ?
H01E C013 H01F 111.2(16) . . ?
C015 O014 C013 110.90(11) . . ?
O014 C015 C016 111.46(12) . . ?
O014 C015 H01G 103.3(13) . . ?
C016 C015 H01G 113.3(13) . . ?
O014 C015 H01H 107.7(11) . . ?
C016 C015 H01H 111.5(11) . . ?
H01G C015 H01H 109.2(17) . . ?
N011 C016 C015 108.17(12) . . ?
N011 C016 H01I 105.5(13) . . ?
C015 C016 H01I 113.0(13) . . ?
N011 C016 H01J 106.5(12) . . ?
C015 C016 H01J 116.6(11) . . ?
H01I C016 H01J 106.3(17) . . ?
C026 N021 C022 110.10(13) . . ?
C026 N021 H02A 108.3(13) . . ?
C022 N021 H02A 111.7(13) . . ?
C026 N021 H02B 111.1(14) . . ?
C022 N021 H02B 110.9(14) . . ?
H02A N021 H02B 104.7(19) . . ?
N021 C022 C023 109.93(14) . . ?
N021 C022 H02C 104.5(15) . . ?
C023 C022 H02C 110.7(14) . . ?
N021 C022 H02D 110.1(17) . . ?
C023 C022 H02D 111.3(16) . . ?
H02C C022 H02D 110(2) . . ?
O024 C023 C022 111.27(17) . . ?
O024 C023 H02E 103.3(15) . . ?
C022 C023 H02E 109.7(15) . . ?
O024 C023 H02F 107.2(12) . . ?
C022 C023 H02F 107.0(12) . . ?
H02E C023 H02F 118.3(19) . . ?
C025 O024 C023 109.00(12) . . ?
O024 C025 C026 112.09(14) . . ?
O024 C025 H02G 111.0(14) . . ?
C026 C025 H02G 109.4(14) . . ?
O024 C025 H02H 107.4(13) . . ?
C026 C025 H02H 107.1(13) . . ?
H02G C025 H02H 109.7(19) . . ?
N021 C026 C025 109.04(14) . . ?
N021 C026 H02I 102.6(15) . . ?
C025 C026 H02I 110.4(14) . . ?
N021 C026 H02J 106.6(14) . . ?
C025 C026 H02J 110.0(14) . . ?
H02I C026 H02J 118(2) . . ?
H0WA O01W H0WB 111(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
O11 C11 C12 C13 -178.25(13) . . . . ?
C16 C11 C12 C13 3.98(18) . . . . ?
O11 C11 C12 N12 3.5(2) . . . . ?
C16 C11 C12 N12 -174.24(11) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
N12 C12 C13 C14 177.88(12) . . . . ?
C12 C13 C14 C15 -3.5(2) . . . . ?
C12 C13 C14 N14 176.47(12) . . . . ?
C13 C14 C15 C16 3.3(2) . . . . ?
N14 C14 C15 C16 -176.68(12) . . . . ?
C14 C15 C16 C11 0.8(2) . . . . ?
C14 C15 C16 N16 -176.77(11) . . . . ?
O11 C11 C16 C15 177.97(12) . . . . ?
C12 C11 C16 C15 -4.20(18) . . . . ?
O11 C11 C16 N16 -4.52(19) . . . . ?
C12 C11 C16 N16 173.30(11) . . . . ?
C13 C12 N12 O121 161.36(14) . . . . ?
C11 C12 N12 O121 -20.3(2) . . . . ?
C13 C12 N12 O122 -20.22(19) . . . . ?
C11 C12 N12 O122 158.14(13) . . . . ?
C13 C14 N14 O141 14.2(2) . . . . ?
C15 C14 N14 O141 -165.76(17) . . . . ?
C13 C14 N14 O142 -163.13(13) . . . . ?
C15 C14 N14 O142 16.9(2) . . . . ?
C15 C16 N16 O162 33.47(18) . . . . ?
C11 C16 N16 O162 -144.27(13) . . . . ?
C15 C16 N16 O161 -146.07(13) . . . . ?
C11 C16 N16 O161 36.20(18) . . . . ?
O21 C21 C22 C23 -173.64(14) . . . . ?
C26 C21 C22 C23 2.5(2) . . . . ?
O21 C21 C22 N22 3.7(2) . . . . ?
C26 C21 C22 N22 179.82(13) . . . . ?
C21 C22 C23 C24 -2.9(2) . . . . ?
N22 C22 C23 C24 179.62(12) . . . . ?
C22 C23 C24 C25 1.8(2) . . . . ?
C22 C23 C24 N24 -178.52(12) . . . . ?
C23 C24 C25 C26 -0.4(2) . . . . ?
N24 C24 C25 C26 179.91(12) . . . . ?
C24 C25 C26 C21 0.0(2) . . . . ?
C24 C25 C26 N26 177.54(13) . . . . ?
O21 C21 C26 C25 175.08(14) . . . . ?
C22 C21 C26 C25 -0.9(2) . . . . ?
O21 C21 C26 N26 -2.4(2) . . . . ?
C22 C21 C26 N26 -178.41(13) . . . . ?
C23 C22 N22 O222 36.0(2) . . . . ?
C21 C22 N22 O222 -141.55(15) . . . . ?
C23 C22 N22 O221 -144.18(15) . . . . ?
C21 C22 N22 O221 38.2(2) . . . . ?
C23 C24 N24 O241 -3.3(2) . . . . ?
C25 C24 N24 O241 176.44(13) . . . . ?
C23 C24 N24 O242 176.80(13) . . . . ?
C25 C24 N24 O242 -3.50(19) . . . . ?
C25 C26 N26 O262 -32.2(2) . . . . ?
C21 C26 N26 O262 145.51(16) . . . . ?
C25 C26 N26 O261 148.8(2) . . . . ?
C21 C26 N26 O261 -33.6(3) . . . . ?
C016 N011 C012 C013 56.34(16) . . . . ?
N011 C012 C013 O014 -57.30(17) . . . . ?
C012 C013 O014 C015 59.88(17) . . . . ?
C013 O014 C015 C016 -60.37(16) . . . . ?
C012 N011 C016 C015 -56.55(16) . . . . ?
O014 C015 C016 N011 58.03(16) . . . . ?
C026 N021 C022 C023 -54.0(2) . . . . ?
N021 C022 C023 O024 57.9(2) . . . . ?
C022 C023 O024 C025 -61.4(2) . . . . ?
C023 O024 C025 C026 62.1(2) . . . . ?
C022 N021 C026 C025 53.6(2) . . . . ?
O024 C025 C026 N021 -58.8(2) . . . . ?

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
#N021 H02A O01W  0.84(2) 2.65(2) 3.1137(18) 116.6(15) 7_556 
N011 H01A O11 0.85(2) 1.97(2) 2.8078(16) 169(2) .
N011 H01B O21 0.85(2) 1.88(2) 2.7050(16) 163(2) .
N021 H02A O01W 0.84(2) 2.00(2) 2.8104(18) 162.5(18) .
N021 H02B O11 0.90(2) 2.32(2) 3.1452(16) 152.9(19) 7_556
N021 H02B O161 0.90(2) 2.34(2) 2.9640(18) 126.6(18) 7_556
O01W H0WA O121 0.96(3) 2.11(3) 2.9363(18) 143(2) .
O01W H0WA O11 0.96(3) 2.23(3) 3.0176(16) 139(2) .
O01W H0WB O21 0.95(3) 1.84(3) 2.7632(17) 164(2) .

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.072


_database_code_depnum_ccdc_archive 'CCDC 606098'
data_CCDC606099

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,10-Phenanthrolinium picrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C12 H9 N2'
_chemical_formula_sum            'C18 H11 N5 O7'
_chemical_formula_weight         409.32

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   P_21/c
_symmetry_int_tables_number      14
_symmetry_space_group_name_Hall  -P_2ybc

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                   13.509(5)
_cell_length_b                   7.028(3)
_cell_length_c                   18.804(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.116(6)
_cell_angle_gamma                90.00
_cell_volume                     1767.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4060
_cell_measurement_theta_min      2.4835
_cell_measurement_theta_max      27.5685

_exptl_crystal_description       slab
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14321
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         28.60
_reflns_number_total             4149
_reflns_number_gt                2679
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.0767P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4149
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
N011 N 0.65104(12) 0.5053(2) 0.35251(9) 0.0261(4) Uani 1 1 d . . .
H011 H 0.6191(17) 0.487(3) 0.3061(13) 0.044(7) Uiso 1 1 d . . .
C012 C 0.59763(15) 0.4856(3) 0.40767(11) 0.0306(5) Uani 1 1 d . . .
H012 H 0.5250(15) 0.449(3) 0.3951(10) 0.026(5) Uiso 1 1 d . . .
C013 C 0.64411(16) 0.5168(3) 0.47955(12) 0.0347(5) Uani 1 1 d . . .
H013 H 0.6085(15) 0.499(3) 0.5231(11) 0.035(6) Uiso 1 1 d . . .
C014 C 0.74516(16) 0.5715(3) 0.49186(12) 0.0340(5) Uani 1 1 d . . .
H014 H 0.7779(15) 0.590(3) 0.5400(11) 0.035(6) Uiso 1 1 d . . .
C015 C 0.80146(14) 0.5924(3) 0.43297(11) 0.0291(5) Uani 1 1 d . . .
C016 C 0.75144(13) 0.5550(3) 0.36212(10) 0.0253(4) Uani 1 1 d . . .
C017 C 0.90684(15) 0.6494(3) 0.44143(12) 0.0349(5) Uani 1 1 d . . .
H017 H 0.9395(15) 0.677(3) 0.4906(11) 0.039(6) Uiso 1 1 d . . .
N021 N 0.74928(12) 0.5237(2) 0.23316(9) 0.0307(4) Uani 1 1 d . . .
C022 C 0.79816(16) 0.5341(3) 0.17556(12) 0.0343(5) Uani 1 1 d . . .
H022 H 0.7599(18) 0.502(3) 0.1311(13) 0.049(7) Uiso 1 1 d . . .
C023 C 0.90116(16) 0.5888(3) 0.17954(13) 0.0374(5) Uani 1 1 d . . .
H023 H 0.9296(17) 0.597(3) 0.1336(13) 0.050(7) Uiso 1 1 d . . .
C024 C 0.95552(16) 0.6313(3) 0.24613(13) 0.0375(5) Uani 1 1 d . . .
H024 H 1.0270(16) 0.670(3) 0.2522(11) 0.043(6) Uiso 1 1 d . . .
C025 C 0.90754(14) 0.6210(3) 0.30981(11) 0.0306(5) Uani 1 1 d . . .
C026 C 0.80389(14) 0.5661(3) 0.29914(11) 0.0272(4) Uani 1 1 d . . .
C027 C 0.95768(15) 0.6626(3) 0.38280(12) 0.0350(5) Uani 1 1 d . . .
H027 H 1.0290(15) 0.698(3) 0.3880(10) 0.033(5) Uiso 1 1 d . . .
O1 O 0.49309(10) 0.4123(2) 0.25354(8) 0.0347(4) Uani 1 1 d . . .
C1 C 0.41756(14) 0.4631(3) 0.20951(10) 0.0276(4) Uani 1 1 d . . .
C2 C 0.42156(13) 0.4894(3) 0.13144(11) 0.0258(4) Uani 1 1 d . . .
C3 C 0.34121(14) 0.5394(3) 0.07962(11) 0.0271(4) Uani 1 1 d . . .
H3 H 0.3484(14) 0.553(3) 0.0262(11) 0.031(5) Uiso 1 1 d . . .
C4 C 0.24659(13) 0.5709(3) 0.10300(10) 0.0249(4) Uani 1 1 d . . .
C5 C 0.23459(14) 0.5573(3) 0.17597(10) 0.0256(4) Uani 1 1 d . . .
H5 H 0.1666(15) 0.582(3) 0.1926(10) 0.027(5) Uiso 1 1 d . . .
C6 C 0.31626(14) 0.5060(3) 0.22782(10) 0.0260(4) Uani 1 1 d . . .
N2 N 0.51970(12) 0.4603(2) 0.10529(9) 0.0308(4) Uani 1 1 d . . .
O21 O 0.56600(10) 0.3087(2) 0.12108(9) 0.0439(4) Uani 1 1 d . . .
O22 O 0.54968(10) 0.5893(2) 0.06696(8) 0.0386(4) Uani 1 1 d . . .
N4 N 0.15938(12) 0.6185(2) 0.04992(9) 0.0293(4) Uani 1 1 d . . .
O41 O 0.16808(11) 0.6122(2) -0.01556(8) 0.0442(4) Uani 1 1 d . . .
O42 O 0.07908(10) 0.6659(2) 0.07282(8) 0.0377(4) Uani 1 1 d . . .
N6 N 0.29470(12) 0.4887(2) 0.30259(9) 0.0303(4) Uani 1 1 d . . .
O61 O 0.35694(10) 0.4105(2) 0.34916(7) 0.0384(4) Uani 1 1 d . . .
O62 O 0.21209(11) 0.5522(2) 0.31698(8) 0.0436(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
N011 C012 1.352(3) . ?
N011 C016 1.387(2) . ?
N011 H011 0.93(2) . ?
C012 C013 1.425(3) . ?
C012 H012 1.010(19) . ?
C013 C014 1.405(3) . ?
C013 H013 1.02(2) . ?
C014 C015 1.437(3) . ?
C014 H014 0.96(2) . ?
C015 C016 1.430(3) . ?
C015 C017 1.466(3) . ?
C016 C026 1.465(3) . ?
C017 C027 1.382(3) . ?
C017 H017 0.99(2) . ?
N021 C022 1.348(3) . ?
N021 C026 1.384(3) . ?
C022 C023 1.435(3) . ?
C022 H022 0.95(2) . ?
C023 C024 1.392(3) . ?
C023 H023 1.00(2) . ?
C024 C025 1.442(3) . ?
C024 H024 0.99(2) . ?
C025 C026 1.439(3) . ?
C025 C027 1.472(3) . ?
C027 H027 0.99(2) . ?
O1 C1 1.271(2) . ?
C1 C2 1.488(3) . ?
C1 C6 1.488(3) . ?
C2 C3 1.397(3) . ?
C2 N2 1.492(2) . ?
C3 C4 1.426(3) . ?
C3 H3 1.03(2) . ?
C4 C5 1.408(3) . ?
C4 N4 1.471(2) . ?
C5 C6 1.412(3) . ?
C5 H5 1.025(19) . ?
C6 N6 1.481(3) . ?
N2 O21 1.250(2) . ?
N2 O22 1.260(2) . ?
N4 O41 1.254(2) . ?
N4 O42 1.267(2) . ?
N6 O61 1.252(2) . ?
N6 O62 1.266(2) . ?

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
C012 N011 C016 122.95(17) . . ?
C012 N011 H011 118.8(14) . . ?
C016 N011 H011 118.3(14) . . ?
N011 C012 C013 120.05(19) . . ?
N011 C012 H012 116.9(11) . . ?
C013 C012 H012 123.0(11) . . ?
C014 C013 C012 119.1(2) . . ?
C014 C013 H013 117.5(12) . . ?
C012 C013 H013 123.4(12) . . ?
C013 C014 C015 120.6(2) . . ?
C013 C014 H014 120.1(12) . . ?
C015 C014 H014 119.3(12) . . ?
C016 C015 C014 117.85(18) . . ?
C016 C015 C017 118.37(18) . . ?
C014 C015 C017 123.78(19) . . ?
N011 C016 C015 119.47(17) . . ?
N011 C016 C026 118.92(17) . . ?
C015 C016 C026 121.60(17) . . ?
C027 C017 C015 121.1(2) . . ?
C027 C017 H017 121.9(12) . . ?
C015 C017 H017 117.0(12) . . ?
C022 N021 C026 116.71(17) . . ?
N021 C022 C023 123.6(2) . . ?
N021 C022 H022 115.4(15) . . ?
C023 C022 H022 121.0(15) . . ?
C024 C023 C022 119.3(2) . . ?
C024 C023 H023 123.3(13) . . ?
C022 C023 H023 117.4(13) . . ?
C023 C024 C025 119.6(2) . . ?
C023 C024 H024 122.9(12) . . ?
C025 C024 H024 117.5(12) . . ?
C026 C025 C024 116.14(19) . . ?
C026 C025 C027 119.60(18) . . ?
C024 C025 C027 124.26(19) . . ?
N021 C026 C025 124.60(18) . . ?
N021 C026 C016 117.12(17) . . ?
C025 C026 C016 118.28(18) . . ?
C017 C027 C025 121.04(19) . . ?
C017 C027 H027 121.7(11) . . ?
C025 C027 H027 117.2(11) . . ?
O1 C1 C2 122.67(17) . . ?
O1 C1 C6 125.88(18) . . ?
C2 C1 C6 111.45(16) . . ?
C3 C2 C1 125.89(17) . . ?
C3 C2 N2 116.34(17) . . ?
C1 C2 N2 117.77(16) . . ?
C2 C3 C4 117.77(18) . . ?
C2 C3 H3 122.3(11) . . ?
C4 C3 H3 120.0(11) . . ?
C5 C4 C3 121.43(17) . . ?
C5 C4 N4 119.04(16) . . ?
C3 C4 N4 119.53(17) . . ?
C4 C5 C6 120.27(17) . . ?
C4 C5 H5 121.1(11) . . ?
C6 C5 H5 118.6(11) . . ?
C5 C6 N6 115.94(16) . . ?
C5 C6 C1 123.12(17) . . ?
N6 C6 C1 120.89(16) . . ?
O21 N2 O22 123.98(17) . . ?
O21 N2 C2 118.48(16) . . ?
O22 N2 C2 117.51(16) . . ?
O41 N4 O42 123.12(16) . . ?
O41 N4 C4 118.75(16) . . ?
O42 N4 C4 118.12(16) . . ?
O61 N6 O62 122.03(16) . . ?
O61 N6 C6 119.84(16) . . ?
O62 N6 C6 118.12(16) . . ?

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
C016 N011 C012 C013 0.2(3) . . . . ?
N011 C012 C013 C014 1.2(3) . . . . ?
C012 C013 C014 C015 -1.1(3) . . . . ?
C013 C014 C015 C016 -0.3(3) . . . . ?
C013 C014 C015 C017 179.78(19) . . . . ?
C012 N011 C016 C015 -1.7(3) . . . . ?
C012 N011 C016 C026 177.79(17) . . . . ?
C014 C015 C016 N011 1.7(3) . . . . ?
C017 C015 C016 N011 -178.41(17) . . . . ?
C014 C015 C016 C026 -177.80(17) . . . . ?
C017 C015 C016 C026 2.1(3) . . . . ?
C016 C015 C017 C027 -1.5(3) . . . . ?
C014 C015 C017 C027 178.39(19) . . . . ?
C026 N021 C022 C023 -1.0(3) . . . . ?
N021 C022 C023 C024 1.0(3) . . . . ?
C022 C023 C024 C025 -0.4(3) . . . . ?
C023 C024 C025 C026 -0.1(3) . . . . ?
C023 C024 C025 C027 179.94(19) . . . . ?
C022 N021 C026 C025 0.5(3) . . . . ?
C022 N021 C026 C016 -179.91(17) . . . . ?
C024 C025 C026 N021 0.1(3) . . . . ?
C027 C025 C026 N021 -179.96(18) . . . . ?
C024 C025 C026 C016 -179.54(17) . . . . ?
C027 C025 C026 C016 0.4(3) . . . . ?
N011 C016 C026 N021 -0.7(3) . . . . ?
C015 C016 C026 N021 178.77(16) . . . . ?
N011 C016 C026 C025 178.94(17) . . . . ?
C015 C016 C026 C025 -1.6(3) . . . . ?
C015 C017 C027 C025 0.4(3) . . . . ?
C026 C025 C027 C017 0.1(3) . . . . ?
C024 C025 C027 C017 -179.90(19) . . . . ?
O1 C1 C2 C3 177.99(18) . . . . ?
C6 C1 C2 C3 -2.7(3) . . . . ?
O1 C1 C2 N2 -2.0(3) . . . . ?
C6 C1 C2 N2 177.27(15) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
N2 C2 C3 C4 -179.17(16) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C4 N4 -178.29(16) . . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
N4 C4 C5 C6 178.04(16) . . . . ?
C4 C5 C6 N6 -177.75(16) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
O1 C1 C6 C5 -178.33(18) . . . . ?
C2 C1 C6 C5 2.4(2) . . . . ?
O1 C1 C6 N6 -1.0(3) . . . . ?
C2 C1 C6 N6 179.73(15) . . . . ?
C3 C2 N2 O21 -127.72(19) . . . . ?
C1 C2 N2 O21 52.3(2) . . . . ?
C3 C2 N2 O22 50.7(2) . . . . ?
C1 C2 N2 O22 -129.34(18) . . . . ?
C5 C4 N4 O41 -173.10(17) . . . . ?
C3 C4 N4 O41 6.9(3) . . . . ?
C5 C4 N4 O42 7.6(2) . . . . ?
C3 C4 N4 O42 -172.45(17) . . . . ?
C5 C6 N6 O61 166.74(17) . . . . ?
C1 C6 N6 O61 -10.8(3) . . . . ?
C5 C6 N6 O62 -12.3(2) . . . . ?
C1 C6 N6 O62 170.19(17) . . . . ?

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
N011 H011 O1 0.93(2) 1.92(2) 2.706(2) 141.7(19) .

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.059

_database_code_depnum_ccdc_archive 'CCDC 606099'
data_CCDC606100

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,2':6',2''-Terpyridinium picrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N3, C6 H2 N3 O7'
_chemical_formula_sum            'C21 H14 N6 O7'
_chemical_formula_weight         462.38

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
_symmetry_int_tables_number      2
_symmetry_space_group_name_Hall  -P_1

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

_cell_length_a                   8.2700(5)
_cell_length_b                   10.6206(6)
_cell_length_c                   11.4612(7)
_cell_angle_alpha                82.1260(10)
_cell_angle_beta                 86.8830(10)
_cell_angle_gamma                71.8560(10)
_cell_volume                     947.52(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6664
_cell_measurement_theta_min      2.592
_cell_measurement_theta_max      37.4585

_exptl_crystal_description       rhomb
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17639
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         37.52
_reflns_number_total             9451
_reflns_number_gt                6789
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.0885P)²+0.1043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9451
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
N011 N 0.81541(11) 0.07142(8) 0.79363(8) 0.02162(15) Uani 1 1 d . . .
C012 C 0.79160(14) 0.00937(10) 0.70474(9) 0.02396(18) Uani 1 1 d . . .
H012 H 0.8760(17) -0.0799(14) 0.7001(13) 0.025(3) Uiso 1 1 d . . .
C013 C 0.65976(15) 0.06302(10) 0.62485(9) 0.02558(19) Uani 1 1 d . . .
H013 H 0.648(2) 0.0160(16) 0.5605(14) 0.034(4) Uiso 1 1 d . . .
C014 C 0.54433(15) 0.18631(10) 0.63935(9) 0.02537(19) Uani 1 1 d . . .
H014 H 0.4466(19) 0.2250(16) 0.5878(14) 0.032(4) Uiso 1 1 d . . .
C015 C 0.56678(13) 0.25391(9) 0.72981(9) 0.02197(17) Uani 1 1 d . . .
H015 H 0.4872(19) 0.3409(16) 0.7421(13) 0.030(4) Uiso 1 1 d . . .
C016 C 0.70574(12) 0.19345(9) 0.80394(8) 0.01816(15) Uani 1 1 d . . .
N021 N 0.68230(10) 0.39739(8) 0.88480(7) 0.01729(13) Uani 1 1 d . . .
C022 C 0.74470(11) 0.26342(9) 0.89779(8) 0.01772(15) Uani 1 1 d . . .
C023 C 0.84827(12) 0.19160(10) 0.99258(8) 0.02114(17) Uani 1 1 d . . .
H023 H 0.8880(16) 0.0908(13) 0.9998(11) 0.018(3) Uiso 1 1 d . . .
C024 C 0.89039(13) 0.26056(10) 1.07444(9) 0.02212(17) Uani 1 1 d . . .
H024 H 0.961(2) 0.2116(17) 1.1415(15) 0.036(4) Uiso 1 1 d . . .
C025 C 0.83013(12) 0.39956(10) 1.06071(8) 0.01994(16) Uani 1 1 d . . .
H025 H 0.8559(19) 0.4491(16) 1.1158(14) 0.032(4) Uiso 1 1 d . . .
C026 C 0.72646(11) 0.46288(9) 0.96434(8) 0.01656(14) Uani 1 1 d . . .
N031 N 0.54907(10) 0.66118(8) 0.85020(7) 0.01761(13) Uani 1 1 d . . .
H031 H 0.519(2) 0.6036(18) 0.8132(16) 0.043(5) Uiso 1 1 d . . .
C032 C 0.66016(11) 0.61020(9) 0.94008(7) 0.01641(14) Uani 1 1 d . . .
C033 C 0.70709(12) 0.69878(9) 0.99949(8) 0.01889(15) Uani 1 1 d . . .
H033 H 0.783(2) 0.6700(16) 1.0638(15) 0.035(4) Uiso 1 1 d . . .
C034 C 0.64368(13) 0.83472(10) 0.96212(8) 0.02132(17) Uani 1 1 d . . .
H034 H 0.6784(19) 0.8993(15) 0.9998(13) 0.029(4) Uiso 1 1 d . . .
C035 C 0.53013(13) 0.88266(10) 0.86945(9) 0.02109(16) Uani 1 1 d . . .
H035 H 0.4827(18) 0.9763(15) 0.8401(13) 0.028(4) Uiso 1 1 d . . .
C036 C 0.48295(12) 0.79236(9) 0.81416(8) 0.02017(16) Uani 1 1 d . . .
H036 H 0.4027(18) 0.8180(15) 0.7524(13) 0.025(3) Uiso 1 1 d . . .
O1 O -0.09813(12) 0.58480(8) 0.24249(8) 0.0348(2) Uani 1 1 d . . .
C1 C -0.00629(12) 0.60340(9) 0.31568(8) 0.01904(16) Uani 1 1 d . . .
C2 C 0.13363(11) 0.49977(9) 0.37846(8) 0.01666(14) Uani 1 1 d . . .
C3 C 0.22135(11) 0.52161(9) 0.46891(8) 0.01697(14) Uani 1 1 d . . .
H3 H 0.3117(18) 0.4489(15) 0.5093(13) 0.028(4) Uiso 1 1 d . . .
C4 C 0.17566(11) 0.64771(9) 0.50526(8) 0.01687(14) Uani 1 1 d . . .
C5 C 0.04825(12) 0.75457(9) 0.44836(8) 0.01768(15) Uani 1 1 d . . .
H5 H 0.0240(18) 0.8404(16) 0.4728(13) 0.028(4) Uiso 1 1 d . . .
C6 C -0.03233(11) 0.73371(9) 0.35525(8) 0.01748(15) Uani 1 1 d . . .
N2 N 0.18175(10) 0.36404(8) 0.35012(7) 0.01879(14) Uani 1 1 d . . .
O21 O 0.10869(11) 0.33785(8) 0.27028(8) 0.02952(17) Uani 1 1 d . . .
O22 O 0.29714(12) 0.27769(8) 0.40680(7) 0.03082(18) Uani 1 1 d . . .
N4 N 0.26056(10) 0.67018(8) 0.60280(7) 0.01980(14) Uani 1 1 d . . .
O41 O 0.38531(10) 0.57949(8) 0.64661(7) 0.02721(16) Uani 1 1 d . . .
O42 O 0.20589(11) 0.77984(8) 0.63969(7) 0.02911(17) Uani 1 1 d . . .
N6 N -0.15485(11) 0.85094(8) 0.29377(7) 0.02113(15) Uani 1 1 d . . .
O61 O -0.17817(11) 0.85257(8) 0.18864(7) 0.03114(18) Uani 1 1 d . . .
O62 O -0.22723(11) 0.94446(8) 0.34953(8) 0.03189(18) 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
N011 C012 1.3407(13) . ?
N011 C016 1.3470(12) . ?
C012 C013 1.3894(15) . ?
C012 H012 0.993(14) . ?
C013 C014 1.3846(16) . ?
C013 H013 0.970(16) . ?
C014 C015 1.3902(14) . ?
C014 H014 0.975(15) . ?
C015 C016 1.3972(13) . ?
C015 H015 0.976(15) . ?
C016 C022 1.4896(12) . ?
N021 C022 1.3439(12) . ?
N021 C026 1.3477(11) . ?
C022 C023 1.4010(13) . ?
C023 C024 1.3860(13) . ?
C023 H023 1.010(13) . ?
C024 C025 1.3925(14) . ?
C024 H024 0.977(16) . ?
C025 C026 1.3956(12) . ?
C025 H025 0.947(16) . ?
C026 C032 1.4796(12) . ?
N031 C036 1.3428(12) . ?
N031 C032 1.3559(11) . ?
N031 H031 0.890(18) . ?
C032 C033 1.3897(12) . ?
C033 C034 1.3879(13) . ?
C033 H033 0.951(16) . ?
C034 C035 1.3899(13) . ?
C034 H034 0.978(15) . ?
C035 C036 1.3785(13) . ?
C035 H035 0.967(15) . ?
C036 H036 0.949(15) . ?
O1 C1 1.2360(11) . ?
C1 C6 1.4640(13) . ?
C1 C2 1.4658(13) . ?
C2 C3 1.3810(12) . ?
C2 N2 1.4487(11) . ?
C3 C4 1.3895(12) . ?
C3 H3 0.974(15) . ?
C4 C5 1.3967(12) . ?
C4 N4 1.4362(11) . ?
C5 C6 1.3660(12) . ?
C5 H5 0.948(16) . ?
C6 N6 1.4577(12) . ?
N2 O21 1.2306(11) . ?
N2 O22 1.2381(11) . ?
N4 O42 1.2352(11) . ?
N4 O41 1.2446(11) . ?
N6 O61 1.2275(11) . ?
N6 O62 1.2310(11) . ?

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
C012 N011 C016 117.42(9) . . ?
N011 C012 C013 123.72(10) . . ?
N011 C012 H012 114.6(8) . . ?
C013 C012 H012 121.7(8) . . ?
C014 C013 C012 118.13(9) . . ?
C014 C013 H013 120.4(9) . . ?
C012 C013 H013 121.5(9) . . ?
C013 C014 C015 119.49(9) . . ?
C013 C014 H014 120.5(10) . . ?
C015 C014 H014 120.0(10) . . ?
C014 C015 C016 118.23(9) . . ?
C014 C015 H015 121.2(9) . . ?
C016 C015 H015 120.6(9) . . ?
N011 C016 C015 122.93(9) . . ?
N011 C016 C022 115.70(8) . . ?
C015 C016 C022 121.34(8) . . ?
C022 N021 C026 118.00(8) . . ?
N021 C022 C023 121.98(8) . . ?
N021 C022 C016 117.23(8) . . ?
C023 C022 C016 120.74(8) . . ?
C024 C023 C022 119.18(9) . . ?
C024 C023 H023 122.1(7) . . ?
C022 C023 H023 118.7(7) . . ?
C023 C024 C025 119.56(9) . . ?
C023 C024 H024 120.0(10) . . ?
C025 C024 H024 120.4(10) . . ?
C024 C025 C026 117.41(8) . . ?
C024 C025 H025 121.3(10) . . ?
C026 C025 H025 121.3(10) . . ?
N021 C026 C025 123.84(8) . . ?
N021 C026 C032 114.59(7) . . ?
C025 C026 C032 121.55(8) . . ?
C036 N031 C032 123.90(8) . . ?
C036 N031 H031 118.6(11) . . ?
C032 N031 H031 117.5(11) . . ?
N031 C032 C033 118.20(8) . . ?
N031 C032 C026 116.67(8) . . ?
C033 C032 C026 125.10(8) . . ?
C034 C033 C032 119.00(8) . . ?
C034 C033 H033 118.3(10) . . ?
C032 C033 H033 122.6(10) . . ?
C033 C034 C035 120.85(8) . . ?
C033 C034 H034 121.0(9) . . ?
C035 C034 H034 118.2(9) . . ?
C036 C035 C034 118.70(9) . . ?
C036 C035 H035 117.3(9) . . ?
C034 C035 H035 124.0(9) . . ?
N031 C036 C035 119.31(8) . . ?
N031 C036 H036 117.4(9) . . ?
C035 C036 H036 123.3(9) . . ?
O1 C1 C6 122.97(9) . . ?
O1 C1 C2 125.47(9) . . ?
C6 C1 C2 111.47(7) . . ?
C3 C2 N2 116.24(8) . . ?
C3 C2 C1 123.77(8) . . ?
N2 C2 C1 119.93(7) . . ?
C2 C3 C4 119.41(8) . . ?
C2 C3 H3 120.8(9) . . ?
C4 C3 H3 119.8(9) . . ?
C3 C4 C5 121.29(8) . . ?
C3 C4 N4 119.96(8) . . ?
C5 C4 N4 118.75(8) . . ?
C6 C5 C4 118.91(8) . . ?
C6 C5 H5 121.8(9) . . ?
C4 C5 H5 119.2(9) . . ?
C5 C6 N6 116.44(8) . . ?
C5 C6 C1 124.74(8) . . ?
N6 C6 C1 118.81(7) . . ?
O21 N2 O22 121.87(8) . . ?
O21 N2 C2 119.52(8) . . ?
O22 N2 C2 118.60(8) . . ?
O42 N4 O41 122.70(8) . . ?
O42 N4 C4 118.08(8) . . ?
O41 N4 C4 119.22(8) . . ?
O61 N6 O62 123.33(9) . . ?
O61 N6 C6 118.45(8) . . ?
O62 N6 C6 118.21(8) . . ?

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
C016 N011 C012 C013 -0.99(16) . . . . ?
N011 C012 C013 C014 -1.42(17) . . . . ?
C012 C013 C014 C015 2.15(16) . . . . ?
C013 C014 C015 C016 -0.56(16) . . . . ?
C012 N011 C016 C015 2.73(14) . . . . ?
C012 N011 C016 C022 -175.31(9) . . . . ?
C014 C015 C016 N011 -1.98(15) . . . . ?
C014 C015 C016 C022 175.95(9) . . . . ?
C026 N021 C022 C023 2.05(13) . . . . ?
C026 N021 C022 C016 -175.30(8) . . . . ?
N011 C016 C022 N021 156.08(8) . . . . ?
C015 C016 C022 N021 -21.99(13) . . . . ?
N011 C016 C022 C023 -21.30(13) . . . . ?
C015 C016 C022 C023 160.63(9) . . . . ?
N021 C022 C023 C024 -1.18(15) . . . . ?
C016 C022 C023 C024 176.08(9) . . . . ?
C022 C023 C024 C025 -0.39(15) . . . . ?
C023 C024 C025 C026 0.97(15) . . . . ?
C022 N021 C026 C025 -1.43(13) . . . . ?
C022 N021 C026 C032 176.81(8) . . . . ?
C024 C025 C026 N021 -0.07(14) . . . . ?
C024 C025 C026 C032 -178.19(9) . . . . ?
C036 N031 C032 C033 0.78(14) . . . . ?
C036 N031 C032 C026 -177.22(8) . . . . ?
N021 C026 C032 N031 7.16(12) . . . . ?
C025 C026 C032 N031 -174.55(8) . . . . ?
N021 C026 C032 C033 -170.68(9) . . . . ?
C025 C026 C032 C033 7.61(14) . . . . ?
N031 C032 C033 C034 -2.26(13) . . . . ?
C026 C032 C033 C034 175.55(9) . . . . ?
C032 C033 C034 C035 2.28(15) . . . . ?
C033 C034 C035 C036 -0.76(15) . . . . ?
C032 N031 C036 C035 0.76(14) . . . . ?
C034 C035 C036 N031 -0.76(15) . . . . ?
O1 C1 C2 C3 -172.58(10) . . . . ?
C6 C1 C2 C3 4.06(13) . . . . ?
O1 C1 C2 N2 4.61(15) . . . . ?
C6 C1 C2 N2 -178.75(8) . . . . ?
N2 C2 C3 C4 -176.47(8) . . . . ?
C1 C2 C3 C4 0.82(14) . . . . ?
C2 C3 C4 C5 -3.17(14) . . . . ?
C2 C3 C4 N4 177.11(8) . . . . ?
C3 C4 C5 C6 0.02(14) . . . . ?
N4 C4 C5 C6 179.75(8) . . . . ?
C4 C5 C6 N6 -175.47(8) . . . . ?
C4 C5 C6 C1 5.75(14) . . . . ?
O1 C1 C6 C5 169.28(10) . . . . ?
C2 C1 C6 C5 -7.46(13) . . . . ?
O1 C1 C6 N6 -9.47(15) . . . . ?
C2 C1 C6 N6 173.79(8) . . . . ?
C3 C2 N2 O21 -179.89(9) . . . . ?
C1 C2 N2 O21 2.71(13) . . . . ?
C3 C2 N2 O22 -0.57(13) . . . . ?
C1 C2 N2 O22 -177.97(9) . . . . ?
C3 C4 N4 O42 -173.25(9) . . . . ?
C5 C4 N4 O42 7.01(13) . . . . ?
C3 C4 N4 O41 6.80(13) . . . . ?
C5 C4 N4 O41 -172.94(9) . . . . ?
C5 C6 N6 O61 150.89(10) . . . . ?
C1 C6 N6 O61 -30.26(13) . . . . ?
C5 C6 N6 O62 -27.68(13) . . . . ?
C1 C6 N6 O62 151.17(9) . . . . ?

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
N031 H031 O41 0.890(18) 2.339(18) 3.1083(10) 144.6(15) .
N031 H031 N021 0.890(18) 2.254(17) 2.6534(11) 106.9(13) .
C014 H014 O22 0.975(15) 2.382(15) 3.2974(13) 156.3(13) .
C036 H036 O42 0.949(15) 2.295(14) 3.1665(12) 152.4(12) .
C033 H033 O1 0.951(16) 2.265(16) 3.1884(12) 163.6(13) 1_656
C025 H025 O1 0.947(16) 2.303(16) 3.2476(12) 175.3(14) 1_656

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.718
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.085

_database_code_depnum_ccdc_archive 'CCDC 606100'
data_CCDC606101

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,9-Dimethyl-1,10-phenanthrolinium picrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C14 H13 N2'
_chemical_formula_sum            'C20 H15 N5 O7'
_chemical_formula_weight         437.37

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
_symmetry_int_tables_number      2
_symmetry_space_group_name_Hall  -P_1

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

_cell_length_a                   8.2754(16)
_cell_length_b                   10.872(2)
_cell_length_c                   11.452(2)
_cell_angle_alpha                98.064(4)
_cell_angle_beta                 104.517(3)
_cell_angle_gamma                102.449(4)
_cell_volume                     953.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2731
_cell_measurement_theta_min      2.4195
_cell_measurement_theta_max      30.047

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11218
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         30.17
_reflns_number_total             5564
_reflns_number_gt                3260
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.0952P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5564
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1408
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
N011 N 0.51448(19) 0.58701(15) 0.20797(13) 0.0226(3) Uani 1 1 d . . .
C012 C 0.6199(2) 0.53553(19) 0.28129(17) 0.0242(4) Uani 1 1 d . . .
C013 C 0.6029(2) 0.40205(19) 0.26322(18) 0.0248(4) Uani 1 1 d . . .
H013 H 0.677(3) 0.369(2) 0.317(2) 0.042(7) Uiso 1 1 d . . .
C014 C 0.4756(2) 0.32074(19) 0.16663(18) 0.0246(4) Uani 1 1 d . . .
H014 H 0.467(3) 0.231(2) 0.155(2) 0.029(6) Uiso 1 1 d . . .
C015 C 0.3634(2) 0.37182(17) 0.08491(16) 0.0213(4) Uani 1 1 d . . .
C016 C 0.3890(2) 0.50629(17) 0.11147(15) 0.0191(4) Uani 1 1 d . . .
C017 C 0.2329(2) 0.29371(19) -0.02131(17) 0.0242(4) Uani 1 1 d . . .
H017 H 0.223(3) 0.202(2) -0.035(2) 0.033(6) Uiso 1 1 d . . .
C018 C 0.7647(3) 0.6242(2) 0.3852(2) 0.0335(5) Uani 1 1 d . . .
H01A H 0.780(3) 0.714(2) 0.376(2) 0.037(6) Uiso 1 1 d . . .
H01B H 0.871(3) 0.598(3) 0.393(2) 0.056(8) Uiso 1 1 d . . .
H01C H 0.739(3) 0.624(3) 0.463(3) 0.056(8) Uiso 1 1 d . . .
N021 N 0.29643(19) 0.69031(15) 0.04939(14) 0.0199(3) Uani 1 1 d . . .
H021 H 0.376(3) 0.744(2) 0.121(2) 0.049(7) Uiso 1 1 d . . .
C022 C 0.2013(2) 0.74843(18) -0.02590(16) 0.0224(4) Uani 1 1 d . . .
C023 C 0.0745(2) 0.67161(19) -0.13170(17) 0.0226(4) Uani 1 1 d . . .
H023 H 0.014(3) 0.717(2) -0.183(2) 0.035(6) Uiso 1 1 d . . .
C024 C 0.0489(2) 0.54234(19) -0.15648(17) 0.0226(4) Uani 1 1 d . . .
H024 H -0.045(3) 0.488(2) -0.227(2) 0.050(7) Uiso 1 1 d . . .
C025 C 0.1506(2) 0.48225(17) -0.07668(15) 0.0199(4) Uani 1 1 d . . .
C026 C 0.2775(2) 0.56044(17) 0.02793(15) 0.0185(4) Uani 1 1 d . . .
C027 C 0.1303(2) 0.34664(18) -0.09925(18) 0.0245(4) Uani 1 1 d . . .
H027 H 0.043(3) 0.294(2) -0.172(2) 0.037(6) Uiso 1 1 d . . .
C028 C 0.2305(3) 0.8896(2) 0.0059(2) 0.0318(5) Uani 1 1 d . . .
H02A H 0.322(5) 0.927(3) 0.069(3) 0.089(11) Uiso 1 1 d . . .
H02B H 0.132(4) 0.915(3) 0.023(3) 0.085(11) Uiso 1 1 d . . .
H02C H 0.251(4) 0.924(3) -0.057(3) 0.080(10) Uiso 1 1 d . . .
O1 O 0.5039(2) 0.88363(13) 0.23938(12) 0.0356(4) Uani 1 1 d . . .
C1 C 0.5725(2) 0.90750(18) 0.35229(17) 0.0246(4) Uani 1 1 d . . .
C2 C 0.5217(2) 0.82971(18) 0.43673(17) 0.0235(4) Uani 1 1 d . . .
C3 C 0.6160(2) 0.84487(19) 0.55721(17) 0.0233(4) Uani 1 1 d . . .
H3 H 0.580(3) 0.787(2) 0.6078(19) 0.028(6) Uiso 1 1 d . . .
C4 C 0.7654(2) 0.94402(18) 0.60515(16) 0.0220(4) Uani 1 1 d . . .
C5 C 0.8181(2) 1.02956(18) 0.53520(17) 0.0222(4) Uani 1 1 d . . .
H5 H 0.921(3) 1.103(2) 0.568(2) 0.039(6) Uiso 1 1 d . . .
C6 C 0.7230(2) 1.01416(17) 0.41522(16) 0.0219(4) Uani 1 1 d . . .
N2 N 0.3634(2) 0.72718(17) 0.39323(15) 0.0312(4) Uani 1 1 d . . .
O21 O 0.24895(18) 0.73469(15) 0.30483(15) 0.0414(4) Uani 1 1 d . . .
O22 O 0.3490(2) 0.63759(18) 0.44724(15) 0.0560(5) Uani 1 1 d . . .
N4 N 0.8690(2) 0.95833(16) 0.72998(14) 0.0253(4) Uani 1 1 d . . .
O41 O 0.82272(18) 0.87993(14) 0.79029(12) 0.0325(3) Uani 1 1 d . . .
O42 O 1.00138(19) 1.04750(14) 0.77056(13) 0.0343(4) Uani 1 1 d . . .
N6 N 0.7786(2) 1.11227(15) 0.34953(15) 0.0263(4) Uani 1 1 d . . .
O61 O 0.6737(2) 1.12655(15) 0.25943(14) 0.0404(4) Uani 1 1 d . . .
O62 O 0.92812(19) 1.17998(14) 0.38847(14) 0.0369(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
N011 C012 1.325(2) . ?
N011 C016 1.353(2) . ?
C012 C013 1.408(3) . ?
C012 C018 1.499(3) . ?
C013 C014 1.362(3) . ?
C013 H013 0.92(2) . ?
C014 C015 1.406(3) . ?
C014 H014 0.95(2) . ?
C015 C016 1.409(2) . ?
C015 C017 1.422(3) . ?
C016 C026 1.436(2) . ?
C017 C027 1.351(3) . ?
C017 H017 0.97(2) . ?
C018 H01A 0.98(2) . ?
C018 H01B 0.97(3) . ?
C018 H01C 0.97(3) . ?
N021 C022 1.338(2) . ?
N021 C026 1.366(2) . ?
N021 H021 0.93(3) . ?
C022 C023 1.403(2) . ?
C022 C028 1.478(3) . ?
C023 C024 1.353(3) . ?
C023 H023 0.93(2) . ?
C024 C025 1.410(3) . ?
C024 H024 0.98(3) . ?
C025 C026 1.400(2) . ?
C025 C027 1.426(3) . ?
C027 H027 0.96(2) . ?
C028 H02A 0.88(3) . ?
C028 H02B 0.97(3) . ?
C028 H02C 0.90(3) . ?
O1 C1 1.239(2) . ?
C1 C2 1.452(3) . ?
C1 C6 1.452(3) . ?
C2 C3 1.371(3) . ?
C2 N2 1.447(2) . ?
C3 C4 1.383(3) . ?
C3 H3 0.96(2) . ?
C4 C5 1.381(3) . ?
C4 N4 1.438(2) . ?
C5 C6 1.368(2) . ?
C5 H5 0.98(2) . ?
C6 N6 1.450(2) . ?
N2 O22 1.225(2) . ?
N2 O21 1.227(2) . ?
N4 O41 1.228(2) . ?
N4 O42 1.232(2) . ?
N6 O61 1.223(2) . ?
N6 O62 1.229(2) . ?

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
C012 N011 C016 117.46(17) . . ?
N011 C012 C013 122.48(17) . . ?
N011 C012 C018 118.13(18) . . ?
C013 C012 C018 119.37(17) . . ?
C014 C013 C012 120.01(18) . . ?
C014 C013 H013 119.9(15) . . ?
C012 C013 H013 120.0(15) . . ?
C013 C014 C015 119.29(18) . . ?
C013 C014 H014 118.9(13) . . ?
C015 C014 H014 121.8(13) . . ?
C016 C015 C014 116.59(16) . . ?
C016 C015 C017 120.87(16) . . ?
C014 C015 C017 122.52(17) . . ?
N011 C016 C015 124.15(16) . . ?
N011 C016 C026 118.43(16) . . ?
C015 C016 C026 117.39(15) . . ?
C027 C017 C015 120.81(18) . . ?
C027 C017 H017 122.3(13) . . ?
C015 C017 H017 116.9(13) . . ?
C012 C018 H01A 111.5(13) . . ?
C012 C018 H01B 111.3(16) . . ?
H01A C018 H01B 112(2) . . ?
C012 C018 H01C 111.1(16) . . ?
H01A C018 H01C 104(2) . . ?
H01B C018 H01C 107(2) . . ?
C022 N021 C026 123.41(15) . . ?
C022 N021 H021 115.5(15) . . ?
C026 N021 H021 121.1(15) . . ?
N021 C022 C023 118.13(17) . . ?
N021 C022 C028 119.37(17) . . ?
C023 C022 C028 122.48(17) . . ?
C024 C023 C022 120.83(17) . . ?
C024 C023 H023 124.3(14) . . ?
C022 C023 H023 114.8(14) . . ?
C023 C024 C025 120.51(17) . . ?
C023 C024 H024 121.1(15) . . ?
C025 C024 H024 118.3(15) . . ?
C026 C025 C024 117.92(16) . . ?
C026 C025 C027 119.32(16) . . ?
C024 C025 C027 122.75(16) . . ?
N021 C026 C025 119.19(15) . . ?
N021 C026 C016 119.83(15) . . ?
C025 C026 C016 120.98(16) . . ?
C017 C027 C025 120.62(17) . . ?
C017 C027 H027 121.1(13) . . ?
C025 C027 H027 118.3(13) . . ?
C022 C028 H02A 113(2) . . ?
C022 C028 H02B 113.0(19) . . ?
H02A C028 H02B 108(3) . . ?
C022 C028 H02C 110(2) . . ?
H02A C028 H02C 105(3) . . ?
H02B C028 H02C 107(3) . . ?
O1 C1 C2 125.18(18) . . ?
O1 C1 C6 123.20(18) . . ?
C2 C1 C6 111.51(16) . . ?
C3 C2 N2 116.37(17) . . ?
C3 C2 C1 124.29(17) . . ?
N2 C2 C1 119.33(16) . . ?
C2 C3 C4 118.98(18) . . ?
C2 C3 H3 120.8(13) . . ?
C4 C3 H3 120.2(13) . . ?
C5 C4 C3 121.26(17) . . ?
C5 C4 N4 119.13(16) . . ?
C3 C4 N4 119.61(17) . . ?
C6 C5 C4 119.42(17) . . ?
C6 C5 H5 117.5(13) . . ?
C4 C5 H5 123.0(13) . . ?
C5 C6 N6 116.61(16) . . ?
C5 C6 C1 124.02(17) . . ?
N6 C6 C1 119.37(16) . . ?
O22 N2 O21 122.97(18) . . ?
O22 N2 C2 118.55(17) . . ?
O21 N2 C2 118.47(18) . . ?
O41 N4 O42 123.16(16) . . ?
O41 N4 C4 118.48(16) . . ?
O42 N4 C4 118.36(16) . . ?
O61 N6 O62 122.58(16) . . ?
O61 N6 C6 118.75(16) . . ?
O62 N6 C6 118.65(15) . . ?

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
C016 N011 C012 C013 -1.3(3) . . . . ?
C016 N011 C012 C018 177.24(17) . . . . ?
N011 C012 C013 C014 0.7(3) . . . . ?
C018 C012 C013 C014 -177.75(19) . . . . ?
C012 C013 C014 C015 0.8(3) . . . . ?
C013 C014 C015 C016 -1.6(3) . . . . ?
C013 C014 C015 C017 176.85(18) . . . . ?
C012 N011 C016 C015 0.3(3) . . . . ?
C012 N011 C016 C026 -177.56(16) . . . . ?
C014 C015 C016 N011 1.1(3) . . . . ?
C017 C015 C016 N011 -177.38(17) . . . . ?
C014 C015 C016 C026 179.02(16) . . . . ?
C017 C015 C016 C026 0.5(3) . . . . ?
C016 C015 C017 C027 0.0(3) . . . . ?
C014 C015 C017 C027 -178.43(18) . . . . ?
C026 N021 C022 C023 0.6(3) . . . . ?
C026 N021 C022 C028 179.48(18) . . . . ?
N021 C022 C023 C024 0.2(3) . . . . ?
C028 C022 C023 C024 -178.6(2) . . . . ?
C022 C023 C024 C025 -0.5(3) . . . . ?
C023 C024 C025 C026 0.0(3) . . . . ?
C023 C024 C025 C027 -179.26(17) . . . . ?
C022 N021 C026 C025 -1.1(3) . . . . ?
C022 N021 C026 C016 177.95(16) . . . . ?
C024 C025 C026 N021 0.8(3) . . . . ?
C027 C025 C026 N021 -179.91(16) . . . . ?
C024 C025 C026 C016 -178.27(16) . . . . ?
C027 C025 C026 C016 1.0(3) . . . . ?
N011 C016 C026 N021 -2.1(2) . . . . ?
C015 C016 C026 N021 179.91(15) . . . . ?
N011 C016 C026 C025 177.01(16) . . . . ?
C015 C016 C026 C025 -1.0(3) . . . . ?
C015 C017 C027 C025 0.0(3) . . . . ?
C026 C025 C027 C017 -0.5(3) . . . . ?
C024 C025 C027 C017 178.75(17) . . . . ?
O1 C1 C2 C3 168.55(19) . . . . ?
C6 C1 C2 C3 -7.7(3) . . . . ?
O1 C1 C2 N2 -10.3(3) . . . . ?
C6 C1 C2 N2 173.47(16) . . . . ?
N2 C2 C3 C4 -177.85(17) . . . . ?
C1 C2 C3 C4 3.3(3) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C2 C3 C4 N4 -177.79(17) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
N4 C4 C5 C6 178.05(16) . . . . ?
C4 C5 C6 N6 175.86(16) . . . . ?
C4 C5 C6 C1 -3.8(3) . . . . ?
O1 C1 C6 C5 -168.38(19) . . . . ?
C2 C1 C6 C5 7.9(3) . . . . ?
O1 C1 C6 N6 12.0(3) . . . . ?
C2 C1 C6 N6 -171.72(16) . . . . ?
C3 C2 N2 O22 -22.8(3) . . . . ?
C1 C2 N2 O22 156.11(19) . . . . ?
C3 C2 N2 O21 156.30(18) . . . . ?
C1 C2 N2 O21 -24.8(3) . . . . ?
C5 C4 N4 O41 -178.40(17) . . . . ?
C3 C4 N4 O41 1.3(3) . . . . ?
C5 C4 N4 O42 0.4(3) . . . . ?
C3 C4 N4 O42 -179.93(18) . . . . ?
C5 C6 N6 O61 -157.57(17) . . . . ?
C1 C6 N6 O61 22.1(3) . . . . ?
C5 C6 N6 O62 20.6(2) . . . . ?
C1 C6 N6 O62 -159.71(17) . . . . ?

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
N021 H021 O1 0.93(3) 1.81(3) 2.718(2) 164(2) .

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1.000

_refine_diff_density_max         0.538
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.079

_database_code_depnum_ccdc_archive 'CCDC 606101'
data_CCDC606102

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Piperidinium picrate mono-piperidine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C5 H11 N, C5 H12 N'
_chemical_formula_sum            'C16 H25 N5 O7'
_chemical_formula_weight         399.41

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   P_21/n
_symmetry_int_tables_number      14
_symmetry_space_group_name_Hall  -P_2yn

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

_cell_length_a                   6.5862(5)
_cell_length_b                   16.8945(13)
_cell_length_c                   17.1437(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.306(2)
_cell_angle_gamma                90.00
_cell_volume                     1882.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6071
_cell_measurement_theta_min      2.4075
_cell_measurement_theta_max      34.583

_exptl_crystal_description       cubiod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29353
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         37.57
_reflns_number_total             9889
_reflns_number_gt                6005
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.0886P)²+0.1617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9889
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N011 N 0.44445(16) 0.27583(6) 0.16423(6) 0.02410(19) Uani 1 1 d . . . . .
H11A H 0.478(2) 0.2472(9) 0.1259(9) 0.029 Uiso 1 1 d . U . . .
C012 C 0.26999(19) 0.32769(8) 0.13309(8) 0.0282(2) Uani 1 1 d . . . . .
H12A H 0.229(3) 0.3552(10) 0.1777(10) 0.034 Uiso 1 1 d . U . . .
H12B H 0.160(3) 0.2928(9) 0.1086(10) 0.034 Uiso 1 1 d . U . . .
C013 C 0.3261(2) 0.38952(8) 0.07601(8) 0.0307(3) Uani 1 1 d . . . . .
H13A H 0.206(3) 0.4258(10) 0.0635(10) 0.037 Uiso 1 1 d . U . . .
H13B H 0.357(3) 0.3648(10) 0.0277(10) 0.037 Uiso 1 1 d . U . . .
C014 C 0.5125(2) 0.43738(7) 0.11360(8) 0.0316(3) Uani 1 1 d . . . . .
H14A H 0.470(3) 0.4680(10) 0.1564(11) 0.038 Uiso 1 1 d . U . . .
H14B H 0.555(3) 0.4754(10) 0.0772(10) 0.038 Uiso 1 1 d . U . . .
C015 C 0.6921(2) 0.38295(8) 0.14468(8) 0.0308(3) Uani 1 1 d . . . . .
H15A H 0.737(3) 0.3549(10) 0.0981(10) 0.037 Uiso 1 1 d . U . . .
H15B H 0.810(3) 0.4137(10) 0.1723(10) 0.037 Uiso 1 1 d . U . . .
C016 C 0.62555(19) 0.32178(7) 0.20020(7) 0.0258(2) Uani 1 1 d . . . . .
H16A H 0.736(2) 0.2816(9) 0.2187(9) 0.031 Uiso 1 1 d . U . . .
H16B H 0.587(2) 0.3489(9) 0.2442(10) 0.031 Uiso 1 1 d . U . . .
N021 N 0.32857(15) 0.16905(5) 0.26477(5) 0.02180(17) Uani 1 1 d D . . . .
H21A H 0.261(2) 0.1297(9) 0.2348(9) 0.026 Uiso 1 1 d . U . . .
H21B H 0.366(2) 0.2044(7) 0.2321(7) 0.026 Uiso 1 1 d D U . . .
C022 C 0.19099(18) 0.20981(7) 0.31259(7) 0.0247(2) Uani 1 1 d . . . . .
H22A H 0.070(2) 0.2273(9) 0.2758(9) 0.030 Uiso 1 1 d . U . . .
H22B H 0.266(2) 0.2563(10) 0.3352(9) 0.030 Uiso 1 1 d . U . . .
C023 C 0.1340(2) 0.15664(8) 0.37670(8) 0.0309(3) Uani 1 1 d . . . . .
H23A H 0.052(3) 0.1134(10) 0.3528(10) 0.037 Uiso 1 1 d . U . . .
H23B H 0.047(3) 0.1879(10) 0.4065(10) 0.037 Uiso 1 1 d . U . . .
C024 C 0.3249(2) 0.12284(8) 0.42795(7) 0.0325(3) Uani 1 1 d . . . . .
H24A H 0.411(3) 0.1653(10) 0.4575(10) 0.039 Uiso 1 1 d . U . . .
H24B H 0.287(3) 0.0847(10) 0.4712(10) 0.039 Uiso 1 1 d . U . . .
C025 C 0.4615(2) 0.08127(8) 0.37691(7) 0.0281(2) Uani 1 1 d . . . . .
H25A H 0.585(3) 0.0642(10) 0.4092(10) 0.034 Uiso 1 1 d . U . . .
H25B H 0.384(3) 0.0340(10) 0.3522(10) 0.034 Uiso 1 1 d . U . . .
C026 C 0.51617(18) 0.13631(7) 0.31365(7) 0.0247(2) Uani 1 1 d . . . . .
H26A H 0.593(2) 0.1814(9) 0.3354(9) 0.030 Uiso 1 1 d . U . . .
H26B H 0.590(2) 0.1087(9) 0.2780(9) 0.030 Uiso 1 1 d . U . . .
O1 O 0.32741(14) 0.10691(5) 0.11239(5) 0.02497(17) Uani 1 1 d . . . . .
C1 C 0.29232(14) 0.05544(6) 0.06044(6) 0.01600(16) Uani 1 1 d . . . . .
C2 C 0.30673(14) -0.02921(6) 0.07549(6) 0.01616(16) Uani 1 1 d . . . . .
C3 C 0.27277(15) -0.08690(6) 0.01872(6) 0.01808(17) Uani 1 1 d . . . . .
H3 H 0.291(2) -0.1419(9) 0.0356(8) 0.022 Uiso 1 1 d . U . . .
C4 C 0.20827(15) -0.06453(6) -0.05944(6) 0.01835(18) Uani 1 1 d . . . . .
C5 C 0.18505(15) 0.01463(6) -0.08080(6) 0.01815(17) Uani 1 1 d . . . . .
H5 H 0.140(2) 0.0291(8) -0.1340(9) 0.022 Uiso 1 1 d . U . . .
C6 C 0.23058(15) 0.07145(6) -0.02344(6) 0.01619(16) Uani 1 1 d . . . . .
N2 N 0.36506(15) -0.05573(6) 0.15652(5) 0.02204(18) Uani 1 1 d . . . . .
O21 O 0.29206(17) -0.02119(6) 0.20863(5) 0.0372(2) Uani 1 1 d . . . . .
O22 O 0.48223(15) -0.11286(5) 0.16900(6) 0.0331(2) Uani 1 1 d . . . . .
N4 N 0.16327(14) -0.12455(6) -0.11900(6) 0.0263(2) Uani 1 1 d . . . . .
O41 O 0.16764(16) -0.19438(6) -0.09793(7) 0.0382(2) Uani 1 1 d . . . . .
O42 O 0.12004(15) -0.10365(7) -0.18892(5) 0.0361(2) Uani 1 1 d . . . . .
N6 N 0.20921(14) 0.15317(5) -0.04922(5) 0.02145(17) Uani 1 1 d . . . . .
O61 O 0.32955(15) 0.20269(5) -0.01617(5) 0.0314(2) Uani 1 1 d . . . . .
O62 O 0.07086(15) 0.16871(6) -0.10488(5) 0.0330(2) 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
N011 C016 1.4723(16) . ?
N011 C012 1.4747(16) . ?
N011 H11A 0.872(16) . ?
C012 C013 1.5173(19) . ?
C012 H12A 0.970(17) . ?
C012 H12B 0.976(16) . ?
C013 C014 1.5232(19) . ?
C013 H13A 0.999(17) . ?
C013 H13B 0.978(17) . ?
C014 C015 1.5246(19) . ?
C014 H14A 0.975(18) . ?
C014 H14B 0.966(17) . ?
C015 C016 1.5168(17) . ?
C015 H15A 1.014(17) . ?
C015 H15B 0.990(18) . ?
C016 H16A 1.007(16) . ?
C016 H16B 0.952(17) . ?
N021 C026 1.4832(15) . ?
N021 C022 1.4858(15) . ?
N021 H21A 0.911(16) . ?
N021 H21B 0.880(5) . ?
C022 C023 1.5130(18) . ?
C022 H22A 0.980(16) . ?
C022 H22B 0.974(16) . ?
C023 C024 1.524(2) . ?
C023 H23A 0.958(17) . ?
C023 H23B 0.981(17) . ?
C024 C025 1.5242(18) . ?
C024 H24A 0.999(18) . ?
C024 H24B 1.043(17) . ?
C025 C026 1.5154(17) . ?
C025 H25A 0.951(17) . ?
C025 H25B 1.004(17) . ?
C026 H26A 0.956(16) . ?
C026 H26B 0.959(16) . ?
O1 C1 1.2395(12) . ?
C1 C2 1.4535(14) . ?
C1 C6 1.4551(14) . ?
C2 C3 1.3700(14) . ?
C2 N2 1.4511(13) . ?
C3 C4 1.3909(15) . ?
C3 H3 0.975(15) . ?
C4 C5 1.3885(15) . ?
C4 N4 1.4355(13) . ?
C5 C6 1.3722(14) . ?
C5 H5 0.945(15) . ?
C6 N6 1.4495(13) . ?
N2 O21 1.2284(13) . ?
N2 O22 1.2326(13) . ?
N4 O41 1.2329(15) . ?
N4 O42 1.2379(14) . ?
N6 O61 1.2263(13) . ?
N6 O62 1.2363(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
C016 N011 C012 111.67(9) . . ?
C016 N011 H11A 108.8(10) . . ?
C012 N011 H11A 109.4(10) . . ?
N011 C012 C013 112.70(10) . . ?
N011 C012 H12A 107.4(10) . . ?
C013 C012 H12A 107.9(10) . . ?
N011 C012 H12B 106.2(9) . . ?
C013 C012 H12B 112.4(10) . . ?
H12A C012 H12B 110.2(14) . . ?
C012 C013 C014 110.87(10) . . ?
C012 C013 H13A 107.1(10) . . ?
C014 C013 H13A 108.8(10) . . ?
C012 C013 H13B 110.9(10) . . ?
C014 C013 H13B 108.7(10) . . ?
H13A C013 H13B 110.4(14) . . ?
C013 C014 C015 110.75(10) . . ?
C013 C014 H14A 106.8(10) . . ?
C015 C014 H14A 111.0(10) . . ?
C013 C014 H14B 112.1(10) . . ?
C015 C014 H14B 109.8(10) . . ?
H14A C014 H14B 106.3(14) . . ?
C016 C015 C014 110.11(11) . . ?
C016 C015 H15A 109.0(10) . . ?
C014 C015 H15A 108.5(10) . . ?
C016 C015 H15B 110.0(10) . . ?
C014 C015 H15B 110.8(10) . . ?
H15A C015 H15B 108.3(14) . . ?
N011 C016 C015 113.15(10) . . ?
N011 C016 H16A 105.7(9) . . ?
C015 C016 H16A 113.0(9) . . ?
N011 C016 H16B 106.4(10) . . ?
C015 C016 H16B 108.1(10) . . ?
H16A C016 H16B 110.3(13) . . ?
C026 N021 C022 112.82(9) . . ?
C026 N021 H21A 109.4(10) . . ?
C022 N021 H21A 111.4(10) . . ?
C026 N021 H21B 108.7(10) . . ?
C022 N021 H21B 107.1(10) . . ?
H21A N021 H21B 107.2(14) . . ?
N021 C022 C023 111.75(9) . . ?
N021 C022 H22A 106.9(9) . . ?
C023 C022 H22A 112.0(9) . . ?
N021 C022 H22B 106.0(9) . . ?
C023 C022 H22B 111.1(9) . . ?
H22A C022 H22B 108.7(13) . . ?
C022 C023 C024 111.28(10) . . ?
C022 C023 H23A 109.3(10) . . ?
C024 C023 H23A 108.3(10) . . ?
C022 C023 H23B 107.0(10) . . ?
C024 C023 H23B 113.5(10) . . ?
H23A C023 H23B 107.4(14) . . ?
C025 C024 C023 110.51(10) . . ?
C025 C024 H24A 106.4(10) . . ?
C023 C024 H24A 111.7(10) . . ?
C025 C024 H24B 110.8(9) . . ?
C023 C024 H24B 111.8(10) . . ?
H24A C024 H24B 105.4(14) . . ?
C026 C025 C024 111.02(10) . . ?
C026 C025 H25A 108.9(10) . . ?
C024 C025 H25A 109.4(10) . . ?
C026 C025 H25B 110.4(9) . . ?
C024 C025 H25B 107.6(10) . . ?
H25A C025 H25B 109.4(14) . . ?
N021 C026 C025 111.14(10) . . ?
N021 C026 H26A 105.3(10) . . ?
C025 C026 H26A 112.4(10) . . ?
N021 C026 H26B 106.3(9) . . ?
C025 C026 H26B 111.1(9) . . ?
H26A C026 H26B 110.3(13) . . ?
O1 C1 C2 124.30(9) . . ?
O1 C1 C6 124.72(9) . . ?
C2 C1 C6 110.99(8) . . ?
C3 C2 N2 116.60(9) . . ?
C3 C2 C1 125.13(9) . . ?
N2 C2 C1 118.26(8) . . ?
C2 C3 C4 118.71(9) . . ?
C2 C3 H3 117.9(8) . . ?
C4 C3 H3 123.3(8) . . ?
C5 C4 C3 121.28(9) . . ?
C5 C4 N4 119.43(10) . . ?
C3 C4 N4 119.28(10) . . ?
C6 C5 C4 118.87(9) . . ?
C6 C5 H5 120.6(8) . . ?
C4 C5 H5 120.5(8) . . ?
C5 C6 N6 116.66(9) . . ?
C5 C6 C1 124.88(9) . . ?
N6 C6 C1 118.43(8) . . ?
O21 N2 O22 123.61(10) . . ?
O21 N2 C2 118.38(9) . . ?
O22 N2 C2 118.00(9) . . ?
O41 N4 O42 123.20(10) . . ?
O41 N4 C4 118.37(10) . . ?
O42 N4 C4 118.43(11) . . ?
O61 N6 O62 123.53(10) . . ?
O61 N6 C6 119.03(9) . . ?
O62 N6 C6 117.43(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
C016 N011 C012 C013 54.26(13) . . . . ?
N011 C012 C013 C014 -54.32(14) . . . . ?
C012 C013 C014 C015 54.22(14) . . . . ?
C013 C014 C015 C016 -54.27(14) . . . . ?
C012 N011 C016 C015 -55.00(13) . . . . ?
C014 C015 C016 N011 55.13(14) . . . . ?
C026 N021 C022 C023 -54.78(13) . . . . ?
N021 C022 C023 C024 53.89(13) . . . . ?
C022 C023 C024 C025 -54.29(15) . . . . ?
C023 C024 C025 C026 55.19(15) . . . . ?
C022 N021 C026 C025 55.50(12) . . . . ?
C024 C025 C026 N021 -55.58(14) . . . . ?
O1 C1 C2 C3 -178.55(10) . . . . ?
C6 C1 C2 C3 1.68(13) . . . . ?
O1 C1 C2 N2 0.28(15) . . . . ?
C6 C1 C2 N2 -179.49(8) . . . . ?
N2 C2 C3 C4 177.38(9) . . . . ?
C1 C2 C3 C4 -3.78(15) . . . . ?
C2 C3 C4 C5 2.25(14) . . . . ?
C2 C3 C4 N4 -177.23(9) . . . . ?
C3 C4 C5 C6 1.18(14) . . . . ?
N4 C4 C5 C6 -179.34(9) . . . . ?
C4 C5 C6 N6 178.34(9) . . . . ?
C4 C5 C6 C1 -3.44(14) . . . . ?
O1 C1 C6 C5 -177.74(10) . . . . ?
C2 C1 C6 C5 2.03(13) . . . . ?
O1 C1 C6 N6 0.45(15) . . . . ?
C2 C1 C6 N6 -179.79(8) . . . . ?
C3 C2 N2 O21 -140.13(11) . . . . ?
C1 C2 N2 O21 40.95(14) . . . . ?
C3 C2 N2 O22 38.44(13) . . . . ?
C1 C2 N2 O22 -140.49(10) . . . . ?
C5 C4 N4 O41 -173.82(10) . . . . ?
C3 C4 N4 O41 5.67(14) . . . . ?
C5 C4 N4 O42 5.49(14) . . . . ?
C3 C4 N4 O42 -175.02(10) . . . . ?
C5 C6 N6 O61 -145.07(10) . . . . ?
C1 C6 N6 O61 36.60(13) . . . . ?
C5 C6 N6 O62 33.74(13) . . . . ?
C1 C6 N6 O62 -144.59(10) . . . . ?

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
#N011 H11A O41  0.872(16) 2.616(16) 3.2638(14) 131.9(12) 3_655
N011 H11A O1 0.872(16) 2.565(15) 3.0506(13) 116.1(12) .
N011 H11A O61 0.872(16) 2.585(16) 3.3027(13) 140.3(13) .
N021 H21A O1 0.911(16) 2.245(16) 2.8143(12) 120.1(12) .
N021 H21A O42 0.911(16) 2.545(16) 3.2247(14) 131.8(12) 3
N021 H21A O21 0.911(16) 2.602(16) 3.3524(14) 140.2(12) .
N021 H21B N011 0.880(5) 1.809(5) 2.6894(13) 179.1(15) .

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1.000

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.076

_database_code_depnum_ccdc_archive 'CCDC 606102'
data_CCDC606103

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-Methylpyridinium picrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C6 H8 N'
_chemical_formula_sum            'C12 H10 N4 O7'
_chemical_formula_weight         322.24

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P_-1
_symmetry_int_tables_number      2
_symmetry_space_group_name_Hall  -P_1

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

_cell_length_a                   8.191(3)
_cell_length_b                   11.869(4)
_cell_length_c                   13.953(5)
_cell_angle_alpha                86.255(5)
_cell_angle_beta                 82.754(6)
_cell_angle_gamma                80.752(5)
_cell_volume                     1326.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3240
_cell_measurement_theta_min      2.847
_cell_measurement_theta_max      28.05

_exptl_crystal_description       bar
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11660
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         28.94
_reflns_number_total             6148
_reflns_number_gt                4200
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.0893P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6148
_refine_ls_number_parameters     495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
O11 O 0.74966(19) 0.26668(13) 0.10267(12) 0.0252(4) Uani 1 1 d . . .
C11 C 0.6721(3) 0.36647(18) 0.11097(15) 0.0198(5) Uani 1 1 d . . .
C12 C 0.7419(3) 0.46926(19) 0.12033(16) 0.0210(5) Uani 1 1 d . . .
C13 C 0.6484(3) 0.57495(19) 0.13770(17) 0.0222(5) Uani 1 1 d . . .
C14 C 0.4765(3) 0.58805(18) 0.14272(16) 0.0219(5) Uani 1 1 d . . .
C15 C 0.3945(3) 0.49488(19) 0.13403(16) 0.0222(5) Uani 1 1 d . . .
C16 C 0.4907(3) 0.39023(18) 0.11881(16) 0.0213(5) Uani 1 1 d . . .
N12 N 0.9221(2) 0.46472(16) 0.11250(13) 0.0219(4) Uani 1 1 d . . .
O121 O 1.0136(2) 0.38715(14) 0.06831(13) 0.0305(4) Uani 1 1 d . . .
O122 O 0.97709(19) 0.54156(14) 0.14835(12) 0.0278(4) Uani 1 1 d . . .
N14 N 0.3801(2) 0.69949(16) 0.15927(14) 0.0245(4) Uani 1 1 d . . .
O141 O 0.4498(2) 0.77613(14) 0.18482(13) 0.0316(4) Uani 1 1 d . . .
O142 O 0.2308(2) 0.71431(14) 0.14818(13) 0.0341(4) Uani 1 1 d . . .
N16 N 0.4034(2) 0.29248(16) 0.11322(15) 0.0253(4) Uani 1 1 d . . .
O161 O 0.4406(2) 0.23441(14) 0.04160(14) 0.0358(4) Uani 1 1 d . . .
O162 O 0.2978(2) 0.27406(16) 0.18078(14) 0.0396(5) Uani 1 1 d . . .
O21 O 0.2670(2) 0.28701(13) 0.41914(12) 0.0287(4) Uani 1 1 d . . .
C21 C 0.1978(3) 0.38676(18) 0.39922(16) 0.0207(5) Uani 1 1 d . . .
C22 C 0.2750(3) 0.48959(19) 0.38764(16) 0.0211(5) Uani 1 1 d . . .
C23 C 0.1886(3) 0.59681(19) 0.36921(16) 0.0209(5) Uani 1 1 d . . .
C24 C 0.0218(3) 0.61066(18) 0.35730(16) 0.0211(5) Uani 1 1 d . . .
C25 C -0.0620(3) 0.51642(19) 0.36053(16) 0.0210(5) Uani 1 1 d . . .
C26 C 0.0242(3) 0.41091(18) 0.38118(16) 0.0209(5) Uani 1 1 d . . .
N22 N 0.4528(2) 0.48270(16) 0.39126(14) 0.0244(4) Uani 1 1 d . . .
O221 O 0.5331(2) 0.39571(17) 0.4199(2) 0.0670(8) Uani 1 1 d . . .
O222 O 0.5185(2) 0.56658(15) 0.36502(18) 0.0522(6) Uani 1 1 d . . .
N24 N -0.0648(2) 0.72341(16) 0.33488(14) 0.0246(4) Uani 1 1 d . . .
O241 O 0.0115(2) 0.80555(13) 0.33075(13) 0.0313(4) Uani 1 1 d . . .
O242 O -0.2120(2) 0.73360(14) 0.31945(14) 0.0348(4) Uani 1 1 d . . .
N26 N -0.0633(2) 0.31209(16) 0.37958(15) 0.0256(5) Uani 1 1 d . . .
O261 O -0.0657(2) 0.24451(14) 0.44983(13) 0.0354(4) Uani 1 1 d . . .
O262 O -0.1296(2) 0.30308(16) 0.30705(14) 0.0419(5) Uani 1 1 d . . .
N011 N 1.0494(2) 0.15712(16) 0.03263(15) 0.0238(4) Uani 1 1 d . . .
C012 C 1.0995(3) 0.1787(2) -0.06190(18) 0.0254(5) Uani 1 1 d . . .
C013 C 1.2269(3) 0.1072(2) -0.10927(19) 0.0282(5) Uani 1 1 d . . .
C014 C 1.3019(3) 0.0119(2) -0.0587(2) 0.0317(6) Uani 1 1 d . . .
C015 C 1.2489(3) -0.0074(2) 0.0379(2) 0.0304(6) Uani 1 1 d . . .
C016 C 1.1207(3) 0.06744(19) 0.08485(17) 0.0243(5) Uani 1 1 d . . .
C017 C 1.0595(4) 0.0571(3) 0.1899(2) 0.0361(6) Uani 1 1 d . . .
N021 N 0.5432(2) 0.16893(17) 0.47939(15) 0.0242(4) Uani 1 1 d . . .
C022 C 0.5703(3) 0.1666(2) 0.57251(18) 0.0270(5) Uani 1 1 d . . .
C023 C 0.6885(3) 0.0839(2) 0.6077(2) 0.0307(6) Uani 1 1 d . . .
C024 C 0.7769(3) 0.0040(2) 0.5452(2) 0.0350(6) Uani 1 1 d . . .
C025 C 0.7474(3) 0.0089(2) 0.4496(2) 0.0328(6) Uani 1 1 d . . .
C026 C 0.6287(3) 0.09373(19) 0.41533(18) 0.0261(5) Uani 1 1 d . . .
C027 C 0.5904(4) 0.1101(3) 0.3134(2) 0.0385(7) Uani 1 1 d . . .
H13 H 0.700(3) 0.640(2) 0.1420(17) 0.024(6) Uiso 1 1 d . . .
H15 H 0.276(3) 0.503(2) 0.1374(18) 0.033(7) Uiso 1 1 d . . .
H23 H 0.235(3) 0.657(2) 0.3641(16) 0.018(6) Uiso 1 1 d . . .
H25 H -0.172(3) 0.5235(18) 0.3518(16) 0.017(6) Uiso 1 1 d . . .
H011 H 0.961(4) 0.208(2) 0.059(2) 0.040(8) Uiso 1 1 d . . .
H012 H 1.042(3) 0.245(2) -0.0855(18) 0.030(7) Uiso 1 1 d . . .
H013 H 1.262(3) 0.127(2) -0.175(2) 0.037(7) Uiso 1 1 d . . .
H014 H 1.387(3) -0.042(2) -0.0884(18) 0.030(7) Uiso 1 1 d . . .
H015 H 1.293(4) -0.067(2) 0.065(2) 0.039(8) Uiso 1 1 d . . .
H01A H 1.120(4) 0.091(3) 0.226(2) 0.049(9) Uiso 1 1 d . . .
H01B H 1.062(3) -0.022(2) 0.2134(19) 0.037(7) Uiso 1 1 d . . .
H01C H 0.944(5) 0.100(3) 0.204(3) 0.085(12) Uiso 1 1 d . . .
H021 H 0.469(4) 0.220(3) 0.456(2) 0.046(9) Uiso 1 1 d . . .
H022 H 0.502(3) 0.225(2) 0.609(2) 0.039(8) Uiso 1 1 d . . .
H023 H 0.701(3) 0.084(2) 0.673(2) 0.040(8) Uiso 1 1 d . . .
H024 H 0.858(4) -0.057(2) 0.570(2) 0.041(8) Uiso 1 1 d . . .
H025 H 0.807(4) -0.047(2) 0.404(2) 0.041(8) Uiso 1 1 d . . .
H02A H 0.468(5) 0.146(3) 0.309(2) 0.066(10) Uiso 1 1 d . . .
H02B H 0.623(4) 0.036(3) 0.276(2) 0.062(10) Uiso 1 1 d . . .
H02C H 0.653(4) 0.169(3) 0.274(2) 0.064(10) Uiso 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
O11 C11 1.256(3) . ?
C11 C12 1.448(3) . ?
C11 C16 1.458(3) . ?
C12 C13 1.380(3) . ?
C12 N12 1.459(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.94(2) . ?
C14 C15 1.402(3) . ?
C14 N14 1.444(3) . ?
C15 C16 1.373(3) . ?
C15 H15 0.95(3) . ?
C16 N16 1.468(3) . ?
N12 O121 1.235(2) . ?
N12 O122 1.238(2) . ?
N14 O142 1.235(2) . ?
N14 O141 1.241(2) . ?
N16 O161 1.230(3) . ?
N16 O162 1.230(3) . ?
O21 C21 1.257(3) . ?
C21 C22 1.453(3) . ?
C21 C26 1.455(3) . ?
C22 C23 1.379(3) . ?
C22 N22 1.453(3) . ?
C23 C24 1.379(3) . ?
C23 H23 0.85(2) . ?
C24 C25 1.399(3) . ?
C24 N24 1.445(3) . ?
C25 C26 1.367(3) . ?
C25 H25 0.92(2) . ?
C26 N26 1.472(3) . ?
N22 O221 1.205(3) . ?
N22 O222 1.220(2) . ?
N24 O241 1.234(2) . ?
N24 O242 1.237(2) . ?
N26 O261 1.226(2) . ?
N26 O262 1.226(3) . ?
N011 C016 1.346(3) . ?
N011 C012 1.352(3) . ?
N011 H011 0.91(3) . ?
C012 C013 1.364(4) . ?
C012 H012 0.92(3) . ?
C013 C014 1.392(4) . ?
C013 H013 0.96(3) . ?
C014 C015 1.379(4) . ?
C014 H014 0.94(3) . ?
C015 C016 1.387(3) . ?
C015 H015 0.83(3) . ?
C016 C017 1.491(4) . ?
C017 H01A 0.91(3) . ?
C017 H01B 0.97(3) . ?
C017 H01C 1.00(4) . ?
N021 C022 1.343(3) . ?
N021 C026 1.353(3) . ?
N021 H021 0.86(3) . ?
C022 C023 1.376(3) . ?
C022 H022 0.95(3) . ?
C023 C024 1.384(4) . ?
C023 H023 0.93(3) . ?
C024 C025 1.381(4) . ?
C024 H024 0.98(3) . ?
C025 C026 1.388(3) . ?
C025 H025 0.98(3) . ?
C026 C027 1.489(4) . ?
C027 H02A 1.03(4) . ?
C027 H02B 1.03(3) . ?
C027 H02C 1.02(4) . ?

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
O11 C11 C12 127.2(2) . . ?
O11 C11 C16 121.57(19) . . ?
C12 C11 C16 111.16(18) . . ?
C13 C12 C11 124.2(2) . . ?
C13 C12 N12 115.77(19) . . ?
C11 C12 N12 120.00(18) . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 121.0(15) . . ?
C14 C13 H13 119.2(15) . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 N14 119.2(2) . . ?
C15 C14 N14 119.55(19) . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 H15 120.1(15) . . ?
C14 C15 H15 122.2(15) . . ?
C15 C16 C11 125.9(2) . . ?
C15 C16 N16 117.26(19) . . ?
C11 C16 N16 116.82(19) . . ?
O121 N12 O122 122.53(18) . . ?
O121 N12 C12 119.29(18) . . ?
O122 N12 C12 118.14(18) . . ?
O142 N14 O141 122.64(19) . . ?
O142 N14 C14 118.43(18) . . ?
O141 N14 C14 118.93(18) . . ?
O161 N16 O162 124.3(2) . . ?
O161 N16 C16 118.04(19) . . ?
O162 N16 C16 117.7(2) . . ?
O21 C21 C22 126.8(2) . . ?
O21 C21 C26 121.7(2) . . ?
C22 C21 C26 111.43(18) . . ?
C23 C22 C21 123.2(2) . . ?
C23 C22 N22 116.29(19) . . ?
C21 C22 N22 120.44(19) . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 122.3(16) . . ?
C24 C23 H23 117.3(16) . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 N24 119.4(2) . . ?
C25 C24 N24 119.47(19) . . ?
C26 C25 C24 117.9(2) . . ?
C26 C25 H25 119.6(14) . . ?
C24 C25 H25 122.5(14) . . ?
C25 C26 C21 125.8(2) . . ?
C25 C26 N26 117.20(19) . . ?
C21 C26 N26 116.88(18) . . ?
O221 N22 O222 121.0(2) . . ?
O221 N22 C22 120.33(19) . . ?
O222 N22 C22 118.69(18) . . ?
O241 N24 O242 122.59(19) . . ?
O241 N24 C24 118.77(18) . . ?
O242 N24 C24 118.64(19) . . ?
O261 N26 O262 124.2(2) . . ?
O261 N26 C26 118.72(19) . . ?
O262 N26 C26 117.12(19) . . ?
C016 N011 C012 123.2(2) . . ?
C016 N011 H011 121.9(18) . . ?
C012 N011 H011 114.9(17) . . ?
N011 C012 C013 120.1(2) . . ?
N011 C012 H012 111.9(16) . . ?
C013 C012 H012 128.0(16) . . ?
C012 C013 C014 118.7(2) . . ?
C012 C013 H013 117.5(16) . . ?
C014 C013 H013 123.8(16) . . ?
C015 C014 C013 119.9(2) . . ?
C015 C014 H014 117.8(15) . . ?
C013 C014 H014 122.3(15) . . ?
C014 C015 C016 120.3(2) . . ?
C014 C015 H015 117(2) . . ?
C016 C015 H015 123(2) . . ?
N011 C016 C015 117.8(2) . . ?
N011 C016 C017 117.7(2) . . ?
C015 C016 C017 124.5(2) . . ?
C016 C017 H01A 111.4(19) . . ?
C016 C017 H01B 112.5(16) . . ?
H01A C017 H01B 109(2) . . ?
C016 C017 H01C 111(2) . . ?
H01A C017 H01C 103(3) . . ?
H01B C017 H01C 110(3) . . ?
C022 N021 C026 123.4(2) . . ?
C022 N021 H021 122(2) . . ?
C026 N021 H021 115(2) . . ?
N021 C022 C023 120.2(2) . . ?
N021 C022 H022 114.5(17) . . ?
C023 C022 H022 125.3(17) . . ?
C022 C023 C024 118.4(3) . . ?
C022 C023 H023 117.3(17) . . ?
C024 C023 H023 124.3(17) . . ?
C025 C024 C023 120.2(2) . . ?
C025 C024 H024 121.1(16) . . ?
C023 C024 H024 118.7(16) . . ?
C024 C025 C026 120.4(2) . . ?
C024 C025 H025 121.9(17) . . ?
C026 C025 H025 117.7(17) . . ?
N021 C026 C025 117.4(2) . . ?
N021 C026 C027 117.4(2) . . ?
C025 C026 C027 125.3(2) . . ?
C026 C027 H02A 112.3(18) . . ?
C026 C027 H02B 112.8(18) . . ?
H02A C027 H02B 111(3) . . ?
C026 C027 H02C 112.9(19) . . ?
H02A C027 H02C 102(3) . . ?
H02B C027 H02C 105(3) . . ?

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
O11 C11 C12 C13 -174.1(2) . . . . ?
C16 C11 C12 C13 2.1(3) . . . . ?
O11 C11 C12 N12 5.2(3) . . . . ?
C16 C11 C12 N12 -178.66(19) . . . . ?
C11 C12 C13 C14 -3.0(3) . . . . ?
N12 C12 C13 C14 177.7(2) . . . . ?
C12 C13 C14 C15 2.4(3) . . . . ?
C12 C13 C14 N14 -178.9(2) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
N14 C14 C15 C16 -179.7(2) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C14 C15 C16 N16 177.9(2) . . . . ?
O11 C11 C16 C15 175.7(2) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
O11 C11 C16 N16 -2.0(3) . . . . ?
C12 C11 C16 N16 -178.38(18) . . . . ?
C13 C12 N12 O121 -157.3(2) . . . . ?
C11 C12 N12 O121 23.4(3) . . . . ?
C13 C12 N12 O122 20.6(3) . . . . ?
C11 C12 N12 O122 -158.74(19) . . . . ?
C13 C14 N14 O142 168.5(2) . . . . ?
C15 C14 N14 O142 -12.8(3) . . . . ?
C13 C14 N14 O141 -12.1(3) . . . . ?
C15 C14 N14 O141 166.6(2) . . . . ?
C15 C16 N16 O161 126.0(2) . . . . ?
C11 C16 N16 O161 -56.0(3) . . . . ?
C15 C16 N16 O162 -54.0(3) . . . . ?
C11 C16 N16 O162 123.9(2) . . . . ?
O21 C21 C22 C23 -177.5(2) . . . . ?
C26 C21 C22 C23 4.6(3) . . . . ?
O21 C21 C22 N22 5.0(3) . . . . ?
C26 C21 C22 N22 -172.83(19) . . . . ?
C21 C22 C23 C24 -2.4(3) . . . . ?
N22 C22 C23 C24 175.2(2) . . . . ?
C22 C23 C24 C25 -2.1(3) . . . . ?
C22 C23 C24 N24 -178.0(2) . . . . ?
C23 C24 C25 C26 3.6(3) . . . . ?
N24 C24 C25 C26 179.5(2) . . . . ?
C24 C25 C26 C21 -0.8(3) . . . . ?
C24 C25 C26 N26 -177.06(19) . . . . ?
O21 C21 C26 C25 179.0(2) . . . . ?
C22 C21 C26 C25 -3.0(3) . . . . ?
O21 C21 C26 N26 -4.8(3) . . . . ?
C22 C21 C26 N26 173.21(18) . . . . ?
C23 C22 N22 O221 169.8(2) . . . . ?
C21 C22 N22 O221 -12.6(3) . . . . ?
C23 C22 N22 O222 -10.1(3) . . . . ?
C21 C22 N22 O222 167.5(2) . . . . ?
C23 C24 N24 O241 -2.9(3) . . . . ?
C25 C24 N24 O241 -178.9(2) . . . . ?
C23 C24 N24 O242 176.3(2) . . . . ?
C25 C24 N24 O242 0.3(3) . . . . ?
C25 C26 N26 O261 -128.3(2) . . . . ?
C21 C26 N26 O261 55.2(3) . . . . ?
C25 C26 N26 O262 51.7(3) . . . . ?
C21 C26 N26 O262 -124.9(2) . . . . ?
C016 N011 C012 C013 0.8(3) . . . . ?
N011 C012 C013 C014 0.6(3) . . . . ?
C012 C013 C014 C015 -1.1(4) . . . . ?
C013 C014 C015 C016 0.2(4) . . . . ?
C012 N011 C016 C015 -1.7(3) . . . . ?
C012 N011 C016 C017 176.7(2) . . . . ?
C014 C015 C016 N011 1.2(3) . . . . ?
C014 C015 C016 C017 -177.1(2) . . . . ?
C026 N021 C022 C023 -0.9(4) . . . . ?
N021 C022 C023 C024 -0.2(4) . . . . ?
C022 C023 C024 C025 0.8(4) . . . . ?
C023 C024 C025 C026 -0.2(4) . . . . ?
C022 N021 C026 C025 1.5(3) . . . . ?
C022 N021 C026 C027 -177.2(2) . . . . ?
C024 C025 C026 N021 -0.9(3) . . . . ?
C024 C025 C026 C027 177.7(2) . . . . ?

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
N011 H011 O11 0.91(3) 1.81(3) 2.685(3) 160(3) .
N011 H011 O121 0.91(3) 2.26(3) 2.770(3) 115(2) .
N021 H021 O21 0.86(3) 1.84(3) 2.664(3) 160(3) .
N021 H021 O221 0.86(3) 2.25(3) 2.756(3) 118(2) .

_diffrn_measured_fraction_theta_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.077


_database_code_depnum_ccdc_archive 'CCDC 606103'
data_CCDC606104

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
8-Hydroxyquinolinium picrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C9 H8 N O'
_chemical_formula_sum            'C15 H10 N4 O8'
_chemical_formula_weight         374.27

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   P_21/c
_symmetry_int_tables_number      14
_symmetry_space_group_name_Hall  -P_2ybc

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                   8.259(2)
_cell_length_b                   9.243(2)
_cell_length_c                   19.849(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.282(4)
_cell_angle_gamma                90.00
_cell_volume                     1514.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    5095
_cell_measurement_theta_min      2.431
_cell_measurement_theta_max      27.9715

_exptl_crystal_description       shard
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      300(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13846
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         29.09
_reflns_number_total             3773
_reflns_number_gt                2782
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.0667P)²+0.4606P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3773
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
N01 N 0.42511(18) 0.06147(15) 0.36897(7) 0.0399(3) Uani 1 1 d . . .
H01 H 0.490(3) 0.047(2) 0.4029(11) 0.052(6) Uiso 1 1 d . . .
C02 C 0.3421(2) -0.0494(2) 0.34468(10) 0.0502(4) Uani 1 1 d . . .
H02 H 0.361(2) -0.137(2) 0.3661(10) 0.052(5) Uiso 1 1 d . . .
C03 C 0.2372(3) -0.0303(2) 0.28999(11) 0.0571(5) Uani 1 1 d . . .
H03 H 0.182(3) -0.110(3) 0.2733(11) 0.068(7) Uiso 1 1 d . . .
C04 C 0.2228(2) 0.1022(2) 0.26109(9) 0.0526(5) Uani 1 1 d . . .
H04 H 0.152(3) 0.115(3) 0.2226(12) 0.071(7) Uiso 1 1 d . . .
C05 C 0.2970(2) 0.3633(2) 0.26138(9) 0.0499(5) Uani 1 1 d . . .
H05 H 0.233(2) 0.379(2) 0.2237(10) 0.049(5) Uiso 1 1 d . . .
C06 C 0.3804(2) 0.4719(2) 0.29205(10) 0.0513(5) Uani 1 1 d . . .
H06 H 0.369(2) 0.567(3) 0.2739(11) 0.059(6) Uiso 1 1 d . . .
C07 C 0.4797(2) 0.4483(2) 0.34924(9) 0.0455(4) Uani 1 1 d . . .
H07 H 0.536(2) 0.525(2) 0.3702(10) 0.052(5) Uiso 1 1 d . . .
C08 C 0.4964(2) 0.31164(18) 0.37575(8) 0.0380(4) Uani 1 1 d . . .
C09 C 0.41196(19) 0.19788(17) 0.34361(8) 0.0355(3) Uani 1 1 d . . .
C010 C 0.3094(2) 0.2218(2) 0.28697(8) 0.0417(4) Uani 1 1 d . . .
O011 O 0.58379(16) 0.27428(14) 0.43070(6) 0.0480(3) Uani 1 1 d . . .
H011 H 0.622(3) 0.349(3) 0.4512(11) 0.064(7) Uiso 1 1 d . . .
O1 O 0.68997(18) 0.52160(14) 0.47480(7) 0.0598(4) Uani 1 1 d . . .
C1 C 0.78135(18) 0.59366(17) 0.51135(8) 0.0364(3) Uani 1 1 d . . .
C2 C 0.79485(19) 0.74933(17) 0.50481(8) 0.0366(3) Uani 1 1 d . . .
C3 C 0.8932(2) 0.83473(18) 0.54374(8) 0.0372(3) Uani 1 1 d . . .
H3 H 0.894(2) 0.933(2) 0.5367(9) 0.041(5) Uiso 1 1 d . . .
C4 C 0.98997(19) 0.77058(18) 0.59310(8) 0.0379(4) Uani 1 1 d . . .
C5 C 0.9833(2) 0.62384(19) 0.60476(8) 0.0385(4) Uani 1 1 d . . .
H5 H 1.045(2) 0.584(2) 0.6382(10) 0.046(5) Uiso 1 1 d . . .
C6 C 0.88235(19) 0.53890(17) 0.56611(8) 0.0363(3) Uani 1 1 d . . .
N2 N 0.68873(18) 0.82217(16) 0.45638(7) 0.0428(3) Uani 1 1 d . . .
O21 O 0.6529(2) 0.76408(15) 0.40337(7) 0.0634(4) Uani 1 1 d . . .
O22 O 0.64001(18) 0.94311(15) 0.47185(7) 0.0587(4) Uani 1 1 d . . .
N4 N 1.09371(18) 0.85996(18) 0.63503(7) 0.0469(4) Uani 1 1 d . . .
O41 O 1.1016(2) 0.98906(16) 0.62197(8) 0.0675(4) Uani 1 1 d . . .
O42 O 1.16737(19) 0.80401(17) 0.68257(7) 0.0656(4) Uani 1 1 d . . .
N6 N 0.87417(18) 0.38707(16) 0.58416(8) 0.0449(3) Uani 1 1 d . . .
O61 O 0.7997(2) 0.30405(16) 0.54875(9) 0.0793(5) Uani 1 1 d . . .
O62 O 0.9437(3) 0.34655(17) 0.63504(9) 0.0883(6) 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
N01 C02 1.318(2) . ?
N01 C09 1.361(2) . ?
N01 H01 0.86(2) . ?
C02 C03 1.385(3) . ?
C02 H02 0.93(2) . ?
C03 C04 1.356(3) . ?
C03 H03 0.92(2) . ?
C04 C010 1.408(3) . ?
C04 H04 0.96(2) . ?
C05 C06 1.354(3) . ?
C05 C010 1.406(3) . ?
C05 H05 0.92(2) . ?
C06 C07 1.402(3) . ?
C06 H06 0.95(2) . ?
C07 C08 1.374(2) . ?
C07 H07 0.94(2) . ?
C08 O011 1.340(2) . ?
C08 C09 1.407(2) . ?
C09 C010 1.410(2) . ?
O011 H011 0.86(3) . ?
O1 C1 1.231(2) . ?
C1 C6 1.447(2) . ?
C1 C2 1.449(2) . ?
C2 C3 1.361(2) . ?
C2 N2 1.452(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.91(2) . ?
C4 C5 1.377(2) . ?
C4 N4 1.441(2) . ?
C5 C6 1.368(2) . ?
C5 H5 0.906(19) . ?
C6 N6 1.450(2) . ?
N2 O21 1.2121(19) . ?
N2 O22 1.229(2) . ?
N4 O41 1.223(2) . ?
N4 O42 1.226(2) . ?
N6 O61 1.201(2) . ?
N6 O62 1.210(2) . ?

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
C02 N01 C09 123.24(15) . . ?
C02 N01 H01 118.7(14) . . ?
C09 N01 H01 118.1(14) . . ?
N01 C02 C03 119.93(19) . . ?
N01 C02 H02 115.4(13) . . ?
C03 C02 H02 124.6(13) . . ?
C04 C03 C02 119.61(19) . . ?
C04 C03 H03 121.8(15) . . ?
C02 C03 H03 118.5(15) . . ?
C03 C04 C010 121.04(17) . . ?
C03 C04 H04 119.4(15) . . ?
C010 C04 H04 119.5(15) . . ?
C06 C05 C010 119.64(16) . . ?
C06 C05 H05 121.7(13) . . ?
C010 C05 H05 118.6(13) . . ?
C05 C06 C07 122.09(18) . . ?
C05 C06 H06 117.9(13) . . ?
C07 C06 H06 120.0(13) . . ?
C08 C07 C06 120.32(18) . . ?
C08 C07 H07 118.7(13) . . ?
C06 C07 H07 120.9(13) . . ?
O011 C08 C07 126.61(16) . . ?
O011 C08 C09 115.42(14) . . ?
C07 C08 C09 117.96(15) . . ?
N01 C09 C08 119.34(14) . . ?
N01 C09 C010 118.81(15) . . ?
C08 C09 C010 121.82(15) . . ?
C05 C010 C04 124.51(16) . . ?
C05 C010 C09 118.14(16) . . ?
C04 C010 C09 117.33(17) . . ?
C08 O011 H011 111.2(16) . . ?
O1 C1 C6 126.10(15) . . ?
O1 C1 C2 122.13(15) . . ?
C6 C1 C2 111.74(14) . . ?
C3 C2 C1 124.83(15) . . ?
C3 C2 N2 116.79(15) . . ?
C1 C2 N2 118.25(14) . . ?
C2 C3 C4 118.78(15) . . ?
C2 C3 H3 119.4(11) . . ?
C4 C3 H3 121.9(11) . . ?
C5 C4 C3 121.07(15) . . ?
C5 C4 N4 119.54(15) . . ?
C3 C4 N4 119.32(15) . . ?
C6 C5 C4 119.82(15) . . ?
C6 C5 H5 120.5(13) . . ?
C4 C5 H5 119.7(13) . . ?
C5 C6 C1 123.67(15) . . ?
C5 C6 N6 116.62(14) . . ?
C1 C6 N6 119.66(14) . . ?
O21 N2 O22 123.00(15) . . ?
O21 N2 C2 120.09(15) . . ?
O22 N2 C2 116.90(14) . . ?
O41 N4 O42 123.15(16) . . ?
O41 N4 C4 118.08(15) . . ?
O42 N4 C4 118.76(16) . . ?
O61 N6 O62 121.21(16) . . ?
O61 N6 C6 119.99(14) . . ?
O62 N6 C6 118.80(15) . . ?

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
C09 N01 C02 C03 1.1(3) . . . . ?
N01 C02 C03 C04 1.1(3) . . . . ?
C02 C03 C04 C010 -1.8(3) . . . . ?
C010 C05 C06 C07 -0.2(3) . . . . ?
C05 C06 C07 C08 0.6(3) . . . . ?
C06 C07 C08 O011 -178.41(17) . . . . ?
C06 C07 C08 C09 0.3(3) . . . . ?
C02 N01 C09 C08 175.44(16) . . . . ?
C02 N01 C09 C010 -2.5(3) . . . . ?
O011 C08 C09 N01 -0.7(2) . . . . ?
C07 C08 C09 N01 -179.53(16) . . . . ?
O011 C08 C09 C010 177.19(15) . . . . ?
C07 C08 C09 C010 -1.7(2) . . . . ?
C06 C05 C010 C04 177.00(18) . . . . ?
C06 C05 C010 C09 -1.1(3) . . . . ?
C03 C04 C010 C05 -177.73(19) . . . . ?
C03 C04 C010 C09 0.4(3) . . . . ?
N01 C09 C010 C05 179.96(15) . . . . ?
C08 C09 C010 C05 2.1(2) . . . . ?
N01 C09 C010 C04 1.7(2) . . . . ?
C08 C09 C010 C04 -176.19(16) . . . . ?
O1 C1 C2 C3 179.83(17) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
O1 C1 C2 N2 4.1(2) . . . . ?
C6 C1 C2 N2 -174.02(13) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
N2 C2 C3 C4 176.52(14) . . . . ?
C2 C3 C4 C5 -2.5(2) . . . . ?
C2 C3 C4 N4 -179.51(14) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
N4 C4 C5 C6 178.54(15) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 N6 -176.17(15) . . . . ?
O1 C1 C6 C5 179.25(17) . . . . ?
C2 C1 C6 C5 -2.7(2) . . . . ?
O1 C1 C6 N6 -3.4(3) . . . . ?
C2 C1 C6 N6 174.65(14) . . . . ?
C3 C2 N2 O21 148.00(17) . . . . ?
C1 C2 N2 O21 -35.9(2) . . . . ?
C3 C2 N2 O22 -31.5(2) . . . . ?
C1 C2 N2 O22 144.55(16) . . . . ?
C5 C4 N4 O41 177.41(17) . . . . ?
C3 C4 N4 O41 -5.5(2) . . . . ?
C5 C4 N4 O42 -3.8(2) . . . . ?
C3 C4 N4 O42 173.25(16) . . . . ?
C5 C6 N6 O61 -173.19(18) . . . . ?
C1 C6 N6 O61 9.3(3) . . . . ?
C5 C6 N6 O62 6.6(3) . . . . ?
C1 C6 N6 O62 -170.92(18) . . . . ?

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
N01 H01 O22 0.86(2) 2.06(2) 2.891(2) 161(2) 1_545
O011 H011 O1 0.86(3) 1.75(3) 2.5936(19) 167(2) .
O011 H011 O61 0.86(3) 2.44(2) 2.926(2) 116.5(19) .

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.074

_database_code_depnum_ccdc_archive 'CCDC 606104'
data_CCDC606105

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Bis(2-pyridyl)ammonium picrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C10 H10 N3'
_chemical_formula_sum            'C16 H12 N6 O7'
_chemical_formula_weight         400.32

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   P_21/c
_symmetry_int_tables_number      14
_symmetry_space_group_name_Hall  -P_2ybc

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                   9.1996(11)
_cell_length_b                   14.6492(18)
_cell_length_c                   13.1834(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.918(2)
_cell_angle_gamma                90.00
_cell_volume                     1680.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6733
_cell_measurement_theta_min      2.3405
_cell_measurement_theta_max      33.0235

_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22442
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         33.16
_reflns_number_total             6132
_reflns_number_gt                4482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'

_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)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6132
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1684
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_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
N01 N 0.58816(14) 0.13864(9) 0.14053(9) 0.0248(2) Uani 1 1 d . . .
H01 H 0.582(2) 0.1252(15) 0.2053(18) 0.038(5) Uiso 1 1 d . . .
N011 N 0.76357(14) 0.17477(9) 0.05223(10) 0.0272(3) Uani 1 1 d . . .
C012 C 0.90532(19) 0.20231(12) 0.05664(15) 0.0350(3) Uani 1 1 d . . .
H012 H 0.922(2) 0.2104(14) -0.0125(16) 0.030(5) Uiso 1 1 d . . .
C013 C 1.0207(2) 0.22048(13) 0.15131(16) 0.0389(4) Uani 1 1 d . . .
H013 H 1.120(3) 0.2404(18) 0.1513(19) 0.049(6) Uiso 1 1 d . . .
C014 C 0.9894(2) 0.20917(12) 0.24711(15) 0.0374(4) Uani 1 1 d . . .
H014 H 1.069(3) 0.2220(18) 0.317(2) 0.051(7) Uiso 1 1 d . . .
C015 C 0.84549(18) 0.18104(11) 0.24524(12) 0.0305(3) Uani 1 1 d . . .
H015 H 0.816(2) 0.1752(15) 0.3092(17) 0.037(5) Uiso 1 1 d . . .
C016 C 0.73543(15) 0.16511(9) 0.14481(11) 0.0234(3) Uani 1 1 d . . .
N021 N 0.48500(14) 0.11526(8) -0.04544(9) 0.0229(2) Uani 1 1 d . . .
H021 H 0.584(3) 0.1326(16) -0.0402(17) 0.041(6) Uiso 1 1 d . . .
C022 C 0.36823(17) 0.09278(10) -0.13533(11) 0.0262(3) Uani 1 1 d . . .
H022 H 0.396(2) 0.0953(14) -0.1987(15) 0.028(5) Uiso 1 1 d . . .
C023 C 0.22809(18) 0.06815(11) -0.12915(12) 0.0294(3) Uani 1 1 d . . .
H023 H 0.143(2) 0.0526(16) -0.1947(17) 0.039(5) Uiso 1 1 d . . .
C024 C 0.20772(17) 0.06637(11) -0.02822(13) 0.0302(3) Uani 1 1 d . . .
H024 H 0.109(2) 0.0484(15) -0.0219(17) 0.038(5) Uiso 1 1 d . . .
C025 C 0.32621(17) 0.08943(11) 0.06223(12) 0.0271(3) Uani 1 1 d . . .
H025 H 0.316(2) 0.0877(14) 0.1350(16) 0.029(5) Uiso 1 1 d . . .
C026 C 0.46847(15) 0.11494(9) 0.05284(10) 0.0215(2) Uani 1 1 d . . .
O1 O 0.60211(14) 0.04081(8) 0.32199(8) 0.0307(2) Uani 1 1 d . . .
C1 C 0.63532(15) 0.05221(9) 0.42064(10) 0.0212(2) Uani 1 1 d . . .
C2 C 0.55747(15) 0.11634(9) 0.46970(10) 0.0210(2) Uani 1 1 d . . .
C3 C 0.58839(15) 0.12667(9) 0.57829(11) 0.0220(2) Uani 1 1 d . . .
H3 H 0.533(2) 0.1686(13) 0.6013(14) 0.022(4) Uiso 1 1 d . . .
C4 C 0.70759(15) 0.07665(10) 0.64778(10) 0.0223(2) Uani 1 1 d . . .
C5 C 0.79107(15) 0.01441(10) 0.60964(11) 0.0237(3) Uani 1 1 d . . .
H5 H 0.871(2) -0.0247(15) 0.6564(16) 0.035(5) Uiso 1 1 d . . .
C6 C 0.75379(15) 0.00137(9) 0.50098(10) 0.0228(2) Uani 1 1 d . . .
N2 N 0.43374(15) 0.17250(8) 0.40130(10) 0.0265(2) Uani 1 1 d . . .
O21 O 0.43380(18) 0.19237(9) 0.31076(10) 0.0430(3) Uani 1 1 d . . .
O22 O 0.33413(13) 0.19931(8) 0.43835(10) 0.0328(2) Uani 1 1 d . . .
N4 N 0.74235(14) 0.08808(9) 0.76213(9) 0.0267(2) Uani 1 1 d . . .
O41 O 0.66083(14) 0.13995(9) 0.79406(9) 0.0365(3) Uani 1 1 d . . .
O42 O 0.85250(13) 0.04547(10) 0.82253(9) 0.0363(3) Uani 1 1 d . . .
N6 N 0.83883(17) -0.07000(11) 0.46777(10) 0.0357(3) Uani 1 1 d . . .
O61 O 0.7801(3) -0.10519(16) 0.38025(12) 0.0893(8) Uani 1 1 d . . .
O62 O 0.96144(14) -0.09595(9) 0.53132(10) 0.0365(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
N01 C026 1.3579(17) . ?
N01 C016 1.3927(18) . ?
N01 H01 0.90(2) . ?
N011 C016 1.3348(18) . ?
N011 C012 1.348(2) . ?
C012 C013 1.377(3) . ?
C012 H012 0.98(2) . ?
C013 C014 1.393(3) . ?
C013 H013 0.96(2) . ?
C014 C015 1.379(2) . ?
C014 H014 0.99(3) . ?
C015 C016 1.401(2) . ?
C015 H015 0.97(2) . ?
N021 C026 1.3526(17) . ?
N021 C022 1.3569(18) . ?
N021 H021 0.92(2) . ?
C022 C023 1.366(2) . ?
C022 H022 0.950(19) . ?
C023 C024 1.403(2) . ?
C023 H023 0.98(2) . ?
C024 C025 1.372(2) . ?
C024 H024 0.97(2) . ?
C025 C026 1.405(2) . ?
C025 H025 0.994(19) . ?
O1 C1 1.2470(16) . ?
C1 C2 1.4540(19) . ?
C1 C6 1.4546(18) . ?
C2 C3 1.3744(18) . ?
C2 N2 1.4560(18) . ?
C3 C4 1.3883(19) . ?
C3 H3 0.913(19) . ?
C4 C5 1.387(2) . ?
C4 N4 1.4457(17) . ?
C5 C6 1.3739(18) . ?
C5 H5 0.98(2) . ?
C6 N6 1.4556(19) . ?
N2 O21 1.2287(17) . ?
N2 O22 1.2341(17) . ?
N4 O41 1.2335(18) . ?
N4 O42 1.2358(17) . ?
N6 O61 1.218(2) . ?
N6 O62 1.2272(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
C026 N01 C016 127.98(12) . . ?
C026 N01 H01 118.1(14) . . ?
C016 N01 H01 112.5(14) . . ?
C016 N011 C012 117.64(13) . . ?
N011 C012 C013 123.19(16) . . ?
N011 C012 H012 115.8(12) . . ?
C013 C012 H012 121.0(12) . . ?
C012 C013 C014 118.28(15) . . ?
C012 C013 H013 120.9(15) . . ?
C014 C013 H013 120.9(15) . . ?
C015 C014 C013 119.89(15) . . ?
C015 C014 H014 119.3(14) . . ?
C013 C014 H014 120.8(14) . . ?
C014 C015 C016 117.53(15) . . ?
C014 C015 H015 123.2(13) . . ?
C016 C015 H015 119.2(13) . . ?
N011 C016 N01 117.84(12) . . ?
N011 C016 C015 123.46(14) . . ?
N01 C016 C015 118.69(13) . . ?
C026 N021 C022 122.19(12) . . ?
C026 N021 H021 110.0(14) . . ?
C022 N021 H021 127.8(14) . . ?
N021 C022 C023 120.48(13) . . ?
N021 C022 H022 113.4(12) . . ?
C023 C022 H022 126.1(12) . . ?
C022 C023 C024 118.69(14) . . ?
C022 C023 H023 120.1(13) . . ?
C024 C023 H023 121.2(13) . . ?
C025 C024 C023 120.47(14) . . ?
C025 C024 H024 119.5(12) . . ?
C023 C024 H024 120.0(12) . . ?
C024 C025 C026 119.31(13) . . ?
C024 C025 H025 122.4(11) . . ?
C026 C025 H025 118.3(11) . . ?
N021 C026 N01 120.17(12) . . ?
N021 C026 C025 118.86(12) . . ?
N01 C026 C025 120.97(12) . . ?
O1 C1 C2 124.13(12) . . ?
O1 C1 C6 124.28(12) . . ?
C2 C1 C6 111.57(11) . . ?
C3 C2 C1 124.68(12) . . ?
C3 C2 N2 116.05(12) . . ?
C1 C2 N2 119.23(11) . . ?
C2 C3 C4 118.80(12) . . ?
C2 C3 H3 118.1(11) . . ?
C4 C3 H3 123.0(11) . . ?
C5 C4 C3 121.29(12) . . ?
C5 C4 N4 119.52(12) . . ?
C3 C4 N4 119.17(12) . . ?
C6 C5 C4 119.27(13) . . ?
C6 C5 H5 117.2(12) . . ?
C4 C5 H5 123.4(12) . . ?
C5 C6 C1 124.25(12) . . ?
C5 C6 N6 115.89(12) . . ?
C1 C6 N6 119.84(12) . . ?
O21 N2 O22 122.91(13) . . ?
O21 N2 C2 119.28(13) . . ?
O22 N2 C2 117.80(12) . . ?
O41 N4 O42 123.61(12) . . ?
O41 N4 C4 118.27(12) . . ?
O42 N4 C4 118.12(13) . . ?
O61 N6 O62 122.85(15) . . ?
O61 N6 C6 118.18(14) . . ?
O62 N6 C6 118.81(13) . . ?

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
C016 N011 C012 C013 0.1(3) . . . . ?
N011 C012 C013 C014 0.5(3) . . . . ?
C012 C013 C014 C015 -0.4(3) . . . . ?
C013 C014 C015 C016 -0.1(3) . . . . ?
C012 N011 C016 N01 178.59(14) . . . . ?
C012 N011 C016 C015 -0.8(2) . . . . ?
C026 N01 C016 N011 4.8(2) . . . . ?
C026 N01 C016 C015 -175.83(14) . . . . ?
C014 C015 C016 N011 0.8(2) . . . . ?
C014 C015 C016 N01 -178.57(14) . . . . ?
C026 N021 C022 C023 -0.4(2) . . . . ?
N021 C022 C023 C024 -0.2(2) . . . . ?
C022 C023 C024 C025 0.3(2) . . . . ?
C023 C024 C025 C026 0.0(2) . . . . ?
C022 N021 C026 N01 -179.46(13) . . . . ?
C022 N021 C026 C025 0.8(2) . . . . ?
C016 N01 C026 N021 0.0(2) . . . . ?
C016 N01 C026 C025 179.81(14) . . . . ?
C024 C025 C026 N021 -0.6(2) . . . . ?
C024 C025 C026 N01 179.67(14) . . . . ?
O1 C1 C2 C3 176.99(14) . . . . ?
C6 C1 C2 C3 -1.48(19) . . . . ?
O1 C1 C2 N2 -0.8(2) . . . . ?
C6 C1 C2 N2 -179.25(12) . . . . ?
C1 C2 C3 C4 3.7(2) . . . . ?
N2 C2 C3 C4 -178.44(12) . . . . ?
C2 C3 C4 C5 -2.6(2) . . . . ?
C2 C3 C4 N4 179.11(12) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
N4 C4 C5 C6 177.60(12) . . . . ?
C4 C5 C6 C1 3.1(2) . . . . ?
C4 C5 C6 N6 -175.45(13) . . . . ?
O1 C1 C6 C5 179.52(14) . . . . ?
C2 C1 C6 C5 -2.02(19) . . . . ?
O1 C1 C6 N6 -2.0(2) . . . . ?
C2 C1 C6 N6 176.50(13) . . . . ?
C3 C2 N2 O21 154.24(14) . . . . ?
C1 C2 N2 O21 -27.80(19) . . . . ?
C3 C2 N2 O22 -24.60(18) . . . . ?
C1 C2 N2 O22 153.36(13) . . . . ?
C5 C4 N4 O41 -175.92(13) . . . . ?
C3 C4 N4 O41 2.4(2) . . . . ?
C5 C4 N4 O42 4.3(2) . . . . ?
C3 C4 N4 O42 -177.36(13) . . . . ?
C5 C6 N6 O61 155.9(2) . . . . ?
C1 C6 N6 O61 -22.7(3) . . . . ?
C5 C6 N6 O62 -19.6(2) . . . . ?
C1 C6 N6 O62 161.75(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
N01 H01 O1 0.90(2) 1.94(2) 2.7557(16) 152(2) .
N01 H01 O21 0.90(2) 2.45(2) 3.1207(18) 132.2(18) .
N021 H021 N011 0.92(2) 1.82(2) 2.6165(17) 144(2) .
N021 H021 O41 0.92(2) 2.51(2) 3.0732(17) 119.7(17) 1_554

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.077

_database_code_depnum_ccdc_archive 'CCDC 606105'
