# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ss-45-lt
_database_code_depnum_ccdc_archive 'CCDC 798914'
_audit_update_record             
;
2014-03-13 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 1-Propyl-3-methylimidazoliumpicrate
;
_chemical_name_common            pmimpic
_chemical_melting_point          444K
_chemical_formula_moiety         'C6 H2 N3 O7, C7 H13 N2'
_chemical_formula_sum            'C13 H15 N5 O7'
_chemical_formula_weight         353.30

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'
_space_group_name_Hall           '-P 1'

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

_cell_length_a                   6.6831(7)
_cell_length_b                   10.6065(10)
_cell_length_c                   11.8839(9)
_cell_angle_alpha                73.513(7)
_cell_angle_beta                 87.771(7)
_cell_angle_gamma                75.787(8)
_cell_volume                     782.59(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368.0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293
_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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6059
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.1153
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         29.12
_reflns_number_total             4212
_reflns_number_gt                1837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0310P)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    Riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3521
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1449
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.0989
_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
N1 N 0.3501(4) 0.6948(2) 1.13594(19) 0.0276(6) Uani 1 1 d . . .
N2 N 0.2909(4) 0.5500(2) 1.29372(19) 0.0228(6) Uani 1 1 d . . .
C1 C 0.2579(5) 0.5031(3) 1.2017(3) 0.0311(8) Uani 1 1 d . . .
H1 H 0.2176 0.4238 1.2065 0.037 Uiso 1 1 calc R . .
C2 C 0.3458(5) 0.6661(3) 1.2520(2) 0.0260(7) Uani 1 1 d . . .
H2 H 0.3762 0.7185 1.2967 0.031 Uiso 1 1 calc R . .
C3 C 0.2949(5) 0.5935(3) 1.1027(3) 0.0330(8) Uani 1 1 d . . .
H3 H 0.2849 0.5884 1.0263 0.040 Uiso 1 1 calc R . .
C4 C 0.2623(5) 0.4851(3) 1.4184(2) 0.0300(8) Uani 1 1 d . . .
H4A H 0.1347 0.4576 1.4265 0.045 Uiso 1 1 calc R . .
H4B H 0.2586 0.5484 1.4628 0.045 Uiso 1 1 calc R . .
H4C H 0.3749 0.4071 1.4473 0.045 Uiso 1 1 calc R . .
C5 C 0.3878(6) 0.8209(3) 1.0564(3) 0.0420(10) Uani 1 1 d . . .
H5A H 0.4424 0.8686 1.1018 0.050 Uiso 1 1 calc R . .
H5B H 0.2579 0.8790 1.0193 0.050 Uiso 1 1 calc R . .
C6 C 0.5384(5) 0.7936(3) 0.9623(2) 0.0348(8) Uani 1 1 d . . .
H6A H 0.4838 0.7448 0.9180 0.042 Uiso 1 1 calc R . .
H6B H 0.5481 0.8797 0.9085 0.042 Uiso 1 1 calc R . .
C7 C 0.7536(5) 0.7128(3) 1.0093(3) 0.0423(9) Uani 1 1 d . . .
H7A H 0.8408 0.7014 0.9449 0.063 Uiso 1 1 calc R . .
H7B H 0.7468 0.6254 1.0595 0.063 Uiso 1 1 calc R . .
H7C H 0.8095 0.7603 1.0531 0.063 Uiso 1 1 calc R . .
O1 O 0.1631(4) 0.6064(2) 0.65083(18) 0.0469(7) Uani 1 1 d . . .
O2 O 0.2124(4) 0.6412(2) 0.81544(17) 0.0457(7) Uani 1 1 d . . .
O3 O 0.0796(4) 1.0959(2) 0.83076(18) 0.0439(7) Uani 1 1 d . . .
O4 O 0.1373(4) 1.2549(2) 0.68051(19) 0.0431(6) Uani 1 1 d . . .
O5 O 0.3062(3) 1.1675(2) 0.31792(17) 0.0358(6) Uani 1 1 d . . .
O6 O 0.3269(3) 0.9733(2) 0.28797(17) 0.0374(6) Uani 1 1 d . . .
O7 O 0.3317(3) 0.7613(2) 0.47132(16) 0.0316(5) Uani 1 1 d . . .
N3 N 0.1972(4) 0.6789(2) 0.7074(2) 0.0259(6) Uani 1 1 d . . .
N4 N 0.1270(4) 1.1373(3) 0.7272(2) 0.0319(7) Uani 1 1 d . . .
N5 N 0.3014(4) 1.0469(3) 0.3532(2) 0.0236(6) Uani 1 1 d . . .
C8 C 0.2731(4) 0.8473(3) 0.5251(2) 0.0204(7) Uani 1 1 d . . .
C9 C 0.2125(4) 0.8163(3) 0.6479(2) 0.0186(6) Uani 1 1 d . . .
C10 C 0.1683(4) 0.9072(3) 0.7118(2) 0.0216(7) Uani 1 1 d . . .
H10A H 0.1354 0.8799 0.7904 0.026 Uiso 1 1 calc R . .
C11 C 0.1730(4) 1.0407(3) 0.6589(2) 0.0218(7) Uani 1 1 d . . .
C12 C 0.2169(4) 1.0835(3) 0.5417(2) 0.0215(7) Uani 1 1 d . . .
H12 H 0.2151 1.1741 0.5065 0.026 Uiso 1 1 calc R . .
C13 C 0.2631(4) 0.9917(3) 0.4773(2) 0.0182(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
N1 C2 1.327(3) . ?
N1 C3 1.376(4) . ?
N1 C5 1.475(3) . ?
N2 C2 1.326(3) . ?
N2 C1 1.369(3) . ?
N2 C4 1.473(3) . ?
C1 C3 1.349(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.517(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.517(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1 N3 1.219(3) . ?
O2 N3 1.232(3) . ?
O3 N4 1.240(3) . ?
O4 N4 1.231(3) . ?
O5 N5 1.236(3) . ?
O6 N5 1.228(3) . ?
O7 C8 1.237(3) . ?
N3 C9 1.455(3) . ?
N4 C11 1.449(3) . ?
N5 C13 1.462(3) . ?
C8 C13 1.460(4) . ?
C8 C9 1.465(4) . ?
C9 C10 1.361(4) . ?
C10 C11 1.385(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.381(4) . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 108.5(2) . . ?
C2 N1 C5 125.2(3) . . ?
C3 N1 C5 126.1(2) . . ?
C2 N2 C1 108.9(2) . . ?
C2 N2 C4 125.4(2) . . ?
C1 N2 C4 125.7(3) . . ?
C3 C1 N2 107.0(3) . . ?
C3 C1 H1 126.5 . . ?
N2 C1 H1 126.5 . . ?
N2 C2 N1 108.6(3) . . ?
N2 C2 H2 125.7 . . ?
N1 C2 H2 125.7 . . ?
C1 C3 N1 107.1(3) . . ?
C1 C3 H3 126.5 . . ?
N1 C3 H3 126.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 112.1(2) . . ?
N1 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 114.2(3) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 N3 O2 121.9(3) . . ?
O1 N3 C9 120.1(2) . . ?
O2 N3 C9 118.0(2) . . ?
O4 N4 O3 123.4(3) . . ?
O4 N4 C11 118.9(2) . . ?
O3 N4 C11 117.6(3) . . ?
O6 N5 O5 122.4(2) . . ?
O6 N5 C13 119.6(2) . . ?
O5 N5 C13 118.0(2) . . ?
O7 C8 C13 125.0(3) . . ?
O7 C8 C9 124.1(3) . . ?
C13 C8 C9 110.8(2) . . ?
C10 C9 N3 116.6(2) . . ?
C10 C9 C8 124.8(3) . . ?
N3 C9 C8 118.6(2) . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 N4 119.7(3) . . ?
C10 C11 N4 119.3(2) . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 124.1(2) . . ?
C12 C13 N5 115.9(2) . . ?
C8 C13 N5 120.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.837
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SS-41
_database_code_depnum_ccdc_archive 'CCDC 991638'
_audit_update_record             
;
2014-03-13 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        1-methyl-3-butylimidazoliumpicrate
_chemical_name_common            mmimpic
_chemical_melting_point          '420.5 K'
_chemical_formula_moiety         'C6 H2 N3 O7, C5 H9 N2'
_chemical_formula_sum            'C11 H11 N5 O7'
_chemical_formula_weight         325.25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           ' -P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3233(7)
_cell_length_b                   9.6646(9)
_cell_length_c                   10.3323(12)
_cell_angle_alpha                78.588(9)
_cell_angle_beta                 80.835(9)
_cell_angle_gamma                85.796(8)
_cell_volume                     707.02(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      293(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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5270
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         29.17
_reflns_number_total             3169
_reflns_number_gt                1938
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement. R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.0637P)²+0.2061P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    Riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.060(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3169
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3628(2) 0.63742(16) 0.46334(18) 0.0470(5) Uani 1 1 d . . .
C1 C 0.2622(3) 0.5452(2) 0.5326(2) 0.0336(5) Uani 1 1 d . . .
C2 C 0.2281(3) 0.4128(2) 0.4954(2) 0.0331(5) Uani 1 1 d . . .
C3 C 0.1182(3) 0.3111(2) 0.5759(2) 0.0373(6) Uani 1 1 d . . .
H3 H 0.1004 0.2288 0.5464 0.045 Uiso 1 1 calc R . .
C4 C 0.0345(3) 0.3311(2) 0.7000(2) 0.0390(6) Uani 1 1 d . . .
C5 C 0.0581(3) 0.4524(3) 0.7456(3) 0.0417(6) Uani 1 1 d . . .
H5 H 0.0027 0.4640 0.8305 0.050 Uiso 1 1 calc R . .
C6 C 0.1638(3) 0.5551(2) 0.6649(2) 0.0381(6) Uani 1 1 d . . .
N1 N 0.3104(3) 0.3828(2) 0.3662(2) 0.0425(5) Uani 1 1 d . . .
O2 O 0.3860(3) 0.4756(2) 0.28127(19) 0.0647(6) Uani 1 1 d . . .
O3 O 0.2991(3) 0.2650(2) 0.3447(2) 0.0803(8) Uani 1 1 d . . .
N2 N -0.0827(3) 0.2244(3) 0.7834(2) 0.0543(6) Uani 1 1 d . . .
O4 O -0.0997(3) 0.1165(2) 0.7420(2) 0.0743(7) Uani 1 1 d . . .
O5 O -0.1610(3) 0.2472(2) 0.8917(2) 0.0792(7) Uani 1 1 d . . .
N3 N 0.1769(4) 0.6834(3) 0.7165(3) 0.0617(7) Uani 1 1 d . . .
O6 O 0.1921(5) 0.7944(3) 0.6385(3) 0.1124(11) Uani 1 1 d . . .
O7 O 0.1645(5) 0.6756(3) 0.8347(3) 0.1219(12) Uani 1 1 d . . .
C7 C 0.4444(3) 0.2159(2) 0.8072(3) 0.0399(6) Uani 1 1 d . . .
H7 H 0.5141 0.2868 0.7514 0.048 Uiso 1 1 calc R . .
N4 N 0.4117(3) 0.09469(19) 0.7767(2) 0.0434(6) Uani 1 1 d . . .
C8 C 0.3050(4) 0.0186(3) 0.8844(3) 0.0584(8) Uani 1 1 d . . .
H8 H 0.2617 -0.0708 0.8901 0.070 Uiso 1 1 calc R . .
C9 C 0.2747(4) 0.0961(3) 0.9791(3) 0.0607(8) Uani 1 1 d . . .
H9 H 0.2066 0.0709 1.0635 0.073 Uiso 1 1 calc R . .
N5 N 0.3626(3) 0.2204(2) 0.9292(2) 0.0457(6) Uani 1 1 d . . .
C10 C 0.4811(5) 0.0501(3) 0.6501(3) 0.0633(9) Uani 1 1 d . . .
H10A H 0.5299 0.1295 0.5858 0.095 Uiso 1 1 calc R . .
H10B H 0.3818 0.0136 0.6183 0.095 Uiso 1 1 calc R . .
H10C H 0.5772 -0.0221 0.6632 0.095 Uiso 1 1 calc R . .
C11 C 0.3705(5) 0.3364(3) 1.0001(3) 0.0738(10) Uani 1 1 d . . .
H11A H 0.4666 0.3151 1.0552 0.111 Uiso 1 1 calc R . .
H11B H 0.2538 0.3479 1.0551 0.111 Uiso 1 1 calc R . .
H11C H 0.3964 0.4221 0.9366 0.111 Uiso 1 1 calc R . .


_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 1.235(2) . ?
C1 C2 1.456(3) . ?
C1 C6 1.458(3) . ?
C2 C3 1.374(3) . ?
C2 N1 1.449(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 N2 1.444(3) . ?
C5 C6 1.364(3) . ?
C5 H5 0.9300 . ?
C6 N3 1.457(3) . ?
N1 O3 1.213(3) . ?
N1 O2 1.220(2) . ?
N2 O4 1.225(3) . ?
N2 O5 1.226(3) . ?
N3 O7 1.199(4) . ?
N3 O6 1.208(3) . ?
C7 N5 1.314(3) . ?
C7 N4 1.319(3) . ?
C7 H7 0.9300 . ?
N4 C8 1.368(3) . ?
N4 C10 1.460(4) . ?
C8 C9 1.329(4) . ?
C8 H8 0.9300 . ?
C9 N5 1.373(3) . ?
C9 H9 0.9300 . ?
N5 C11 1.465(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 125.2(2) . . ?
O1 C1 C6 123.6(2) . . ?
C2 C1 C6 111.17(19) . . ?
C3 C2 N1 116.0(2) . . ?
C3 C2 C1 123.8(2) . . ?
N1 C2 C1 120.16(19) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 N2 119.6(2) . . ?
C5 C4 N2 119.3(2) . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 N3 116.6(2) . . ?
C5 C6 C1 124.7(2) . . ?
N3 C6 C1 118.6(2) . . ?
O3 N1 O2 121.5(2) . . ?
O3 N1 C2 118.5(2) . . ?
O2 N1 C2 120.0(2) . . ?
O4 N2 O5 123.4(2) . . ?
O4 N2 C4 118.3(2) . . ?
O5 N2 C4 118.2(2) . . ?
O7 N3 O6 122.5(3) . . ?
O7 N3 C6 118.9(3) . . ?
O6 N3 C6 118.6(3) . . ?
N5 C7 N4 109.1(2) . . ?
N5 C7 H7 125.5 . . ?
N4 C7 H7 125.5 . . ?
C7 N4 C8 108.2(2) . . ?
C7 N4 C10 125.3(2) . . ?
C8 N4 C10 126.5(2) . . ?
C9 C8 N4 107.3(2) . . ?
C9 C8 H8 126.3 . . ?
N4 C8 H8 126.3 . . ?
C8 C9 N5 107.3(3) . . ?
C8 C9 H9 126.3 . . ?
N5 C9 H9 126.3 . . ?
C7 N5 C9 108.1(2) . . ?
C7 N5 C11 125.4(2) . . ?
C9 N5 C11 126.4(3) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.832
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.048
