# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_160701b
_database_code_depnum_ccdc_archive 'CCDC 1497227'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H14 N16 Na2 O6'
_chemical_formula_weight         476.33

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.7660(6)
_cell_length_b                   7.2849(7)
_cell_length_c                   10.7541(9)
_cell_angle_alpha                109.069(2)
_cell_angle_beta                 98.9320(10)
_cell_angle_gamma                103.404(2)
_cell_volume                     471.70(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    711
_cell_measurement_theta_min      3.012
_cell_measurement_theta_max      28.255

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1631
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1631
_reflns_number_gt                1156
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0991P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1631
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1811
_refine_ls_wR_factor_gt          0.1680
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Na1 Na -0.0471(3) 0.3003(2) 0.06024(16) 0.0401(5) Uani 1 1 d . . .
N1 N 0.2575(6) 0.5871(5) 0.5027(4) 0.0400(10) Uani 1 1 d . . .
H1A H 0.2638 0.7137 0.5307 0.048 Uiso 1 1 calc R . .
H1B H 0.2888 0.5332 0.5604 0.048 Uiso 1 1 calc R . .
N2 N 0.1369(6) 0.1410(5) 0.1957(3) 0.0357(10) Uani 1 1 d . . .
N3 N 0.1301(6) -0.0467(5) 0.1798(3) 0.0372(10) Uani 1 1 d . . .
N4 N 0.1800(7) -0.0519(5) 0.3040(3) 0.0330(9) Uani 1 1 d . . .
H4 H 0.1875 -0.1593 0.3191 0.040 Uiso 1 1 calc R . .
N5 N 0.3155(7) 0.3394(5) 0.6483(3) 0.0432(11) Uani 1 1 d . . .
N6 N 0.3598(7) 0.2943(6) 0.7590(3) 0.0410(10) Uani 1 1 d . . .
N7 N 0.3398(7) 0.1004(5) 0.7225(3) 0.0390(10) Uani 1 1 d . . .
N8 N 0.2862(7) 0.0132(5) 0.5863(3) 0.0389(9) Uani 1 1 d . . .
O1 O 0.1532(5) 0.5450(4) 0.2847(3) 0.0409(9) Uani 1 1 d . . .
O2 O 0.2372(5) 0.4929(5) 0.0047(3) 0.0413(8) Uani 1 1 d . . .
H2A H 0.2760 0.4200 -0.0606 0.050 Uiso 1 1 d R . .
H2B H 0.3416 0.5619 0.0729 0.050 Uiso 1 1 d R . .
O3 O -0.3412(7) 0.1607(7) 0.1280(4) 0.0813(14) Uani 1 1 d . . .
H3B H -0.3063 0.1053 0.1828 0.098 Uiso 1 1 d R . .
H3C H -0.4736 0.1165 0.0960 0.098 Uiso 1 1 d R . .
C1 C 0.2006(7) 0.4772(6) 0.3734(4) 0.0321(10) Uani 1 1 d . . .
C2 C 0.1877(7) 0.2569(6) 0.3309(4) 0.0293(10) Uani 1 1 d . . .
C3 C 0.2168(7) 0.1327(6) 0.4024(4) 0.0300(10) Uani 1 1 d . . .
C4 C 0.2726(7) 0.1636(6) 0.5452(4) 0.0296(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Na1 0.0501(12) 0.0340(10) 0.0352(10) 0.0163(8) 0.0058(9) 0.0092(9)
N1 0.063(3) 0.0216(19) 0.033(2) 0.0109(17) 0.0052(19) 0.0135(19)
N2 0.046(3) 0.027(2) 0.032(2) 0.0117(16) 0.0036(17) 0.0107(17)
N3 0.055(3) 0.0259(19) 0.0270(19) 0.0082(15) 0.0045(18) 0.0111(19)
N4 0.045(2) 0.0216(17) 0.0309(19) 0.0110(15) 0.0024(18) 0.0094(18)
N5 0.069(3) 0.030(2) 0.0266(19) 0.0111(17) 0.0065(19) 0.012(2)
N6 0.060(3) 0.035(2) 0.0270(19) 0.0127(16) 0.0109(19) 0.011(2)
N7 0.050(3) 0.034(2) 0.034(2) 0.0160(17) 0.010(2) 0.010(2)
N8 0.054(3) 0.0261(19) 0.033(2) 0.0105(16) 0.0066(19) 0.010(2)
O1 0.058(2) 0.0253(16) 0.0376(17) 0.0154(14) 0.0037(15) 0.0107(15)
O2 0.041(2) 0.0446(18) 0.0322(15) 0.0096(14) 0.0052(17) 0.0112(18)
O3 0.060(3) 0.108(3) 0.107(3) 0.085(3) 0.021(3) 0.018(3)
C1 0.032(3) 0.028(2) 0.037(3) 0.016(2) 0.007(2) 0.007(2)
C2 0.031(2) 0.022(2) 0.034(2) 0.0123(19) 0.0034(18) 0.0086(19)
C3 0.028(2) 0.026(2) 0.032(2) 0.0102(18) 0.0018(18) 0.0047(19)
C4 0.033(3) 0.024(2) 0.030(2) 0.0118(18) 0.0067(19) 0.0050(19)

_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
Na1 O3 2.350(5) . ?
Na1 O2 2.383(4) . ?
Na1 O2 2.392(3) 2_565 ?
Na1 O1 2.427(3) . ?
Na1 N2 2.496(4) . ?
Na1 N3 2.519(4) 2 ?
Na1 Na1 3.523(3) 2_565 ?
N1 C1 1.299(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 N3 1.310(5) . ?
N2 C2 1.361(5) . ?
N3 N4 1.341(4) . ?
N3 Na1 2.519(4) 2 ?
N4 C3 1.350(5) . ?
N4 H4 0.8600 . ?
N5 C4 1.324(5) . ?
N5 N6 1.344(5) . ?
N6 N7 1.304(5) . ?
N7 N8 1.342(5) . ?
N8 C4 1.325(5) . ?
O1 C1 1.243(5) . ?
O2 Na1 2.392(3) 2_565 ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
O3 H3B 0.8500 . ?
O3 H3C 0.8501 . ?
C1 C2 1.495(6) . ?
C2 C3 1.393(5) . ?
C3 C4 1.451(5) . ?

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
O3 Na1 O2 170.56(15) . . ?
O3 Na1 O2 87.44(14) . 2_565 ?
O2 Na1 O2 84.89(12) . 2_565 ?
O3 Na1 O1 96.44(14) . . ?
O2 Na1 O1 79.26(12) . . ?
O2 Na1 O1 98.29(12) 2_565 . ?
O3 Na1 N2 84.22(13) . . ?
O2 Na1 N2 101.70(13) . . ?
O2 Na1 N2 162.85(13) 2_565 . ?
O1 Na1 N2 67.92(11) . . ?
O3 Na1 N3 99.94(16) . 2 ?
O2 Na1 N3 86.01(12) . 2 ?
O2 Na1 N3 93.23(12) 2_565 2 ?
O1 Na1 N3 160.36(15) . 2 ?
N2 Na1 N3 102.95(13) . 2 ?
O3 Na1 Na1 129.56(14) . 2_565 ?
O2 Na1 Na1 42.54(8) . 2_565 ?
O2 Na1 Na1 42.35(8) 2_565 2_565 ?
O1 Na1 Na1 88.38(10) . 2_565 ?
N2 Na1 Na1 141.79(13) . 2_565 ?
N3 Na1 Na1 89.49(10) 2 2_565 ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N3 N2 C2 109.1(3) . . ?
N3 N2 Na1 134.5(3) . . ?
C2 N2 Na1 110.8(3) . . ?
N2 N3 N4 107.5(3) . . ?
N2 N3 Na1 117.1(2) . 2 ?
N4 N3 Na1 135.3(3) . 2 ?
N3 N4 C3 111.5(3) . . ?
N3 N4 H4 124.3 . . ?
C3 N4 H4 124.3 . . ?
C4 N5 N6 104.1(3) . . ?
N7 N6 N5 109.8(3) . . ?
N6 N7 N8 109.1(3) . . ?
C4 N8 N7 104.7(3) . . ?
C1 O1 Na1 117.5(3) . . ?
Na1 O2 Na1 95.11(12) . 2_565 ?
Na1 O2 H2A 112.7 . . ?
Na1 O2 H2A 112.7 2_565 . ?
Na1 O2 H2B 112.6 . . ?
Na1 O2 H2B 112.7 2_565 . ?
H2A O2 H2B 110.3 . . ?
Na1 O3 H3B 110.1 . . ?
Na1 O3 H3C 136.9 . . ?
H3B O3 H3C 109.3 . . ?
O1 C1 N1 123.4(4) . . ?
O1 C1 C2 119.0(4) . . ?
N1 C1 C2 117.6(4) . . ?
N2 C2 C3 108.1(3) . . ?
N2 C2 C1 118.5(3) . . ?
C3 C2 C1 133.4(4) . . ?
N4 C3 C2 103.8(3) . . ?
N4 C3 C4 121.3(4) . . ?
C2 C3 C4 134.9(4) . . ?
N5 C4 N8 112.3(4) . . ?
N5 C4 C3 125.5(4) . . ?
N8 C4 C3 122.3(4) . . ?

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
O3 Na1 N2 N3 70.8(4) . . . . ?
O2 Na1 N2 N3 -116.7(4) . . . . ?
O2 Na1 N2 N3 132.1(5) 2_565 . . . ?
O1 Na1 N2 N3 170.1(4) . . . . ?
N3 Na1 N2 N3 -28.1(5) 2 . . . ?
Na1 Na1 N2 N3 -134.2(4) 2_565 . . . ?
O3 Na1 N2 C2 -79.0(3) . . . . ?
O2 Na1 N2 C2 93.5(3) . . . . ?
O2 Na1 N2 C2 -17.8(7) 2_565 . . . ?
O1 Na1 N2 C2 20.3(3) . . . . ?
N3 Na1 N2 C2 -177.9(3) 2 . . . ?
Na1 Na1 N2 C2 76.0(4) 2_565 . . . ?
C2 N2 N3 N4 -1.1(5) . . . . ?
Na1 N2 N3 N4 -151.3(3) . . . . ?
C2 N2 N3 Na1 -178.8(3) . . . 2 ?
Na1 N2 N3 Na1 31.1(5) . . . 2 ?
N2 N3 N4 C3 0.9(5) . . . . ?
Na1 N3 N4 C3 178.0(3) 2 . . . ?
C4 N5 N6 N7 -1.2(5) . . . . ?
N5 N6 N7 N8 1.4(6) . . . . ?
N6 N7 N8 C4 -0.9(5) . . . . ?
O3 Na1 O1 C1 60.9(3) . . . . ?
O2 Na1 O1 C1 -127.6(3) . . . . ?
O2 Na1 O1 C1 149.2(3) 2_565 . . . ?
N2 Na1 O1 C1 -20.2(3) . . . . ?
N3 Na1 O1 C1 -85.5(5) 2 . . . ?
Na1 Na1 O1 C1 -169.5(3) 2_565 . . . ?
O3 Na1 O2 Na1 -35.8(9) . . . 2_565 ?
O2 Na1 O2 Na1 0.0 2_565 . . 2_565 ?
O1 Na1 O2 Na1 -99.45(12) . . . 2_565 ?
N2 Na1 O2 Na1 -163.98(13) . . . 2_565 ?
N3 Na1 O2 Na1 93.60(12) 2 . . 2_565 ?
Na1 O1 C1 N1 -161.6(4) . . . . ?
Na1 O1 C1 C2 17.0(5) . . . . ?
N3 N2 C2 C3 0.9(5) . . . . ?
Na1 N2 C2 C3 158.6(3) . . . . ?
N3 N2 C2 C1 -178.8(4) . . . . ?
Na1 N2 C2 C1 -21.2(5) . . . . ?
O1 C1 C2 N2 4.0(7) . . . . ?
N1 C1 C2 N2 -177.3(4) . . . . ?
O1 C1 C2 C3 -175.7(5) . . . . ?
N1 C1 C2 C3 3.0(8) . . . . ?
N3 N4 C3 C2 -0.4(5) . . . . ?
N3 N4 C3 C4 179.7(4) . . . . ?
N2 C2 C3 N4 -0.3(5) . . . . ?
C1 C2 C3 N4 179.4(5) . . . . ?
N2 C2 C3 C4 179.6(5) . . . . ?
C1 C2 C3 C4 -0.7(9) . . . . ?
N6 N5 C4 N8 0.6(6) . . . . ?
N6 N5 C4 C3 -179.3(4) . . . . ?
N7 N8 C4 N5 0.2(6) . . . . ?
N7 N8 C4 C3 -179.9(4) . . . . ?
N4 C3 C4 N5 178.6(5) . . . . ?
C2 C3 C4 N5 -1.3(8) . . . . ?
N4 C3 C4 N8 -1.4(7) . . . . ?
C2 C3 C4 N8 178.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.089
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_151017g
_database_code_depnum_ccdc_archive 'CCDC 1497228'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H5 N5 O2'
_chemical_formula_weight         155.13

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   P2(1)/c

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                   3.6672(3)
_cell_length_b                   16.3613(14)
_cell_length_c                   11.3345(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.7600(10)
_cell_angle_gamma                90.00
_cell_volume                     673.84(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    851
_cell_measurement_theta_min      3.081
_cell_measurement_theta_max      25.493

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3230
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1183
_reflns_number_gt                745
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0694P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1183
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.0520(8) 0.23741(15) 0.80851(19) 0.0386(8) Uani 1 1 d . . .
N2 N 1.1207(8) 0.21185(15) 0.7032(2) 0.0386(8) Uani 1 1 d . . .
H2 H 1.2138 0.1645 0.6934 0.046 Uiso 1 1 calc R . .
N3 N 1.0375(8) 0.26347(14) 0.6138(2) 0.0360(7) Uani 1 1 d . . .
N4 N 0.7788(8) 0.40037(15) 0.48037(19) 0.0435(8) Uani 1 1 d . . .
H4A H 0.6936 0.4406 0.4362 0.052 Uiso 1 1 calc R . .
H4B H 0.8783 0.3594 0.4494 0.052 Uiso 1 1 calc R . .
N5 N 0.7130(9) 0.40359(17) 0.9495(2) 0.0551(9) Uani 1 1 d . . .
O1 O 0.6201(7) 0.45726(12) 0.64753(17) 0.0452(7) Uani 1 1 d . . .
O2 O 0.5046(7) 0.57408(13) 0.81396(18) 0.0517(8) Uani 1 1 d . . .
H2C H 0.5222 0.5287 0.7786 0.062 Uiso 1 1 d R . .
H2D H 0.4369 0.5651 0.8816 0.062 Uiso 1 1 d R . .
C1 C 0.7572(9) 0.40147(17) 0.5955(2) 0.0330(8) Uani 1 1 d . . .
C2 C 0.9017(9) 0.32797(17) 0.6638(2) 0.0304(8) Uani 1 1 d . . .
C3 C 0.9112(9) 0.31194(17) 0.7850(2) 0.0321(8) Uani 1 1 d . . .
C4 C 0.8011(10) 0.36245(19) 0.8773(3) 0.0370(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.056(2) 0.0309(15) 0.0310(14) -0.0015(11) 0.0133(13) 0.0007(13)
N2 0.059(2) 0.0251(13) 0.0344(14) -0.0002(11) 0.0147(13) 0.0034(13)
N3 0.053(2) 0.0250(14) 0.0305(13) 0.0030(11) 0.0083(12) 0.0000(13)
N4 0.073(2) 0.0327(15) 0.0252(13) 0.0041(11) 0.0087(13) 0.0110(15)
N5 0.084(3) 0.0487(19) 0.0367(15) -0.0029(14) 0.0212(16) 0.0121(18)
O1 0.0718(19) 0.0325(12) 0.0324(11) -0.0035(10) 0.0106(11) 0.0155(12)
O2 0.092(2) 0.0273(12) 0.0400(13) -0.0048(9) 0.0248(13) -0.0074(12)
C1 0.047(2) 0.0238(16) 0.0289(15) -0.0007(13) 0.0058(14) 0.0000(16)
C2 0.040(2) 0.0247(16) 0.0275(14) -0.0029(12) 0.0060(13) -0.0016(14)
C3 0.044(2) 0.0243(16) 0.0296(14) 0.0003(12) 0.0099(14) -0.0003(15)
C4 0.048(2) 0.0317(17) 0.0325(16) 0.0053(14) 0.0098(15) 0.0046(16)

_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 N2 1.320(3) . ?
N1 C3 1.337(4) . ?
N2 N3 1.323(3) . ?
N2 H2 0.8600 . ?
N3 C2 1.326(4) . ?
N4 C1 1.318(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 C4 1.139(4) . ?
O1 C1 1.230(3) . ?
O2 H2C 0.8499 . ?
O2 H2D 0.8500 . ?
C1 C2 1.489(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.434(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
N2 N1 C3 103.0(2) . . ?
N1 N2 N3 116.0(2) . . ?
N1 N2 H2 122.0 . . ?
N3 N2 H2 122.0 . . ?
N2 N3 C2 104.0(2) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
H2C O2 H2D 108.9 . . ?
O1 C1 N4 124.6(3) . . ?
O1 C1 C2 119.3(3) . . ?
N4 C1 C2 116.0(3) . . ?
N3 C2 C3 108.1(2) . . ?
N3 C2 C1 123.3(2) . . ?
C3 C2 C1 128.6(3) . . ?
N1 C3 C2 109.0(2) . . ?
N1 C3 C4 121.3(2) . . ?
C2 C3 C4 129.7(3) . . ?
N5 C4 C3 178.9(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
C3 N1 N2 N3 0.2(4) . . . . ?
N1 N2 N3 C2 -0.3(4) . . . . ?
N2 N3 C2 C3 0.3(3) . . . . ?
N2 N3 C2 C1 -177.8(3) . . . . ?
O1 C1 C2 N3 176.7(3) . . . . ?
N4 C1 C2 N3 -1.6(5) . . . . ?
O1 C1 C2 C3 -1.0(5) . . . . ?
N4 C1 C2 C3 -179.3(3) . . . . ?
N2 N1 C3 C2 0.0(3) . . . . ?
N2 N1 C3 C4 -179.3(3) . . . . ?
N3 C2 C3 N1 -0.2(4) . . . . ?
C1 C2 C3 N1 177.8(3) . . . . ?
N3 C2 C3 C4 179.0(3) . . . . ?
C1 C2 C3 C4 -3.0(6) . . . . ?
N1 C3 C4 N5 170(21) . . . . ?
C2 C3 C4 N5 -9(22) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.059
