# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_platon_sq
_database_code_depnum_ccdc_archive 'CCDC 1909579'
loop_
_audit_author_name
_audit_author_address
'K. Suenkel'
;Ludwig Maximilians University Munich
Germany
;
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT049_platon_sq           
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9286 Check
RESPONSE: The compound is an organic light-atom molecule with large voids
;
_vrf_PLAT601_platon_sq           
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        129 Ang**3
RESPONSE: the squeeze routine was used together with "swat"
;
# Added during the CSD deposition process: Thursday 11 April 2019 02:11 PM
# end Validation Reply Form


_audit_creation_date             2019-04-10T13:48:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H2 N5'
_chemical_formula_weight         180.16

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_Int_Tables_number      11
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   3.9752(3)
_cell_length_b                   26.0148(19)
_cell_length_c                   6.2820(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.357(3)
_cell_angle_gamma                90
_cell_volume                     644.30(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2397
_cell_measurement_theta_min      3.1322
_cell_measurement_theta_max      25.2464

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    0.929
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             182

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.7953
_exptl_absorpt_correction_T_max  0.862

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'rotating anode generator'
_diffrn_source_type              'Bruker TXS'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector_area_resol_mean 7.391
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_number            6744
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             1213
_reflns_number_gt                1011
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0675P)²+0.3790P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1213
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2319
_refine_ls_wR_factor_gt          0.2233
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.027

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.7100(13) 0.25 0.2935(8) 0.0269(12) Uani 1 2 d S T P . .
C2 C 0.6188(10) 0.29354(15) 0.4047(6) 0.0306(10) Uani 1 1 d . . . . .
C3 C 0.4705(9) 0.27688(16) 0.5901(6) 0.0295(10) Uani 1 1 d . . . . .
C4 C 0.6846(10) 0.34458(15) 0.3553(6) 0.0324(11) Uani 1 1 d . . . . .
C5 C 0.3451(10) 0.30964(15) 0.7403(6) 0.0304(10) Uani 1 1 d . . . . .
N1 N 0.8569(13) 0.25 0.1074(8) 0.0327(12) Uani 1 2 d S T P . .
N2 N 0.7437(12) 0.38720(15) 0.3138(7) 0.0506(12) Uani 1 1 d . . . . .
N3 N 0.2433(10) 0.33713(14) 0.8605(6) 0.0383(10) Uani 1 1 d . . . . .
H1 H 0.941(13) 0.283(2) 0.069(8) 0.054(15) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.021(3) 0.033(3) 0.025(3) 0 -0.005(2) 0
C2 0.032(2) 0.033(2) 0.0260(19) 0.0007(16) 0.0007(16) -0.0004(17)
C3 0.0229(19) 0.040(2) 0.0245(18) -0.0021(16) -0.0017(14) -0.0018(16)
C4 0.037(2) 0.028(2) 0.031(2) -0.0027(16) -0.0011(16) 0.0002(17)
C5 0.028(2) 0.032(2) 0.030(2) 0.0000(17) -0.0006(16) -0.0024(16)
N1 0.033(3) 0.034(3) 0.032(3) 0 0.007(2) 0
N2 0.069(3) 0.034(2) 0.047(2) 0.0029(18) -0.002(2) -0.007(2)
N3 0.042(2) 0.036(2) 0.038(2) -0.0035(16) 0.0080(16) 0.0017(16)


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.372(7) . ?
C1 C2 1.403(5) 4_565 ?
C1 C2 1.403(5) . ?
C2 C4 1.396(6) . ?
C2 C3 1.438(5) . ?
C3 C3 1.398(8) 4_565 ?
C3 C5 1.409(6) . ?
C4 N2 1.170(6) . ?
C5 N3 1.151(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
N1 C1 C2 126.1(2) . 4_565 ?
N1 C1 C2 126.1(2) . . ?
C2 C1 C2 107.7(5) 4_565 . ?
C4 C2 C1 126.1(4) . . ?
C4 C2 C3 125.1(4) . . ?
C1 C2 C3 108.6(4) . . ?
C3 C3 C5 127.2(2) 4_565 . ?
C3 C3 C2 107.5(2) 4_565 . ?
C5 C3 C2 125.2(4) . . ?
N2 C4 C2 179.2(5) . . ?
N3 C5 C3 178.8(4) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_platon_sq_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1909580'
loop_
_audit_author_name
_audit_author_address
'K. Suenkel'
;Ludwig Maximilians University Munich
Germany
;
_audit_update_record             
;
2019-11-14 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;

_audit_creation_date             2019-04-10T12:52:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H6 N6'
_chemical_formula_weight         198.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7736(3)
_cell_length_b                   8.6454(4)
_cell_length_c                   10.2350(4)
_cell_angle_alpha                67.6660(10)
_cell_angle_beta                 72.808(2)
_cell_angle_gamma                83.739(2)
_cell_volume                     529.63(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3302
_cell_measurement_theta_min      2.547
_cell_measurement_theta_max      26.3678

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             204

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  0.9705

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'rotating anode generator'
_diffrn_source_type              'Bruker TXS'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_number            6157
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.706
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             2136
_reflns_number_gt                1751
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.5666P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2136
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.054

#--------------------------------------#
# Refinement special information       #
#--------------------------------------#
#In the original refinement three small, however significant electron density
#maxima could be localized near the TCC-NH2 nitrogen atom, two of which were
# at the typical N-H bond distances, while the third one showed an elongated
# distance. As it was directed towards the "external" (ammonium) nitrogen atom
# it seemed plausible to us that this would be part of a N-H-N hydrogen bridge,
# similar to the O-H-O bridges observed in the well-known diacetyldioxime
# complexes of nickel and cobalt. As in these compounds, the hydrogen atom
# is perhaps "delocalized" between the two nitrogen atoms. Anyway, free 
# refinement of these three electron density maxima as hydrogen was possible
# without problems. However, the remaining three hydrogen atoms of the assumed
# NH4 cation could not be localized. As the PLATON analysis of the structure
# showed large voids, it was decided to refine with the SQUEEZE routine.
# While the R-values improved, the positions of the assumed hydrogen atoms
# were not identifiable. Therefore, a "riding model" calculation, assuming
# a methyl group instead of NH3 and replacing just for this positioning H10 
# by a carbon atom gave now three positions, which were then fixed in the 
# refinement allowing only a common temperature factor to refine. Free
# refinement, even if using restraints and constraints for N-H and H-H
# distances and angles, was not possible. Because of this procedure the
# strange H-H distances involving these calculated H-atoms resulted.
#

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
N0 N 0.5498(3) 0.3080(2) 0.10562(19) 0.0242(4) Uani 1 1 d . . . . .
N1 N 0.8234(3) 0.2008(2) 0.2541(2) 0.0222(4) Uani 1 1 d . . . . .
N5 N 0.7744(3) -0.0554(2) 0.6722(2) 0.0289(5) Uani 1 1 d . . . . .
N2 N 0.8382(3) 0.6703(2) 0.0145(2) 0.0323(5) Uani 1 1 d . . . . .
N3 N 0.7552(3) 0.8393(2) 0.3816(2) 0.0307(5) Uani 1 1 d . . . . .
N4 N 0.7043(3) 0.3846(3) 0.7908(2) 0.0359(5) Uani 1 1 d . . . . .
C1 C 0.8004(3) 0.3042(3) 0.3403(2) 0.0197(5) Uani 1 1 d . . . . .
C2 C 0.7953(3) 0.4789(3) 0.2838(2) 0.0191(4) Uani 1 1 d . . . . .
C4 C 0.7590(3) 0.3913(3) 0.5295(2) 0.0202(5) Uani 1 1 d . . . . .
C9 C 0.7754(3) 0.0798(3) 0.5907(2) 0.0218(5) Uani 1 1 d . . . . .
C5 C 0.7785(3) 0.2487(3) 0.4905(2) 0.0198(5) Uani 1 1 d . . . . .
C6 C 0.8186(3) 0.5847(3) 0.1345(2) 0.0224(5) Uani 1 1 d . . . . .
C7 C 0.7607(3) 0.7024(3) 0.3916(2) 0.0236(5) Uani 1 1 d . . . . .
C3 C 0.7699(3) 0.5329(3) 0.4021(2) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.7293(3) 0.3892(3) 0.6737(2) 0.0247(5) Uani 1 1 d . . . . .
H0A H 0.437025 0.243951 0.145788 0.131(11) Uiso 1 1 d . U . . .
H0B H 0.594323 0.326662 0.010077 0.131(11) Uiso 1 1 d . U . . .
H0C H 0.520926 0.404316 0.119127 0.131(11) Uiso 1 1 d . U . . .
H10 H 0.716(3) 0.220(3) 0.177(2) 0.015(5) Uiso 1 1 d . . . . .
H1 H 0.798(5) 0.082(4) 0.313(3) 0.052(9) Uiso 1 1 d . . . . .
H2 H 0.961(6) 0.220(4) 0.182(4) 0.062(10) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N0 0.0207(9) 0.0341(11) 0.0162(9) -0.0052(8) -0.0068(7) -0.0033(8)
N1 0.0286(10) 0.0177(9) 0.0202(9) -0.0063(8) -0.0067(8) -0.0018(8)
N5 0.0332(11) 0.0238(10) 0.0232(10) -0.0020(8) -0.0072(8) 0.0003(8)
N2 0.0349(12) 0.0293(11) 0.0246(11) -0.0029(9) -0.0068(9) 0.0028(9)
N3 0.0345(11) 0.0233(11) 0.0366(12) -0.0129(9) -0.0101(9) -0.0007(8)
N4 0.0314(11) 0.0520(14) 0.0278(11) -0.0194(10) -0.0077(9) 0.0025(10)
C1 0.0188(10) 0.0194(10) 0.0198(10) -0.0059(8) -0.0050(8) -0.0018(8)
C2 0.0172(10) 0.0185(10) 0.0202(10) -0.0044(8) -0.0061(8) -0.0011(8)
C4 0.0164(10) 0.0232(11) 0.0206(10) -0.0079(9) -0.0046(8) -0.0001(8)
C9 0.0212(11) 0.0230(11) 0.0198(11) -0.0074(9) -0.0041(8) 0.0000(8)
C5 0.0189(10) 0.0190(10) 0.0199(10) -0.0050(8) -0.0062(8) 0.0005(8)
C6 0.0230(11) 0.0191(11) 0.0241(12) -0.0072(9) -0.0061(9) 0.0002(8)
C7 0.0199(11) 0.0264(12) 0.0258(12) -0.0099(9) -0.0073(9) -0.0007(9)
C3 0.0155(10) 0.0199(10) 0.0241(11) -0.0085(9) -0.0055(8) -0.0003(8)
C8 0.0189(11) 0.0299(12) 0.0270(12) -0.0120(10) -0.0072(9) 0.0014(9)


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N0 H0A 0.8906(18) . ?
N0 H0B 0.8886(17) . ?
N0 H0C 0.8870(19) . ?
N0 H10 1.50(2) . ?
N1 C1 1.445(3) . ?
N1 H10 1.18(2) . ?
N1 H1 0.98(3) . ?
N1 H2 0.99(4) . ?
N5 C9 1.149(3) . ?
N2 C6 1.144(3) . ?
N3 C7 1.145(3) . ?
N4 C8 1.146(3) . ?
C1 C5 1.392(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.416(3) . ?
C2 C6 1.423(3) . ?
C4 C3 1.398(3) . ?
C4 C5 1.416(3) . ?
C4 C8 1.422(3) . ?
C9 C5 1.428(3) . ?
C7 C3 1.424(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
H0A N0 H0B 109.55(19) . . ?
H0A N0 H0C 109.69(19) . . ?
H0B N0 H0C 109.87(19) . . ?
H0A N0 H10 109.3(8) . . ?
H0B N0 H10 109.1(8) . . ?
H0C N0 H10 109.3(8) . . ?
C1 N1 H10 120.8(10) . . ?
C1 N1 H1 113.8(18) . . ?
H10 N1 H1 99(2) . . ?
C1 N1 H2 109.6(19) . . ?
H10 N1 H2 101(2) . . ?
H1 N1 H2 111(3) . . ?
C5 C1 C2 109.00(19) . . ?
C5 C1 N1 126.50(19) . . ?
C2 C1 N1 124.50(19) . . ?
C1 C2 C3 107.39(18) . . ?
C1 C2 C6 126.87(19) . . ?
C3 C2 C6 125.70(19) . . ?
C3 C4 C5 107.86(18) . . ?
C3 C4 C8 126.5(2) . . ?
C5 C4 C8 125.66(19) . . ?
N5 C9 C5 179.1(2) . . ?
C1 C5 C4 107.69(18) . . ?
C1 C5 C9 127.5(2) . . ?
C4 C5 C9 124.79(19) . . ?
N2 C6 C2 179.6(2) . . ?
N3 C7 C3 179.2(3) . . ?
C4 C3 C2 108.06(18) . . ?
C4 C3 C7 126.34(19) . . ?
C2 C3 C7 125.59(19) . . ?
N4 C8 C4 178.7(3) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
