# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_Et2NH2DNT
_database_code_depnum_ccdc_archive 'CCDC 1006181'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Et2NH2DNT
_chemical_formula_moiety         'C2 N5 O4, C4 H12 N'
_chemical_formula_sum            'C6 H12 N6 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         232.22

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   6.4659(4)
_cell_length_b                   8.9964(6)
_cell_length_c                   18.8357(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.5420(10)
_cell_angle_gamma                90
_cell_volume                     1080.51(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24237
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      29.13
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.499
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.162
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488

_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  0.746

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            24237
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             2903
_reflns_number_gt                2518
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0842
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         2903
_refine_ls_number_parameters     153
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.2954P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.19931(14) 0.65943(10) 0.41238(5) 0.01626(18) Uani d . . . 1 . .
N N1 0.24316(12) 0.54448(8) 0.45680(4) 0.01731(16) Uani d . . . 1 . .
O O1 0.25774(14) 0.52846(9) 0.31310(4) 0.03106(19) Uani d . . . 1 . .
C C2 0.21905(13) 0.61371(10) 0.51739(5) 0.01596(17) Uani d . . . 1 . .
N N2 0.15157(12) 0.78805(9) 0.44110(4) 0.01712(16) Uani d . . . 1 . .
O O2 0.14070(13) 0.75549(9) 0.29801(4) 0.03017(18) Uani d . . . 1 . .
C C3 0.15829(16) 0.14918(12) 0.35719(6) 0.0272(2) Uani d . . . 1 . .
H H3A 0.111 0.2477 0.3374 0.033 Uiso calc U . R 1 . .
H H3B 0.2242 0.0962 0.3206 0.033 Uiso calc U . R 1 . .
N N3 0.16548(12) 0.75706(9) 0.51241(4) 0.01724(16) Uani d . . . 1 . .
O O3 0.28330(12) 0.40435(8) 0.58728(4) 0.02662(17) Uani d . . . 1 . .
C C4 0.31718(17) 0.16944(13) 0.42490(7) 0.0359(3) Uani d . . . 1 . .
H H4A 0.2552 0.2287 0.4596 0.054 Uiso calc U . R 1 . .
H H4B 0.4409 0.2208 0.4132 0.054 Uiso calc U . R 1 . .
H H4C 0.3585 0.072 0.4458 0.054 Uiso calc U . R 1 . .
N N4 0.19974(13) 0.64661(9) 0.33560(4) 0.02061(17) Uani d . . . 1 . .
O O4 0.23233(13) 0.61343(9) 0.63962(4) 0.02976(18) Uani d . . . 1 . .
C C5 -0.18965(17) 0.03608(11) 0.30799(5) 0.0237(2) Uani d . . . 1 . .
H H5A -0.122 0 0.2678 0.028 Uiso calc U . R 1 . .
H H5B -0.2621 0.1307 0.2929 0.028 Uiso calc U . R 1 . .
N N5 0.24791(13) 0.53792(9) 0.58637(4) 0.01948(17) Uani d . . . 1 . .
C C6 -0.34751(17) -0.07712(12) 0.32433(6) 0.0294(2) Uani d . . . 1 . .
H H6A -0.2777 -0.1731 0.3352 0.044 Uiso calc U . R 1 . .
H H6B -0.4588 -0.0878 0.2825 0.044 Uiso calc U . R 1 . .
H H6C -0.4086 -0.044 0.3659 0.044 Uiso calc U . R 1 . .
N N6 -0.02612(12) 0.06248(9) 0.37277(4) 0.01627(16) Uani d . . D 1 . .
H H2N -0.0847(18) 0.1109(13) 0.4062(6) 0.02 Uiso d U . D 1 . .
H H1N 0.0185(18) -0.0261(12) 0.3916(6) 0.02 Uiso d U . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3308(12) ?
C1 N2 . 1.3349(12) ?
C1 N4 . 1.4513(11) ?
N1 C2 . 1.3319(12) ?
O1 N4 . 1.2259(11) ?
C2 N3 . 1.3346(12) ?
C2 N5 . 1.4516(11) ?
N2 N3 . 1.3602(11) ?
O2 N4 . 1.2317(11) ?
C3 N6 . 1.4941(12) ?
C3 C4 . 1.5103(16) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
O3 N5 . 1.2228(11) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
O4 N5 . 1.2294(11) ?
C5 N6 . 1.4952(12) ?
C5 C6 . 1.5092(15) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
N6 H2N . 0.900(11) ?
N6 H1N . 0.900(11) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 117.28(8) ?
N1 C1 N4 . . 121.96(8) ?
N2 C1 N4 . . 120.76(8) ?
C1 N1 C2 . . 97.60(7) ?
N1 C2 N3 . . 117.22(8) ?
N1 C2 N5 . . 122.09(8) ?
N3 C2 N5 . . 120.68(8) ?
C1 N2 N3 . . 103.92(7) ?
N6 C3 C4 . . 110.51(9) ?
N6 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
N6 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C2 N3 N2 . . 103.97(7) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
O1 N4 O2 . . 125.04(8) ?
O1 N4 C1 . . 117.69(8) ?
O2 N4 C1 . . 117.27(8) ?
N6 C5 C6 . . 110.58(8) ?
N6 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
N6 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
O3 N5 O4 . . 124.89(8) ?
O3 N5 C2 . . 118.05(8) ?
O4 N5 C2 . . 117.06(8) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C3 N6 C5 . . 113.71(8) ?
C3 N6 H2N . . 109.1(8) ?
C5 N6 H2N . . 109.0(8) ?
C3 N6 H1N . . 109.0(8) ?
C5 N6 H1N . . 108.6(8) ?
H2N N6 H1N . . 107.2(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C1 N1 C2 . . . . -0.22(10) ?
N4 C1 N1 C2 . . . . -179.34(8) ?
C1 N1 C2 N3 . . . . 0.07(10) ?
C1 N1 C2 N5 . . . . 179.68(8) ?
N1 C1 N2 N3 . . . . 0.29(11) ?
N4 C1 N2 N3 . . . . 179.42(8) ?
N1 C2 N3 N2 . . . . 0.09(10) ?
N5 C2 N3 N2 . . . . -179.53(8) ?
C1 N2 N3 C2 . . . . -0.21(9) ?
N1 C1 N4 O1 . . . . -5.46(13) ?
N2 C1 N4 O1 . . . . 175.46(9) ?
N1 C1 N4 O2 . . . . 174.24(9) ?
N2 C1 N4 O2 . . . . -4.85(13) ?
N1 C2 N5 O3 . . . . -4.36(13) ?
N3 C2 N5 O3 . . . . 175.25(8) ?
N1 C2 N5 O4 . . . . 176.46(8) ?
N3 C2 N5 O4 . . . . -3.93(13) ?
C4 C3 N6 C5 . . . . -179.28(8) ?
C6 C5 N6 C3 . . . . 168.42(8) ?

####################################################################### 
# 
# 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_Et3NHDNT
_database_code_depnum_ccdc_archive 'CCDC 1006182'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Et3NHDNT
_chemical_formula_moiety         'C2 N5 O4, C6 H16 N'
_chemical_formula_sum            'C8 H16 N6 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         260.27

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   7.0842(5)
_cell_length_b                   9.3195(6)
_cell_length_c                   19.3391(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.3110(11)
_cell_angle_gamma                90
_cell_volume                     1256.17(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    29946
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      30.65
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.232
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            29946
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         30.65
_diffrn_reflns_theta_full        30.65
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_refine_special_details          
;
;

_reflns_number_total             3841
_reflns_number_gt                3189
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1022
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         3841
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.5128P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.484
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XLMP 2014/1 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.82004(14) 0.12816(10) 0.56321(5) 0.01597(19) Uani d . . . 1 . .
C C2 0.69179(14) 0.11022(11) 0.46243(5) 0.01575(19) Uani d . . . 1 . .
C C3 0.24304(15) 0.35101(11) 0.41424(5) 0.0177(2) Uani d . . . 1 . .
H H3A 0.3808 0.3424 0.4116 0.021 Uiso calc U . R 1 . .
H H3B 0.1784 0.2616 0.3952 0.021 Uiso calc U . R 1 . .
C C4 0.22214(17) 0.36755(12) 0.49031(6) 0.0226(2) Uani d . . . 1 . .
H H4A 0.2777 0.2838 0.5171 0.034 Uiso calc U . R 1 . .
H H4B 0.0859 0.3752 0.4933 0.034 Uiso calc U . R 1 . .
H H4C 0.2893 0.4544 0.5098 0.034 Uiso calc U . R 1 . .
C C5 -0.05759(14) 0.46655(11) 0.34903(6) 0.0178(2) Uani d . . . 1 . .
H H5A -0.1082 0.5617 0.332 0.021 Uiso calc U . R 1 . .
H H5B -0.1123 0.4426 0.3913 0.021 Uiso calc U . R 1 . .
C C6 -0.12484(16) 0.35571(12) 0.29252(6) 0.0215(2) Uani d . . . 1 . .
H H6A -0.0721 0.2616 0.3082 0.032 Uiso calc U . R 1 . .
H H6B -0.0805 0.3829 0.2491 0.032 Uiso calc U . R 1 . .
H H6C -0.2653 0.3511 0.2837 0.032 Uiso calc U . R 1 . .
C C7 0.25477(15) 0.49687(12) 0.30698(5) 0.0183(2) Uani d . . . 1 . .
H H7A 0.1731 0.5577 0.2717 0.022 Uiso calc U . R 1 . .
H H7B 0.2704 0.4026 0.2851 0.022 Uiso calc U . R 1 . .
C C8 0.44980(16) 0.56698(14) 0.32843(6) 0.0252(2) Uani d . . . 1 . .
H H8A 0.4339 0.6619 0.3484 0.038 Uiso calc U . R 1 . .
H H8B 0.5111 0.5771 0.2871 0.038 Uiso calc U . R 1 . .
H H8C 0.5303 0.5072 0.3636 0.038 Uiso calc U . R 1 . .
N N1 0.69958(12) 0.25202(9) 0.47367(4) 0.01647(17) Uani d . . . 1 . .
N N2 0.78518(12) 0.26379(9) 0.54215(4) 0.01586(17) Uani d . . . 1 . .
N N3 0.76506(13) 0.02513(9) 0.51615(5) 0.01835(18) Uani d . . . 1 . .
N N4 0.60249(14) 0.05214(10) 0.39467(5) 0.01969(18) Uani d . . . 1 . .
N N5 0.91361(15) 0.09765(10) 0.63454(5) 0.0223(2) Uani d . . . 1 . .
N N6 0.15806(12) 0.47643(9) 0.36969(4) 0.01362(16) Uani d . . . 1 . .
H H1 0.1823(19) 0.5567(15) 0.3959(7) 0.016 Uiso d U . . 1 . .
O O1 0.59269(16) -0.07892(9) 0.38865(5) 0.0341(2) Uani d . . . 1 . .
O O2 0.54033(13) 0.13713(9) 0.34776(4) 0.02656(19) Uani d . . . 1 . .
O O3 0.97036(18) -0.02496(9) 0.64869(5) 0.0447(3) Uani d . . . 1 . .
O O4 0.93216(13) 0.19736(9) 0.67694(4) 0.02596(19) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N3 . 1.3323(13) ?
C1 N2 . 1.3374(12) ?
C1 N5 . 1.4476(13) ?
C2 N3 . 1.3359(13) ?
C2 N1 . 1.3388(13) ?
C2 N4 . 1.4538(13) ?
C3 N6 . 1.5117(13) ?
C3 C4 . 1.5125(14) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 N6 . 1.5111(13) ?
C5 C6 . 1.5173(14) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 N6 . 1.5080(13) ?
C7 C8 . 1.5174(15) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
N1 N2 . 1.3589(12) ?
N4 O2 . 1.2253(12) ?
N4 O1 . 1.2277(12) ?
N5 O3 . 1.2258(12) ?
N5 O4 . 1.2308(12) ?
N6 H1 . 0.903(14) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 C1 N2 . . 117.24(9) ?
N3 C1 N5 . . 122.50(9) ?
N2 C1 N5 . . 120.26(9) ?
N3 C2 N1 . . 117.44(9) ?
N3 C2 N4 . . 121.72(9) ?
N1 C2 N4 . . 120.83(9) ?
N6 C3 C4 . . 112.16(8) ?
N6 C3 H3A . . 109.2 ?
C4 C3 H3A . . 109.2 ?
N6 C3 H3B . . 109.2 ?
C4 C3 H3B . . 109.2 ?
H3A C3 H3B . . 107.9 ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N6 C5 C6 . . 113.84(8) ?
N6 C5 H5A . . 108.8 ?
C6 C5 H5A . . 108.8 ?
N6 C5 H5B . . 108.8 ?
C6 C5 H5B . . 108.8 ?
H5A C5 H5B . . 107.7 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
N6 C7 C8 . . 110.92(8) ?
N6 C7 H7A . . 109.5 ?
C8 C7 H7A . . 109.5 ?
N6 C7 H7B . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.0 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C2 N1 N2 . . 103.66(8) ?
C1 N2 N1 . . 104.26(8) ?
C1 N3 C2 . . 97.40(8) ?
O2 N4 O1 . . 124.48(9) ?
O2 N4 C2 . . 117.87(9) ?
O1 N4 C2 . . 117.65(9) ?
O3 N5 O4 . . 124.29(10) ?
O3 N5 C1 . . 118.15(9) ?
O4 N5 C1 . . 117.56(9) ?
C7 N6 C5 . . 112.24(8) ?
C7 N6 C3 . . 111.35(8) ?
C5 N6 C3 . . 112.60(8) ?
C7 N6 H1 . . 106.2(8) ?
C5 N6 H1 . . 106.3(8) ?
C3 N6 H1 . . 107.7(8) ?

####################################################################### 
# 
# 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_PPNDNT
_database_code_depnum_ccdc_archive 'CCDC 1006184'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            PPNDNT
_chemical_formula_moiety         'C36 H30 N P2, C2 N5 O4'
_chemical_formula_sum            'C38 H30 N6 O4 P2'
_chemical_formula_iupac          ?
_chemical_formula_weight         696.62

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9099(7)
_cell_length_b                   11.9031(8)
_cell_length_c                   14.4603(10)
_cell_angle_alpha                112.6130(8)
_cell_angle_beta                 90.0610(9)
_cell_angle_gamma                103.5780(9)
_cell_volume                     1676.28(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5002
_cell_measurement_theta_min      2.3402
_cell_measurement_theta_max      28.0640
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724

_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            10859
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         28.67
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             7529
_reflns_number_gt                5805
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1273
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_number_reflns         7529
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.3671P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'SMART V5.632'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XLMP 2014/1 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.07394(19) 0.37659(18) 0.69103(15) 0.0254(4) Uani d . . . 1 . .
C C2 -0.05606(18) 0.44309(18) 0.77806(15) 0.0240(4) Uani d . . . 1 . .
C C3 0.54930(17) 0.31309(17) 0.39008(14) 0.0186(4) Uani d . . . 1 . .
C C4 0.67904(18) 0.37103(18) 0.41216(15) 0.0235(4) Uani d . . . 1 . .
H H4 0.7325 0.3615 0.3593 0.028 Uiso calc U . R 1 . .
C C5 0.72976(19) 0.44236(18) 0.51105(15) 0.0266(4) Uani d . . . 1 . .
H H5 0.8181 0.481 0.526 0.032 Uiso calc U . R 1 . .
C C6 0.6520(2) 0.45749(18) 0.58823(15) 0.0260(4) Uani d . . . 1 . .
H H6 0.6876 0.5047 0.6561 0.031 Uiso calc U . R 1 . .
C C7 0.52218(19) 0.40392(18) 0.56687(15) 0.0247(4) Uani d . . . 1 . .
H H7 0.4689 0.4166 0.6199 0.03 Uiso calc U . R 1 . .
C C8 0.47060(18) 0.33201(17) 0.46809(14) 0.0205(4) Uani d . . . 1 . .
H H8 0.3818 0.2956 0.4534 0.025 Uiso calc U . R 1 . .
C C9 0.54876(17) 0.08009(17) 0.21975(14) 0.0201(4) Uani d . . . 1 . .
C C10 0.50968(19) -0.00960(19) 0.12126(14) 0.0261(4) Uani d . . . 1 . .
H H10 0.4535 0.0039 0.0787 0.031 Uiso calc U . R 1 . .
C C11 0.5526(2) -0.1176(2) 0.08592(16) 0.0318(5) Uani d . . . 1 . .
H H11 0.5256 -0.1782 0.0192 0.038 Uiso calc U . R 1 . .
C C12 0.6347(2) -0.1375(2) 0.14748(17) 0.0337(5) Uani d . . . 1 . .
H H12 0.6641 -0.2118 0.123 0.04 Uiso calc U . R 1 . .
C C13 0.6740(2) -0.0497(2) 0.24452(17) 0.0338(5) Uani d . . . 1 . .
H H13 0.7306 -0.0636 0.2865 0.041 Uiso calc U . R 1 . .
C C14 0.63134(19) 0.05844(19) 0.28094(15) 0.0261(4) Uani d . . . 1 . .
H H14 0.6584 0.1182 0.3479 0.031 Uiso calc U . R 1 . .
C C15 0.54321(17) 0.30383(17) 0.18794(13) 0.0193(4) Uani d . . . 1 . .
C C16 0.47063(19) 0.37510(18) 0.16719(14) 0.0233(4) Uani d . . . 1 . .
H H16 0.3878 0.3721 0.1879 0.028 Uiso calc U . R 1 . .
C C17 0.5204(2) 0.4506(2) 0.11590(16) 0.0308(5) Uani d . . . 1 . .
H H17 0.4714 0.4994 0.1017 0.037 Uiso calc U . R 1 . .
C C18 0.6408(2) 0.4547(2) 0.08557(17) 0.0344(5) Uani d . . . 1 . .
H H18 0.6745 0.5071 0.0512 0.041 Uiso calc U . R 1 . .
C C19 0.7129(2) 0.3833(2) 0.10461(16) 0.0322(5) Uani d . . . 1 . .
H H19 0.7952 0.386 0.0828 0.039 Uiso calc U . R 1 . .
C C20 0.66445(19) 0.3075(2) 0.15573(15) 0.0270(4) Uani d . . . 1 . .
H H20 0.7137 0.2582 0.1688 0.032 Uiso calc U . R 1 . .
C C21 0.27924(17) -0.02769(18) 0.30737(15) 0.0222(4) Uani d . . . 1 . .
C C22 0.30675(19) -0.14129(19) 0.24983(17) 0.0293(5) Uani d . . . 1 . .
H H22 0.2919 -0.1751 0.1785 0.035 Uiso calc U . R 1 . .
C C23 0.3562(2) -0.2049(2) 0.2976(2) 0.0384(6) Uani d . . . 1 . .
H H23 0.3759 -0.2821 0.2587 0.046 Uiso calc U . R 1 . .
C C24 0.3767(2) -0.1563(2) 0.4012(2) 0.0409(6) Uani d . . . 1 . .
H H24 0.4099 -0.2007 0.4332 0.049 Uiso calc U . R 1 . .
C C25 0.34950(19) -0.0443(2) 0.45865(18) 0.0329(5) Uani d . . . 1 . .
H H25 0.3639 -0.0118 0.53 0.039 Uiso calc U . R 1 . .
C C26 0.30133(18) 0.02092(19) 0.41273(15) 0.0249(4) Uani d . . . 1 . .
H H26 0.2832 0.0986 0.4524 0.03 Uiso calc U . R 1 . .
C C27 0.15141(18) -0.03554(18) 0.12688(14) 0.0221(4) Uani d . . . 1 . .
C C28 0.18225(19) -0.0039(2) 0.04534(15) 0.0261(4) Uani d . . . 1 . .
H H28 0.245 0.071 0.0548 0.031 Uiso calc U . R 1 . .
C C29 0.1212(2) -0.0820(2) -0.05039(16) 0.0333(5) Uani d . . . 1 . .
H H29 0.1422 -0.0603 -0.1061 0.04 Uiso calc U . R 1 . .
C C30 0.0302(2) -0.1908(2) -0.06416(17) 0.0372(5) Uani d . . . 1 . .
H H30 -0.0105 -0.2446 -0.1296 0.045 Uiso calc U . R 1 . .
C C31 -0.0019(2) -0.2219(2) 0.01710(18) 0.0380(5) Uani d . . . 1 . .
H H31 -0.0656 -0.2964 0.0072 0.046 Uiso calc U . R 1 . .
C C32 0.0578(2) -0.1456(2) 0.11242(16) 0.0314(5) Uani d . . . 1 . .
H H32 0.0357 -0.1677 0.1679 0.038 Uiso calc U . R 1 . .
C C33 0.10477(17) 0.12406(18) 0.32572(14) 0.0202(4) Uani d . . . 1 . .
C C34 0.08232(18) 0.23847(18) 0.33571(14) 0.0224(4) Uani d . . . 1 . .
H H34 0.1309 0.2863 0.3026 0.027 Uiso calc U . R 1 . .
C C35 -0.01034(18) 0.28286(19) 0.39363(15) 0.0259(4) Uani d . . . 1 . .
H H35 -0.0266 0.3601 0.3992 0.031 Uiso calc U . R 1 . .
C C36 -0.07960(19) 0.2140(2) 0.44369(15) 0.0272(4) Uani d . . . 1 . .
H H36 -0.1405 0.2461 0.486 0.033 Uiso calc U . R 1 . .
C C37 -0.06006(19) 0.0989(2) 0.43193(16) 0.0287(5) Uani d . . . 1 . .
H H37 -0.1091 0.0512 0.4649 0.034 Uiso calc U . R 1 . .
C C38 0.03039(18) 0.05285(19) 0.37246(15) 0.0256(4) Uani d . . . 1 . .
H H38 0.042 -0.0272 0.3633 0.031 Uiso calc U . R 1 . .
N N1 -0.03406(17) 0.51115(16) 0.72238(13) 0.0292(4) Uani d . . . 1 . .
N N2 0.05519(17) 0.46608(16) 0.66335(13) 0.0302(4) Uani d . . . 1 . .
N N3 0.00801(16) 0.35644(16) 0.76297(13) 0.0272(4) Uani d . . . 1 . .
N N4 -0.14534(17) 0.46497(17) 0.85265(14) 0.0316(4) Uani d . . . 1 . .
N N5 0.16231(17) 0.30310(17) 0.64344(15) 0.0326(4) Uani d . . . 1 . .
N N6 0.33309(14) 0.18096(14) 0.24908(12) 0.0199(3) Uani d . . . 1 . .
O O1 -0.14512(18) 0.41770(17) 0.91407(13) 0.0487(5) Uani d . . . 1 . .
O O2 -0.21701(15) 0.52994(16) 0.85036(13) 0.0424(4) Uani d . . . 1 . .
O O3 0.17244(18) 0.21875(18) 0.66908(16) 0.0577(5) Uani d . . . 1 . .
O O4 0.22110(16) 0.32838(17) 0.57930(13) 0.0470(4) Uani d . . . 1 . .
P P1 0.48354(4) 0.21555(4) 0.26231(3) 0.01743(12) Uani d . . . 1 . .
P P2 0.22558(4) 0.06609(4) 0.25143(4) 0.01855(12) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.329(3) ?
C1 N3 . 1.330(3) ?
C1 N5 . 1.450(3) ?
C2 N3 . 1.329(3) ?
C2 N1 . 1.332(3) ?
C2 N4 . 1.444(3) ?
C3 C4 . 1.397(3) ?
C3 C8 . 1.399(3) ?
C3 P1 . 1.7979(18) ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.390(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.386(3) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C9 C14 . 1.394(3) ?
C9 C10 . 1.402(3) ?
C9 P1 . 1.8060(19) ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.383(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.382(3) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 C16 . 1.395(3) ?
C15 C20 . 1.399(3) ?
C15 P1 . 1.7982(18) ?
C16 C17 . 1.392(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.382(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.382(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.389(3) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 C22 . 1.392(3) ?
C21 C26 . 1.404(3) ?
C21 P2 . 1.8008(19) ?
C22 C23 . 1.390(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.379(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.375(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.381(3) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C27 C28 . 1.388(3) ?
C27 C32 . 1.401(3) ?
C27 P2 . 1.7955(19) ?
C28 C29 . 1.394(3) ?
C28 H28 . 0.95 ?
C29 C30 . 1.378(3) ?
C29 H29 . 0.95 ?
C30 C31 . 1.384(3) ?
C30 H30 . 0.95 ?
C31 C32 . 1.381(3) ?
C31 H31 . 0.95 ?
C32 H32 . 0.95 ?
C33 C34 . 1.393(3) ?
C33 C38 . 1.397(3) ?
C33 P2 . 1.797(2) ?
C34 C35 . 1.384(3) ?
C34 H34 . 0.95 ?
C35 C36 . 1.390(3) ?
C35 H35 . 0.95 ?
C36 C37 . 1.382(3) ?
C36 H36 . 0.95 ?
C37 C38 . 1.381(3) ?
C37 H37 . 0.95 ?
C38 H38 . 0.95 ?
N1 N2 . 1.364(2) ?
N4 O1 . 1.221(2) ?
N4 O2 . 1.230(2) ?
N5 O4 . 1.220(2) ?
N5 O3 . 1.223(2) ?
N6 P1 . 1.5881(16) ?
N6 P2 . 1.5903(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N3 . . 117.61(18) ?
N2 C1 N5 . . 120.88(18) ?
N3 C1 N5 . . 121.50(18) ?
N3 C2 N1 . . 117.52(18) ?
N3 C2 N4 . . 121.94(18) ?
N1 C2 N4 . . 120.54(18) ?
C4 C3 C8 . . 119.54(17) ?
C4 C3 P1 . . 120.33(14) ?
C8 C3 P1 . . 120.13(14) ?
C5 C4 C3 . . 120.03(18) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.15(18) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C7 . . 120.31(18) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 119.92(18) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C3 . . 119.98(18) ?
C7 C8 H8 . . 120.0 ?
C3 C8 H8 . . 120.0 ?
C14 C9 C10 . . 118.92(18) ?
C14 C9 P1 . . 123.33(15) ?
C10 C9 P1 . . 117.70(14) ?
C11 C10 C9 . . 120.25(18) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C12 . . 120.1(2) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C13 C12 C11 . . 120.1(2) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 120.35(19) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C13 C14 C9 . . 120.25(19) ?
C13 C14 H14 . . 119.9 ?
C9 C14 H14 . . 119.9 ?
C16 C15 C20 . . 119.73(17) ?
C16 C15 P1 . . 119.50(14) ?
C20 C15 P1 . . 120.66(15) ?
C17 C16 C15 . . 119.60(19) ?
C17 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C18 C17 C16 . . 120.1(2) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C19 C18 C17 . . 120.73(19) ?
C19 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C18 C19 C20 . . 119.8(2) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C19 C20 C15 . . 120.04(19) ?
C19 C20 H20 . . 120.0 ?
C15 C20 H20 . . 120.0 ?
C22 C21 C26 . . 119.61(18) ?
C22 C21 P2 . . 122.33(16) ?
C26 C21 P2 . . 117.94(15) ?
C23 C22 C21 . . 119.5(2) ?
C23 C22 H22 . . 120.3 ?
C21 C22 H22 . . 120.3 ?
C24 C23 C22 . . 120.2(2) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C25 C24 C23 . . 120.7(2) ?
C25 C24 H24 . . 119.7 ?
C23 C24 H24 . . 119.7 ?
C24 C25 C26 . . 120.0(2) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C25 C26 C21 . . 120.0(2) ?
C25 C26 H26 . . 120.0 ?
C21 C26 H26 . . 120.0 ?
C28 C27 C32 . . 119.61(18) ?
C28 C27 P2 . . 120.77(15) ?
C32 C27 P2 . . 119.58(15) ?
C27 C28 C29 . . 120.06(19) ?
C27 C28 H28 . . 120.0 ?
C29 C28 H28 . . 120.0 ?
C30 C29 C28 . . 120.0(2) ?
C30 C29 H29 . . 120.0 ?
C28 C29 H29 . . 120.0 ?
C29 C30 C31 . . 120.2(2) ?
C29 C30 H30 . . 119.9 ?
C31 C30 H30 . . 119.9 ?
C32 C31 C30 . . 120.6(2) ?
C32 C31 H31 . . 119.7 ?
C30 C31 H31 . . 119.7 ?
C31 C32 C27 . . 119.6(2) ?
C31 C32 H32 . . 120.2 ?
C27 C32 H32 . . 120.2 ?
C34 C33 C38 . . 119.34(18) ?
C34 C33 P2 . . 120.71(14) ?
C38 C33 P2 . . 119.94(15) ?
C35 C34 C33 . . 120.34(18) ?
C35 C34 H34 . . 119.8 ?
C33 C34 H34 . . 119.8 ?
C34 C35 C36 . . 119.75(19) ?
C34 C35 H35 . . 120.1 ?
C36 C35 H35 . . 120.1 ?
C37 C36 C35 . . 120.11(19) ?
C37 C36 H36 . . 119.9 ?
C35 C36 H36 . . 119.9 ?
C38 C37 C36 . . 120.35(19) ?
C38 C37 H37 . . 119.8 ?
C36 C37 H37 . . 119.8 ?
C37 C38 C33 . . 119.99(19) ?
C37 C38 H38 . . 120.0 ?
C33 C38 H38 . . 120.0 ?
C2 N1 N2 . . 103.77(16) ?
C1 N2 N1 . . 103.76(16) ?
C2 N3 C1 . . 97.34(16) ?
O1 N4 O2 . . 124.03(19) ?
O1 N4 C2 . . 117.92(19) ?
O2 N4 C2 . . 118.05(18) ?
O4 N5 O3 . . 123.9(2) ?
O4 N5 C1 . . 117.84(18) ?
O3 N5 C1 . . 118.20(18) ?
P1 N6 P2 . . 133.74(10) ?
N6 P1 C3 . . 112.90(8) ?
N6 P1 C15 . . 108.84(8) ?
C3 P1 C15 . . 106.55(8) ?
N6 P1 C9 . . 113.77(8) ?
C3 P1 C9 . . 107.97(9) ?
C15 P1 C9 . . 106.37(9) ?
N6 P2 C27 . . 110.84(9) ?
N6 P2 C33 . . 109.69(9) ?
C27 P2 C33 . . 107.51(9) ?
N6 P2 C21 . . 114.52(8) ?
C27 P2 C21 . . 108.41(9) ?
C33 P2 C21 . . 105.53(9) ?

####################################################################### 
# 
# 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_PyrDNT
_database_code_depnum_ccdc_archive 'CCDC 1006408'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            PyrDNT
_chemical_formula_moiety         'C2 N5 O4, C5 H6 N, H2 O'
_chemical_formula_sum            'C7 H8 N6 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         256.19

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   13.9051(6)
_cell_length_b                   26.2532(12)
_cell_length_c                   6.3689(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.9480(7)
_cell_angle_gamma                90
_cell_volume                     2156.48(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.8128
_cell_measurement_theta_max      30.5439
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear orange'
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.361
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056

_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            26448
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_full        30.55
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             3279
_reflns_number_gt                2729
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1042
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_number_reflns         3279
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.7631P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XLMP 2014/1 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.24371(7) 0.33320(3) 0.23954(14) 0.01535(17) Uani d . . . 1 . .
C C2 0.24375(6) 0.40971(3) 0.24424(14) 0.01510(17) Uani d . . . 1 . .
C C3 0.04673(7) 0.34465(3) 0.62966(15) 0.02008(18) Uani d . . . 1 . .
H H3 0.0787 0.326 0.5456 0.024 Uiso calc U . R 1 . .
C C4 0.04841(7) 0.39712(4) 0.62805(16) 0.02154(19) Uani d . . . 1 . .
H H4 0.0821 0.4149 0.545 0.026 Uiso calc U . R 1 . .
C C5 0 0.42351(5) 0.75 0.0216(3) Uani d T P S 1 . .
H H5 0 0.4597 0.75 0.026 Uiso calc U P R 1 . .
C C6 0.57873(7) 0.40782(3) 0.72123(14) 0.01873(18) Uani d . . . 1 . .
H H6 0.6331 0.4265 0.7009 0.022 Uiso calc U . R 1 . .
C C7 0.58060(7) 0.35528(3) 0.72116(14) 0.01768(17) Uani d . . . 1 . .
H H7 0.6362 0.3375 0.7017 0.021 Uiso calc U . R 1 . .
C C8 0.5 0.32875(5) 0.75 0.0173(2) Uani d T P S 1 . .
H H8 0.5 0.2926 0.75 0.021 Uiso calc U P R 1 . .
N N1 0.18551(6) 0.37115(3) 0.26559(13) 0.01647(16) Uani d . . . 1 . .
N N2 0.32959(6) 0.34592(3) 0.20560(13) 0.01778(16) Uani d . . . 1 . .
N N3 0.32984(6) 0.39769(3) 0.20870(13) 0.01712(16) Uani d . . . 1 . .
N N4 0.21586(6) 0.28019(3) 0.24785(12) 0.01905(17) Uani d . . . 1 . .
N N5 0.21609(6) 0.46257(3) 0.25740(13) 0.01876(16) Uani d . . . 1 . .
N N6 0 0.31993(4) 0.75 0.0186(2) Uani d T P S 1 . .
H H1 0 0.2869(7) 0.75 0.022 Uiso d U P S 1 . .
N N7 0.5 0.43253(4) 0.75 0.0185(2) Uani d T P S 1 . .
H H2 0.5 0.4661(7) 0.75 0.022 Uiso d U P S 1 . .
O O1 0.13107(6) 0.27141(3) 0.25770(14) 0.03168(19) Uani d . . . 1 . .
O O2 0.27825(6) 0.24766(3) 0.24498(14) 0.03254(19) Uani d . . . 1 . .
O O3 0.13245(6) 0.47157(3) 0.27208(14) 0.02777(18) Uani d . . . 1 . .
O O4 0.27912(6) 0.49495(3) 0.25281(14) 0.02775(18) Uani d . . . 1 . .
O O1W 0.5 0.28002(4) 0.25 0.0246(2) Uani d T P S 1 . .
H H1W 0.4460(10) 0.2985(5) 0.235(2) 0.029 Uiso d U . . 1 . .
O O2W 0.5 0.46591(3) 0.25 0.01942(19) Uani d T P S 1 . .
H H2W 0.5513(9) 0.4477(5) 0.263(2) 0.023 Uiso d U . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3324(11) ?
C1 N2 . 1.3331(11) ?
C1 N4 . 1.4509(11) ?
C2 N1 . 1.3347(10) ?
C2 N3 . 1.3365(11) ?
C2 N5 . 1.4509(11) ?
C3 N6 . 1.3429(10) ?
C3 C4 . 1.3777(13) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3882(11) ?
C4 H4 . 0.95 ?
C5 C4 2_556 1.3882(11) ?
C5 H5 . 0.95 ?
C6 N7 . 1.3426(10) ?
C6 C7 . 1.3797(12) ?
C6 H6 . 0.95 ?
C7 C8 . 1.3889(10) ?
C7 H7 . 0.95 ?
C8 C7 2_656 1.3889(10) ?
C8 H8 . 0.95 ?
N2 N3 . 1.3592(11) ?
N4 O2 . 1.2225(11) ?
N4 O1 . 1.2257(11) ?
N5 O3 . 1.2241(10) ?
N5 O4 . 1.2290(10) ?
N6 C3 2_556 1.3428(10) ?
N6 H1 . 0.866(18) ?
N7 C6 2_656 1.3426(10) ?
N7 H2 . 0.880(18) ?
O1W H1W . 0.868(13) ?
O2W H2W . 0.837(12) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 117.10(8) ?
N1 C1 N4 . . 121.99(8) ?
N2 C1 N4 . . 120.91(8) ?
N1 C2 N3 . . 117.00(8) ?
N1 C2 N5 . . 122.38(7) ?
N3 C2 N5 . . 120.61(7) ?
N6 C3 C4 . . 120.04(8) ?
N6 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 118.80(8) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C4 C5 C4 2_556 . 120.12(12) ?
C4 C5 H5 2_556 . 119.9 ?
C4 C5 H5 . . 119.9 ?
N7 C6 C7 . . 119.97(8) ?
N7 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C6 C7 C8 . . 119.02(8) ?
C6 C7 H7 . . 120.5 ?
C8 C7 H7 . . 120.5 ?
C7 C8 C7 2_656 . 119.80(11) ?
C7 C8 H8 2_656 . 120.1 ?
C7 C8 H8 . . 120.1 ?
C1 N1 C2 . . 97.73(7) ?
C1 N2 N3 . . 104.22(7) ?
C2 N3 N2 . . 103.95(7) ?
O2 N4 O1 . . 124.82(8) ?
O2 N4 C1 . . 117.97(8) ?
O1 N4 C1 . . 117.21(8) ?
O3 N5 O4 . . 125.08(8) ?
O3 N5 C2 . . 117.96(7) ?
O4 N5 C2 . . 116.96(7) ?
C3 N6 C3 2_556 . 122.19(11) ?
C3 N6 H1 2_556 . 118.90(5) ?
C3 N6 H1 . . 118.91(5) ?
C6 N7 C6 2_656 . 122.23(11) ?
C6 N7 H2 2_656 . 118.89(5) ?
C6 N7 H2 . . 118.88(5) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1006639'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C2 N5 O4, C H6 N3'
_chemical_formula_sum            'C3 H6 N8 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         218.16

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   8.3235(7)
_cell_length_b                   16.7996(14)
_cell_length_c                   12.3068(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.3250(13)
_cell_angle_gamma                90
_cell_volume                     1681.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.4243
_cell_measurement_theta_max      30.5151
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.801
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.274
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896

_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            20271
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_full        30.52
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2562
_reflns_number_gt                2221
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1189
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_number_reflns         2562
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+1.5987P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XLMP 2014/1 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.45529(14) 0.21803(7) 0.55973(10) 0.0183(2) Uani d . . . 1 . .
C C2 0.50191(15) 0.31605(7) 0.47779(9) 0.0181(2) Uani d . . . 1 . .
C C3 0.22225(14) 0.40070(7) 0.78750(10) 0.0182(2) Uani d . . . 1 . .
H H1 0.299(3) 0.4901(15) 0.7310(18) 0.046(6) Uiso d . . . 1 . .
H H2 0.322(3) 0.4238(14) 0.6664(19) 0.039(6) Uiso d . . . 1 . .
H H3 0.159(3) 0.482(2) 0.866(2) 0.067(9) Uiso d . . . 1 . .
H H4 0.120(3) 0.4103(13) 0.9053(18) 0.034(5) Uiso d . . . 1 . .
H H5 0.175(3) 0.2971(13) 0.8200(17) 0.034(5) Uiso d . . . 1 . .
H H6 0.255(2) 0.3062(11) 0.7319(16) 0.024(4) Uiso d . . . 1 . .
N N1 0.42001(13) 0.34343(7) 0.55183(9) 0.0212(2) Uani d . . . 1 . .
N N2 0.38860(14) 0.27727(7) 0.60685(9) 0.0211(2) Uani d . . . 1 . .
N N3 0.52994(13) 0.23721(7) 0.47756(8) 0.0198(2) Uani d . . . 1 . .
N N4 0.43571(14) 0.13733(7) 0.59504(9) 0.0219(2) Uani d . . . 1 . .
N N5 0.55743(14) 0.36971(7) 0.40095(9) 0.0218(2) Uani d . . . 1 . .
N N6 0.28742(15) 0.44451(7) 0.71836(10) 0.0249(2) Uani d . . . 1 . .
N N7 0.16520(17) 0.43552(10) 0.86842(12) 0.0322(3) Uani d . . . 1 . .
N N8 0.21329(14) 0.32243(7) 0.77699(10) 0.0209(2) Uani d . . . 1 . .
O O1 0.49918(15) 0.08366(6) 0.55042(10) 0.0341(3) Uani d . . . 1 . .
O O2 0.35507(13) 0.12595(7) 0.66590(8) 0.0275(2) Uani d . . . 1 . .
O O3 0.64830(13) 0.34261(7) 0.34287(9) 0.0291(2) Uani d . . . 1 . .
O O4 0.51029(14) 0.43882(6) 0.39762(9) 0.0301(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.3313(16) ?
C1 N3 . 1.3345(16) ?
C1 N4 . 1.4434(16) ?
C2 N1 . 1.3311(16) ?
C2 N3 . 1.3450(16) ?
C2 N5 . 1.4516(16) ?
C3 N8 . 1.3217(17) ?
C3 N6 . 1.3256(17) ?
C3 N7 . 1.3271(17) ?
N1 N2 . 1.3556(16) ?
N4 O2 . 1.2237(15) ?
N4 O1 . 1.2319(16) ?
N5 O4 . 1.2234(15) ?
N5 O3 . 1.2334(15) ?
N6 H1 . 0.78(3) ?
N6 H2 . 0.83(2) ?
N7 H3 . 0.79(3) ?
N7 H4 . 0.77(2) ?
N8 H5 . 0.80(2) ?
N8 H6 . 0.76(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N3 . . 117.03(11) ?
N2 C1 N4 . . 119.12(11) ?
N3 C1 N4 . . 123.75(11) ?
N1 C2 N3 . . 117.14(11) ?
N1 C2 N5 . . 120.80(11) ?
N3 C2 N5 . . 122.06(11) ?
N8 C3 N6 . . 120.78(12) ?
N8 C3 N7 . . 119.36(13) ?
N6 C3 N7 . . 119.86(14) ?
C2 N1 N2 . . 103.89(10) ?
C1 N2 N1 . . 104.63(10) ?
C1 N3 C2 . . 97.30(10) ?
O2 N4 O1 . . 123.78(12) ?
O2 N4 C1 . . 118.40(11) ?
O1 N4 C1 . . 117.81(11) ?
O4 N5 O3 . . 124.26(12) ?
O4 N5 C2 . . 117.82(11) ?
O3 N5 C2 . . 117.91(11) ?
C3 N6 H1 . . 117.8(16) ?
C3 N6 H2 . . 121.1(16) ?
H1 N6 H2 . . 121.(2) ?
C3 N7 H3 . . 117.(2) ?
C3 N7 H4 . . 119.7(16) ?
H3 N7 H4 . . 122.(3) ?
C3 N8 H5 . . 119.2(15) ?
C3 N8 H6 . . 113.7(15) ?
H5 N8 H6 . . 127.(2) ?

####################################################################### 
# 
# 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_TPPDNT
_database_code_depnum_ccdc_archive 'CCDC 1009537'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            
'Tetraphenylphosphonium 3,5-dinitro-1,2,4 triazolate'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 N5 O4 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         497.44

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2261(5)
_cell_length_b                   15.0086(7)
_cell_length_c                   13.8078(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.0410(10)
_cell_angle_gamma                90
_cell_volume                     2317.45(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    50180
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      28.50
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.141
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032

_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_T_max  0.7457

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            50180
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_full        28.50
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             5872
_reflns_number_gt                4600
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0923
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_number_reflns         5872
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+1.1073P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XS 2013/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.18798(13) 0.83189(10) 0.41096(10) 0.0179(3) Uani d . . . 1 . .
C C2 0.16020(13) 0.86982(10) 0.27150(11) 0.0189(3) Uani d . . . 1 . .
N N1 0.24200(11) 0.79766(9) 0.50288(10) 0.0237(3) Uani d . . . 1 . .
N N2 0.07446(11) 0.85853(9) 0.40219(9) 0.0220(3) Uani d . . . 1 . .
N N3 0.05531(11) 0.88386(9) 0.30725(9) 0.0225(3) Uani d . . . 1 . .
N N4 0.17766(12) 0.89031(9) 0.17114(9) 0.0232(3) Uani d . . . 1 . .
N N5 0.24882(11) 0.83772(8) 0.33237(9) 0.0198(3) Uani d . . . 1 . .
O O1 0.08945(11) 0.91145(9) 0.11693(9) 0.0348(3) Uani d . . . 1 . .
O O2 0.28021(11) 0.88604(8) 0.14647(9) 0.0309(3) Uani d . . . 1 . .
O O3 0.17919(11) 0.79380(9) 0.57105(8) 0.0347(3) Uani d . . . 1 . .
O O4 0.34716(10) 0.77480(9) 0.50725(9) 0.0370(3) Uani d . . . 1 . .
C C3 0.16079(12) 0.29597(9) 0.72413(10) 0.0154(3) Uani d . . . 1 . .
C C4 0.10023(13) 0.31497(10) 0.63402(11) 0.0197(3) Uani d . . . 1 . .
H H5 0.1289 0.2926 0.576 0.024 Uiso calc U . R 1 . .
C C5 -0.00268(14) 0.36710(10) 0.62991(12) 0.0255(3) Uani d . . . 1 . .
H H4 -0.0453 0.3798 0.569 0.031 Uiso calc U . R 1 . .
C C6 -0.04280(14) 0.40039(11) 0.71473(13) 0.0273(4) Uani d . . . 1 . .
H H3 -0.1121 0.437 0.7113 0.033 Uiso calc U . R 1 . .
C C7 0.01652(14) 0.38114(10) 0.80449(12) 0.0255(3) Uani d . . . 1 . .
H H2 -0.0126 0.4037 0.8622 0.031 Uiso calc U . R 1 . .
C C8 0.11880(13) 0.32871(10) 0.80968(11) 0.0202(3) Uani d . . . 1 . .
H H1 0.16 0.3152 0.871 0.024 Uiso calc U . R 1 . .
C C9 0.31069(12) 0.17108(9) 0.83993(10) 0.0151(3) Uani d . . . 1 . .
C C10 0.20910(13) 0.12228(9) 0.86069(10) 0.0176(3) Uani d . . . 1 . .
H H6 0.1359 0.1285 0.8211 0.021 Uiso calc U . R 1 . .
C C11 0.21724(14) 0.06479(10) 0.93989(10) 0.0208(3) Uani d . . . 1 . .
H H7 0.1492 0.0316 0.9548 0.025 Uiso calc U . R 1 . .
C C12 0.32438(15) 0.05564(10) 0.99734(10) 0.0226(3) Uani d . . . 1 . .
H H8 0.3298 0.015 1.0503 0.027 Uiso calc U . R 1 . .
C C13 0.42336(14) 0.10529(10) 0.97801(11) 0.0216(3) Uani d . . . 1 . .
H H9 0.4957 0.0997 1.0188 0.026 Uiso calc U . R 1 . .
C C14 0.41768(13) 0.16334(9) 0.89936(10) 0.0177(3) Uani d . . . 1 . .
H H10 0.4857 0.1974 0.8861 0.021 Uiso calc U . R 1 . .
C C15 0.41948(12) 0.31892(9) 0.73757(9) 0.0150(3) Uani d . . . 1 . .
C C16 0.39146(13) 0.40975(9) 0.74134(10) 0.0168(3) Uani d . . . 1 . .
H H11 0.3104 0.4282 0.74 0.02 Uiso calc U . R 1 . .
C C17 0.48220(14) 0.47281(10) 0.74699(10) 0.0205(3) Uani d . . . 1 . .
H H12 0.4633 0.5344 0.7503 0.025 Uiso calc U . R 1 . .
C C18 0.60041(14) 0.44596(10) 0.74780(11) 0.0225(3) Uani d . . . 1 . .
H H13 0.6623 0.4893 0.751 0.027 Uiso calc U . R 1 . .
C C19 0.62893(14) 0.35603(10) 0.74394(11) 0.0221(3) Uani d . . . 1 . .
H H14 0.7102 0.3382 0.7445 0.026 Uiso calc U . R 1 . .
C C20 0.53935(13) 0.29228(10) 0.73921(10) 0.0183(3) Uani d . . . 1 . .
H H15 0.5591 0.2308 0.7371 0.022 Uiso calc U . R 1 . .
C C21 0.30728(12) 0.16568(9) 0.62837(10) 0.0146(3) Uani d . . . 1 . .
C C22 0.40426(13) 0.16498(10) 0.57166(10) 0.0181(3) Uani d . . . 1 . .
H H16 0.4672 0.2069 0.5834 0.022 Uiso calc U . R 1 . .
C C23 0.40796(14) 0.10232(10) 0.49772(10) 0.0205(3) Uani d . . . 1 . .
H H17 0.474 0.1013 0.4592 0.025 Uiso calc U . R 1 . .
C C24 0.31570(14) 0.04131(10) 0.47992(11) 0.0211(3) Uani d . . . 1 . .
H H18 0.3194 -0.002 0.4301 0.025 Uiso calc U . R 1 . .
C C25 0.21772(13) 0.04348(10) 0.53501(11) 0.0202(3) Uani d . . . 1 . .
H H19 0.1537 0.0027 0.5215 0.024 Uiso calc U . R 1 . .
C C26 0.21321(13) 0.10492(10) 0.60948(10) 0.0171(3) Uani d . . . 1 . .
H H20 0.1467 0.1059 0.6475 0.021 Uiso calc U . R 1 . .
P P1 0.30090(3) 0.23838(2) 0.73171(3) 0.01296(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.3310(19) ?
C1 N5 . 1.3348(19) ?
C1 N1 . 1.4516(19) ?
C2 N3 . 1.3330(19) ?
C2 N5 . 1.3347(19) ?
C2 N4 . 1.4494(19) ?
N1 O4 . 1.2258(17) ?
N1 O3 . 1.2261(17) ?
N2 N3 . 1.3637(18) ?
N4 O1 . 1.2294(17) ?
N4 O2 . 1.2306(17) ?
C3 C4 . 1.394(2) ?
C3 C8 . 1.399(2) ?
C3 P1 . 1.7897(14) ?
C4 C5 . 1.392(2) ?
C4 H5 . 0.95 ?
C5 C6 . 1.384(2) ?
C5 H4 . 0.95 ?
C6 C7 . 1.385(2) ?
C6 H3 . 0.95 ?
C7 C8 . 1.389(2) ?
C7 H2 . 0.95 ?
C8 H1 . 0.95 ?
C9 C14 . 1.3987(19) ?
C9 C10 . 1.4059(19) ?
C9 P1 . 1.7990(14) ?
C10 C11 . 1.390(2) ?
C10 H6 . 0.95 ?
C11 C12 . 1.388(2) ?
C11 H7 . 0.95 ?
C12 C13 . 1.383(2) ?
C12 H8 . 0.95 ?
C13 C14 . 1.389(2) ?
C13 H9 . 0.95 ?
C14 H10 . 0.95 ?
C15 C16 . 1.4010(19) ?
C15 C20 . 1.4021(19) ?
C15 P1 . 1.7946(14) ?
C16 C17 . 1.388(2) ?
C16 H11 . 0.95 ?
C17 C18 . 1.386(2) ?
C17 H12 . 0.95 ?
C18 C19 . 1.389(2) ?
C18 H13 . 0.95 ?
C19 C20 . 1.386(2) ?
C19 H14 . 0.95 ?
C20 H15 . 0.95 ?
C21 C22 . 1.3959(19) ?
C21 C26 . 1.4023(19) ?
C21 P1 . 1.8028(14) ?
C22 C23 . 1.391(2) ?
C22 H16 . 0.95 ?
C23 C24 . 1.388(2) ?
C23 H17 . 0.95 ?
C24 C25 . 1.392(2) ?
C24 H18 . 0.95 ?
C25 C26 . 1.385(2) ?
C25 H19 . 0.95 ?
C26 H20 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N5 . . 117.42(13) ?
N2 C1 N1 . . 120.60(13) ?
N5 C1 N1 . . 121.98(13) ?
N3 C2 N5 . . 117.24(13) ?
N3 C2 N4 . . 121.23(13) ?
N5 C2 N4 . . 121.52(13) ?
O4 N1 O3 . . 124.43(14) ?
O4 N1 C1 . . 117.94(13) ?
O3 N1 C1 . . 117.63(13) ?
C1 N2 N3 . . 103.89(12) ?
C2 N3 N2 . . 104.01(12) ?
O1 N4 O2 . . 124.61(14) ?
O1 N4 C2 . . 117.88(13) ?
O2 N4 C2 . . 117.51(13) ?
C2 N5 C1 . . 97.43(12) ?
C4 C3 C8 . . 120.52(13) ?
C4 C3 P1 . . 120.54(11) ?
C8 C3 P1 . . 118.67(11) ?
C5 C4 C3 . . 119.29(14) ?
C5 C4 H5 . . 120.4 ?
C3 C4 H5 . . 120.4 ?
C6 C5 C4 . . 119.92(15) ?
C6 C5 H4 . . 120.0 ?
C4 C5 H4 . . 120.0 ?
C5 C6 C7 . . 121.01(14) ?
C5 C6 H3 . . 119.5 ?
C7 C6 H3 . . 119.5 ?
C6 C7 C8 . . 119.65(15) ?
C6 C7 H2 . . 120.2 ?
C8 C7 H2 . . 120.2 ?
C7 C8 C3 . . 119.60(14) ?
C7 C8 H1 . . 120.2 ?
C3 C8 H1 . . 120.2 ?
C14 C9 C10 . . 120.48(13) ?
C14 C9 P1 . . 121.37(11) ?
C10 C9 P1 . . 118.06(10) ?
C11 C10 C9 . . 119.04(13) ?
C11 C10 H6 . . 120.5 ?
C9 C10 H6 . . 120.5 ?
C12 C11 C10 . . 120.32(14) ?
C12 C11 H7 . . 119.8 ?
C10 C11 H7 . . 119.8 ?
C13 C12 C11 . . 120.45(14) ?
C13 C12 H8 . . 119.8 ?
C11 C12 H8 . . 119.8 ?
C12 C13 C14 . . 120.41(14) ?
C12 C13 H9 . . 119.8 ?
C14 C13 H9 . . 119.8 ?
C13 C14 C9 . . 119.26(14) ?
C13 C14 H10 . . 120.4 ?
C9 C14 H10 . . 120.4 ?
C16 C15 C20 . . 119.68(13) ?
C16 C15 P1 . . 119.27(11) ?
C20 C15 P1 . . 121.05(11) ?
C17 C16 C15 . . 119.98(13) ?
C17 C16 H11 . . 120.0 ?
C15 C16 H11 . . 120.0 ?
C18 C17 C16 . . 119.98(14) ?
C18 C17 H12 . . 120.0 ?
C16 C17 H12 . . 120.0 ?
C17 C18 C19 . . 120.39(14) ?
C17 C18 H13 . . 119.8 ?
C19 C18 H13 . . 119.8 ?
C20 C19 C18 . . 120.26(14) ?
C20 C19 H14 . . 119.9 ?
C18 C19 H14 . . 119.9 ?
C19 C20 C15 . . 119.70(14) ?
C19 C20 H15 . . 120.2 ?
C15 C20 H15 . . 120.2 ?
C22 C21 C26 . . 120.16(13) ?
C22 C21 P1 . . 122.39(11) ?
C26 C21 P1 . . 117.34(10) ?
C23 C22 C21 . . 119.46(13) ?
C23 C22 H16 . . 120.3 ?
C21 C22 H16 . . 120.3 ?
C24 C23 C22 . . 120.39(13) ?
C24 C23 H17 . . 119.8 ?
C22 C23 H17 . . 119.8 ?
C23 C24 C25 . . 120.07(14) ?
C23 C24 H18 . . 120.0 ?
C25 C24 H18 . . 120.0 ?
C26 C25 C24 . . 120.23(14) ?
C26 C25 H19 . . 119.9 ?
C24 C25 H19 . . 119.9 ?
C25 C26 C21 . . 119.66(13) ?
C25 C26 H20 . . 120.2 ?
C21 C26 H20 . . 120.2 ?
C3 P1 C15 . . 108.78(7) ?
C3 P1 C9 . . 108.00(6) ?
C15 P1 C9 . . 110.48(6) ?
C3 P1 C21 . . 109.99(6) ?
C15 P1 C21 . . 111.25(6) ?
C9 P1 C21 . . 108.29(6) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1013941'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Et2NH2 DNT'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 N6 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         232.22

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3101(9)
_cell_length_b                   8.1876(10)
_cell_length_c                   9.9470(12)
_cell_angle_alpha                73.347(3)
_cell_angle_beta                 73.673(2)
_cell_angle_gamma                77.130(3)
_cell_volume                     540.79(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6034
_cell_measurement_theta_min      4.7759
_cell_measurement_theta_max      62.7874
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       blade
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.132
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244

_exptl_absorpt_coefficient_mu    1.036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.6498
_exptl_absorpt_correction_T_max  0.7523

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'IuS microsource'
_diffrn_source_type              ?

_diffrn_radiation_type           'CuK\a '
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multi-layer optics'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8580
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_theta_min         4.77
_diffrn_reflns_theta_max         63.184
_diffrn_reflns_theta_full        63.679
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.822
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             1606
_reflns_number_gt                1486
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0689
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         1606
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+0.1977P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.153
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2013/5 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XLMP 2014/1 (Bruker AXS, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.30428(18) 0.96776(15) 0.44942(13) 0.0203(3) Uani d . . . 1 . .
C C2 0.19128(18) 0.85170(16) 0.65347(13) 0.0205(3) Uani d . . . 1 . .
N N1 0.17401(15) 1.00668(13) 0.56371(11) 0.0225(3) Uani d . . . 1 . .
N N2 0.07672(16) 0.81592(14) 0.80045(12) 0.0253(3) Uani d . . . 1 . .
N N3 0.31868(15) 0.72668(13) 0.60306(11) 0.0232(3) Uani d . . . 1 . .
N N4 0.39540(16) 0.80537(13) 0.46418(11) 0.0229(3) Uani d . . . 1 . .
N N5 0.34971(16) 1.09380(14) 0.31357(11) 0.0245(3) Uani d . . . 1 . .
O O1 -0.04076(14) 0.93369(12) 0.84262(10) 0.0346(3) Uani d . . . 1 . .
O O2 0.10349(14) 0.66748(12) 0.87414(10) 0.0324(3) Uani d . . . 1 . .
O O3 0.25239(15) 1.23739(12) 0.30009(10) 0.0329(3) Uani d . . . 1 . .
O O4 0.48527(14) 1.04807(12) 0.21908(10) 0.0336(3) Uani d . . . 1 . .
C C3 0.3960(2) 0.6689(2) 0.11641(16) 0.0342(4) Uani d . . . 1 . .
H H3B 0.3867 0.5472 0.1633 0.051 Uiso calc U . R 1 . .
H H3C 0.363 0.6978 0.0226 0.051 Uiso calc U . R 1 . .
H H3A 0.3063 0.7415 0.1773 0.051 Uiso calc U . R 1 . .
C C4 0.59929(19) 0.69976(17) 0.09498(13) 0.0246(3) Uani d . . . 1 . .
H H4B 0.6887 0.6329 0.0277 0.03 Uiso calc U . R 1 . .
H H4A 0.6073 0.8236 0.0514 0.03 Uiso calc U . R 1 . .
C C5 0.84965(19) 0.69389(17) 0.22467(14) 0.0253(3) Uani d . . . 1 . .
H H5A 0.8394 0.8209 0.2038 0.03 Uiso calc U . R 1 . .
H H5B 0.947 0.6533 0.1445 0.03 Uiso calc U . R 1 . .
C C6 0.9130(2) 0.61250(17) 0.36410(14) 0.0268(3) Uani d . . . 1 . .
H H6B 1.0273 0.6582 0.3615 0.04 Uiso calc U . R 1 . .
H H6C 0.9443 0.4871 0.3763 0.04 Uiso calc U . R 1 . .
H H6A 0.8085 0.6393 0.445 0.04 Uiso calc U . R 1 . .
H H1 0.569(2) 0.700(2) 0.3006(17) 0.032 Uiso d U . . 1 . .
H H2 0.662(2) 0.532(2) 0.2719(17) 0.032 Uiso d U . . 1 . .
N N6 0.65847(16) 0.64737(14) 0.23511(11) 0.0211(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3283(16) ?
C1 N4 . 1.3348(16) ?
C1 N5 . 1.4500(17) ?
C2 N1 . 1.3289(16) ?
C2 N3 . 1.3317(16) ?
C2 N2 . 1.4492(17) ?
N2 O1 . 1.2262(14) ?
N2 O2 . 1.2316(14) ?
N3 N4 . 1.3613(15) ?
N5 O3 . 1.2235(14) ?
N5 O4 . 1.2322(14) ?
C3 C4 . 1.509(2) ?
C4 N6 . 1.4926(17) ?
C5 N6 . 1.4973(18) ?
C5 C6 . 1.5086(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N4 . . 117.11(11) ?
N1 C1 N5 . . 122.62(11) ?
N4 C1 N5 . . 120.27(11) ?
N1 C2 N3 . . 117.35(11) ?
N1 C2 N2 . . 122.51(11) ?
N3 C2 N2 . . 120.14(11) ?
C1 N1 C2 . . 97.75(10) ?
O1 N2 O2 . . 124.50(11) ?
O1 N2 C2 . . 118.33(11) ?
O2 N2 C2 . . 117.16(10) ?
C2 N3 N4 . . 103.83(10) ?
C1 N4 N3 . . 103.96(10) ?
O3 N5 O4 . . 124.41(11) ?
O3 N5 C1 . . 118.42(11) ?
O4 N5 C1 . . 117.17(10) ?
N6 C4 C3 . . 110.90(11) ?
N6 C5 C6 . . 110.30(11) ?
C4 N6 C5 . . 113.74(10) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1014382'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Aminoguanidinium DNT'
_chemical_formula_moiety         'C H7 N4, C2 N5 O4'
_chemical_formula_sum            'C3 H7 N9 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         233.18

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0616(3)
_cell_length_b                   16.2452(5)
_cell_length_c                   6.5935(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.189(3)
_cell_angle_gamma                90
_cell_volume                     910.98(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4503
_cell_measurement_theta_min      5.2056
_cell_measurement_theta_max      69.6364
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.096
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    1.338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2014/2'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'IuS microsource'
_diffrn_source_type              ?

_diffrn_radiation_type           'CuK\a '
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multi-layer optics'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            12104
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         72.18
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7

_refine_special_details          'Refined as a 2-component twin.'

_reflns_number_total             1692
_reflns_number_gt                1440
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_gt          0.2765
_refine_ls_wR_factor_ref         0.2846
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.207
_refine_ls_number_reflns         1692
_refine_ls_number_parameters     201
_refine_ls_number_restraints     35
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1444P)²+3.2934P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.423
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/3 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXTL XL 2014/3 (Bruker AXS, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XL 2014/3 (Bruker AXS, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C3 0.7907(6) 0.2022(3) 0.4460(8) 0.0196(10) Uani d . . . 1.0 . .
N N6 0.6410(5) 0.2084(3) 0.3259(7) 0.0266(10) Uani d . . D 1.0 . .
H H1 0.592(7) 0.162(2) 0.292(10) 0.032 Uiso d U . D 1.0 . .
H H2 0.581(6) 0.252(3) 0.294(10) 0.032 Uiso d U . D 1.0 . .
N N7 0.8563(5) 0.1302(3) 0.5165(7) 0.0239(10) Uani d . . D 1.0 . .
H H3 0.795(6) 0.087(2) 0.476(9) 0.029 Uiso d U . D 1.0 . .
H H4 0.955(3) 0.130(4) 0.599(8) 0.029 Uiso d U . D 1.0 . .
N N8 0.8763(5) 0.2710(2) 0.4945(7) 0.0255(10) Uani d . . D 1.0 . .
H H5 0.832(7) 0.318(2) 0.451(10) 0.031 Uiso d U . D 1.0 . .
N N9 1.0367(5) 0.2656(3) 0.6234(8) 0.0288(11) Uani d . . D 1.0 . .
H H9 1.089(7) 0.277(4) 0.535(9) 0.035 Uiso d U . D 1.0 . .
H H10 1.049(8) 0.302(3) 0.730(8) 0.035 Uiso d U . D 1.0 . .
C C1_a 0.4444(9) 0.4319(4) 0.180(3) 0.0187(14) Uani d . P D 0.914(4) A 1
C C2_a 0.6420(9) 0.4896(4) 0.3681(19) 0.0191(15) Uani d . P D 0.914(4) A 1
N N1_a 0.5378(5) 0.5500(3) 0.2983(7) 0.0199(10) Uani d . P D 0.914(4) A 1
N N2_a 0.4049(5) 0.5124(3) 0.1712(7) 0.0203(10) Uani d . P D 0.914(4) A 1
N N3_a 0.5908(5) 0.4132(3) 0.2998(7) 0.0191(10) Uani d . P D 0.914(4) A 1
N N4_a 0.3280(5) 0.3735(3) 0.0597(9) 0.0221(11) Uani d . P D 0.914(4) A 1
N N5_a 0.7988(5) 0.5059(3) 0.5178(7) 0.0212(10) Uani d . P D 0.914(4) A 1
O O1_a 0.1973(4) 0.4002(3) -0.0482(7) 0.0283(10) Uani d . P D 0.914(4) A 1
O O2_a 0.3655(5) 0.3006(2) 0.0702(8) 0.0299(10) Uani d . P D 0.914(4) A 1
O O3_a 0.8287(5) 0.5766(2) 0.5855(7) 0.0285(10) Uani d . P D 0.914(4) A 1
O O4_a 0.8913(4) 0.4481(2) 0.5710(7) 0.0288(10) Uani d . P D 0.914(4) A 1
C C1A_b 0.464(10) 0.431(3) 0.19(3) 0.0187(14) Uani d . P D 0.086(4) A 2
C C2A_b 0.645(8) 0.495(2) 0.39(2) 0.0191(15) Uani d . P D 0.086(4) A 2
N N1A_b 0.702(4) 0.4191(19) 0.398(7) 0.0199(10) Uani d . P D 0.086(4) A 2
N N2A_b 0.576(4) 0.3742(19) 0.280(7) 0.0203(10) Uani d . P D 0.086(4) A 2
N N3A_b 0.500(4) 0.5084(18) 0.247(7) 0.0191(10) Uani d . P D 0.086(4) A 2
N N4A_b 0.313(4) 0.400(2) 0.049(11) 0.0221(11) Uani d . P D 0.086(4) A 2
N N5A_b 0.750(4) 0.5623(16) 0.494(7) 0.0212(10) Uani d . P D 0.086(4) A 2
O O1A_b 0.307(5) 0.326(2) 0.006(8) 0.0283(10) Uani d . P D 0.086(4) A 2
O O2A_b 0.206(4) 0.450(2) -0.026(7) 0.0299(10) Uani d . P D 0.086(4) A 2
O O3A_b 0.876(4) 0.545(2) 0.635(7) 0.0285(10) Uani d . P D 0.086(4) A 2
O O4A_b 0.695(4) 0.6315(17) 0.456(7) 0.0288(10) Uani d . P D 0.086(4) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 N6 . 1.317(6) ?
C3 N7 . 1.322(6) ?
C3 N8 . 1.335(6) ?
N6 H1 . 0.86(2) ?
N6 H2 . 0.87(2) ?
N7 H3 . 0.88(2) ?
N7 H4 . 0.87(2) ?
N8 N9 . 1.411(6) ?
N8 H5 . 0.87(2) ?
N9 H9 . 0.89(2) ?
N9 H10 . 0.89(2) ?
C1_a N3_a . 1.323(7) ?
C1_a N2_a . 1.351(8) ?
C1_a N4_a . 1.439(7) ?
C1_a C2_a . 2.021(7) ?
C2_a N1_a . 1.330(8) ?
C2_a N3_a . 1.347(7) ?
C2_a N5_a . 1.447(7) ?
N1_a N2_a . 1.353(6) ?
N4_a O2_a . 1.227(6) ?
N4_a O1_a . 1.231(6) ?
N5_a O4_a . 1.227(6) ?
N5_a O3_a . 1.228(6) ?
C1A_b N3A_b . 1.326(19) ?
C1A_b N2A_b . 1.35(2) ?
C1A_b N4A_b . 1.443(19) ?
C1A_b C2A_b . 2.020(18) ?
C2A_b N1A_b . 1.33(2) ?
C2A_b N3A_b . 1.35(2) ?
C2A_b N5A_b . 1.451(19) ?
N1A_b N2A_b . 1.351(19) ?
N4A_b O2A_b . 1.229(19) ?
N4A_b O1A_b . 1.235(19) ?
N5A_b O4A_b . 1.219(19) ?
N5A_b O3A_b . 1.232(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N6 C3 N7 . . 121.6(4) ?
N6 C3 N8 . . 118.2(4) ?
N7 C3 N8 . . 120.2(4) ?
C3 N6 H1 . . 115.(4) ?
C3 N6 H2 . . 129.(4) ?
H1 N6 H2 . . 115.(6) ?
C3 N7 H3 . . 116.(4) ?
C3 N7 H4 . . 118.(4) ?
H3 N7 H4 . . 126.(6) ?
C3 N8 N9 . . 119.0(4) ?
C3 N8 H5 . . 120.(4) ?
N9 N8 H5 . . 121.(4) ?
N8 N9 H9 . . 105.(4) ?
N8 N9 H10 . . 105.(4) ?
H9 N9 H10 . . 115.(6) ?
N3_a C1_a N2_a . . 116.5(5) ?
N3_a C1_a N4_a . . 124.8(6) ?
N2_a C1_a N4_a . . 118.7(5) ?
N3_a C1_a C2_a . . 41.3(3) ?
N2_a C1_a C2_a . . 75.2(4) ?
N4_a C1_a C2_a . . 166.0(5) ?
N1_a C2_a N3_a . . 116.3(5) ?
N1_a C2_a N5_a . . 120.9(5) ?
N3_a C2_a N5_a . . 122.7(5) ?
N1_a C2_a C1_a . . 75.9(4) ?
N3_a C2_a C1_a . . 40.4(3) ?
N5_a C2_a C1_a . . 162.9(5) ?
C2_a N1_a N2_a . . 104.8(4) ?
C1_a N2_a N1_a . . 104.1(4) ?
C1_a N3_a C2_a . . 98.4(5) ?
O2_a N4_a O1_a . . 124.4(4) ?
O2_a N4_a C1_a . . 118.0(4) ?
O1_a N4_a C1_a . . 117.6(5) ?
O4_a N5_a O3_a . . 124.7(4) ?
O4_a N5_a C2_a . . 117.9(4) ?
O3_a N5_a C2_a . . 117.5(4) ?
N3A_b C1A_b N2A_b . . 116.2(18) ?
N3A_b C1A_b N4A_b . . 127.(3) ?
N2A_b C1A_b N4A_b . . 117.(3) ?
N3A_b C1A_b C2A_b . . 41.5(10) ?
N2A_b C1A_b C2A_b . . 74.7(14) ?
N4A_b C1A_b C2A_b . . 167.(8) ?
N1A_b C2A_b N3A_b . . 116.(2) ?
N1A_b C2A_b N5A_b . . 120.(3) ?
N3A_b C2A_b N5A_b . . 122.(3) ?
N1A_b C2A_b C1A_b . . 76.1(15) ?
N3A_b C2A_b C1A_b . . 40.5(9) ?
N5A_b C2A_b C1A_b . . 162.(5) ?
C2A_b N1A_b N2A_b . . 104.0(19) ?
N1A_b N2A_b C1A_b . . 104.3(19) ?
C1A_b N3A_b C2A_b . . 98.0(15) ?
O2A_b N4A_b O1A_b . . 126.(3) ?
O2A_b N4A_b C1A_b . . 118.(2) ?
O1A_b N4A_b C1A_b . . 116.(2) ?
O4A_b N5A_b O3A_b . . 125.(3) ?
O4A_b N5A_b C2A_b . . 117.(2) ?
O3A_b N5A_b C2A_b . . 118.(3) ?

####################################################################### 
# 
# 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_C6H12N6O4
_database_code_depnum_ccdc_archive 'CCDC 1031353'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C2 N5 O4, C4 H12 N'
_chemical_formula_sum            'C6 H12 N6 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         232.22

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.1515(3)
_cell_length_b                   17.1906(10)
_cell_length_c                   9.8599(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.6300(10)
_cell_angle_gamma                90
_cell_volume                     1041.57(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7015
_cell_measurement_theta_min      2.3699
_cell_measurement_theta_max      30.2519
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.122
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488

_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker TWINABS V2014/4'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
The crystal specimen consisted of two domains rotated by 180 degrees.
The domains were indexed using cell_now and the frames integrated
using both domains.
The structure was solved with the HKLF5 file generated by TWINABS.
The final refinement was carried out with the HKLF5 file.
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            3159
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         30.47
_diffrn_reflns_theta_full        30.47
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13

_refine_special_details          Twin

_reflns_number_total             3159
_reflns_number_gt                2867
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1120
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_number_reflns         3159
_refine_ls_number_parameters     184
_refine_ls_number_restraints     28
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.2829P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XS 2013/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XL 2014/6 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XL 2014/6 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C3 0.2023(4) 0.42712(9) 0.86891(18) 0.0415(4) Uani d . . . 1.0 . .
H H3A 0.2097 0.4541 0.9566 0.062 Uiso calc U . R 1.0 . .
H H3B 0.0524 0.4283 0.8308 0.062 Uiso calc U . R 1.0 . .
H H3C 0.2984 0.4531 0.8065 0.062 Uiso calc U . R 1.0 . .
C C4 0.2689(3) 0.30501(10) 0.75384(14) 0.0308(3) Uani d . . . 1.0 . .
H H4A 0.3207 0.2515 0.7666 0.046 Uiso calc U . R 1.0 . .
H H4B 0.3638 0.3326 0.6928 0.046 Uiso calc U . R 1.0 . .
H H4C 0.1199 0.3043 0.7141 0.046 Uiso calc U . R 1.0 . .
C C5 0.4957(3) 0.34277(11) 0.95365(18) 0.0353(4) Uani d . . . 1.0 . .
H H5A 0.5374 0.2885 0.9703 0.053 Uiso calc U . R 1.0 . .
H H5B 0.4978 0.371 1.04 0.053 Uiso calc U . R 1.0 . .
H H5C 0.5987 0.3669 0.8935 0.053 Uiso calc U . R 1.0 . .
C C6 0.1193(3) 0.30403(11) 0.97743(19) 0.0378(4) Uani d . . . 1.0 . .
H H6A 0.1149 0.331 1.0648 0.057 Uiso calc U . R 1.0 . .
H H6B 0.1699 0.2505 0.9923 0.057 Uiso calc U . R 1.0 . .
H H6C -0.0267 0.3033 0.9334 0.057 Uiso calc U . R 1.0 . .
N N6 0.27214(17) 0.34569(6) 0.88835(10) 0.0169(2) Uani d . . . 1.0 . .
C C1 0.7680(2) 0.39433(7) 0.42610(12) 0.0152(2) Uani d . P D 0.9602(11) A 1
C C2 0.74165(19) 0.46874(8) 0.58067(12) 0.0157(2) Uani d . P D 0.9602(11) A 1
N N1 0.7414(2) 0.39849(7) 0.63943(11) 0.0212(2) Uani d . P D 0.9602(11) A 1
N N2 0.7584(2) 0.34801(6) 0.53445(11) 0.0212(2) Uani d . P D 0.9602(11) A 1
N N3 0.75917(16) 0.47107(6) 0.44636(11) 0.01488(19) Uani d . P D 0.9602(11) A 1
N N4 0.7886(2) 0.36165(7) 0.29179(12) 0.0193(2) Uani d . P D 0.9602(11) A 1
N N5 0.72257(18) 0.53863(7) 0.66087(12) 0.0205(2) Uani d . P D 0.9602(11) A 1
O O1 0.83042(19) 0.40703(7) 0.19958(11) 0.0273(2) Uani d . P D 0.9602(11) A 1
O O2 0.7646(2) 0.29171(6) 0.27647(12) 0.0338(3) Uani d . P D 0.9602(11) A 1
O O3 0.73521(17) 0.60172(6) 0.60315(11) 0.0266(2) Uani d . P D 0.9602(11) A 1
O O4 0.6933(2) 0.53090(8) 0.78278(13) 0.0323(3) Uani d . P D 0.9602(11) A 1
C C1' 0.774(5) 0.4323(11) 0.4591(19) 0.0152(2) Uani d . P D 0.0398(11) A 2
C C2' 0.740(5) 0.5084(12) 0.6096(17) 0.0157(2) Uani d . P D 0.0398(11) A 2
N N1' 0.745(5) 0.5510(11) 0.4956(19) 0.0212(2) Uani d . P D 0.0398(11) A 2
N N2' 0.766(5) 0.4997(12) 0.395(2) 0.0212(2) Uani d . P D 0.0398(11) A 2
N N3' 0.759(4) 0.4324(13) 0.5966(19) 0.01488(19) Uani d . P D 0.0398(11) A 2
N N4' 0.797(5) 0.3630(11) 0.379(2) 0.0193(2) Uani d . P D 0.0398(11) A 2
N N5' 0.726(6) 0.5466(12) 0.740(2) 0.0205(2) Uani d . P D 0.0398(11) A 2
O O1' 0.832(5) 0.3018(12) 0.451(2) 0.0273(2) Uani d . P D 0.0398(11) A 2
O O2' 0.810(8) 0.376(2) 0.257(2) 0.0338(3) Uani d . P D 0.0398(11) A 2
O O3' 0.707(5) 0.5023(13) 0.836(2) 0.0266(2) Uani d . P D 0.0398(11) A 2
O O4' 0.699(5) 0.6167(12) 0.740(2) 0.0323(3) Uani d . P D 0.0398(11) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 N6 . 1.4741(18) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 N6 . 1.4986(16) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 N6 . 1.4923(18) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 N6 . 1.4979(18) ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C1 N3 . 1.3356(15) ?
C1 N2 . 1.3360(15) ?
C1 N4 . 1.4495(17) ?
C1 C2 . 2.0019(17) ?
C2 N3 . 1.3341(15) ?
C2 N1 . 1.3395(16) ?
C2 N5 . 1.4460(16) ?
N1 N2 . 1.3584(15) ?
N4 O2 . 1.2198(16) ?
N4 O1 . 1.2341(15) ?
N5 O3 . 1.2290(16) ?
N5 O4 . 1.2307(18) ?
C1' N2' . 1.319(17) ?
C1' N3' . 1.363(17) ?
C1' N4' . 1.440(16) ?
C1' C2' . 1.997(15) ?
C2' N3' . 1.318(17) ?
C2' N1' . 1.343(17) ?
C2' N5' . 1.452(16) ?
N1' N2' . 1.338(17) ?
N4' O2' . 1.225(18) ?
N4' O1' . 1.282(17) ?
N5' O4' . 1.218(17) ?
N5' O3' . 1.223(17) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N6 C3 H3A . . 109.5 ?
N6 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
N6 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N6 C4 H4A . . 109.5 ?
N6 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N6 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N6 C5 H5A . . 109.5 ?
N6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N6 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N6 C6 H6A . . 109.5 ?
N6 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
N6 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C3 N6 C5 . . 110.20(12) ?
C3 N6 C6 . . 110.08(14) ?
C5 N6 C6 . . 108.75(12) ?
C3 N6 C4 . . 109.63(11) ?
C5 N6 C4 . . 109.93(11) ?
C6 N6 C4 . . 108.21(12) ?
N3 C1 N2 . . 117.75(12) ?
N3 C1 N4 . . 121.69(11) ?
N2 C1 N4 . . 120.56(11) ?
N3 C1 C2 . . 41.39(7) ?
N2 C1 C2 . . 76.35(8) ?
N4 C1 C2 . . 163.09(10) ?
N3 C2 N1 . . 117.26(12) ?
N3 C2 N5 . . 122.02(12) ?
N1 C2 N5 . . 120.72(11) ?
N3 C2 C1 . . 41.45(7) ?
N1 C2 C1 . . 75.81(8) ?
N5 C2 C1 . . 163.46(10) ?
C2 N1 N2 . . 104.17(10) ?
C1 N2 N1 . . 103.66(10) ?
C2 N3 C1 . . 97.16(11) ?
O2 N4 O1 . . 124.06(13) ?
O2 N4 C1 . . 118.69(11) ?
O1 N4 C1 . . 117.25(11) ?
O3 N5 O4 . . 124.24(13) ?
O3 N5 C2 . . 118.13(11) ?
O4 N5 C2 . . 117.62(12) ?
N2' C1' N3' . . 118.2(14) ?
N2' C1' N4' . . 117.8(15) ?
N3' C1' N4' . . 124.1(17) ?
N2' C1' C2' . . 77.2(10) ?
N3' C1' C2' . . 41.0(8) ?
N4' C1' C2' . . 165.1(15) ?
N3' C2' N1' . . 116.9(14) ?
N3' C2' N5' . . 122.9(16) ?
N1' C2' N5' . . 120.1(16) ?
N3' C2' C1' . . 42.7(8) ?
N1' C2' C1' . . 74.2(10) ?
N5' C2' C1' . . 165.5(16) ?
N2' N1' C2' . . 105.6(15) ?
C1' N2' N1' . . 103.1(15) ?
C2' N3' C1' . . 96.2(13) ?
O2' N4' O1' . . 132.(2) ?
O2' N4' C1' . . 114.(2) ?
O1' N4' C1' . . 113.2(18) ?
O4' N5' O3' . . 127.(2) ?
O4' N5' C2' . . 117.3(19) ?
O3' N5' C2' . . 114.6(19) ?

