# 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_jx203
_database_code_depnum_ccdc_archive 'CCDC 1406925'

_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-97
_audit_creation_date             
;
'Mon Jun 30 10:27:59 2014'
;

_chemical_name_systematic        4-Amino-1-benzyl-1,2,3-triazol-5-amide
_chemical_compound_source        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H11 N5 O'
_chemical_formula_sum            'C10 H11 N5 O'
_chemical_formula_weight         217.227

_diffrn_ambient_temperature      173(2)
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ?
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            6884
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         26.37
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996

_reflns_number_total             1980
_reflns_number_gt                1738
_reflns_threshold_expression     >2σ(I)

_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?
_diffrn_measurement_details      ?
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.731(4)
_cell_length_b                   7.423(2)
_cell_length_c                   11.188(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.655(3)
_cell_angle_gamma                90.00
_cell_volume                     972.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3097
_cell_measurement_theta_min      4.4190
_cell_measurement_theta_max      32.1980
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2669
_exptl_crystal_size_mid          0.1266
_exptl_crystal_size_min          0.1172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96986
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0347P)²+0.2924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1980
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N 0.46432(9) 1.33291(16) 0.62969(11) 0.0271(3) Uani 1 1 d . . .
O1 O 0.42615(7) 1.30466(11) 0.42869(8) 0.0257(2) Uani 1 1 d . . .
N1 N 0.29663(8) 0.80343(13) 0.52301(9) 0.0179(2) Uani 1 1 d . . .
N2 N 0.32087(9) 0.82578(14) 0.64403(9) 0.0234(2) Uani 1 1 d . . .
N3 N 0.36703(8) 0.98454(14) 0.65923(9) 0.0228(2) Uani 1 1 d . . .
C3 C 0.42367(9) 1.24309(15) 0.53154(11) 0.0201(3) Uani 1 1 d . . .
N5 N 0.31186(9) 0.96995(15) 0.34241(9) 0.0226(2) Uani 1 1 d . . .
C1 C 0.37356(9) 1.06566(15) 0.55064(10) 0.0183(2) Uani 1 1 d . . .
C2 C 0.32821(9) 0.94956(15) 0.46225(10) 0.0160(2) Uani 1 1 d . . .
C4 C 0.24396(10) 0.63777(16) 0.47531(12) 0.0219(3) Uani 1 1 d . . .
C5 C 0.12050(10) 0.66243(15) 0.43012(11) 0.0190(3) Uani 1 1 d . . .
C10 C 0.04516(10) 0.75753(17) 0.49658(12) 0.0243(3) Uani 1 1 d . . .
C9 C -0.06899(11) 0.77210(18) 0.45668(13) 0.0281(3) Uani 1 1 d . . .
C8 C -0.10816(11) 0.69009(17) 0.35077(12) 0.0265(3) Uani 1 1 d . . .
C7 C -0.03363(11) 0.59242(18) 0.28531(12) 0.0284(3) Uani 1 1 d . . .
C6 C 0.08080(11) 0.58057(17) 0.32427(12) 0.0254(3) Uani 1 1 d . . .
H3 H 0.3496(13) 1.062(2) 0.3139(14) 0.035(4) Uiso 1 1 d . . .
H4 H 0.3041(13) 0.872(2) 0.2933(15) 0.037(4) Uiso 1 1 d . . .
H4A H 0.2509(11) 0.552(2) 0.5430(13) 0.025(4) Uiso 1 1 d . . .
H4B H 0.2893(12) 0.5946(19) 0.4102(13) 0.027(4) Uiso 1 1 d . . .
H8A H -0.1894(12) 0.7033(19) 0.3220(13) 0.028(4) Uiso 1 1 d . . .
H6A H 0.1355(13) 0.514(2) 0.2791(14) 0.035(4) Uiso 1 1 d . . .
H7A H -0.0610(13) 0.531(2) 0.2116(15) 0.037(4) Uiso 1 1 d . . .
H9A H -0.1228(13) 0.837(2) 0.5050(14) 0.033(4) Uiso 1 1 d . . .
H10A H 0.0716(12) 0.815(2) 0.5709(14) 0.029(4) Uiso 1 1 d . . .
H2 H 0.5005(14) 1.439(3) 0.6202(15) 0.045(5) Uiso 1 1 d . . .
H1 H 0.4691(13) 1.277(2) 0.6987(15) 0.031(4) Uiso 1 1 d . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 C3 1.3458(16) . ?
N4 H2 0.902(19) . ?
N4 H1 0.876(17) . ?
O1 C3 1.2402(16) . ?
N1 C2 1.3447(16) . ?
N1 N2 1.3757(15) . ?
N1 C4 1.4617(16) . ?
N2 N3 1.3036(16) . ?
N3 C1 1.3625(16) . ?
C3 C1 1.4635(18) . ?
N5 C2 1.3508(16) . ?
N5 H3 0.882(17) . ?
N5 H4 0.911(17) . ?
C1 C2 1.3916(16) . ?
C4 C5 1.5144(17) . ?
C4 H4A 0.988(15) . ?
C4 H4B 0.983(15) . ?
C5 C10 1.3843(17) . ?
C5 C6 1.3851(18) . ?
C10 C9 1.3885(19) . ?
C10 H10A 0.967(15) . ?
C9 C8 1.384(2) . ?
C9 H9A 0.984(16) . ?
C8 C7 1.381(2) . ?
C8 H8A 0.991(14) . ?
C7 C6 1.3875(19) . ?
C7 H7A 0.979(16) . ?
C6 H6A 0.975(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N4 H2 118.7(11) . . ?
C3 N4 H1 118.9(10) . . ?
H2 N4 H1 120.9(14) . . ?
C2 N1 N2 110.73(9) . . ?
C2 N1 C4 128.15(10) . . ?
N2 N1 C4 121.12(10) . . ?
N3 N2 N1 107.19(9) . . ?
N2 N3 C1 109.25(10) . . ?
O1 C3 N4 123.13(12) . . ?
O1 C3 C1 120.03(11) . . ?
N4 C3 C1 116.84(12) . . ?
C2 N5 H3 113.7(10) . . ?
C2 N5 H4 120.8(10) . . ?
H3 N5 H4 115.4(15) . . ?
N3 C1 C2 108.62(11) . . ?
N3 C1 C3 125.02(11) . . ?
C2 C1 C3 126.33(11) . . ?
N1 C2 N5 124.47(11) . . ?
N1 C2 C1 104.21(11) . . ?
N5 C2 C1 131.27(11) . . ?
N1 C4 C5 113.15(10) . . ?
N1 C4 H4A 104.4(8) . . ?
C5 C4 H4A 111.4(8) . . ?
N1 C4 H4B 108.0(8) . . ?
C5 C4 H4B 110.1(8) . . ?
H4A C4 H4B 109.7(12) . . ?
C10 C5 C6 119.45(11) . . ?
C10 C5 C4 120.80(11) . . ?
C6 C5 C4 119.65(11) . . ?
C5 C10 C9 120.18(12) . . ?
C5 C10 H10A 120.4(9) . . ?
C9 C10 H10A 119.5(8) . . ?
C8 C9 C10 120.11(12) . . ?
C8 C9 H9A 119.8(9) . . ?
C10 C9 H9A 120.1(9) . . ?
C7 C8 C9 119.86(12) . . ?
C7 C8 H8A 120.5(8) . . ?
C9 C8 H8A 119.6(8) . . ?
C8 C7 C6 119.94(12) . . ?
C8 C7 H7A 120.4(9) . . ?
C6 C7 H7A 119.6(9) . . ?
C5 C6 C7 120.44(12) . . ?
C5 C6 H6A 117.9(9) . . ?
C7 C6 H6A 121.7(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 N3 0.12(12) . . . . ?
C4 N1 N2 N3 179.88(10) . . . . ?
N1 N2 N3 C1 -0.15(12) . . . . ?
N2 N3 C1 C2 0.12(13) . . . . ?
N2 N3 C1 C3 -178.04(10) . . . . ?
O1 C3 C1 N3 179.50(10) . . . . ?
N4 C3 C1 N3 -1.21(16) . . . . ?
O1 C3 C1 C2 1.66(17) . . . . ?
N4 C3 C1 C2 -179.06(11) . . . . ?
N2 N1 C2 N5 -177.71(10) . . . . ?
C4 N1 C2 N5 2.55(18) . . . . ?
N2 N1 C2 C1 -0.04(12) . . . . ?
C4 N1 C2 C1 -179.78(10) . . . . ?
N3 C1 C2 N1 -0.05(12) . . . . ?
C3 C1 C2 N1 178.09(10) . . . . ?
N3 C1 C2 N5 177.39(11) . . . . ?
C3 C1 C2 N5 -4.47(19) . . . . ?
C2 N1 C4 C5 -72.22(15) . . . . ?
N2 N1 C4 C5 108.07(12) . . . . ?
N1 C4 C5 C10 -45.16(15) . . . . ?
N1 C4 C5 C6 138.45(12) . . . . ?
C6 C5 C10 C9 -0.65(18) . . . . ?
C4 C5 C10 C9 -177.05(11) . . . . ?
C5 C10 C9 C8 0.6(2) . . . . ?
C10 C9 C8 C7 0.5(2) . . . . ?
C9 C8 C7 C6 -1.62(19) . . . . ?
C10 C5 C6 C7 -0.44(18) . . . . ?
C4 C5 C6 C7 176.00(11) . . . . ?
C8 C7 C6 C5 1.59(19) . . . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
? ? ? ? ? ? ? ?

_geom_special_details            ?



####################################################################### 
# 
# 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_tv197
_database_code_depnum_ccdc_archive 'CCDC 1413469'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_audit_creation_date             '07/15/15 07:57:42'
_audit_creation_method           SHELXL-2013

_chemical_name_systematic        
5-(5-amino-2H-1,2,3-triazol-4-yl)-1H-tetrazole
_chemical_name_common            
5-(5-amino-2H-1,2,3-triazol-4-yl)-1H-tetrazole
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H4 N8'
_chemical_formula_sum            'C3 H4 N8'
_chemical_formula_weight         152.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   6.9019(4)
_cell_length_b                   11.6423(7)
_cell_length_c                   8.0685(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.881(2)
_cell_angle_gamma                90
_cell_volume                     592.83(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3427
_cell_measurement_theta_min      3.2690
_cell_measurement_theta_max      26.3752

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8459
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode generator'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            6279
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.269
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1218
_reflns_number_gt                1057
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.1852P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1218
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N7 N 0.24801(16) 0.03570(10) -0.16296(14) 0.0169(3) Uani 1 1 d . . . . .
N3 N 0.25071(16) 0.09457(9) 0.28480(14) 0.0158(3) Uani 1 1 d . . . . .
N6 N 0.23080(17) 0.11754(10) -0.28764(14) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.26053(16) -0.09551(9) 0.34183(14) 0.0155(3) Uani 1 1 d . . . . .
N5 N 0.22121(17) 0.21978(10) -0.22718(14) 0.0174(3) Uani 1 1 d . . . . .
N8 N 0.2615(2) -0.16925(10) 0.06762(17) 0.0196(3) Uani 1 1 d . . . . .
N4 N 0.23178(17) 0.20533(10) -0.05844(14) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.25393(17) 0.01305(9) 0.39805(15) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.26043(19) -0.08160(11) 0.17600(17) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.24763(18) 0.09289(11) -0.02090(17) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.25537(18) 0.03778(11) 0.14177(16) 0.0146(3) Uani 1 1 d . . . . .
H1 H 0.248(2) 0.0309(16) 0.504(2) 0.028(5) Uiso 1 1 d . . . . .
H4 H 0.261(3) -0.1543(15) -0.040(3) 0.027(4) Uiso 1 1 d . . . . .
H3 H 0.263(3) -0.2404(17) 0.108(2) 0.023(4) Uiso 1 1 d . . . . .
H2 H 0.230(3) 0.268(2) 0.009(3) 0.040(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N7 C3 1.3264(16) . ?
N7 N6 1.3554(15) . ?
N3 N2 1.3114(15) . ?
N3 C1 1.3416(16) . ?
N6 N5 1.2981(16) . ?
N1 C2 1.3474(17) . ?
N1 N2 1.3499(16) . ?
N5 N4 1.3442(15) . ?
N8 C2 1.3458(17) . ?
N8 H4 0.89(2) . ?
N8 H3 0.89(2) . ?
N4 C3 1.3382(18) . ?
N4 H2 0.91(2) . ?
N2 H1 0.901(18) . ?
C2 C1 1.4147(19) . ?
C3 C1 1.4424(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N7 N6 104.97(11) . . ?
N2 N3 C1 104.07(10) . . ?
N5 N6 N7 111.60(10) . . ?
C2 N1 N2 103.57(10) . . ?
N6 N5 N4 106.01(10) . . ?
C2 N8 H4 119.4(11) . . ?
C2 N8 H3 118.0(11) . . ?
H4 N8 H3 122.6(15) . . ?
C3 N4 N5 108.52(11) . . ?
C3 N4 H2 131.7(13) . . ?
N5 N4 H2 119.8(13) . . ?
N3 N2 N1 115.90(10) . . ?
N3 N2 H1 120.2(12) . . ?
N1 N2 H1 123.9(12) . . ?
N8 C2 N1 123.79(12) . . ?
N8 C2 C1 128.62(12) . . ?
N1 C2 C1 107.58(11) . . ?
N7 C3 N4 108.90(12) . . ?
N7 C3 C1 123.42(12) . . ?
N4 C3 C1 127.64(12) . . ?
N3 C1 C2 108.87(11) . . ?
N3 C1 C3 123.96(12) . . ?
C2 C1 C3 127.13(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N7 N6 N5 0.28(13) . . . . ?
N7 N6 N5 N4 -0.16(13) . . . . ?
N6 N5 N4 C3 -0.03(13) . . . . ?
C1 N3 N2 N1 0.01(13) . . . . ?
C2 N1 N2 N3 -0.33(14) . . . . ?
N2 N1 C2 N8 -178.54(12) . . . . ?
N2 N1 C2 C1 0.48(13) . . . . ?
N6 N7 C3 N4 -0.29(13) . . . . ?
N6 N7 C3 C1 177.61(11) . . . . ?
N5 N4 C3 N7 0.21(14) . . . . ?
N5 N4 C3 C1 -177.57(11) . . . . ?
N2 N3 C1 C2 0.30(13) . . . . ?
N2 N3 C1 C3 178.05(11) . . . . ?
N8 C2 C1 N3 178.45(12) . . . . ?
N1 C2 C1 N3 -0.51(14) . . . . ?
N8 C2 C1 C3 0.8(2) . . . . ?
N1 C2 C1 C3 -178.17(11) . . . . ?
N7 C3 C1 N3 -178.58(11) . . . . ?
N4 C3 C1 N3 -1.10(19) . . . . ?
N7 C3 C1 C2 -1.25(19) . . . . ?
N4 C3 C1 C2 176.23(12) . . . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
