# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_0677_040215_mh_aminebpy_0m
_database_code_depnum_ccdc_archive 'CCDC 1427785'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3'
_chemical_formula_sum            'C10 H9 N3'
_chemical_formula_weight         171.20
_chemical_absolute_configuration rm

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'I4(1)/a  '
_symmetry_space_group_name_HALL  '-I 4ad'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   23.5825(14)
_cell_length_b                   23.5825(14)
_cell_length_c                   6.2166(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3457.3(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3236
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.315
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6425
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1524
_reflns_number_gt                1271
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 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     
'calc w=1/[σ²(Fo²)+(0.0695P)²+1.6636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1524
_refine_ls_number_parameters     126
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.145
_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
C1 C 0.66819(7) 0.27741(7) -0.2457(3) 0.0404(4) Uani 1 1 d . . .
C2 C 0.64398(8) 0.27531(8) -0.4492(3) 0.0499(5) Uani 1 1 d . . .
H2 H 0.6538 0.3020 -0.5529 0.060 Uiso 1 1 calc R . .
C3 C 0.60539(9) 0.23346(8) -0.4958(3) 0.0602(6) Uani 1 1 d . . .
H3 H 0.5886 0.2315 -0.6310 0.072 Uiso 1 1 calc R . .
C4 C 0.59200(9) 0.19465(9) -0.3405(4) 0.0620(6) Uani 1 1 d . . .
H4 H 0.5658 0.1660 -0.3670 0.074 Uiso 1 1 calc R . .
C5 C 0.61821(9) 0.19912(9) -0.1449(3) 0.0625(6) Uani 1 1 d . . .
H5 H 0.6091 0.1725 -0.0401 0.075 Uiso 1 1 calc R . .
C6 C 0.70935(7) 0.32267(7) -0.1877(3) 0.0401(4) Uani 1 1 d . . .
C7 C 0.73965(7) 0.32038(7) 0.0016(3) 0.0431(4) Uani 1 1 d . . .
H7 H 0.7338 0.2906 0.0970 0.052 Uiso 1 1 calc R . .
C8 C 0.77912(7) 0.36270(7) 0.0508(3) 0.0461(5) Uani 1 1 d . . .
C9 C 0.78579(8) 0.40567(8) -0.1012(3) 0.0532(5) Uani 1 1 d . . .
H9 H 0.8121 0.4345 -0.0797 0.064 Uiso 1 1 calc R . .
C10 C 0.75295(8) 0.40473(8) -0.2826(3) 0.0563(5) Uani 1 1 d . . .
H10 H 0.7577 0.4342 -0.3803 0.068 Uiso 1 1 calc R . .
N1 N 0.65601(7) 0.23920(7) -0.0941(2) 0.0523(4) Uani 1 1 d . . .
N2 N 0.71462(6) 0.36501(6) -0.3314(3) 0.0509(4) Uani 1 1 d . . .
N3 N 0.80945(8) 0.36187(8) 0.2362(3) 0.0629(5) Uani 1 1 d D . .
H3' H 0.8376(9) 0.3913(8) 0.277(4) 0.093(8) Uiso 1 1 d D . .
H3'' H 0.8040(13) 0.3306(9) 0.343(4) 0.113(10) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.335(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.487(2) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.337(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.345(2) . ?
C6 C7 1.378(2) . ?
C7 C8 1.398(2) . ?
C7 H7 0.9300 . ?
C8 N3 1.357(2) . ?
C8 C9 1.394(3) . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.336(2) . ?
C10 H10 0.9300 . ?
N3 H3' 0.994(10) . ?
N3 H3'' 0.999(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.04(16) . . ?
N1 C1 C6 116.96(15) . . ?
C2 C1 C6 120.99(15) . . ?
C3 C2 C1 119.35(17) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 119.02(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 118.14(19) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 124.44(18) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N2 C6 C7 123.23(16) . . ?
N2 C6 C1 115.60(15) . . ?
C7 C6 C1 121.17(15) . . ?
C6 C7 C8 120.26(16) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N3 C8 C9 121.79(17) . . ?
N3 C8 C7 121.76(17) . . ?
C9 C8 C7 116.45(17) . . ?
C10 C9 C8 118.88(17) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 125.52(18) . . ?
N2 C10 H10 117.2 . . ?
C9 C10 H10 117.2 . . ?
C1 N1 C5 116.98(16) . . ?
C10 N2 C6 115.62(16) . . ?
C8 N3 H3' 124.0(16) . . ?
C8 N3 H3'' 120.4(18) . . ?
H3' N3 H3'' 116(2) . . ?

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
N1 C1 C2 C3 1.4(3) . . . . ?
C6 C1 C2 C3 -178.90(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
N1 C1 C6 N2 -170.77(15) . . . . ?
C2 C1 C6 N2 9.5(2) . . . . ?
N1 C1 C6 C7 9.3(2) . . . . ?
C2 C1 C6 C7 -170.43(16) . . . . ?
N2 C6 C7 C8 -1.4(3) . . . . ?
C1 C6 C7 C8 178.52(14) . . . . ?
C6 C7 C8 N3 179.69(16) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
N3 C8 C9 C10 -178.51(18) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C8 C9 C10 N2 -1.1(3) . . . . ?
C2 C1 N1 C5 -1.5(3) . . . . ?
C6 C1 N1 C5 178.81(16) . . . . ?
C4 C5 N1 C1 0.6(3) . . . . ?
C9 C10 N2 C6 -0.7(3) . . . . ?
C7 C6 N2 C10 2.0(2) . . . . ?
C1 C6 N2 C10 -177.91(15) . . . . ?

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
N3 H3' N2 0.994(10) 2.239(12) 3.214(2) 167(2) 2_645
N3 H3'' N1 0.999(10) 2.459(18) 3.361(2) 150(2) 13_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1427786'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3'
_chemical_formula_sum            'C10 H9 N3'
_chemical_formula_weight         171.20
_chemical_absolute_configuration rm

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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
'x-1/2, y-1/2, -z'

_cell_length_a                   15.2009(19)
_cell_length_b                   9.7035(11)
_cell_length_c                   12.0827(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1782.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2992
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.275
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            7863
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.490
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1824
_reflns_number_gt                1284
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0745P)²+0.4260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1824
_refine_ls_number_parameters     126
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1630
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
C1 C 0.28736(14) 0.5803(2) 0.7597(2) 0.0745(6) Uani 1 1 d . . . . .
H1 H 0.3054 0.6218 0.8252 0.089 Uiso 1 1 calc R U . . .
C2 C 0.32822(16) 0.6189(3) 0.6639(2) 0.0868(8) Uani 1 1 d . . . . .
H2 H 0.3726 0.6848 0.6647 0.104 Uiso 1 1 calc R U . . .
C3 C 0.30228(15) 0.5582(3) 0.5664(2) 0.0874(7) Uani 1 1 d . . . . .
H3 H 0.3288 0.5822 0.4998 0.105 Uiso 1 1 calc R U . . .
C4 C 0.23664(13) 0.4615(2) 0.56933(17) 0.0702(6) Uani 1 1 d . . . . .
H4 H 0.2181 0.4186 0.5045 0.084 Uiso 1 1 calc R U . . .
C5 C 0.19812(11) 0.42821(19) 0.66969(14) 0.0533(5) Uani 1 1 d . . . . .
C6 C 0.12763(11) 0.32260(18) 0.67627(13) 0.0509(4) Uani 1 1 d . . . . .
C7 C 0.10842(12) 0.25679(18) 0.77402(14) 0.0531(5) Uani 1 1 d . . . . .
H7 H 0.1386 0.2801 0.8383 0.064 Uiso 1 1 calc R U . . .
C8 C 0.04376(13) 0.15513(19) 0.77701(14) 0.0578(5) Uani 1 1 d . . . . .
C9 C -0.00084(14) 0.1273(2) 0.67834(16) 0.0689(6) Uani 1 1 d . . . . .
H9 H -0.0451 0.0612 0.6759 0.083 Uiso 1 1 calc R U . . .
C10 C 0.02193(15) 0.1991(2) 0.58594(17) 0.0742(6) Uani 1 1 d . . . . .
H10 H -0.0084 0.1792 0.5210 0.089 Uiso 1 1 calc R U . . .
N1 N 0.22304(10) 0.48676(16) 0.76521(13) 0.0622(5) Uani 1 1 d . . . . .
N2 N 0.08459(11) 0.29601(18) 0.58102(12) 0.0655(5) Uani 1 1 d . . . . .
N3 N 0.02550(15) 0.0862(2) 0.87073(15) 0.0824(6) Uani 1 1 d D . . . .
H3' H 0.0522(15) 0.119(2) 0.9381(15) 0.096(8) Uiso 1 1 d D . . . .
H3'' H -0.0175(15) 0.014(2) 0.869(2) 0.110(9) Uiso 1 1 d 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
C1 N1 1.336(3) . ?
C1 C2 1.365(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.341(2) . ?
C5 C6 1.485(3) . ?
C6 N2 1.349(2) . ?
C6 C7 1.374(2) . ?
C7 C8 1.393(3) . ?
C7 H7 0.9300 . ?
C8 N3 1.344(2) . ?
C8 C9 1.398(3) . ?
C9 C10 1.360(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.340(3) . ?
C10 H10 0.9300 . ?
N3 H3' 0.964(15) . ?
N3 H3'' 0.959(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
N1 C1 C2 124.2(2) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 118.6(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.37(18) . . ?
N1 C5 C6 116.76(15) . . ?
C4 C5 C6 120.86(17) . . ?
N2 C6 C7 122.78(17) . . ?
N2 C6 C5 115.88(15) . . ?
C7 C6 C5 121.34(15) . . ?
C6 C7 C8 120.09(16) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
N3 C8 C7 121.33(17) . . ?
N3 C8 C9 121.49(19) . . ?
C7 C8 C9 117.18(17) . . ?
C10 C9 C8 118.54(19) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N2 C10 C9 125.21(18) . . ?
N2 C10 H10 117.4 . . ?
C9 C10 H10 117.4 . . ?
C1 N1 C5 116.84(18) . . ?
C10 N2 C6 116.18(16) . . ?
C8 N3 H3' 117.3(14) . . ?
C8 N3 H3'' 119.4(15) . . ?
H3' N3 H3'' 123.0(18) . . ?

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
N3 H3' N2 0.964(15) 1.975(16) 2.927(2) 169(2) 7_566
N3 H3'' N2 0.959(16) 2.423(19) 3.327(3) 157(2) 3_546

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1427788'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3'
_chemical_formula_sum            'C10 H9 N3'
_chemical_formula_weight         171.20
_chemical_absolute_configuration rm

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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_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-y, x, z+5/6'
'y, -x+y, z+1/6'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'

_cell_length_a                   18.260(2)
_cell_length_b                   18.260(2)
_cell_length_c                   5.0477(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1457.5(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1317
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      20.32

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.169
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9820
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            7578
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.288
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             1839
_reflns_number_gt                1214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.906
_reflns_Friedel_fraction_full    0.919

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0940P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 421 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(10)
_refine_ls_number_reflns         1839
_refine_ls_number_parameters     120
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1777
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.004
_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
C1 C 0.6621(4) -0.0166(3) 0.5281(11) 0.0679(16) Uani 1 1 d . . . . .
H1 H 0.6197 -0.0705 0.5762 0.081 Uiso 1 1 calc R U . . .
C2 C 0.7362(4) 0.0163(4) 0.6568(13) 0.0752(17) Uani 1 1 d . . . . .
H2 H 0.7447 -0.0138 0.7902 0.090 Uiso 1 1 calc R U . . .
C3 C 0.7978(4) 0.0943(4) 0.5869(13) 0.087(2) Uani 1 1 d . . . . .
H3 H 0.8499 0.1188 0.6721 0.104 Uiso 1 1 calc R U . . .
C4 C 0.7837(4) 0.1373(3) 0.3908(12) 0.0694(15) Uani 1 1 d . . . . .
H4 H 0.8262 0.1909 0.3411 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7063(3) 0.1007(3) 0.2673(9) 0.0482(12) Uani 1 1 d . . . . .
C6 C 0.6875(3) 0.1457(2) 0.0584(10) 0.0463(12) Uani 1 1 d . . . . .
C7 C 0.6097(3) 0.1097(3) -0.0657(9) 0.0474(12) Uani 1 1 d . . . . .
H7 H 0.5675 0.0560 -0.0155 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5932(3) 0.1522(3) -0.2637(9) 0.0437(11) Uani 1 1 d . . . . .
C9 C 0.6599(3) 0.2316(3) -0.3297(10) 0.0501(12) Uani 1 1 d . . . . .
H9 H 0.6537 0.2630 -0.4638 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7342(3) 0.2630(3) -0.1969(11) 0.0571(14) Uani 1 1 d . . . . .
H10 H 0.7771 0.3167 -0.2442 0.069 Uiso 1 1 calc R U . . .
N1 N 0.7511(2) 0.2236(2) -0.0045(8) 0.0549(11) Uani 1 1 d . . . . .
N2 N 0.6451(2) 0.0234(2) 0.3328(8) 0.0553(11) Uani 1 1 d . . . . .
N3 N 0.5170(3) 0.1195(2) -0.3860(9) 0.0587(12) Uani 1 1 d D . . . .
H3' H 0.5016 0.1536 -0.4744 0.088(19) Uiso 1 1 d D . . . .
H3'' H 0.4773 0.0773 -0.2861 0.10(2) Uiso 1 1 d 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
C1 C2 1.342(7) . ?
C1 N2 1.353(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(7) . ?
C4 H4 0.9300 . ?
C5 N2 1.332(6) . ?
C5 C6 1.479(6) . ?
C6 N1 1.351(5) . ?
C6 C7 1.381(6) . ?
C7 C8 1.387(6) . ?
C7 H7 0.9300 . ?
C8 N3 1.358(6) . ?
C8 C9 1.390(6) . ?
C9 C10 1.356(7) . ?
C9 H9 0.9300 . ?
C10 N1 1.334(6) . ?
C10 H10 0.9300 . ?
N3 H3' 0.916(4) . ?
N3 H3'' 0.903(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N2 124.3(5) . . ?
C2 C1 H1 117.9 . . ?
N2 C1 H1 117.9 . . ?
C1 C2 C3 117.9(6) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N2 C5 C4 121.1(5) . . ?
N2 C5 C6 117.4(4) . . ?
C4 C5 C6 121.5(4) . . ?
N1 C6 C7 122.2(4) . . ?
N1 C6 C5 115.9(4) . . ?
C7 C6 C5 121.9(4) . . ?
C6 C7 C8 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
N3 C8 C7 123.0(4) . . ?
N3 C8 C9 121.3(4) . . ?
C7 C8 C9 115.7(4) . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N1 C10 C9 125.8(4) . . ?
N1 C10 H10 117.1 . . ?
C9 C10 H10 117.1 . . ?
C10 N1 C6 115.4(4) . . ?
C5 N2 C1 117.1(4) . . ?
C8 N3 H3' 121.2(4) . . ?
C8 N3 H3'' 109.2(4) . . ?
H3' N3 H3'' 117.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 -0.2(9) . . . . ?
C1 C2 C3 C4 0.1(9) . . . . ?
C2 C3 C4 C5 0.4(9) . . . . ?
C3 C4 C5 N2 -1.0(8) . . . . ?
C3 C4 C5 C6 178.5(5) . . . . ?
N2 C5 C6 N1 -179.5(4) . . . . ?
C4 C5 C6 N1 0.9(6) . . . . ?
N2 C5 C6 C7 0.0(6) . . . . ?
C4 C5 C6 C7 -179.6(5) . . . . ?
N1 C6 C7 C8 0.3(7) . . . . ?
C5 C6 C7 C8 -179.2(4) . . . . ?
C6 C7 C8 N3 -178.5(4) . . . . ?
C6 C7 C8 C9 0.9(6) . . . . ?
N3 C8 C9 C10 177.9(4) . . . . ?
C7 C8 C9 C10 -1.6(6) . . . . ?
C8 C9 C10 N1 1.1(7) . . . . ?
C9 C10 N1 C6 0.2(7) . . . . ?
C7 C6 N1 C10 -0.9(6) . . . . ?
C5 C6 N1 C10 178.7(4) . . . . ?
C4 C5 N2 C1 0.9(6) . . . . ?
C6 C5 N2 C1 -178.6(4) . . . . ?
C2 C1 N2 C5 -0.4(7) . . . . ?

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
N3 H3' N1 0.916(4) 2.284(4) 3.197(5) 174.6(3) 5_664
N3 H3'' N2 0.903(4) 2.151(4) 3.011(6) 158.9(3) 6_654
N3 H3' N1 0.916(4) 2.284(4) 3.197(5) 174.6(3) 5_664
N3 H3'' N2 0.903(4) 2.151(4) 3.011(6) 158.9(3) 6_654

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-3




