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

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

data_sadp21c
_database_code_depnum_ccdc_archive 'CCDC 1489603'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 N4'
_chemical_formula_weight         234.26

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                   9.3816(4)
_cell_length_b                   6.7781(3)
_cell_length_c                   16.9307(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.5145(11)
_cell_angle_gamma                90
_cell_volume                     1061.80(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8735
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      30.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.093
_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  0.6983
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Photon 100 CMOS-detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16254
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         30.108
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3118
_reflns_number_gt                2477
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_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)+(0.0846P)²+0.2564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3118
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
N1 N 0.18567(11) 0.24294(15) 0.64000(6) 0.0153(2) Uani 1 1 d . . . . .
C11 C 0.11558(14) 0.19351(19) 0.70794(7) 0.0196(3) Uani 1 1 d . . . . .
H11A H 0.0435 0.2945 0.7141 0.029 Uiso 1 1 calc R U . . .
H11B H 0.1881 0.1878 0.7567 0.029 Uiso 1 1 calc R U . . .
H11C H 0.0679 0.0650 0.6988 0.029 Uiso 1 1 calc R U . . .
C2 C 0.33036(13) 0.27164(18) 0.64542(7) 0.0179(3) Uani 1 1 d . . . . .
H2 H 0.3957 0.2665 0.6946 0.021 Uiso 1 1 calc R U . . .
N3 N 0.37153(11) 0.30724(15) 0.57618(6) 0.0177(2) Uani 1 1 d . . . . .
C4 C 0.24422(12) 0.30029(16) 0.52221(7) 0.0139(2) Uani 1 1 d . . . . .
C5 C 0.12765(12) 0.25959(16) 0.56011(7) 0.0131(2) Uani 1 1 d . . . . .
C1* C 0.08696(12) 0.30236(16) 0.39235(7) 0.0130(2) Uani 1 1 d . . . . .
N1* N 0.06127(11) 0.32296(16) 0.31147(6) 0.0175(2) Uani 1 1 d . . . . .
C2* C 0.17154(14) 0.3736(2) 0.27582(7) 0.0205(3) Uani 1 1 d . . . . .
H2* H 0.1540 0.3876 0.2192 0.025 Uiso 1 1 calc R U . . .
C3* C 0.31171(13) 0.40775(19) 0.31602(7) 0.0206(3) Uani 1 1 d . . . . .
H3* H 0.3860 0.4475 0.2875 0.025 Uiso 1 1 calc R U . . .
C4* C 0.34012(12) 0.38273(18) 0.39760(7) 0.0179(3) Uani 1 1 d . . . . .
H4* H 0.4348 0.4028 0.4265 0.022 Uiso 1 1 calc R U . . .
C5* C 0.22647(12) 0.32687(17) 0.43748(7) 0.0138(2) Uani 1 1 d . . . . .
C6* C -0.01678(12) 0.23954(16) 0.51754(7) 0.0125(2) Uani 1 1 d . . . . .
C7* C -0.14045(12) 0.20250(17) 0.55231(7) 0.0151(2) Uani 1 1 d . . . . .
H7* H -0.1324 0.1906 0.6088 0.018 Uiso 1 1 calc R U . . .
C8* C -0.27284(12) 0.18359(18) 0.50414(7) 0.0171(2) Uani 1 1 d . . . . .
H8* H -0.3575 0.1593 0.5266 0.020 Uiso 1 1 calc R U . . .
C9* C -0.27988(12) 0.20091(17) 0.42137(7) 0.0162(2) Uani 1 1 d . . . . .
H9* H -0.3715 0.1855 0.3884 0.019 Uiso 1 1 calc R U . . .
N10* N -0.16697(10) 0.23742(14) 0.38593(6) 0.0150(2) Uani 1 1 d . . . . .
C10* C -0.03615(12) 0.25759(16) 0.43269(6) 0.0123(2) Uani 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
N1 C2 1.3593(16) . ?
N1 C5 1.3767(14) . ?
N1 C11 1.4552(15) . ?
C2 N3 1.3157(16) . ?
N3 C4 1.3795(14) . ?
C4 C5 1.3842(16) . ?
C4 C5* 1.4279(15) . ?
C5 C6* 1.4321(15) . ?
C1* N1* 1.3578(14) . ?
C1* C5* 1.4120(15) . ?
C1* C10* 1.4673(15) . ?
N1* C2* 1.3262(15) . ?
C2* C3* 1.3965(17) . ?
C3* C4* 1.3733(17) . ?
C4* C5* 1.4051(15) . ?
C6* C7* 1.4077(16) . ?
C6* C10* 1.4232(15) . ?
C7* C8* 1.3745(16) . ?
C8* C9* 1.3970(16) . ?
C9* N10* 1.3242(15) . ?
N10* C10* 1.3530(14) . ?

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 N1 C5 106.43(10) . . ?
C2 N1 C11 123.79(10) . . ?
C5 N1 C11 129.69(10) . . ?
N3 C2 N1 113.77(10) . . ?
C2 N3 C4 103.56(10) . . ?
N3 C4 C5 111.32(10) . . ?
N3 C4 C5* 127.28(10) . . ?
C5 C4 C5* 121.40(10) . . ?
N1 C5 C4 104.92(10) . . ?
N1 C5 C6* 132.39(11) . . ?
C4 C5 C6* 122.68(10) . . ?
N1* C1* C5* 121.85(10) . . ?
N1* C1* C10* 117.94(10) . . ?
C5* C1* C10* 120.20(10) . . ?
C2* N1* C1* 117.64(10) . . ?
N1* C2* C3* 124.30(11) . . ?
C4* C3* C2* 118.71(11) . . ?
C3* C4* C5* 118.69(11) . . ?
C4* C5* C1* 118.74(10) . . ?
C4* C5* C4 123.03(10) . . ?
C1* C5* C4 118.20(10) . . ?
C7* C6* C10* 117.45(10) . . ?
C7* C6* C5 125.67(10) . . ?
C10* C6* C5 116.88(10) . . ?
C8* C7* C6* 119.67(11) . . ?
C7* C8* C9* 118.40(11) . . ?
N10* C9* C8* 124.16(11) . . ?
C9* N10* C10* 118.04(10) . . ?
N10* C10* C6* 122.28(10) . . ?
N10* C10* C1* 117.15(10) . . ?
C6* C10* C1* 120.57(10) . . ?

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
C5 N1 C2 N3 0.57(14) . . . . ?
C11 N1 C2 N3 177.42(10) . . . . ?
N1 C2 N3 C4 -0.22(13) . . . . ?
C2 N3 C4 C5 -0.22(13) . . . . ?
C2 N3 C4 C5* -179.28(11) . . . . ?
C2 N1 C5 C4 -0.65(12) . . . . ?
C11 N1 C5 C4 -177.25(11) . . . . ?
C2 N1 C5 C6* 178.25(12) . . . . ?
C11 N1 C5 C6* 1.6(2) . . . . ?
N3 C4 C5 N1 0.55(13) . . . . ?
C5* C4 C5 N1 179.68(10) . . . . ?
N3 C4 C5 C6* -178.48(10) . . . . ?
C5* C4 C5 C6* 0.65(17) . . . . ?
C5* C1* N1* C2* -2.12(17) . . . . ?
C10* C1* N1* C2* 176.54(11) . . . . ?
C1* N1* C2* C3* -0.27(19) . . . . ?
N1* C2* C3* C4* 1.9(2) . . . . ?
C2* C3* C4* C5* -1.01(18) . . . . ?
C3* C4* C5* C1* -1.21(17) . . . . ?
C3* C4* C5* C4 -178.93(11) . . . . ?
N1* C1* C5* C4* 2.87(17) . . . . ?
C10* C1* C5* C4* -175.75(10) . . . . ?
N1* C1* C5* C4 -179.29(10) . . . . ?
C10* C1* C5* C4 2.09(16) . . . . ?
N3 C4 C5* C4* -5.91(19) . . . . ?
C5 C4 C5* C4* 175.11(11) . . . . ?
N3 C4 C5* C1* 176.35(10) . . . . ?
C5 C4 C5* C1* -2.62(17) . . . . ?
N1 C5 C6* C7* 2.7(2) . . . . ?
C4 C5 C6* C7* -178.57(11) . . . . ?
N1 C5 C6* C10* -176.90(11) . . . . ?
C4 C5 C6* C10* 1.83(16) . . . . ?
C10* C6* C7* C8* 0.58(16) . . . . ?
C5 C6* C7* C8* -179.02(11) . . . . ?
C6* C7* C8* C9* 0.36(17) . . . . ?
C7* C8* C9* N10* -1.02(18) . . . . ?
C8* C9* N10* C10* 0.60(17) . . . . ?
C9* N10* C10* C6* 0.44(16) . . . . ?
C9* N10* C10* C1* -178.68(10) . . . . ?
C7* C6* C10* N10* -1.02(16) . . . . ?
C5 C6* C10* N10* 178.61(10) . . . . ?
C7* C6* C10* C1* 178.07(10) . . . . ?
C5 C6* C10* C1* -2.30(16) . . . . ?
N1* C1* C10* N10* 0.84(15) . . . . ?
C5* C1* C10* N10* 179.51(10) . . . . ?
N1* C1* C10* C6* -178.30(10) . . . . ?
C5* C1* C10* C6* 0.38(16) . . . . ?

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
C2 H2 N1* 0.95 2.38 3.3158(16) 167.2 4_666
C11 H11B N10* 0.98 2.43 3.3808(15) 163.1 4_666
C11 H11B N10* 0.98 2.43 3.3808(15) 163.1 4_666
C2 H2 N1* 0.95 2.38 3.3158(16) 167.2 4_666

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
