# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_tangdong0624_pl
_audit_block_doi                 10.5517/cc1jj9gt
_database_code_depnum_ccdc_archive 'CCDC 1415846'
_audit_update_record             
;
2015-07-30 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;
_audit_creation_date             2015-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H11 N3)'
_chemical_formula_sum            'C30 H22 N6'
_chemical_formula_weight         466.53
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   24.392(6)
_cell_length_b                   4.0190(5)
_cell_length_c                   24.609(17)
_cell_angle_alpha                90
_cell_angle_beta                 105.47(4)
_cell_angle_gamma                90
_cell_volume                     2325.1(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4598
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         3.407
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1302
_reflns_number_total             2269
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²+1.7858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1837
_refine_ls_wR_factor_ref         0.2230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.09924(15) 0.7923(9) 0.24439(11) 0.0890(10) Uani 1 1 d . . . . .
N2 N 0.05295(15) 0.6239(9) 0.21433(12) 0.0903(11) Uani 1 1 d . . . . .
N3 N 0.09344(9) 0.5875(6) 0.13675(9) 0.0519(7) Uani 1 1 d . . . . .
C1 C 0.23544(14) 0.9760(9) 0.17415(14) 0.0703(9) Uani 1 1 d . . . . .
H1 H 0.2390 1.0330 0.2116 0.084 Uiso 1 1 calc R . . . .
C2 C 0.27963(15) 1.0441(9) 0.15065(16) 0.0780(10) Uani 1 1 d . . . . .
H2 H 0.3124 1.1469 0.1722 0.094 Uiso 1 1 calc R . . . .
C3 C 0.27533(14) 0.9608(9) 0.09575(16) 0.0714(10) Uani 1 1 d . . . . .
H3 H 0.3051 1.0065 0.0798 0.086 Uiso 1 1 calc R . . . .
C4 C 0.22685(14) 0.8097(9) 0.06454(14) 0.0733(10) Uani 1 1 d . . . . .
H4 H 0.2237 0.7533 0.0272 0.088 Uiso 1 1 calc R . . . .
C5 C 0.18240(13) 0.7397(9) 0.08796(12) 0.0625(9) Uani 1 1 d . . . . .
H5 H 0.1499 0.6348 0.0664 0.075 Uiso 1 1 calc R . . . .
C6 C 0.18617(12) 0.8253(7) 0.14338(12) 0.0523(7) Uani 1 1 d . . . . .
C7 C 0.13852(12) 0.7540(7) 0.16795(12) 0.0534(8) Uani 1 1 d . . . . .
C8 C 0.14153(14) 0.8552(9) 0.22120(12) 0.0693(9) Uani 1 1 d . . . . .
H8 H 0.1735 0.9697 0.2417 0.083 Uiso 1 1 calc R . . . .
C9 C 0.05107(12) 0.5241(7) 0.16039(11) 0.0513(7) Uani 1 1 d . . . . .
C10 C 0.00079(12) 0.3460(7) 0.12692(12) 0.0528(8) Uani 1 1 d . . . . .
C11 C -0.04080(13) 0.2197(8) 0.15100(14) 0.0635(9) Uani 1 1 d . . . . .
H11 H -0.0366 0.2470 0.1894 0.076 Uiso 1 1 calc R . . . .
C12 C -0.08751(14) 0.0567(9) 0.11883(16) 0.0694(10) Uani 1 1 d . . . . .
H12 H -0.1147 -0.0259 0.1355 0.083 Uiso 1 1 calc R . . . .
C13 C -0.09437(14) 0.0145(8) 0.06219(16) 0.0696(9) Uani 1 1 d . . . . .
H13 H -0.1263 -0.0950 0.0404 0.084 Uiso 1 1 calc R . . . .
C14 C -0.05382(14) 0.1350(8) 0.03783(14) 0.0661(9) Uani 1 1 d . . . . .
H14 H -0.0585 0.1065 -0.0006 0.079 Uiso 1 1 calc R . . . .
C15 C -0.00642(13) 0.2972(8) 0.06965(12) 0.0585(8) Uani 1 1 d . . . . .
H15 H 0.0209 0.3746 0.0527 0.070 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.091(2) 0.128(3) 0.0450(16) -0.0061(18) 0.0135(16) 0.028(2)
N2 0.100(2) 0.123(3) 0.0563(18) 0.0204(19) 0.0362(18) 0.045(2)
N3 0.0559(14) 0.0592(15) 0.0462(13) 0.0075(11) 0.0234(11) 0.0104(12)
C1 0.075(2) 0.078(2) 0.0535(19) 0.0003(18) 0.0098(17) -0.0081(18)
C2 0.064(2) 0.086(3) 0.079(2) 0.013(2) 0.0096(18) -0.0101(18)
C3 0.0563(19) 0.081(2) 0.082(2) 0.014(2) 0.0266(18) 0.0036(17)
C4 0.068(2) 0.095(3) 0.062(2) -0.0007(19) 0.0271(18) 0.0037(19)
C5 0.0568(18) 0.080(2) 0.0521(17) -0.0040(17) 0.0166(14) -0.0012(16)
C6 0.0535(16) 0.0545(17) 0.0478(16) 0.0056(14) 0.0117(13) 0.0087(13)
C7 0.0596(17) 0.0573(18) 0.0439(15) 0.0060(14) 0.0149(13) 0.0158(14)
C8 0.069(2) 0.095(3) 0.0421(16) -0.0076(17) 0.0110(15) 0.0146(19)
C9 0.0602(17) 0.0570(17) 0.0419(15) 0.0122(14) 0.0228(13) 0.0187(14)
C10 0.0571(17) 0.0553(17) 0.0527(16) 0.0155(14) 0.0265(14) 0.0190(14)
C11 0.067(2) 0.073(2) 0.0620(19) 0.0168(17) 0.0373(17) 0.0173(17)
C12 0.0611(19) 0.072(2) 0.087(2) 0.014(2) 0.0408(19) 0.0098(17)
C13 0.064(2) 0.066(2) 0.085(2) 0.005(2) 0.0294(18) 0.0048(16)
C14 0.072(2) 0.069(2) 0.063(2) 0.0010(17) 0.0275(17) 0.0007(17)
C15 0.0632(18) 0.0638(19) 0.0550(18) 0.0068(16) 0.0272(15) 0.0034(15)

_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 N2 1.354(4) . ?
N1 C8 1.330(4) . ?
N2 C9 1.376(4) . ?
N3 C7 1.340(4) . ?
N3 C9 1.339(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(4) . ?
C1 C6 1.378(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 C7 1.474(4) . ?
C7 C8 1.355(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.468(4) . ?
C10 C11 1.400(4) . ?
C10 C15 1.387(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(4) . ?
C15 H15 0.9300 . ?

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
C8 N1 N2 119.3(3) . . ?
N1 N2 C9 118.7(3) . . ?
C9 N3 C7 117.2(2) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C6 C1 C2 121.4(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 C7 121.8(3) . . ?
C5 C6 C7 120.2(3) . . ?
N3 C7 C6 118.6(3) . . ?
N3 C7 C8 121.9(3) . . ?
C8 C7 C6 119.5(3) . . ?
N1 C8 C7 120.7(3) . . ?
N1 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
N2 C9 C10 119.4(3) . . ?
N3 C9 N2 122.2(3) . . ?
N3 C9 C10 118.4(2) . . ?
C11 C10 C9 122.0(3) . . ?
C15 C10 C9 120.0(3) . . ?
C15 C10 C11 118.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.3(3) . . ?
C14 C15 H15 119.8 . . ?

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 N2 C9 N3 0.1(5) . . . . ?
N1 N2 C9 C10 -179.0(3) . . . . ?
N2 N1 C8 C7 0.3(5) . . . . ?
N2 C9 C10 C11 -12.0(4) . . . . ?
N2 C9 C10 C15 168.3(3) . . . . ?
N3 C7 C8 N1 -0.2(5) . . . . ?
N3 C9 C10 C11 168.8(3) . . . . ?
N3 C9 C10 C15 -10.8(4) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C1 C6 C7 N3 -175.7(3) . . . . ?
C1 C6 C7 C8 3.8(4) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
C2 C1 C6 C7 -179.5(3) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
C5 C6 C7 N3 4.1(4) . . . . ?
C5 C6 C7 C8 -176.4(3) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C6 C7 C8 N1 -179.6(3) . . . . ?
C7 N3 C9 N2 0.0(4) . . . . ?
C7 N3 C9 C10 179.2(2) . . . . ?
C8 N1 N2 C9 -0.3(5) . . . . ?
C9 N3 C7 C6 179.5(2) . . . . ?
C9 N3 C7 C8 0.0(4) . . . . ?
C9 C10 C11 C12 179.5(3) . . . . ?
C9 C10 C15 C14 -179.0(3) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C10 C15 C14 1.3(4) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C10 -0.9(5) . . . . ?
C15 C10 C11 C12 -0.8(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
