# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_mo_150606b_0m
_database_code_depnum_ccdc_archive 'CCDC 1435062'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3,5,6-tris(3-(pyrimidin-5-yl)phenyl)-1,2,4-triazine
_chemical_name_common            TPM-i-TAZ
_chemical_melting_point          523
_chemical_formula_moiety         'C33 H21 N9'
_chemical_formula_sum            'C34 H22 Cl3 N9'
_chemical_formula_weight         662.96

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0707(10)
_cell_length_b                   10.2070(12)
_cell_length_c                   16.8469(19)
_cell_angle_alpha                76.256(2)
_cell_angle_beta                 79.265(2)
_cell_angle_gamma                85.927(2)
_cell_volume                     1488.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7407
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      31.84

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9657
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            13398
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         29.50
_reflns_number_total             8153
_reflns_number_gt                6637
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 2sigma(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)+(0.1050P)²+0.0000P] 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         8153
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1656
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.63180(17) 0.32341(16) 0.22440(9) 0.0138(3) Uani 1 1 d . . .
C3 C 0.44053(17) 0.36784(16) 0.35468(9) 0.0150(3) Uani 1 1 d . . .
C2 C 0.55302(17) 0.21507(16) 0.28184(9) 0.0138(3) Uani 1 1 d . . .
C4 C 0.74623(17) 0.30646(15) 0.15175(9) 0.0135(3) Uani 1 1 d . . .
C5 C 0.86082(17) 0.20780(16) 0.16270(10) 0.0164(3) Uani 1 1 d . . .
H5 H 0.8671 0.1540 0.2164 0.020 Uiso 1 1 calc R . .
C6 C 0.96478(18) 0.18952(18) 0.09453(10) 0.0197(3) Uani 1 1 d . . .
H6 H 1.0424 0.1225 0.1018 0.024 Uiso 1 1 calc R . .
C7 C 0.95712(18) 0.26788(17) 0.01557(10) 0.0187(3) Uani 1 1 d . . .
H7 H 1.0280 0.2525 -0.0307 0.022 Uiso 1 1 calc R . .
C8 C 0.84555(17) 0.36935(16) 0.00377(9) 0.0152(3) Uani 1 1 d . . .
C9 C 0.74019(17) 0.38785(16) 0.07327(10) 0.0148(3) Uani 1 1 d . . .
H9 H 0.6642 0.4566 0.0666 0.018 Uiso 1 1 calc R . .
C10 C 0.84084(18) 0.45567(16) -0.07970(10) 0.0160(3) Uani 1 1 d . . .
C11 C 0.96867(19) 0.48087(18) -0.14097(10) 0.0202(3) Uani 1 1 d . . .
H11 H 1.0614 0.4395 -0.1285 0.024 Uiso 1 1 calc R . .
C12 C 0.8351(2) 0.61910(19) -0.22962(10) 0.0225(3) Uani 1 1 d . . .
H12 H 0.8337 0.6794 -0.2820 0.027 Uiso 1 1 calc R . .
C13 C 0.70877(19) 0.51808(18) -0.10297(10) 0.0189(3) Uani 1 1 d . . .
H13 H 0.6175 0.5004 -0.0646 0.023 Uiso 1 1 calc R . .
C14 C 0.56659(17) 0.07301(16) 0.27420(10) 0.0143(3) Uani 1 1 d . . .
C15 C 0.56229(18) -0.03116(16) 0.34562(10) 0.0163(3) Uani 1 1 d . . .
H15 H 0.5486 -0.0106 0.3987 0.020 Uiso 1 1 calc R . .
C16 C 0.57806(18) -0.16492(16) 0.33887(10) 0.0174(3) Uani 1 1 d . . .
H16 H 0.5776 -0.2352 0.3874 0.021 Uiso 1 1 calc R . .
C17 C 0.59446(17) -0.19667(16) 0.26209(10) 0.0169(3) Uani 1 1 d . . .
H17 H 0.6056 -0.2882 0.2581 0.020 Uiso 1 1 calc R . .
C18 C 0.59451(17) -0.09302(16) 0.19007(10) 0.0144(3) Uani 1 1 d . . .
C19 C 0.57994(17) 0.04079(16) 0.19756(9) 0.0140(3) Uani 1 1 d . . .
H19 H 0.5791 0.1112 0.1492 0.017 Uiso 1 1 calc R . .
C20 C 0.61291(17) -0.12362(16) 0.10720(10) 0.0148(3) Uani 1 1 d . . .
C21 C 0.67891(17) -0.03294(17) 0.03550(10) 0.0175(3) Uani 1 1 d . . .
H21 H 0.7147 0.0492 0.0409 0.021 Uiso 1 1 calc R . .
C22 C 0.64466(19) -0.17592(18) -0.04405(11) 0.0197(3) Uani 1 1 d . . .
H22 H 0.6565 -0.1945 -0.0976 0.024 Uiso 1 1 calc R . .
C23 C 0.56585(19) -0.24406(17) 0.09504(11) 0.0203(3) Uani 1 1 d . . .
H23 H 0.5215 -0.3095 0.1420 0.024 Uiso 1 1 calc R . .
C24 C 0.33400(17) 0.39492(16) 0.42711(10) 0.0155(3) Uani 1 1 d . . .
C25 C 0.23891(18) 0.29310(17) 0.47611(10) 0.0181(3) Uani 1 1 d . . .
H25 H 0.2427 0.2074 0.4628 0.022 Uiso 1 1 calc R . .
C26 C 0.13875(19) 0.31867(18) 0.54448(11) 0.0201(3) Uani 1 1 d . . .
H26 H 0.0749 0.2495 0.5783 0.024 Uiso 1 1 calc R . .
C27 C 0.13113(18) 0.44404(17) 0.56374(10) 0.0183(3) Uani 1 1 d . . .
H27 H 0.0622 0.4601 0.6105 0.022 Uiso 1 1 calc R . .
C28 C 0.22446(17) 0.54710(16) 0.51461(10) 0.0156(3) Uani 1 1 d . . .
C29 C 0.32607(17) 0.52129(16) 0.44652(10) 0.0161(3) Uani 1 1 d . . .
H29 H 0.3905 0.5903 0.4130 0.019 Uiso 1 1 calc R . .
C30 C 0.20935(17) 0.68320(16) 0.53281(10) 0.0155(3) Uani 1 1 d . . .
C31 C 0.2250(2) 0.80127(17) 0.47024(10) 0.0199(3) Uani 1 1 d . . .
H31 H 0.2538 0.7938 0.4143 0.024 Uiso 1 1 calc R . .
C32 C 0.1615(2) 0.92812(18) 0.56590(11) 0.0232(4) Uani 1 1 d . . .
H32 H 0.1419 1.0148 0.5778 0.028 Uiso 1 1 calc R . .
C33 C 0.17118(19) 0.70123(17) 0.61356(10) 0.0192(3) Uani 1 1 d . . .
H33 H 0.1624 0.6238 0.6583 0.023 Uiso 1 1 calc R . .
C34 C 0.14710(19) 0.85986(18) 0.21386(11) 0.0199(3) Uani 1 1 d . . .
H34 H 0.2004 0.8921 0.1555 0.024 Uiso 1 1 calc R . .
Cl1 Cl 0.23047(5) 0.70465(4) 0.25789(3) 0.02418(12) Uani 1 1 d . . .
Cl2 Cl 0.16199(6) 0.98210(5) 0.26999(3) 0.02932(13) Uani 1 1 d . . .
Cl3 Cl -0.04322(5) 0.83771(5) 0.21210(4) 0.03389(14) Uani 1 1 d . . .
N1 N 0.70452(18) 0.60168(16) -0.17680(9) 0.0225(3) Uani 1 1 d . . .
N2 N 0.96712(17) 0.56031(16) -0.21622(9) 0.0229(3) Uani 1 1 d . . .
N3 N 0.69393(16) -0.05663(15) -0.04031(9) 0.0194(3) Uani 1 1 d . . .
N4 N 0.58104(17) -0.27064(16) 0.01957(9) 0.0217(3) Uani 1 1 d . . .
N5 N 0.20126(19) 0.92505(16) 0.48556(9) 0.0240(3) Uani 1 1 d . . .
N6 N 0.14640(18) 0.82310(16) 0.63069(9) 0.0235(3) Uani 1 1 d . . .
N7 N 0.46024(15) 0.23869(14) 0.34834(8) 0.0156(3) Uani 1 1 d . . .
N8 N 0.60683(16) 0.44925(14) 0.23448(9) 0.0174(3) Uani 1 1 d . . .
N9 N 0.50744(16) 0.47273(14) 0.29970(8) 0.0183(3) 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
C1 N8 1.333(2) . ?
C1 C2 1.420(2) . ?
C1 C4 1.486(2) . ?
C3 N9 1.336(2) . ?
C3 N7 1.344(2) . ?
C3 C24 1.477(2) . ?
C2 N7 1.330(2) . ?
C2 C14 1.480(2) . ?
C4 C9 1.393(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(2) . ?
C8 C10 1.478(2) . ?
C9 H9 0.9500 . ?
C10 C13 1.394(2) . ?
C10 C11 1.395(2) . ?
C11 N2 1.335(2) . ?
C11 H11 0.9500 . ?
C12 N2 1.334(2) . ?
C12 N1 1.337(2) . ?
C12 H12 0.9500 . ?
C13 N1 1.336(2) . ?
C13 H13 0.9500 . ?
C14 C19 1.388(2) . ?
C14 C15 1.400(2) . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.408(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(2) . ?
C18 C20 1.479(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.397(2) . ?
C20 C23 1.401(2) . ?
C21 N3 1.336(2) . ?
C21 H21 0.9500 . ?
C22 N4 1.332(2) . ?
C22 N3 1.346(2) . ?
C22 H22 0.9500 . ?
C23 N4 1.343(2) . ?
C23 H23 0.9500 . ?
C24 C29 1.398(2) . ?
C24 C25 1.400(2) . ?
C25 C26 1.393(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.400(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.396(2) . ?
C28 C30 1.484(2) . ?
C29 H29 0.9500 . ?
C30 C33 1.393(2) . ?
C30 C31 1.396(2) . ?
C31 N5 1.343(2) . ?
C31 H31 0.9500 . ?
C32 N6 1.330(2) . ?
C32 N5 1.341(2) . ?
C32 H32 0.9500 . ?
C33 N6 1.337(2) . ?
C33 H33 0.9500 . ?
C34 Cl2 1.7612(18) . ?
C34 Cl3 1.7635(17) . ?
C34 Cl1 1.7642(18) . ?
C34 H34 1.0000 . ?
N8 N9 1.3427(19) . ?

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
N8 C1 C2 120.27(14) . . ?
N8 C1 C4 115.85(13) . . ?
C2 C1 C4 123.87(14) . . ?
N9 C3 N7 124.89(14) . . ?
N9 C3 C24 118.06(14) . . ?
N7 C3 C24 117.04(14) . . ?
N7 C2 C1 119.60(14) . . ?
N7 C2 C14 115.76(14) . . ?
C1 C2 C14 124.63(14) . . ?
C9 C4 C5 120.05(14) . . ?
C9 C4 C1 120.47(14) . . ?
C5 C4 C1 119.47(14) . . ?
C6 C5 C4 119.38(15) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.92(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 120.47(15) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 118.45(14) . . ?
C7 C8 C10 120.39(14) . . ?
C9 C8 C10 121.16(14) . . ?
C4 C9 C8 120.69(14) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C13 C10 C11 115.09(15) . . ?
C13 C10 C8 122.57(14) . . ?
C11 C10 C8 122.34(15) . . ?
N2 C11 C10 123.21(16) . . ?
N2 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N2 C12 N1 126.58(16) . . ?
N2 C12 H12 116.7 . . ?
N1 C12 H12 116.7 . . ?
N1 C13 C10 123.05(15) . . ?
N1 C13 H13 118.5 . . ?
C10 C13 H13 118.5 . . ?
C19 C14 C15 119.19(14) . . ?
C19 C14 C2 121.21(14) . . ?
C15 C14 C2 119.58(14) . . ?
C16 C15 C14 119.97(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.66(15) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.89(15) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 118.91(14) . . ?
C19 C18 C20 119.91(14) . . ?
C17 C18 C20 121.16(14) . . ?
C14 C19 C18 121.31(14) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C23 115.59(15) . . ?
C21 C20 C18 121.65(14) . . ?
C23 C20 C18 122.77(14) . . ?
N3 C21 C20 122.92(15) . . ?
N3 C21 H21 118.5 . . ?
C20 C21 H21 118.5 . . ?
N4 C22 N3 126.68(16) . . ?
N4 C22 H22 116.7 . . ?
N3 C22 H22 116.7 . . ?
N4 C23 C20 122.55(16) . . ?
N4 C23 H23 118.7 . . ?
C20 C23 H23 118.7 . . ?
C29 C24 C25 119.83(14) . . ?
C29 C24 C3 120.73(14) . . ?
C25 C24 C3 119.43(14) . . ?
C26 C25 C24 119.38(15) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C27 C26 C25 120.73(15) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 120.38(15) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 119.00(15) . . ?
C29 C28 C30 120.97(14) . . ?
C27 C28 C30 119.96(14) . . ?
C28 C29 C24 120.67(14) . . ?
C28 C29 H29 119.7 . . ?
C24 C29 H29 119.7 . . ?
C33 C30 C31 115.66(15) . . ?
C33 C30 C28 121.91(15) . . ?
C31 C30 C28 122.36(14) . . ?
N5 C31 C30 122.98(15) . . ?
N5 C31 H31 118.5 . . ?
C30 C31 H31 118.5 . . ?
N6 C32 N5 127.09(17) . . ?
N6 C32 H32 116.5 . . ?
N5 C32 H32 116.5 . . ?
N6 C33 C30 122.66(16) . . ?
N6 C33 H33 118.7 . . ?
C30 C33 H33 118.7 . . ?
Cl2 C34 Cl3 110.02(10) . . ?
Cl2 C34 Cl1 110.84(9) . . ?
Cl3 C34 Cl1 109.89(10) . . ?
Cl2 C34 H34 108.7 . . ?
Cl3 C34 H34 108.7 . . ?
Cl1 C34 H34 108.7 . . ?
C13 N1 C12 115.99(15) . . ?
C12 N2 C11 115.95(15) . . ?
C21 N3 C22 115.98(15) . . ?
C22 N4 C23 116.27(15) . . ?
C32 N5 C31 115.31(15) . . ?
C32 N6 C33 116.26(15) . . ?
C2 N7 C3 116.89(14) . . ?
C1 N8 N9 119.54(14) . . ?
C3 N9 N8 118.65(14) . . ?

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
N8 C1 C2 N7 -3.7(2) . . . . ?
C4 C1 C2 N7 175.25(14) . . . . ?
N8 C1 C2 C14 176.81(14) . . . . ?
C4 C1 C2 C14 -4.2(2) . . . . ?
N8 C1 C4 C9 -49.7(2) . . . . ?
C2 C1 C4 C9 131.26(16) . . . . ?
N8 C1 C4 C5 130.22(16) . . . . ?
C2 C1 C4 C5 -48.8(2) . . . . ?
C9 C4 C5 C6 -1.9(2) . . . . ?
C1 C4 C5 C6 178.14(14) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C6 C7 C8 C10 177.83(15) . . . . ?
C5 C4 C9 C8 2.1(2) . . . . ?
C1 C4 C9 C8 -177.98(14) . . . . ?
C7 C8 C9 C4 -0.5(2) . . . . ?
C10 C8 C9 C4 -179.59(14) . . . . ?
C7 C8 C10 C13 153.95(16) . . . . ?
C9 C8 C10 C13 -26.9(2) . . . . ?
C7 C8 C10 C11 -26.2(2) . . . . ?
C9 C8 C10 C11 152.91(16) . . . . ?
C13 C10 C11 N2 1.0(2) . . . . ?
C8 C10 C11 N2 -178.84(16) . . . . ?
C11 C10 C13 N1 -3.3(2) . . . . ?
C8 C10 C13 N1 176.54(15) . . . . ?
N7 C2 C14 C19 142.18(15) . . . . ?
C1 C2 C14 C19 -38.3(2) . . . . ?
N7 C2 C14 C15 -36.3(2) . . . . ?
C1 C2 C14 C15 143.22(16) . . . . ?
C19 C14 C15 C16 2.8(2) . . . . ?
C2 C14 C15 C16 -178.68(14) . . . . ?
C14 C15 C16 C17 -1.6(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C19 0.9(2) . . . . ?
C16 C17 C18 C20 179.55(14) . . . . ?
C15 C14 C19 C18 -2.3(2) . . . . ?
C2 C14 C19 C18 179.24(13) . . . . ?
C17 C18 C19 C14 0.5(2) . . . . ?
C20 C18 C19 C14 -178.23(14) . . . . ?
C19 C18 C20 C21 27.9(2) . . . . ?
C17 C18 C20 C21 -150.77(15) . . . . ?
C19 C18 C20 C23 -152.03(16) . . . . ?
C17 C18 C20 C23 29.3(2) . . . . ?
C23 C20 C21 N3 1.5(2) . . . . ?
C18 C20 C21 N3 -178.47(15) . . . . ?
C21 C20 C23 N4 -0.8(2) . . . . ?
C18 C20 C23 N4 179.12(15) . . . . ?
N9 C3 C24 C29 -12.6(2) . . . . ?
N7 C3 C24 C29 168.74(14) . . . . ?
N9 C3 C24 C25 166.60(15) . . . . ?
N7 C3 C24 C25 -12.0(2) . . . . ?
C29 C24 C25 C26 -0.9(2) . . . . ?
C3 C24 C25 C26 179.87(15) . . . . ?
C24 C25 C26 C27 0.8(3) . . . . ?
C25 C26 C27 C28 -0.1(3) . . . . ?
C26 C27 C28 C29 -0.6(2) . . . . ?
C26 C27 C28 C30 176.45(15) . . . . ?
C27 C28 C29 C24 0.5(2) . . . . ?
C30 C28 C29 C24 -176.51(14) . . . . ?
C25 C24 C29 C28 0.2(2) . . . . ?
C3 C24 C29 C28 179.47(14) . . . . ?
C29 C28 C30 C33 -148.63(16) . . . . ?
C27 C28 C30 C33 34.4(2) . . . . ?
C29 C28 C30 C31 34.6(2) . . . . ?
C27 C28 C30 C31 -142.37(17) . . . . ?
C33 C30 C31 N5 -1.8(2) . . . . ?
C28 C30 C31 N5 175.16(16) . . . . ?
C31 C30 C33 N6 2.0(2) . . . . ?
C28 C30 C33 N6 -174.99(16) . . . . ?
C10 C13 N1 C12 2.4(3) . . . . ?
N2 C12 N1 C13 1.0(3) . . . . ?
N1 C12 N2 C11 -3.1(3) . . . . ?
C10 C11 N2 C12 1.9(3) . . . . ?
C20 C21 N3 C22 -1.6(2) . . . . ?
N4 C22 N3 C21 1.1(3) . . . . ?
N3 C22 N4 C23 -0.5(3) . . . . ?
C20 C23 N4 C22 0.4(3) . . . . ?
N6 C32 N5 C31 1.4(3) . . . . ?
C30 C31 N5 C32 0.2(3) . . . . ?
N5 C32 N6 C33 -1.3(3) . . . . ?
C30 C33 N6 C32 -0.6(3) . . . . ?
C1 C2 N7 C3 3.5(2) . . . . ?
C14 C2 N7 C3 -176.94(13) . . . . ?
N9 C3 N7 C2 -0.4(2) . . . . ?
C24 C3 N7 C2 178.16(13) . . . . ?
C2 C1 N8 N9 0.5(2) . . . . ?
C4 C1 N8 N9 -178.55(13) . . . . ?
N7 C3 N9 N8 -2.8(2) . . . . ?
C24 C3 N9 N8 178.65(14) . . . . ?
C1 N8 N9 C3 2.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        29.50
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.106
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, n-hexane'
_chemical_compound_source        no
_chemical_properties_physical    Efflorescent
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_YIN-TAZ001A
_database_code_depnum_ccdc_archive 'CCDC 1435063'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,4,6-tris(3-(pyrimidin-5-yl)phenyl)-1,3,5-triazine
_chemical_name_common            TPM-TAZ
_chemical_melting_point          332
_chemical_formula_moiety         'C33 H21 N9'
_chemical_formula_sum            'C33 H21 N9'
_chemical_formula_weight         543.59

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                   12.689(6)
_cell_length_b                   7.276(4)
_cell_length_c                   28.901(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.641(7)
_cell_angle_gamma                90
_cell_volume                     2660(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20589
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.810
_diffrn_reflns_theta_max         29.016
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             6457
_reflns_number_gt                4154
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1014P)²+0.1639P] 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         6457
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.40657(11) 0.6744(2) 0.02406(5) 0.0380(3) Uani 1 1 d . . . . .
N2 N 0.58886(11) 0.7542(2) 0.02663(5) 0.0404(4) Uani 1 1 d . . . . .
N3 N 0.51552(11) 0.6497(2) 0.09513(5) 0.0404(3) Uani 1 1 d . . . . .
C10 C 0.48019(12) 0.7895(2) -0.04548(6) 0.0358(4) Uani 1 1 d . . . . .
C16 C 0.70240(14) 0.7233(2) 0.09745(6) 0.0406(4) Uani 1 1 d . . . . .
C2 C 0.49200(13) 0.7371(2) 0.00462(6) 0.0353(4) Uani 1 1 d . . . . .
C22 C 0.25868(14) 0.4696(2) 0.21496(6) 0.0407(4) Uani 1 1 d . . . . .
C11 C 0.38465(13) 0.7648(2) -0.07212(6) 0.0380(4) Uani 1 1 d . . . . .
H11 H 0.3272 0.7152 -0.0585 0.046 Uiso 1 1 calc R U . . .
C3 C 0.59609(13) 0.7097(2) 0.07177(6) 0.0381(4) Uani 1 1 d . . . . .
C12 C 0.37398(13) 0.8131(2) -0.11891(6) 0.0409(4) Uani 1 1 d . . . . .
C5 C 0.33689(13) 0.5508(2) 0.14100(6) 0.0388(4) Uani 1 1 d . . . . .
H5 H 0.3960 0.5968 0.1583 0.047 Uiso 1 1 calc R U . . .
C1 C 0.42291(13) 0.6326(2) 0.06956(6) 0.0363(4) Uani 1 1 d . . . . .
C15 C 0.56659(13) 0.8643(2) -0.06576(6) 0.0419(4) Uani 1 1 d . . . . .
H15 H 0.6306 0.8812 -0.0482 0.050 Uiso 1 1 calc R U . . .
C4 C 0.33252(13) 0.5569(2) 0.09275(6) 0.0362(4) Uani 1 1 d . . . . .
C6 C 0.25397(13) 0.4769(2) 0.16377(6) 0.0388(4) Uani 1 1 d . . . . .
C30 C 0.98417(13) 0.8095(3) 0.06887(6) 0.0414(4) Uani 1 1 d . . . . .
C18 C 0.89147(14) 0.7724(2) 0.09570(6) 0.0415(4) Uani 1 1 d . . . . .
C7 C 0.16545(14) 0.4083(3) 0.13690(6) 0.0443(4) Uani 1 1 d . . . . .
H7 H 0.1095 0.3579 0.1515 0.053 Uiso 1 1 calc R U . . .
C13 C 0.46142(15) 0.8882(3) -0.13835(7) 0.0493(5) Uani 1 1 d . . . . .
H13 H 0.4558 0.9219 -0.1695 0.059 Uiso 1 1 calc R U . . .
N4 N 0.35630(14) 0.4392(3) 0.28925(6) 0.0615(5) Uani 1 1 d . . . . .
C17 C 0.79060(14) 0.7562(2) 0.07292(6) 0.0405(4) Uani 1 1 d . . . . .
H17 H 0.7821 0.7675 0.0408 0.049 Uiso 1 1 calc R U . . .
C8 C 0.16063(15) 0.4148(3) 0.08903(6) 0.0462(4) Uani 1 1 d . . . . .
H8 H 0.1013 0.3697 0.0717 0.055 Uiso 1 1 calc R U . . .
C19 C 0.90229(16) 0.7563(3) 0.14396(7) 0.0519(5) Uani 1 1 d . . . . .
H19 H 0.9688 0.7673 0.1597 0.062 Uiso 1 1 calc R U . . .
C9 C 0.24341(14) 0.4879(2) 0.06675(6) 0.0418(4) Uani 1 1 d . . . . .
H9 H 0.2399 0.4912 0.0345 0.050 Uiso 1 1 calc R U . . .
C20 C 0.81527(17) 0.7241(3) 0.16846(7) 0.0589(6) Uani 1 1 d . . . . .
H20 H 0.8237 0.7136 0.2006 0.071 Uiso 1 1 calc R U . . .
C29 C 0.27214(15) 0.7884(3) -0.14782(7) 0.0481(5) Uani 1 1 d . . . . .
N5 N 0.17011(14) 0.4750(3) 0.28543(6) 0.0593(5) Uani 1 1 d . . . . .
C23 C 0.35190(16) 0.4458(3) 0.24285(7) 0.0530(5) Uani 1 1 d . . . . .
H23 H 0.4146 0.4337 0.2286 0.064 Uiso 1 1 calc R U . . .
C21 C 0.71531(16) 0.7073(3) 0.14569(7) 0.0519(5) Uani 1 1 d . . . . .
H21 H 0.6571 0.6854 0.1625 0.062 Uiso 1 1 calc R U . . .
C14 C 0.55619(15) 0.9132(3) -0.11205(7) 0.0506(5) Uani 1 1 d . . . . .
H14 H 0.6135 0.9635 -0.1257 0.061 Uiso 1 1 calc R U . . .
C25 C 0.16919(16) 0.4849(3) 0.23939(7) 0.0509(5) Uani 1 1 d . . . . .
H25 H 0.1045 0.5031 0.2225 0.061 Uiso 1 1 calc R U . . .
C26 C 0.17455(15) 0.7761(3) -0.13026(8) 0.0567(5) Uani 1 1 d . . . . .
H26 H 0.1720 0.7772 -0.0982 0.068 Uiso 1 1 calc R U . . .
N8 N 1.07653(14) 0.7642(3) 0.00037(6) 0.0581(5) Uani 1 1 d . . . . .
N9 N 1.15129(13) 0.9561(3) 0.06160(7) 0.0623(5) Uani 1 1 d . . . . .
C31 C 0.99442(15) 0.7338(3) 0.02556(7) 0.0504(5) Uani 1 1 d . . . . .
H31 H 0.9408 0.6569 0.0132 0.061 Uiso 1 1 calc R U . . .
C33 C 1.06620(15) 0.9242(3) 0.08476(7) 0.0538(5) Uani 1 1 d . . . . .
H33 H 1.0619 0.9825 0.1132 0.065 Uiso 1 1 calc R U . . .
C28 C 0.2685(2) 0.7748(5) -0.19555(8) 0.1003(11) Uani 1 1 d . . . . .
H28 H 0.3323 0.7727 -0.2093 0.120 Uiso 1 1 calc R U . . .
N6 N 0.08388(14) 0.7627(3) -0.15647(8) 0.0693(6) Uani 1 1 d . . . . .
C24 C 0.26483(18) 0.4534(3) 0.30781(7) 0.0588(6) Uani 1 1 d . . . . .
H24 H 0.2671 0.4476 0.3400 0.071 Uiso 1 1 calc R U . . .
C32 C 1.15078(17) 0.8739(3) 0.02060(8) 0.0591(5) Uani 1 1 d . . . . .
H32 H 1.2093 0.8954 0.0040 0.071 Uiso 1 1 calc R U . . .
C27 C 0.0920(2) 0.7617(4) -0.20150(10) 0.0791(8) Uani 1 1 d . . . . .
H27 H 0.0288 0.7588 -0.2202 0.095 Uiso 1 1 calc R U . . .
N7 N 0.17950(19) 0.7644(5) -0.22333(7) 0.1160(11) 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 1.341(2) . ?
N1 C1 1.349(2) . ?
N2 C3 1.340(2) . ?
N2 C2 1.343(2) . ?
N3 C1 1.342(2) . ?
N3 C3 1.343(2) . ?
C10 C11 1.394(2) . ?
C10 C15 1.395(2) . ?
C10 C2 1.493(2) . ?
C16 C17 1.393(3) . ?
C16 C21 1.396(3) . ?
C16 C3 1.489(2) . ?
C22 C23 1.387(3) . ?
C22 C25 1.389(3) . ?
C22 C6 1.477(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.395(3) . ?
C12 C29 1.492(2) . ?
C5 C4 1.392(2) . ?
C5 C6 1.394(2) . ?
C1 C4 1.481(2) . ?
C15 C14 1.380(3) . ?
C4 C9 1.399(2) . ?
C6 C7 1.405(2) . ?
C30 C31 1.383(3) . ?
C30 C33 1.384(3) . ?
C30 C18 1.485(3) . ?
C18 C19 1.395(3) . ?
C18 C17 1.396(2) . ?
C7 C8 1.381(3) . ?
C13 C14 1.382(3) . ?
N4 C24 1.321(3) . ?
N4 C23 1.339(2) . ?
C8 C9 1.382(3) . ?
C19 C20 1.379(3) . ?
C20 C21 1.386(3) . ?
C29 C26 1.379(3) . ?
C29 C28 1.380(3) . ?
N5 C24 1.327(3) . ?
N5 C25 1.332(3) . ?
C26 N6 1.329(2) . ?
N8 C32 1.333(3) . ?
N8 C31 1.337(3) . ?
N9 C32 1.327(3) . ?
N9 C33 1.336(3) . ?
C28 N7 1.333(3) . ?
N6 C27 1.314(3) . ?
C27 N7 1.321(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 N1 C1 114.80(14) . . ?
C3 N2 C2 115.27(15) . . ?
C1 N3 C3 114.93(15) . . ?
C11 C10 C15 119.74(16) . . ?
C11 C10 C2 121.15(15) . . ?
C15 C10 C2 119.11(14) . . ?
C17 C16 C21 119.24(16) . . ?
C17 C16 C3 119.37(16) . . ?
C21 C16 C3 121.38(17) . . ?
N1 C2 N2 124.94(16) . . ?
N1 C2 C10 118.18(14) . . ?
N2 C2 C10 116.87(15) . . ?
C23 C22 C25 114.09(17) . . ?
C23 C22 C6 123.37(17) . . ?
C25 C22 C6 122.54(16) . . ?
C12 C11 C10 121.02(16) . . ?
N2 C3 N3 124.96(15) . . ?
N2 C3 C16 117.19(15) . . ?
N3 C3 C16 117.83(15) . . ?
C11 C12 C13 118.15(16) . . ?
C11 C12 C29 121.65(16) . . ?
C13 C12 C29 120.19(16) . . ?
C4 C5 C6 121.00(15) . . ?
N3 C1 N1 125.05(15) . . ?
N3 C1 C4 117.44(15) . . ?
N1 C1 C4 117.48(14) . . ?
C14 C15 C10 119.41(15) . . ?
C5 C4 C9 119.44(16) . . ?
C5 C4 C1 119.73(15) . . ?
C9 C4 C1 120.82(16) . . ?
C5 C6 C7 118.47(16) . . ?
C5 C6 C22 121.07(15) . . ?
C7 C6 C22 120.46(16) . . ?
C31 C30 C33 114.67(18) . . ?
C31 C30 C18 122.46(16) . . ?
C33 C30 C18 122.86(17) . . ?
C19 C18 C17 118.45(18) . . ?
C19 C18 C30 121.28(15) . . ?
C17 C18 C30 120.26(16) . . ?
C8 C7 C6 120.69(17) . . ?
C14 C13 C12 121.01(17) . . ?
C24 N4 C23 115.92(18) . . ?
C16 C17 C18 121.22(16) . . ?
C7 C8 C9 120.42(16) . . ?
C20 C19 C18 120.62(17) . . ?
C8 C9 C4 119.96(16) . . ?
C19 C20 C21 120.74(18) . . ?
C26 C29 C28 113.87(18) . . ?
C26 C29 C12 124.38(18) . . ?
C28 C29 C12 121.75(19) . . ?
C24 N5 C25 115.31(18) . . ?
N4 C23 C22 123.44(19) . . ?
C20 C21 C16 119.72(19) . . ?
C15 C14 C13 120.67(17) . . ?
N5 C25 C22 124.21(18) . . ?
N6 C26 C29 123.8(2) . . ?
C32 N8 C31 114.49(18) . . ?
C32 N9 C33 115.07(18) . . ?
N8 C31 C30 124.15(18) . . ?
N9 C33 C30 123.72(19) . . ?
N7 C28 C29 124.4(3) . . ?
C27 N6 C26 115.5(2) . . ?
N4 C24 N5 127.01(19) . . ?
N9 C32 N8 127.9(2) . . ?
N6 C27 N7 127.6(2) . . ?
C27 N7 C28 114.6(2) . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.067



_exptl_crystal_recrystallization_method Sublimation
_chemical_compound_source        no
_chemical_properties_physical    no
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_tpb2015003a
_database_code_depnum_ccdc_archive 'CCDC 1435065'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1,3,5-tri(3-(pyrimidin-5-yl)phenyl)benzene
_chemical_name_common            TPM-TPB
_chemical_melting_point          247
_chemical_formula_moiety         'C36 H24 N6'
_chemical_formula_sum            'C36 H24 N6'
_chemical_formula_weight         540.61

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   13.250(8)
_cell_length_b                   9.163(6)
_cell_length_c                   23.928(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.006(8)
_cell_angle_gamma                90.00
_cell_volume                     2842(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12917
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0362
_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       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         21.92
_reflns_number_total             3393
_reflns_number_gt                2526
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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)+(0.1346P)²+0.4509P] 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         3393
_refine_ls_number_parameters     404
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.2034
_refine_ls_wR_factor_gt          0.1800
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.084
_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 0.8935(2) 0.6681(3) 1.03657(12) 0.0491(8) Uani 1 1 d . . .
C13 C 0.8223(2) 0.5557(3) 0.88123(12) 0.0489(8) Uani 1 1 d . . .
C4 C 0.9756(2) 0.6841(3) 0.93882(12) 0.0477(8) Uani 1 1 d . . .
H4 H 1.0034 0.6887 0.9062 0.057 Uiso 1 1 calc R . .
C20 C 1.2026(2) 0.7567(3) 0.96196(12) 0.0483(8) Uani 1 1 d . . .
H20 H 1.1855 0.6724 0.9404 0.058 Uiso 1 1 calc R . .
C3 C 0.8802(2) 0.6191(3) 0.93544(12) 0.0449(7) Uani 1 1 d . . .
C7 C 0.8492(2) 0.6563(3) 1.08829(13) 0.0514(8) Uani 1 1 d . . .
C2 C 0.8400(2) 0.6127(3) 0.98458(13) 0.0510(8) Uani 1 1 d . . .
H2 H 0.7756 0.5703 0.9827 0.061 Uiso 1 1 calc R . .
C19 C 1.1322(2) 0.8142(3) 0.99171(12) 0.0459(8) Uani 1 1 d . . .
C5 C 1.0311(2) 0.7429(3) 0.98973(12) 0.0446(7) Uani 1 1 d . . .
C6 C 0.9893(2) 0.7327(3) 1.03837(13) 0.0488(8) Uani 1 1 d . . .
H6 H 1.0261 0.7697 1.0728 0.059 Uiso 1 1 calc R . .
C8 C 0.9106(2) 0.6234(3) 1.14126(13) 0.0529(8) Uani 1 1 d . . .
H8 H 0.9812 0.6114 1.1443 0.063 Uiso 1 1 calc R . .
C24 C 1.1599(2) 0.9405(3) 1.02350(14) 0.0584(9) Uani 1 1 d . . .
H24 H 1.1143 0.9811 1.0439 0.070 Uiso 1 1 calc R . .
C14 C 0.7618(2) 0.4313(3) 0.88154(13) 0.0515(8) Uani 1 1 d . A .
H14 H 0.7603 0.3867 0.9163 0.062 Uiso 1 1 calc R . .
C21 C 1.2985(2) 0.8223(3) 0.96365(13) 0.0552(9) Uani 1 1 d . . .
C12 C 0.7440(3) 0.6745(4) 1.08515(15) 0.0691(10) Uani 1 1 d . . .
H12 H 0.7009 0.6975 1.0504 0.083 Uiso 1 1 calc R . .
C9 C 0.8695(3) 0.6079(3) 1.19009(13) 0.0588(9) Uani 1 1 d . . .
C23 C 1.2540(3) 1.0063(4) 1.02511(16) 0.0714(10) Uani 1 1 d . . .
H23 H 1.2717 1.0904 1.0467 0.086 Uiso 1 1 calc R . .
C15 C 0.7040(2) 0.3720(4) 0.83190(14) 0.0587(9) Uani 1 1 d . . .
C10 C 0.7644(3) 0.6263(4) 1.18551(16) 0.0757(11) Uani 1 1 d . . .
H10 H 0.7356 0.6169 1.2176 0.091 Uiso 1 1 calc R . .
C25 C 0.9360(3) 0.5751(3) 1.24614(13) 0.0621(9) Uani 1 1 d . . .
C33 C 1.3728(2) 0.7572(3) 0.93222(15) 0.0591(9) Uani 1 1 d . . .
C18 C 0.8253(3) 0.6164(4) 0.82875(14) 0.0729(10) Uani 1 1 d . A .
H18 H 0.8650 0.6993 0.8270 0.087 Uiso 1 1 calc R . .
N5 N 1.4134(3) 0.6647(4) 0.84604(15) 0.0951(11) Uani 1 1 d . . .
N2 N 0.9616(4) 0.4591(4) 1.33775(15) 0.0965(11) Uani 1 1 d . . .
C11 C 0.7030(3) 0.6585(5) 1.13328(19) 0.0867(12) Uani 1 1 d . . .
H11 H 0.6323 0.6698 1.1303 0.104 Uiso 1 1 calc R . .
C22 C 1.3221(3) 0.9474(4) 0.99458(16) 0.0699(10) Uani 1 1 d . . .
H22 H 1.3848 0.9936 0.9951 0.084 Uiso 1 1 calc R . .
N6 N 1.5443(3) 0.6781(5) 0.9309(2) 0.1081(13) Uani 1 1 d . . .
C17 C 0.7703(3) 0.5553(5) 0.77886(16) 0.0916(13) Uani 1 1 d . . .
H17 H 0.7749 0.5959 0.7438 0.110 Uiso 1 1 calc R A .
C28 C 0.9035(4) 0.4890(4) 1.28657(17) 0.0832(11) Uani 1 1 d . . .
H28 H 0.8374 0.4498 1.2775 0.100 Uiso 1 1 calc R . .
C16 C 0.7089(3) 0.4353(5) 0.78052(15) 0.0787(11) Uani 1 1 d . A .
H16 H 0.6706 0.3969 0.7468 0.094 Uiso 1 1 calc R . .
C34 C 1.3465(3) 0.7183(5) 0.87577(18) 0.0781(11) Uani 1 1 d . . .
H34 H 1.2781 0.7297 0.8570 0.094 Uiso 1 1 calc R . .
C26 C 1.0339(3) 0.6290(5) 1.26385(16) 0.0845(12) Uani 1 1 d . . .
H26 H 1.0601 0.6877 1.2385 0.101 Uiso 1 1 calc R . .
N1 N 1.0940(3) 0.6036(4) 1.31447(14) 0.0979(11) Uani 1 1 d . . .
C27 C 1.0538(5) 0.5175(5) 1.34857(17) 0.0919(14) Uani 1 1 d . . .
H27 H 1.0954 0.4961 1.3839 0.110 Uiso 1 1 calc R . .
C35 C 1.5093(4) 0.6480(5) 0.8764(3) 0.1008(15) Uani 1 1 d . . .
H35 H 1.5572 0.6105 0.8568 0.121 Uiso 1 1 calc R . .
C36 C 1.4752(3) 0.7335(5) 0.95751(19) 0.0884(12) Uani 1 1 d . . .
H36 H 1.4969 0.7583 0.9958 0.106 Uiso 1 1 calc R . .
C29 C 0.6318(2) 0.2484(3) 0.83919(14) 0.0659(15) Uani 0.791(4) 1 d PG A 1
C30 C 0.5836(2) 0.2437(3) 0.88550(13) 0.0845(16) Uani 0.791(4) 1 d PG A 1
H30 H 0.5978 0.3150 0.9137 0.101 Uiso 0.791(4) 1 calc PR A 1
N3 N 0.5142(2) 0.1324(4) 0.88963(15) 0.115(2) Uani 0.791(4) 1 d PG A 1
C31 C 0.4931(3) 0.0259(4) 0.8475(2) 0.134(3) Uani 0.791(4) 1 d PG A 1
H31 H 0.4466 -0.0485 0.8502 0.160 Uiso 0.791(4) 1 calc PR A 1
N4 N 0.5413(3) 0.0307(4) 0.80115(17) 0.158(4) Uani 0.791(4) 1 d PG A 1
C32 C 0.6106(3) 0.1419(4) 0.79702(13) 0.108(2) Uani 0.791(4) 1 d PG A 1
H32 H 0.6429 0.1451 0.7660 0.130 Uiso 0.791(4) 1 calc PR A 1
C29B C 0.6490(3) 0.2483(4) 0.81791(16) 0.050(5) Uani 0.209(4) 1 d PG A 2
C30B C 0.6958(2) 0.1096(4) 0.84289(19) 0.076(6) Uani 0.209(4) 1 d PG A 2
H30B H 0.7627 0.1138 0.8645 0.091 Uiso 0.209(4) 1 calc PR A 2
N3B N 0.6499(3) -0.0197(3) 0.8369(2) 0.147(8) Uani 0.209(4) 1 d PGU A 2
C31B C 0.5351(3) 0.0065(3) 0.80934(19) 0.078(8) Uani 0.209(4) 1 d PGU A 2
H31B H 0.4927 -0.0752 0.8072 0.093 Uiso 0.209(4) 1 calc PR A 2
N4B N 0.4822(3) 0.1446(5) 0.78554(15) 0.136(8) Uani 0.209(4) 1 d PGU A 2
C32B C 0.5401(3) 0.2444(4) 0.78837(13) 0.071(5) Uani 0.209(4) 1 d PGU A 2
H32B H 0.5137 0.3296 0.7698 0.085 Uiso 0.209(4) 1 calc PR 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(4) . ?
C1 C6 1.393(4) . ?
C1 C7 1.480(4) . ?
C13 C18 1.382(4) . ?
C13 C14 1.395(4) . ?
C13 C3 1.481(4) . ?
C4 C3 1.384(4) . ?
C4 C5 1.394(4) . ?
C20 C19 1.389(4) . ?
C20 C21 1.399(4) . ?
C3 C2 1.389(4) . ?
C7 C8 1.389(4) . ?
C7 C12 1.390(4) . ?
C19 C24 1.392(4) . ?
C19 C5 1.482(4) . ?
C5 C6 1.393(4) . ?
C8 C9 1.395(4) . ?
C24 C23 1.379(5) . ?
C14 C15 1.383(4) . ?
C21 C22 1.365(5) . ?
C21 C33 1.483(5) . ?
C12 C11 1.380(5) . ?
C9 C10 1.384(5) . ?
C9 C25 1.474(5) . ?
C23 C22 1.383(5) . ?
C15 C29B 1.352(5) . ?
C15 C16 1.373(5) . ?
C15 C29 1.516(4) . ?
C10 C11 1.374(5) . ?
C25 C26 1.371(5) . ?
C25 C28 1.385(5) . ?
C33 C34 1.370(5) . ?
C33 C36 1.383(5) . ?
C18 C17 1.381(5) . ?
N5 C35 1.335(6) . ?
N5 C34 1.340(5) . ?
N2 C27 1.309(6) . ?
N2 C28 1.332(5) . ?
N6 C35 1.318(6) . ?
N6 C36 1.321(5) . ?
C17 C16 1.373(6) . ?
C26 N1 1.324(5) . ?
N1 C27 1.324(5) . ?
C29 C30 1.3900 . ?
C29 C32 1.3900 . ?
C30 N3 1.3900 . ?
N3 C31 1.3900 . ?
C31 N4 1.3900 . ?
N4 C32 1.3900 . ?
C29B C32B 1.4684 . ?
C29B C30B 1.4842 . ?
C30B N3B 1.3257 . ?
N3B C31B 1.5454 . ?
C31B N4B 1.5004 . ?
N4B C32B 1.1876 . ?

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 C6 118.2(3) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C7 121.5(3) . . ?
C18 C13 C14 117.3(3) . . ?
C18 C13 C3 122.0(3) . . ?
C14 C13 C3 120.6(3) . . ?
C3 C4 C5 121.8(3) . . ?
C19 C20 C21 121.6(3) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 C13 121.3(3) . . ?
C2 C3 C13 120.3(3) . . ?
C8 C7 C12 117.8(3) . . ?
C8 C7 C1 121.3(3) . . ?
C12 C7 C1 120.9(3) . . ?
C3 C2 C1 121.8(3) . . ?
C20 C19 C24 117.8(3) . . ?
C20 C19 C5 121.0(3) . . ?
C24 C19 C5 121.2(3) . . ?
C6 C5 C4 118.4(3) . . ?
C6 C5 C19 121.1(3) . . ?
C4 C5 C19 120.5(3) . . ?
C5 C6 C1 121.4(3) . . ?
C7 C8 C9 122.0(3) . . ?
C23 C24 C19 120.9(3) . . ?
C15 C14 C13 122.2(3) . . ?
C22 C21 C20 118.7(3) . . ?
C22 C21 C33 120.8(3) . . ?
C20 C21 C33 120.5(3) . . ?
C11 C12 C7 120.4(3) . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 C25 119.9(3) . . ?
C8 C9 C25 121.3(3) . . ?
C24 C23 C22 120.0(3) . . ?
C29B C15 C16 104.8(3) . . ?
C29B C15 C14 135.7(3) . . ?
C16 C15 C14 118.8(3) . . ?
C29B C15 C29 23.22(7) . . ?
C16 C15 C29 124.6(3) . . ?
C14 C15 C29 116.4(3) . . ?
C11 C10 C9 119.6(3) . . ?
C26 C25 C28 113.6(3) . . ?
C26 C25 C9 123.8(3) . . ?
C28 C25 C9 122.5(4) . . ?
C34 C33 C36 114.6(3) . . ?
C34 C33 C21 123.0(3) . . ?
C36 C33 C21 122.4(3) . . ?
C17 C18 C13 120.9(3) . . ?
C35 N5 C34 114.4(4) . . ?
C27 N2 C28 115.7(4) . . ?
C10 C11 C12 121.4(3) . . ?
C21 C22 C23 120.9(3) . . ?
C35 N6 C36 114.9(4) . . ?
C16 C17 C18 120.6(3) . . ?
N2 C28 C25 123.8(4) . . ?
C15 C16 C17 120.2(3) . . ?
N5 C34 C33 123.9(4) . . ?
N1 C26 C25 124.7(4) . . ?
C26 N1 C27 115.2(4) . . ?
N2 C27 N1 126.9(4) . . ?
N6 C35 N5 127.9(4) . . ?
N6 C36 C33 124.4(4) . . ?
C30 C29 C32 120.0 . . ?
C30 C29 C15 121.4(3) . . ?
C32 C29 C15 118.6(3) . . ?
N3 C30 C29 120.0 . . ?
C31 N3 C30 120.0 . . ?
N3 C31 N4 120.0 . . ?
C32 N4 C31 120.0 . . ?
N4 C32 C29 120.0 . . ?
C15 C29B C32B 124.4(3) . . ?
C15 C29B C30B 117.3(3) . . ?
C32B C29B C30B 117.3 . . ?
N3B C30B C29B 125.3 . . ?
C30B N3B C31B 107.2 . . ?
N4B C31B N3B 129.3 . . ?
C32B N4B C31B 112.5 . . ?
N4B C32B C29B 127.2 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        21.92
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.069
_exptl_crystal_recrystallization_method Sublimation
_chemical_compound_source        no
_chemical_properties_physical    no
