# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_TRI_a
_database_code_depnum_ccdc_archive 'CCDC 1501310'
_audit_update_record             
;
2016-08-29 deposited with the CCDC.
2017-08-03 downloaded from the CCDC.
;
_chemical_formula_moiety         'C25 H21 N3 O3'
_chemical_formula_sum            'C25 H21 N3 O3'
_chemical_formula_weight         411.45
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_h-m   'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   7.9770(12)
_cell_length_b                   27.642(4)
_cell_length_c                   9.1543(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.212(3)
_cell_angle_gamma                90
_cell_volume                     1928.1(5)
_cell_formula_units_Z            4
_exptl_absorpt_coefficient_mu    0.095
_exptl_crystal_density_diffrn    1.4174
_exptl_crystal_F_000             864.4081
_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark Red'
_chemical_absolute_configuration ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            34919
_diffrn_reflns_theta_full        28.596730
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         0.74
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      25.34
_diffrn_measured_fraction_theta_full 0.994339
_diffrn_measured_fraction_theta_max 0.994339
_diffrn_measurement_device_type  'bruker apex-2'
_cell_measurement_temperature    255
_diffrn_radiation_probe          ?
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_correction_type   none
_cell_measurement_reflns_used    753
_diffrn_ambient_temperature      255
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -10
_reflns_limit_k_max              37
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -6
_reflns_number_gt                4092
_reflns_number_total             4918
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.492646
_refine_diff_density_min         -0.363490
_refine_diff_density_rms         0.087128
_refine_ls_d_res_high            0.742445
_refine_ls_d_res_low             13.820750
_refine_ls_goodness_of_fit_ref   1.202640
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.067393
_refine_ls_R_factor_gt           0.056083
_refine_ls_restrained_S_all      1.202640
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²+0.5614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.178031
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_refinement_flags_posn
O2 O 0.56220(15) 0.48363(4) 0.18719(14) 0.0164(3) Uani 1.000000 .
O1 O 0.28664(16) 0.63579(5) 0.68888(14) 0.0178(3) Uani 1.000000 .
H1 H 0.2360(11) 0.6140(6) 0.632(2) 0.0267(4) Uiso 1.000000 G
O3 O -0.09109(16) 0.40906(5) -0.02848(15) 0.0200(3) Uani 1.000000 .
N3 N 0.44480(19) 0.54562(5) 0.38046(16) 0.0132(3) Uani 1.000000 .
N2 N 0.23140(18) 0.57020(5) 0.47629(15) 0.0144(3) Uani 1.000000 .
N1 N 0.8294(2) 0.72052(5) 0.85038(17) 0.0183(3) Uani 1.000000 .
C13 C 0.2997(2) 0.51827(6) 0.30897(18) 0.0119(3) Uani 1.000000 .
C14 C 0.2705(2) 0.48221(6) 0.19660(17) 0.0114(3) Uani 1.000000 .
C19 C 0.2034(2) 0.40794(6) -0.03455(18) 0.0124(3) Uani 1.000000 .
C15 C 0.1009(2) 0.46227(6) 0.14681(18) 0.0123(3) Uani 1.000000 .
C18 C 0.0579(2) 0.42515(6) 0.02385(18) 0.0133(3) Uani 1.000000 .
C22 C 0.5062(2) 0.40889(6) -0.03501(18) 0.0140(3) Uani 1.000000 .
H22 H 0.6194(2) 0.42123(6) 0.00146(18) 0.0168(4) Uiso 1.000000 R
C20 C 0.3733(2) 0.42681(6) 0.02074(18) 0.0118(3) Uani 1.000000 .
C8 C 0.5127(2) 0.61232(6) 0.57541(17) 0.0134(3) Uani 1.000000 .
C12 C 0.1664(2) 0.53392(6) 0.37048(18) 0.0130(3) Uani 1.000000 .
C21 C 0.4142(2) 0.46573(6) 0.13838(18) 0.0116(3) Uani 1.000000 .
C7 C 0.6872(2) 0.62013(6) 0.57547(19) 0.0159(3) Uani 1.000000 .
H7 H 0.7327(2) 0.60108(6) 0.51251(19) 0.0191(4) Uiso 1.000000 R
C11 C 0.3983(2) 0.57670(6) 0.47918(18) 0.0135(3) Uani 1.000000 .
C25 C 0.1660(2) 0.37198(6) -0.14716(19) 0.0157(3) Uani 1.000000 .
H25 H 0.0525(2) 0.35993(6) -0.18530(19) 0.0189(4) Uiso 1.000000 R
C17 C -0.0006(2) 0.51321(6) 0.32057(19) 0.0152(3) Uani 1.000000 .
H17 H -0.0888(2) 0.52308(6) 0.36133(19) 0.0182(4) Uiso 1.000000 R
C5 C 0.7281(2) 0.68496(6) 0.76186(18) 0.0149(3) Uani 1.000000 .
C9 C 0.4501(2) 0.64118(6) 0.67621(18) 0.0140(3) Uani 1.000000 .
C24 C 0.2991(2) 0.35441(6) -0.2016(2) 0.0174(3) Uani 1.000000 .
H24 H 0.2748(2) 0.33040(6) -0.2762(2) 0.0209(4) Uiso 1.000000 R
C16 C -0.0319(2) 0.47764(6) 0.20897(18) 0.0142(3) Uani 1.000000 .
H16 H -0.1427(2) 0.46366(6) 0.17451(18) 0.0170(4) Uiso 1.000000 R
C10 C 0.5556(2) 0.67658(6) 0.76570(18) 0.0149(3) Uani 1.000000 .
H10 H 0.5109(2) 0.69527(6) 0.83000(18) 0.0178(4) Uiso 1.000000 R
C6 C 0.7930(2) 0.65479(6) 0.66490(19) 0.0169(3) Uani 1.000000 .
H6 H 0.9078(2) 0.65853(6) 0.66195(19) 0.0203(4) Uiso 1.000000 R
C23 C 0.4691(2) 0.37259(6) -0.14513(19) 0.0167(3) Uani 1.000000 .
H23 H 0.5580(2) 0.36039(6) -0.18121(19) 0.0200(4) Uiso 1.000000 R
C3 C 0.7655(2) 0.74897(6) 0.9572(2) 0.0192(4) Uani 1.000000 .
H3a H 0.7020(14) 0.72803(13) 1.0075(16) 0.0231(4) Uiso 1.000000 R
H3b H 0.8647(7) 0.7614(3) 1.0377(12) 0.0231(4) Uiso 1.000000 R
C4 C 0.6474(3) 0.79102(7) 0.8814(2) 0.0238(4) Uani 1.000000 .
H4a H 0.7133(6) 0.8133(3) 0.8397(15) 0.0357(6) Uiso 1.000000 G
H4b H 0.5500(11) 0.77888(9) 0.8008(11) 0.0357(6) Uiso 1.000000 G
H4c H 0.6048(16) 0.8073(3) 0.9560(4) 0.0357(6) Uiso 1.000000 G
C2 C 0.9952(2) 0.73683(7) 0.8289(2) 0.0217(4) Uani 1.000000 .
H2a H 0.9952(3) 0.7298(6) 0.7251(4) 0.0261(5) Uiso 1.000000 R
H2b H 1.0032(2) 0.77176(8) 0.8388(17) 0.0261(5) Uiso 1.000000 R
C1 C 1.1566(3) 0.71384(8) 0.9413(2) 0.0276(4) Uani 1.000000 .
H1a H 1.1557(11) 0.7203(5) 1.0441(2) 0.0414(6) Uiso 1.000000 G
H1b H 1.1546(11) 0.67952(10) 0.9248(12) 0.0414(6) Uiso 1.000000 G
H1c H 1.2609(3) 0.7273(4) 0.9257(12) 0.0414(6) Uiso 1.000000 G
H3 H 0.546(3) 0.5453(8) 0.358(3) 0.027(6) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C21 1.2353(19) .
O1 H1 0.8200 .
O1 C9 1.3510(19) .
O3 C18 1.226(2) .
N3 C13 1.375(2) .
N3 C11 1.375(2) .
N3 H3 0.89(2) .
N2 C12 1.384(2) .
N2 C11 1.336(2) .
N1 C5 1.374(2) .
N1 C3 1.459(2) .
N1 C2 1.464(2) .
C13 C14 1.401(2) .
C13 C12 1.410(2) .
C14 C15 1.406(2) .
C14 C21 1.472(2) .
C19 C18 1.492(2) .
C19 C20 1.400(2) .
C19 C25 1.399(2) .
C15 C18 1.486(2) .
C15 C16 1.409(2) .
C22 H22 0.9300 .
C22 C20 1.397(2) .
C22 C23 1.391(2) .
C20 C21 1.488(2) .
C8 C7 1.408(2) .
C8 C11 1.450(2) .
C8 C9 1.418(2) .
C12 C17 1.397(2) .
C7 H7 0.9300 .
C7 C6 1.376(2) .
C25 H25 0.9300 .
C25 C24 1.388(2) .
C17 H17 0.9300 .
C17 C16 1.386(2) .
C5 C10 1.406(2) .
C5 C6 1.422(2) .
C9 C10 1.389(2) .
C24 H24 0.9300 .
C24 C23 1.394(2) .
C16 H16 0.9300 .
C10 H10 0.9300 .
C6 H6 0.9300 .
C23 H23 0.9300 .
C3 H3a 0.9700 .
C3 H3b 0.9700 .
C3 C4 1.528(2) .
C4 H4a 0.9600 .
C4 H4b 0.9600 .
C4 H4c 0.9600 .
C2 H2a 0.9700 .
C2 H2b 0.9700 .
C2 C1 1.529(3) .
C1 H1a 0.9600 .
C1 H1b 0.9600 .
C1 H1c 0.9600 .

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
C9 O1 H1 109.5 . .
C11 N3 C13 107.67(13) . .
H3 N3 C13 125.4(15) . .
H3 N3 C11 126.6(15) . .
C11 N2 C12 106.02(13) . .
C3 N1 C5 121.30(14) . .
C2 N1 C5 122.55(14) . .
C2 N1 C3 115.61(14) . .
C14 C13 N3 132.40(14) . .
C12 C13 N3 105.61(13) . .
C12 C13 C14 121.98(14) . .
C15 C14 C13 116.89(14) . .
C21 C14 C13 120.49(14) . .
C21 C14 C15 122.60(14) . .
C20 C19 C18 121.60(14) . .
C25 C19 C18 118.15(14) . .
C25 C19 C20 120.25(14) . .
C18 C15 C14 120.04(14) . .
C16 C15 C14 121.16(15) . .
C16 C15 C18 118.78(14) . .
C19 C18 O3 120.75(15) . .
C15 C18 O3 121.74(14) . .
C15 C18 C19 117.51(14) . .
C20 C22 H22 120.04(9) . .
C23 C22 H22 120.04(10) . .
C23 C22 C20 119.93(15) . .
C22 C20 C19 119.63(14) . .
C21 C20 C19 120.84(13) . .
C21 C20 C22 119.53(14) . .
C11 C8 C7 123.27(14) . .
C9 C8 C7 116.88(15) . .
C9 C8 C11 119.85(14) . .
C13 C12 N2 109.34(13) . .
C17 C12 N2 130.49(14) . .
C17 C12 C13 120.17(15) . .
C14 C21 O2 120.55(14) . .
C20 C21 O2 122.20(14) . .
C20 C21 C14 117.25(13) . .
H7 C7 C8 118.68(9) . .
C6 C7 C8 122.63(15) . .
C6 C7 H7 118.68(10) . .
N2 C11 N3 111.35(14) . .
C8 C11 N3 125.43(14) . .
C8 C11 N2 123.22(14) . .
H25 C25 C19 120.18(9) . .
C24 C25 C19 119.63(15) . .
C24 C25 H25 120.18(10) . .
H17 C17 C12 120.71(9) . .
C16 C17 C12 118.57(14) . .
C16 C17 H17 120.71(9) . .
C10 C5 N1 120.81(15) . .
C6 C5 N1 121.89(15) . .
C6 C5 C10 117.30(15) . .
C8 C9 O1 121.92(15) . .
C10 C9 O1 117.32(14) . .
C10 C9 C8 120.76(15) . .
H24 C24 C25 119.86(10) . .
C23 C24 C25 120.27(15) . .
C23 C24 H24 119.86(9) . .
C17 C16 C15 121.23(15) . .
H16 C16 C15 119.39(9) . .
H16 C16 C17 119.39(9) . .
C9 C10 C5 121.88(15) . .
H10 C10 C5 119.06(9) . .
H10 C10 C9 119.06(9) . .
C5 C6 C7 120.48(15) . .
H6 C6 C7 119.76(10) . .
H6 C6 C5 119.76(10) . .
C24 C23 C22 120.27(15) . .
H23 C23 C22 119.86(10) . .
H23 C23 C24 119.86(9) . .
H3a C3 N1 109.3(4) . .
H3b C3 N1 109.3(4) . .
H3b C3 H3a 105.9(19) . .
C4 C3 N1 113.35(15) . .
C4 C3 H3a 109.3(4) . .
C4 C3 H3b 109.3(4) . .
H4a C4 C3 109.5 . .
H4b C4 C3 109.5 . .
H4b C4 H4a 109.5 . .
H4c C4 C3 109.5 . .
H4c C4 H4a 109.5 . .
H4c C4 H4b 109.5 . .
H2a C2 N1 109.4(4) . .
H2b C2 N1 109.4(4) . .
H2b C2 H2a 105.7(19) . .
C1 C2 N1 113.33(15) . .
C1 C2 H2a 109.4(4) . .
C1 C2 H2b 109.4(4) . .
H1a C1 C2 109.5 . .
H1b C1 C2 109.5 . .
H1b C1 H1a 109.5 . .
H1c C1 C2 109.5 . .
H1c C1 H1a 109.5 . .
H1c C1 H1b 109.5 . .


