# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1581281'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N4 O3'
_chemical_formula_weight         438.47

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.4124(14)
_cell_length_b                   12.451(3)
_cell_length_c                   14.248(3)
_cell_angle_alpha                101.099(4)
_cell_angle_beta                 102.349(4)
_cell_angle_gamma                94.856(4)
_cell_volume                     1081.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3780
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4810
_exptl_absorpt_correction_T_max  0.5520
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5550
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.499
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3780
_reflns_number_gt                2049
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0655P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_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
N2 N 0.3316(3) 0.31984(15) 0.35712(14) 0.0486(5) Uani 1 1 d . . . . .
N1 N 0.1585(3) 0.35248(16) 0.29424(14) 0.0493(5) Uani 1 1 d . . . . .
C2 C -0.1071(4) 0.46580(18) 0.26043(17) 0.0467(6) Uani 1 1 d . . . . .
O1 O -0.1360(3) 0.29717(15) 0.13844(13) 0.0781(6) Uani 1 1 d . . . . .
H1 H -0.027599 0.290644 0.178444 0.117 Uiso 1 1 calc R U . . .
O3 O 0.1293(3) 0.31005(14) 0.46864(13) 0.0617(5) Uani 1 1 d . . . . .
C11 C 0.4384(4) 0.21629(19) 0.48236(18) 0.0510(7) Uani 1 1 d . . . . .
C1 C 0.0925(4) 0.44568(19) 0.32286(17) 0.0482(6) Uani 1 1 d . . . . .
C10 C 0.2843(4) 0.28245(19) 0.43653(18) 0.0498(7) Uani 1 1 d . . . . .
N3 N 0.1606(3) 0.10990(17) 0.25610(14) 0.0526(6) Uani 1 1 d . . . . .
C4 C -0.4040(5) 0.4102(2) 0.11766(19) 0.0647(8) Uani 1 1 d . . . . .
H4 H -0.469117 0.360753 0.058803 0.078 Uiso 1 1 calc R U . . .
C16 C 0.6225(4) 0.1963(2) 0.4472(2) 0.0545(7) Uani 1 1 d . . . . .
C17 C 0.4624(4) 0.2569(2) 0.29968(19) 0.0562(7) Uani 1 1 d . . . . .
H17 H 0.511222 0.302676 0.257772 0.067 Uiso 1 1 calc R U . . .
C3 C -0.2130(4) 0.3913(2) 0.17207(18) 0.0522(7) Uani 1 1 d . . . . .
C5 C -0.5022(5) 0.5001(2) 0.1474(2) 0.0613(7) Uani 1 1 d . . . . .
C8 C -0.2102(5) 0.5568(2) 0.2883(2) 0.0626(8) Uani 1 1 d . . . . .
H8 H -0.145301 0.607604 0.346348 0.075 Uiso 1 1 calc R U . . .
O2 O -0.6955(3) 0.50791(18) 0.08793(15) 0.0870(7) Uani 1 1 d . . . . .
C18 C 0.3348(4) 0.1504(2) 0.23343(18) 0.0538(7) Uani 1 1 d . . . . .
C26 C 0.0549(4) 0.0100(2) 0.19973(18) 0.0573(7) Uani 1 1 d . . . . .
C7 C -0.4048(5) 0.5749(2) 0.2334(2) 0.0682(8) Uani 1 1 d . . . . .
H7 H -0.468683 0.636588 0.254388 0.082 Uiso 1 1 calc R U . . .
C21 C 0.1243(5) -0.0481(2) 0.1201(2) 0.0689(8) Uani 1 1 d . . . . .
C12 C 0.4097(5) 0.1785(2) 0.5646(2) 0.0654(8) Uani 1 1 d . . . . .
H12 H 0.287263 0.191159 0.587916 0.078 Uiso 1 1 calc R U . . .
C15 C 0.7745(4) 0.1401(2) 0.4960(2) 0.0711(8) Uani 1 1 d . . . . .
H15 H 0.897574 0.126952 0.473365 0.085 Uiso 1 1 calc R U . . .
C25 C -0.1297(5) -0.0358(2) 0.2242(2) 0.0750(9) Uani 1 1 d . . . . .
H25 H -0.181019 0.003137 0.275169 0.090 Uiso 1 1 calc R U . . .
C14 C 0.7426(6) 0.1044(3) 0.5771(3) 0.0841(10) Uani 1 1 d . . . . .
H14 H 0.845278 0.067202 0.609531 0.101 Uiso 1 1 calc R U . . .
C19 C 0.4126(5) 0.0995(3) 0.1538(2) 0.0753(9) Uani 1 1 d . . . . .
H19 H 0.534060 0.132594 0.139429 0.090 Uiso 1 1 calc R U . . .
C9 C 0.2072(4) 0.5302(2) 0.41317(19) 0.0683(8) Uani 1 1 d . . . . .
H9A H 0.126514 0.531937 0.462833 0.102 Uiso 1 1 calc R U . . .
H9B H 0.220713 0.601531 0.397130 0.102 Uiso 1 1 calc R U . . .
H9C H 0.347838 0.511330 0.437374 0.102 Uiso 1 1 calc R U . . .
C23 C -0.1618(8) -0.1956(3) 0.0956(3) 0.1076(14) Uani 1 1 d . . . . .
H23 H -0.232410 -0.265178 0.062312 0.129 Uiso 1 1 calc R U . . .
C22 C 0.0097(8) -0.1519(3) 0.0683(3) 0.0994(12) Uani 1 1 d . . . . .
H22 H 0.053137 -0.190698 0.014734 0.119 Uiso 1 1 calc R U . . .
C24 C -0.2332(6) -0.1371(3) 0.1730(3) 0.0979(12) Uani 1 1 d . . . . .
H24 H -0.353436 -0.167336 0.190297 0.117 Uiso 1 1 calc R U . . .
C13 C 0.5602(6) 0.1223(2) 0.6122(2) 0.0813(10) Uani 1 1 d . . . . .
H13 H 0.539635 0.096827 0.667174 0.098 Uiso 1 1 calc R U . . .
C6 C -0.7970(5) 0.6021(3) 0.1115(3) 0.0925(11) Uani 1 1 d . . . . .
H6A H -0.833623 0.604651 0.173713 0.139 Uiso 1 1 calc R U . . .
H6B H -0.925559 0.598715 0.061393 0.139 Uiso 1 1 calc R U . . .
H6C H -0.701043 0.667186 0.115424 0.139 Uiso 1 1 calc R U . . .
C20 C 0.3086(7) 0.0016(3) 0.0982(2) 0.0903(11) Uani 1 1 d . . . . .
H20 H 0.358917 -0.033254 0.045135 0.108 Uiso 1 1 calc R U . . .
N4 N 0.6484(3) 0.23374(19) 0.36442(17) 0.0676(7) Uani 1 1 d . . . . .
H4A H 0.773601 0.242842 0.352193 0.081 Uiso 1 1 calc R U . . .


_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
N2 C10 1.384(3) . ?
N2 N1 1.411(3) . ?
N2 C17 1.465(3) . ?
N1 C1 1.291(3) . ?
C2 C8 1.394(3) . ?
C2 C3 1.409(3) . ?
C2 C1 1.465(3) . ?
O1 C3 1.353(3) . ?
O3 C10 1.228(3) . ?
C11 C12 1.385(3) . ?
C11 C16 1.400(4) . ?
C11 C10 1.467(3) . ?
C1 C9 1.499(3) . ?
N3 C18 1.314(3) . ?
N3 C26 1.376(3) . ?
C4 C3 1.367(3) . ?
C4 C5 1.371(4) . ?
C16 N4 1.385(3) . ?
C16 C15 1.391(4) . ?
C17 N4 1.430(3) . ?
C17 C18 1.524(3) . ?
C5 O2 1.366(3) . ?
C5 C7 1.376(4) . ?
C8 C7 1.385(4) . ?
O2 C6 1.408(4) . ?
C18 C19 1.398(4) . ?
C26 C21 1.400(4) . ?
C26 C25 1.409(4) . ?
C21 C20 1.410(4) . ?
C21 C22 1.413(4) . ?
C12 C13 1.377(4) . ?
C15 C14 1.363(4) . ?
C25 C24 1.364(4) . ?
C14 C13 1.385(4) . ?
C19 C20 1.351(4) . ?
C23 C22 1.348(5) . ?
C23 C24 1.385(5) . ?

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
C10 N2 N1 116.04(19) . . ?
C10 N2 C17 118.3(2) . . ?
N1 N2 C17 110.49(19) . . ?
C1 N1 N2 119.0(2) . . ?
C8 C2 C3 116.1(2) . . ?
C8 C2 C1 121.7(2) . . ?
C3 C2 C1 122.2(2) . . ?
C12 C11 C16 119.3(3) . . ?
C12 C11 C10 120.2(3) . . ?
C16 C11 C10 120.4(2) . . ?
N1 C1 C2 115.5(2) . . ?
N1 C1 C9 124.0(2) . . ?
C2 C1 C9 120.5(2) . . ?
O3 C10 N2 120.6(2) . . ?
O3 C10 C11 123.5(3) . . ?
N2 C10 C11 115.7(2) . . ?
C18 N3 C26 117.4(2) . . ?
C3 C4 C5 121.8(3) . . ?
N4 C16 C15 121.7(3) . . ?
N4 C16 C11 118.7(2) . . ?
C15 C16 C11 119.6(3) . . ?
N4 C17 N2 109.7(2) . . ?
N4 C17 C18 110.5(2) . . ?
N2 C17 C18 112.1(2) . . ?
O1 C3 C4 116.9(2) . . ?
O1 C3 C2 122.3(2) . . ?
C4 C3 C2 120.7(3) . . ?
O2 C5 C4 116.1(3) . . ?
O2 C5 C7 124.4(3) . . ?
C4 C5 C7 119.4(3) . . ?
C7 C8 C2 123.0(3) . . ?
C5 O2 C6 118.6(2) . . ?
N3 C18 C19 123.7(3) . . ?
N3 C18 C17 117.9(2) . . ?
C19 C18 C17 118.3(3) . . ?
N3 C26 C21 122.8(3) . . ?
N3 C26 C25 118.2(2) . . ?
C21 C26 C25 119.0(3) . . ?
C5 C7 C8 119.0(3) . . ?
C26 C21 C20 116.8(3) . . ?
C26 C21 C22 118.9(3) . . ?
C20 C21 C22 124.3(3) . . ?
C13 C12 C11 120.9(3) . . ?
C14 C15 C16 119.9(3) . . ?
C24 C25 C26 120.0(3) . . ?
C15 C14 C13 121.3(3) . . ?
C20 C19 C18 119.0(3) . . ?
C22 C23 C24 120.3(4) . . ?
C23 C22 C21 120.8(4) . . ?
C25 C24 C23 120.9(4) . . ?
C12 C13 C14 119.1(3) . . ?
C19 C20 C21 120.3(3) . . ?
C16 N4 C17 118.6(2) . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.037



