# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_dsak-50_rep
_database_code_depnum_ccdc_archive 'CCDC 1039505'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C27 H13 N5 O, 2(C H4 O)'
_chemical_formula_sum            'C29 H21 N5 O3'
_chemical_compound_source        Synthesized
_exptl_crystal_recrystallization_method 'DCM Methanol mixture'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         487.508

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a c d'
_symmetry_space_group_name_Hall  '-I 4bd 2c'
_symmetry_int_tables_number      142
_chemical_absolute_configuration syn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z+1/2'
'-x+1/2, y, -z'
'y+3/4, x+1/4, -z+1/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1'
'-x+1, y+1/2, -z+1/2'
'y+5/4, x+3/4, -z+3/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z-1/2'
'x-1/2, -y, z'
'-y-3/4, -x-1/4, z-1/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-y-1/4, -x+1/4, z+1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   28.2864(11)
_cell_length_b                   28.2864(11)
_cell_length_c                   13.3571(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     10687.3(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4064
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8269
_exptl_absorpt_correction_T_max  0.9371
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            12797
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         66.27
_reflns_number_total             2335
_reflns_number_gt                1872
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1257P)²+21.7595P] 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     SHELXL
_refine_ls_extinction_coef       0.00001(0)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2335
_refine_ls_number_parameters     185
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.2301
_refine_ls_wR_factor_gt          0.2152
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.077
_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
N1B N 0.37867(8) 0.56788(10) 0.53033(17) 0.0413(7) Uani 1 1 d . . .
H1B H 0.3839 0.5405 0.5560 0.050 Uiso 1 1 calc R . .
N N 0.33934(9) 0.62714(9) 0.45784(18) 0.0413(7) Uani 1 1 d . . .
C C 0.2500 0.58050(14) 0.5000 0.0353(9) Uani 1 2 d S . .
H0 H 0.2500 0.6134 0.5000 0.042 Uiso 1 2 calc SR . .
C1 C 0.29271(10) 0.55629(10) 0.49723(18) 0.0363(7) Uani 1 1 d . . .
C2 C 0.2500 0.48217(15) 0.5000 0.0426(11) Uani 1 2 d S . .
C3 C 0.29277(11) 0.50695(11) 0.49829(19) 0.0400(7) Uani 1 1 d . . .
H3 H 0.3213 0.4906 0.4979 0.048 Uiso 1 1 calc R . .
C2AA C 0.41098(11) 0.60374(12) 0.5187(2) 0.0440(8) Uani 1 1 d . . .
C3AA C 0.33684(10) 0.58383(11) 0.49356(19) 0.0372(7) Uani 1 1 d . . .
C4AA C 0.38626(11) 0.64052(12) 0.4717(2) 0.0441(8) Uani 1 1 d . . .
C5AA C 0.40942(13) 0.68263(13) 0.4478(3) 0.0559(9) Uani 1 1 d . . .
H5AA H 0.3938 0.7072 0.4155 0.067 Uiso 1 1 calc R . .
C6AA C 0.45838(12) 0.60779(15) 0.5451(3) 0.0571(10) Uani 1 1 d . . .
H6AA H 0.4744 0.5833 0.5769 0.069 Uiso 1 1 calc R . .
N3 N 0.2500 0.43262(16) 0.5000 0.0763(17) Uani 1 2 d S . .
C8AA C 0.48044(14) 0.64986(17) 0.5218(3) 0.0688(12) Uani 1 1 d . . .
H8AA H 0.5121 0.6539 0.5384 0.083 Uiso 1 1 calc R . .
C9AA C 0.45643(14) 0.68632(15) 0.4740(3) 0.0662(11) Uani 1 1 d . . .
H9AA H 0.4726 0.7141 0.4593 0.079 Uiso 1 1 calc R . .
C5 C 0.2744(3) 0.4042(3) 0.5105(4) 0.0467(15) Uani 0.50 1 d PU . .
O1 O 0.40699(9) 0.47819(10) 0.5789(2) 0.0713(9) Uani 1 1 d . . .
C20A C 0.43921(14) 0.45946(15) 0.5098(3) 0.0658(11) Uani 1 1 d . . .
H20A H 0.4457 0.4826 0.4589 0.099 Uiso 1 1 calc R . .
H20B H 0.4260 0.4317 0.4795 0.099 Uiso 1 1 calc R . .
H20C H 0.4680 0.4513 0.5435 0.099 Uiso 1 1 calc R . .
O1A O 0.31717(19) 0.36063(19) 0.5245(4) 0.0609(13) Uani 0.50 1 d P . .
C23 C 0.2500 0.2547(2) 0.5000 0.0793(18) Uani 1 2 d SU . .
C22 C 0.2919(2) 0.27852(18) 0.5172(3) 0.0993(18) Uani 1 1 d U . .
C21 C 0.2912(4) 0.3280(2) 0.5169(4) 0.143(3) Uani 1 1 d U . .
C24 C 0.2500 0.3530(3) 0.5000 0.168(5) Uani 1 2 d SU . .
H1C H 0.3977(15) 0.4544(16) 0.620(4) 0.080(13) Uiso 1 1 d . . .

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
N1B 0.0418(14) 0.0538(15) 0.0284(12) 0.0099(11) 0.0042(10) 0.0082(11)
N 0.0450(14) 0.0466(15) 0.0322(13) 0.0046(10) -0.0037(10) -0.0005(11)
C 0.049(2) 0.036(2) 0.0210(17) 0.000 -0.0044(16) 0.000
C1 0.0468(17) 0.0433(16) 0.0187(13) 0.0017(11) -0.0016(11) 0.0032(12)
C2 0.071(3) 0.039(2) 0.0175(19) 0.000 0.0046(17) 0.000
C3 0.0561(19) 0.0439(17) 0.0201(13) 0.0019(11) 0.0036(12) 0.0079(13)
C2AA 0.0413(16) 0.062(2) 0.0291(14) 0.0050(13) 0.0049(12) 0.0043(14)
C3AA 0.0417(16) 0.0494(17) 0.0206(13) 0.0024(12) -0.0003(11) 0.0052(12)
C4AA 0.0456(17) 0.0541(18) 0.0325(15) -0.0014(13) 0.0015(12) -0.0017(14)
C5AA 0.057(2) 0.054(2) 0.057(2) 0.0025(16) 0.0004(16) -0.0075(16)
C6AA 0.0422(18) 0.084(3) 0.0454(18) 0.0050(17) 0.0031(15) 0.0057(17)
N3 0.162(6) 0.038(2) 0.028(2) 0.000 0.023(3) 0.000
C8AA 0.0440(19) 0.098(3) 0.064(2) 0.000(2) 0.0032(17) -0.008(2)
C9AA 0.056(2) 0.072(3) 0.070(3) 0.000(2) 0.0050(19) -0.0151(19)
C5 0.066(4) 0.055(4) 0.019(3) -0.003(3) 0.001(3) 0.005(3)
O1 0.0682(17) 0.0709(17) 0.0749(18) 0.0401(15) 0.0384(14) 0.0293(13)
C20A 0.066(2) 0.080(3) 0.051(2) 0.0163(19) 0.0190(18) 0.018(2)
O1A 0.068(3) 0.061(3) 0.053(3) -0.006(2) -0.001(2) -0.010(2)
C23 0.149(6) 0.049(3) 0.040(3) 0.000 0.003(3) 0.000
C22 0.184(6) 0.076(3) 0.038(2) -0.007(2) 0.014(3) -0.030(3)
C21 0.313(10) 0.075(3) 0.042(2) -0.018(3) 0.047(4) -0.077(5)
C24 0.423(16) 0.039(4) 0.041(4) 0.000 0.075(7) 0.000

_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
N1B C3AA 1.358(4) . ?
N1B C2AA 1.374(4) . ?
N C3AA 1.317(4) . ?
N C4AA 1.392(4) . ?
C C1 1.389(3) 6_556 ?
C C1 1.389(3) . ?
C1 C3 1.396(4) . ?
C1 C3AA 1.472(4) . ?
C2 C3 1.398(4) . ?
C2 C3 1.398(4) 6_556 ?
C2 N3 1.402(6) . ?
C2AA C6AA 1.391(5) . ?
C2AA C4AA 1.402(5) . ?
C4AA C5AA 1.396(5) . ?
C5AA C9AA 1.379(5) . ?
C6AA C8AA 1.379(6) . ?
N3 C5 1.069(7) 6_556 ?
N3 C5 1.069(7) . ?
C8AA C9AA 1.390(6) . ?
C5 C5 1.407(14) 6_556 ?
C5 C24 1.610(4) . ?
O1 C20A 1.402(4) . ?
O1A C21 1.184(4) . ?
C23 C22 1.383(6) . ?
C23 C22 1.383(6) 6_556 ?
C22 C21 1.399(7) . ?
C21 C24 1.382(10) . ?
C24 C21 1.382(10) 6_556 ?
C24 C5 1.610(10) 6_556 ?

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
C3AA N1B C2AA 107.1(2) . . ?
C3AA N C4AA 104.8(2) . . ?
C1 C C1 120.9(4) 6_556 . ?
C C1 C3 119.6(3) . . ?
C C1 C3AA 118.5(3) . . ?
C3 C1 C3AA 121.9(3) . . ?
C3 C2 C3 119.8(4) . 6_556 ?
C3 C2 N3 120.08(19) . . ?
C3 C2 N3 120.08(19) 6_556 . ?
C1 C3 C2 120.0(3) . . ?
N1B C2AA C6AA 132.3(3) . . ?
N1B C2AA C4AA 105.5(3) . . ?
C6AA C2AA C4AA 122.2(3) . . ?
N C3AA N1B 113.2(3) . . ?
N C3AA C1 123.4(3) . . ?
N1B C3AA C1 123.4(3) . . ?
N C4AA C5AA 130.4(3) . . ?
N C4AA C2AA 109.5(3) . . ?
C5AA C4AA C2AA 120.1(3) . . ?
C9AA C5AA C4AA 117.3(3) . . ?
C8AA C6AA C2AA 116.7(4) . . ?
C5 N3 C5 82.3(8) 6_556 . ?
C5 N3 C2 138.8(4) 6_556 . ?
C5 N3 C2 138.8(4) . . ?
C6AA C8AA C9AA 121.5(4) . . ?
C5AA C9AA C8AA 122.1(4) . . ?
N3 C5 C5 48.8(4) . 6_556 ?
N3 C5 C24 112.9(6) . . ?
C5 C5 C24 64.1(3) 6_556 . ?
C22 C23 C22 121.6(7) . 6_556 ?
C23 C22 C21 118.4(7) . . ?
O1A C21 C24 97.9(5) . . ?
O1A C21 C22 140.5(11) . . ?
C24 C21 C22 121.6(8) . . ?
C21 C24 C21 118.4(8) 6_556 . ?
C21 C24 C5 146.7(6) 6_556 . ?
C21 C24 C5 94.9(4) . . ?
C21 C24 C5 94.9(4) 6_556 6_556 ?
C21 C24 C5 146.7(6) . 6_556 ?
C5 C24 C5 51.8(6) . 6_556 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        66.27
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.061

