# 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_2m
_database_code_depnum_ccdc_archive 'CCDC 1423000'
_audit_update_record             
;
2015-09-08 deposited with the CCDC.
2015-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 N5 O'
_chemical_formula_weight         399.49

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'

_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                   8.249(3)
_cell_length_b                   9.685(3)
_cell_length_c                   14.060(5)
_cell_angle_alpha                94.073(6)
_cell_angle_beta                 91.653(6)
_cell_angle_gamma                107.489(6)
_cell_volume                     1067.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    571(2)
_cell_measurement_reflns_used    3138
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      24.95

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   BRUKARSADBAS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      571(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 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10389
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.17
_reflns_number_total             3797
_reflns_number_gt                2855
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0735P)²+0.0273P] 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         3797
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.004
_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
N10 N 0.11170(16) 0.69424(13) 0.12100(9) 0.0517(3) Uani 1 1 d . . .
N9 N 0.53523(15) 0.51195(13) 0.21514(8) 0.0491(3) Uani 1 1 d . . .
N1 N 0.15960(17) 0.67831(14) 0.28639(8) 0.0566(3) Uani 1 1 d . . .
N3 N 0.38497(17) 0.58860(14) 0.34519(8) 0.0580(4) Uani 1 1 d . . .
N7 N 0.39033(16) 0.56106(14) 0.09099(8) 0.0529(3) Uani 1 1 d . . .
C24 C -0.01037(19) 0.74718(16) -0.06387(10) 0.0506(4) Uani 1 1 d . . .
C23 C -0.07966(18) 0.78480(15) 0.02774(10) 0.0469(4) Uani 1 1 d . . .
C26 C 0.00561(18) 0.74641(17) -0.24370(10) 0.0523(4) Uani 1 1 d . . .
H26A H 0.1256 0.8011 -0.2375 0.063 Uiso 1 1 calc R . .
H26B H -0.0036 0.6439 -0.2479 0.063 Uiso 1 1 calc R . .
C18 C -0.01838(18) 0.75887(14) 0.11812(10) 0.0463(4) Uani 1 1 d . . .
C25 C -0.08017(18) 0.78274(16) -0.15575(10) 0.0493(4) Uani 1 1 d . . .
H25A H -0.0686 0.8857 -0.1514 0.059 Uiso 1 1 calc R . .
H25B H -0.2007 0.7302 -0.1633 0.059 Uiso 1 1 calc R . .
C19 C -0.08914(19) 0.79993(16) 0.20036(11) 0.0542(4) Uani 1 1 d . . .
H19 H -0.0487 0.7848 0.2599 0.065 Uiso 1 1 calc R . .
C12 C 0.57329(17) 0.31210(17) 0.30279(11) 0.0506(4) Uani 1 1 d . . .
C22 C -0.21026(19) 0.84888(16) 0.02606(11) 0.0565(4) Uani 1 1 d . . .
H22 H -0.2521 0.8663 -0.0326 0.068 Uiso 1 1 calc R . .
C20 C -0.2173(2) 0.86224(17) 0.19444(12) 0.0604(4) Uani 1 1 d . . .
H20 H -0.2633 0.8882 0.2500 0.072 Uiso 1 1 calc R . .
C13 C 0.5474(2) 0.29854(19) 0.39839(11) 0.0608(4) Uani 1 1 d . . .
H13 H 0.5831 0.3805 0.4415 0.073 Uiso 1 1 calc R . .
C27 C -0.07194(19) 0.78062(18) -0.33458(10) 0.0574(4) Uani 1 1 d . . .
H27A H -0.1920 0.7263 -0.3401 0.069 Uiso 1 1 calc R . .
H27B H -0.0627 0.8831 -0.3299 0.069 Uiso 1 1 calc R . .
C17 C 0.5189(2) 0.18931(18) 0.23942(13) 0.0645(4) Uani 1 1 d . . .
H17 H 0.5362 0.1965 0.1747 0.077 Uiso 1 1 calc R . .
C11 C 0.65647(19) 0.45777(17) 0.26690(11) 0.0574(4) Uani 1 1 d . . .
H11A H 0.7093 0.5268 0.3206 0.069 Uiso 1 1 calc R . .
H11B H 0.7453 0.4501 0.2250 0.069 Uiso 1 1 calc R . .
C21 C -0.2790(2) 0.88698(18) 0.10751(12) 0.0635(4) Uani 1 1 d . . .
H21 H -0.3663 0.9291 0.1041 0.076 Uiso 1 1 calc R . .
C14 C 0.4693(2) 0.1653(2) 0.43112(15) 0.0769(5) Uani 1 1 d . . .
H14 H 0.4540 0.1574 0.4960 0.092 Uiso 1 1 calc R . .
C28 C 0.0101(2) 0.7455(3) -0.42391(12) 0.0838(6) Uani 1 1 d . . .
H28A H 0.0110 0.6455 -0.4256 0.101 Uiso 1 1 calc R . .
H28B H 0.1273 0.8071 -0.4216 0.101 Uiso 1 1 calc R . .
C16 C 0.4384(2) 0.0553(2) 0.27256(17) 0.0819(6) Uani 1 1 d . . .
H16 H 0.4007 -0.0272 0.2301 0.098 Uiso 1 1 calc R . .
C15 C 0.4147(2) 0.0454(2) 0.36868(18) 0.0854(6) Uani 1 1 d . . .
H15 H 0.3608 -0.0443 0.3910 0.102 Uiso 1 1 calc R . .
C29 C -0.0804(3) 0.7665(4) -0.51409(13) 0.1266(10) Uani 1 1 d . . .
H29A H -0.1938 0.7001 -0.5194 0.190 Uiso 1 1 calc R . .
H29B H -0.0195 0.7483 -0.5683 0.190 Uiso 1 1 calc R . .
H29C H -0.0855 0.8644 -0.5118 0.190 Uiso 1 1 calc R . .
O1 O 0.10280(15) 0.68910(14) -0.06628(7) 0.0738(4) Uani 1 1 d . . .
C6 C 0.19632(18) 0.65785(15) 0.19511(9) 0.0463(3) Uani 1 1 d . . .
C5 C 0.32655(18) 0.59747(14) 0.17570(9) 0.0449(3) Uani 1 1 d . . .
C4 C 0.41398(18) 0.56709(14) 0.25294(10) 0.0460(3) Uani 1 1 d . . .
C2 C 0.2558(2) 0.64244(18) 0.35347(10) 0.0628(4) Uani 1 1 d . . .
H2 H 0.2269 0.6580 0.4159 0.075 Uiso 1 1 calc R . .
C8 C 0.51284(19) 0.51099(16) 0.11875(10) 0.0541(4) Uani 1 1 d . . .
H8 H 0.5794 0.4774 0.0761 0.065 Uiso 1 1 calc R . .
H10A H 0.144(2) 0.6740(17) 0.0597(12) 0.073(5) Uiso 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
N10 C6 1.3621(18) . ?
N10 C18 1.3964(19) . ?
N9 C8 1.3615(19) . ?
N9 C4 1.3710(18) . ?
N9 C11 1.4604(18) . ?
N1 C6 1.3418(18) . ?
N1 C2 1.3451(19) . ?
N3 C2 1.3240(19) . ?
N3 C4 1.3389(18) . ?
N7 C8 1.3066(18) . ?
N7 C5 1.3812(17) . ?
C24 O1 1.2263(17) . ?
C24 C23 1.490(2) . ?
C24 C25 1.503(2) . ?
C23 C22 1.396(2) . ?
C23 C18 1.421(2) . ?
C26 C27 1.514(2) . ?
C26 C25 1.514(2) . ?
C18 C19 1.396(2) . ?
C19 C20 1.369(2) . ?
C12 C13 1.376(2) . ?
C12 C17 1.384(2) . ?
C12 C11 1.502(2) . ?
C22 C21 1.368(2) . ?
C20 C21 1.374(2) . ?
C13 C14 1.376(2) . ?
C27 C28 1.509(2) . ?
C17 C16 1.388(2) . ?
C14 C15 1.356(3) . ?
C28 C29 1.510(2) . ?
C16 C15 1.377(3) . ?
C6 C5 1.394(2) . ?
C5 C4 1.3834(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
C6 N10 C18 131.94(13) . . ?
C8 N9 C4 105.48(12) . . ?
C8 N9 C11 127.11(13) . . ?
C4 N9 C11 127.33(12) . . ?
C6 N1 C2 117.00(13) . . ?
C2 N3 C4 110.11(12) . . ?
C8 N7 C5 103.43(12) . . ?
O1 C24 C23 121.85(13) . . ?
O1 C24 C25 119.16(14) . . ?
C23 C24 C25 118.99(13) . . ?
C22 C23 C18 117.72(13) . . ?
C22 C23 C24 119.36(13) . . ?
C18 C23 C24 122.92(13) . . ?
C27 C26 C25 112.39(12) . . ?
C19 C18 N10 122.63(13) . . ?
C19 C18 C23 118.93(14) . . ?
N10 C18 C23 118.43(12) . . ?
C24 C25 C26 114.36(12) . . ?
C20 C19 C18 120.83(14) . . ?
C13 C12 C17 118.96(15) . . ?
C13 C12 C11 120.91(15) . . ?
C17 C12 C11 120.12(15) . . ?
C21 C22 C23 122.39(15) . . ?
C19 C20 C21 120.96(15) . . ?
C14 C13 C12 120.90(17) . . ?
C28 C27 C26 113.94(14) . . ?
C12 C17 C16 119.97(17) . . ?
N9 C11 C12 112.20(12) . . ?
C22 C21 C20 119.16(15) . . ?
C15 C14 C13 119.96(19) . . ?
C27 C28 C29 112.88(16) . . ?
C15 C16 C17 119.63(18) . . ?
C14 C15 C16 120.57(19) . . ?
N1 C6 N10 122.53(14) . . ?
N1 C6 C5 118.55(13) . . ?
N10 C6 C5 118.92(13) . . ?
N7 C5 C4 110.74(13) . . ?
N7 C5 C6 131.98(13) . . ?
C4 C5 C6 117.28(13) . . ?
N3 C4 N9 127.80(13) . . ?
N3 C4 C5 126.43(14) . . ?
N9 C4 C5 105.77(12) . . ?
N3 C2 N1 130.58(14) . . ?
N7 C8 N9 114.58(13) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.17
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.060
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
