# 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_aw58m
_database_code_depnum_ccdc_archive 'CCDC 1023835'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O'
_chemical_formula_sum            'C19 H17 N3 O'
_chemical_formula_weight         303.36

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   13.2058(10)
_cell_length_b                   5.2630(4)
_cell_length_c                   22.7073(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.007(10)
_cell_angle_gamma                90.00
_cell_volume                     1554.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4684
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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 SMART APEX CCD area-detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14139
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2745
_reflns_number_gt                2431
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0556P)²+0.4988P] 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         2745
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.001
_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 0.66619(13) 0.6520(4) 0.85684(8) 0.0463(4) Uani 1 1 d . . .
C2 C 0.65422(16) 0.7012(4) 0.79565(8) 0.0579(5) Uani 1 1 d . . .
H2 H 0.6890 0.6061 0.7710 0.070 Uiso 1 1 calc R . .
C3 C 0.58934(16) 0.8950(5) 0.77314(9) 0.0664(6) Uani 1 1 d . . .
H3 H 0.5800 0.9310 0.7325 0.080 Uiso 1 1 calc R . .
C4 C 0.53685(16) 1.0397(5) 0.80999(9) 0.0658(6) Uani 1 1 d . . .
H4 H 0.4936 1.1704 0.7935 0.079 Uiso 1 1 calc R . .
C5 C 0.54838(14) 0.9912(4) 0.87012(9) 0.0549(5) Uani 1 1 d . . .
H5 H 0.5137 1.0890 0.8943 0.066 Uiso 1 1 calc R . .
C6 C 0.61267(13) 0.7938(4) 0.89465(8) 0.0443(4) Uani 1 1 d . . .
C7 C 0.64330(13) 0.6938(3) 0.95352(8) 0.0417(4) Uani 1 1 d . . .
C8 C 0.71189(12) 0.5053(3) 0.94934(7) 0.0404(4) Uani 1 1 d . . .
C9 C 0.76505(12) 0.3500(3) 1.00005(7) 0.0410(4) Uani 1 1 d . . .
H9 H 0.7570 0.1706 0.9886 0.049 Uiso 1 1 calc R . .
C10 C 0.93251(14) 0.3088(4) 1.06225(9) 0.0583(5) Uani 1 1 d . . .
C11 C 0.87386(14) 0.2022(4) 1.10644(8) 0.0511(5) Uani 1 1 d . . .
C12 C 0.92317(16) 0.0615(5) 1.15494(10) 0.0655(6) Uani 1 1 d . . .
H12 H 0.9919 0.0172 1.1572 0.079 Uiso 1 1 calc R . .
C13 C 0.87111(18) -0.0125(4) 1.19953(10) 0.0663(6) Uani 1 1 d . . .
H13 H 0.9038 -0.1114 1.2312 0.080 Uiso 1 1 calc R . .
C14 C 0.77029(18) 0.0607(4) 1.19711(9) 0.0598(5) Uani 1 1 d . . .
H14 H 0.7359 0.0157 1.2280 0.072 Uiso 1 1 calc R . .
C15 C 0.71998(15) 0.1992(4) 1.14967(8) 0.0518(5) Uani 1 1 d . . .
H15 H 0.6522 0.2492 1.1488 0.062 Uiso 1 1 calc R . .
C16 C 0.77015(14) 0.2650(3) 1.10286(8) 0.0441(4) Uani 1 1 d . . .
C17 C 0.68970(15) 0.6551(4) 1.06243(8) 0.0526(5) Uani 1 1 d . . .
H17A H 0.7516 0.7575 1.0670 0.063 Uiso 1 1 calc R . .
H17B H 0.6625 0.6656 1.0994 0.063 Uiso 1 1 calc R . .
C18 C 0.61150(13) 0.7607(3) 1.01180(8) 0.0448(4) Uani 1 1 d . . .
H18A H 0.5442 0.6896 1.0133 0.054 Uiso 1 1 calc R . .
H18B H 0.6073 0.9438 1.0156 0.054 Uiso 1 1 calc R . .
C19 C 0.79233(15) 0.2901(4) 0.86908(9) 0.0572(5) Uani 1 1 d . . .
H19A H 0.7580 0.2237 0.8315 0.086 Uiso 1 1 calc R . .
H19B H 0.8069 0.1539 0.8974 0.086 Uiso 1 1 calc R . .
H19C H 0.8555 0.3698 0.8638 0.086 Uiso 1 1 calc R . .
N1 N 0.72663(11) 0.4756(3) 0.89109(6) 0.0460(4) Uani 1 1 d . . .
N2 N 0.87500(11) 0.4072(3) 1.01319(7) 0.0534(4) Uani 1 1 d . . .
N3 N 0.71561(11) 0.3902(3) 1.05177(6) 0.0431(4) Uani 1 1 d . . .
O1 O 1.02765(10) 0.3190(4) 1.07207(8) 0.0872(6) Uani 1 1 d . . .
H1N H 0.9018(17) 0.487(4) 0.9846(10) 0.065(6) 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
C1 N1 1.374(2) . ?
C1 C2 1.395(3) . ?
C1 C6 1.416(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.428(2) . ?
C7 C8 1.358(2) . ?
C7 C18 1.498(2) . ?
C8 N1 1.379(2) . ?
C8 C9 1.485(2) . ?
C9 N3 1.455(2) . ?
C9 N2 1.462(2) . ?
C9 H9 0.9800 . ?
C10 O1 1.238(2) . ?
C10 N2 1.339(3) . ?
C10 C11 1.480(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.397(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9300 . ?
C16 N3 1.417(2) . ?
C17 N3 1.465(2) . ?
C17 C18 1.511(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N1 1.452(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 H1N 0.90(2) . ?

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
N1 C1 C2 130.03(17) . . ?
N1 C1 C6 108.36(15) . . ?
C2 C1 C6 121.60(18) . . ?
C3 C2 C1 117.66(19) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.55(19) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.40(19) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 118.93(17) . . ?
C5 C6 C7 134.58(17) . . ?
C1 C6 C7 106.46(16) . . ?
C8 C7 C6 106.72(15) . . ?
C8 C7 C18 121.75(16) . . ?
C6 C7 C18 131.53(16) . . ?
C7 C8 N1 110.92(16) . . ?
C7 C8 C9 125.39(15) . . ?
N1 C8 C9 123.69(15) . . ?
N3 C9 N2 111.99(14) . . ?
N3 C9 C8 109.13(14) . . ?
N2 C9 C8 111.32(14) . . ?
N3 C9 H9 108.1 . . ?
N2 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
O1 C10 N2 122.96(18) . . ?
O1 C10 C11 121.90(18) . . ?
N2 C10 C11 115.00(16) . . ?
C12 C11 C16 119.41(18) . . ?
C12 C11 C10 120.67(18) . . ?
C16 C11 C10 119.60(17) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.82(18) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.14(19) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.27(18) . . ?
C15 C16 N3 119.98(17) . . ?
C11 C16 N3 120.74(15) . . ?
N3 C17 C18 111.86(15) . . ?
N3 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N3 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C7 C18 C17 109.03(15) . . ?
C7 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
C7 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 C8 107.54(14) . . ?
C1 N1 C19 125.65(15) . . ?
C8 N1 C19 126.81(16) . . ?
C10 N2 C9 119.33(15) . . ?
C10 N2 H1N 123.0(14) . . ?
C9 N2 H1N 116.9(14) . . ?
C16 N3 C9 110.95(14) . . ?
C16 N3 C17 114.01(14) . . ?
C9 N3 C17 114.98(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
N1 C1 C2 C3 -178.67(19) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C4 C5 C6 C7 179.0(2) . . . . ?
N1 C1 C6 C5 178.01(16) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
N1 C1 C6 C7 -0.26(19) . . . . ?
C2 C1 C6 C7 -179.81(16) . . . . ?
C5 C6 C7 C8 -177.3(2) . . . . ?
C1 C6 C7 C8 0.55(19) . . . . ?
C5 C6 C7 C18 3.7(3) . . . . ?
C1 C6 C7 C18 -178.42(17) . . . . ?
C6 C7 C8 N1 -0.65(19) . . . . ?
C18 C7 C8 N1 178.44(15) . . . . ?
C6 C7 C8 C9 179.21(15) . . . . ?
C18 C7 C8 C9 -1.7(3) . . . . ?
C7 C8 C9 N3 12.8(2) . . . . ?
N1 C8 C9 N3 -167.34(14) . . . . ?
C7 C8 C9 N2 -111.29(19) . . . . ?
N1 C8 C9 N2 68.6(2) . . . . ?
O1 C10 C11 C12 -13.7(4) . . . . ?
N2 C10 C11 C12 170.5(2) . . . . ?
O1 C10 C11 C16 159.7(2) . . . . ?
N2 C10 C11 C16 -16.1(3) . . . . ?
C16 C11 C12 C13 -0.9(3) . . . . ?
C10 C11 C12 C13 172.5(2) . . . . ?
C11 C12 C13 C14 -2.2(4) . . . . ?
C12 C13 C14 C15 2.3(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 -3.9(3) . . . . ?
C14 C15 C16 N3 174.94(17) . . . . ?
C12 C11 C16 C15 3.9(3) . . . . ?
C10 C11 C16 C15 -169.56(18) . . . . ?
C12 C11 C16 N3 -174.89(18) . . . . ?
C10 C11 C16 N3 11.6(3) . . . . ?
C8 C7 C18 C17 18.3(2) . . . . ?
C6 C7 C18 C17 -162.83(17) . . . . ?
N3 C17 C18 C7 -46.8(2) . . . . ?
C2 C1 N1 C8 179.37(19) . . . . ?
C6 C1 N1 C8 -0.12(19) . . . . ?
C2 C1 N1 C19 -1.6(3) . . . . ?
C6 C1 N1 C19 178.93(16) . . . . ?
C7 C8 N1 C1 0.49(19) . . . . ?
C9 C8 N1 C1 -179.37(15) . . . . ?
C7 C8 N1 C19 -178.54(16) . . . . ?
C9 C8 N1 C19 1.6(3) . . . . ?
O1 C10 N2 C9 169.7(2) . . . . ?
C11 C10 N2 C9 -14.5(3) . . . . ?
N3 C9 N2 C10 49.1(2) . . . . ?
C8 C9 N2 C10 171.56(18) . . . . ?
C15 C16 N3 C9 -156.59(16) . . . . ?
C11 C16 N3 C9 22.2(2) . . . . ?
C15 C16 N3 C17 71.7(2) . . . . ?
C11 C16 N3 C17 -109.50(19) . . . . ?
N2 C9 N3 C16 -50.52(19) . . . . ?
C8 C9 N3 C16 -174.23(14) . . . . ?
N2 C9 N3 C17 80.71(19) . . . . ?
C8 C9 N3 C17 -43.00(19) . . . . ?
C18 C17 N3 C16 -166.68(14) . . . . ?
C18 C17 N3 C9 63.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O1 0.90(2) 2.00(2) 2.888(2) 174(2) 3_767

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
