# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_xb7437_0m
_audit_block_doi                 10.5517/cc1355q5
_database_code_depnum_ccdc_archive 'CCDC 1017876'
_audit_update_record             
;
2014-08-04 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30

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                   7.6501(19)
_cell_length_b                   17.931(4)
_cell_length_c                   10.515(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.674(4)
_cell_angle_gamma                90.00
_cell_volume                     1374.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_process_details   '(sadabs; Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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         0
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6793
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2440
_reflns_number_gt                1916
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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)+(0.0651P)²+0.0000P] 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       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2440
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.321
_refine_ls_restrained_S_all      1.321
_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
N1 N 0.4366(3) 0.15478(9) 0.77399(18) 0.0451(5) Uani 1 1 d . . .
H1A H 0.5545 0.1569 0.8005 0.054 Uiso 1 1 calc R . .
O3 O 0.2857(2) -0.04385(7) 0.26494(14) 0.0435(4) Uani 1 1 d . . .
O2 O 0.1739(2) 0.00690(8) 0.83459(15) 0.0543(5) Uani 1 1 d . . .
O1 O 0.2188(2) 0.14941(7) 0.55028(14) 0.0468(5) Uani 1 1 d . . .
C16 C 0.2671(4) 0.00713(14) 0.1578(2) 0.0559(7) Uani 1 1 d . . .
H16A H 0.1505 0.0318 0.1377 0.084 Uiso 1 1 calc R . .
H16B H 0.2745 -0.0195 0.0804 0.084 Uiso 1 1 calc R . .
H16C H 0.3637 0.0435 0.1830 0.084 Uiso 1 1 calc R . .
C7 C 0.2657(3) -0.01794(11) 0.38060(19) 0.0345(5) Uani 1 1 d . . .
C8 C 0.2513(3) 0.05583(10) 0.40853(19) 0.0359(5) Uani 1 1 d . . .
H8 H 0.2513 0.0924 0.3459 0.043 Uiso 1 1 calc R . .
C9 C 0.2367(3) 0.07451(10) 0.53171(19) 0.0351(5) Uani 1 1 d . . .
C4 C 0.2349(3) 0.02229(10) 0.62867(19) 0.0331(5) Uani 1 1 d . . .
C5 C 0.2455(3) -0.05386(10) 0.59609(19) 0.0335(5) Uani 1 1 d . . .
C6 C 0.2622(3) -0.07203(11) 0.47428(19) 0.0363(5) Uani 1 1 d . . .
H6 H 0.2714 -0.1220 0.4534 0.044 Uiso 1 1 calc R . .
C17 C 0.2405(3) -0.11593(11) 0.6911(2) 0.0480(6) Uani 1 1 d . . .
H17A H 0.1215 -0.1176 0.7039 0.072 Uiso 1 1 calc R . .
H17B H 0.3321 -0.1072 0.7752 0.072 Uiso 1 1 calc R . .
H17C H 0.2647 -0.1625 0.6548 0.072 Uiso 1 1 calc R . .
C3 C 0.2192(3) 0.04672(10) 0.7580(2) 0.0355(5) Uani 1 1 d . . .
C2 C 0.2649(3) 0.12666(10) 0.7941(2) 0.0355(5) Uani 1 1 d . . .
C1 C 0.2686(3) 0.17553(11) 0.6802(2) 0.0417(6) Uani 1 1 d . . .
H1 H 0.2324 0.2273 0.6886 0.050 Uiso 1 1 calc R . .
C10 C 0.2196(3) 0.15770(10) 0.9116(2) 0.0357(5) Uani 1 1 d . . .
C11 C 0.0411(3) 0.15693(12) 0.9151(2) 0.0463(6) Uani 1 1 d . . .
H11 H -0.0515 0.1374 0.8438 0.056 Uiso 1 1 calc R . .
C12 C -0.0004(4) 0.18512(14) 1.0244(3) 0.0584(7) Uani 1 1 d . . .
H12 H -0.1209 0.1841 1.0267 0.070 Uiso 1 1 calc R . .
C13 C 0.1343(4) 0.21467(13) 1.1296(2) 0.0576(7) Uani 1 1 d . . .
H13 H 0.1058 0.2338 1.2031 0.069 Uiso 1 1 calc R . .
C14 C 0.3101(4) 0.21567(13) 1.1254(2) 0.0555(7) Uani 1 1 d . . .
H14 H 0.4023 0.2352 1.1970 0.067 Uiso 1 1 calc R . .
C15 C 0.3533(3) 0.18808(12) 1.0166(2) 0.0474(6) Uani 1 1 d . . .
H15 H 0.4738 0.1901 1.0144 0.057 Uiso 1 1 calc R . .


_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
N1 C1 1.412(3) . ?
N1 C2 1.481(2) . ?
N1 H1A 0.8600 . ?
O3 C7 1.354(2) . ?
O3 C16 1.424(2) . ?
O2 C3 1.203(2) . ?
O1 C9 1.370(2) . ?
O1 C1 1.384(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C7 C8 1.367(3) . ?
C7 C6 1.388(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C4 1.387(3) . ?
C4 C5 1.416(3) . ?
C4 C3 1.468(3) . ?
C5 C6 1.365(3) . ?
C5 C17 1.504(3) . ?
C6 H6 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 C2 1.497(3) . ?
C2 C10 1.489(3) . ?
C2 C1 1.491(3) . ?
C1 H1 0.9800 . ?
C10 C15 1.370(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.359(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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
C1 N1 C2 62.01(13) . . ?
C1 N1 H1A 149.0 . . ?
C2 N1 H1A 149.0 . . ?
C7 O3 C16 118.64(16) . . ?
C9 O1 C1 117.59(15) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C7 C8 124.32(18) . . ?
O3 C7 C6 115.44(17) . . ?
C8 C7 C6 120.24(18) . . ?
C7 C8 C9 118.24(17) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
O1 C9 C8 114.42(16) . . ?
O1 C9 C4 122.20(17) . . ?
C8 C9 C4 123.35(18) . . ?
C9 C4 C5 117.30(17) . . ?
C9 C4 C3 120.09(17) . . ?
C5 C4 C3 122.60(17) . . ?
C6 C5 C4 119.07(17) . . ?
C6 C5 C17 118.38(17) . . ?
C4 C5 C17 122.55(17) . . ?
C5 C6 C7 121.78(18) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C3 C4 124.35(18) . . ?
O2 C3 C2 119.40(18) . . ?
C4 C3 C2 116.25(16) . . ?
N1 C2 C10 115.55(16) . . ?
N1 C2 C1 56.72(13) . . ?
C10 C2 C1 120.86(16) . . ?
N1 C2 C3 116.03(16) . . ?
C10 C2 C3 118.24(16) . . ?
C1 C2 C3 114.77(17) . . ?
O1 C1 N1 121.34(17) . . ?
O1 C1 C2 121.82(17) . . ?
N1 C1 C2 61.27(13) . . ?
O1 C1 H1 114.1 . . ?
N1 C1 H1 114.1 . . ?
C2 C1 H1 114.1 . . ?
C15 C10 C11 119.04(19) . . ?
C15 C10 C2 120.86(19) . . ?
C11 C10 C2 120.09(19) . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 120.3(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?

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
C16 O3 C7 C8 -8.6(3) . . . . ?
C16 O3 C7 C6 172.09(18) . . . . ?
O3 C7 C8 C9 -178.15(18) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C1 O1 C9 C8 -157.27(18) . . . . ?
C1 O1 C9 C4 24.5(3) . . . . ?
C7 C8 C9 O1 -178.61(19) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
O1 C9 C4 C5 177.00(18) . . . . ?
C8 C9 C4 C5 -1.1(3) . . . . ?
O1 C9 C4 C3 -2.0(3) . . . . ?
C8 C9 C4 C3 179.91(19) . . . . ?
C9 C4 C5 C6 1.8(3) . . . . ?
C3 C4 C5 C6 -179.19(18) . . . . ?
C9 C4 C5 C17 -178.59(19) . . . . ?
C3 C4 C5 C17 0.4(3) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C17 C5 C6 C7 179.24(19) . . . . ?
O3 C7 C6 C5 178.98(18) . . . . ?
C8 C7 C6 C5 -0.4(3) . . . . ?
C9 C4 C3 O2 161.8(2) . . . . ?
C5 C4 C3 O2 -17.1(3) . . . . ?
C9 C4 C3 C2 -18.6(3) . . . . ?
C5 C4 C3 C2 162.41(18) . . . . ?
C1 N1 C2 C10 -111.49(19) . . . . ?
C1 N1 C2 C3 103.7(2) . . . . ?
O2 C3 C2 N1 132.6(2) . . . . ?
C4 C3 C2 N1 -47.0(3) . . . . ?
O2 C3 C2 C10 -11.2(3) . . . . ?
C4 C3 C2 C10 169.23(18) . . . . ?
O2 C3 C2 C1 -163.94(19) . . . . ?
C4 C3 C2 C1 16.5(3) . . . . ?
C9 O1 C1 N1 47.7(3) . . . . ?
C9 O1 C1 C2 -25.7(3) . . . . ?
C2 N1 C1 O1 -111.7(2) . . . . ?
N1 C2 C1 O1 111.0(2) . . . . ?
C10 C2 C1 O1 -147.0(2) . . . . ?
C3 C2 C1 O1 5.0(3) . . . . ?
C10 C2 C1 N1 102.0(2) . . . . ?
C3 C2 C1 N1 -105.98(19) . . . . ?
N1 C2 C10 C15 -21.8(3) . . . . ?
C1 C2 C10 C15 -86.8(3) . . . . ?
C3 C2 C10 C15 122.1(2) . . . . ?
N1 C2 C10 C11 157.42(18) . . . . ?
C1 C2 C10 C11 92.4(2) . . . . ?
C3 C2 C10 C11 -58.6(3) . . . . ?
C15 C10 C11 C12 -1.2(3) . . . . ?
C2 C10 C11 C12 179.48(19) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C11 C10 C15 C14 1.6(3) . . . . ?
C2 C10 C15 C14 -179.1(2) . . . . ?
C13 C14 C15 C10 -1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.042
