# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ap-14
_database_code_depnum_ccdc_archive 'CCDC 1059288'
_audit_update_record             
;
2015-04-13 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H16 N2 O3'
_chemical_formula_sum            'C21 H16 N2 O3'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         344.36

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/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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

_cell_length_a                   16.7245(10)
_cell_length_b                   11.3341(6)
_cell_length_c                   9.6962(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.028(5)
_cell_angle_gamma                90.00
_cell_volume                     1775.12(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1976
_cell_measurement_theta_min      3.3065
_cell_measurement_theta_max      29.0916
_exptl_crystal_size_max          0.028
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.016
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720.0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93478
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8177
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         29.16
_reflns_number_total             4800
_reflns_number_gt                2681
_reflns_threshold_expression     ?

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_structure_solution    ?
_computing_structure_refinement  ?

_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0511P)²+0.2618P] 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         4034
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
O3 O 0.40555(9) 0.44837(13) 0.33511(11) 0.0570(4) Uani 1 1 d . . .
H001 H 0.3656 0.4105 0.2898 0.086 Uiso 1 1 calc R . .
O2 O 0.22004(8) 0.24473(12) 0.26162(11) 0.0579(4) Uani 1 1 d . . .
O1 O 0.13472(8) -0.03837(14) 0.26974(13) 0.0648(4) Uani 1 1 d . . .
N1 N 0.23297(9) 0.30338(13) 0.04737(13) 0.0434(4) Uani 1 1 d . . .
H004 H 0.2148 0.3001 -0.0440 0.052 Uiso 1 1 calc R . .
N2 N 0.29448(9) 0.38132(13) 0.11137(13) 0.0418(3) Uani 1 1 d . . .
C16 C 0.39545(10) 0.52292(15) 0.09806(16) 0.0403(4) Uani 1 1 d . . .
C15 C 0.32644(10) 0.44718(16) 0.03301(16) 0.0420(4) Uani 1 1 d . . .
H007 H 0.3054 0.4464 -0.0657 0.050 Uiso 1 1 calc R . .
C14 C 0.20217(10) 0.23281(15) 0.13168(15) 0.0397(4) Uani 1 1 d . . .
C13 C 0.14689(10) 0.13287(16) 0.05629(16) 0.0419(4) Uani 1 1 d . . .
H009 H 0.1292 0.1490 -0.0464 0.050 Uiso 1 1 calc R . .
C17 C 0.43368(11) 0.51868(16) 0.24489(17) 0.0443(4) Uani 1 1 d . . .
C1 C 0.19778(10) 0.02077(16) 0.08228(17) 0.0428(4) Uani 1 1 d . . .
C6 C 0.19006(11) -0.05721(17) 0.18795(18) 0.0470(4) Uani 1 1 d . . .
C12 C 0.07205(11) 0.12101(16) 0.11422(17) 0.0432(4) Uani 1 1 d . . .
C11 C 0.00338(12) 0.1933(2) 0.0683(2) 0.0612(5) Uani 1 1 d . . .
H014 H 0.0022 0.2480 -0.0036 0.073 Uiso 1 1 calc R . .
C18 C 0.50281(13) 0.58652(19) 0.3021(2) 0.0628(5) Uani 1 1 d . . .
H015 H 0.5293 0.5810 0.3989 0.075 Uiso 1 1 calc R . .
C9 C -0.06242(13) 0.1050(2) 0.2326(3) 0.0715(7) Uani 1 1 d . . .
H016 H -0.1070 0.1005 0.2732 0.086 Uiso 1 1 calc R . .
C2 C 0.25507(12) -0.00590(19) 0.0063(2) 0.0576(5) Uani 1 1 d . . .
H017 H 0.2610 0.0447 -0.0659 0.069 Uiso 1 1 calc R . .
C8 C 0.00384(13) 0.0312(2) 0.2781(2) 0.0640(6) Uani 1 1 d . . .
H018 H 0.0041 -0.0244 0.3487 0.077 Uiso 1 1 calc R . .
C7 C 0.07066(11) 0.03946(18) 0.21853(18) 0.0485(4) Uani 1 1 d . . .
C21 C 0.42783(12) 0.59978(18) 0.0136(2) 0.0546(5) Uani 1 1 d . . .
H020 H 0.4035 0.6038 -0.0840 0.066 Uiso 1 1 calc R . .
C5 C 0.23750(13) -0.1578(2) 0.2174(2) 0.0618(5) Uani 1 1 d . . .
H021 H 0.2312 -0.2093 0.2885 0.074 Uiso 1 1 calc R . .
C10 C -0.06302(13) 0.1855(2) 0.1271(3) 0.0737(7) Uani 1 1 d . . .
H022 H -0.1084 0.2350 0.0951 0.088 Uiso 1 1 calc R . .
C3 C 0.30321(14) -0.1053(2) 0.0352(2) 0.0698(6) Uani 1 1 d . . .
H023 H 0.3417 -0.1212 -0.0165 0.084 Uiso 1 1 calc R . .
C20 C 0.49540(14) 0.6698(2) 0.0732(2) 0.0676(6) Uani 1 1 d . . .
H024 H 0.5157 0.7219 0.0164 0.081 Uiso 1 1 calc R . .
C4 C 0.29447(13) -0.1817(2) 0.1408(3) 0.0692(6) Uani 1 1 d . . .
H025 H 0.3270 -0.2492 0.1604 0.083 Uiso 1 1 calc R . .
C19 C 0.53253(14) 0.6620(2) 0.2168(2) 0.0718(6) Uani 1 1 d . . .
H026 H 0.5785 0.7085 0.2568 0.086 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
O3 C17 1.355(2) . ?
O3 H001 0.8200 . ?
O2 C14 1.2246(17) . ?
O1 C7 1.377(2) . ?
O1 C6 1.383(2) . ?
N1 C14 1.339(2) . ?
N1 N2 1.3758(18) . ?
N1 H004 0.8600 . ?
N2 C15 1.277(2) . ?
C16 C21 1.397(2) . ?
C16 C17 1.402(2) . ?
C16 C15 1.445(2) . ?
C15 H007 0.9300 . ?
C14 C13 1.524(2) . ?
C13 C12 1.505(2) . ?
C13 C1 1.514(2) . ?
C13 H009 0.9800 . ?
C17 C18 1.380(3) . ?
C1 C6 1.384(2) . ?
C1 C2 1.385(2) . ?
C6 C5 1.376(3) . ?
C12 C7 1.375(2) . ?
C12 C11 1.387(3) . ?
C11 C10 1.376(3) . ?
C11 H014 0.9300 . ?
C18 C19 1.369(3) . ?
C18 H015 0.9300 . ?
C9 C8 1.367(3) . ?
C9 C10 1.369(3) . ?
C9 H016 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H017 0.9300 . ?
C8 C7 1.388(2) . ?
C8 H018 0.9300 . ?
C21 C20 1.379(3) . ?
C21 H020 0.9300 . ?
C5 C4 1.379(3) . ?
C5 H021 0.9300 . ?
C10 H022 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H023 0.9300 . ?
C20 C19 1.373(3) . ?
C20 H024 0.9300 . ?
C4 H025 0.9300 . ?
C19 H026 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
C17 O3 H001 109.5 . . ?
C7 O1 C6 117.77(13) . . ?
C14 N1 N2 118.00(12) . . ?
C14 N1 H004 121.0 . . ?
N2 N1 H004 121.0 . . ?
C15 N2 N1 119.10(13) . . ?
C21 C16 C17 118.19(16) . . ?
C21 C16 C15 120.10(15) . . ?
C17 C16 C15 121.67(14) . . ?
N2 C15 C16 119.83(14) . . ?
N2 C15 H007 120.1 . . ?
C16 C15 H007 120.1 . . ?
O2 C14 N1 122.17(15) . . ?
O2 C14 C13 122.10(14) . . ?
N1 C14 C13 115.66(13) . . ?
C12 C13 C1 110.43(14) . . ?
C12 C13 C14 110.32(13) . . ?
C1 C13 C14 107.40(14) . . ?
C12 C13 H009 109.6 . . ?
C1 C13 H009 109.6 . . ?
C14 C13 H009 109.6 . . ?
O3 C17 C18 117.60(15) . . ?
O3 C17 C16 122.19(15) . . ?
C18 C17 C16 120.21(16) . . ?
C6 C1 C2 117.68(18) . . ?
C6 C1 C13 120.19(15) . . ?
C2 C1 C13 122.09(17) . . ?
C5 C6 O1 116.38(17) . . ?
C5 C6 C1 121.57(17) . . ?
O1 C6 C1 122.05(17) . . ?
C7 C12 C11 117.56(17) . . ?
C7 C12 C13 120.59(16) . . ?
C11 C12 C13 121.82(16) . . ?
C10 C11 C12 121.3(2) . . ?
C10 C11 H014 119.4 . . ?
C12 C11 H014 119.4 . . ?
C19 C18 C17 120.18(19) . . ?
C19 C18 H015 119.9 . . ?
C17 C18 H015 119.9 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H016 120.1 . . ?
C10 C9 H016 120.1 . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H017 119.3 . . ?
C1 C2 H017 119.3 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H018 120.1 . . ?
C7 C8 H018 120.1 . . ?
C12 C7 O1 122.41(15) . . ?
C12 C7 C8 121.37(19) . . ?
O1 C7 C8 116.22(17) . . ?
C20 C21 C16 120.89(18) . . ?
C20 C21 H020 119.6 . . ?
C16 C21 H020 119.6 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H021 120.3 . . ?
C4 C5 H021 120.3 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H022 119.9 . . ?
C11 C10 H022 119.9 . . ?
C2 C3 C4 119.90(19) . . ?
C2 C3 H023 120.1 . . ?
C4 C3 H023 120.1 . . ?
C19 C20 C21 119.59(19) . . ?
C19 C20 H024 120.2 . . ?
C21 C20 H024 120.2 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H025 120.0 . . ?
C5 C4 H025 120.0 . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H026 119.6 . . ?
C20 C19 H026 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.841
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047

