# 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_100823g
_database_code_depnum_ccdc_archive 'CCDC 1487667'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 N O2'
_chemical_formula_weight         299.31

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   P2(1)

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

_cell_length_a                   7.7305(8)
_cell_length_b                   7.8246(8)
_cell_length_c                   12.9282(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.6780(10)
_cell_angle_gamma                90.00
_cell_volume                     762.94(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    778
_cell_measurement_theta_min      2.701
_cell_measurement_theta_max      21.323

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9645
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            3983
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1446
_reflns_number_gt                903
_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)+(0.0235P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_number_reflns         1446
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.0620(4) 0.2614(5) 0.5687(3) 0.0656(12) Uani 1 1 d . . .
O1 O 0.0688(3) 0.4697(3) 0.22498(19) 0.0485(8) Uani 1 1 d . . .
O2 O -0.1217(3) 0.3356(4) 0.30207(19) 0.0624(9) Uani 1 1 d . . .
C1 C 0.0240(5) 0.3997(6) 0.3141(3) 0.0456(11) Uani 1 1 d . . .
C2 C 0.1560(5) 0.4103(5) 0.4123(3) 0.0368(10) Uani 1 1 d . . .
C3 C 0.3213(4) 0.4828(5) 0.4195(3) 0.0332(10) Uani 1 1 d . . .
C4 C 0.3605(4) 0.5387(5) 0.3234(3) 0.0333(10) Uani 1 1 d . . .
C5 C 0.5243(4) 0.6205(5) 0.2981(3) 0.0439(11) Uani 1 1 d . . .
H5A H 0.5577 0.7232 0.3398 0.053 Uiso 1 1 calc R . .
H5B H 0.6236 0.5417 0.3108 0.053 Uiso 1 1 calc R . .
C6 C 0.4643(5) 0.6617(5) 0.1816(3) 0.0437(11) Uani 1 1 d . . .
C7 C 0.5512(5) 0.7401(6) 0.1140(3) 0.0556(13) Uani 1 1 d . . .
H7 H 0.6681 0.7753 0.1377 0.067 Uiso 1 1 calc R . .
C8 C 0.4640(7) 0.7671(7) 0.0092(4) 0.0692(15) Uani 1 1 d . . .
H8 H 0.5223 0.8229 -0.0368 0.083 Uiso 1 1 calc R . .
C9 C 0.2922(6) 0.7119(6) -0.0272(3) 0.0674(15) Uani 1 1 d . . .
H9 H 0.2364 0.7295 -0.0978 0.081 Uiso 1 1 calc R . .
C10 C 0.2029(5) 0.6317(6) 0.0389(3) 0.0596(13) Uani 1 1 d . . .
H10 H 0.0868 0.5945 0.0145 0.072 Uiso 1 1 calc R . .
C11 C 0.2906(5) 0.6072(5) 0.1439(3) 0.0418(10) Uani 1 1 d . . .
C12 C 0.2340(5) 0.5341(5) 0.2326(3) 0.0371(10) Uani 1 1 d . . .
C13 C 0.1045(5) 0.3295(6) 0.5007(3) 0.0463(11) Uani 1 1 d . . .
C14 C 0.4446(5) 0.5083(5) 0.5232(3) 0.0351(10) Uani 1 1 d . . .
C15 C 0.3838(5) 0.5782(5) 0.6074(3) 0.0416(10) Uani 1 1 d . . .
H15 H 0.2655 0.6102 0.5978 0.050 Uiso 1 1 calc R . .
C16 C 0.4970(5) 0.6009(5) 0.7052(3) 0.0449(11) Uani 1 1 d . . .
H16 H 0.4540 0.6490 0.7604 0.054 Uiso 1 1 calc R . .
C17 C 0.6725(5) 0.5533(5) 0.7222(3) 0.0457(11) Uani 1 1 d . . .
C18 C 0.7341(5) 0.4888(5) 0.6389(3) 0.0450(11) Uani 1 1 d . . .
H18 H 0.8531 0.4591 0.6489 0.054 Uiso 1 1 calc R . .
C19 C 0.6238(4) 0.4667(5) 0.5399(3) 0.0409(10) Uani 1 1 d . . .
H19 H 0.6695 0.4239 0.4843 0.049 Uiso 1 1 calc R . .
C20 C 0.7923(5) 0.5729(6) 0.8309(3) 0.0639(14) Uani 1 1 d . . .
H20A H 0.7881 0.6889 0.8544 0.096 Uiso 1 1 calc R . .
H20B H 0.9118 0.5446 0.8275 0.096 Uiso 1 1 calc R . .
H20C H 0.7533 0.4977 0.8799 0.096 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 C13 1.136(4) . ?
O1 C12 1.356(4) . ?
O1 C1 1.387(4) . ?
O2 C1 1.211(4) . ?
C1 C2 1.446(4) . ?
C2 C3 1.383(4) . ?
C2 C13 1.437(5) . ?
C3 C4 1.411(4) . ?
C3 C14 1.478(5) . ?
C4 C12 1.353(4) . ?
C4 C5 1.517(4) . ?
C5 C6 1.511(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.360(4) . ?
C6 C11 1.391(4) . ?
C7 C8 1.391(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.433(5) . ?
C14 C15 1.390(4) . ?
C14 C19 1.392(4) . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(5) . ?
C17 C20 1.512(5) . ?
C18 C19 1.384(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C12 O1 C1 119.3(3) . . ?
O2 C1 O1 116.8(4) . . ?
O2 C1 C2 126.4(4) . . ?
O1 C1 C2 116.7(3) . . ?
C3 C2 C13 122.7(3) . . ?
C3 C2 C1 123.1(3) . . ?
C13 C2 C1 114.1(3) . . ?
C2 C3 C4 116.2(3) . . ?
C2 C3 C14 121.3(3) . . ?
C4 C3 C14 122.5(3) . . ?
C12 C4 C3 120.1(3) . . ?
C12 C4 C5 107.6(3) . . ?
C3 C4 C5 132.1(3) . . ?
C6 C5 C4 102.5(3) . . ?
C6 C5 H5A 111.3 . . ?
C4 C5 H5A 111.3 . . ?
C6 C5 H5B 111.3 . . ?
C4 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
C7 C6 C11 119.2(4) . . ?
C7 C6 C5 130.6(4) . . ?
C11 C6 C5 110.2(3) . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 118.0(4) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C10 C11 C6 121.7(4) . . ?
C10 C11 C12 131.8(4) . . ?
C6 C11 C12 106.4(3) . . ?
C4 C12 O1 124.2(3) . . ?
C4 C12 C11 113.2(3) . . ?
O1 C12 C11 122.5(3) . . ?
N1 C13 C2 177.9(5) . . ?
C15 C14 C19 117.8(4) . . ?
C15 C14 C3 120.1(3) . . ?
C19 C14 C3 122.0(3) . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 121.0(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 118.4(4) . . ?
C18 C17 C20 121.4(4) . . ?
C16 C17 C20 120.2(4) . . ?
C17 C18 C19 121.6(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C12 O1 C1 O2 -176.1(3) . . . . ?
C12 O1 C1 C2 3.8(5) . . . . ?
O2 C1 C2 C3 178.7(4) . . . . ?
O1 C1 C2 C3 -1.2(5) . . . . ?
O2 C1 C2 C13 2.3(6) . . . . ?
O1 C1 C2 C13 -177.6(3) . . . . ?
C13 C2 C3 C4 172.5(3) . . . . ?
C1 C2 C3 C4 -3.6(5) . . . . ?
C13 C2 C3 C14 -10.8(6) . . . . ?
C1 C2 C3 C14 173.1(3) . . . . ?
C2 C3 C4 C12 5.9(5) . . . . ?
C14 C3 C4 C12 -170.8(3) . . . . ?
C2 C3 C4 C5 -178.9(4) . . . . ?
C14 C3 C4 C5 4.4(6) . . . . ?
C12 C4 C5 C6 1.2(4) . . . . ?
C3 C4 C5 C6 -174.4(4) . . . . ?
C4 C5 C6 C7 178.3(4) . . . . ?
C4 C5 C6 C11 -1.3(4) . . . . ?
C11 C6 C7 C8 1.2(6) . . . . ?
C5 C6 C7 C8 -178.4(4) . . . . ?
C6 C7 C8 C9 -1.4(6) . . . . ?
C7 C8 C9 C10 0.9(7) . . . . ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C9 C10 C11 C6 -0.1(6) . . . . ?
C9 C10 C11 C12 177.7(4) . . . . ?
C7 C6 C11 C10 -0.4(6) . . . . ?
C5 C6 C11 C10 179.3(4) . . . . ?
C7 C6 C11 C12 -178.7(4) . . . . ?
C5 C6 C11 C12 1.0(4) . . . . ?
C3 C4 C12 O1 -3.6(6) . . . . ?
C5 C4 C12 O1 -179.8(3) . . . . ?
C3 C4 C12 C11 175.5(3) . . . . ?
C5 C4 C12 C11 -0.7(4) . . . . ?
C1 O1 C12 C4 -1.6(5) . . . . ?
C1 O1 C12 C11 179.5(3) . . . . ?
C10 C11 C12 C4 -178.2(4) . . . . ?
C6 C11 C12 C4 -0.1(4) . . . . ?
C10 C11 C12 O1 0.9(7) . . . . ?
C6 C11 C12 O1 179.0(3) . . . . ?
C3 C2 C13 N1 -132(11) . . . . ?
C1 C2 C13 N1 44(11) . . . . ?
C2 C3 C14 C15 -46.1(5) . . . . ?
C4 C3 C14 C15 130.4(3) . . . . ?
C2 C3 C14 C19 135.0(4) . . . . ?
C4 C3 C14 C19 -48.5(5) . . . . ?
C19 C14 C15 C16 -1.8(5) . . . . ?
C3 C14 C15 C16 179.2(3) . . . . ?
C14 C15 C16 C17 -0.7(6) . . . . ?
C15 C16 C17 C18 2.4(6) . . . . ?
C15 C16 C17 C20 -177.7(4) . . . . ?
C16 C17 C18 C19 -1.7(6) . . . . ?
C20 C17 C18 C19 178.4(4) . . . . ?
C17 C18 C19 C14 -0.8(6) . . . . ?
C15 C14 C19 C18 2.6(6) . . . . ?
C3 C14 C19 C18 -178.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
