# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1555783'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   22.372(2)
_cell_length_b                   8.6007(9)
_cell_length_c                   20.507(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.939(4)
_cell_angle_gamma                90.00
_cell_volume                     3348.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6184
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      67.53

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8435
_exptl_absorpt_correction_T_max  0.8866
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9432
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.66
_diffrn_reflns_theta_max         65.97
_reflns_number_total             2883
_reflns_number_gt                2448
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0657P)²+0.8022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0184(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2883
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O1 O 0.06068(5) 0.56617(12) 0.23051(5) 0.0771(3) Uani 1 1 d . . .
N1 N 0.09088(6) 0.50425(14) 0.38396(6) 0.0672(4) Uani 1 1 d . . .
H1A H 0.0470 0.5235 0.3520 0.081 Uiso 1 1 calc R . .
N2 N 0.20270(6) 0.56386(14) 0.40829(6) 0.0638(3) Uani 1 1 d . . .
C1 C 0.12824(8) 0.90855(18) 0.34939(9) 0.0766(4) Uani 1 1 d . . .
H1 H 0.1527 0.8614 0.3975 0.092 Uiso 1 1 calc R . .
C2 C 0.12410(10) 1.0692(2) 0.34352(13) 0.0954(6) Uani 1 1 d . . .
H2 H 0.1459 1.1301 0.3877 0.115 Uiso 1 1 calc R . .
C3 C 0.08806(11) 1.1379(2) 0.27298(16) 0.1033(7) Uani 1 1 d . . .
H3 H 0.0852 1.2458 0.2694 0.124 Uiso 1 1 calc R . .
C4 C 0.05621(11) 1.0507(2) 0.20782(14) 0.0971(6) Uani 1 1 d . . .
H4 H 0.0319 1.0991 0.1601 0.117 Uiso 1 1 calc R . .
C5 C 0.05987(8) 0.89107(19) 0.21229(9) 0.0763(4) Uani 1 1 d . . .
H5 H 0.0383 0.8318 0.1676 0.092 Uiso 1 1 calc R . .
C6 C 0.09582(7) 0.81846(17) 0.28350(8) 0.0619(4) Uani 1 1 d . . .
C7 C 0.09489(6) 0.64777(16) 0.28711(7) 0.0593(4) Uani 1 1 d . . .
C8 C 0.13559(7) 0.56845(15) 0.36538(7) 0.0589(4) Uani 1 1 d . . .
C9 C 0.10489(7) 0.41151(15) 0.44709(7) 0.0602(4) Uani 1 1 d . . .
C10 C 0.17160(8) 0.35826(17) 0.50233(8) 0.0685(4) Uani 1 1 d . . .
H10 H 0.2105 0.3853 0.4997 0.082 Uiso 1 1 calc R . .
C11 C 0.17941(9) 0.2652(2) 0.56086(9) 0.0840(5) Uani 1 1 d . . .
H11 H 0.2241 0.2299 0.5980 0.101 Uiso 1 1 calc R . .
C12 C 0.12295(11) 0.2235(3) 0.56557(11) 0.1034(6) Uani 1 1 d . . .
H12 H 0.1289 0.1592 0.6051 0.124 Uiso 1 1 calc R . .
C13 C 0.05689(10) 0.2777(3) 0.51111(11) 0.1021(6) Uani 1 1 d . . .
H13 H 0.0183 0.2512 0.5144 0.123 Uiso 1 1 calc R . .
C14 C 0.04779(8) 0.37067(19) 0.45202(9) 0.0776(4) Uani 1 1 d . . .
H14 H 0.0030 0.4061 0.4153 0.093 Uiso 1 1 calc R . .
C15 C 0.24370(7) 0.62725(16) 0.38062(7) 0.0592(4) Uani 1 1 d . . .
C16 C 0.23865(8) 0.57429(19) 0.31414(8) 0.0720(4) Uani 1 1 d . . .
H16 H 0.2061 0.4975 0.2848 0.086 Uiso 1 1 calc R . .
C17 C 0.28174(9) 0.6351(2) 0.29116(9) 0.0829(5) Uani 1 1 d . . .
H17 H 0.2781 0.5987 0.2465 0.099 Uiso 1 1 calc R . .
C18 C 0.32974(9) 0.7484(2) 0.33349(10) 0.0824(5) Uani 1 1 d . . .
H18 H 0.3584 0.7895 0.3175 0.099 Uiso 1 1 calc R . .
C19 C 0.33537(9) 0.8008(2) 0.39944(10) 0.0826(5) Uani 1 1 d . . .
H19 H 0.3677 0.8784 0.4282 0.099 Uiso 1 1 calc R . .
C20 C 0.29344(8) 0.73957(18) 0.42360(8) 0.0715(4) Uani 1 1 d . . .
H20 H 0.2986 0.7741 0.4693 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
O1 C7 1.2189(15) . ?
N1 C8 1.3615(17) . ?
N1 C9 1.4075(17) . ?
N1 H1A 0.8600 . ?
N2 C8 1.2776(17) . ?
N2 C15 1.4181(18) . ?
C1 C6 1.384(2) . ?
C1 C2 1.386(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.471(2) . ?
C7 C8 1.5246(17) . ?
C9 C14 1.379(2) . ?
C9 C10 1.3899(19) . ?
C10 C11 1.375(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.382(2) . ?
C15 C16 1.3842(19) . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(2) . ?
C19 H19 0.9300 . ?
C20 H20 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
C8 N1 C9 130.40(11) . . ?
C8 N1 H1A 114.8 . . ?
C9 N1 H1A 114.8 . . ?
C8 N2 C15 119.05(11) . . ?
C6 C1 C2 119.81(16) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 119.95(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.79(17) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.24(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.01(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.21(14) . . ?
C1 C6 C7 121.59(12) . . ?
C5 C6 C7 119.10(13) . . ?
O1 C7 C6 123.05(12) . . ?
O1 C7 C8 117.99(12) . . ?
C6 C7 C8 118.89(11) . . ?
N2 C8 N1 124.36(12) . . ?
N2 C8 C7 124.66(12) . . ?
N1 C8 C7 110.98(11) . . ?
C14 C9 C10 119.55(13) . . ?
C14 C9 N1 116.59(12) . . ?
C10 C9 N1 123.85(13) . . ?
C11 C10 C9 119.29(15) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 121.32(16) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.30(16) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.41(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.13(15) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C20 C15 C16 118.47(14) . . ?
C20 C15 N2 119.11(12) . . ?
C16 C15 N2 122.31(13) . . ?
C17 C16 C15 120.24(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.60(15) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.58(16) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.41(16) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.67(13) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?

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
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C6 C7 -175.89(14) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 175.75(14) . . . . ?
C1 C6 C7 O1 172.10(13) . . . . ?
C5 C6 C7 O1 -4.2(2) . . . . ?
C1 C6 C7 C8 -4.85(19) . . . . ?
C5 C6 C7 C8 178.86(12) . . . . ?
C15 N2 C8 N1 176.37(12) . . . . ?
C15 N2 C8 C7 -4.31(19) . . . . ?
C9 N1 C8 N2 -5.7(2) . . . . ?
C9 N1 C8 C7 174.86(13) . . . . ?
O1 C7 C8 N2 113.37(15) . . . . ?
C6 C7 C8 N2 -69.52(17) . . . . ?
O1 C7 C8 N1 -67.23(15) . . . . ?
C6 C7 C8 N1 109.88(13) . . . . ?
C8 N1 C9 C14 176.58(14) . . . . ?
C8 N1 C9 C10 -4.7(2) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
N1 C9 C10 C11 -178.48(14) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C10 C9 C14 C13 -0.1(2) . . . . ?
N1 C9 C14 C13 178.69(16) . . . . ?
C8 N2 C15 C20 124.96(14) . . . . ?
C8 N2 C15 C16 -58.90(18) . . . . ?
C20 C15 C16 C17 -1.1(2) . . . . ?
N2 C15 C16 C17 -177.28(13) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -1.8(3) . . . . ?
C16 C15 C20 C19 2.1(2) . . . . ?
N2 C15 C20 C19 178.36(14) . . . . ?

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
N1 H1A O1 0.86 2.12 2.9783(15) 177.6 2

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        65.97
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.056
