# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_0
_database_code_depnum_ccdc_archive 'CCDC 1572612'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H22 N2 O'
_chemical_formula_weight         426.50

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6135(5)
_cell_length_b                   10.5171(5)
_cell_length_c                   12.3679(5)
_cell_angle_alpha                72.018(3)
_cell_angle_beta                 70.400(4)
_cell_angle_gamma                89.928(4)
_cell_volume                     1113.15(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1954
_cell_measurement_theta_min      2.3655
_cell_measurement_theta_max      22.383

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9950
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         26.80
_reflns_number_total             4745
_reflns_number_gt                2875
_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)+(0.0749P)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_number_reflns         4745
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_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 0.22832(16) 0.06612(14) 0.86533(12) 0.0462(4) Uani 1 1 d . . .
O1 O 0.31297(16) 0.02036(13) 0.58422(12) 0.0653(4) Uani 1 1 d . . .
N2 N 0.30644(16) 0.00956(13) 0.77646(12) 0.0459(4) Uani 1 1 d . . .
C4 C 0.13794(18) 0.14156(15) 0.82625(14) 0.0421(4) Uani 1 1 d . . .
C5 C 0.07536(18) 0.27866(16) 0.53508(14) 0.0423(4) Uani 1 1 d . . .
C6 C 0.04335(18) 0.21579(16) 0.90081(15) 0.0426(4) Uani 1 1 d . . .
C7 C 0.17561(19) 0.27877(16) 0.60190(14) 0.0435(4) Uani 1 1 d . . .
C8 C 0.4224(2) -0.06817(16) 0.79428(16) 0.0484(4) Uani 1 1 d . . .
C9 C 0.0700(2) 0.37593(18) 0.43059(16) 0.0514(5) Uani 1 1 d . . .
H9A H 0.1338 0.4556 0.3953 0.062 Uiso 1 1 calc R . .
C10 C -0.02265(19) 0.16080(16) 0.58839(15) 0.0464(4) Uani 1 1 d . . .
C11 C -0.0553(2) 0.29812(19) 0.86313(17) 0.0576(5) Uani 1 1 d . . .
H11A H -0.0647 0.3065 0.7889 0.069 Uiso 1 1 calc R . .
C12 C 0.2776(2) 0.37862(17) 0.57913(15) 0.0499(4) Uani 1 1 d . . .
H12A H 0.2839 0.4566 0.5155 0.060 Uiso 1 1 calc R . .
C13 C 0.14236(19) 0.14151(16) 0.70321(14) 0.0433(4) Uani 1 1 d . . .
C14 C 0.2646(2) 0.05157(16) 0.67568(15) 0.0477(4) Uani 1 1 d . . .
C15 C -0.1260(2) 0.2329(2) 0.43212(18) 0.0623(5) Uani 1 1 d . . .
H15A H -0.1922 0.2177 0.3960 0.075 Uiso 1 1 calc R . .
C16 C -0.0034(2) 0.07404(17) 0.70296(16) 0.0505(5) Uani 1 1 d . . .
H16A H 0.0075 -0.0175 0.7024 0.061 Uiso 1 1 calc R . .
H16B H -0.0879 0.0728 0.7737 0.061 Uiso 1 1 calc R . .
C17 C 0.0548(2) 0.20612(19) 1.01241(16) 0.0562(5) Uani 1 1 d . . .
H17A H 0.1208 0.1516 1.0394 0.067 Uiso 1 1 calc R . .
C18 C -0.0313(2) 0.35213(19) 0.38048(17) 0.0585(5) Uani 1 1 d . . .
H18A H -0.0364 0.4167 0.3113 0.070 Uiso 1 1 calc R . .
C19 C -0.1232(2) 0.13689(19) 0.53614(18) 0.0573(5) Uani 1 1 d . . .
H19A H -0.1874 0.0575 0.5708 0.069 Uiso 1 1 calc R . .
C20 C 0.3815(2) 0.37886(17) 0.64376(15) 0.0509(5) Uani 1 1 d . . .
C21 C 0.4549(2) -0.0893(2) 0.89853(18) 0.0647(6) Uani 1 1 d . . .
H21A H 0.3996 -0.0535 0.9575 0.078 Uiso 1 1 calc R . .
C22 C -0.0298(2) 0.2759(2) 1.08274(18) 0.0693(6) Uani 1 1 d . . .
H22A H -0.0206 0.2685 1.1569 0.083 Uiso 1 1 calc R . .
C23 C 0.4926(2) 0.2946(2) 0.63920(18) 0.0626(5) Uani 1 1 d . . .
H23A H 0.5051 0.2392 0.5916 0.075 Uiso 1 1 calc R . .
C24 C 0.5061(2) -0.1213(2) 0.70729(18) 0.0648(6) Uani 1 1 d . . .
H24A H 0.4858 -0.1077 0.6363 0.078 Uiso 1 1 calc R . .
C25 C -0.1403(2) 0.3682(2) 0.9350(2) 0.0680(6) Uani 1 1 d . . .
H25A H -0.2060 0.4234 0.9084 0.082 Uiso 1 1 calc R . .
C26 C -0.1287(2) 0.3572(2) 1.0445(2) 0.0694(6) Uani 1 1 d . . .
H26A H -0.1866 0.4039 1.0927 0.083 Uiso 1 1 calc R . .
C27 C 0.6520(3) -0.2162(2) 0.8295(2) 0.0743(6) Uani 1 1 d . . .
H27A H 0.7289 -0.2659 0.8412 0.089 Uiso 1 1 calc R . .
C28 C 0.6202(3) -0.1950(2) 0.7262(2) 0.0781(7) Uani 1 1 d . . .
H28A H 0.6762 -0.2307 0.6674 0.094 Uiso 1 1 calc R . .
C29 C 0.3718(2) 0.4659(2) 0.7092(2) 0.0711(6) Uani 1 1 d . . .
H29A H 0.3021 0.5273 0.7094 0.085 Uiso 1 1 calc R . .
C30 C 0.5688(3) -0.1632(2) 0.9157(2) 0.0788(7) Uani 1 1 d . . .
H30A H 0.5895 -0.1773 0.9865 0.095 Uiso 1 1 calc R . .
C31 C 0.5695(3) 0.3752(3) 0.7717(2) 0.0885(8) Uani 1 1 d . . .
H31A H 0.6310 0.3725 0.8164 0.106 Uiso 1 1 calc R . .
C32 C 0.5853(2) 0.2917(2) 0.7043(2) 0.0783(7) Uani 1 1 d . . .
H32A H 0.6579 0.2330 0.7022 0.094 Uiso 1 1 calc R . .
C33 C 0.4645(3) 0.4628(3) 0.7743(2) 0.0930(8) Uani 1 1 d . . .
H33A H 0.4553 0.5202 0.8198 0.112 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 C4 1.289(2) . ?
N1 N2 1.4053(18) . ?
O1 C14 1.2163(19) . ?
N2 C14 1.381(2) . ?
N2 C8 1.418(2) . ?
C4 C6 1.472(2) . ?
C4 C13 1.508(2) . ?
C5 C10 1.393(2) . ?
C5 C9 1.396(2) . ?
C5 C7 1.465(2) . ?
C6 C11 1.383(2) . ?
C6 C17 1.394(2) . ?
C7 C12 1.334(2) . ?
C7 C13 1.540(2) . ?
C8 C24 1.381(2) . ?
C8 C21 1.379(3) . ?
C9 C18 1.377(2) . ?
C10 C19 1.391(2) . ?
C10 C16 1.501(2) . ?
C11 C25 1.385(2) . ?
C12 C20 1.474(2) . ?
C13 C14 1.523(2) . ?
C13 C16 1.573(2) . ?
C15 C19 1.377(2) . ?
C15 C18 1.388(3) . ?
C17 C22 1.369(3) . ?
C20 C29 1.381(3) . ?
C20 C23 1.385(3) . ?
C21 C30 1.379(3) . ?
C22 C26 1.382(3) . ?
C23 C32 1.382(3) . ?
C24 C28 1.385(3) . ?
C25 C26 1.365(3) . ?
C27 C28 1.364(3) . ?
C27 C30 1.371(3) . ?
C29 C33 1.382(3) . ?
C31 C32 1.362(3) . ?
C31 C33 1.365(3) . ?

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
C4 N1 N2 108.47(13) . . ?
C14 N2 N1 111.76(13) . . ?
C14 N2 C8 129.08(15) . . ?
N1 N2 C8 118.83(14) . . ?
N1 C4 C6 120.05(15) . . ?
N1 C4 C13 113.08(14) . . ?
C6 C4 C13 126.87(15) . . ?
C10 C5 C9 120.02(16) . . ?
C10 C5 C7 110.96(15) . . ?
C9 C5 C7 129.01(16) . . ?
C11 C6 C17 118.13(16) . . ?
C11 C6 C4 122.37(16) . . ?
C17 C6 C4 119.49(16) . . ?
C12 C7 C5 126.55(16) . . ?
C12 C7 C13 126.11(16) . . ?
C5 C7 C13 107.34(14) . . ?
C24 C8 C21 119.12(18) . . ?
C24 C8 N2 120.88(17) . . ?
C21 C8 N2 119.99(17) . . ?
C18 C9 C5 118.98(17) . . ?
C5 C10 C19 120.55(17) . . ?
C5 C10 C16 111.23(15) . . ?
C19 C10 C16 128.21(16) . . ?
C25 C11 C6 120.56(18) . . ?
C7 C12 C20 127.09(16) . . ?
C4 C13 C14 100.24(13) . . ?
C4 C13 C7 117.16(13) . . ?
C14 C13 C7 111.98(13) . . ?
C4 C13 C16 114.78(13) . . ?
C14 C13 C16 107.99(13) . . ?
C7 C13 C16 104.57(13) . . ?
O1 C14 N2 126.91(16) . . ?
O1 C14 C13 126.69(16) . . ?
N2 C14 C13 106.38(14) . . ?
C19 C15 C18 120.86(18) . . ?
C10 C16 C13 104.48(13) . . ?
C22 C17 C6 120.80(18) . . ?
C9 C18 C15 120.75(18) . . ?
C15 C19 C10 118.82(18) . . ?
C29 C20 C23 118.08(18) . . ?
C29 C20 C12 120.37(17) . . ?
C23 C20 C12 121.53(17) . . ?
C30 C21 C8 120.3(2) . . ?
C17 C22 C26 120.55(19) . . ?
C32 C23 C20 121.0(2) . . ?
C8 C24 C28 119.7(2) . . ?
C26 C25 C11 120.73(19) . . ?
C25 C26 C22 119.23(18) . . ?
C28 C27 C30 119.0(2) . . ?
C27 C28 C24 121.2(2) . . ?
C20 C29 C33 120.7(2) . . ?
C27 C30 C21 120.7(2) . . ?
C32 C31 C33 120.7(2) . . ?
C31 C32 C23 119.5(2) . . ?
C31 C33 C29 119.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.80
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
