# 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_exp_885
_database_code_depnum_ccdc_archive 'CCDC 1582339'
_audit_update_record             
;
2017-10-26 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H16 N2 O'
_chemical_formula_weight         372.41

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.9209(3)
_cell_length_b                   9.1610(3)
_cell_length_c                   12.7949(4)
_cell_angle_alpha                101.938(2)
_cell_angle_beta                 106.434(3)
_cell_angle_gamma                107.197(3)
_cell_volume                     908.67(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30054
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         66.78
_reflns_number_total             3191
_reflns_number_gt                2767
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0745P)²+0.1892P] 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         3191
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1563
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.214
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

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
N0AA N 0.2908(2) 0.3627(2) 0.76022(15) 0.0590(4) Uani 1 1 d . . .
N1AA N 0.14220(18) 0.63814(18) 0.70412(13) 0.0491(4) Uani 1 1 d . . .
C2AA C 0.4954(2) 0.6295(2) 0.88302(16) 0.0502(5) Uani 1 1 d . . .
C3AA C 0.6261(2) 0.5706(2) 0.91093(15) 0.0474(4) Uani 1 1 d . . .
C4AA C 0.5863(2) 0.4018(2) 0.85756(15) 0.0493(4) Uani 1 1 d . . .
O0AA O 0.1030(2) 0.5524(3) 0.85129(16) 0.0914(6) Uani 1 1 d . . .
C5AA C 0.4192(2) 0.3036(2) 0.78350(17) 0.0533(5) Uani 1 1 d . . .
C6AA C 0.0152(2) 0.7059(2) 0.68925(17) 0.0500(4) Uani 1 1 d . . .
C7AA C 0.3294(2) 0.5153(2) 0.80698(16) 0.0530(5) Uani 1 1 d . . .
C8AA C 0.7065(3) 0.3291(2) 0.87486(17) 0.0573(5) Uani 1 1 d . . .
H8AA H 0.8178 0.3917 0.9230 0.069 Uiso 1 1 calc R . .
C9AA C 0.1198(2) 0.7209(2) 0.54518(16) 0.0496(4) Uani 1 1 d . . .
C0BA C 0.3313(2) 0.6029(2) 0.59038(17) 0.0533(5) Uani 1 1 d . . .
H0BA H 0.3892 0.5554 0.6360 0.064 Uiso 1 1 calc R . .
C1BA C 0.6627(3) 0.1689(3) 0.82238(19) 0.0662(6) Uani 1 1 d . . .
H1BA H 0.7440 0.1235 0.8351 0.079 Uiso 1 1 calc R . .
C2BA C 0.7869(3) 0.6793(2) 0.98994(17) 0.0576(5) Uani 1 1 d . . .
H2BA H 0.8739 0.6424 1.0116 0.069 Uiso 1 1 calc R . .
C3BA C 0.5295(3) 0.7935(3) 0.92987(19) 0.0623(5) Uani 1 1 d . . .
H3BA H 0.4438 0.8325 0.9105 0.075 Uiso 1 1 calc R . .
C4BA C 0.0012(2) 0.7572(2) 0.59297(17) 0.0509(5) Uani 1 1 d . . .
C5BA C 0.2063(2) 0.6492(2) 0.61461(15) 0.0464(4) Uani 1 1 d . . .
C6BA C 0.6877(3) 0.8962(3) 1.0038(2) 0.0689(6) Uani 1 1 d . . .
H6BA H 0.7099 1.0052 1.0334 0.083 Uiso 1 1 calc R . .
C7BA C 0.3658(3) 0.6304(3) 0.49601(19) 0.0604(5) Uani 1 1 d . . .
H7BA H 0.4490 0.6009 0.4783 0.072 Uiso 1 1 calc R . .
C8BA C 0.1566(3) 0.7455(3) 0.45079(18) 0.0630(5) Uani 1 1 d . . .
H8BA H 0.0985 0.7919 0.4041 0.076 Uiso 1 1 calc R . .
C C 0.1815(3) 0.5689(3) 0.78859(17) 0.0578(5) Uani 1 1 d . . .
C9BA C 0.3774(3) 0.1398(3) 0.73163(19) 0.0664(6) Uani 1 1 d . . .
H9BA H 0.2666 0.0750 0.6839 0.080 Uiso 1 1 calc R . .
C0CA C -0.1940(3) 0.7994(3) 0.7207(2) 0.0684(6) Uani 1 1 d . . .
H0CA H -0.2607 0.8142 0.7630 0.082 Uiso 1 1 calc R . .
C1CA C -0.0826(3) 0.7251(3) 0.75403(19) 0.0613(5) Uani 1 1 d . . .
H1CA H -0.0737 0.6893 0.8176 0.074 Uiso 1 1 calc R . .
C2CA C 0.8160(3) 0.8384(3) 1.0349(2) 0.0681(6) Uani 1 1 d . . .
H2CA H 0.9227 0.9087 1.0868 0.082 Uiso 1 1 calc R . .
C3CA C -0.1124(3) 0.8314(3) 0.5612(2) 0.0646(6) Uani 1 1 d . . .
H3CA H -0.1230 0.8662 0.4972 0.078 Uiso 1 1 calc R . .
C4CA C 0.4972(3) 0.0732(3) 0.7500(2) 0.0703(6) Uani 1 1 d . . .
H4CA H 0.4679 -0.0359 0.7141 0.084 Uiso 1 1 calc R . .
C5CA C -0.2084(3) 0.8522(3) 0.6258(2) 0.0701(6) Uani 1 1 d . . .
H5CA H -0.2839 0.9023 0.6056 0.084 Uiso 1 1 calc R . .
C6CA C 0.2805(3) 0.7005(3) 0.42686(19) 0.0672(6) Uani 1 1 d . . .
H6CA H 0.3071 0.7172 0.3640 0.081 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
N0AA C7AA 1.298(3) . ?
N0AA C5AA 1.390(2) . ?
N1AA C 1.376(2) . ?
N1AA C5BA 1.426(2) . ?
N1AA C6AA 1.431(2) . ?
C2AA C3BA 1.401(3) . ?
C2AA C3AA 1.412(3) . ?
C2AA C7AA 1.443(3) . ?
C3AA C2BA 1.411(3) . ?
C3AA C4AA 1.444(3) . ?
C4AA C5AA 1.409(3) . ?
C4AA C8AA 1.411(3) . ?
O0AA C 1.209(3) . ?
C5AA C9BA 1.396(3) . ?
C6AA C1CA 1.385(3) . ?
C6AA C4BA 1.393(3) . ?
C7AA C 1.514(3) . ?
C8AA C1BA 1.365(3) . ?
C9AA C8BA 1.382(3) . ?
C9AA C5BA 1.404(2) . ?
C9AA C4BA 1.446(3) . ?
C0BA C7BA 1.381(3) . ?
C0BA C5BA 1.393(3) . ?
C1BA C4CA 1.390(3) . ?
C2BA C2CA 1.366(3) . ?
C3BA C6BA 1.365(3) . ?
C4BA C3CA 1.394(3) . ?
C6BA C2CA 1.392(3) . ?
C7BA C6CA 1.385(3) . ?
C8BA C6CA 1.377(3) . ?
C9BA C4CA 1.368(3) . ?
C0CA C1CA 1.383(3) . ?
C0CA C5CA 1.384(3) . ?
C3CA C5CA 1.373(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
C7AA N0AA C5AA 117.94(17) . . ?
C N1AA C5BA 129.16(15) . . ?
C N1AA C6AA 122.97(16) . . ?
C5BA N1AA C6AA 107.79(14) . . ?
C3BA C2AA C3AA 119.82(18) . . ?
C3BA C2AA C7AA 122.48(18) . . ?
C3AA C2AA C7AA 117.70(18) . . ?
C2BA C3AA C2AA 118.26(18) . . ?
C2BA C3AA C4AA 123.90(17) . . ?
C2AA C3AA C4AA 117.84(17) . . ?
C5AA C4AA C8AA 117.77(18) . . ?
C5AA C4AA C3AA 118.73(17) . . ?
C8AA C4AA C3AA 123.50(18) . . ?
N0AA C5AA C9BA 117.67(18) . . ?
N0AA C5AA C4AA 122.57(18) . . ?
C9BA C5AA C4AA 119.76(18) . . ?
C1CA C6AA C4BA 121.68(18) . . ?
C1CA C6AA N1AA 130.13(18) . . ?
C4BA C6AA N1AA 108.19(16) . . ?
N0AA C7AA C2AA 125.17(17) . . ?
N0AA C7AA C 115.34(18) . . ?
C2AA C7AA C 119.12(18) . . ?
C1BA C8AA C4AA 121.3(2) . . ?
C8BA C9AA C5BA 120.33(18) . . ?
C8BA C9AA C4BA 131.94(18) . . ?
C5BA C9AA C4BA 107.73(17) . . ?
C7BA C0BA C5BA 117.41(18) . . ?
C8AA C1BA C4CA 120.3(2) . . ?
C2CA C2BA C3AA 120.53(19) . . ?
C6BA C3BA C2AA 120.37(19) . . ?
C6AA C4BA C3CA 119.53(19) . . ?
C6AA C4BA C9AA 108.16(16) . . ?
C3CA C4BA C9AA 132.30(19) . . ?
C0BA C5BA C9AA 120.77(17) . . ?
C0BA C5BA N1AA 131.10(16) . . ?
C9AA C5BA N1AA 108.13(15) . . ?
C3BA C6BA C2CA 120.2(2) . . ?
C0BA C7BA C6CA 122.2(2) . . ?
C6CA C8BA C9AA 119.04(19) . . ?
O0AA C N1AA 121.73(18) . . ?
O0AA C C7AA 118.30(17) . . ?
N1AA C C7AA 119.95(17) . . ?
C4CA C9BA C5AA 121.0(2) . . ?
C1CA C0CA C5CA 121.5(2) . . ?
C0CA C1CA C6AA 117.5(2) . . ?
C2BA C2CA C6BA 120.7(2) . . ?
C5CA C3CA C4BA 119.0(2) . . ?
C9BA C4CA C1BA 119.8(2) . . ?
C3CA C5CA C0CA 120.71(19) . . ?
C8BA C6CA C7BA 120.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        66.78
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
