# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_xt9
_database_code_depnum_ccdc_archive 'CCDC 2009092'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2021-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            '3af in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.33

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.2339(2)
_cell_length_b                   16.5540(3)
_cell_length_c                   18.3374(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3106.58(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.47

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9044
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32075
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         27.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3434
_reflns_number_gt                2821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+1.3511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3434
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.38030(11) 0.55324(7) 0.63811(6) 0.0289(3) Uani 1 1 d . . . . .
C2 C 0.46000(15) 0.60598(9) 0.67462(8) 0.0337(3) Uani 1 1 d . . . . .
O2 O 0.43811(12) 0.67318(7) 0.69693(7) 0.0469(3) Uani 1 1 d . . . . .
O3 O 0.57769(10) 0.56858(6) 0.68221(6) 0.0345(3) Uani 1 1 d . . . . .
C4 C 0.56953(14) 0.49116(8) 0.65165(8) 0.0295(3) Uani 1 1 d . . . . .
C5 C 0.44988(13) 0.48131(8) 0.62313(7) 0.0268(3) Uani 1 1 d . . . . .
C11 C 0.25386(14) 0.57567(8) 0.61161(7) 0.0275(3) Uani 1 1 d . . . . .
N12 N 0.23042(12) 0.55606(8) 0.54274(6) 0.0327(3) Uani 1 1 d . . . . .
C13 C 0.11197(15) 0.57546(10) 0.51716(9) 0.0397(4) Uani 1 1 d . . . . .
H13 H 0.091437 0.561577 0.468219 0.048 Uiso 1 1 calc R U . . .
C14 C 0.01817(15) 0.61450(10) 0.55805(10) 0.0438(4) Uani 1 1 d . . . . .
H14 H -0.065062 0.626393 0.537778 0.053 Uiso 1 1 calc R U . . .
C15 C 0.04717(15) 0.63593(10) 0.62866(10) 0.0419(4) Uani 1 1 d . . . . .
H15 H -0.015041 0.664076 0.657517 0.050 Uiso 1 1 calc R U . . .
C16 C 0.16782(15) 0.61603(9) 0.65705(8) 0.0349(3) Uani 1 1 d . . . . .
H16 H 0.190862 0.629468 0.705748 0.042 Uiso 1 1 calc R U . . .
C21 C 0.68366(14) 0.44028(9) 0.66351(7) 0.0307(3) Uani 1 1 d . . . . .
C22 C 0.80489(15) 0.47591(10) 0.67620(8) 0.0368(3) Uani 1 1 d . . . . .
H22 H 0.812844 0.533085 0.675550 0.044 Uiso 1 1 calc R U . . .
C23 C 0.91387(16) 0.42865(12) 0.68975(9) 0.0433(4) Uani 1 1 d . . . . .
H23 H 0.996266 0.453502 0.697880 0.052 Uiso 1 1 calc R U . . .
C24 C 0.90317(17) 0.34576(12) 0.69146(9) 0.0465(4) Uani 1 1 d . . . . .
H24 H 0.977901 0.313453 0.701153 0.056 Uiso 1 1 calc R U . . .
C25 C 0.78324(18) 0.30964(11) 0.67903(9) 0.0457(4) Uani 1 1 d . . . . .
H25 H 0.776057 0.252435 0.680028 0.055 Uiso 1 1 calc R U . . .
C26 C 0.67344(16) 0.35631(10) 0.66513(9) 0.0390(4) Uani 1 1 d . . . . .
H26 H 0.591426 0.331100 0.656722 0.047 Uiso 1 1 calc R U . . .
C31 C 0.39042(13) 0.41105(8) 0.58661(7) 0.0266(3) Uani 1 1 d . . . . .
C32 C 0.44640(14) 0.38027(9) 0.52340(8) 0.0336(3) Uani 1 1 d . . . . .
H32 H 0.523057 0.404382 0.503914 0.040 Uiso 1 1 calc R U . . .
C33 C 0.39036(16) 0.31437(9) 0.48878(9) 0.0388(4) Uani 1 1 d . . . . .
H33 H 0.428796 0.293367 0.445603 0.047 Uiso 1 1 calc R U . . .
C34 C 0.27889(16) 0.27917(9) 0.51685(9) 0.0384(4) Uani 1 1 d . . . . .
H34 H 0.239896 0.234638 0.492469 0.046 Uiso 1 1 calc R U . . .
C35 C 0.22392(15) 0.30862(9) 0.58035(9) 0.0372(4) Uani 1 1 d . . . . .
H35 H 0.148303 0.283604 0.600177 0.045 Uiso 1 1 calc R U . . .
C36 C 0.27928(14) 0.37477(9) 0.61515(8) 0.0314(3) Uani 1 1 d . . . . .
H36 H 0.241046 0.395262 0.658581 0.038 Uiso 1 1 calc R U . . .


_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 C2 1.3697(19) . ?
N1 C5 1.4143(18) . ?
N1 C11 1.4313(17) . ?
C2 O2 1.2061(18) . ?
C2 O3 1.3614(18) . ?
O3 C4 1.4013(17) . ?
C4 C5 1.3414(19) . ?
C4 C21 1.456(2) . ?
C5 C31 1.4737(19) . ?
C11 N12 1.3258(18) . ?
C11 C16 1.384(2) . ?
N12 C13 1.3389(19) . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.393(2) . ?
C21 C26 1.394(2) . ?
C22 C23 1.385(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.3885(19) . ?
C31 C32 1.3898(19) . ?
C32 C33 1.386(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.381(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

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
C2 N1 C5 109.38(12) . . ?
C2 N1 C11 122.61(12) . . ?
C5 N1 C11 127.43(11) . . ?
O2 C2 O3 123.31(14) . . ?
O2 C2 N1 130.02(15) . . ?
O3 C2 N1 106.67(12) . . ?
C2 O3 C4 108.81(11) . . ?
C5 C4 O3 108.75(12) . . ?
C5 C4 C21 136.06(14) . . ?
O3 C4 C21 114.92(12) . . ?
C4 C5 N1 106.36(12) . . ?
C4 C5 C31 130.54(13) . . ?
N1 C5 C31 123.01(12) . . ?
N12 C11 C16 125.21(14) . . ?
N12 C11 N1 115.05(12) . . ?
C16 C11 N1 119.73(13) . . ?
C11 N12 C13 116.02(13) . . ?
N12 C13 C14 123.52(15) . . ?
N12 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C15 C14 C13 118.86(15) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.14(15) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 117.21(15) . . ?
C15 C16 H16 121.4 . . ?
C11 C16 H16 121.4 . . ?
C22 C21 C26 119.03(14) . . ?
C22 C21 C4 119.62(14) . . ?
C26 C21 C4 121.30(14) . . ?
C23 C22 C21 120.53(16) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.20(16) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.82(16) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.52(17) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 119.89(16) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
C36 C31 C32 119.57(13) . . ?
C36 C31 C5 120.56(12) . . ?
C32 C31 C5 119.88(13) . . ?
C33 C32 C31 119.99(14) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.22(14) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 120.10(14) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C34 C35 C36 119.96(14) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 120.14(14) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?

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
C5 N1 C2 O2 179.89(16) . . . . ?
C11 N1 C2 O2 8.1(3) . . . . ?
C5 N1 C2 O3 0.38(15) . . . . ?
C11 N1 C2 O3 -171.44(12) . . . . ?
O2 C2 O3 C4 178.98(15) . . . . ?
N1 C2 O3 C4 -1.47(15) . . . . ?
C2 O3 C4 C5 2.08(15) . . . . ?
C2 O3 C4 C21 -172.96(12) . . . . ?
O3 C4 C5 N1 -1.77(15) . . . . ?
C21 C4 C5 N1 171.74(15) . . . . ?
O3 C4 C5 C31 -178.33(13) . . . . ?
C21 C4 C5 C31 -4.8(3) . . . . ?
C2 N1 C5 C4 0.89(15) . . . . ?
C11 N1 C5 C4 172.21(13) . . . . ?
C2 N1 C5 C31 177.77(13) . . . . ?
C11 N1 C5 C31 -10.9(2) . . . . ?
C2 N1 C11 N12 131.06(14) . . . . ?
C5 N1 C11 N12 -39.21(19) . . . . ?
C2 N1 C11 C16 -47.90(19) . . . . ?
C5 N1 C11 C16 141.83(14) . . . . ?
C16 C11 N12 C13 -2.0(2) . . . . ?
N1 C11 N12 C13 179.06(12) . . . . ?
C11 N12 C13 C14 0.9(2) . . . . ?
N12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -1.6(2) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
N12 C11 C16 C15 1.3(2) . . . . ?
N1 C11 C16 C15 -179.81(13) . . . . ?
C5 C4 C21 C22 161.92(16) . . . . ?
O3 C4 C21 C22 -24.85(19) . . . . ?
C5 C4 C21 C26 -20.5(3) . . . . ?
O3 C4 C21 C26 152.75(14) . . . . ?
C26 C21 C22 C23 0.4(2) . . . . ?
C4 C21 C22 C23 178.08(14) . . . . ?
C21 C22 C23 C24 -0.6(2) . . . . ?
C22 C23 C24 C25 0.5(2) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?
C22 C21 C26 C25 -0.2(2) . . . . ?
C4 C21 C26 C25 -177.79(14) . . . . ?
C4 C5 C31 C36 119.56(17) . . . . ?
N1 C5 C31 C36 -56.50(19) . . . . ?
C4 C5 C31 C32 -59.9(2) . . . . ?
N1 C5 C31 C32 124.02(15) . . . . ?
C36 C31 C32 C33 0.8(2) . . . . ?
C5 C31 C32 C33 -179.74(13) . . . . ?
C31 C32 C33 C34 0.1(2) . . . . ?
C32 C33 C34 C35 -1.1(2) . . . . ?
C33 C34 C35 C36 1.4(2) . . . . ?
C34 C35 C36 C31 -0.5(2) . . . . ?
C32 C31 C36 C35 -0.6(2) . . . . ?
C5 C31 C36 C35 179.97(13) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038




#==================================================================

