# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_twin4
_audit_block_doi                 10.5517/ccdc.csd.cc29l5gk
_database_code_depnum_ccdc_archive 'CCDC 2132628'
loop_
_audit_author_name
_audit_author_address
'Erik Ouellette'
;University of Berkeley
United States of America
;
_audit_update_record             
;
2022-01-05 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H8 N4 O2'
_chemical_formula_sum            'C18 H8 N4 O2'
_chemical_formula_weight         312.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 'Calculated using XDISP in WinGX (Farrugia, 1999)'
H H 0.0000 0.0000 'Calculated using XDISP in WinGX (Farrugia, 1999)'
N N 0.0065 0.0035 'Calculated using XDISP in WinGX (Farrugia, 1999)'
O O 0.0115 0.0064 'Calculated using XDISP in WinGX (Farrugia, 1999)'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6574(7)
_cell_length_b                   11.6570(8)
_cell_length_c                   10.8159(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.605(3)
_cell_angle_gamma                90
_cell_volume                     1328.57(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    45081
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.145
_cell_measurement_theta_min      2.566
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.745820
_exptl_absorpt_correction_T_min  0.630039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 45081 reflections, Rint = 0.1161
 (24412 with I > 3sig(I), Rint = 0.0862)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3319
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         29.145
_diffrn_reflns_theta_min         2.566
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source, station 12.2.1'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON-II CPAD detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2563
_reflns_number_total             3319
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker APEX3 Bruker, Madison WI'
_computing_cell_refinement       'SAINT V8.38A Bruker, Madison WI'
_computing_data_reduction        'SAINT V8.38A Bruker, Madison WI'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.5082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1401
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.500(3)
 0.500(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C7(H7), C1(H1), C6(H6), C4(H4), C5(H5), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1 O 0.38192(14) 1.05158(11) 0.31523(13) 0.0251(3) Uani 1 1 d . . . . .
O2 O 0.48907(15) 1.06568(12) 0.16132(14) 0.0293(4) Uani 1 1 d . . . . .
N1 N 0.33603(15) 0.72849(12) 0.48593(14) 0.0173(3) Uani 1 1 d . . . . .
N4 N 0.43647(16) 1.00905(14) 0.23414(14) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.32048(18) 1.00475(14) 0.57635(16) 0.0265(4) Uani 1 1 d . . . . .
N3 N 0.53237(19) 0.63151(15) -0.09785(16) 0.0288(4) Uani 1 1 d . . . . .
C15 C 0.39596(17) 0.81600(15) 0.31945(16) 0.0166(4) Uani 1 1 d . . . . .
C9 C 0.35596(17) 0.64127(15) 0.40614(16) 0.0169(4) Uani 1 1 d . . . . .
C10 C 0.39321(17) 0.69362(15) 0.29946(16) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.34278(17) 0.52515(16) 0.44596(17) 0.0172(4) Uani 1 1 d . . . . .
C16 C 0.35866(17) 0.83585(16) 0.43586(17) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.43614(17) 0.88470(15) 0.22475(17) 0.0175(4) Uani 1 1 d . . . . .
C11 C 0.42693(18) 0.64594(16) 0.19011(17) 0.0177(4) Uani 1 1 d . . . . .
H11 H 0.4225 0.5654 0.1765 0.021 Uiso 1 1 calc R U . . .
C3 C 0.30471(18) 0.50660(16) 0.56477(17) 0.0192(4) Uani 1 1 d . . . . .
C13 C 0.47166(17) 0.83807(16) 0.11971(17) 0.0185(4) Uani 1 1 d . . . . .
H13 H 0.4997 0.8861 0.0583 0.022 Uiso 1 1 calc R U . . .
C7 C 0.36838(18) 0.42913(16) 0.37529(17) 0.0192(4) Uani 1 1 d . . . . .
H7 H 0.3936 0.4399 0.2955 0.023 Uiso 1 1 calc R U . . .
C12 C 0.46662(18) 0.71805(16) 0.10259(16) 0.0192(4) Uani 1 1 d . . . . .
C1 C 0.30163(19) 0.70960(17) 0.60258(17) 0.0211(4) Uani 1 1 d . . . . .
H1 H 0.2898 0.7727 0.6553 0.025 Uiso 1 1 calc R U . . .
C18 C 0.50258(19) 0.66990(16) -0.00980(17) 0.0209(4) Uani 1 1 d . . . . .
C17 C 0.33946(18) 0.93359(16) 0.50778(17) 0.0199(4) Uani 1 1 d . . . . .
C6 C 0.35736(18) 0.31992(16) 0.42021(19) 0.0220(4) Uani 1 1 d . . . . .
H6 H 0.3767 0.2561 0.3718 0.026 Uiso 1 1 calc R U . . .
C4 C 0.29191(19) 0.39357(17) 0.60694(18) 0.0222(4) Uani 1 1 d . . . . .
H4 H 0.2647 0.3809 0.6856 0.027 Uiso 1 1 calc R U . . .
C5 C 0.31807(18) 0.30152(17) 0.53619(19) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.3095 0.2256 0.5658 0.028 Uiso 1 1 calc R U . . .
C2 C 0.28510(19) 0.60217(16) 0.64108(17) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.2599 0.5897 0.7206 0.026 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
O1 N4 1.227(2) . ?
O2 N4 1.226(2) . ?
N1 C9 1.371(2) . ?
N1 C16 1.399(2) . ?
N1 C1 1.383(2) . ?
N4 C14 1.453(2) . ?
N2 C17 1.151(2) . ?
N3 C18 1.139(2) . ?
C15 C10 1.443(2) . ?
C15 C16 1.395(2) . ?
C15 C14 1.416(2) . ?
C9 C10 1.414(2) . ?
C9 C8 1.434(2) . ?
C10 C11 1.401(2) . ?
C8 C3 1.421(2) . ?
C8 C7 1.405(3) . ?
C16 C17 1.412(3) . ?
C14 C13 1.363(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C3 C4 1.408(3) . ?
C3 C2 1.420(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.411(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.374(3) . ?
C12 C18 1.442(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.340(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(3) . ?
C5 H5 0.9500 . ?
C2 H2 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
C9 N1 C16 111.59(14) . . ?
C9 N1 C1 122.92(15) . . ?
C1 N1 C16 125.46(15) . . ?
O1 N4 C14 117.17(15) . . ?
O2 N4 O1 123.56(16) . . ?
O2 N4 C14 119.27(15) . . ?
C16 C15 C10 107.29(16) . . ?
C16 C15 C14 135.79(17) . . ?
C14 C15 C10 116.90(15) . . ?
N1 C9 C10 106.41(15) . . ?
N1 C9 C8 118.68(15) . . ?
C10 C9 C8 134.82(16) . . ?
C9 C10 C15 107.84(15) . . ?
C11 C10 C15 121.11(16) . . ?
C11 C10 C9 131.03(17) . . ?
C3 C8 C9 117.99(16) . . ?
C7 C8 C9 123.57(16) . . ?
C7 C8 C3 118.42(17) . . ?
N1 C16 C17 117.46(15) . . ?
C15 C16 N1 106.85(16) . . ?
C15 C16 C17 135.69(17) . . ?
C15 C14 N4 120.76(15) . . ?
C13 C14 N4 117.26(16) . . ?
C13 C14 C15 121.94(17) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.77(17) . . ?
C12 C11 H11 120.6 . . ?
C4 C3 C8 119.35(17) . . ?
C4 C3 C2 121.07(17) . . ?
C2 C3 C8 119.54(17) . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.66(17) . . ?
C12 C13 H13 120.2 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.80(17) . . ?
C6 C7 H7 119.6 . . ?
C11 C12 C13 121.59(16) . . ?
C11 C12 C18 119.27(17) . . ?
C13 C12 C18 119.13(17) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 N1 119.84(17) . . ?
C2 C1 H1 120.1 . . ?
N3 C18 C12 179.2(2) . . ?
N2 C17 C16 172.3(2) . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.84(18) . . ?
C5 C6 H6 119.6 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.95(18) . . ?
C5 C4 H4 119.5 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.63(17) . . ?
C4 C5 H5 120.2 . . ?
C3 C2 H2 119.5 . . ?
C1 C2 C3 120.99(17) . . ?
C1 C2 H2 119.5 . . ?

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
O1 N4 C14 C15 -11.6(3) . . . . ?
O1 N4 C14 C13 166.20(17) . . . . ?
O2 N4 C14 C15 169.14(17) . . . . ?
O2 N4 C14 C13 -13.1(3) . . . . ?
N1 C9 C10 C15 0.6(2) . . . . ?
N1 C9 C10 C11 179.01(19) . . . . ?
N1 C9 C8 C3 2.4(3) . . . . ?
N1 C9 C8 C7 -176.00(17) . . . . ?
N1 C1 C2 C3 1.2(3) . . . . ?
N4 C14 C13 C12 -176.64(17) . . . . ?
C15 C10 C11 C12 1.8(3) . . . . ?
C15 C14 C13 C12 1.1(3) . . . . ?
C9 N1 C16 C15 -0.6(2) . . . . ?
C9 N1 C16 C17 178.93(17) . . . . ?
C9 N1 C1 C2 -0.7(3) . . . . ?
C9 C10 C11 C12 -176.42(19) . . . . ?
C9 C8 C3 C4 -179.49(17) . . . . ?
C9 C8 C3 C2 -2.0(3) . . . . ?
C9 C8 C7 C6 178.14(18) . . . . ?
C10 C15 C16 N1 1.0(2) . . . . ?
C10 C15 C16 C17 -178.5(2) . . . . ?
C10 C15 C14 N4 177.20(16) . . . . ?
C10 C15 C14 C13 -0.5(3) . . . . ?
C10 C9 C8 C3 178.4(2) . . . . ?
C10 C9 C8 C7 0.0(3) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C10 C11 C12 C18 179.48(18) . . . . ?
C8 C9 C10 C15 -175.7(2) . . . . ?
C8 C9 C10 C11 2.7(4) . . . . ?
C8 C3 C4 C5 1.3(3) . . . . ?
C8 C3 C2 C1 0.2(3) . . . . ?
C8 C7 C6 C5 1.2(3) . . . . ?
C16 N1 C9 C10 0.0(2) . . . . ?
C16 N1 C9 C8 177.04(16) . . . . ?
C16 N1 C1 C2 -178.63(18) . . . . ?
C16 C15 C10 C9 -1.0(2) . . . . ?
C16 C15 C10 C11 -179.58(17) . . . . ?
C16 C15 C14 N4 -4.8(3) . . . . ?
C16 C15 C14 C13 177.5(2) . . . . ?
C14 C15 C10 C9 177.60(16) . . . . ?
C14 C15 C10 C11 -1.0(3) . . . . ?
C14 C15 C16 N1 -177.2(2) . . . . ?
C14 C15 C16 C17 3.4(4) . . . . ?
C14 C13 C12 C11 -0.3(3) . . . . ?
C14 C13 C12 C18 179.06(18) . . . . ?
C3 C8 C7 C6 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C7 C8 C3 C4 -1.0(3) . . . . ?
C7 C8 C3 C2 176.52(17) . . . . ?
C7 C6 C5 C4 -0.9(3) . . . . ?
C1 N1 C9 C10 -178.13(17) . . . . ?
C1 N1 C9 C8 -1.1(3) . . . . ?
C1 N1 C16 C15 177.47(18) . . . . ?
C1 N1 C16 C17 -3.0(3) . . . . ?
C4 C3 C2 C1 177.7(2) . . . . ?
C2 C3 C4 C5 -176.16(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.500(3)
2 0.500(3)

