# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_XH_1
_database_code_depnum_ccdc_archive 'CCDC 2201970'
loop_
_audit_author_name
_audit_author_address
'Frank R Fronczek'
;Louisiana State University
United States of America
;
_audit_update_record             
;
2022-08-17 deposited with the CCDC.	2023-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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'
'-y, x, z+1/4'
'y, -x, z+3/4'
'-x, -y, z+1/2'

_cell_length_a                   5.3375(6)
_cell_length_b                   5.3375(6)
_cell_length_c                   52.802(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1504.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      28.10
_exptl_crystal_description       Triangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33370
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_limit_l_max       67
_diffrn_reflns_theta_min         1.157
_diffrn_reflns_theta_max         30.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3562
_reflns_number_gt                3508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_max     0.801
_reflns_Friedel_fraction_full    1.000

_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+1.4807P] 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_abs_structure_details 
;
 Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3562
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.160
_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
O1 O 0.5523(5) 1.0328(6) 0.46443(6) 0.0237(6) Uani 1 1 d . . . . .
O2 O 0.5582(6) 0.2416(5) 0.54681(5) 0.0243(6) Uani 1 1 d . . . . .
C1 C 0.8877(7) 1.6381(7) 0.39381(7) 0.0181(7) Uani 1 1 d . . . . .
H1 H 0.877557 1.767856 0.381542 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7008(7) 1.6117(7) 0.41219(7) 0.0177(7) Uani 1 1 d . . . . .
H2 H 0.565774 1.727592 0.412564 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7087(7) 1.4194(7) 0.42989(7) 0.0167(7) Uani 1 1 d . . . . .
H3 H 0.576815 1.400089 0.441809 0.020 Uiso 1 1 calc R U . . .
C4 C 0.9141(7) 1.2528(7) 0.43006(7) 0.0144(7) Uani 1 1 d . . . . .
C5 C 0.9570(7) 1.0558(7) 0.44864(7) 0.0157(7) Uani 1 1 d . . . . .
H5 H 1.121546 0.988801 0.449724 0.019 Uiso 1 1 calc R U . . .
N2 N 0.7869(6) 0.9625(6) 0.46409(6) 0.0143(6) Uani 1 1 d . . . . .
C7 C 0.8552(7) 0.7672(7) 0.48226(7) 0.0151(7) Uani 1 1 d . . . . .
C8 C 0.6882(7) 0.7247(7) 0.50201(7) 0.0138(7) Uani 1 1 d . . . . .
H8 H 0.543618 0.826568 0.504030 0.017 Uiso 1 1 calc R U . . .
C9 C 0.7380(7) 0.5291(7) 0.51877(7) 0.0172(7) Uani 1 1 d . . . . .
N1 N 0.5654(6) 0.4753(6) 0.53951(6) 0.0178(7) Uani 1 1 d . . . . .
C11 C 0.4276(8) 0.6553(7) 0.54951(6) 0.0170(7) Uani 1 1 d . . . . .
H11 H 0.453127 0.819515 0.543079 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2416(7) 0.6282(7) 0.56925(6) 0.0135(7) Uani 1 1 d . . . . .
C13 C 0.2273(7) 0.4241(7) 0.58614(6) 0.0154(7) Uani 1 1 d . . . . .
H13 H 0.345523 0.291490 0.585073 0.018 Uiso 1 1 calc R U . . .
C14 C 0.0387(7) 0.4177(8) 0.60444(7) 0.0181(7) Uani 1 1 d . . . . .
H14 H 0.031004 0.281836 0.616038 0.022 Uiso 1 1 calc R U . . .
C15 C -0.1377(8) 0.6083(8) 0.60580(7) 0.0196(8) Uani 1 1 d . . . . .
H15 H -0.266449 0.601193 0.618198 0.024 Uiso 1 1 calc R U . . .
C16 C 1.0671(7) 0.6180(7) 0.47926(7) 0.0146(7) Uani 1 1 d . . . . .
H16 H 1.180404 0.648720 0.465741 0.017 Uiso 1 1 calc R U . . .
C17 C 1.1114(7) 0.4241(8) 0.49617(7) 0.0188(8) Uani 1 1 d . . . . .
H17 H 1.256882 0.323396 0.494235 0.023 Uiso 1 1 calc R U . . .
C18 C 0.9459(8) 0.3748(7) 0.51594(7) 0.0179(7) Uani 1 1 d . . . . .
H18 H 0.974302 0.238968 0.527209 0.022 Uiso 1 1 calc R U . . .
C19 C 0.0612(7) 0.8211(7) 0.57132(7) 0.0171(7) Uani 1 1 d . . . . .
H19 H 0.070092 0.960932 0.560221 0.020 Uiso 1 1 calc R U . . .
C20 C -0.1268(8) 0.8102(8) 0.58907(7) 0.0192(8) Uani 1 1 d . . . . .
H20 H -0.248833 0.939476 0.589943 0.023 Uiso 1 1 calc R U . . .
C21 C 1.1039(7) 1.2821(7) 0.41180(7) 0.0169(7) Uani 1 1 d . . . . .
H21 H 1.243563 1.171779 0.411779 0.020 Uiso 1 1 calc R U . . .
C22 C 1.0881(7) 1.4726(7) 0.39371(7) 0.0171(7) Uani 1 1 d . . . . .
H22 H 1.215554 1.488819 0.381259 0.020 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 N2 1.308(4) . ?
O2 N1 1.306(4) . ?
C1 C22 1.387(5) . ?
C1 C2 1.399(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.411(5) . ?
C3 H3 0.9500 . ?
C4 C21 1.407(5) . ?
C4 C5 1.457(5) . ?
C5 N2 1.318(5) . ?
C5 H5 0.9500 . ?
N2 C7 1.463(5) . ?
C7 C8 1.390(5) . ?
C7 C16 1.392(5) . ?
C8 C9 1.395(5) . ?
C8 H8 0.9500 . ?
C9 C18 1.390(6) . ?
C9 N1 1.459(5) . ?
N1 C11 1.320(5) . ?
C11 C12 1.447(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.410(5) . ?
C12 C19 1.414(5) . ?
C13 C14 1.395(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(6) . ?
C14 H14 0.9500 . ?
C15 C20 1.394(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.375(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.398(5) . ?
C21 H21 0.9500 . ?
C22 H22 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
C22 C1 C2 119.2(4) . . ?
C22 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C21 C4 C3 119.0(3) . . ?
C21 C4 C5 115.4(3) . . ?
C3 C4 C5 125.5(3) . . ?
N2 C5 C4 125.5(3) . . ?
N2 C5 H5 117.2 . . ?
C4 C5 H5 117.2 . . ?
O1 N2 C5 124.0(3) . . ?
O1 N2 C7 115.7(3) . . ?
C5 N2 C7 120.2(3) . . ?
C8 C7 C16 120.8(3) . . ?
C8 C7 N2 116.7(3) . . ?
C16 C7 N2 122.4(3) . . ?
C7 C8 C9 118.4(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C18 C9 C8 121.8(3) . . ?
C18 C9 N1 117.9(3) . . ?
C8 C9 N1 120.2(3) . . ?
O2 N1 C11 124.1(3) . . ?
O2 N1 C9 115.3(3) . . ?
C11 N1 C9 120.6(3) . . ?
N1 C11 C12 126.7(3) . . ?
N1 C11 H11 116.6 . . ?
C12 C11 H11 116.6 . . ?
C13 C12 C19 118.5(3) . . ?
C13 C12 C11 124.8(3) . . ?
C19 C12 C11 116.8(3) . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C20 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C20 C15 H15 119.8 . . ?
C17 C16 C7 119.5(3) . . ?
C17 C16 H16 120.3 . . ?
C7 C16 H16 120.3 . . ?
C16 C17 C18 121.0(4) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C9 C18 C17 118.4(4) . . ?
C9 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C20 C19 C12 121.3(3) . . ?
C20 C19 H19 119.4 . . ?
C12 C19 H19 119.4 . . ?
C19 C20 C15 119.7(4) . . ?
C19 C20 H20 120.2 . . ?
C15 C20 H20 120.2 . . ?
C22 C21 C4 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C4 C21 H21 119.8 . . ?
C1 C22 C21 120.5(3) . . ?
C1 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?

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
C22 C1 C2 C3 -1.7(6) . . . . ?
C1 C2 C3 C4 2.5(6) . . . . ?
C2 C3 C4 C21 -1.5(5) . . . . ?
C2 C3 C4 C5 174.9(3) . . . . ?
C21 C4 C5 N2 -165.8(3) . . . . ?
C3 C4 C5 N2 17.7(6) . . . . ?
C4 C5 N2 O1 1.3(6) . . . . ?
C4 C5 N2 C7 -178.9(3) . . . . ?
O1 N2 C7 C8 -16.5(5) . . . . ?
C5 N2 C7 C8 163.8(3) . . . . ?
O1 N2 C7 C16 159.2(3) . . . . ?
C5 N2 C7 C16 -20.5(5) . . . . ?
C16 C7 C8 C9 0.0(5) . . . . ?
N2 C7 C8 C9 175.8(3) . . . . ?
C7 C8 C9 C18 -1.2(5) . . . . ?
C7 C8 C9 N1 -178.9(3) . . . . ?
C18 C9 N1 O2 -27.1(5) . . . . ?
C8 C9 N1 O2 150.7(4) . . . . ?
C18 C9 N1 C11 153.5(4) . . . . ?
C8 C9 N1 C11 -28.6(5) . . . . ?
O2 N1 C11 C12 -2.2(6) . . . . ?
C9 N1 C11 C12 177.1(3) . . . . ?
N1 C11 C12 C13 19.7(6) . . . . ?
N1 C11 C12 C19 -159.6(4) . . . . ?
C19 C12 C13 C14 -0.5(5) . . . . ?
C11 C12 C13 C14 -179.8(4) . . . . ?
C12 C13 C14 C15 1.3(6) . . . . ?
C13 C14 C15 C20 -0.7(6) . . . . ?
C8 C7 C16 C17 0.2(5) . . . . ?
N2 C7 C16 C17 -175.3(3) . . . . ?
C7 C16 C17 C18 0.7(6) . . . . ?
C8 C9 C18 C17 2.0(6) . . . . ?
N1 C9 C18 C17 179.8(3) . . . . ?
C16 C17 C18 C9 -1.8(6) . . . . ?
C13 C12 C19 C20 -0.9(6) . . . . ?
C11 C12 C19 C20 178.5(3) . . . . ?
C12 C19 C20 C15 1.5(6) . . . . ?
C14 C15 C20 C19 -0.6(6) . . . . ?
C3 C4 C21 C22 -0.4(5) . . . . ?
C5 C4 C21 C22 -177.2(3) . . . . ?
C2 C1 C22 C21 -0.2(6) . . . . ?
C4 C21 C22 C1 1.2(6) . . . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.081



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-pentane/acetone'
