# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 2191373'
loop_
_audit_author_name
_audit_author_address
Tatiana
;Staff University of Alicante
Spain
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O2'
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40
_chemical_absolute_configuration syn

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           orthorhombic
_symmetry_space_group_name_H-M   'P 212121'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   8.0523(17)
_cell_length_b                   13.171(3)
_cell_length_c                   17.268(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1831.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(1)
_cell_measurement_reflns_used    1329
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      19.7

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7910
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(1)
_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            15451
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.08
_reflns_number_total             3248
_reflns_number_gt                2004
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART V5.625'
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0421P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         3248
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8697(3) 0.88622(16) 0.16945(12) 0.0442(6) Uani 1 1 d . . .
C1 C 0.9317(4) 0.8210(2) 0.11399(15) 0.0498(7) Uani 1 1 d . . .
O1 O 0.9674(3) 0.73354(16) 0.12693(11) 0.0706(7) Uani 1 1 d . . .
C2 C 0.9447(4) 0.8760(2) 0.03783(15) 0.0486(7) Uani 1 1 d . . .
H2 H 1.0602 0.8849 0.0213 0.058 Uiso 1 1 calc R . .
C3 C 0.8400(4) 0.8212(2) -0.02333(14) 0.0535(8) Uani 1 1 d . . .
H3 H 0.8427 0.7480 -0.0131 0.064 Uiso 1 1 calc R . .
C4 C 0.8964(4) 0.8399(2) -0.10388(17) 0.0594(9) Uani 1 1 d . . .
C5 C 0.9331(5) 0.8505(3) -0.1678(2) 0.0806(11) Uani 1 1 d . . .
H5 H 0.9628 0.8590 -0.2194 0.097 Uiso 1 1 calc R . .
N2 N 0.6755(3) 0.86013(18) -0.00457(13) 0.0547(7) Uani 1 1 d . . .
H2N H 0.609(3) 0.844(2) -0.0410(16) 0.066 Uiso 1 1 d . . .
C6 C 0.6906(3) 0.9698(2) 0.00747(15) 0.0492(7) Uani 1 1 d . . .
H6 H 0.7036 1.0032 -0.0429 0.059 Uiso 1 1 calc R . .
C7 C 0.5393(4) 1.0122(3) 0.04738(17) 0.0572(8) Uani 1 1 d . . .
C8 C 0.4863(5) 1.1091(3) 0.0304(2) 0.0802(11) Uani 1 1 d . . .
H8 H 0.5418 1.1478 -0.0064 0.096 Uiso 1 1 calc R . .
C9 C 0.3474(6) 1.1492(4) 0.0694(3) 0.1071(15) Uani 1 1 d . . .
H9 H 0.3103 1.2143 0.0578 0.129 Uiso 1 1 calc R . .
C10 C 0.2668(6) 1.0928(5) 0.1242(3) 0.1183(19) Uani 1 1 d . . .
H10 H 0.1766 1.1202 0.1505 0.142 Uiso 1 1 calc R . .
C11 C 0.3185(5) 0.9965(4) 0.1405(2) 0.1012(14) Uani 1 1 d . . .
H11 H 0.2623 0.9583 0.1774 0.121 Uiso 1 1 calc R . .
C12 C 0.4536(4) 0.9553(3) 0.10244(18) 0.0705(10) Uani 1 1 d . . .
H12 H 0.4875 0.8895 0.1136 0.085 Uiso 1 1 calc R . .
C13 C 0.8583(3) 0.9774(2) 0.05302(14) 0.0466(7) Uani 1 1 d . . .
H13 H 0.9256 1.0343 0.0343 0.056 Uiso 1 1 calc R . .
C14 C 0.8366(3) 0.9820(2) 0.13930(15) 0.0473(7) Uani 1 1 d . . .
O2 O 0.7976(3) 1.05495(14) 0.17776(11) 0.0620(6) Uani 1 1 d . . .
C15 C 0.8539(4) 0.8525(2) 0.25093(15) 0.0487(7) Uani 1 1 d . . .
H15 H 0.8496 0.7781 0.2496 0.058 Uiso 1 1 calc R . .
C16 C 0.6909(4) 0.8872(2) 0.28699(16) 0.0639(9) Uani 1 1 d . . .
H16A H 0.6002 0.8677 0.2541 0.096 Uiso 1 1 calc R . .
H16B H 0.6919 0.9597 0.2927 0.096 Uiso 1 1 calc R . .
H16C H 0.6778 0.8562 0.3369 0.096 Uiso 1 1 calc R . .
C17 C 1.0082(4) 0.8799(2) 0.29635(14) 0.0460(7) Uani 1 1 d . . .
C18 C 1.0408(4) 0.9783(2) 0.32067(15) 0.0536(8) Uani 1 1 d . . .
H18 H 0.9646 1.0297 0.3106 0.064 Uiso 1 1 calc R . .
C19 C 1.1854(4) 1.0002(2) 0.35960(17) 0.0647(9) Uani 1 1 d . . .
H19 H 1.2075 1.0666 0.3749 0.078 Uiso 1 1 calc R . .
C20 C 1.2973(4) 0.9245(3) 0.37607(18) 0.0744(10) Uani 1 1 d . . .
H20 H 1.3945 0.9397 0.4028 0.089 Uiso 1 1 calc R . .
C21 C 1.2663(4) 0.8274(3) 0.35335(19) 0.0743(10) Uani 1 1 d . . .
H21 H 1.3420 0.7763 0.3648 0.089 Uiso 1 1 calc R . .
C22 C 1.1220(4) 0.8045(2) 0.31316(17) 0.0600(9) Uani 1 1 d . . .
H22 H 1.1018 0.7381 0.2974 0.072 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 C1 1.380(3) . ?
N1 C14 1.390(3) . ?
N1 C15 1.481(3) . ?
C1 O1 1.208(3) . ?
C1 C2 1.505(4) . ?
C2 C13 1.529(3) . ?
C2 C3 1.532(4) . ?
C2 H2 0.9800 . ?
C3 N2 1.457(4) . ?
C3 C4 1.484(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.151(4) . ?
C5 H5 0.9300 . ?
N2 C6 1.464(3) . ?
N2 H2N 0.85(3) . ?
C6 C7 1.507(4) . ?
C6 C13 1.566(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.377(4) . ?
C7 C12 1.393(4) . ?
C8 C9 1.407(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.501(4) . ?
C13 H13 0.9800 . ?
C14 O2 1.210(3) . ?
C15 C17 1.514(4) . ?
C15 C16 1.523(4) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.382(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.375(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.361(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
C1 N1 C14 112.0(2) . . ?
C1 N1 C15 120.2(2) . . ?
C14 N1 C15 127.7(2) . . ?
O1 C1 N1 123.5(3) . . ?
O1 C1 C2 127.2(3) . . ?
N1 C1 C2 109.4(3) . . ?
C1 C2 C13 103.8(2) . . ?
C1 C2 C3 109.7(2) . . ?
C13 C2 C3 106.3(2) . . ?
C1 C2 H2 112.2 . . ?
C13 C2 H2 112.2 . . ?
C3 C2 H2 112.2 . . ?
N2 C3 C4 115.4(2) . . ?
N2 C3 C2 100.4(2) . . ?
C4 C3 C2 113.5(3) . . ?
N2 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C5 C4 C3 176.0(4) . . ?
C4 C5 H5 180.0 . . ?
C3 N2 C6 107.7(2) . . ?
C3 N2 H2N 108.3(19) . . ?
C6 N2 H2N 114(2) . . ?
N2 C6 C7 111.3(2) . . ?
N2 C6 C13 101.9(2) . . ?
C7 C6 C13 116.3(2) . . ?
N2 C6 H6 109.0 . . ?
C7 C6 H6 109.0 . . ?
C13 C6 H6 109.0 . . ?
C8 C7 C12 119.3(3) . . ?
C8 C7 C6 119.8(3) . . ?
C12 C7 C6 120.9(3) . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.2(5) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.5(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C14 C13 C2 105.0(2) . . ?
C14 C13 C6 113.6(2) . . ?
C2 C13 C6 104.5(2) . . ?
C14 C13 H13 111.1 . . ?
C2 C13 H13 111.1 . . ?
C6 C13 H13 111.1 . . ?
O2 C14 N1 124.4(2) . . ?
O2 C14 C13 127.4(3) . . ?
N1 C14 C13 108.2(2) . . ?
N1 C15 C17 110.5(2) . . ?
N1 C15 C16 111.9(2) . . ?
C17 C15 C16 115.1(2) . . ?
N1 C15 H15 106.3 . . ?
C17 C15 H15 106.3 . . ?
C16 C15 H15 106.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 118.8(3) . . ?
C22 C17 C15 118.8(3) . . ?
C18 C17 C15 122.4(3) . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.3(3) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.029
