# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_KW1
_database_code_depnum_ccdc_archive 'CCDC 2386038'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University 
Canada
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        
6-(4-methoxypgenyl)pyridoxine[2,1-alpha]isoindole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

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'

_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                   16.4292(4)
_cell_length_b                   7.6601(2)
_cell_length_c                   22.9023(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2882.24(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1912
_cell_measurement_theta_min      3.860
_cell_measurement_theta_max      72.456

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    0.609
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5741
_exptl_absorpt_correction_T_max  0.7314
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41004
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.860
_diffrn_reflns_theta_max         72.456
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2849
_reflns_number_gt                1912
_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 APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'Bruker APEX3'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0730P)²+0.8646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2849
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1730
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.46488(11) -0.0180(3) 0.37162(8) 0.0602(6) Uani 0.629(18) 1 d . . P A 1
C8 C 0.58449(11) -0.0292(3) 0.32605(8) 0.0593(6) Uani 0.629(18) 1 d . . P A 1
C1 C 0.46488(11) -0.0180(3) 0.37162(8) 0.0602(6) Uani 0.371(18) 1 d . . P A 2
N8 N 0.58449(11) -0.0292(3) 0.32605(8) 0.0593(6) Uani 0.371(18) 1 d . . P A 2
C3 C 0.32958(15) -0.0777(4) 0.40145(12) 0.0833(8) Uani 1 1 d . . . . .
H3 H 0.284067 -0.049309 0.423651 0.100 Uiso 1 1 calc R U . . .
C2 C 0.39646(13) 0.0252(4) 0.40473(10) 0.0709(6) Uani 1 1 d . . . . .
H2 H 0.396805 0.123187 0.428700 0.085 Uiso 1 1 calc R U . A 1
C4 C 0.32706(17) -0.2262(4) 0.36538(12) 0.0909(9) Uani 1 1 d . . . . .
H4 H 0.280639 -0.295598 0.364477 0.109 Uiso 1 1 calc R U . . .
C5 C 0.39238(17) -0.2683(4) 0.33187(12) 0.0819(8) Uani 1 1 d . . . . .
H5 H 0.390599 -0.365642 0.307654 0.098 Uiso 1 1 calc R U . . .
C6 C 0.46233(14) -0.1644(3) 0.33396(9) 0.0641(6) Uani 1 1 d . . . . .
C7 C 0.53743(13) -0.1708(3) 0.30488(9) 0.0625(6) Uani 1 1 d . . . . .
C9 C 0.66484(13) -0.0100(3) 0.30641(10) 0.0684(6) Uani 1 1 d . . . . .
H9 H 0.697220 0.079803 0.320831 0.082 Uiso 1 1 calc R U . A 1
C10 C 0.69504(16) -0.1226(4) 0.26640(11) 0.0784(7) Uani 1 1 d . . . . .
H10 H 0.748442 -0.109442 0.253669 0.094 Uiso 1 1 calc R U . . .
C11 C 0.64726(18) -0.2594(4) 0.24360(12) 0.0828(8) Uani 1 1 d . . . . .
H11 H 0.668818 -0.333388 0.215356 0.099 Uiso 1 1 calc R U . . .
C12 C 0.57020(17) -0.2834(3) 0.26267(10) 0.0747(7) Uani 1 1 d . . . . .
H12 H 0.538950 -0.374357 0.247821 0.090 Uiso 1 1 calc R U . . .
C13 C 0.53943(12) 0.0651(3) 0.36695(9) 0.0588(5) Uani 1 1 d . . . . .
C14 C 0.56547(12) 0.2222(3) 0.39826(9) 0.0574(5) Uani 1 1 d . . . . .
C15 C 0.59862(13) 0.3623(3) 0.36828(9) 0.0642(6) Uani 1 1 d . . . . .
H15 H 0.601629 0.357717 0.327755 0.077 Uiso 1 1 calc R U . . .
C16 C 0.62745(13) 0.5092(3) 0.39708(10) 0.0638(6) Uani 1 1 d . . . . .
H16 H 0.650032 0.601063 0.376050 0.077 Uiso 1 1 calc R U . . .
C17 C 0.62240(12) 0.5180(3) 0.45700(9) 0.0584(5) Uani 1 1 d . . . . .
C18 C 0.58703(13) 0.3822(3) 0.48802(9) 0.0637(6) Uani 1 1 d . . . . .
H18 H 0.582040 0.389468 0.528398 0.076 Uiso 1 1 calc R U . . .
C19 C 0.55931(13) 0.2365(3) 0.45886(9) 0.0628(6) Uani 1 1 d . . . . .
H19 H 0.535979 0.145781 0.480015 0.075 Uiso 1 1 calc R U . . .
O20 O 0.65099(10) 0.6551(2) 0.48971(7) 0.0755(5) Uani 1 1 d . . . . .
C21 C 0.69499(18) 0.7871(4) 0.46002(13) 0.0911(8) Uani 1 1 d . . . . .
H21A H 0.716940 0.867985 0.487891 0.137 Uiso 1 1 calc R U . . .
H21B H 0.659231 0.847729 0.433801 0.137 Uiso 1 1 calc R U . . .
H21C H 0.738617 0.734963 0.438251 0.137 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 C13 1.385(3) . ?
N1 C2 1.396(3) . ?
N1 C6 1.415(3) . ?
C8 C13 1.395(3) . ?
C8 C9 1.402(3) . ?
C8 C7 1.418(3) . ?
C1 C13 1.385(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.415(3) . ?
N8 C13 1.395(3) . ?
N8 C9 1.402(3) . ?
N8 C7 1.418(3) . ?
C3 C2 1.354(4) . ?
C3 C4 1.407(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 C5 1.358(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(3) . ?
C7 C12 1.403(3) . ?
C9 C10 1.353(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.410(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.352(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.464(3) . ?
C14 C15 1.386(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 O20 1.373(2) . ?
C17 C18 1.387(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O20 C21 1.417(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C13 N1 C2 130.2(2) . . ?
C13 N1 C6 110.08(18) . . ?
C2 N1 C6 119.68(19) . . ?
C13 C8 C9 131.3(2) . . ?
C13 C8 C7 109.65(18) . . ?
C9 C8 C7 118.9(2) . . ?
C13 C1 C2 130.2(2) . . ?
C13 C1 C6 110.08(18) . . ?
C2 C1 C6 119.68(19) . . ?
C13 N8 C9 131.3(2) . . ?
C13 N8 C7 109.65(18) . . ?
C9 N8 C7 118.9(2) . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C2 N1 119.0(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
N1 C2 H2 120.5 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 133.3(2) . . ?
C5 C6 C1 119.7(2) . . ?
C7 C6 C1 106.94(18) . . ?
C5 C6 N1 119.7(2) . . ?
C7 C6 N1 106.94(18) . . ?
C12 C7 C6 133.3(2) . . ?
C12 C7 C8 119.8(2) . . ?
C6 C7 C8 106.87(19) . . ?
C12 C7 N8 119.8(2) . . ?
C6 C7 N8 106.87(19) . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 N8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 121.4(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C1 C13 N8 106.47(19) . . ?
N1 C13 C8 106.47(19) . . ?
C1 C13 C14 126.75(19) . . ?
N1 C13 C14 126.75(19) . . ?
N8 C13 C14 126.78(19) . . ?
C8 C13 C14 126.78(19) . . ?
C15 C14 C19 117.4(2) . . ?
C15 C14 C13 120.56(18) . . ?
C19 C14 C13 122.03(19) . . ?
C14 C15 C16 121.8(2) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
O20 C17 C16 124.1(2) . . ?
O20 C17 C18 115.94(19) . . ?
C16 C17 C18 120.0(2) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 121.5(2) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C17 O20 C21 117.30(19) . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.125
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036




_chemical_properties_physical    Air-sensitive,Oxygen-sensitive
