# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2293832'
loop_
_audit_author_name
_audit_author_address
'S. S. Bhattacharya'
;SAIF, IIT Madras
India
;
_audit_update_record             
;
2023-09-08 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O '

_chemical_formula_sum            'C15 H18 N2 O'
_chemical_formula_weight         242.31

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.7284(5)
_cell_length_b                   7.7936(5)
_cell_length_c                   11.5229(8)
_cell_angle_alpha                77.928(2)
_cell_angle_beta                 71.564(2)
_cell_angle_gamma                85.819(2)
_cell_volume                     643.85(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)

_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.55
_exptl_crystal_description       PLATE
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5029
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_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  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27882
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.778
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             2267
_reflns_number_gt                1779
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'

_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_refine_special_details          
;
Part of the molecule is disordered over two positions. The atoms
C12, C13 and N1 are occupied at two sites with a ratio of 63:37.
The positions were located from electron density peaks and refined
using appropriate restraints. The 1,2 distances between disordered 
atoms were refined to same values using SADI instruction.
The atoms in the disordered group were restrained with an effective 
standard deviation of 0.02 Å2 to have the same Uij components 
using SIMU instruction.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+0.2797P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2267
_refine_ls_number_parameters     197
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1676
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.004
_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
C1 C 0.4508(3) 0.5207(3) 0.8410(2) 0.0584(6) Uani 1 1 d . . . . .
H1 H 0.433627 0.624269 0.871358 0.070 Uiso 1 1 calc R U . . .
C2 C 0.3794(3) 0.3657(3) 0.9200(2) 0.0658(6) Uani 1 1 d . . . . .
H2 H 0.315647 0.365758 1.003288 0.079 Uiso 1 1 calc R U . . .
C3 C 0.4018(3) 0.2121(3) 0.8768(2) 0.0633(6) Uani 1 1 d . . . . .
H3 H 0.355307 0.107907 0.930660 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4934(3) 0.2132(3) 0.7534(2) 0.0622(6) Uani 1 1 d . . . . .
H4 H 0.507147 0.109727 0.723149 0.075 Uiso 1 1 calc R U . . .
C5 C 0.5652(3) 0.3674(3) 0.6738(2) 0.0554(6) Uani 1 1 d . . . . .
H5 H 0.626289 0.366776 0.590232 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5476(3) 0.5231(2) 0.71674(18) 0.0475(5) Uani 1 1 d . . . . .
C7 C 0.6259(3) 0.6970(3) 0.6371(2) 0.0531(5) Uani 1 1 d . . . . .
C8 C 0.7431(3) 0.6996(3) 0.51416(19) 0.0517(5) Uani 1 1 d . . . . .
H8 H 0.772035 0.591981 0.489744 0.062 Uiso 1 1 calc R U . . .
C9 C 0.8185(3) 0.8471(3) 0.42692(19) 0.0515(5) Uani 1 1 d . . . . .
C10 C 0.7801(3) 1.0293(3) 0.4535(2) 0.0651(6) Uani 1 1 d . . . . .
H10A H 0.817640 1.034620 0.525403 0.078 Uiso 1 1 calc R U . . .
H10B H 0.649265 1.048825 0.476384 0.078 Uiso 1 1 calc R U . . .
C11 C 0.8710(5) 1.1788(3) 0.3485(3) 0.0904(9) Uani 1 1 d D . . . .
H11A H 0.778311 1.236546 0.313261 0.108 Uiso 0.372(9) 1 calc R U P A 1
H11B H 0.911388 1.263299 0.385263 0.108 Uiso 0.372(9) 1 calc R U P A 1
H11C H 0.789747 1.279808 0.352269 0.108 Uiso 0.628(9) 1 calc R U P A 2
H11D H 0.981133 1.210979 0.361851 0.108 Uiso 0.628(9) 1 calc R U P A 2
C14 C 1.0933(4) 0.7235(4) 0.1353(2) 0.0778(8) Uani 1 1 d D . . . .
H14A H 1.202857 0.651636 0.118185 0.093 Uiso 1 1 calc R U . A 1
H14B H 1.028424 0.714658 0.077230 0.093 Uiso 1 1 calc R U . A 1
C15 C 0.9721(3) 0.6661(3) 0.2703(2) 0.0638(6) Uani 1 1 d . . . . .
H15A H 0.862768 0.608670 0.273897 0.077 Uiso 1 1 calc R U . . .
H15B H 1.037177 0.587168 0.319442 0.077 Uiso 1 1 calc R U . . .
N2 N 0.9281(3) 0.8316(2) 0.31371(16) 0.0603(5) Uani 1 1 d . . . . .
O1 O 0.5834(3) 0.8275(2) 0.68541(17) 0.0927(7) Uani 1 1 d . . . . .
C12 C 1.0153(15) 1.1424(10) 0.2524(8) 0.082(3) Uani 0.372(9) 1 d D U P A 1
H12A H 1.121911 1.118564 0.280630 0.098 Uiso 0.372(9) 1 calc R U P A 1
H12B H 1.040935 1.244729 0.185384 0.098 Uiso 0.372(9) 1 calc R U P A 1
N1 N 1.1402(13) 0.9134(10) 0.1250(8) 0.079(2) Uani 0.372(9) 1 d D U P A 1
H1A H 1.230(8) 0.910(11) 0.155(7) 0.095 Uiso 0.372(9) 1 d D U P A 1
C13 C 0.983(2) 0.990(2) 0.2032(18) 0.064(4) Uani 0.372(9) 1 d D U P A 1
H13 H 0.887486 1.016676 0.162747 0.076 Uiso 0.372(9) 1 calc R U P A 1
C12' C 0.9200(8) 1.1377(6) 0.2202(4) 0.0717(15) Uani 0.628(9) 1 d D U P A 2
H12C H 0.809313 1.126218 0.200016 0.086 Uiso 0.628(9) 1 calc R U P A 2
H12D H 0.989690 1.233958 0.159748 0.086 Uiso 0.628(9) 1 calc R U P A 2
N1' N 1.0583(9) 0.9047(6) 0.0995(4) 0.0716(13) Uani 0.628(9) 1 d D U P A 2
H1B H 0.956(4) 0.924(6) 0.082(4) 0.086 Uiso 0.628(9) 1 d D U P A 2
C13' C 1.0292(14) 0.9723(12) 0.2117(10) 0.061(2) Uani 0.628(9) 1 d D U P A 2
H13' H 1.147402 0.988891 0.222238 0.074 Uiso 0.628(9) 1 calc R U P A 2


_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
C1 C2 1.383(3) . ?
C1 C6 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(3) . ?
C7 O1 1.234(2) . ?
C7 C8 1.416(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.336(3) . ?
C9 C10 1.504(3) . ?
C10 C11 1.519(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.361(8) . ?
C11 C12' 1.502(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C14 N1' 1.417(5) . ?
C14 N1 1.521(9) . ?
C14 C15 1.532(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N2 1.459(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N2 C13' 1.483(12) . ?
N2 C13 1.55(2) . ?
C12 C13 1.488(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N1 C13 1.439(13) . ?
N1 H1A 0.86(2) . ?
C13 H13 0.9800 . ?
C12' C13' 1.492(8) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
N1' C13' 1.443(9) . ?
N1' H1B 0.868(19) . ?
C13' H13' 0.9800 . ?

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 C1 C6 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.07(19) . . ?
C5 C6 C7 124.56(18) . . ?
C1 C6 C7 117.36(18) . . ?
O1 C7 C8 124.53(19) . . ?
O1 C7 C6 116.89(19) . . ?
C8 C7 C6 118.58(18) . . ?
C9 C8 C7 126.24(19) . . ?
C9 C8 H8 116.9 . . ?
C7 C8 H8 116.9 . . ?
N2 C9 C8 120.38(19) . . ?
N2 C9 C10 117.30(18) . . ?
C8 C9 C10 122.31(19) . . ?
C9 C10 C11 116.5(2) . . ?
C9 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
C9 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C12 C11 C10 119.0(4) . . ?
C12' C11 C10 114.5(3) . . ?
C12 C11 H11A 107.6 . . ?
C10 C11 H11A 107.6 . . ?
C12 C11 H11B 107.6 . . ?
C10 C11 H11B 107.6 . . ?
H11A C11 H11B 107.0 . . ?
C12' C11 H11C 108.6 . . ?
C10 C11 H11C 108.6 . . ?
C12' C11 H11D 108.6 . . ?
C10 C11 H11D 108.6 . . ?
H11C C11 H11D 107.6 . . ?
N1' C14 C15 106.6(3) . . ?
N1 C14 C15 104.8(4) . . ?
N1 C14 H14A 110.8 . . ?
C15 C14 H14A 110.8 . . ?
N1 C14 H14B 110.8 . . ?
C15 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
N2 C15 C14 102.90(18) . . ?
N2 C15 H15A 111.2 . . ?
C14 C15 H15A 111.2 . . ?
N2 C15 H15B 111.2 . . ?
C14 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C9 N2 C15 124.45(17) . . ?
C9 N2 C13' 127.9(3) . . ?
C15 N2 C13' 107.6(3) . . ?
C9 N2 C13 122.9(5) . . ?
C15 N2 C13 110.9(5) . . ?
C11 C12 C13 113.0(8) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 N1 C14 106.7(8) . . ?
C13 N1 H1A 109(6) . . ?
C14 N1 H1A 106(5) . . ?
N1 C13 C12 116.9(13) . . ?
N1 C13 N2 98.7(11) . . ?
C12 C13 N2 108.1(12) . . ?
N1 C13 H13 110.8 . . ?
C12 C13 H13 110.8 . . ?
N2 C13 H13 110.8 . . ?
C13' C12' C11 111.5(5) . . ?
C13' C12' H12C 109.3 . . ?
C11 C12' H12C 109.3 . . ?
C13' C12' H12D 109.3 . . ?
C11 C12' H12D 109.3 . . ?
H12C C12' H12D 108.0 . . ?
C14 N1' C13' 104.0(5) . . ?
C14 N1' H1B 113(3) . . ?
C13' N1' H1B 105(3) . . ?
N1' C13' N2 104.5(6) . . ?
N1' C13' C12' 116.2(8) . . ?
N2 C13' C12' 108.1(7) . . ?
N1' C13' H13' 109.3 . . ?
N2 C13' H13' 109.3 . . ?
C12' C13' H13' 109.3 . . ?

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
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 -2.0(3) . . . . ?
C4 C5 C6 C7 178.4(2) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
C2 C1 C6 C7 -178.3(2) . . . . ?
C5 C6 C7 O1 172.9(2) . . . . ?
C1 C6 C7 O1 -6.6(3) . . . . ?
C5 C6 C7 C8 -7.7(3) . . . . ?
C1 C6 C7 C8 172.7(2) . . . . ?
O1 C7 C8 C9 -4.3(4) . . . . ?
C6 C7 C8 C9 176.40(19) . . . . ?
C7 C8 C9 N2 179.7(2) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
N2 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 -179.4(2) . . . . ?
C9 C10 C11 C12 -17.4(7) . . . . ?
C9 C10 C11 C12' 24.4(5) . . . . ?
N1' C14 C15 N2 -19.8(4) . . . . ?
N1 C14 C15 N2 12.3(5) . . . . ?
C8 C9 N2 C15 2.4(3) . . . . ?
C10 C9 N2 C15 -176.7(2) . . . . ?
C8 C9 N2 C13' -176.1(5) . . . . ?
C10 C9 N2 C13' 4.7(6) . . . . ?
C8 C9 N2 C13 166.3(7) . . . . ?
C10 C9 N2 C13 -12.9(8) . . . . ?
C14 C15 N2 C9 177.6(2) . . . . ?
C14 C15 N2 C13' -3.6(5) . . . . ?
C14 C15 N2 C13 12.1(7) . . . . ?
C10 C11 C12 C13 46.5(15) . . . . ?
C15 C14 N1 C13 -34.6(12) . . . . ?
C14 N1 C13 C12 154.8(12) . . . . ?
C14 N1 C13 N2 39.4(12) . . . . ?
C11 C12 C13 N1 -164.6(11) . . . . ?
C11 C12 C13 N2 -54.5(14) . . . . ?
C9 N2 C13 N1 161.6(7) . . . . ?
C15 N2 C13 N1 -32.6(11) . . . . ?
C9 N2 C13 C12 39.5(13) . . . . ?
C15 N2 C13 C12 -154.7(8) . . . . ?
C10 C11 C12' C13' -52.4(8) . . . . ?
C15 C14 N1' C13' 35.9(7) . . . . ?
C14 N1' C13' N2 -37.6(8) . . . . ?
C14 N1' C13' C12' -156.7(7) . . . . ?
C9 N2 C13' N1' -156.0(4) . . . . ?
C15 N2 C13' N1' 25.2(8) . . . . ?
C9 N2 C13' C12' -31.7(9) . . . . ?
C15 N2 C13' C12' 149.6(6) . . . . ?
C11 C12' C13' N1' 170.1(6) . . . . ?
C11 C12' C13' N2 53.1(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12A O1 0.97 2.51 3.431(13) 158.9 2_776 yes
N1' H1B N1' 0.868(19) 2.27(4) 2.823(11) 122(4) 2_775 yes

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.035



