# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_nhac
_database_code_depnum_ccdc_archive 'CCDC 2371433'
loop_
_audit_author_name
_audit_author_address
NHA
;Feng Chia University
Taiwan
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H11 N O2'
_chemical_formula_sum            'C11 H11 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         189.21

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.2154(4)
_cell_length_b                   9.6795(6)
_cell_length_c                   13.3482(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.728(2)
_cell_angle_gamma                90
_cell_volume                     923.79(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5087
_cell_measurement_theta_min      3.080
_cell_measurement_theta_max      26.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8516
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13495
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.051
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1885
_reflns_number_gt                1526
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0806P)²+1.1015P] 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         1885
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.1868(2) 0.94235(16) 0.30284(11) 0.0264(4) Uani 1 1 d . . . . .
O2 O 0.1335(3) 1.31378(17) 0.56775(12) 0.0316(5) Uani 1 1 d . . . . .
N N 0.1718(3) 1.13795(18) 0.45914(14) 0.0190(4) Uani 1 1 d . . . . .
H0A H 0.161(4) 1.115(3) 0.395(2) 0.037(8) Uiso 1 1 d . . . . .
C1 C 0.2775(3) 0.9052(2) 0.48100(16) 0.0184(5) Uani 1 1 d . . . . .
C2 C 0.2501(3) 0.8680(2) 0.37331(16) 0.0206(5) Uani 1 1 d . . . . .
C3 C 0.3134(4) 0.7195(2) 0.36487(19) 0.0296(6) Uani 1 1 d . . . . .
H3A H 0.4198 0.7144 0.3253 0.036 Uiso 1 1 calc R U . . .
H3B H 0.2100 0.6620 0.3311 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3727(3) 0.6692(2) 0.47306(19) 0.0269(5) Uani 1 1 d . . . . .
H4A H 0.2932 0.5913 0.4895 0.032 Uiso 1 1 calc R U . . .
H4B H 0.5049 0.6387 0.4823 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3472(3) 0.7926(2) 0.53868(17) 0.0225(5) Uani 1 1 d . . . . .
C6 C 0.3801(3) 0.8029(3) 0.64310(18) 0.0290(6) Uani 1 1 d . . . . .
H6A H 0.4301 0.7274 0.6834 0.035 Uiso 1 1 calc R U . . .
C7 C 0.3379(3) 0.9268(3) 0.68689(17) 0.0292(6) Uani 1 1 d . . . . .
H7A H 0.3570 0.9342 0.7585 0.035 Uiso 1 1 calc R U . . .
C8 C 0.2684(3) 1.0411(2) 0.63003(17) 0.0235(5) Uani 1 1 d . . . . .
H8A H 0.2417 1.1246 0.6627 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2385(3) 1.0316(2) 0.52518(16) 0.0176(5) Uani 1 1 d . . . . .
C10 C 0.1249(3) 1.2702(2) 0.48154(16) 0.0204(5) Uani 1 1 d . . . . .
C11 C 0.0674(3) 1.3578(2) 0.39013(17) 0.0251(5) Uani 1 1 d . . . . .
H11A H 0.0703 1.3022 0.3290 0.038 Uiso 1 1 calc R U . . .
H11B H -0.0596 1.3927 0.3919 0.038 Uiso 1 1 calc R U . . .
H11C H 0.1540 1.4357 0.3897 0.038 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 C2 1.223(3) . ?
O2 C10 1.220(3) . ?
N C10 1.367(3) . ?
N C9 1.398(3) . ?
N H0A 0.87(3) . ?
C1 C9 1.403(3) . ?
C1 C5 1.389(3) . ?
C1 C2 1.469(3) . ?
C2 C3 1.517(3) . ?
C3 C4 1.529(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.507(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.386(3) . ?
C6 C7 1.385(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.397(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8A 0.9500 . ?
C10 C11 1.498(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C10 N C9 128.73(18) . . ?
C10 N H0A 117(2) . . ?
C9 N H0A 114(2) . . ?
C9 C1 C5 121.96(19) . . ?
C9 C1 C2 128.08(19) . . ?
C5 C1 C2 109.94(19) . . ?
O1 C2 C1 126.5(2) . . ?
O1 C2 C3 125.8(2) . . ?
C1 C2 C3 107.61(19) . . ?
C2 C3 C4 106.27(19) . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
C4 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C3 104.84(18) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C6 C5 C1 120.1(2) . . ?
C6 C5 C4 128.6(2) . . ?
C1 C5 C4 111.3(2) . . ?
C5 C6 C7 118.0(2) . . ?
C5 C6 H6A 121.0 . . ?
C7 C6 H6A 121.0 . . ?
C6 C7 C8 122.7(2) . . ?
C6 C7 H7A 118.7 . . ?
C8 C7 H7A 118.7 . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C1 C9 C8 117.9(2) . . ?
C1 C9 N 116.65(18) . . ?
C8 C9 N 125.4(2) . . ?
O2 C10 N 123.2(2) . . ?
O2 C10 C11 123.1(2) . . ?
N C10 C11 113.66(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C9 C1 C2 O1 -0.3(4) . . . . ?
C5 C1 C2 O1 178.3(2) . . . . ?
C9 C1 C2 C3 -179.9(2) . . . . ?
C5 C1 C2 C3 -1.4(2) . . . . ?
O1 C2 C3 C4 -177.6(2) . . . . ?
C1 C2 C3 C4 2.0(2) . . . . ?
C2 C3 C4 C5 -1.9(2) . . . . ?
C9 C1 C5 C6 0.1(3) . . . . ?
C2 C1 C5 C6 -178.6(2) . . . . ?
C9 C1 C5 C4 178.79(19) . . . . ?
C2 C1 C5 C4 0.1(2) . . . . ?
C3 C4 C5 C6 179.7(2) . . . . ?
C3 C4 C5 C1 1.2(2) . . . . ?
C1 C5 C6 C7 1.3(3) . . . . ?
C4 C5 C6 C7 -177.2(2) . . . . ?
C5 C6 C7 C8 -1.5(4) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C5 C1 C9 C8 -1.2(3) . . . . ?
C2 C1 C9 C8 177.2(2) . . . . ?
C5 C1 C9 N 178.99(18) . . . . ?
C2 C1 C9 N -2.6(3) . . . . ?
C7 C8 C9 C1 1.0(3) . . . . ?
C7 C8 C9 N -179.3(2) . . . . ?
C10 N C9 C1 -179.36(19) . . . . ?
C10 N C9 C8 0.9(3) . . . . ?
C9 N C10 O2 -1.3(4) . . . . ?
C9 N C10 C11 177.0(2) . . . . ?

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
N H0A O1 0.87(3) 2.10(3) 2.830(2) 140(3) .
C8 H8A O2 0.95 2.30 2.896(3) 119.9 .

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.065


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/n
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

