# 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. 
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data_dt2001
_database_code_depnum_ccdc_archive 'CCDC 2356146'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2024-05-17 deposited with the CCDC.	2024-09-16 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         'C9 H9 N O2'
_chemical_formula_sum            'C9 H9 N O2'
_chemical_formula_weight         163.17

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.3771(2)
_cell_length_b                   5.7567(2)
_cell_length_c                   12.4675(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.824(3)
_cell_angle_gamma                90
_cell_volume                     377.74(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2671
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      70.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    0.845
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8311
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec micro-focus'
_diffrn_source_monochromator     'MONTEL Multi-layer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            5982
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.622
_diffrn_reflns_theta_max         70.425
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1419
_reflns_number_gt                1306
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.976

_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 APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0547P)²+0.0269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 
;
 Flack x determined using 530 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1419
_refine_ls_number_parameters     117
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.1350(4) 0.2671(4) 0.53624(19) 0.0256(5) Uani 1 1 d . . . . .
O2 O 0.5056(4) 0.0830(4) 0.59513(18) 0.0222(5) Uani 1 1 d . . . . .
N1 N 0.2973(5) 0.6747(4) 0.6205(2) 0.0191(6) Uani 1 1 d . . . . .
H1NA H 0.170(7) 0.634(7) 0.565(3) 0.018(8) Uiso 1 1 d . . . . .
H1NB H 0.371(8) 0.798(8) 0.600(3) 0.028(10) Uiso 1 1 d . . . . .
C2 C 0.4813(5) 0.4733(5) 0.6449(2) 0.0193(6) Uani 1 1 d . . . . .
H2 H 0.642167 0.511356 0.620216 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5362(6) 0.4410(5) 0.7708(3) 0.0233(7) Uani 1 1 d . . . . .
H3A H 0.509817 0.277521 0.790479 0.028 Uiso 1 1 calc R U . . .
H3B H 0.712605 0.487069 0.803936 0.028 Uiso 1 1 calc R U . . .
C3A C 0.3474(5) 0.5991(5) 0.8084(2) 0.0213(6) Uani 1 1 d . . . . .
C4 C 0.2997(6) 0.6315(5) 0.9128(3) 0.0255(7) Uani 1 1 d . . . . .
H4 H 0.390361 0.546049 0.973542 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1144(6) 0.7936(6) 0.9257(3) 0.0267(7) Uani 1 1 d . . . . .
H5 H 0.078912 0.818687 0.996406 0.032 Uiso 1 1 calc R U . . .
C6 C -0.0177(6) 0.9178(5) 0.8376(3) 0.0267(7) Uani 1 1 d . . . . .
H6 H -0.142740 1.026674 0.848699 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0288(6) 0.8864(5) 0.7327(3) 0.0230(7) Uani 1 1 d . . . . .
H7 H -0.061548 0.970722 0.671488 0.028 Uiso 1 1 calc R U . . .
C7A C 0.2137(5) 0.7259(5) 0.7228(2) 0.0198(6) Uani 1 1 d . . . . .
C8 C 0.3592(5) 0.2555(5) 0.5854(2) 0.0192(6) Uani 1 1 d . . . . .


_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 C8 1.237(4) . ?
O2 C8 1.258(4) . ?
N1 C7A 1.466(4) . ?
N1 C2 1.514(4) . ?
N1 H1NA 0.90(4) . ?
N1 H1NB 0.88(5) . ?
C2 C8 1.534(4) . ?
C2 C3 1.548(4) . ?
C2 H2 1.0000 . ?
C3 C3A 1.507(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C7A 1.369(4) . ?
C3A C4 1.390(5) . ?
C4 C5 1.399(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(5) . ?
C6 H6 0.9500 . ?
C7 C7A 1.382(4) . ?
C7 H7 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
C7A N1 C2 106.5(2) . . ?
C7A N1 H1NA 114(2) . . ?
C2 N1 H1NA 109(2) . . ?
C7A N1 H1NB 109(3) . . ?
C2 N1 H1NB 111(3) . . ?
H1NA N1 H1NB 108(4) . . ?
N1 C2 C8 109.4(2) . . ?
N1 C2 C3 106.0(2) . . ?
C8 C2 C3 111.5(2) . . ?
N1 C2 H2 110.0 . . ?
C8 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
C3A C3 C2 104.0(2) . . ?
C3A C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C3A C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C7A C3A C4 119.4(3) . . ?
C7A C3A C3 111.1(3) . . ?
C4 C3A C3 129.6(3) . . ?
C3A C4 C5 118.1(3) . . ?
C3A C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C7A C7 C6 116.2(3) . . ?
C7A C7 H7 121.9 . . ?
C6 C7 H7 121.9 . . ?
C3A C7A C7 124.0(3) . . ?
C3A C7A N1 111.4(3) . . ?
C7 C7A N1 124.6(3) . . ?
O1 C8 O2 128.1(3) . . ?
O1 C8 C2 118.2(3) . . ?
O2 C8 C2 113.7(2) . . ?

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
C7A N1 C2 C8 110.3(2) . . . . ?
C7A N1 C2 C3 -10.0(3) . . . . ?
N1 C2 C3 C3A 9.1(3) . . . . ?
C8 C2 C3 C3A -109.8(3) . . . . ?
C2 C3 C3A C7A -5.0(3) . . . . ?
C2 C3 C3A C4 176.1(3) . . . . ?
C7A C3A C4 C5 0.2(4) . . . . ?
C3 C3A C4 C5 179.0(3) . . . . ?
C3A C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C7A -0.2(5) . . . . ?
C4 C3A C7A C7 -0.5(5) . . . . ?
C3 C3A C7A C7 -179.6(3) . . . . ?
C4 C3A C7A N1 177.7(3) . . . . ?
C3 C3A C7A N1 -1.3(3) . . . . ?
C6 C7 C7A C3A 0.5(4) . . . . ?
C6 C7 C7A N1 -177.5(3) . . . . ?
C2 N1 C7A C3A 7.3(3) . . . . ?
C2 N1 C7A C7 -174.5(3) . . . . ?
N1 C2 C8 O1 -5.5(4) . . . . ?
C3 C2 C8 O1 111.4(3) . . . . ?
N1 C2 C8 O2 175.5(2) . . . . ?
C3 C2 C8 O2 -67.6(3) . . . . ?

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
N1 H1NA O1 0.90(4) 2.14(4) 2.645(3) 114(3) . yes
N1 H1NA O1 0.90(4) 2.00(4) 2.765(3) 141(3) 2_556 yes
N1 H1NB O2 0.88(5) 1.80(5) 2.650(3) 163(4) 1_565 yes

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.047

