# 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_nh2hydro
_database_code_depnum_ccdc_archive 'CCDC 2371431'
loop_
_audit_author_name
_audit_author_address
NHH
;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         'C9 H9 N O'
_chemical_formula_sum            'C9 H9 N O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         147.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   19.9102(4)
_cell_length_b                   19.9102(4)
_cell_length_c                   7.2407(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2870.33(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2171
_cell_measurement_theta_min      3.6130
_cell_measurement_theta_max      28.0760
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.42
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_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  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10044
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.894
_diffrn_reflns_theta_max         29.047
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1787
_reflns_number_gt                1381
_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       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0462P)²+1.6730P] 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         1787
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
O O 0.15889(5) 0.53419(5) 0.12912(14) 0.0309(3) Uani 1 1 d . . . . .
N N 0.16575(6) 0.46770(7) -0.23486(18) 0.0278(3) Uani 1 1 d . . . . .
H0A H 0.1835(10) 0.4569(10) -0.346(3) 0.052(6) Uiso 1 1 d . . . . .
H0B H 0.1830(9) 0.5043(10) -0.170(3) 0.043(5) Uiso 1 1 d . . . . .
C1 C 0.10997(7) 0.49680(7) 0.14561(19) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.06333(8) 0.49461(7) 0.31102(19) 0.0269(3) Uani 1 1 d . . . . .
H2A H 0.0395 0.5380 0.3253 0.032 Uiso 1 1 calc R U . . .
H2B H 0.0890 0.4854 0.4254 0.032 Uiso 1 1 calc R U . . .
C3 C 0.01305(7) 0.43766(7) 0.27281(19) 0.0266(3) Uani 1 1 d . . . . .
H3A H 0.0176 0.4015 0.3657 0.032 Uiso 1 1 calc R U . . .
H3B H -0.0337 0.4547 0.2752 0.032 Uiso 1 1 calc R U . . .
C4 C 0.03121(7) 0.41241(7) 0.08278(18) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.00094(7) 0.36161(7) -0.0170(2) 0.0271(3) Uani 1 1 d . . . . .
H5A H -0.0373 0.3385 0.0291 0.033 Uiso 1 1 calc R U . . .
C6 C 0.02873(7) 0.34567(7) -0.1884(2) 0.0283(3) Uani 1 1 d . . . . .
H6A H 0.0092 0.3103 -0.2581 0.034 Uiso 1 1 calc R U . . .
C7 C 0.08349(7) 0.37918(7) -0.2613(2) 0.0249(3) Uani 1 1 d . . . . .
H7A H 0.1007 0.3664 -0.3784 0.030 Uiso 1 1 calc R U . . .
C8 C 0.11386(7) 0.43203(7) -0.16353(18) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.08674(6) 0.44684(6) 0.01251(18) 0.0194(3) 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
O C1 1.2316(17) . ?
N C8 1.3559(18) . ?
N H0A 0.90(2) . ?
N H0B 0.93(2) . ?
C1 C9 1.4602(19) . ?
C1 C2 1.5161(19) . ?
C2 C3 1.538(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5089(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.382(2) . ?
C4 C9 1.3967(18) . ?
C5 C6 1.395(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.4049(19) . ?
C7 H7A 0.9500 . ?
C8 C9 1.4154(18) . ?

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
C8 N H0A 120.8(12) . . ?
C8 N H0B 119.8(11) . . ?
H0A N H0B 119.4(17) . . ?
O C1 C9 126.75(13) . . ?
O C1 C2 125.33(13) . . ?
C9 C1 C2 107.92(12) . . ?
C1 C2 C3 106.13(11) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 104.69(11) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C9 120.93(13) . . ?
C5 C4 C3 128.05(13) . . ?
C9 C4 C3 111.01(12) . . ?
C4 C5 C6 117.30(13) . . ?
C4 C5 H5A 121.3 . . ?
C6 C5 H5A 121.3 . . ?
C7 C6 C5 122.84(13) . . ?
C7 C6 H6A 118.6 . . ?
C5 C6 H6A 118.6 . . ?
C6 C7 C8 120.57(13) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
N C8 C9 121.65(13) . . ?
N C8 C7 121.89(13) . . ?
C9 C8 C7 116.45(12) . . ?
C4 C9 C8 121.86(12) . . ?
C4 C9 C1 110.16(12) . . ?
C8 C9 C1 127.98(12) . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053


_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_h-m   I4(1)/a
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

