# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_621-01
_database_code_depnum_ccdc_archive 'CCDC 2390753'
loop_
_audit_author_name
_audit_author_address
'Chang-Qing Qin'
;School of Chemistry and Chemical Engineering Guangzhou University
China
;
_audit_update_record             
;
2024-10-14 deposited with the CCDC.	2024-12-04 downloaded from the CCDC.
;
_audit_creation_date             2022-06-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O'
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.25
_chemical_melting_point          ?
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'

_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.
;
_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'
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                   9.1158(10)
_cell_length_b                   9.8374(13)
_cell_length_c                   25.365(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2274.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3294
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      70.0740
_cell_measurement_theta_min      3.4330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7979
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.190
_diffrn_reflns_theta_min         3.485
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00  89.00   0.50    0.50    --   42.30  57.00-120.00   68
  2  ω     81.00 112.00   0.50    0.50    --   42.30  77.00 150.00   62
  3  ω     94.00 132.00   0.50    0.50    --   42.30  57.00-120.00   76
  4  ω     24.00  50.00   0.50    0.50    --   42.30  57.00-120.00   52
  5  ω     80.00 132.00   0.50    0.50    --   42.30  77.00 -90.00  104
  6  ω     98.00 131.00   0.50    0.50    --   42.30  77.00   0.00   66
  7  ω     69.00 128.00   0.50    0.50    --  101.00 -63.00  60.00  118
  8  ω    139.00 175.00   0.50    0.50    --  101.00  82.00 120.00   72
  9  ω    118.00 177.00   0.50    0.50    --  101.00  82.00-120.00  118
 10  ω     40.00  66.00   0.50    0.50    --  101.00 -63.00  60.00   52
 11  ω     71.00 130.00   0.50    0.50    --  101.00  50.00 -60.00  118
 12  ω     90.00 122.00   0.50    0.50    --  101.00  82.00 120.00   64
 13  ω     12.00 140.00   0.50    0.50    --  101.00 -82.00  60.00  256
 14  ω    -23.00  80.00   0.50    0.50    --   42.10 -82.00 -30.00  206
 15  ω     -6.00  58.00   0.50    0.50    --   42.10 -57.00 -30.00  128
 16  ω    -11.00  49.00   0.50    0.50    --   42.10 -82.00 120.00  120
 17  ω     21.00  67.00   0.50    0.50    --   42.10 -57.00  90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0761053000
_diffrn_orient_matrix_UB_12      -0.1034195000
_diffrn_orient_matrix_UB_13      0.0362206000
_diffrn_orient_matrix_UB_21      0.1069933000
_diffrn_orient_matrix_UB_22      -0.0368388000
_diffrn_orient_matrix_UB_23      -0.0449241000
_diffrn_orient_matrix_UB_31      0.1062973000
_diffrn_orient_matrix_UB_32      0.1114364000
_diffrn_orient_matrix_UB_33      0.0192302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1400
_reflns_number_total             2090
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0771
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1718P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2090
_refine_ls_wR_factor_ref         0.2623
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C9(H9), C10(H10), C3(H3), C2(H2), C14(H14), C13(H13),
 C1(H1A)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.81701(19) 0.3403(2) 0.63746(8) 0.0503(6) Uani 1 1 d . . . . .
N1 N 0.7221(2) 0.5501(2) 0.62252(8) 0.0400(6) Uani 1 1 d . . . . .
H1 H 0.738517 0.636025 0.624541 0.048 Uiso 1 1 calc R U . . .
C8 C 0.5871(3) 0.5077(3) 0.59938(10) 0.0394(7) Uani 1 1 d . . . . .
C7 C 0.8259(3) 0.4655(3) 0.64149(10) 0.0389(7) Uani 1 1 d . . . . .
C5 C 0.9513(2) 0.5290(3) 0.67015(10) 0.0375(7) Uani 1 1 d . . . . .
C4 C 0.9888(3) 0.6661(3) 0.66486(11) 0.0419(7) Uani 1 1 d . . . . .
H4 H 0.935367 0.721642 0.642239 0.050 Uiso 1 1 calc R U . . .
C6 C 1.0329(3) 0.4475(3) 0.70416(10) 0.0424(7) Uani 1 1 d . . . . .
H6 H 1.010608 0.355591 0.707370 0.051 Uiso 1 1 calc R U . . .
C11 C 0.3158(3) 0.4348(3) 0.55583(11) 0.0441(8) Uani 1 1 d . . . . .
C9 C 0.5788(3) 0.4037(3) 0.56278(11) 0.0430(8) Uani 1 1 d . . . . .
H9 H 0.663195 0.357766 0.552469 0.052 Uiso 1 1 calc R U . . .
C10 C 0.4440(3) 0.3685(3) 0.54156(10) 0.0457(8) Uani 1 1 d . . . . .
H10 H 0.439400 0.298359 0.517034 0.055 Uiso 1 1 calc R U . . .
C3 C 1.1050(3) 0.7195(3) 0.69313(11) 0.0449(7) Uani 1 1 d . . . . .
H3 H 1.129948 0.810576 0.689173 0.054 Uiso 1 1 calc R U . . .
C2 C 1.1465(3) 0.5023(3) 0.73309(10) 0.0494(8) Uani 1 1 d . . . . .
H2 H 1.198088 0.447904 0.756658 0.059 Uiso 1 1 calc R U . . .
C14 C 0.4600(3) 0.5758(3) 0.61431(12) 0.0462(8) Uani 1 1 d . . . . .
H14 H 0.464655 0.645607 0.638997 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3266(3) 0.5396(3) 0.59238(11) 0.0502(8) Uani 1 1 d . . . . .
H13 H 0.242409 0.586408 0.602300 0.060 Uiso 1 1 calc R U . . .
C1 C 1.1841(3) 0.6382(3) 0.72721(12) 0.0481(8) Uani 1 1 d . . . . .
H1A H 1.262326 0.674371 0.746141 0.058 Uiso 1 1 calc R U . . .
C12 C 0.1699(3) 0.3971(4) 0.53207(13) 0.0604(10) Uani 1 1 d . . . . .
H12A H 0.175204 0.405172 0.494404 0.091 Uiso 1 1 calc R U . . .
H12B H 0.095428 0.457052 0.545325 0.091 Uiso 1 1 calc R U . . .
H12C H 0.146093 0.305110 0.541354 0.091 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 C7 1.239(3) . ?
N1 H1 0.8600 . ?
N1 C8 1.425(3) . ?
N1 C7 1.349(3) . ?
C8 C9 1.383(4) . ?
C8 C14 1.391(4) . ?
C7 C5 1.492(3) . ?
C5 C4 1.398(4) . ?
C5 C6 1.393(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C2 1.379(3) . ?
C11 C10 1.386(4) . ?
C11 C13 1.390(4) . ?
C11 C12 1.506(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(4) . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
C3 C1 1.381(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.389(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(4) . ?
C13 H13 0.9300 . ?
C1 H1A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C8 N1 H1 117.6 . . ?
C7 N1 H1 117.6 . . ?
C7 N1 C8 124.9(2) . . ?
C9 C8 N1 122.7(2) . . ?
C9 C8 C14 119.6(2) . . ?
C14 C8 N1 117.8(2) . . ?
O1 C7 N1 122.5(2) . . ?
O1 C7 C5 120.5(2) . . ?
N1 C7 C5 117.0(2) . . ?
C4 C5 C7 123.0(2) . . ?
C6 C5 C7 118.0(2) . . ?
C6 C5 C4 119.0(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C6 H6 119.8 . . ?
C2 C6 C5 120.4(3) . . ?
C2 C6 H6 119.8 . . ?
C10 C11 C13 117.6(2) . . ?
C10 C11 C12 121.6(3) . . ?
C13 C11 C12 120.8(2) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C11 C10 H10 119.0 . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 H10 119.0 . . ?
C4 C3 H3 119.8 . . ?
C1 C3 C4 120.3(3) . . ?
C1 C3 H3 119.8 . . ?
C6 C2 H2 119.8 . . ?
C6 C2 C1 120.3(3) . . ?
C1 C2 H2 119.8 . . ?
C8 C14 H14 120.1 . . ?
C13 C14 C8 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C11 C13 H13 119.3 . . ?
C14 C13 C11 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C3 C1 C2 119.7(3) . . ?
C3 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O1 C7 C5 C4 163.1(3) . . . . ?
O1 C7 C5 C6 -17.8(3) . . . . ?
N1 C8 C9 C10 -179.5(2) . . . . ?
N1 C8 C14 C13 179.1(3) . . . . ?
N1 C7 C5 C4 -19.5(3) . . . . ?
N1 C7 C5 C6 159.6(2) . . . . ?
C8 N1 C7 O1 4.6(4) . . . . ?
C8 N1 C7 C5 -172.7(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C8 C14 C13 C11 0.7(5) . . . . ?
C7 N1 C8 C9 -45.1(4) . . . . ?
C7 N1 C8 C14 135.5(3) . . . . ?
C7 C5 C4 C3 179.0(2) . . . . ?
C7 C5 C6 C2 -177.6(2) . . . . ?
C5 C4 C3 C1 -0.6(4) . . . . ?
C5 C6 C2 C1 -2.3(4) . . . . ?
C4 C5 C6 C2 1.6(4) . . . . ?
C4 C3 C1 C2 -0.1(4) . . . . ?
C6 C5 C4 C3 -0.1(4) . . . . ?
C6 C2 C1 C3 1.6(4) . . . . ?
C9 C8 C14 C13 -0.2(4) . . . . ?
C10 C11 C13 C14 -0.8(4) . . . . ?
C14 C8 C9 C10 -0.2(4) . . . . ?
C13 C11 C10 C9 0.3(4) . . . . ?
C12 C11 C10 C9 179.2(3) . . . . ?
C12 C11 C13 C14 -179.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.688
_oxdiff_exptl_absorpt_empirical_full_min 0.464
