# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_tr226
_database_code_depnum_ccdc_archive 'CCDC 2306780'
loop_
_audit_author_name
_audit_author_address
'Jan Grzegorz Malecki'
;University of Silesia  Katowice
Poland
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;
_audit_creation_date             2023-10-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 N2 O2'
_chemical_formula_sum            'C15 H12 N2 O2'
_chemical_formula_weight         252.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H12 N2 O2'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
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                   10.4760(8)
_cell_length_b                   5.0246(5)
_cell_length_c                   22.8902(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.761(7)
_cell_angle_gamma                90
_cell_volume                     1193.86(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2817
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.9050
_cell_measurement_theta_min      4.1000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8253
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.416
_diffrn_reflns_theta_min         3.542
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  39.00   1.00   17.05    --   10.84 -57.00 120.00  101
  2  ω    -91.00  30.00   1.00   17.05    --  -11.00 -19.00 -30.00  121
  3  ω    -44.00   4.00   1.00   17.05    --  -11.00  77.00 -30.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0146809000
_diffrn_orient_matrix_UB_12      -0.0627238000
_diffrn_orient_matrix_UB_13      -0.0260509000
_diffrn_orient_matrix_UB_21      -0.0456138000
_diffrn_orient_matrix_UB_22      -0.1011568000
_diffrn_orient_matrix_UB_23      0.0034515000
_diffrn_orient_matrix_UB_31      -0.0487663000
_diffrn_orient_matrix_UB_32      0.0758094000
_diffrn_orient_matrix_UB_33      -0.0169342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1944
_reflns_number_total             2859
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.046
_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)+(0.0682P)²+0.1980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1467
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 1.10202(13) 1.2285(3) 0.03113(6) 0.0598(5) Uani 1 1 d . . . . .
O2 O 0.48241(11) 0.2803(3) 0.13065(5) 0.0464(4) Uani 1 1 d . . . . .
N1 N 0.90390(12) 1.1871(3) 0.17193(5) 0.0316(3) Uani 1 1 d . . . . .
N2 N 0.94241(12) 1.0585(3) 0.07739(6) 0.0352(4) Uani 1 1 d . . . . .
H2 H 0.9240(18) 0.955(4) 0.0451(9) 0.050(5) Uiso 1 1 d . . . . .
C1 C 0.87754(14) 1.0377(3) 0.12584(6) 0.0290(4) Uani 1 1 d . . . . .
C2 C 1.04340(15) 1.2289(4) 0.07445(7) 0.0374(4) Uani 1 1 d . . . . .
C3 C 1.07384(14) 1.3995(3) 0.12502(6) 0.0319(4) Uani 1 1 d . . . . .
C4 C 1.17273(16) 1.5870(4) 0.12738(7) 0.0409(4) Uani 1 1 d . . . . .
H4 H 1.220561 1.602117 0.096138 0.049 Uiso 1 1 calc R U . . .
C5 C 1.19931(17) 1.7483(4) 0.17559(8) 0.0420(4) Uani 1 1 d . . . . .
H5 H 1.265175 1.873322 0.177221 0.050 Uiso 1 1 calc R U . . .
C6 C 1.12722(17) 1.7247(4) 0.22235(7) 0.0397(4) Uani 1 1 d . . . . .
H6 H 1.145318 1.835197 0.255016 0.048 Uiso 1 1 calc R U . . .
C7 C 1.03017(16) 1.5411(4) 0.22078(7) 0.0366(4) Uani 1 1 d . . . . .
H7 H 0.982928 1.528091 0.252264 0.044 Uiso 1 1 calc R U . . .
C8 C 1.00181(14) 1.3730(3) 0.17200(6) 0.0301(4) Uani 1 1 d . . . . .
C9 C 0.77499(14) 0.8348(3) 0.12424(6) 0.0304(4) Uani 1 1 d . . . . .
C10 C 0.73768(16) 0.6742(4) 0.07587(7) 0.0359(4) Uani 1 1 d . . . . .
H10 H 0.778630 0.692557 0.042486 0.043 Uiso 1 1 calc R U . . .
C11 C 0.64041(16) 0.4861(4) 0.07597(7) 0.0374(4) Uani 1 1 d . . . . .
H11 H 0.616118 0.381547 0.042796 0.045 Uiso 1 1 calc R U . . .
C12 C 0.57986(14) 0.4551(3) 0.12573(7) 0.0340(4) Uani 1 1 d . . . . .
C13 C 0.61820(16) 0.6108(4) 0.17495(7) 0.0388(4) Uani 1 1 d . . . . .
H13 H 0.579074 0.588132 0.208741 0.047 Uiso 1 1 calc R U . . .
C14 C 0.71313(15) 0.7977(4) 0.17431(7) 0.0369(4) Uani 1 1 d . . . . .
H14 H 0.736988 0.901778 0.207598 0.044 Uiso 1 1 calc R U . . .
C15 C 0.43632(19) 0.1239(4) 0.08075(9) 0.0530(5) Uani 1 1 d . . . . .
H15A H 0.408284 0.238379 0.047945 0.079 Uiso 1 1 calc R U . . .
H15B H 0.365306 0.016903 0.089414 0.079 Uiso 1 1 calc R U . . .
H15C H 0.504141 0.010375 0.071075 0.079 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 1.2347(19) . ?
O2 C12 1.3629(19) . ?
O2 C15 1.416(2) . ?
N1 C1 1.294(2) . ?
N1 C8 1.387(2) . ?
N2 H2 0.90(2) . ?
N2 C1 1.3808(19) . ?
N2 C2 1.370(2) . ?
C1 C9 1.478(2) . ?
C2 C3 1.441(2) . ?
C3 C4 1.396(2) . ?
C3 C8 1.401(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.400(2) . ?
C9 C10 1.383(2) . ?
C9 C14 1.403(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(2) . ?
C12 C13 1.386(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C12 O2 C15 117.94(13) . . ?
C1 N1 C8 117.91(13) . . ?
C1 N2 H2 122.7(12) . . ?
C2 N2 H2 113.6(12) . . ?
C2 N2 C1 123.63(14) . . ?
N1 C1 N2 122.49(14) . . ?
N1 C1 C9 119.67(13) . . ?
N2 C1 C9 117.85(14) . . ?
O1 C2 N2 120.62(15) . . ?
O1 C2 C3 124.48(15) . . ?
N2 C2 C3 114.90(13) . . ?
C4 C3 C2 120.99(14) . . ?
C4 C3 C8 120.56(15) . . ?
C8 C3 C2 118.45(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.03(16) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.74(16) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.91(16) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.28(15) . . ?
C8 C7 H7 119.9 . . ?
N1 C8 C3 122.55(14) . . ?
N1 C8 C7 118.98(14) . . ?
C7 C8 C3 118.47(15) . . ?
C10 C9 C1 123.25(14) . . ?
C10 C9 C14 117.69(15) . . ?
C14 C9 C1 119.06(15) . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.56(14) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.66(15) . . ?
C12 C11 H11 120.2 . . ?
O2 C12 C11 124.86(15) . . ?
O2 C12 C13 115.78(14) . . ?
C11 C12 C13 119.36(15) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.65(14) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.06(16) . . ?
C13 C14 H14 119.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C2 C3 C4 2.0(3) . . . . ?
O1 C2 C3 C8 -177.97(18) . . . . ?
O2 C12 C13 C14 -178.37(15) . . . . ?
N1 C1 C9 C10 177.50(15) . . . . ?
N1 C1 C9 C14 -3.7(2) . . . . ?
N2 C1 C9 C10 -2.8(2) . . . . ?
N2 C1 C9 C14 175.96(14) . . . . ?
N2 C2 C3 C4 -178.60(16) . . . . ?
N2 C2 C3 C8 1.4(2) . . . . ?
C1 N1 C8 C3 -1.4(2) . . . . ?
C1 N1 C8 C7 178.56(14) . . . . ?
C1 N2 C2 O1 176.13(17) . . . . ?
C1 N2 C2 C3 -3.3(2) . . . . ?
C1 C9 C10 C11 -179.79(15) . . . . ?
C1 C9 C14 C13 -179.54(15) . . . . ?
C2 N2 C1 N1 2.9(2) . . . . ?
C2 N2 C1 C9 -176.72(14) . . . . ?
C2 C3 C4 C5 179.46(16) . . . . ?
C2 C3 C8 N1 0.9(2) . . . . ?
C2 C3 C8 C7 -179.13(15) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C3 C8 N1 -179.10(15) . . . . ?
C4 C3 C8 C7 0.9(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 N1 179.33(15) . . . . ?
C6 C7 C8 C3 -0.7(2) . . . . ?
C8 N1 C1 N2 -0.4(2) . . . . ?
C8 N1 C1 C9 179.26(13) . . . . ?
C8 C3 C4 C5 -0.6(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C9 C14 C13 -0.7(3) . . . . ?
C10 C11 C12 O2 179.05(15) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C14 C9 C10 C11 1.4(3) . . . . ?
C15 O2 C12 C11 -2.1(2) . . . . ?
C15 O2 C12 C13 177.58(16) . . . . ?

_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 1.639
_oxdiff_exptl_absorpt_empirical_full_min 0.309
