# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_takaishi_autored
_database_code_depnum_ccdc_archive 'CCDC 2413450'
loop_
_audit_author_name
_audit_author_address
'Kazuto Takaishi'
;Okayama University
Japan
;
_audit_update_record             
;
2024-12-28 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2023-01-27
_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         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         O1N2C15H15
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.0306(3)
_cell_length_b                   10.3023(6)
_cell_length_c                   16.1959(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1006.24(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8780
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.4750
_cell_measurement_theta_min      2.3310
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90957
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21034
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.761
_diffrn_reflns_theta_min         2.343
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 7.111
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  75.00   0.50    1.00    --  -15.00  45.00   0.00  360
  2  ω   -105.00  75.00   0.50    1.00    --  -15.00  45.00  90.00  360
  3  ω   -105.00  75.00   0.50    1.00    --  -15.00  45.00 180.00  360
  4  ω   -105.00  75.00   0.50    1.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device       'AFC11 SATURN724+ Right'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0638116000
_diffrn_orient_matrix_UB_12      -0.0447543000
_diffrn_orient_matrix_UB_13      0.0232501000
_diffrn_orient_matrix_UB_21      0.0981794000
_diffrn_orient_matrix_UB_22      0.0238864000
_diffrn_orient_matrix_UB_23      -0.0187368000
_diffrn_orient_matrix_UB_31      0.0110255000
_diffrn_orient_matrix_UB_32      0.0465392000
_diffrn_orient_matrix_UB_33      0.0320436000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'MicroMax 007'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                2071
_reflns_number_total             2943
_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       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.023
_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)+(0.0490P)²+0.1289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12)
;
_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 0.8488(3) 0.33656(17) 0.71212(12) 0.0402(5) Uani 1 1 d . . . . .
N1 N 0.8064(4) 0.8286(2) 0.66967(14) 0.0338(5) Uani 1 1 d . . . . .
H1 H 0.930650 0.841393 0.696987 0.041 Uiso 1 1 calc R U . . .
N2 N 0.5882(3) 0.4945(2) 0.69649(13) 0.0309(5) Uani 1 1 d . . . . .
C1 C 0.7043(5) 0.9163(2) 0.61793(15) 0.0327(6) Uani 1 1 d . . . . .
C2 C 0.7642(6) 1.0430(3) 0.59653(17) 0.0436(7) Uani 1 1 d . . . . .
H2 H 0.893959 1.082538 0.618320 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6274(6) 1.1081(3) 0.54259(19) 0.0523(9) Uani 1 1 d . . . . .
H3 H 0.664900 1.194024 0.526426 0.063 Uiso 1 1 calc R U . . .
C4 C 0.4359(6) 1.0517(3) 0.51109(19) 0.0506(9) Uani 1 1 d . . . . .
H4 H 0.345367 1.099862 0.474140 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3748(5) 0.9272(3) 0.53242(16) 0.0397(7) Uani 1 1 d . . . . .
H5 H 0.243056 0.889618 0.510904 0.048 Uiso 1 1 calc R U . . .
C6 C 0.5111(4) 0.8574(2) 0.58646(15) 0.0304(6) Uani 1 1 d . . . . .
C7 C 0.5007(4) 0.7299(2) 0.62134(15) 0.0274(6) Uani 1 1 d . . . . .
C8 C 0.3355(4) 0.6246(2) 0.60940(15) 0.0312(6) Uani 1 1 d . . . . .
H8A H 0.362911 0.580046 0.556197 0.037 Uiso 1 1 calc R U . . .
H8B H 0.184078 0.661557 0.608115 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3553(4) 0.5281(3) 0.68011(16) 0.0338(6) Uani 1 1 d . . . . .
H9A H 0.288812 0.566078 0.730511 0.041 Uiso 1 1 calc R U . . .
H9B H 0.271776 0.448364 0.666222 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7367(4) 0.5995(3) 0.72127(17) 0.0340(6) Uani 1 1 d . . . . .
H10A H 0.892798 0.574171 0.711433 0.041 Uiso 1 1 calc R U . . .
H10B H 0.718091 0.618340 0.780814 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6798(4) 0.7171(2) 0.67113(15) 0.0282(5) Uani 1 1 d . . . . .
C12 C 0.6599(5) 0.3726(3) 0.69492(15) 0.0330(6) Uani 1 1 d . . . . .
H12 H 0.556354 0.307644 0.679170 0.040 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 C12 1.230(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.378(3) . ?
N1 C11 1.380(3) . ?
N2 C9 1.471(3) . ?
N2 C10 1.461(3) . ?
N2 C12 1.328(3) . ?
C1 C2 1.399(4) . ?
C1 C6 1.409(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(4) . ?
C6 C7 1.431(4) . ?
C7 C8 1.486(3) . ?
C7 C11 1.354(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.521(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.498(4) . ?
C12 H12 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
C1 N1 H1 126.0 . . ?
C1 N1 C11 108.0(2) . . ?
C11 N1 H1 126.0 . . ?
C10 N2 C9 117.4(2) . . ?
C12 N2 C9 122.0(2) . . ?
C12 N2 C10 120.4(2) . . ?
N1 C1 C2 130.4(3) . . ?
N1 C1 C6 107.9(2) . . ?
C2 C1 C6 121.7(3) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C7 106.7(2) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 133.9(3) . . ?
C6 C7 C8 130.4(2) . . ?
C11 C7 C6 106.9(2) . . ?
C11 C7 C8 122.7(2) . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
C7 C8 C9 109.1(2) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
N2 C9 C8 111.4(2) . . ?
N2 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 H10A 110.1 . . ?
N2 C10 H10B 110.1 . . ?
N2 C10 C11 108.03(19) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
N1 C11 C10 123.8(2) . . ?
C7 C11 N1 110.5(2) . . ?
C7 C11 C10 125.8(2) . . ?
O1 C12 N2 125.6(2) . . ?
O1 C12 H12 117.2 . . ?
N2 C12 H12 117.2 . . ?

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
N1 C1 C2 C3 -179.9(3) . . . . ?
N1 C1 C6 C5 179.4(2) . . . . ?
N1 C1 C6 C7 -0.1(3) . . . . ?
N2 C10 C11 N1 -170.4(2) . . . . ?
N2 C10 C11 C7 9.5(4) . . . . ?
C1 N1 C11 C7 0.6(3) . . . . ?
C1 N1 C11 C10 -179.5(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C1 C6 C7 C8 -179.2(2) . . . . ?
C1 C6 C7 C11 0.4(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C6 C7 -179.6(2) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C5 C6 C7 C8 1.4(5) . . . . ?
C5 C6 C7 C11 -178.9(3) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C6 C7 C8 C9 -161.3(3) . . . . ?
C6 C7 C11 N1 -0.6(3) . . . . ?
C6 C7 C11 C10 179.5(2) . . . . ?
C7 C8 C9 N2 -46.1(3) . . . . ?
C8 C7 C11 N1 179.1(2) . . . . ?
C8 C7 C11 C10 -0.8(4) . . . . ?
C9 N2 C10 C11 -39.7(3) . . . . ?
C9 N2 C12 O1 -176.0(2) . . . . ?
C10 N2 C9 C8 61.3(3) . . . . ?
C10 N2 C12 O1 -0.9(4) . . . . ?
C11 N1 C1 C2 179.1(3) . . . . ?
C11 N1 C1 C6 -0.3(3) . . . . ?
C11 C7 C8 C9 19.1(3) . . . . ?
C12 N2 C9 C8 -123.5(2) . . . . ?
C12 N2 C10 C11 145.0(2) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.150
_oxdiff_exptl_absorpt_empirical_full_min 0.861
####################################################################### 
# 
# 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_takaishi_autored_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2413452'
loop_
_audit_author_name
_audit_author_address
'Kazuto Takaishi'
;Okayama University
Japan
;
_audit_update_record             
;
2024-12-28 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2024-05-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 N2'
_chemical_formula_sum            'C12 H14 N2'
_chemical_formula_weight         186.25
_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 0.0033 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'

_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 1 21/n 1'
_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                   12.4491(7)
_cell_length_b                   6.2533(2)
_cell_length_c                   13.2178(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.117(6)
_cell_angle_gamma                90
_cell_volume                     977.97(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9100
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.8800
_cell_measurement_theta_min      1.9550
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18579
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.778
_diffrn_reflns_theta_min         1.963
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 7.111
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  75.00   0.50    1.00    --  -15.00  45.00   0.00  360
  2  ω   -105.00  75.00   0.50    1.00    --  -15.00  45.00  90.00  360
  3  ω   -105.00  75.00   0.50    1.00    --  -15.00  45.00 180.00  360
  4  ω   -105.00  75.00   0.50    1.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device       'AFC11 SATURN724+ Right'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0240892000
_diffrn_orient_matrix_UB_12      -0.1038452000
_diffrn_orient_matrix_UB_13      0.0068762000
_diffrn_orient_matrix_UB_21      -0.0280711000
_diffrn_orient_matrix_UB_22      -0.0237612000
_diffrn_orient_matrix_UB_23      0.0378508000
_diffrn_orient_matrix_UB_31      -0.0471680000
_diffrn_orient_matrix_UB_32      -0.0390120000
_diffrn_orient_matrix_UB_33      -0.0413196000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'MicroMax 007'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2141
_reflns_number_total             2840
_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 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.023
_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)+(0.0729P)²+0.3967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1525
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10)
2.c 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
N1 N 0.26140(10) 0.31896(19) 0.39558(9) 0.0175(3) Uani 1 1 d . . . . .
H1 H 0.231757 0.192299 0.375165 0.021 Uiso 1 1 calc R U . . .
N2 N 0.41992(10) 0.52513(18) 0.22063(9) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.33740(11) 0.4258(2) 0.35637(11) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.38198(12) 0.3432(2) 0.27193(11) 0.0167(3) Uani 1 1 d . . . . .
H2A H 0.446067 0.245028 0.303424 0.020 Uiso 1 1 calc R U . . .
H2B H 0.322194 0.262778 0.218391 0.020 Uiso 1 1 calc R U . . .
C3 C 0.49996(12) 0.6601(2) 0.30181(11) 0.0194(3) Uani 1 1 d . . . . .
H3A H 0.531163 0.771256 0.265487 0.023 Uiso 1 1 calc R U . . .
H3B H 0.563624 0.570372 0.344079 0.023 Uiso 1 1 calc R U . . .
C4 C 0.44505(13) 0.7686(2) 0.37701(12) 0.0210(3) Uani 1 1 d . . . . .
H4A H 0.504430 0.817054 0.441944 0.025 Uiso 1 1 calc R U . . .
H4B H 0.402126 0.895780 0.341734 0.025 Uiso 1 1 calc R U . . .
C5 C 0.36714(12) 0.6167(2) 0.40702(11) 0.0163(3) Uani 1 1 d . . . . .
C6 C 0.30593(12) 0.6365(2) 0.48203(10) 0.0165(3) Uani 1 1 d . . . . .
C7 C 0.29931(12) 0.7922(2) 0.55635(11) 0.0205(3) Uani 1 1 d . . . . .
H7 H 0.341431 0.921089 0.563376 0.025 Uiso 1 1 calc R U . . .
C8 C 0.23078(13) 0.7559(2) 0.61916(11) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.226552 0.860142 0.670058 0.027 Uiso 1 1 calc R U . . .
C9 C 0.16732(13) 0.5670(3) 0.60877(12) 0.0236(3) Uani 1 1 d . . . . .
H9 H 0.120799 0.545726 0.652863 0.028 Uiso 1 1 calc R U . . .
C10 C 0.17111(13) 0.4110(2) 0.53564(11) 0.0213(3) Uani 1 1 d . . . . .
H10 H 0.127837 0.283578 0.528716 0.026 Uiso 1 1 calc R U . . .
C11 C 0.24041(12) 0.4470(2) 0.47260(11) 0.0170(3) Uani 1 1 d . . . . .
C12 C 0.47631(13) 0.4420(2) 0.14659(12) 0.0214(3) Uani 1 1 d . . . . .
H12A H 0.543233 0.359883 0.186194 0.032 Uiso 1 1 calc R U . . .
H12B H 0.499254 0.561444 0.109942 0.032 Uiso 1 1 calc R U . . .
H12C H 0.424153 0.349003 0.094134 0.032 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
N1 H1 0.8800 . ?
N1 C1 1.3840(17) . ?
N1 C11 1.3823(18) . ?
N2 C2 1.4752(17) . ?
N2 C3 1.4806(18) . ?
N2 C12 1.4656(18) . ?
C1 C2 1.4852(19) . ?
C1 C5 1.3627(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.529(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.4966(19) . ?
C5 C6 1.431(2) . ?
C6 C7 1.4040(19) . ?
C6 C11 1.4219(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.404(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 N1 H1 126.1 . . ?
C11 N1 H1 126.1 . . ?
C11 N1 C1 107.70(12) . . ?
C2 N2 C3 110.25(11) . . ?
C12 N2 C2 108.76(11) . . ?
C12 N2 C3 109.39(11) . . ?
N1 C1 C2 124.92(12) . . ?
C5 C1 N1 110.60(12) . . ?
C5 C1 C2 124.48(13) . . ?
N2 C2 C1 108.97(11) . . ?
N2 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 H3A 109.0 . . ?
N2 C3 H3B 109.0 . . ?
N2 C3 C4 112.83(12) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.38(12) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C1 C5 C4 121.69(13) . . ?
C1 C5 C6 107.10(12) . . ?
C6 C5 C4 131.10(12) . . ?
C7 C6 C5 134.77(13) . . ?
C7 C6 C11 118.85(13) . . ?
C11 C6 C5 106.38(12) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.20(14) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 120.90(14) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.38(14) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 121.1 . . ?
C9 C10 C11 117.79(14) . . ?
C11 C10 H10 121.1 . . ?
N1 C11 C6 108.21(12) . . ?
N1 C11 C10 129.91(13) . . ?
C10 C11 C6 121.87(13) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 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
N1 C1 C2 N2 156.71(12) . . . . ?
N1 C1 C5 C4 -177.58(12) . . . . ?
N1 C1 C5 C6 -0.88(15) . . . . ?
N2 C3 C4 C5 41.14(16) . . . . ?
C1 N1 C11 C6 -0.64(15) . . . . ?
C1 N1 C11 C10 -179.49(14) . . . . ?
C1 C5 C6 C7 -179.81(15) . . . . ?
C1 C5 C6 C11 0.47(15) . . . . ?
C2 N2 C3 C4 -65.20(15) . . . . ?
C2 C1 C5 C4 3.2(2) . . . . ?
C2 C1 C5 C6 179.95(12) . . . . ?
C3 N2 C2 C1 53.24(14) . . . . ?
C3 C4 C5 C1 -10.94(19) . . . . ?
C3 C4 C5 C6 173.25(13) . . . . ?
C4 C5 C6 C7 -3.5(3) . . . . ?
C4 C5 C6 C11 176.74(14) . . . . ?
C5 C1 C2 N2 -24.25(18) . . . . ?
C5 C6 C7 C8 -178.78(14) . . . . ?
C5 C6 C11 N1 0.11(15) . . . . ?
C5 C6 C11 C10 179.07(13) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C7 C6 C11 N1 -179.67(12) . . . . ?
C7 C6 C11 C10 -0.7(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 N1 178.85(14) . . . . ?
C9 C10 C11 C6 0.1(2) . . . . ?
C11 N1 C1 C2 -179.88(12) . . . . ?
C11 N1 C1 C5 0.96(16) . . . . ?
C11 C6 C7 C8 0.9(2) . . . . ?
C12 N2 C2 C1 173.18(11) . . . . ?
C12 N2 C3 C4 175.24(11) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.227
_oxdiff_exptl_absorpt_empirical_full_min 0.527
