# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_mj24660_0m
_database_code_depnum_ccdc_archive 'CCDC 2520666'
loop_
_audit_author_name
_audit_author_address
'Fei Tong'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-18 downloaded from the CCDC.
;
_audit_creation_date             2024-07-03
_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         'C13 H11 N O2'
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1629(4)
_cell_length_b                   7.8641(4)
_cell_length_c                   11.2471(6)
_cell_angle_alpha                103.649(2)
_cell_angle_beta                 95.695(2)
_cell_angle_gamma                113.196(2)
_cell_volume                     552.63(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4569
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      5.58
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1318 before and 0.0772 after correction.
The Ratio of minimum to maximum transmission is 0.7120.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7711
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.927
_diffrn_reflns_theta_min         3.603
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1729
_reflns_number_total             2086
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²+0.0696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1374
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.36736(16) 1.08125(14) 0.84241(9) 0.0329(3) Uani 1 1 d . . . . .
O2 O 0.41828(16) 1.12478(14) 0.65527(9) 0.0357(3) Uani 1 1 d . . . . .
N1 N 0.1846(2) 0.60852(19) 0.83168(13) 0.0445(4) Uani 1 1 d . . . . .
C1 C 0.2240(2) 0.2014(2) 0.19279(14) 0.0337(4) Uani 1 1 d . . . . .
H1 H 0.262484 0.300735 0.153291 0.040 Uiso 1 1 calc R U . . .
C2 C 0.1821(2) 0.0144(2) 0.12409(14) 0.0365(4) Uani 1 1 d . . . . .
H2 H 0.194149 -0.013293 0.039064 0.044 Uiso 1 1 calc R U . . .
C3 C 0.1224(2) -0.1313(2) 0.18041(15) 0.0365(4) Uani 1 1 d . . . . .
H3 H 0.091199 -0.260369 0.133723 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1081(2) -0.0892(2) 0.30506(15) 0.0356(4) Uani 1 1 d . . . . .
H4 H 0.066614 -0.190079 0.343260 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1535(2) 0.0981(2) 0.37441(14) 0.0317(4) Uani 1 1 d . . . . .
H5 H 0.145469 0.125447 0.460152 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2114(2) 0.2477(2) 0.31860(13) 0.0274(3) Uani 1 1 d . . . . .
C7 C 0.2603(2) 0.4485(2) 0.38604(14) 0.0305(4) Uani 1 1 d . . . . .
H7 H 0.303572 0.539270 0.340228 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2513(2) 0.5198(2) 0.50534(13) 0.0299(4) Uani 1 1 d . . . . .
H8 H 0.205823 0.433925 0.554266 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3084(2) 0.7219(2) 0.56039(13) 0.0284(4) Uani 1 1 d . . . . .
H9 H 0.355613 0.803715 0.509146 0.034 Uiso 1 1 calc R U . . .
C10 C 0.30189(19) 0.8074(2) 0.67774(13) 0.0261(3) Uani 1 1 d . . . . .
C11 C 0.3682(2) 1.0202(2) 0.72136(13) 0.0269(3) Uani 1 1 d . . . . .
C12 C 0.2377(2) 0.6988(2) 0.76439(13) 0.0301(4) Uani 1 1 d . . . . .
C13 C 0.4412(3) 1.2879(2) 0.89502(15) 0.0413(4) Uani 1 1 d . . . . .
H13A H 0.352926 1.331829 0.850600 0.062 Uiso 1 1 calc R U . . .
H13B H 0.584859 1.353648 0.886281 0.062 Uiso 1 1 calc R U . . .
H13C H 0.436177 1.318618 0.983964 0.062 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 C11 1.3339(16) . ?
O1 C13 1.4412(18) . ?
O2 C11 1.2109(16) . ?
N1 C12 1.1488(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(2) . ?
C1 C6 1.397(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.4023(19) . ?
C6 C7 1.462(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.345(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.432(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.347(2) . ?
C10 C11 1.485(2) . ?
C10 C12 1.4364(18) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C11 O1 C13 115.45(11) . . ?
C2 C1 H1 119.1 . . ?
C2 C1 C6 121.77(13) . . ?
C6 C1 H1 119.1 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.35(14) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.01(14) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.70(13) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.24(13) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 117.92(13) . . ?
C1 C6 C7 118.95(12) . . ?
C5 C6 C7 123.13(13) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 C6 127.66(13) . . ?
C8 C7 H7 116.2 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.63(13) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 116.8 . . ?
C10 C9 C8 126.37(13) . . ?
C10 C9 H9 116.8 . . ?
C9 C10 C11 119.88(12) . . ?
C9 C10 C12 121.66(13) . . ?
C12 C10 C11 118.43(12) . . ?
O1 C11 C10 111.48(11) . . ?
O2 C11 O1 124.47(13) . . ?
O2 C11 C10 124.05(13) . . ?
N1 C12 C10 178.59(15) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C1 C2 C3 C4 -1.0(2) . . . . ?
C1 C6 C7 C8 177.89(13) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C6 C7 179.25(13) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C5 C6 C7 179.63(13) . . . . ?
C5 C6 C7 C8 -2.6(2) . . . . ?
C6 C1 C2 C3 1.2(2) . . . . ?
C6 C7 C8 C9 178.60(12) . . . . ?
C7 C8 C9 C10 178.84(12) . . . . ?
C8 C9 C10 C11 179.58(12) . . . . ?
C8 C9 C10 C12 1.4(2) . . . . ?
C9 C10 C11 O1 -174.91(11) . . . . ?
C9 C10 C11 O2 4.5(2) . . . . ?
C12 C10 C11 O1 3.31(17) . . . . ?
C12 C10 C11 O2 -177.31(12) . . . . ?
C13 O1 C11 O2 -2.85(19) . . . . ?
C13 O1 C11 C10 176.53(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_20251114_y30240328_lj_1_a
_database_code_depnum_ccdc_archive 'CCDC 2520711'
loop_
_audit_author_name
_audit_author_address
'Fei Tong'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-18 downloaded from the CCDC.
;
_audit_creation_date             2025-11-14
_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         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.45
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4552(8)
_cell_length_b                   7.6250(6)
_cell_length_c                   11.4156(8)
_cell_angle_alpha                72.773(6)
_cell_angle_beta                 89.286(8)
_cell_angle_gamma                70.571(7)
_cell_volume                     581.85(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1069
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      71.320
_cell_measurement_theta_min      4.073
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0943 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.8053.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8081
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         4.073
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'photon counting detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'PHOTON III detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms Diamond II'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1222
_reflns_number_total             2128
_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       'SAINT V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0886
_refine_ls_restrained_S_all      1.017
_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)+(0.1876P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2453
_refine_ls_wR_factor_ref         0.2946
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.7651(4) 0.7542(3) 0.8485(2) 0.0840(8) Uani 1 1 d . . . . .
O2 O 0.6617(5) 0.9725(3) 0.6620(2) 0.0941(9) Uani 1 1 d . . . . .
N1 N 0.9251(7) 0.2899(5) 0.8371(4) 0.1178(15) Uani 1 1 d . . . . .
C1 C 0.6725(6) 0.4180(5) 0.3311(3) 0.0814(10) Uani 1 1 d . . . . .
C2 C 0.7674(6) 0.2185(5) 0.3790(4) 0.0850(11) Uani 1 1 d . . . . .
H2 H 0.788065 0.160110 0.463963 0.102 Uiso 1 1 calc R U . . .
C3 C 0.8317(7) 0.1051(6) 0.3025(5) 0.0993(13) Uani 1 1 d . . . . .
H3 H 0.893623 -0.029066 0.336194 0.119 Uiso 1 1 calc R U . . .
C4 C 0.8047(8) 0.1893(8) 0.1766(5) 0.1111(16) Uani 1 1 d . . . . .
H4 H 0.846079 0.112436 0.124994 0.133 Uiso 1 1 calc R U . . .
C5 C 0.7173(8) 0.3854(8) 0.1284(4) 0.1106(16) Uani 1 1 d . . . . .
H5 H 0.701861 0.443256 0.043449 0.133 Uiso 1 1 calc R U . . .
C6 C 0.6510(7) 0.4998(6) 0.2037(4) 0.0950(12) Uani 1 1 d . . . . .
H6 H 0.590755 0.634021 0.168890 0.114 Uiso 1 1 calc R U . . .
C7 C 0.5598(7) 0.5395(5) 0.4101(3) 0.0871(12) Uani 1 1 d . . . . .
H7 H 0.533652 0.678501 0.366808 0.105 Uiso 1 1 calc R U . . .
C8 C 0.6368(7) 0.4924(5) 0.5451(3) 0.0877(12) Uani 1 1 d . . . . .
H8 H 0.746809 0.370664 0.572277 0.105 Uiso 1 1 calc R U . . .
C9 C 0.6702(6) 0.6536(5) 0.5788(3) 0.0823(11) Uani 1 1 d . . . . .
H9 H 0.630642 0.776895 0.520292 0.099 Uiso 1 1 calc R U . . .
C10 C 0.7527(5) 0.6339(5) 0.6867(3) 0.0723(9) Uani 1 1 d . . . . .
C11 C 0.7232(5) 0.8075(4) 0.7278(3) 0.0720(9) Uani 1 1 d . . . . .
C12 C 0.7218(8) 0.9112(6) 0.9026(4) 0.1065(15) Uani 1 1 d . . . . .
H12A H 0.777844 1.005363 0.858762 0.160 Uiso 1 1 calc R U . . .
H12B H 0.773109 0.859074 0.987439 0.160 Uiso 1 1 calc R U . . .
H12C H 0.585817 0.973423 0.897609 0.160 Uiso 1 1 calc R U . . .
C13 C 0.8489(6) 0.4440(5) 0.7715(4) 0.0857(11) 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 C11 1.324(4) . ?
O1 C12 1.449(4) . ?
O2 C11 1.193(4) . ?
N1 C13 1.145(5) . ?
C1 C2 1.384(5) . ?
C1 C6 1.389(6) . ?
C1 C7 1.529(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.355(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.616(7) 2_666 ?
C7 C8 1.546(5) . ?
C8 H8 0.9800 . ?
C8 C9 1.486(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.329(5) . ?
C10 C11 1.481(5) . ?
C10 C13 1.430(5) . ?
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
C11 O1 C12 116.1(3) . . ?
C2 C1 C6 117.5(4) . . ?
C2 C1 C7 122.0(3) . . ?
C6 C1 C7 119.4(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C1 C7 H7 109.2 . . ?
C1 C7 C8 117.4(3) . 2_666 ?
C1 C7 C8 119.7(3) . . ?
C8 C7 H7 109.2 2_666 . ?
C8 C7 H7 109.2 . . ?
C8 C7 C8 90.6(3) . 2_666 ?
C7 C8 C7 89.4(3) . 2_666 ?
C7 C8 H8 112.0 2_666 . ?
C7 C8 H8 112.0 . . ?
C9 C8 C7 116.6(3) . . ?
C9 C8 C7 112.9(3) . 2_666 ?
C9 C8 H8 112.0 . . ?
C8 C9 H9 117.7 . . ?
C10 C9 C8 124.5(3) . . ?
C10 C9 H9 117.7 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 C13 120.6(3) . . ?
C13 C10 C11 118.7(3) . . ?
O1 C11 C10 110.6(3) . . ?
O2 C11 O1 124.9(3) . . ?
O2 C11 C10 124.5(3) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C10 178.2(4) . . ?

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
C1 C2 C3 C4 0.9(8) . . . . ?
C1 C7 C8 C7 -122.4(4) . . . 2_666 ?
C1 C7 C8 C9 122.2(4) . . . . ?
C2 C1 C6 C5 1.7(8) . . . . ?
C2 C1 C7 C8 37.7(6) . . . . ?
C2 C1 C7 C8 -70.3(5) . . . 2_666 ?
C2 C3 C4 C5 1.1(9) . . . . ?
C3 C4 C5 C6 -1.7(9) . . . . ?
C4 C5 C6 C1 0.3(9) . . . . ?
C6 C1 C2 C3 -2.3(7) . . . . ?
C6 C1 C7 C8 -154.7(4) . . . . ?
C6 C1 C7 C8 97.3(5) . . . 2_666 ?
C7 C1 C2 C3 165.5(5) . . . . ?
C7 C1 C6 C5 -166.4(5) . . . . ?
C7 C8 C9 C10 85.3(5) 2_666 . . . ?
C7 C8 C9 C10 -173.2(4) . . . . ?
C8 C7 C8 C7 -0.001(1) 2_666 . . 2_666 ?
C8 C7 C8 C9 -115.4(4) 2_666 . . . ?
C8 C9 C10 C11 -159.5(4) . . . . ?
C8 C9 C10 C13 11.9(7) . . . . ?
C9 C10 C11 O1 160.9(4) . . . . ?
C9 C10 C11 O2 -15.9(6) . . . . ?
C12 O1 C11 O2 3.4(6) . . . . ?
C12 O1 C11 C10 -173.3(4) . . . . ?
C13 C10 C11 O1 -10.8(5) . . . . ?
C13 C10 C11 O2 172.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
