# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_20210623NMe
_audit_block_doi                 10.5517/ccdc.csd.cc2cnwyw
_database_code_depnum_ccdc_archive 'CCDC 2194829'
loop_
_audit_author_name
_audit_author_address
'Yousuke Ooyama'
;Hiroshima University
Japan
;
_audit_update_record             
;
2022-08-04 deposited with the CCDC.	2022-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         226.23

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   6.7461(17)
_cell_length_b                   6.8315(18)
_cell_length_c                   21.892(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.503(3)
_cell_angle_gamma                90
_cell_volume                     1007.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4448
_cell_measurement_theta_min      1.8645
_cell_measurement_theta_max      28.5663
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11459
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_full        27.95
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             2397
_reflns_number_gt                1714
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1197
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         2397
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.1886P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2(Bruker AXS)'
_computing_cell_refinement       'APEX3 v2019.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2855(2) 0.5231(2) 0.55497(7) 0.0134(3) Uani d . . . 1 . .
H H1 0.155851 0.513775 0.535662 0.016 Uiso calc U . R 1 . .
C C2 0.4033(2) 0.6888(2) 0.54352(7) 0.0128(3) Uani d . . . 1 . .
C C3 0.6042(2) 0.6984(2) 0.57452(7) 0.0126(3) Uani d . . . 1 . .
C C4 0.6717(2) 0.5563(2) 0.61310(7) 0.0133(3) Uani d . . . 1 . .
H H4 0.800646 0.567359 0.632776 0.016 Uiso calc U . R 1 . .
C C5 0.5520(2) 0.3888(2) 0.62493(7) 0.0115(3) Uani d . . . 1 . .
C C6 0.5075(2) 0.0984(2) 0.67597(7) 0.0124(3) Uani d . . . 1 . .
C C7 0.5800(2) -0.0395(2) 0.71997(7) 0.0147(3) Uani d . . . 1 . .
H H7 0.709228 -0.023594 0.739095 0.018 Uiso calc U . R 1 . .
C C8 0.4663(2) -0.1957(2) 0.73537(7) 0.0159(3) Uani d . . . 1 . .
H H8 0.515351 -0.286109 0.765607 0.019 Uiso calc U . R 1 . .
C C9 0.2768(2) -0.2219(2) 0.70631(7) 0.0164(3) Uani d . . . 1 . .
H H9 0.199326 -0.331562 0.716835 0.02 Uiso calc U . R 1 . .
C C10 0.2009(2) -0.0919(2) 0.66288(7) 0.0147(3) Uani d . . . 1 . .
H H10 0.072107 -0.111467 0.643819 0.018 Uiso calc U . R 1 . .
C C11 0.3159(2) 0.0708(2) 0.64690(7) 0.0119(3) Uani d . . . 1 . .
C C12 0.0546(2) 0.1778(2) 0.57016(7) 0.0169(4) Uani d . . . 1 . .
H H12A -0.051486 0.237208 0.59255 0.025 Uiso calc U . R 1 . .
H H12B 0.030029 0.036983 0.565602 0.025 Uiso calc U . R 1 . .
H H12C 0.057315 0.238145 0.529609 0.025 Uiso calc U . R 1 . .
C C13 0.3538(2) 0.3746(2) 0.59339(7) 0.0115(3) Uani d . . . 1 . .
N N1 0.24707(18) 0.20930(18) 0.60430(6) 0.0116(3) Uani d . . . 1 . .
N N2 0.62454(19) 0.25598(18) 0.66370(6) 0.0137(3) Uani d . . . 1 . .
O O1 0.34732(16) 0.82737(15) 0.50887(5) 0.0178(3) Uani d . . . 1 . .
O O2 0.71587(15) 0.85544(15) 0.56312(5) 0.0171(3) Uani d . . . 1 . .
H H2 0.653296 0.928759 0.537895 0.026 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C13 . 1.379(2) ?
C1 C2 . 1.414(2) ?
C1 H1 . 0.95 ?
C2 O1 . 1.2568(18) ?
C2 C3 . 1.480(2) ?
C3 O2 . 1.3433(17) ?
C3 C4 . 1.348(2) ?
C4 C5 . 1.433(2) ?
C4 H4 . 0.95 ?
C5 N2 . 1.3159(19) ?
C5 C13 . 1.470(2) ?
C6 N2 . 1.3713(19) ?
C6 C7 . 1.413(2) ?
C6 C11 . 1.418(2) ?
C7 C8 . 1.368(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.404(2) ?
C8 H8 . 0.95 ?
C9 C10 . 1.377(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.412(2) ?
C10 H10 . 0.95 ?
C11 N1 . 1.3885(18) ?
C12 N1 . 1.4739(19) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 N1 . 1.3682(19) ?
O2 H2 . 0.84 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 C1 C2 . . 121.77(14) ?
C13 C1 H1 . . 119.1 ?
C2 C1 H1 . . 119.1 ?
O1 C2 C1 . . 123.97(14) ?
O1 C2 C3 . . 118.45(13) ?
C1 C2 C3 . . 117.58(13) ?
O2 C3 C4 . . 121.33(13) ?
O2 C3 C2 . . 117.30(13) ?
C4 C3 C2 . . 121.37(13) ?
C3 C4 C5 . . 121.07(13) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
N2 C5 C4 . . 118.42(13) ?
N2 C5 C13 . . 123.31(13) ?
C4 C5 C13 . . 118.27(13) ?
N2 C6 C7 . . 118.52(13) ?
N2 C6 C11 . . 122.44(13) ?
C7 C6 C11 . . 119.03(14) ?
C8 C7 C6 . . 120.79(14) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C9 . . 119.76(14) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C10 C9 C8 . . 121.38(14) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 119.48(14) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
N1 C11 C10 . . 122.45(13) ?
N1 C11 C6 . . 117.98(13) ?
C10 C11 C6 . . 119.56(14) ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C13 C1 . . 123.64(13) ?
N1 C13 C5 . . 116.45(13) ?
C1 C13 C5 . . 119.91(13) ?
C13 N1 C11 . . 121.46(12) ?
C13 N1 C12 . . 119.25(12) ?
C11 N1 C12 . . 119.29(12) ?
C5 N2 C6 . . 118.15(13) ?
C3 O2 H2 . . 109.5 ?

####################################################################### 
# 
# 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_20210621NMeOMOM
_audit_block_doi                 10.5517/ccdc.csd.cc2cnx0z
_database_code_depnum_ccdc_archive 'CCDC 2194831'
loop_
_audit_author_name
_audit_author_address
'Yousuke Ooyama'
;Hiroshima University
Japan
;
_audit_update_record             
;
2022-08-04 deposited with the CCDC.	2022-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         270.28

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8605(18)
_cell_length_b                   11.1311(18)
_cell_length_c                   10.3566(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.649(2)
_cell_angle_gamma                90
_cell_volume                     1243.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6956
_cell_measurement_theta_min      1.8896
_cell_measurement_theta_max      28.4950
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14509
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_full        27.97
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2984
_reflns_number_gt                2449
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1037
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_number_reflns         2984
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+0.6753P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2(Bruker AXS)'
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.38995(11) 0.66863(11) 0.62041(12) 0.0130(3) Uani d . . . 1 . .
H H1 0.423155 0.73397 0.67226 0.016 Uiso calc U . R 1 . .
C C2 0.41643(11) 0.54834(12) 0.66458(12) 0.0141(3) Uani d . . . 1 . .
C C3 0.36702(11) 0.44917(11) 0.57739(12) 0.0138(3) Uani d . . . 1 . .
C C4 0.29722(12) 0.47164(11) 0.46365(12) 0.0139(3) Uani d . . . 1 . .
H H4 0.267471 0.406456 0.409582 0.017 Uiso calc U . R 1 . .
C C5 0.26705(11) 0.59270(11) 0.42283(12) 0.0119(3) Uani d . . . 1 . .
C C6 0.15646(11) 0.72255(11) 0.27984(12) 0.0128(3) Uani d . . . 1 . .
C C7 0.07120(12) 0.73847(12) 0.16755(12) 0.0148(3) Uani d . . . 1 . .
H H7 0.04053 0.670383 0.118677 0.018 Uiso calc U . R 1 . .
C C8 0.03216(12) 0.85134(13) 0.12825(13) 0.0178(3) Uani d . . . 1 . .
H H8 -0.024609 0.861584 0.052099 0.021 Uiso calc U . R 1 . .
C C9 0.07678(12) 0.95130(12) 0.20146(13) 0.0178(3) Uani d . . . 1 . .
H H9 0.049095 1.029222 0.174246 0.021 Uiso calc U . R 1 . .
C C10 0.15982(12) 0.93958(12) 0.31199(13) 0.0157(3) Uani d . . . 1 . .
H H10 0.188185 1.008549 0.36066 0.019 Uiso calc U . R 1 . .
C C11 0.20234(11) 0.82398(11) 0.35217(12) 0.0123(3) Uani d . . . 1 . .
C C12 0.34306(13) 0.91039(11) 0.53165(12) 0.0164(3) Uani d . . . 1 . .
H H12A 0.360256 0.973261 0.469954 0.025 Uiso calc U . R 1 . .
H H12B 0.420533 0.886472 0.583266 0.025 Uiso calc U . R 1 . .
H H12C 0.28508 0.941179 0.5895 0.025 Uiso calc U . R 1 . .
C C13 0.31803(11) 0.69207(11) 0.50541(12) 0.0115(2) Uani d . . . 1 . .
C C14 0.36036(12) 0.23639(12) 0.54738(14) 0.0180(3) Uani d . . . 1 . .
H H14A 0.391757 0.245833 0.461945 0.022 Uiso calc U . R 1 . .
H H14B 0.398905 0.163367 0.589033 0.022 Uiso calc U . R 1 . .
C C15 0.17951(14) 0.19258(13) 0.64408(14) 0.0239(3) Uani d . . . 1 . .
H H15A 0.218249 0.119619 0.683072 0.036 Uiso calc U . R 1 . .
H H15B 0.090155 0.179491 0.623533 0.036 Uiso calc U . R 1 . .
H H15C 0.193896 0.259457 0.705516 0.036 Uiso calc U . R 1 . .
N N1 0.28820(10) 0.80607(9) 0.46016(10) 0.0124(2) Uani d . . . 1 . .
N N2 0.19229(10) 0.60729(9) 0.31538(10) 0.0132(2) Uani d . . . 1 . .
O O1 0.47612(9) 0.52518(9) 0.77128(9) 0.0202(2) Uani d . . . 1 . .
O O2 0.39782(9) 0.33879(8) 0.62692(9) 0.0178(2) Uani d . . . 1 . .
O O3 0.23226(9) 0.22051(8) 0.52772(9) 0.0181(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C13 . 1.3716(17) ?
C1 C2 . 1.4332(17) ?
C1 H1 . 0.95 ?
C2 O1 . 1.2418(16) ?
C2 C3 . 1.4864(18) ?
C3 C4 . 1.3483(18) ?
C3 O2 . 1.3582(15) ?
C4 C5 . 1.4387(17) ?
C4 H4 . 0.95 ?
C5 N2 . 1.3095(16) ?
C5 C13 . 1.4669(17) ?
C6 N2 . 1.3782(16) ?
C6 C7 . 1.4113(17) ?
C6 C11 . 1.4134(17) ?
C7 C8 . 1.3726(18) ?
C7 H7 . 0.95 ?
C8 C9 . 1.4010(19) ?
C8 H8 . 0.95 ?
C9 C10 . 1.3790(18) ?
C9 H9 . 0.95 ?
C10 C11 . 1.4133(17) ?
C10 H10 . 0.95 ?
C11 N1 . 1.3852(16) ?
C12 N1 . 1.4661(15) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 N1 . 1.3783(16) ?
C14 O3 . 1.3938(16) ?
C14 O2 . 1.4373(16) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 O3 . 1.4272(17) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 C1 C2 . . 121.86(11) ?
C13 C1 H1 . . 119.1 ?
C2 C1 H1 . . 119.1 ?
O1 C2 C1 . . 122.87(12) ?
O1 C2 C3 . . 120.06(12) ?
C1 C2 C3 . . 117.06(11) ?
C4 C3 O2 . . 125.92(12) ?
C4 C3 C2 . . 121.32(11) ?
O2 C3 C2 . . 112.74(11) ?
C3 C4 C5 . . 121.08(12) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
N2 C5 C4 . . 117.62(11) ?
N2 C5 C13 . . 123.85(11) ?
C4 C5 C13 . . 118.50(11) ?
N2 C6 C7 . . 118.36(11) ?
N2 C6 C11 . . 122.06(11) ?
C7 C6 C11 . . 119.59(11) ?
C8 C7 C6 . . 120.66(12) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C9 . . 119.40(12) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
C10 C9 C8 . . 121.74(12) ?
C10 C9 H9 . . 119.1 ?
C8 C9 H9 . . 119.1 ?
C9 C10 C11 . . 119.38(12) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
N1 C11 C10 . . 122.36(11) ?
N1 C11 C6 . . 118.43(11) ?
C10 C11 C6 . . 119.22(11) ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C1 C13 N1 . . 123.93(11) ?
C1 C13 C5 . . 120.09(11) ?
N1 C13 C5 . . 115.98(11) ?
O3 C14 O2 . . 113.31(11) ?
O3 C14 H14A . . 108.9 ?
O2 C14 H14A . . 108.9 ?
O3 C14 H14B . . 108.9 ?
O2 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C13 N1 C11 . . 121.12(10) ?
C13 N1 C12 . . 119.45(10) ?
C11 N1 C12 . . 119.34(10) ?
C5 N2 C6 . . 118.07(11) ?
C3 O2 C14 . . 117.39(10) ?
C14 O3 C15 . . 113.31(11) ?

####################################################################### 
# 
# 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_20210603NMeBenzoyl_cif
_audit_block_doi                 10.5517/ccdc.csd.cc2cnx10
_database_code_depnum_ccdc_archive 'CCDC 2194832'
loop_
_audit_author_name
_audit_author_address
'Yousuke Ooyama'
;Hiroshima University
Japan
;
_audit_update_record             
;
2022-08-04 deposited with the CCDC.	2022-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 Cl N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         364.77

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9125(8)
_cell_length_b                   17.0395(10)
_cell_length_c                   7.2712(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.9830(10)
_cell_angle_gamma                90
_cell_volume                     1595.96(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12633
_cell_measurement_theta_min      1.9387
_cell_measurement_theta_max      28.9899
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear red'
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18708
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             3827
_reflns_number_gt                3316
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0935
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_number_reflns         3827
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.6591P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.281
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       'APEX2(Bruker AXS)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.34440(9) 0.49893(7) 0.78326(17) 0.0195(2) Uani d . . . 1 . .
C C3 0.24368(9) 0.50811(7) 0.67450(17) 0.0193(2) Uani d . . . 1 . .
C C4 0.20355(9) 0.57764(8) 0.62382(17) 0.0203(3) Uani d . . . 1 . .
H H3 0.137246 0.580282 0.558782 0.024 Uiso calc U . R 1 . .
C C5 0.26052(9) 0.64870(7) 0.66746(16) 0.0178(2) Uani d . . . 1 . .
C C6 0.26865(10) 0.78347(7) 0.67377(17) 0.0193(2) Uani d . . . 1 . .
C C7 0.21696(10) 0.85566(8) 0.64429(18) 0.0235(3) Uani d . . . 1 . .
H H6 0.147785 0.856275 0.590473 0.028 Uiso calc U . R 1 . .
C C8 0.26530(11) 0.92496(8) 0.69235(19) 0.0263(3) Uani d . . . 1 . .
H H7 0.229789 0.973397 0.672924 0.032 Uiso calc U . R 1 . .
C C9 0.36790(11) 0.92377(8) 0.77065(19) 0.0257(3) Uani d . . . 1 . .
H H8 0.401137 0.971877 0.804635 0.031 Uiso calc U . R 1 . .
C C10 0.42131(10) 0.85442(8) 0.79918(18) 0.0226(3) Uani d . . . 1 . .
H H9 0.490855 0.855042 0.851202 0.027 Uiso calc U . R 1 . .
C C11 0.37281(9) 0.78258(7) 0.75124(16) 0.0185(2) Uani d . . . 1 . .
C C12 0.53078(9) 0.70425(8) 0.84159(18) 0.0226(3) Uani d . . . 1 . .
H H11A 0.537015 0.688574 0.971557 0.034 Uiso calc U . R 1 . .
H H11B 0.564386 0.755282 0.827788 0.034 Uiso calc U . R 1 . .
H H11C 0.564512 0.664948 0.767579 0.034 Uiso calc U . R 1 . .
C C13 0.36584(9) 0.64104(7) 0.75428(16) 0.0170(2) Uani d . . . 1 . .
C C1 0.40532(9) 0.56914(7) 0.80781(17) 0.0189(2) Uani d . . . 1 . .
H H13 0.474246 0.565767 0.862108 0.023 Uiso calc U . R 1 . .
C C14 0.22877(10) 0.38215(8) 0.54702(17) 0.0212(3) Uani d . . . 1 . .
C C15 0.17217(9) 0.30726(8) 0.56379(16) 0.0189(2) Uani d . . . 1 . .
C C16 0.07418(9) 0.30318(7) 0.63428(16) 0.0188(2) Uani d . . . 1 . .
H H16 0.039187 0.349996 0.664486 0.023 Uiso calc U . R 1 . .
C C17 0.02811(9) 0.23081(8) 0.66008(17) 0.0199(2) Uani d . . . 1 . .
H H17 -0.039218 0.227372 0.704505 0.024 Uiso calc U . R 1 . .
C C18 0.08275(10) 0.16353(7) 0.61941(17) 0.0202(3) Uani d . . . 1 . .
C C19 0.17908(10) 0.16620(8) 0.54572(17) 0.0211(3) Uani d . . . 1 . .
H H19 0.214304 0.119312 0.516889 0.025 Uiso calc U . R 1 . .
C C20 0.22231(9) 0.23872(8) 0.51544(16) 0.0199(3) Uani d . . . 1 . .
H H20 0.286972 0.241906 0.46103 0.024 Uiso calc U . R 1 . .
Cl Cl1 0.02881(3) 0.07231(2) 0.66204(5) 0.03044(11) Uani d . . . 1 . .
N N1 0.42080(8) 0.71017(6) 0.77855(14) 0.0182(2) Uani d . . . 1 . .
N N2 0.21523(8) 0.71570(6) 0.62730(14) 0.0197(2) Uani d . . . 1 . .
O O1 0.37016(7) 0.43415(5) 0.85015(13) 0.0245(2) Uani d . . . 1 . .
O O2 0.18432(7) 0.44071(5) 0.64333(13) 0.0216(2) Uani d . . . 1 . .
O O3 0.30449(7) 0.39197(6) 0.46202(13) 0.0289(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2 O1 . 1.2422(15) ?
C2 C1 . 1.4360(17) ?
C2 C3 . 1.4827(17) ?
C3 C4 . 1.3347(18) ?
C3 O2 . 1.3906(15) ?
C4 C5 . 1.4406(17) ?
C5 N2 . 1.3064(16) ?
C5 C13 . 1.4648(16) ?
C6 N2 . 1.3752(16) ?
C6 C7 . 1.4088(17) ?
C6 C11 . 1.4216(17) ?
C7 C8 . 1.3696(19) ?
C8 C9 . 1.405(2) ?
C9 C10 . 1.3766(19) ?
C10 C11 . 1.4078(18) ?
C11 N1 . 1.3887(16) ?
C12 N1 . 1.4652(15) ?
C13 C1 . 1.3729(17) ?
C13 N1 . 1.3802(15) ?
C14 O3 . 1.2042(15) ?
C14 O2 . 1.3680(15) ?
C14 C15 . 1.4797(18) ?
C15 C20 . 1.3922(18) ?
C15 C16 . 1.3995(17) ?
C16 C17 . 1.3876(18) ?
C17 C18 . 1.3889(18) ?
C18 C19 . 1.3889(18) ?
C18 Cl1 . 1.7399(13) ?
C19 C20 . 1.3797(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C2 C1 . . 124.20(11) ?
O1 C2 C3 . . 120.24(11) ?
C1 C2 C3 . . 115.53(11) ?
C4 C3 O2 . . 119.29(11) ?
C4 C3 C2 . . 123.38(11) ?
O2 C3 C2 . . 116.93(11) ?
C3 C4 C5 . . 120.19(11) ?
N2 C5 C4 . . 118.13(11) ?
N2 C5 C13 . . 124.19(11) ?
C4 C5 C13 . . 117.68(11) ?
N2 C6 C7 . . 118.13(11) ?
N2 C6 C11 . . 122.21(11) ?
C7 C6 C11 . . 119.66(12) ?
C8 C7 C6 . . 120.75(12) ?
C7 C8 C9 . . 119.41(12) ?
C10 C9 C8 . . 121.45(13) ?
C9 C10 C11 . . 119.97(12) ?
N1 C11 C10 . . 123.42(11) ?
N1 C11 C6 . . 117.82(11) ?
C10 C11 C6 . . 118.76(11) ?
C1 C13 N1 . . 123.22(11) ?
C1 C13 C5 . . 121.13(11) ?
N1 C13 C5 . . 115.65(10) ?
C13 C1 C2 . . 121.25(11) ?
O3 C14 O2 . . 123.08(12) ?
O3 C14 C15 . . 125.83(12) ?
O2 C14 C15 . . 111.08(10) ?
C20 C15 C16 . . 119.93(12) ?
C20 C15 C14 . . 117.49(11) ?
C16 C15 C14 . . 122.49(11) ?
C17 C16 C15 . . 120.04(11) ?
C16 C17 C18 . . 118.42(11) ?
C19 C18 C17 . . 122.47(12) ?
C19 C18 Cl1 . . 118.58(10) ?
C17 C18 Cl1 . . 118.94(10) ?
C20 C19 C18 . . 118.30(12) ?
C19 C20 C15 . . 120.70(11) ?
C13 N1 C11 . . 121.30(10) ?
C13 N1 C12 . . 117.38(10) ?
C11 N1 C12 . . 121.27(10) ?
C5 N2 C6 . . 118.02(10) ?
C14 O2 C3 . . 116.09(10) ?

