# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_220830_c146_1
_database_code_depnum_ccdc_archive 'CCDC 2305891'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 N O'
_chemical_formula_sum            'C9 H6 N O'
_chemical_formula_weight         144.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 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 0.0181 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      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                   9.4411(4)
_cell_length_b                   6.1954(3)
_cell_length_c                   11.6634(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.836(4)
_cell_angle_gamma                90
_cell_volume                     681.86(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2345
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3270
_cell_measurement_theta_min      5.9380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -1 6 0.1430
-2 -4 1 0.0639
-3 1 -6 0.1008
2 4 0 0.0737
5 -1 -4 0.0205
-5 1 5 0.0204

_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.051
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.3437 -0.5266 6.1320 0.0690 0.2855 0.9559
-1.9794 -3.7975 0.5061 0.2224 0.9281 -0.2988
-3.3249 0.5627 -6.1369 -0.0711 -0.2944 -0.9530
2.4461 3.6766 0.3975 -0.2097 -0.8755 0.4353
5.1046 -0.7454 -4.1511 -0.9882 0.1298 0.0818
-4.7787 0.8034 4.6828 0.9914 -0.1303 0.0088

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6327
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.168
_diffrn_reflns_theta_min         5.938
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -23.00   0.50    0.05    --  -42.93 -52.00 122.00  180
  2  ω    -19.00  31.00   0.50    0.05    --  -42.93  52.00 -92.00  100
  3  ω     26.00  68.00   0.50    0.05    --   42.93  52.00 -92.00   84
  4  ω     34.00  60.00   0.50    0.07    --   76.50 -52.00 122.00   52
  5  ω     75.00 101.00   0.50    0.07    --   76.50  52.00 -92.00   52
  6  ω    125.00 151.00   0.50    0.07    --   76.50  52.00 -92.00   52
  7  ω   -124.00 -33.00   0.50    0.07    -- -106.00  52.00 -92.00  182
  8  ω   -176.00 -86.00   0.50    0.07    -- -106.00 -52.00 122.00  180
  9  ω   -116.00 -70.00   0.50    0.05    --  -42.93-125.00  90.00   92
 10  ω    -92.00 -14.00   0.50    0.05    --  -42.93 125.00 -90.00  156
 11  ω     11.00  37.00   0.50    0.05    --   42.93 -52.00 122.00   52
 12  ω     86.00 111.00   0.50    0.05    --   42.93 125.00  90.00   50
 13  ω     15.00  64.00   0.50    0.07    --   76.50 -77.00 -30.00   98
 14  ω     73.00  99.00   0.50    0.07    --   76.50 -77.00 -30.00   52
 15  ω   -116.00 -81.00   0.50    0.07    -- -106.00 125.00 120.00   70
 16  ω   -131.00 -26.00   0.50    0.07    -- -106.00  19.00 120.00  210
 17  ω    -73.00 -33.00   0.50    0.07    -- -106.00  57.00 120.00   80
 18  ω   -112.00 -87.00   0.50    0.07    -- -106.00 125.00  60.00   50
 19  ω    -85.00 -58.00   0.50    0.07    -- -106.00 125.00  60.00   54
 20  ω   -122.00 -36.00   0.50    0.07    -- -106.00  77.00 -30.00  172
 21  ω   -172.00-122.00   0.50    0.07    -- -106.00 -19.00  30.00  100
 22  ω   -112.00 -83.00   0.50    0.07    -- -106.00 -19.00  30.00   58
 23  ω   -173.00-127.00   0.50    0.07    -- -106.00-125.00 -60.00   92
 24  ω    -72.00 -34.00   0.50    0.07    -- -106.00 125.00 -90.00   76
 25  ω   -139.00 -95.00   0.50    0.07    -- -106.00 -99.00   0.00   88
 26  ω   -177.00-146.00   0.50    0.07    -- -106.00 -99.00   0.00   62
 27  ω    -73.00 -36.00   0.50    0.07    -- -106.00 125.00 120.00   74
 28  ω   -112.00 -70.00   0.50    0.07    -- -106.00-125.00 -60.00   84
 29  ω   -112.00 -86.00   0.50    0.07    -- -106.00 125.00 -60.00   52
 30  ω    -68.00 -39.00   0.50    0.07    -- -106.00 125.00 -60.00   58
 31  ω    -99.00 -63.00   0.50    0.07    -- -106.00 125.00 150.00   72
 32  ω   -115.00 -84.00   0.50    0.07    -- -106.00 125.00 -90.00   62
 33  ω    -88.00 -62.00   0.50    0.07    -- -106.00 125.00 -30.00   52
 34  ω   -125.00 -89.00   0.50    0.07    -- -106.00  57.00 120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1251613000
_diffrn_orient_matrix_UB_12      0.0174726000
_diffrn_orient_matrix_UB_13      0.0809978000
_diffrn_orient_matrix_UB_21      0.0071812000
_diffrn_orient_matrix_UB_22      -0.2452498000
_diffrn_orient_matrix_UB_23      0.0215876000
_diffrn_orient_matrix_UB_31      0.1045695000
_diffrn_orient_matrix_UB_32      0.0377770000
_diffrn_orient_matrix_UB_33      0.1021073000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1187
_reflns_number_total             1361
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.069
_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)+(0.0521P)²+0.1361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1116
_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:
 C2(H2), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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
O10 O 0.45023(10) 0.70855(17) 0.65918(8) 0.0453(3) Uani 1 1 d . . . . .
N7 N 0.57527(12) 1.02061(19) 0.61096(9) 0.0423(3) Uani 1 1 d . . . . .
C1 C 0.32363(14) 0.6509(2) 0.48853(12) 0.0408(3) Uani 1 1 d . . . . .
C8 C 0.59080(14) 1.1583(2) 0.52267(11) 0.0394(3) Uani 1 1 d . . . . .
C9 C 0.48392(14) 0.8674(2) 0.58292(11) 0.0397(3) Uani 1 1 d . . . . .
C6 C 0.35204(15) 0.5784(2) 0.60001(12) 0.0422(3) Uani 1 1 d . . . . .
C2 C 0.22850(16) 0.5364(2) 0.41747(12) 0.0452(4) Uani 1 1 d . . . . .
H2 H 0.208718 0.582256 0.342730 0.054 Uiso 1 1 calc R . . . .
C3 C 0.16398(16) 0.3535(2) 0.45997(13) 0.0477(4) Uani 1 1 d . . . . .
C4 C 0.19411(17) 0.2893(3) 0.57341(13) 0.0510(4) Uani 1 1 d . . . . .
H4 H 0.148751 0.167828 0.601404 0.061 Uiso 1 1 calc R . . . .
C5 C 0.28856(17) 0.3991(3) 0.64554(13) 0.0494(4) Uani 1 1 d . . . . .
H5 H 0.308025 0.354205 0.720488 0.059 Uiso 1 1 calc R . . . .
C11 C 0.0621(2) 0.2227(3) 0.38548(15) 0.0625(5) Uani 1 1 d . . . . .
H11A H 0.054791 0.285612 0.310304 0.094 Uiso 1 1 calc GR . . . .
H11B H -0.029497 0.222167 0.418933 0.094 Uiso 1 1 calc GR . . . .
H11C H 0.096252 0.077257 0.379877 0.094 Uiso 1 1 calc GR . . . .


_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
O10 C9 1.3707(16) . ?
O10 C6 1.3944(17) . ?
N7 C8 1.3490(17) . ?
N7 C9 1.3167(18) . ?
C1 C8 1.4398(19) 3_676 ?
C1 C6 1.3935(19) . ?
C1 C2 1.3960(19) . ?
C8 C9 1.4086(19) 3_676 ?
C6 C5 1.377(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(2) . ?
C3 C4 1.402(2) . ?
C3 C11 1.511(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C9 O10 C6 104.97(10) . . ?
C9 N7 C8 110.66(12) . . ?
C6 C1 C8 104.91(12) . 3_676 ?
C6 C1 C2 119.42(13) . . ?
C2 C1 C8 135.67(13) . 3_676 ?
N7 C8 C1 131.57(12) . 3_676 ?
N7 C8 C9 122.15(12) . 3_676 ?
C9 C8 C1 106.28(12) 3_676 3_676 ?
O10 C9 C8 111.46(12) . 3_676 ?
N7 C9 O10 121.35(12) . . ?
N7 C9 C8 127.19(13) . 3_676 ?
C1 C6 O10 112.36(12) . . ?
C5 C6 O10 124.50(13) . . ?
C5 C6 C1 123.14(13) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.00(13) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.43(14) . . ?
C2 C3 C11 120.78(14) . . ?
C4 C3 C11 119.79(14) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 C3 122.76(14) . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 116.23(14) . . ?
C6 C5 H5 121.9 . . ?
C4 C5 H5 121.9 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_220818_c2_1
_database_code_depnum_ccdc_archive 'CCDC 2305892'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 N O'
_chemical_formula_sum            'C10 H8 N O'
_chemical_formula_weight         158.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16 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 0.0181 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      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                   10.5642(4)
_cell_length_b                   4.6703(2)
_cell_length_c                   16.2364(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.796(4)
_cell_angle_gamma                90
_cell_volume                     770.82(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2335
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8230
_cell_measurement_theta_min      4.5030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 9 0.0644
5 0 -9 0.0568
1 3 -3 0.3926
6 0 3 0.0426
-2 -3 3 0.2948
6 0 -8 0.0211
-7 0 2 0.1115
2 0 -11 0.0679
-4 0 -6 0.1169

_exptl_crystal_size_max          0.756
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.119
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.5425 0.0723 9.4910 0.2204 0.9197 -0.3249
4.5423 -0.0411 -9.4941 -0.2196 -0.9164 0.3346
1.4719 2.8433 -3.4137 0.0007 0.0002 1.0000
5.6011 0.0570 3.4996 -0.9909 0.1302 0.0347
-1.8007 -2.8359 3.1917 0.0585 -0.0079 -0.9983
5.8614 -0.2245 -7.6534 -0.5051 -0.8247 0.2545
-6.8388 -0.0418 2.1898 0.9035 0.3746 -0.2085
2.1879 -0.1197 -10.5177 0.1746 -0.9406 0.2911
-4.0410 -0.1324 -6.4892 0.9014 -0.4296 0.0540

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.123
_diffrn_reflns_theta_min         4.498
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  18.00   0.50    0.05    --  -42.93  27.00 -18.00  170
  2  ω     -3.00  31.00   0.50    0.05    --  -42.93  57.00-180.00   68
  3  ω     81.00 120.00   0.50    0.05    --   42.93  27.00 -18.00   78
  4  ω    108.00 156.00   0.50    0.07    --   76.50  27.00 -18.00   96
  5  ω     26.00  51.00   0.50    0.07    --   76.50 -27.00 178.00   50
  6  ω     -7.00  19.00   0.50    0.05    --   42.93 -27.00 178.00   52
  7  ω    -77.00 -52.00   0.50    0.05    --  -42.93 -27.00 178.00   50
  8  ω    -88.00 -34.00   0.50    0.07    -- -106.00  57.00 120.00  108
  9  ω    -83.00 -57.00   0.50    0.07    -- -106.00 125.00  60.00   52
 10  ω   -105.00 -65.00   0.50    0.07    -- -106.00  57.00 -30.00   80
 11  ω    -57.00 -32.00   0.50    0.07    -- -106.00  57.00 -30.00   50
 12  ω    -66.00  -6.00   0.50    0.05    --  -42.93  57.00-180.00  120
 13  ω   -109.00 -84.00   0.50    0.07    -- -106.00 -57.00  60.00   50
 14  ω   -140.00-114.00   0.50    0.07    -- -106.00 -27.00 178.00   52
 15  ω   -117.00 -29.00   0.50    0.07    -- -106.00  37.00  90.00  176
 16  ω    -92.00 -52.00   0.50    0.07    -- -106.00  77.00 150.00   80
 17  ω   -127.00-102.00   0.50    0.07    -- -106.00  77.00 150.00   50
 18  ω   -125.00 -92.00   0.50    0.07    -- -106.00  57.00 120.00   66
 19  ω   -131.00 -38.00   0.50    0.07    -- -106.00  27.00 -18.00  186
 20  ω   -142.00-116.00   0.50    0.07    -- -106.00 -57.00 -30.00   52
 21  ω   -174.00-125.00   0.50    0.07    -- -106.00 -57.00  60.00   98
 22  ω   -175.00-150.00   0.50    0.07    -- -106.00 -57.00 -30.00   50
 23  ω   -161.00 -86.00   0.50    0.07    -- -106.00 -57.00-180.00  150
 24  ω     46.00  71.00   0.50    0.05    --   42.93-125.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1474333000
_diffrn_orient_matrix_UB_12      0.0195352000
_diffrn_orient_matrix_UB_13      -0.0474932000
_diffrn_orient_matrix_UB_21      -0.0291892000
_diffrn_orient_matrix_UB_22      0.1136984000
_diffrn_orient_matrix_UB_23      0.0820667000
_diffrn_orient_matrix_UB_31      0.0199383000
_diffrn_orient_matrix_UB_32      0.3089092000
_diffrn_orient_matrix_UB_33      -0.0270446000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1365
_reflns_number_total             1546
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.065
_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)+(0.0814P)²+0.1097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
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
O10 O 0.29998(10) 0.3255(2) 0.50977(7) 0.0485(3) Uani 1 1 d . . . . .
N7 N 0.37868(11) -0.0175(3) 0.43057(7) 0.0434(3) Uani 1 1 d . . . . .
C8 C 0.51276(13) 0.1722(3) 0.56676(9) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.39711(13) 0.1484(3) 0.49814(9) 0.0414(4) Uani 1 1 d . . . . .
C1 C 0.48440(13) 0.3799(3) 0.62473(9) 0.0415(4) Uani 1 1 d . . . . .
C2 C 0.55301(14) 0.5006(3) 0.70303(9) 0.0442(4) Uani 1 1 d . . . . .
H2 H 0.639380 0.446592 0.729075 0.053 Uiso 1 1 calc R . . . .
C6 C 0.35467(14) 0.4651(3) 0.58681(9) 0.0439(4) Uani 1 1 d . . . . .
C3 C 0.49074(15) 0.7018(3) 0.74143(9) 0.0460(4) Uani 1 1 d . . . . .
C4 C 0.36099(16) 0.7808(4) 0.70063(10) 0.0508(4) Uani 1 1 d . . . . .
H4 H 0.320320 0.916520 0.726715 0.061 Uiso 1 1 calc R . . . .
C5 C 0.29060(16) 0.6656(3) 0.62311(10) 0.0509(4) Uani 1 1 d . . . . .
H5 H 0.204461 0.720754 0.596865 0.061 Uiso 1 1 calc R . . . .
C11 C 0.55964(17) 0.8331(4) 0.82713(10) 0.0553(4) Uani 1 1 d . . . . .
H11A H 0.653942 0.812444 0.836896 0.066 Uiso 1 1 calc R . . . .
H11B H 0.539876 1.036149 0.825539 0.066 Uiso 1 1 calc R . . . .
C12 C 0.5197(2) 0.6980(5) 0.90054(11) 0.0688(6) Uani 1 1 d . . . . .
H12A H 0.425462 0.696102 0.887969 0.103 Uiso 1 1 calc GR . . . .
H12B H 0.555752 0.806670 0.951753 0.103 Uiso 1 1 calc GR . . . .
H12C H 0.552325 0.505343 0.908657 0.103 Uiso 1 1 calc GR . . . .


_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
O10 C9 1.3705(17) . ?
O10 C6 1.3892(17) . ?
N7 C8 1.3461(18) 3_656 ?
N7 C9 1.3138(18) . ?
C8 C9 1.416(2) . ?
C8 C1 1.439(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.399(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(2) . ?
C6 C5 1.378(2) . ?
C3 C4 1.400(2) . ?
C3 C11 1.513(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.507(2) . ?
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
C9 O10 C6 105.29(11) . . ?
C9 N7 C8 111.00(12) . 3_656 ?
N7 C8 C9 121.89(13) 3_656 . ?
N7 C8 C1 131.91(13) 3_656 . ?
C9 C8 C1 106.20(12) . . ?
O10 C9 C8 111.24(12) . . ?
N7 C9 O10 121.65(12) . . ?
N7 C9 C8 127.11(13) . . ?
C2 C1 C8 135.84(14) . . ?
C6 C1 C8 104.91(12) . . ?
C6 C1 C2 119.25(14) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.28(14) . . ?
C3 C2 H2 120.4 . . ?
O10 C6 C1 112.36(13) . . ?
C5 C6 O10 124.86(13) . . ?
C5 C6 C1 122.78(14) . . ?
C2 C3 C4 119.24(14) . . ?
C2 C3 C11 121.27(14) . . ?
C4 C3 C11 119.48(14) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 C3 122.83(15) . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 116.61(14) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C3 C11 H11A 109.0 . . ?
C3 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C3 112.92(14) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_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 2.279
_oxdiff_exptl_absorpt_empirical_full_min 0.261
####################################################################### 
# 
# 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_221031_c106_2
_database_code_depnum_ccdc_archive 'CCDC 2305894'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 N O'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H20 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 0.0181 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      monoclinic
_space_group_IT_number           14
_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                   4.74760(10)
_cell_length_b                   8.2212(2)
_cell_length_c                   22.6292(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.392(2)
_cell_angle_gamma                90
_cell_volume                     882.47(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3098
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2650
_cell_measurement_theta_min      5.7170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -3 11 0.0041
0 -2 -13 0.0094
3 1 -2 0.3431
0 5 -3 0.0074
0 -5 3 0.0334

_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.8361 -3.3805 10.8006 0.2097 0.8737 0.4390
0.0964 -2.4822 -13.0029 0.8376 -0.5131 -0.1874
3.0533 0.6156 -1.6511 -0.1262 0.0769 -0.9890
-0.2214 5.2378 -2.5601 -0.7602 -0.6496 -0.0089
0.0536 -5.2402 2.7515 0.7587 0.6483 0.0643

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6364
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.326
_diffrn_reflns_theta_min         3.910
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00   6.00   0.50    0.38    --   42.93 -57.00 -60.00   64
  2  ω     11.00  65.00   0.50    0.38    --   42.93 -57.00 -60.00  108
  3  ω     74.00 117.00   0.50    0.38    --   42.93 125.00 150.00   86
  4  ω     65.00  90.00   0.50    0.38    --   42.93 135.00  50.00   50
  5  ω     83.00 108.00   0.50    1.50    --   76.50 135.00  50.00   50
  6  ω     84.00 109.00   0.50    1.50    --   76.50 134.00-129.00   50
  7  ω     71.00 106.00   0.50    0.38    --   42.93 125.00-180.00   70
  8  ω    -60.00 -34.00   0.50    0.38    --  -42.93 134.00-129.00   52
  9  ω    -82.00 -57.00   0.50    1.50    -- -106.00 134.00-129.00   50
 10  ω    -99.00 -55.00   0.50    1.50    -- -106.00  57.00 -30.00   88
 11  ω    -70.00 -44.00   0.50    1.50    -- -106.00  57.00 -90.00   52
 12  ω    -83.00 -38.00   0.50    1.50    -- -106.00  37.00 -60.00   90
 13  ω   -106.00 -56.00   0.50    1.50    -- -106.00 125.00  30.00  100
 14  ω    -85.00 -60.00   0.50    1.50    -- -106.00 125.00  90.00   50
 15  ω   -102.00 -77.00   0.50    1.50    -- -106.00 135.00  50.00   50
 16  ω   -115.00 -90.00   0.50    1.50    -- -106.00 125.00  90.00   50
 17  ω   -132.00 -81.00   0.50    1.50    -- -106.00  77.00  30.00  102
 18  ω    -89.00 -50.00   0.50    0.38    --  -42.93 135.00  50.00   78
 19  ω   -135.00 -61.00   0.50    1.50    -- -106.00  77.00-120.00  148
 20  ω   -118.00 -93.00   0.50    1.50    -- -106.00  77.00-150.00   50
 21  ω   -170.00-144.00   0.50    1.50    -- -106.00 -37.00   0.00   52
 22  ω   -120.00 -87.00   0.50    1.50    -- -106.00 -37.00   0.00   66
 23  ω   -133.00-107.00   0.50    1.50    -- -106.00 -99.00 -90.00   52
 24  ω   -149.00-124.00   0.50    1.50    -- -106.00-135.00 -15.00   50
 25  ω   -146.00 -79.00   0.50    1.50    -- -106.00 -77.00  60.00  134
 26  ω   -116.00 -66.00   0.50    0.38    --  -42.93-135.00 -15.00  100
 27  ω   -138.00-113.00   0.50    1.50    -- -106.00-134.00 163.00   50
 28  ω   -173.00 -75.00   0.50    1.50    -- -106.00 -19.00  90.00  196
 29  ω   -113.00 -76.00   0.50    1.50    -- -106.00 -19.00 150.00   74
 30  ω   -149.00-102.00   0.50    1.50    -- -106.00 -57.00 -60.00   94
 31  ω   -177.00-150.00   0.50    1.50    -- -106.00 -99.00 -90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0266913000
_diffrn_orient_matrix_UB_12      -0.1626716000
_diffrn_orient_matrix_UB_13      -0.0335626000
_diffrn_orient_matrix_UB_21      0.0750581000
_diffrn_orient_matrix_UB_22      -0.0926505000
_diffrn_orient_matrix_UB_23      0.0577018000
_diffrn_orient_matrix_UB_31      -0.3148446000
_diffrn_orient_matrix_UB_32      -0.0083189000
_diffrn_orient_matrix_UB_33      0.0136695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1467
_reflns_number_total             1752
_reflns_odcompleteness_completeness 97.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.043
_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)+(0.0674P)²+0.0821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1214
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4)
2.c 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
O10 O 0.0888(2) 0.81615(11) 0.49285(4) 0.0503(3) Uani 1 1 d . . . . .
N7 N -0.1525(2) 0.60686(14) 0.53923(4) 0.0446(3) Uani 1 1 d . . . . .
C8 C -0.1794(2) 0.44435(16) 0.53826(5) 0.0409(3) Uani 1 1 d . . . . .
C9 C 0.0290(3) 0.65544(16) 0.50024(5) 0.0427(3) Uani 1 1 d . . . . .
C1 C 0.3460(2) 0.66532(16) 0.42778(5) 0.0429(3) Uani 1 1 d . . . . .
C6 C 0.2812(3) 0.82038(17) 0.44799(5) 0.0463(3) Uani 1 1 d . . . . .
C2 C 0.5379(3) 0.64800(17) 0.38279(5) 0.0455(3) Uani 1 1 d . . . . .
H2 H 0.584449 0.545430 0.368875 0.055 Uiso 1 1 calc R . . . .
C3 C 0.6573(3) 0.78657(18) 0.35939(6) 0.0483(3) Uani 1 1 d . . . . .
C5 C 0.3964(3) 0.96088(18) 0.42592(6) 0.0538(4) Uani 1 1 d . . . . .
H5 H 0.350362 1.063281 0.440072 0.065 Uiso 1 1 calc R . . . .
C11 C 0.8543(3) 0.77381(19) 0.30864(6) 0.0524(4) Uani 1 1 d . . . . .
H11A H 1.003064 0.853950 0.314084 0.063 Uiso 1 1 calc R . . . .
H11B H 0.941192 0.667008 0.309338 0.063 Uiso 1 1 calc R . . . .
C4 C 0.5851(3) 0.93996(19) 0.38131(6) 0.0544(4) Uani 1 1 d . . . . .
H4 H 0.667296 1.031685 0.365251 0.065 Uiso 1 1 calc R . . . .
C12 C 0.7061(3) 0.8001(2) 0.24914(6) 0.0635(4) Uani 1 1 d . . . . .
H12A H 0.626517 0.908737 0.248007 0.076 Uiso 1 1 calc R . . . .
H12B H 0.551346 0.723384 0.244727 0.076 Uiso 1 1 calc R . . . .
C13 C 0.8948(4) 0.7803(3) 0.19754(7) 0.0732(5) Uani 1 1 d . . . . .
H13A H 0.786578 0.796405 0.161226 0.110 Uiso 1 1 calc GR . . . .
H13B H 0.973883 0.672793 0.198093 0.110 Uiso 1 1 calc GR . . . .
H13C H 1.043970 0.859077 0.200491 0.110 Uiso 1 1 calc GR . . . .


_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
O10 C9 1.3632(16) . ?
O10 C6 1.3940(14) . ?
N7 C8 1.3422(17) . ?
N7 C9 1.3205(15) . ?
C8 C9 1.4119(16) 3_566 ?
C8 C1 1.4423(17) 3_566 ?
C1 C6 1.3930(19) . ?
C1 C2 1.4015(16) . ?
C6 C5 1.3804(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C3 C11 1.5147(17) . ?
C3 C4 1.403(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.3880(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(2) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.510(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C9 O10 C6 105.05(9) . . ?
C9 N7 C8 110.76(10) . . ?
N7 C8 C9 122.56(11) . 3_566 ?
N7 C8 C1 131.88(11) . 3_566 ?
C9 C8 C1 105.56(12) 3_566 3_566 ?
O10 C9 C8 111.98(11) . 3_566 ?
N7 C9 O10 121.34(11) . . ?
N7 C9 C8 126.68(13) . 3_566 ?
C6 C1 C8 105.28(10) . 3_566 ?
C6 C1 C2 119.39(12) . . ?
C2 C1 C8 135.33(12) . 3_566 ?
C1 C6 O10 112.13(11) . . ?
C5 C6 O10 124.46(12) . . ?
C5 C6 C1 123.41(12) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.82(12) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C11 120.50(13) . . ?
C2 C3 C4 119.57(12) . . ?
C4 C3 C11 119.87(12) . . ?
C6 C5 H5 122.0 . . ?
C6 C5 C4 115.91(13) . . ?
C4 C5 H5 122.0 . . ?
C3 C11 H11A 109.0 . . ?
C3 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C3 112.78(11) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C3 C4 H4 118.6 . . ?
C5 C4 C3 122.90(13) . . ?
C5 C4 H4 118.6 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C11 C12 C13 113.90(13) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_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 2.025
_oxdiff_exptl_absorpt_empirical_full_min 0.531
####################################################################### 
# 
# 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_220415_et_1
_database_code_depnum_ccdc_archive 'CCDC 2305893'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 N O'
_chemical_formula_sum            'C10 H8 N O'
_chemical_formula_weight         158.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16 O2 N2'
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                   4.6059(4)
_cell_length_b                   8.2192(10)
_cell_length_c                   10.0903(11)
_cell_angle_alpha                89.474(10)
_cell_angle_beta                 85.283(8)
_cell_angle_gamma                84.126(9)
_cell_volume                     378.69(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      71.9470
_cell_measurement_theta_min      5.4430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             166
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -7 0.0207
1 1 6 0.0041
-3 0 -1 0.1176
0 -5 -1 0.0334
0 5 1 0.0457
3 0 1 0.1698
0 0 7 0.0205

_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.038
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1570 0.1168 -6.5443 0.0256 0.9851 0.1699
0.6214 1.2027 6.3559 -0.0235 -0.8982 -0.4391
-2.9362 0.2635 -1.2657 0.8909 0.0704 0.4488
-0.0193 -5.2785 -0.7256 -0.5603 -0.0441 0.8271
0.1191 5.2900 0.7714 0.5322 0.0419 -0.8456
2.9390 -0.2263 1.2720 -0.8877 -0.0702 -0.4551
0.0372 -0.4495 6.5092 -0.0258 -0.9947 -0.0996

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3407
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.632
_diffrn_reflns_theta_min         4.397
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -20.00   0.50    0.32    --  -42.55 -37.00  90.00   80
  2  ω    -87.00 -34.00   0.50    1.26    -- -106.00  77.00 150.00  106
  3  ω    -74.00 -41.00   0.50    1.26    -- -106.00 125.00  60.00   66
  4  ω    -83.00 -42.00   0.50    1.26    -- -106.00 125.00  30.00   82
  5  ω    -96.00 -71.00   0.50    1.26    -- -106.00 112.00 -41.00   50
  6  ω    -94.00 -67.00   0.50    1.26    -- -106.00 125.00 -30.00   54
  7  ω    -99.00 -72.00   0.50    1.26    -- -106.00 125.00-120.00   54
  8  ω   -116.00 -89.00   0.50    1.26    -- -106.00 125.00-180.00   54
  9  ω   -108.00 -32.00   0.50    1.26    -- -106.00  77.00-120.00  152
 10  ω    -62.00 -20.00   0.50    0.32    --  -42.55 112.00 -41.00   84
 11  ω    -93.00 -31.00   0.50    1.26    -- -106.00  37.00  60.00  124
 12  ω   -114.00 -86.00   0.50    1.26    -- -106.00 125.00  30.00   56
 13  ω   -111.00 -75.00   0.50    1.26    -- -106.00 125.00  60.00   72
 14  ω   -125.00 -96.00   0.50    1.26    -- -106.00  77.00 150.00   58
 15  ω   -127.00 -96.00   0.50    1.26    -- -106.00  37.00  60.00   62
 16  ω   -127.00 -32.00   0.50    1.26    -- -106.00  57.00  60.00  190
 17  ω   -118.00 -70.00   0.50    0.32    --  -42.55 -37.00  90.00   96
 18  ω   -115.00 -71.00   0.50    0.32    --  -42.55-125.00  90.00   88
 19  ω   -120.00 -93.00   0.50    1.26    -- -106.00 -37.00   0.00   54
 20  ω   -134.00 -26.00   0.50    1.26    -- -106.00  19.00 -60.00  216
 21  ω   -104.00 -79.00   0.50    1.26    -- -106.00-112.00-134.00   50
 22  ω   -160.00-105.00   0.50    1.26    -- -106.00 -99.00   0.00  110
 23  ω   -153.00 -83.00   0.50    1.26    -- -106.00 -99.00  90.00  140
 24  ω   -146.00 -72.00   0.50    1.26    -- -106.00-125.00 150.00  148
 25  ω   -168.00-135.00   0.50    1.26    -- -106.00 -37.00   0.00   66
 26  ω   -166.00-102.00   0.50    1.26    -- -106.00 -19.00 -90.00  128
 27  ω   -116.00 -91.00   0.50    1.26    -- -106.00 125.00 -90.00   50
 28  ω     68.00 113.00   0.50    0.32    --   42.55  57.00  30.00   90
 29  ω    114.00 140.00   0.50    1.26    --   76.50 112.00 -41.00   52
 30  ω     85.00 114.00   0.50    0.32    --   42.55 125.00-150.00   58
 31  ω     23.00  58.00   0.50    0.32    --   42.55  57.00  30.00   70
 32  ω     73.00 105.00   0.50    0.32    --   42.55 125.00 120.00   64
 33  ω     72.00 110.00   0.50    0.32    --   42.55 125.00  90.00   76
 34  ω     60.00  89.00   0.50    0.32    --   42.55-112.00-134.00   58
 35  ω     33.00  58.00   0.50    1.26    --   76.50-112.00-134.00   50
 36  ω     34.00  95.00   0.50    0.32    --   42.55-125.00-180.00  122
 37  ω      3.00  30.00   0.50    0.32    --   42.55-112.00-134.00   54
 38  ω   -174.00-149.00   0.50    1.26    -- -106.00-125.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2960380000
_diffrn_orient_matrix_UB_12      0.1065240000
_diffrn_orient_matrix_UB_13      0.0050858000
_diffrn_orient_matrix_UB_21      0.0437297000
_diffrn_orient_matrix_UB_22      0.0289571000
_diffrn_orient_matrix_UB_23      -0.1510647000
_diffrn_orient_matrix_UB_31      -0.1557887000
_diffrn_orient_matrix_UB_32      -0.1527021000
_diffrn_orient_matrix_UB_33      -0.0249533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1205
_reflns_number_total             1468
_reflns_odcompleteness_completeness 97.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.043
_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)+(0.1357P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1805
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C2(H2)
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
O5 O 0.1022(3) 0.81057(15) 0.49083(12) 0.0320(4) Uani 1 1 d . . . . .
N7 N -0.1740(3) 0.61380(18) 0.59328(14) 0.0303(4) Uani 1 1 d . . . . .
C6 C 0.0332(3) 0.6533(2) 0.50392(17) 0.0292(4) Uani 1 1 d . . . . .
C9 C 0.3945(4) 0.6474(2) 0.33601(17) 0.0297(5) Uani 1 1 d . . . . .
C4 C 0.3220(4) 0.8058(2) 0.38645(17) 0.0305(4) Uani 1 1 d . . . . .
C8 C -0.2062(3) 0.4535(2) 0.58763(16) 0.0296(5) Uani 1 1 d . . . . .
C3 C 0.4515(4) 0.9405(2) 0.33776(18) 0.0330(5) Uani 1 1 d . . . . .
H3 H 0.398075 1.044746 0.372367 0.040 Uiso 1 1 calc R . . . .
C10 C 0.6141(4) 0.6207(2) 0.23137(17) 0.0304(5) Uani 1 1 d . . . . .
H10 H 0.667569 0.516141 0.197422 0.036 Uiso 1 1 calc R . . . .
C1 C 0.7504(4) 0.7535(2) 0.17926(17) 0.0315(5) Uani 1 1 d . . . . .
C11 C 0.9747(4) 0.7324(2) 0.06048(18) 0.0340(5) Uani 1 1 d . . . . .
H11A H 1.074941 0.622767 0.061224 0.041 Uiso 1 1 calc R . . . .
H11B H 1.119241 0.809253 0.067087 0.041 Uiso 1 1 calc R . . . .
C2 C 0.6686(4) 0.9104(2) 0.23290(18) 0.0330(5) Uani 1 1 d . . . . .
H2 H 0.762479 0.997793 0.197283 0.040 Uiso 1 1 calc R . . . .
C12 C 0.8318(4) 0.7606(3) -0.0704(2) 0.0400(5) Uani 1 1 d . . . . .
H12A H 0.979267 0.746224 -0.143439 0.060 Uiso 1 1 calc GR . . . .
H12B H 0.735419 0.869718 -0.072052 0.060 Uiso 1 1 calc GR . . . .
H12C H 0.690927 0.683431 -0.077849 0.060 Uiso 1 1 calc GR . . . .


_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
O5 C6 1.365(2) . ?
O5 C4 1.397(2) . ?
N7 C6 1.321(2) . ?
N7 C8 1.343(2) . ?
C6 C8 1.418(2) 2_566 ?
C9 C4 1.401(3) . ?
C9 C8 1.435(2) 2_566 ?
C9 C10 1.403(2) . ?
C4 C3 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.400(2) . ?
C10 H10 0.9300 . ?
C10 C1 1.392(3) . ?
C1 C11 1.516(2) . ?
C1 C2 1.406(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.529(3) . ?
C2 H2 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O5 C4 104.95(12) . . ?
C6 N7 C8 110.94(15) . . ?
O5 C6 C8 112.01(14) . 2_566 ?
N7 C6 O5 121.18(14) . . ?
N7 C6 C8 126.81(17) . 2_566 ?
C4 C9 C8 105.52(15) . 2_566 ?
C4 C9 C10 119.26(16) . . ?
C10 C9 C8 135.23(17) . 2_566 ?
O5 C4 C9 111.91(15) . . ?
C3 C4 O5 124.36(15) . . ?
C3 C4 C9 123.73(16) . . ?
N7 C8 C6 122.24(16) . 2_566 ?
N7 C8 C9 132.13(16) . 2_566 ?
C6 C8 C9 105.61(15) 2_566 2_566 ?
C4 C3 H3 122.1 . . ?
C4 C3 C2 115.77(16) . . ?
C2 C3 H3 122.1 . . ?
C9 C10 H10 120.6 . . ?
C1 C10 C9 118.84(17) . . ?
C1 C10 H10 120.6 . . ?
C10 C1 C11 120.65(16) . . ?
C10 C1 C2 119.72(16) . . ?
C2 C1 C11 119.54(16) . . ?
C1 C11 H11A 109.3 . . ?
C1 C11 H11B 109.3 . . ?
C1 C11 C12 111.56(14) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C3 C2 C1 122.67(17) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.381
_oxdiff_exptl_absorpt_empirical_full_min 0.351
####################################################################### 
# 
# 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_221031_c111_2
_database_code_depnum_ccdc_archive 'CCDC 2305896'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N O'
_chemical_formula_sum            'C12 H12 N O'
_chemical_formula_weight         186.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H24 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 0.0181 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                   4.6829(2)
_cell_length_b                   8.2090(4)
_cell_length_c                   12.7307(7)
_cell_angle_alpha                89.289(4)
_cell_angle_beta                 86.831(4)
_cell_angle_gamma                85.180(4)
_cell_volume                     486.90(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5220
_cell_measurement_theta_min      5.3300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             198
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 4 1 0.0019
3 1 3 0.2794
0 5 3 0.1243
0 0 -8 0.0141
0 5 -1 0.1255
0 -5 1 0.0193
0 -1 8 0.0299

_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.055
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.7667 3.9504 1.2921 -0.2332 -0.9724 0.0092
2.9046 0.5466 2.8637 0.1105 0.4629 -0.8795
-0.1829 4.8446 3.2760 -0.1960 -0.8161 -0.5436
0.0958 0.1081 -8.2299 0.9153 -0.0236 0.4020
-0.1418 5.2594 -0.7343 0.2632 -0.8879 -0.3774
0.3658 -5.1664 1.1270 -0.2715 0.9158 0.2961
-0.0509 -0.6564 8.1723 -0.9240 0.1215 -0.3627

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5841
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.221
_diffrn_reflns_theta_min         3.477
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  21.00   0.50    0.06    --  -42.93  88.00-123.00   58
  2  ω    -61.00 -35.00   0.50    0.23    -- -106.00 125.00   0.00   52
  3  ω    -80.00 -54.00   0.50    0.23    -- -106.00  57.00  90.00   52
  4  ω   -103.00 -69.00   0.50    0.23    -- -106.00 125.00  60.00   68
  5  ω    -62.00 -36.00   0.50    0.23    -- -106.00 125.00 120.00   52
  6  ω    -89.00 -64.00   0.50    0.23    -- -106.00  77.00   0.00   50
  7  ω   -100.00 -42.00   0.50    0.23    -- -106.00  57.00 -60.00  116
  8  ω    -69.00 -43.00   0.50    0.23    -- -106.00  88.00-123.00   52
  9  ω    -64.00 -33.00   0.50    0.23    -- -106.00  88.00-162.18   62
 10  ω    -83.00 -33.00   0.50    0.23    -- -106.00  57.00-120.00  100
 11  ω    -82.00 -32.00   0.50    0.23    -- -106.00 125.00 -90.00  100
 12  ω    -75.00 -17.00   0.50    0.06    --  -42.93  88.00-123.00  116
 13  ω     21.00 112.00   0.50    0.06    --   42.93  57.00-120.00  182
 14  ω     89.00 114.00   0.50    0.23    --   76.50  88.00-123.00   50
 15  ω     71.00  96.00   0.50    0.06    --   42.93 125.00 -90.00   50
 16  ω     71.00  96.00   0.50    0.06    --   42.93 125.00-120.00   50
 17  ω     76.00 123.00   0.50    0.23    --   76.50 125.00 150.00   94
 18  ω    -20.00  37.00   0.50    0.06    --   42.93 -88.00 120.00  114
 19  ω     18.00  93.00   0.50    0.06    --   42.93-125.00 120.00  150
 20  ω     32.00  57.00   0.50    0.23    --   76.50 -88.00 120.00   50
 21  ω   -113.00 -71.00   0.50    0.06    --  -42.93-125.00-180.00   84
 22  ω   -117.00 -84.00   0.50    0.23    -- -106.00 -57.00-120.00   66
 23  ω   -141.00-116.00   0.50    0.23    -- -106.00 -57.00-150.00   50
 24  ω   -144.00-117.00   0.50    0.23    -- -106.00 -57.00-180.00   54
 25  ω   -159.00 -97.00   0.50    0.23    -- -106.00 -37.00 -90.00  124
 26  ω   -108.00 -83.00   0.50    0.23    -- -106.00 -57.00   0.00   50
 27  ω    -81.00 -56.00   0.50    0.23    -- -106.00   0.00   0.00   50
 28  ω   -126.00 -94.00   0.50    0.23    -- -106.00  57.00  90.00   64
 29  ω   -114.00 -78.00   0.50    0.23    -- -106.00  77.00  90.00   72
 30  ω   -107.00 -65.00   0.50    0.23    -- -106.00  93.00  73.36   84
 31  ω   -117.00 -91.00   0.50    0.23    -- -106.00 125.00 120.00   52
 32  ω   -124.00 -40.00   0.50    0.23    -- -106.00  37.00 150.00  168
 33  ω   -101.00 -76.00   0.50    0.23    -- -106.00 -19.00 120.00   50
 34  ω   -125.00 -95.00   0.50    0.23    -- -106.00 -88.00 120.00   60
 35  ω   -112.00 -86.00   0.50    0.23    -- -106.00 -99.00 150.00   52
 36  ω   -171.00 -75.00   0.50    0.23    -- -106.00 -19.00  30.00  192
 37  ω   -140.00-112.00   0.50    0.23    -- -106.00  88.00-123.00   56
 38  ω   -116.00 -44.00   0.50    0.23    -- -106.00 125.00-120.00  144
 39  ω   -106.00 -80.00   0.50    0.23    -- -106.00  88.00-162.18   52
 40  ω   -114.00 -87.00   0.50    0.23    -- -106.00 125.00 -90.00   54
 41  ω   -121.00 -93.00   0.50    0.23    -- -106.00  57.00-120.00   56
 42  ω   -116.00 -90.00   0.50    0.23    -- -106.00 125.00   0.00   52
 43  ω   -177.00-141.00   0.50    0.23    -- -106.00 -19.00 120.00   72
 44  ω   -176.00-136.00   0.50    0.23    -- -106.00 -57.00   0.00   80
 45  ω   -177.00-126.00   0.50    0.23    -- -106.00 -57.00-120.00  102
 46  ω   -176.00-148.00   0.50    0.23    -- -106.00 -57.00-150.00   56
 47  ω   -174.00-149.00   0.50    0.23    -- -106.00 -57.00-180.00   50
 48  ω   -174.00-134.00   0.50    0.23    -- -106.00-138.00  53.89   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1383735000
_diffrn_orient_matrix_UB_12      0.0385460000
_diffrn_orient_matrix_UB_13      -0.1091048000
_diffrn_orient_matrix_UB_21      0.1872448000
_diffrn_orient_matrix_UB_22      -0.1633617000
_diffrn_orient_matrix_UB_23      0.0029072000
_diffrn_orient_matrix_UB_31      -0.2347598000
_diffrn_orient_matrix_UB_32      -0.0854347000
_diffrn_orient_matrix_UB_33      -0.0526990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1627
_reflns_number_total             1953
_reflns_odcompleteness_completeness 98.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0647
_refine_ls_restrained_S_all      1.186
_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)+(0.0886P)²+0.2182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2131
_refine_ls_wR_factor_ref         0.2177
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
O10 O 0.1031(4) 0.8112(2) 0.99178(14) 0.0524(5) Uani 1 1 d . . . . .
N7 N -0.1650(4) 0.6120(3) 1.07341(16) 0.0477(5) Uani 1 1 d . . . . .
C8 C -0.1977(5) 0.4512(3) 1.06934(18) 0.0452(6) Uani 1 1 d . . . . .
C9 C 0.0339(5) 0.6530(3) 1.00283(19) 0.0455(6) Uani 1 1 d . . . . .
C6 C 0.3119(5) 0.8082(3) 0.9099(2) 0.0491(6) Uani 1 1 d . . . . .
C1 C 0.3802(5) 0.6512(3) 0.87064(19) 0.0461(6) Uani 1 1 d . . . . .
C2 C 0.5884(5) 0.6271(3) 0.78793(19) 0.0490(6) Uani 1 1 d . . . . .
H2 H 0.637189 0.523114 0.760973 0.059 Uiso 1 1 calc R . . . .
C3 C 0.7211(5) 0.7603(4) 0.7467(2) 0.0515(6) Uani 1 1 d . . . . .
C5 C 0.4400(6) 0.9435(4) 0.8712(2) 0.0567(7) Uani 1 1 d . . . . .
H5 H 0.391350 1.047301 0.898578 0.068 Uiso 1 1 calc R . . . .
C4 C 0.6453(6) 0.9163(4) 0.7891(2) 0.0565(7) Uani 1 1 d . . . . .
H4 H 0.736420 1.004706 0.761077 0.068 Uiso 1 1 calc R . . . .
C12 C 0.7837(6) 0.7591(4) 0.5490(2) 0.0568(7) Uani 1 1 d . . . . .
H12A H 0.648810 0.676015 0.546542 0.068 Uiso 1 1 calc R . . . .
H12B H 0.674892 0.864924 0.547109 0.068 Uiso 1 1 calc R . . . .
C11 C 0.9320(5) 0.7420(4) 0.6527(2) 0.0566(7) Uani 1 1 d . . . . .
H11A H 1.038406 0.635620 0.655717 0.068 Uiso 1 1 calc R . . . .
H11B H 1.067894 0.824528 0.655586 0.068 Uiso 1 1 calc R . . . .
C13 C 0.9869(6) 0.7435(4) 0.4524(2) 0.0616(7) Uani 1 1 d . . . . .
H13A H 1.102123 0.639889 0.455542 0.074 Uiso 1 1 calc R . . . .
H13B H 1.115877 0.830032 0.452706 0.074 Uiso 1 1 calc R . . . .
C14 C 0.8320(9) 0.7531(5) 0.3504(3) 0.0819(10) Uani 1 1 d . . . . .
H14A H 0.969672 0.738231 0.291926 0.123 Uiso 1 1 calc GR . . . .
H14B H 0.727041 0.858198 0.344788 0.123 Uiso 1 1 calc GR . . . .
H14C H 0.701400 0.669060 0.350210 0.123 Uiso 1 1 calc GR . . . .


_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
O10 C9 1.368(3) . ?
O10 C6 1.388(3) . ?
N7 C8 1.343(3) . ?
N7 C9 1.320(3) . ?
C8 C9 1.413(3) 2_567 ?
C8 C1 1.433(4) 2_567 ?
C6 C1 1.394(4) . ?
C6 C5 1.379(4) . ?
C1 C2 1.399(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(4) . ?
C3 C4 1.406(4) . ?
C3 C11 1.509(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(4) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.525(4) . ?
C12 C13 1.512(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.520(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C9 O10 C6 105.09(18) . . ?
C9 N7 C8 110.8(2) . . ?
N7 C8 C9 122.0(2) . 2_567 ?
N7 C8 C1 132.1(2) . 2_567 ?
C9 C8 C1 105.9(2) 2_567 2_567 ?
O10 C9 C8 111.5(2) . 2_567 ?
N7 C9 O10 121.3(2) . . ?
N7 C9 C8 127.2(2) . 2_567 ?
O10 C6 C1 112.2(2) . . ?
C5 C6 O10 124.6(2) . . ?
C5 C6 C1 123.2(3) . . ?
C6 C1 C8 105.3(2) . 2_567 ?
C6 C1 C2 119.3(2) . . ?
C2 C1 C8 135.3(2) . 2_567 ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 C11 120.9(3) . . ?
C4 C3 C11 119.5(3) . . ?
C6 C5 H5 121.8 . . ?
C6 C5 C4 116.3(3) . . ?
C4 C5 H5 121.8 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.6(3) . . ?
C5 C4 H4 118.7 . . ?
H12A C12 H12B 107.6 . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C13 C12 C11 114.1(2) . . ?
C3 C11 C12 112.1(2) . . ?
C3 C11 H11A 109.2 . . ?
C3 C11 H11B 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C12 C13 C14 112.8(3) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_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 2.527
_oxdiff_exptl_absorpt_empirical_full_min 0.424
####################################################################### 
# 
# 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_220830_c104_4
_database_code_depnum_ccdc_archive 'CCDC 2305897'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N O'
_chemical_formula_sum            'C12 H12 N O'
_chemical_formula_weight         186.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H24 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 0.0181 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                   5.0896(4)
_cell_length_b                   6.4884(4)
_cell_length_c                   15.6421(12)
_cell_angle_alpha                88.944(6)
_cell_angle_beta                 86.138(6)
_cell_angle_gamma                76.245(6)
_cell_volume                     500.60(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1206
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2200
_cell_measurement_theta_min      5.6780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             198
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 1 0.0260
-3 0 -1 0.0019
0 0 -10 0.0093
2 0 8 0.0079
0 4 0 0.0648
-1 -4 0 0.2180

_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.017
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.2271 0.1280 1.1809 0.0192 0.0780 0.9968
-3.2693 -0.4155 -0.9860 -0.0026 -0.0088 -1.0000
0.0727 0.1094 -10.1101 -0.9969 -0.0787 -0.0088
2.2638 0.2422 7.7618 0.6987 0.0553 0.7133
0.4045 4.1816 0.3500 0.0787 -0.9969 -0.0091
-0.7639 -4.2101 -0.4538 -0.0783 0.9918 -0.1014

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4594
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.312
_diffrn_reflns_theta_min         5.670
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     71.00  97.00   0.50   18.60    --   76.50  57.00 150.00   52
  2  ω    124.00 149.00   0.50   18.60    --   76.50  57.00 150.00   50
  3  ω    108.00 151.00   0.50   18.60    --   76.50 141.00  32.00   86
  4  ω     70.00 115.00   0.50    4.65    --   42.55 141.00  32.00   90
  5  ω     70.00 114.00   0.50    4.65    --   42.55 129.00-139.00   88
  6  ω     82.00 110.00   0.50   18.60    --   76.50 129.00-139.00   56
  7  ω     76.00 108.00   0.50    4.65    --   42.55  57.00-180.00   64
  8  ω     21.00  49.00   0.50    4.65    --   42.55  57.00-180.00   56
  9  ω    -71.00 -34.00   0.50    4.65    --  -42.55 129.00-139.00   74
 10  ω    -74.00 -32.00   0.50   18.60    -- -106.00  57.00 -90.00   84
 11  ω    -88.00 -28.00   0.50   18.60    -- -106.00  37.00 -90.00  120
 12  ω    -90.00 -56.00   0.50    4.65    --  -42.55 141.00  32.00   68
 13  ω   -114.00 -80.00   0.50   18.60    -- -106.00 141.00  32.00   68
 14  ω    -96.00 -33.00   0.50   18.60    -- -106.00 125.00  90.00  126
 15  ω    -96.00 -42.00   0.50   18.60    -- -106.00  77.00  90.00  108
 16  ω    -93.00 -28.00   0.50   18.60    -- -106.00  37.00  90.00  130
 17  ω   -116.00 -85.00   0.50   18.60    -- -106.00 -37.00  30.00   62
 18  ω   -124.00 -98.00   0.50   18.60    -- -106.00  37.00  90.00   52
 19  ω   -117.00 -33.00   0.50   18.60    -- -106.00  77.00 120.00  168
 20  ω   -135.00-100.00   0.50   18.60    -- -106.00  77.00  90.00   70
 21  ω   -176.00-130.00   0.50   18.60    -- -106.00 -37.00  30.00   92
 22  ω   -132.00 -84.00   0.50   18.60    -- -106.00 -57.00 -60.00   96
 23  ω   -115.00 -64.00   0.50    4.65    --  -42.55-141.00 -25.00  102
 24  ω     40.00  66.00   0.50    4.65    --   42.55-129.00 146.00   52
 25  ω     43.00  68.00   0.50   18.60    --   76.50-129.00 146.00   50
 26  ω   -115.00 -90.00   0.50    4.65    --  -42.55-129.00 146.00   50
 27  ω   -150.00 -98.00   0.50   18.60    -- -106.00-129.00 146.00  104
 28  ω   -140.00-115.00   0.50   18.60    -- -106.00-141.00 -25.00   50
 29  ω   -114.00 -79.00   0.50    4.65    --  -42.55-125.00 -90.00   70
 30  ω   -113.00 -20.00   0.50    4.65    --  -42.55 -77.00-120.00  186
 31  ω   -125.00 -93.00   0.50   18.60    -- -106.00  57.00 -90.00   64
 32  ω   -120.00 -75.00   0.50   18.60    -- -106.00 129.00-139.00   90
 33  ω   -117.00 -77.00   0.50   18.60    -- -106.00 125.00-180.00   80
 34  ω   -173.00-147.00   0.50   18.60    -- -106.00 -19.00-180.00   52
 35  ω   -131.00 -92.00   0.50   18.60    -- -106.00 -19.00-180.00   78
 36  ω   -174.00 -88.00   0.50   18.60    -- -106.00 -19.00 -90.00  172
 37  ω   -174.00-149.00   0.50   18.60    -- -106.00 -57.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0306295000
_diffrn_orient_matrix_UB_12      0.0135418000
_diffrn_orient_matrix_UB_13      0.0985264000
_diffrn_orient_matrix_UB_21      0.0318062000
_diffrn_orient_matrix_UB_22      -0.2419206000
_diffrn_orient_matrix_UB_23      0.0053983000
_diffrn_orient_matrix_UB_31      0.3091470000
_diffrn_orient_matrix_UB_32      -0.0323149000
_diffrn_orient_matrix_UB_33      0.0027418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1387
_reflns_number_total             1934
_reflns_odcompleteness_completeness 98.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.114
_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)+(0.1283P)²+0.1361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2297
_refine_ls_wR_factor_ref         0.2482
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), 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
O10 O 0.2561(4) 0.8097(3) 0.48273(13) 0.0641(7) Uani 1 1 d . . . . .
N7 N -0.0564(5) 0.6643(4) 0.56588(15) 0.0577(7) Uani 1 1 d . . . . .
C8 C -0.1726(6) 0.4983(4) 0.56682(18) 0.0551(8) Uani 1 1 d . . . . .
C6 C 0.4097(6) 0.7517(5) 0.40709(19) 0.0579(8) Uani 1 1 d . . . . .
C9 C 0.1120(6) 0.6573(4) 0.49837(18) 0.0553(7) Uani 1 1 d . . . . .
C1 C 0.3671(6) 0.5642(5) 0.37357(19) 0.0565(8) Uani 1 1 d . . . . .
C2 C 0.5100(7) 0.4819(5) 0.2980(2) 0.0637(9) Uani 1 1 d . . . . .
H2 H 0.484070 0.357289 0.275277 0.076 Uiso 1 1 calc R . . . .
C3 C 0.6921(7) 0.5864(5) 0.2563(2) 0.0665(9) Uani 1 1 d . . . . .
C4 C 0.7247(7) 0.7739(5) 0.2932(2) 0.0688(9) Uani 1 1 d . . . . .
H4 H 0.845768 0.844093 0.265577 0.083 Uiso 1 1 calc R . . . .
C5 C 0.5875(7) 0.8590(5) 0.3678(2) 0.0671(9) Uani 1 1 d . . . . .
H5 H 0.613701 0.983379 0.390738 0.080 Uiso 1 1 calc R . . . .
C11 C 0.8501(8) 0.5015(6) 0.1734(3) 0.0837(11) Uani 1 1 d . . . . .
H11 H 0.998400 0.573705 0.164151 0.100 Uiso 1 1 calc R . . . .
C14 C 0.9826(10) 0.2544(7) 0.1785(3) 0.1142(18) Uani 1 1 d . . . . .
H14A H 1.073520 0.223341 0.230742 0.171 Uiso 1 1 calc GR . . . .
H14B H 1.110986 0.213172 0.130485 0.171 Uiso 1 1 calc GR . . . .
H14C H 0.843573 0.177335 0.177548 0.171 Uiso 1 1 calc GR . . . .
C12 C 0.6808(12) 0.5503(9) 0.0982(3) 0.1118(16) Uani 1 1 d . . . . .
H12A H 0.787307 0.486003 0.047647 0.134 Uiso 1 1 calc R . . . .
H12B H 0.527493 0.485951 0.107276 0.134 Uiso 1 1 calc R . . . .
C13 C 0.5821(16) 0.7719(10) 0.0827(4) 0.150(3) Uani 1 1 d . . . . .
H13A H 0.456657 0.791879 0.038410 0.225 Uiso 1 1 calc GR . . . .
H13B H 0.731241 0.833082 0.065000 0.225 Uiso 1 1 calc GR . . . .
H13C H 0.492058 0.839641 0.134284 0.225 Uiso 1 1 calc GR . . . .


_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
O10 C6 1.380(4) . ?
O10 C9 1.374(4) . ?
N7 C8 1.346(4) . ?
N7 C9 1.309(4) . ?
C8 C9 1.415(4) 2_566 ?
C8 C1 1.437(4) 2_566 ?
C6 C1 1.402(4) . ?
C6 C5 1.375(5) . ?
C1 C2 1.391(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(5) . ?
C3 C4 1.405(5) . ?
C3 C11 1.520(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C5 H5 0.9300 . ?
C11 H11 0.9800 . ?
C11 C14 1.588(6) . ?
C11 C12 1.489(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.428(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C9 O10 C6 105.8(2) . . ?
C9 N7 C8 110.7(2) . . ?
N7 C8 C9 122.2(3) . 2_566 ?
N7 C8 C1 131.8(3) . 2_566 ?
C9 C8 C1 106.0(3) 2_566 2_566 ?
O10 C6 C1 111.9(3) . . ?
C5 C6 O10 125.6(3) . . ?
C5 C6 C1 122.5(3) . . ?
O10 C9 C8 111.0(3) . 2_566 ?
N7 C9 O10 121.9(2) . . ?
N7 C9 C8 127.1(3) . 2_566 ?
C6 C1 C8 105.3(3) . 2_566 ?
C2 C1 C8 135.5(3) . 2_566 ?
C2 C1 C6 119.2(3) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 C11 121.3(3) . . ?
C4 C3 C11 120.8(3) . . ?
C3 C4 H4 118.2 . . ?
C5 C4 C3 123.6(3) . . ?
C5 C4 H4 118.2 . . ?
C6 C5 H5 121.6 . . ?
C4 C5 C6 116.8(3) . . ?
C4 C5 H5 121.6 . . ?
C3 C11 H11 107.3 . . ?
C3 C11 C14 112.1(3) . . ?
C14 C11 H11 107.3 . . ?
C12 C11 C3 112.0(3) . . ?
C12 C11 H11 107.3 . . ?
C12 C11 C14 110.5(4) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.9(5) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_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 2.859
_oxdiff_exptl_absorpt_empirical_full_min 0.389
####################################################################### 
# 
# 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_220620_c70_1
_database_code_depnum_ccdc_archive 'CCDC 2305895'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 N O'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H20 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 0.0181 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      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                   11.3694(3)
_cell_length_b                   4.98710(10)
_cell_length_c                   15.6263(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.944(2)
_cell_angle_gamma                90
_cell_volume                     875.24(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8940
_cell_measurement_theta_min      4.5120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 -7 0.0733
4 0 7 0.0639
-1 -3 -2 0.3815
7 0 -5 0.0527
1 3 2 0.2705
-7 0 5 0.0299
2 0 -10 0.0612

_exptl_crystal_size_max          0.716
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.102
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.3333 -0.0585 -7.1812 0.2247 0.9365 0.2692
4.3365 0.0987 7.1737 -0.2239 -0.9332 -0.2812
-0.7251 -3.1477 -1.9784 -0.1058 0.0030 0.9944
6.8393 0.2253 -5.1629 -0.9825 0.0254 -0.1844
1.1982 3.1383 1.6011 0.0362 -0.0012 -0.9993
-6.8203 -0.0607 5.2812 0.9908 -0.0257 0.1328
2.3136 0.1034 -10.0043 -0.6481 0.7584 0.0698

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11654
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.167
_diffrn_reflns_theta_min         4.494
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  45.00   0.50    0.05    --   42.93 -19.00 -21.00   80
  2  ω     50.00  86.00   0.50    0.05    --   42.93  19.00 146.00   72
  3  ω     27.00  52.00   0.50    0.14    --   76.50 -19.00 -21.00   50
  4  ω     78.00 104.00   0.50    0.14    --   76.50  19.00 146.00   52
  5  ω    -63.00 -37.00   0.50    0.14    -- -106.00  19.00 146.00   52
  6  ω   -177.00-132.00   0.50    0.14    -- -106.00 -19.00 -21.00   90
  7  ω   -130.00 -80.00   0.50    0.14    -- -106.00  19.00 146.00  100
  8  ω   -120.00 -22.00   0.50    0.05    --  -42.93 -37.00-120.00  196
  9  ω   -123.00 -56.00   0.50    0.05    --  -42.93 -19.00 -21.00  134
 10  ω    -95.00 -11.00   0.50    0.05    --  -42.93 125.00-150.00  168
 11  ω     15.00  84.00   0.50    0.05    --   42.93  77.00-120.00  138
 12  ω     49.00  94.00   0.50    0.14    --   76.50  77.00 -60.00   90
 13  ω     48.00  76.00   0.50    0.14    --   76.50  77.00-150.00   56
 14  ω     48.00  75.00   0.50    0.14    --   76.50  77.00 -90.00   54
 15  ω     48.00  82.00   0.50    0.14    --   76.50  77.00 -30.00   68
 16  ω     55.00 102.00   0.50    0.14    --   76.50  57.00-150.00   94
 17  ω     48.00  75.00   0.50    0.14    --   76.50  81.00 -88.94   54
 18  ω     48.00  77.00   0.50    0.14    --   76.50  77.00-120.00   58
 19  ω   -138.00 -85.00   0.50    0.14    -- -106.00 -58.00-128.66  106
 20  ω   -102.00 -77.00   0.50    0.14    -- -106.00 -77.00-150.00   50
 21  ω   -107.00 -81.00   0.50    0.14    -- -106.00 -77.00 -71.93   52
 22  ω   -114.00 -78.00   0.50    0.14    -- -106.00 -77.00-120.00   72
 23  ω   -130.00 -79.00   0.50    0.14    -- -106.00 -71.00 -62.21  102
 24  ω   -109.00 -83.00   0.50    0.14    -- -106.00 -77.00 -30.00   52
 25  ω   -128.00 -34.00   0.50    0.14    -- -106.00  57.00   0.00  188
 26  ω   -177.00-151.00   0.50    0.14    -- -106.00-125.00 120.00   52
 27  ω    -88.00 -32.00   0.50    0.14    -- -106.00 125.00-180.00  112
 28  ω   -106.00 -81.00   0.50    0.14    -- -106.00 -66.00-144.42   50
 29  ω   -141.00-111.00   0.50    0.14    -- -106.00-125.00 120.00   60
 30  ω   -172.00 -97.00   0.50    0.14    -- -106.00 -99.00 150.00  150
 31  ω   -117.00 -91.00   0.50    0.14    -- -106.00 125.00-180.00   52
 32  ω   -143.00-117.00   0.50    0.14    -- -106.00 -77.00 -30.00   52
 33  ω   -177.00 -86.00   0.50    0.14    -- -106.00 -37.00  60.00  182
 34  ω   -132.00-107.00   0.50    0.14    -- -106.00 -78.00 -35.09   50
 35  ω   -110.00 -85.00   0.50    0.14    -- -106.00 -67.00 -88.89   50
 36  ω   -126.00 -99.00   0.50    0.14    -- -106.00  57.00-150.00   54
 37  ω    -80.00 -55.00   0.50    0.14    -- -106.00  57.00-150.00   50
 38  ω   -172.00 -85.00   0.50    0.14    -- -106.00 -59.00-149.88  174
 39  ω   -162.00 -82.00   0.50    0.14    -- -106.00 -64.00-175.72  160
 40  ω   -105.00 -80.00   0.50    0.14    -- -106.00 -71.00 -73.16   50
 41  ω    -66.00 -41.00   0.50    0.14    -- -106.00  37.00-120.00   50
 42  ω   -104.00 -79.00   0.50    0.14    -- -106.00 -72.00-172.28   50
 43  ω   -105.00 -80.00   0.50    0.14    -- -106.00 -69.00 -55.35   50
 44  ω   -125.00 -73.00   0.50    0.14    -- -106.00  37.00-120.00  104
 45  ω   -110.00 -85.00   0.50    0.14    -- -106.00 -57.00-120.00   50
 46  ω   -163.00 -83.00   0.50    0.14    -- -106.00 -57.00 -90.00  160
 47  ω   -117.00 -83.00   0.50    0.14    -- -106.00 -61.00-165.81   68
 48  ω   -101.00 -76.00   0.50    0.14    -- -106.00 -80.00-170.17   50
 49  ω   -104.00 -79.00   0.50    0.14    -- -106.00 -77.00 -90.00   50
 50  ω    -82.00 -33.00   0.50    0.14    -- -106.00 125.00 150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1159008000
_diffrn_orient_matrix_UB_12      0.0362066000
_diffrn_orient_matrix_UB_13      0.0383500000
_diffrn_orient_matrix_UB_21      -0.0669981000
_diffrn_orient_matrix_UB_22      0.0714112000
_diffrn_orient_matrix_UB_23      -0.0905617000
_diffrn_orient_matrix_UB_31      -0.0299611000
_diffrn_orient_matrix_UB_32      -0.2983266000
_diffrn_orient_matrix_UB_33      -0.0169846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1609
_reflns_number_total             1765
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.108
_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)+(0.0602P)²+0.1198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1129
_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:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), 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
O10 O 0.68968(7) 0.29954(19) 0.49185(5) 0.0488(3) Uani 1 1 d . . . . .
N7 N 0.60328(9) -0.0345(2) 0.56731(6) 0.0437(3) Uani 1 1 d . . . . .
C8 C 0.50172(10) -0.1746(2) 0.56399(7) 0.0398(3) Uani 1 1 d . . . . .
C1 C 0.53415(10) 0.3794(2) 0.38055(7) 0.0405(3) Uani 1 1 d . . . . .
C9 C 0.59640(10) 0.1347(2) 0.50220(7) 0.0412(3) Uani 1 1 d . . . . .
C6 C 0.65009(11) 0.4486(3) 0.41761(7) 0.0432(3) Uani 1 1 d . . . . .
C2 C 0.48103(11) 0.5117(2) 0.30561(7) 0.0432(3) Uani 1 1 d . . . . .
H2 H 0.403772 0.468972 0.280350 0.052 Uiso 1 1 calc R . . . .
C3 C 0.54457(11) 0.7074(2) 0.26918(7) 0.0430(3) Uani 1 1 d . . . . .
C4 C 0.66034(11) 0.7707(3) 0.30920(8) 0.0477(3) Uani 1 1 d . . . . .
H4 H 0.702125 0.902909 0.284622 0.057 Uiso 1 1 calc R . . . .
C5 C 0.71502(11) 0.6441(3) 0.38396(8) 0.0498(3) Uani 1 1 d . . . . .
H5 H 0.791667 0.689049 0.409995 0.060 Uiso 1 1 calc R . . . .
C11 C 0.49113(12) 0.8539(3) 0.18671(8) 0.0511(3) Uani 1 1 d . . . . .
H11 H 0.532473 1.026172 0.186194 0.061 Uiso 1 1 calc R . . . .
C13 C 0.35890(14) 0.9139(4) 0.18302(11) 0.0671(4) Uani 1 1 d . . . . .
H13A H 0.314001 0.751429 0.171227 0.101 Uiso 1 1 calc GR . . . .
H13B H 0.334109 1.041835 0.137924 0.101 Uiso 1 1 calc GR . . . .
H13C H 0.345358 0.986114 0.237599 0.101 Uiso 1 1 calc GR . . . .
C12 C 0.51440(19) 0.6968(4) 0.10707(10) 0.0792(5) Uani 1 1 d . . . . .
H12A H 0.598321 0.665302 0.110602 0.119 Uiso 1 1 calc GR . . . .
H12B H 0.486244 0.798055 0.055726 0.119 Uiso 1 1 calc GR . . . .
H12C H 0.473260 0.528197 0.104855 0.119 Uiso 1 1 calc GR . . . .


_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
O10 C9 1.3711(15) . ?
O10 C6 1.3924(14) . ?
N7 C8 1.3439(15) . ?
N7 C9 1.3147(15) . ?
C8 C1 1.4387(16) 3_656 ?
C8 C9 1.4125(16) 3_656 ?
C1 C6 1.3982(16) . ?
C1 C2 1.3969(16) . ?
C6 C5 1.3757(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.3879(17) . ?
C3 C4 1.4026(18) . ?
C3 C11 1.5233(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.3870(18) . ?
C5 H5 0.9300 . ?
C11 H11 0.9800 . ?
C11 C13 1.525(2) . ?
C11 C12 1.528(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
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
C9 O10 C6 105.23(9) . . ?
C9 N7 C8 110.89(10) . . ?
N7 C8 C1 131.93(10) . 3_656 ?
N7 C8 C9 122.07(11) . 3_656 ?
C9 C8 C1 106.00(10) 3_656 3_656 ?
C6 C1 C8 105.26(10) . 3_656 ?
C2 C1 C8 135.57(11) . 3_656 ?
C2 C1 C6 119.17(11) . . ?
O10 C9 C8 111.49(10) . 3_656 ?
N7 C9 O10 121.47(10) . . ?
N7 C9 C8 127.04(11) . 3_656 ?
O10 C6 C1 112.02(11) . . ?
C5 C6 O10 125.00(11) . . ?
C5 C6 C1 122.97(11) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.42(11) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 119.18(11) . . ?
C2 C3 C11 121.32(11) . . ?
C4 C3 C11 119.50(11) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.67(12) . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 116.58(11) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C3 C11 H11 107.4 . . ?
C3 C11 C13 112.78(11) . . ?
C3 C11 C12 110.26(12) . . ?
C13 C11 H11 107.4 . . ?
C13 C11 C12 111.36(14) . . ?
C12 C11 H11 107.4 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_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 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.491
####################################################################### 
# 
# 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_220818_c141_1
_database_code_depnum_ccdc_archive 'CCDC 2305899'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N O'
_chemical_formula_sum            'C13 H14 N O'
_chemical_formula_weight         200.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H30 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 0.0181 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      monoclinic
_space_group_IT_number           14
_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                   6.5784(2)
_cell_length_b                   11.0323(3)
_cell_length_c                   15.2453(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.443(2)
_cell_angle_gamma                90
_cell_volume                     1091.43(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3928
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6460
_cell_measurement_theta_min      4.9770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -9 0.0742
-4 1 4 0.3845
0 -3 9 0.1001
0 6 5 0.0299
-4 0 2 0.4052
0 -6 -5 0.0393
0 -3 9 0.0743
4 -1 -3 0.2982

_exptl_crystal_size_max          0.715
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.076
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1456 3.3764 -8.6562 0.2330 0.9716 0.0408
-4.1391 0.7908 3.7142 -0.0318 -0.1305 -0.9909
-0.0915 -3.3942 8.6266 -0.2331 -0.9721 -0.0279
0.3044 6.2710 4.5499 -0.9638 0.2311 -0.1328
-4.2671 0.2024 1.8359 0.1639 -0.0396 -0.9857
-0.2296 -6.2776 -4.5843 0.9614 -0.2305 0.1501
0.3904 -2.8452 8.7649 -0.3328 -0.9407 0.0658
4.1816 -1.2851 -2.5058 -0.0029 -0.0085 1.0000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8424
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.186
_diffrn_reflns_theta_min         4.972
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     14.00 115.00   0.50    0.05    --   42.93  77.00-120.00  202
  2  ω     90.00 115.00   0.50    0.15    --   76.50 114.00-177.00   50
  3  ω     50.00  81.00   0.50    0.05    --   42.93 177.00 -40.00   62
  4  ω     70.00  95.00   0.50    0.15    --   76.50 177.00 -40.00   50
  5  ω     90.00 115.00   0.50    0.05    --   42.93 125.00  90.00   50
  6  ω     21.00  84.00   0.50    0.05    --   42.93-114.00  91.00  126
  7  ω     33.00  58.00   0.50    0.15    --   76.50-114.00  91.00   50
  8  ω     55.00  80.00   0.50    0.05    --   42.93-177.00 -45.00   50
  9  ω     52.00  77.00   0.50    0.15    --   76.50-177.00 -45.00   50
 10  ω   -104.00 -79.00   0.50    0.05    --  -42.93-177.00 -45.00   50
 11  ω    -76.00 -43.00   0.50    0.15    -- -106.00 177.00 -40.00   66
 12  ω    -90.00 -48.00   0.50    0.05    --  -42.93 114.00-177.00   84
 13  ω   -111.00 -31.00   0.50    0.15    -- -106.00 114.00-177.00  160
 14  ω   -106.00 -35.00   0.50    0.15    -- -106.00  57.00-150.00  142
 15  ω   -111.00 -37.00   0.50    0.15    -- -106.00 125.00 -30.00  148
 16  ω    -73.00 -47.00   0.50    0.15    -- -106.00  77.00  30.00   52
 17  ω   -110.00 -85.00   0.50    0.15    -- -106.00 -19.00 150.00   50
 18  ω   -120.00 -82.00   0.50    0.15    -- -106.00 -77.00 120.00   76
 19  ω   -151.00-126.00   0.50    0.15    -- -106.00-114.00  91.00   50
 20  ω   -160.00-128.00   0.50    0.15    -- -106.00 -77.00 120.00   64
 21  ω   -176.00-128.00   0.50    0.15    -- -106.00 -19.00 150.00   96
 22  ω   -124.00 -98.00   0.50    0.15    -- -106.00  77.00  30.00   52
 23  ω   -116.00 -91.00   0.50    0.15    -- -106.00 125.00 120.00   50
 24  ω   -119.00 -93.00   0.50    0.15    -- -106.00 177.00 -40.00   52
 25  ω   -167.00-141.00   0.50    0.15    -- -106.00 -77.00-180.00   52
 26  ω   -118.00 -77.00   0.50    0.15    -- -106.00 -77.00-180.00   82
 27  ω   -110.00 -71.00   0.50    0.05    --  -42.93-125.00-150.00   78
 28  ω   -175.00 -72.00   0.50    0.15    -- -106.00-125.00 -60.00  206
 29  ω   -167.00 -84.00   0.50    0.15    -- -106.00 -99.00-150.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0722895000
_diffrn_orient_matrix_UB_12      -0.1011501000
_diffrn_orient_matrix_UB_13      -0.0675885000
_diffrn_orient_matrix_UB_21      -0.0191118000
_diffrn_orient_matrix_UB_22      0.0931019000
_diffrn_orient_matrix_UB_23      -0.0762516000
_diffrn_orient_matrix_UB_31      0.2253235000
_diffrn_orient_matrix_UB_32      -0.0245028000
_diffrn_orient_matrix_UB_33      -0.0104792000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1903
_reflns_number_total             2196
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.048
_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)+(0.0737P)²+0.0969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(1)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(H13A)=
 Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C3(H3)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C13(H13D,H13E,H13F), C14(H14A,H14B,
 H14C), C15A(H15D,H15E,H15F), C14A(H14D,H14E,H14F)
;
_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
O5 O 0.30563(13) 0.34514(8) 0.49812(6) 0.0559(3) Uani 1 1 d . . . . .
N7 N -0.02183(15) 0.40847(9) 0.42966(7) 0.0498(3) Uani 1 1 d . . . . .
C1 C 0.66939(18) 0.48203(12) 0.72515(8) 0.0495(3) Uani 1 1 d . . . . .
C9 C 0.36337(18) 0.48230(11) 0.61437(7) 0.0464(3) Uani 1 1 d . . . . .
C6 C 0.13848(19) 0.42042(11) 0.49310(8) 0.0478(3) Uani 1 1 d . . . . .
C4 C 0.44155(19) 0.38449(12) 0.57235(8) 0.0505(3) Uani 1 1 d . . . . .
C8 C -0.16471(18) 0.49310(10) 0.43789(7) 0.0464(3) Uani 1 1 d . . . . .
C10 C 0.47846(19) 0.53138(12) 0.69102(8) 0.0487(3) Uani 1 1 d . . . . .
H10 H 0.427711 0.596859 0.719203 0.058 Uiso 1 1 calc R . . . .
C11 C 0.7947(2) 0.53301(15) 0.81077(9) 0.0599(4) Uani 1 1 d . . . . .
C2 C 0.7407(2) 0.38422(13) 0.67988(9) 0.0571(3) Uani 1 1 d . . . . .
H2 H 0.868575 0.351109 0.702528 0.069 Uiso 1 1 calc R . . . .
C3 C 0.6302(2) 0.33438(13) 0.60306(9) 0.0588(4) Uani 1 1 d . . . . .
H3 H 0.681688 0.270130 0.573850 0.071 Uiso 1 1 calc R . . . .
C12 C 0.6692(3) 0.51834(17) 0.88756(10) 0.0643(5) Uani 0.871(4) 1 d . . P A 1
H12A H 0.748567 0.551828 0.941339 0.077 Uiso 0.871(4) 1 calc R . P A 1
H12B H 0.543537 0.565458 0.873638 0.077 Uiso 0.871(4) 1 calc R . P A 1
C15 C 0.8222(4) 0.67153(19) 0.79731(15) 0.0826(7) Uani 0.871(4) 1 d . . P A 1
H15A H 0.896403 0.684570 0.748905 0.124 Uiso 0.871(4) 1 calc GR . P A 1
H15B H 0.897914 0.706054 0.850658 0.124 Uiso 0.871(4) 1 calc GR . P A 1
H15C H 0.689333 0.709400 0.784069 0.124 Uiso 0.871(4) 1 calc GR . P A 1
C13 C 0.6123(4) 0.3882(2) 0.90581(14) 0.1043(7) Uani 1 1 d . . . . .
H13A H 0.538785 0.352818 0.852327 0.156 Uiso 0.871(4) 1 calc GR . P A 1
H13B H 0.526722 0.387210 0.951114 0.156 Uiso 0.871(4) 1 calc GR . P A 1
H13C H 0.735440 0.342437 0.925500 0.156 Uiso 0.871(4) 1 calc GR . P A 1
H13D H 0.515290 0.450748 0.884377 0.156 Uiso 0.129(4) 1 calc GR . P A 2
H13E H 0.625740 0.382899 0.969352 0.156 Uiso 0.129(4) 1 calc GR . P A 2
H13F H 0.564335 0.312056 0.879783 0.156 Uiso 0.129(4) 1 calc GR . P A 2
C14 C 1.0044(3) 0.4751(3) 0.83488(18) 0.0942(9) Uani 0.871(4) 1 d . . P A 1
H14A H 0.988383 0.390873 0.848155 0.141 Uiso 0.871(4) 1 calc GR . P A 1
H14B H 1.079886 0.515032 0.886008 0.141 Uiso 0.871(4) 1 calc GR . P A 1
H14C H 1.078254 0.482428 0.785808 0.141 Uiso 0.871(4) 1 calc GR . P A 1
C15A C 0.735(2) 0.6335(14) 0.8456(9) 0.081(5) Uani 0.129(4) 1 d . . P A 2
H15D H 0.596873 0.623971 0.856994 0.121 Uiso 0.129(4) 1 calc GR . P A 2
H15E H 0.740167 0.699448 0.804925 0.121 Uiso 0.129(4) 1 calc GR . P A 2
H15F H 0.825420 0.650485 0.900412 0.121 Uiso 0.129(4) 1 calc GR . P A 2
C14A C 1.037(3) 0.543(2) 0.7958(11) 0.092(5) Uani 0.129(4) 1 d . . P A 2
H14D H 1.080951 0.465906 0.775777 0.138 Uiso 0.129(4) 1 calc GR . P A 2
H14E H 1.122460 0.564060 0.850942 0.138 Uiso 0.129(4) 1 calc GR . P A 2
H14F H 1.049392 0.603614 0.752028 0.138 Uiso 0.129(4) 1 calc GR . P A 2
C12A C 0.806(3) 0.4160(16) 0.8821(9) 0.089(5) Uani 0.129(4) 1 d . . P A 2
H12C H 0.857531 0.345158 0.855257 0.107 Uiso 0.129(4) 1 calc R . P A 2
H12D H 0.902187 0.435444 0.935507 0.107 Uiso 0.129(4) 1 calc R . P A 2


_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
O5 C6 1.3701(15) . ?
O5 C4 1.3916(14) . ?
N7 C6 1.3154(16) . ?
N7 C8 1.3452(15) . ?
C1 C10 1.3893(18) . ?
C1 C11 1.5317(17) . ?
C1 C2 1.4025(19) . ?
C9 C4 1.3955(18) . ?
C9 C8 1.4403(16) 3_566 ?
C9 C10 1.3935(16) . ?
C6 C8 1.4097(16) 3_566 ?
C4 C3 1.3690(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.548(2) . ?
C11 C15 1.556(3) . ?
C11 C14 1.510(3) . ?
C11 C15A 1.317(14) . ?
C11 C14A 1.652(18) . ?
C11 C12A 1.682(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.3867(18) . ?
C3 H3 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.521(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 H13D 0.9600 . ?
C13 H13E 0.9600 . ?
C13 H13F 0.9600 . ?
C13 C12A 1.413(17) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?

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
C6 O5 C4 105.01(9) . . ?
C6 N7 C8 110.49(10) . . ?
C10 C1 C11 120.14(12) . . ?
C10 C1 C2 118.17(11) . . ?
C2 C1 C11 121.68(12) . . ?
C4 C9 C8 105.14(10) . 3_566 ?
C10 C9 C4 119.67(11) . . ?
C10 C9 C8 135.19(12) . 3_566 ?
O5 C6 C8 111.70(10) . 3_566 ?
N7 C6 O5 121.30(10) . . ?
N7 C6 C8 127.00(11) . 3_566 ?
O5 C4 C9 112.24(10) . . ?
C3 C4 O5 125.28(12) . . ?
C3 C4 C9 122.48(11) . . ?
N7 C8 C9 131.58(11) . 3_566 ?
N7 C8 C6 122.51(11) . 3_566 ?
C6 C8 C9 105.91(10) 3_566 3_566 ?
C1 C10 C9 119.68(12) . . ?
C1 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C1 C11 C12 109.09(12) . . ?
C1 C11 C15 107.83(13) . . ?
C1 C11 C14A 107.6(6) . . ?
C1 C11 C12A 103.3(5) . . ?
C12 C11 C15 106.88(15) . . ?
C14 C11 C1 113.22(14) . . ?
C14 C11 C12 110.54(17) . . ?
C14 C11 C15 109.04(19) . . ?
C15A C11 C1 120.0(5) . . ?
C15A C11 C14A 111.0(10) . . ?
C15A C11 C12A 111.7(9) . . ?
C14A C11 C12A 101.4(9) . . ?
C1 C2 H2 118.3 . . ?
C3 C2 C1 123.32(12) . . ?
C3 C2 H2 118.3 . . ?
C4 C3 C2 116.67(12) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.51(16) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C12A C13 H13D 109.5 . . ?
C12A C13 H13E 109.5 . . ?
C12A C13 H13F 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15A H15D 109.5 . . ?
C11 C15A H15E 109.5 . . ?
C11 C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C11 C14A H14D 109.5 . . ?
C11 C14A H14E 109.5 . . ?
C11 C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C11 C12A H12C 109.0 . . ?
C11 C12A H12D 109.0 . . ?
C13 C12A C11 112.8(10) . . ?
C13 C12A H12C 109.0 . . ?
C13 C12A H12D 109.0 . . ?
H12C C12A H12D 107.8 . . ?

_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 1.466
_oxdiff_exptl_absorpt_empirical_full_min 0.477
####################################################################### 
# 
# 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_220712_c86_needle_2
_database_code_depnum_ccdc_archive 'CCDC 2305901'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N O'
_chemical_formula_sum            'C14 H14 N O'
_chemical_formula_weight         212.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H28 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 0.0181 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      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                   11.9199(3)
_cell_length_b                   4.78060(10)
_cell_length_c                   18.7426(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.523(2)
_cell_angle_gamma                90
_cell_volume                     1067.00(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3537
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2490
_cell_measurement_theta_min      4.3120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 10 0.1079
0 -3 1 0.2565
-4 0 -10 0.1374
1 3 2 0.3630
7 0 -7 0.0501
-7 0 7 0.0705

_exptl_crystal_size_max          0.679
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.127
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.2517 0.1395 9.8427 0.2249 0.9374 0.2659
-0.3344 -3.0971 0.6809 0.0564 0.2372 -0.9698
-4.2414 -0.0363 -9.8674 -0.2269 -0.9455 -0.2336
1.4207 3.0182 1.6808 -0.0085 0.0023 1.0000
6.5303 -0.0103 -6.9649 -0.9704 0.2327 0.0651
-6.5087 0.0749 7.0103 0.9715 -0.2330 -0.0438

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6689
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.224
_diffrn_reflns_theta_min         4.311
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  11.00   0.50    0.05    --   42.93 -18.00   9.00   52
  2  ω     53.00  82.00   0.50    0.05    --   76.50 -18.00   9.00   58
  3  ω     24.00 124.00   0.50    0.05    --   42.93  18.00 177.00  200
  4  ω    124.00 155.00   0.50    0.05    --   76.50  18.00 177.00   62
  5  ω     72.00 116.00   0.50    0.05    --   42.93 125.00 -90.00   88
  6  ω    -60.00 -34.00   0.50    0.05    -- -106.00  57.00-180.00   52
  7  ω    -65.00 -33.00   0.50    0.05    -- -106.00 125.00-120.00   64
  8  ω    -77.00 -35.00   0.50    0.05    -- -106.00 125.00-180.00   84
  9  ω    -95.00 -27.00   0.50    0.05    --  -42.93 125.00 -90.00  136
 10  ω    -95.00 -70.00   0.50    0.05    -- -106.00  57.00-180.00   50
 11  ω   -125.00 -96.00   0.50    0.05    -- -106.00  57.00-180.00   58
 12  ω   -116.00 -84.00   0.50    0.05    -- -106.00 125.00-180.00   64
 13  ω   -128.00 -55.00   0.50    0.05    -- -106.00  57.00 -60.00  146
 14  ω    -69.00 -44.00   0.50    0.05    -- -106.00  57.00  30.00   50
 15  ω    -89.00 -50.00   0.50    0.05    -- -106.00 125.00 -60.00   78
 16  ω   -123.00 -84.00   0.50    0.05    -- -106.00  57.00  30.00   78
 17  ω    -90.00 -65.00   0.50    0.05    --  -42.93 -18.00   9.00   50
 18  ω    -77.00  10.00   0.50    0.05    --  -42.93  18.00 177.00  174
 19  ω   -132.00-102.00   0.50    0.05    -- -106.00 -37.00   0.00   60
 20  ω   -145.00 -95.00   0.50    0.05    -- -106.00 -77.00-120.00  100
 21  ω   -177.00-139.00   0.50    0.05    -- -106.00 -18.00   9.00   76
 22  ω   -174.00-135.00   0.50    0.05    -- -106.00 -37.00   0.00   78
 23  ω   -133.00 -25.00   0.50    0.05    -- -106.00  18.00 177.00  216
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0850796000
_diffrn_orient_matrix_UB_12      0.0040740000
_diffrn_orient_matrix_UB_13      0.0595459000
_diffrn_orient_matrix_UB_21      0.0946266000
_diffrn_orient_matrix_UB_22      -0.0746314000
_diffrn_orient_matrix_UB_23      0.0554197000
_diffrn_orient_matrix_UB_31      0.0236450000
_diffrn_orient_matrix_UB_32      0.3132959000
_diffrn_orient_matrix_UB_33      0.0123600000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1833
_reflns_number_total             2120
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.088
_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)+(0.0728P)²+0.1666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1297
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C9(H9A,H9B), C11(H11A,H11B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3)
;
_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
O16 O 0.32732(8) 0.3353(2) 0.51905(5) 0.0406(3) Uani 1 1 d . . . . .
N15 N 0.40785(9) -0.0006(2) 0.44574(6) 0.0353(3) Uani 1 1 d . . . . .
C5 C 0.46568(11) 0.3617(3) 0.60942(7) 0.0331(3) Uani 1 1 d . . . . .
C14 C 0.41241(11) 0.1545(3) 0.50391(7) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.45460(11) 0.6684(3) 0.71045(7) 0.0331(3) Uani 1 1 d . . . . .
C13 C 0.50034(11) -0.1609(3) 0.44266(6) 0.0329(3) Uani 1 1 d . . . . .
C6 C 0.51220(11) 0.4658(3) 0.67376(6) 0.0337(3) Uani 1 1 d . . . . .
H6 H 0.581151 0.399942 0.691828 0.040 Uiso 1 1 calc R . . . .
C4 C 0.36176(11) 0.4610(3) 0.58339(7) 0.0359(3) Uani 1 1 d . . . . .
C7 C 0.49958(11) 0.7892(3) 0.78110(7) 0.0330(3) Uani 1 1 d . . . . .
H7 H 0.481342 0.989073 0.780742 0.040 Uiso 1 1 calc R . . . .
C2 C 0.35034(12) 0.7626(3) 0.68201(7) 0.0398(3) Uani 1 1 d . . . . .
H2 H 0.311978 0.897903 0.706940 0.048 Uiso 1 1 calc R . . . .
C3 C 0.30212(12) 0.6623(3) 0.61828(8) 0.0421(4) Uani 1 1 d . . . . .
H3 H 0.233157 0.727552 0.600068 0.050 Uiso 1 1 calc R . . . .
C8 C 0.44062(13) 0.6582(3) 0.84394(7) 0.0427(4) Uani 1 1 d . . . . .
H8A H 0.360326 0.688410 0.837595 0.051 Uiso 1 1 calc R . . . .
H8B H 0.453865 0.458012 0.844298 0.051 Uiso 1 1 calc R . . . .
C12 C 0.62708(12) 0.7644(4) 0.79341(7) 0.0442(4) Uani 1 1 d . . . . .
H12A H 0.648383 0.568638 0.792427 0.053 Uiso 1 1 calc R . . . .
H12B H 0.663893 0.858974 0.755079 0.053 Uiso 1 1 calc R . . . .
C9 C 0.48183(14) 0.7812(4) 0.91537(7) 0.0496(4) Uani 1 1 d . . . . .
H9A H 0.460089 0.976439 0.917446 0.060 Uiso 1 1 calc R . . . .
H9B H 0.446274 0.683360 0.953692 0.060 Uiso 1 1 calc R . . . .
C11 C 0.66679(13) 0.8921(4) 0.86497(8) 0.0503(4) Uani 1 1 d . . . . .
H11A H 0.747274 0.866565 0.871824 0.060 Uiso 1 1 calc R . . . .
H11B H 0.651524 1.091426 0.864407 0.060 Uiso 1 1 calc R . . . .
C10 C 0.60839(14) 0.7582(4) 0.92621(8) 0.0503(4) Uani 1 1 d . . . . .
H10A H 0.632160 0.849487 0.970554 0.060 Uiso 1 1 calc R . . . .
H10B H 0.629570 0.562587 0.929749 0.060 Uiso 1 1 calc R . . . .


_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
O16 C14 1.3715(16) . ?
O16 C4 1.3929(15) . ?
N15 C14 1.3176(16) . ?
N15 C13 1.3460(17) . ?
C5 C13 1.4397(18) 3_656 ?
C5 C6 1.3966(17) . ?
C5 C4 1.3945(19) . ?
C14 C13 1.4120(18) 3_656 ?
C1 C6 1.3869(18) . ?
C1 C7 1.5205(17) . ?
C1 C2 1.405(2) . ?
C6 H6 0.9300 . ?
C4 C3 1.379(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.5316(18) . ?
C7 C12 1.532(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3878(19) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.5236(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.5296(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.517(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.511(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
C14 O16 C4 104.98(10) . . ?
C14 N15 C13 110.60(11) . . ?
C6 C5 C13 135.25(13) . 3_656 ?
C4 C5 C13 105.17(11) . 3_656 ?
C4 C5 C6 119.58(12) . . ?
O16 C14 C13 111.59(11) . 3_656 ?
N15 C14 O16 121.45(12) . . ?
N15 C14 C13 126.97(12) . 3_656 ?
C6 C1 C7 122.27(12) . . ?
C6 C1 C2 118.98(12) . . ?
C2 C1 C7 118.74(12) . . ?
N15 C13 C5 131.61(12) . 3_656 ?
N15 C13 C14 122.43(11) . 3_656 ?
C14 C13 C5 105.95(11) 3_656 3_656 ?
C5 C6 H6 120.3 . . ?
C1 C6 C5 119.38(12) . . ?
C1 C6 H6 120.3 . . ?
O16 C4 C5 112.30(11) . . ?
C3 C4 O16 124.99(12) . . ?
C3 C4 C5 122.71(12) . . ?
C1 C7 H7 107.1 . . ?
C1 C7 C8 110.99(11) . . ?
C1 C7 C12 114.28(11) . . ?
C8 C7 H7 107.1 . . ?
C8 C7 C12 109.78(11) . . ?
C12 C7 H7 107.1 . . ?
C1 C2 H2 118.6 . . ?
C3 C2 C1 122.81(13) . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 116.53(13) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 112.14(12) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C12 H12A 109.3 . . ?
C7 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C11 C12 C7 111.58(12) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 111.71(12) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C10 C11 C12 111.21(14) . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 C9 110.87(13) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?

_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 1.517
_oxdiff_exptl_absorpt_empirical_full_min 0.500
####################################################################### 
# 
# 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_220830_c117_6
_database_code_depnum_ccdc_archive 'CCDC 2305898'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N O'
_chemical_formula_sum            'C13 H14 N O'
_chemical_formula_weight         200.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H28 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 0.0181 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                   4.7285(3)
_cell_length_b                   8.2545(5)
_cell_length_c                   13.9117(10)
_cell_angle_alpha                95.036(5)
_cell_angle_beta                 91.036(5)
_cell_angle_gamma                96.682(4)
_cell_volume                     537.00(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1653
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9160
_cell_measurement_theta_min      5.4160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             214
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 1 0.0709
0 5 -3 0.0464
-3 0 -1 0.1518
0 -5 3 0.0265
0 -1 9 0.0093
0 1 -9 0.0167

_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.026
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.9980 0.0563 1.3034 -0.0767 -0.3220 0.9436
-0.0601 5.1967 -2.8141 0.2149 0.8953 0.3903
-3.0082 0.2973 -1.4975 0.0915 0.3836 -0.9190
-0.0070 -5.1893 2.7803 -0.2128 -0.8866 -0.4107
-0.0808 -0.8403 9.0072 -0.9832 -0.1825 -0.0088
0.0808 0.8403 -9.0072 0.9832 0.1825 0.0088

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5319
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.345
_diffrn_reflns_theta_min         5.418
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     78.00 151.00   0.50    1.13    --   76.50  57.00  30.00  146
  2  ω    101.00 127.00   0.50    1.13    --   76.50 124.00  42.00   52
  3  ω     73.00 116.00   0.50    0.28    --   42.80 125.00  60.00   86
  4  ω     89.00 120.00   0.50    1.13    --   76.50  57.00 150.00   62
  5  ω    125.00 151.00   0.50    1.13    --   76.50  57.00 150.00   52
  6  ω     58.00  86.00   0.50    1.13    --   76.50  57.00 150.00   56
  7  ω     39.00  95.00   0.50    0.28    --   42.80-124.00 -37.00  112
  8  ω     38.00  63.00   0.50    1.13    --   76.50-124.00 -37.00   50
  9  ω     66.00 109.00   0.50    0.28    --   42.80-148.00 158.00   86
 10  ω     77.00 102.00   0.50    1.13    --   76.50-148.00 158.00   50
 11  ω    -74.00 -34.00   0.50    1.13    -- -106.00  77.00-120.00   80
 12  ω    -60.00 -35.00   0.50    1.13    -- -106.00  57.00 -90.00   50
 13  ω    -90.00 -64.00   0.50    1.13    -- -106.00 125.00 -90.00   52
 14  ω    -57.00 -32.00   0.50    1.13    -- -106.00 125.00-150.00   50
 15  ω    -76.00 -50.00   0.50    0.28    --  -42.80 148.00-153.00   52
 16  ω   -112.00 -78.00   0.50    1.13    -- -106.00  57.00 -90.00   68
 17  ω   -116.00 -66.00   0.50    1.13    -- -106.00 125.00-150.00  100
 18  ω   -133.00 -90.00   0.50    1.13    -- -106.00 148.00-153.00   86
 19  ω   -134.00 -80.00   0.50    1.13    -- -106.00  77.00-120.00  108
 20  ω   -110.00 -35.00   0.50    1.13    -- -106.00 125.00   0.00  150
 21  ω    -59.00 -31.00   0.50    0.28    --  -42.80 124.00  42.00   56
 22  ω     73.00  98.00   0.50    0.28    --   42.80 125.00-120.00   50
 23  ω     56.00 107.00   0.50    0.28    --   42.80 148.00-153.00  102
 24  ω     86.00 112.00   0.50    1.13    --   76.50 148.00-153.00   52
 25  ω   -101.00 -76.00   0.50    1.13    -- -106.00 124.00  42.00   50
 26  ω   -125.00 -73.00   0.50    1.13    -- -106.00  57.00  90.00  104
 27  ω   -128.00 -28.00   0.50    1.13    -- -106.00  37.00  90.00  200
 28  ω   -114.00 -77.00   0.50    1.13    -- -106.00 -77.00 150.00   74
 29  ω   -133.00-108.00   0.50    1.13    -- -106.00-148.00 158.00   50
 30  ω   -151.00-121.00   0.50    1.13    -- -106.00 -77.00 150.00   60
 31  ω   -177.00 -83.00   0.50    1.13    -- -106.00 -57.00  90.00  188
 32  ω    -95.00 -70.00   0.50    0.28    --  -42.80-148.00 158.00   50
 33  ω   -112.00 -84.00   0.50    0.28    --  -42.80-125.00  60.00   56
 34  ω   -147.00 -99.00   0.50    1.13    -- -106.00-124.00 -37.00   96
 35  ω   -114.00 -70.00   0.50    0.28    --  -42.80-125.00-150.00   88
 36  ω   -167.00 -85.00   0.50    1.13    -- -106.00 -99.00-180.00  164
 37  ω   -173.00-115.00   0.50    1.13    -- -106.00 -37.00  30.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228618000
_diffrn_orient_matrix_UB_12      -0.0183066000
_diffrn_orient_matrix_UB_13      -0.1106568000
_diffrn_orient_matrix_UB_21      -0.1081421000
_diffrn_orient_matrix_UB_22      0.1680162000
_diffrn_orient_matrix_UB_23      -0.0055551000
_diffrn_orient_matrix_UB_31      0.3089923000
_diffrn_orient_matrix_UB_32      0.0838877000
_diffrn_orient_matrix_UB_33      0.0096207000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1558
_reflns_number_total             2100
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0690
_refine_ls_restrained_S_all      1.154
_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)+(0.0500P)²+0.4275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2051
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
O10 O 0.9018(4) 0.8092(3) 0.00644(15) 0.0551(6) Uani 1 1 d . . . . .
N9 N 1.1494(5) 0.6048(3) -0.06738(17) 0.0497(6) Uani 1 1 d . . . . .
C8 C 0.9678(6) 0.6513(4) -0.0031(2) 0.0476(7) Uani 1 1 d . . . . .
C7 C 1.1822(6) 0.4456(4) -0.0629(2) 0.0469(7) Uani 1 1 d . . . . .
C1 C 0.6509(6) 0.6620(4) 0.1181(2) 0.0475(7) Uani 1 1 d . . . . .
C6 C 0.7132(6) 0.8147(4) 0.0817(2) 0.0495(7) Uani 1 1 d . . . . .
C2 C 0.4613(6) 0.6464(4) 0.1936(2) 0.0514(7) Uani 1 1 d . . . . .
H2 H 0.415618 0.545533 0.217927 0.062 Uiso 1 1 calc R . . . .
C3 C 0.3416(6) 0.7832(4) 0.2319(2) 0.0525(8) Uani 1 1 d . . . . .
C5 C 0.5965(7) 0.9519(4) 0.1172(2) 0.0579(8) Uani 1 1 d . . . . .
H5 H 0.639976 1.052196 0.092024 0.069 Uiso 1 1 calc R . . . .
C4 C 0.4113(7) 0.9333(4) 0.1922(2) 0.0580(8) Uani 1 1 d . . . . .
H4 H 0.328937 1.024086 0.217651 0.070 Uiso 1 1 calc R . . . .
C11 C 0.1517(7) 0.7724(5) 0.3181(2) 0.0594(8) Uani 1 1 d . . . . .
H11A H 0.012783 0.676057 0.306809 0.071 Uiso 1 1 calc R . . . .
H11B H 0.048756 0.867604 0.324275 0.071 Uiso 1 1 calc R . . . .
C13 C 0.1315(7) 0.7513(4) 0.4995(2) 0.0604(8) Uani 1 1 d . . . . .
H13A H 0.041211 0.850789 0.509780 0.072 Uiso 1 1 calc R . . . .
H13B H -0.018151 0.660798 0.486093 0.072 Uiso 1 1 calc R . . . .
C12 C 0.3157(7) 0.7631(5) 0.4119(2) 0.0635(9) Uani 1 1 d . . . . .
H12A H 0.419744 0.668373 0.405063 0.076 Uiso 1 1 calc R . . . .
H12B H 0.454169 0.859665 0.422805 0.076 Uiso 1 1 calc R . . . .
C14 C 0.2892(9) 0.7266(5) 0.5908(3) 0.0745(10) Uani 1 1 d . . . . .
H14A H 0.439184 0.816978 0.604132 0.089 Uiso 1 1 calc R . . . .
H14B H 0.379177 0.626987 0.580573 0.089 Uiso 1 1 calc R . . . .
C15 C 0.1063(10) 0.7152(6) 0.6780(3) 0.0841(12) Uani 1 1 d . . . . .
H15A H -0.041793 0.625372 0.666068 0.126 Uiso 1 1 calc GR . . . .
H15B H 0.022746 0.815241 0.690712 0.126 Uiso 1 1 calc GR . . . .
H15C H 0.221372 0.697819 0.732888 0.126 Uiso 1 1 calc GR . . . .


_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
O10 C8 1.371(4) . ?
O10 C6 1.389(3) . ?
N9 C8 1.315(4) . ?
N9 C7 1.348(4) . ?
C8 C7 1.417(4) 2_765 ?
C7 C1 1.438(4) 2_765 ?
C1 C6 1.401(4) . ?
C1 C2 1.398(4) . ?
C6 C5 1.374(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C3 C4 1.407(5) . ?
C3 C11 1.513(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(4) . ?
C4 H4 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.518(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.514(4) . ?
C13 C14 1.503(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.506(5) . ?
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
C8 O10 C6 105.2(2) . . ?
C8 N9 C7 110.5(2) . . ?
O10 C8 C7 111.5(2) . 2_765 ?
N9 C8 O10 121.1(3) . . ?
N9 C8 C7 127.4(3) . 2_765 ?
N9 C7 C8 122.0(3) . 2_765 ?
N9 C7 C1 132.0(3) . 2_765 ?
C8 C7 C1 105.9(3) 2_765 2_765 ?
C6 C1 C7 105.2(2) . 2_765 ?
C2 C1 C7 135.5(3) . 2_765 ?
C2 C1 C6 119.3(3) . . ?
O10 C6 C1 112.2(3) . . ?
C5 C6 O10 125.0(3) . . ?
C5 C6 C1 122.8(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 C11 120.4(3) . . ?
C4 C3 C11 120.7(3) . . ?
C6 C5 H5 121.7 . . ?
C6 C5 C4 116.7(3) . . ?
C4 C5 H5 121.7 . . ?
C3 C4 H4 118.5 . . ?
C5 C4 C3 123.0(3) . . ?
C5 C4 H4 118.5 . . ?
C3 C11 H11A 109.0 . . ?
C3 C11 H11B 109.0 . . ?
C3 C11 C12 113.0(3) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H13A C13 H13B 107.6 . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C14 C13 C12 114.5(3) . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 C11 114.3(3) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C13 C14 C15 114.5(3) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 2.423
_oxdiff_exptl_absorpt_empirical_full_min 0.620
####################################################################### 
# 
# 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_221101_c118_1
_database_code_depnum_ccdc_archive 'CCDC 2305900'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 N O'
_chemical_formula_sum            'C14 H16 N O'
_chemical_formula_weight         214.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H32 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 0.0181 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                   4.6872(4)
_cell_length_b                   8.1370(6)
_cell_length_c                   15.3378(7)
_cell_angle_alpha                88.441(5)
_cell_angle_beta                 87.919(5)
_cell_angle_gamma                85.811(6)
_cell_volume                     582.86(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2822
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7770
_cell_measurement_theta_min      5.7620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             230
_exptl_crystal_size_max          0.629
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6945
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.419
_diffrn_reflns_theta_min         5.453
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  12.00   0.50    0.17    --  -42.80  77.00  60.00  160
  2  ω    -50.00 -25.00   0.50    0.69    -- -106.00  19.00  30.00   50
  3  ω    -66.00 -33.00   0.50    0.69    -- -106.00  77.00  90.00   66
  4  ω    -64.00 -38.00   0.50    0.69    -- -106.00  57.00  90.00   52
  5  ω    -67.00 -33.00   0.50    0.69    -- -106.00 125.00  90.00   68
  6  ω    -65.00 -28.00   0.50    0.17    --  -42.80 106.00  51.00   74
  7  ω    -53.00 -27.00   0.50    0.69    -- -106.00   0.00 -60.00   52
  8  ω    -75.00 -30.00   0.50    0.69    -- -106.00  37.00 -60.00   90
  9  ω    -85.00 -59.00   0.50    0.69    -- -106.00  77.00 -90.00   52
 10  ω    -85.00 -59.00   0.50    0.69    -- -106.00  37.00 -90.00   52
 11  ω    -85.00 -59.00   0.50    0.69    -- -106.00  77.00-120.00   52
 12  ω   -102.00 -75.00   0.50    0.69    -- -106.00 125.00 -90.00   54
 13  ω   -116.00 -68.00   0.50    0.69    -- -106.00 125.00 -60.00   96
 14  ω   -108.00 -31.00   0.50    0.69    -- -106.00  95.00 -70.42  154
 15  ω    -65.00 -38.00   0.50    0.69    -- -106.00 125.00-180.00   54
 16  ω   -107.00 -82.00   0.50    0.69    -- -106.00 125.00-120.00   50
 17  ω   -111.00 -81.00   0.50    0.69    -- -106.00 125.00-180.00   60
 18  ω   -115.00 -90.00   0.50    0.69    -- -106.00  90.00-105.76   50
 19  ω   -112.00 -86.00   0.50    0.69    -- -106.00  57.00-150.00   52
 20  ω   -123.00 -97.00   0.50    0.69    -- -106.00  77.00 -90.00   52
 21  ω   -127.00 -86.00   0.50    0.69    -- -106.00  57.00-120.00   82
 22  ω   -126.00-100.00   0.50    0.69    -- -106.00  37.00 -90.00   52
 23  ω   -128.00 -96.00   0.50    0.69    -- -106.00  37.00 -60.00   64
 24  ω   -130.00 -98.00   0.50    0.69    -- -106.00  83.00 -83.19   64
 25  ω   -127.00 -81.00   0.50    0.69    -- -106.00  30.00-161.48   92
 26  ω   -135.00 -75.00   0.50    0.69    -- -106.00 -19.00 -60.00  120
 27  ω   -101.00 -76.00   0.50    0.69    -- -106.00 -19.00   0.00   50
 28  ω   -100.00 -74.00   0.50    0.69    -- -106.00  19.00  30.00   52
 29  ω    -92.00 -51.00   0.50    0.69    -- -106.00  57.00  30.00   82
 30  ω   -101.00 -76.00   0.50    0.69    -- -106.00 106.00  51.00   50
 31  ω   -116.00 -69.00   0.50    0.69    -- -106.00 125.00  60.00   94
 32  ω   -119.00 -87.00   0.50    0.69    -- -106.00  77.00  90.00   64
 33  ω   -114.00 -65.00   0.50    0.69    -- -106.00  37.00  60.00   98
 34  ω   -116.00 -86.00   0.50    0.69    -- -106.00 125.00  90.00   60
 35  ω   -133.00 -35.00   0.50    0.69    -- -106.00  91.00   9.78  196
 36  ω   -154.00-129.00   0.50    0.69    -- -106.00 -19.00   0.00   50
 37  ω   -164.00 -85.00   0.50    0.69    -- -106.00 -57.00  30.00  158
 38  ω   -138.00 -95.00   0.50    0.69    -- -106.00-106.00 -47.00   86
 39  ω   -161.00-122.00   0.50    0.69    -- -106.00-125.00   0.00   78
 40  ω   -168.00-131.00   0.50    0.69    -- -106.00 -57.00  60.00   74
 41  ω   -161.00-115.00   0.50    0.69    -- -106.00-125.00 120.00   92
 42  ω   -172.00-119.00   0.50    0.69    -- -106.00   0.00 -60.00  106
 43  ω     -3.00  69.00   0.50    0.17    --   42.80-106.00 -47.00  144
 44  ω     32.00  57.00   0.50    0.69    --   76.50-106.00 -47.00   50
 45  ω     84.00 118.00   0.50    0.69    --   76.50 106.00  51.00   68
 46  ω    113.00 148.00   0.50    0.69    --   76.50 125.00   0.00   70
 47  ω     71.00 115.00   0.50    0.17    --   42.80 125.00 150.00   88
 48  ω     73.00 115.00   0.50    0.17    --   42.80 125.00   0.00   84
 49  ω     71.00 115.00   0.50    0.17    --   42.80 125.00 -60.00   88
 50  ω     74.00  99.00   0.50    0.17    --   42.80 125.00-120.00   50
 51  ω     75.00 115.00   0.50    0.17    --   42.80 125.00-150.00   80
 52  ω     71.00  96.00   0.50    0.17    --   42.80 125.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0020717000
_diffrn_orient_matrix_UB_12      0.0524713000
_diffrn_orient_matrix_UB_13      -0.0972756000
_diffrn_orient_matrix_UB_21      -0.3248496000
_diffrn_orient_matrix_UB_22      -0.0174114000
_diffrn_orient_matrix_UB_23      -0.0015256000
_diffrn_orient_matrix_UB_31      -0.0565963000
_diffrn_orient_matrix_UB_32      0.1816669000
_diffrn_orient_matrix_UB_33      0.0253610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1811
_reflns_number_total             2310
_reflns_odcompleteness_completeness 97.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.054
_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)+(0.1807P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1915
_refine_ls_wR_factor_ref         0.2382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
O10 O 0.8935(3) 0.18593(16) 0.00742(8) 0.0510(4) Uani 1 1 d . . . . .
N9 N 1.1593(3) 0.38835(19) -0.06058(9) 0.0466(4) Uani 1 1 d . . . . .
C8 C 0.9634(4) 0.3456(2) -0.00215(11) 0.0434(5) Uani 1 1 d . . . . .
C7 C 1.1945(4) 0.5504(2) -0.05754(10) 0.0448(5) Uani 1 1 d . . . . .
C1 C 0.6251(4) 0.3443(2) 0.10782(11) 0.0452(5) Uani 1 1 d . . . . .
C6 C 0.6887(4) 0.1875(2) 0.07544(11) 0.0470(5) Uani 1 1 d . . . . .
C2 C 0.4206(4) 0.3678(2) 0.17630(11) 0.0478(5) Uani 1 1 d . . . . .
H2 H 0.373752 0.472231 0.198111 0.057 Uiso 1 1 calc R . . . .
C3 C 0.2896(4) 0.2311(3) 0.21082(12) 0.0495(5) Uani 1 1 d . . . . .
C5 C 0.5630(4) 0.0484(3) 0.10760(13) 0.0541(5) Uani 1 1 d . . . . .
H5 H 0.609786 -0.055654 0.085342 0.065 Uiso 1 1 calc R . . . .
C4 C 0.3618(4) 0.0754(3) 0.17558(13) 0.0546(5) Uani 1 1 d . . . . .
H4 H 0.270322 -0.014277 0.198898 0.066 Uiso 1 1 calc R . . . .
C12 C 0.2407(4) 0.2354(3) 0.37445(12) 0.0541(5) Uani 1 1 d . . . . .
H12A H 0.353451 0.130711 0.377035 0.065 Uiso 1 1 calc R . . . .
H12B H 0.371809 0.322204 0.375052 0.065 Uiso 1 1 calc R . . . .
C13 C 0.0433(4) 0.2484(3) 0.45506(12) 0.0553(5) Uani 1 1 d . . . . .
H13A H -0.080575 0.157885 0.456400 0.066 Uiso 1 1 calc R . . . .
H13B H -0.076966 0.350336 0.451125 0.066 Uiso 1 1 calc R . . . .
C11 C 0.0837(4) 0.2485(3) 0.28871(13) 0.0550(5) Uani 1 1 d . . . . .
H11A H -0.049803 0.162938 0.287934 0.066 Uiso 1 1 calc R . . . .
H11B H -0.025179 0.354301 0.284841 0.066 Uiso 1 1 calc R . . . .
C14 C 0.2036(4) 0.2447(3) 0.53956(13) 0.0581(6) Uani 1 1 d . . . . .
H14A H 0.322430 0.142181 0.543505 0.070 Uiso 1 1 calc R . . . .
H14B H 0.329483 0.334274 0.537606 0.070 Uiso 1 1 calc R . . . .
C15 C 0.0112(5) 0.2595(3) 0.62092(14) 0.0636(6) Uani 1 1 d . . . . .
H15A H -0.110715 0.360741 0.616584 0.076 Uiso 1 1 calc R . . . .
H15B H -0.111476 0.168326 0.623834 0.076 Uiso 1 1 calc R . . . .
C16 C 0.1746(7) 0.2595(4) 0.70430(16) 0.0829(8) Uani 1 1 d . . . . .
H16A H 0.297122 0.349158 0.701890 0.124 Uiso 1 1 calc GR . . . .
H16B H 0.288446 0.157170 0.710629 0.124 Uiso 1 1 calc GR . . . .
H16C H 0.041953 0.272142 0.753233 0.124 Uiso 1 1 calc GR . . . .


_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
O10 C8 1.365(2) . ?
O10 C6 1.391(2) . ?
N9 C8 1.318(2) . ?
N9 C7 1.343(2) . ?
C8 C7 1.416(2) 2_765 ?
C7 C1 1.438(2) 2_765 ?
C1 C6 1.389(3) . ?
C1 C2 1.403(2) . ?
C6 C5 1.385(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(3) . ?
C3 C4 1.405(3) . ?
C3 C11 1.511(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.391(3) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.518(2) . ?
C12 C11 1.527(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.520(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.515(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.515(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O10 C6 104.86(13) . . ?
C8 N9 C7 110.70(15) . . ?
O10 C8 C7 111.77(15) . 2_765 ?
N9 C8 O10 121.17(16) . . ?
N9 C8 C7 127.06(17) . 2_765 ?
N9 C7 C8 122.24(15) . 2_765 ?
N9 C7 C1 132.15(16) . 2_765 ?
C8 C7 C1 105.60(16) 2_765 2_765 ?
C6 C1 C7 105.28(15) . 2_765 ?
C6 C1 C2 119.80(17) . . ?
C2 C1 C7 134.92(18) . 2_765 ?
C1 C6 O10 112.48(15) . . ?
C5 C6 O10 123.84(17) . . ?
C5 C6 C1 123.68(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.42(18) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.43(17) . . ?
C2 C3 C11 120.29(18) . . ?
C4 C3 C11 120.20(18) . . ?
C6 C5 H5 122.4 . . ?
C6 C5 C4 115.24(19) . . ?
C4 C5 H5 122.4 . . ?
C3 C4 H4 118.3 . . ?
C5 C4 C3 123.41(18) . . ?
C5 C4 H4 118.3 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C13 C12 C11 113.81(16) . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C12 C13 C14 113.08(16) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C3 C11 C12 111.58(16) . . ?
C3 C11 H11A 109.3 . . ?
C3 C11 H11B 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.06(17) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.3(2) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.251
_oxdiff_exptl_absorpt_empirical_full_min 0.225
####################################################################### 
# 
# 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_220711_c86_block_1
_database_code_depnum_ccdc_archive 'CCDC 2305902'
loop_
_audit_author_name
_audit_author_address
'Shotaro Nakamura'
;Osaka University
Japan
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N O'
_chemical_formula_sum            'C14 H14 N O'
_chemical_formula_weight         212.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H28 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      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                   5.2466(2)
_cell_length_b                   5.2604(2)
_cell_length_c                   20.0763(9)
_cell_angle_alpha                90.874(3)
_cell_angle_beta                 92.964(3)
_cell_angle_gamma                102.471(3)
_cell_volume                     540.09(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9300
_cell_measurement_theta_min      3.0490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             226
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 7 -1 0.1580
6 2 8 0.1404
0 -7 -1 0.1024
-3 7 1 0.2588
1 -1 -28 0.0948
3 -7 -7 0.1410
-1 -1 28 0.1136

_exptl_crystal_size_max          1.16
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.272
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0578 7.3955 -0.8255 0.0532 0.2259 0.9727
6.0110 2.1341 8.0083 0.2310 0.9651 0.1231
-0.0794 -7.2144 -0.6457 -0.0899 -0.3787 -0.9212
-2.7689 7.3081 0.9610 0.1345 -0.0044 0.9909
1.4678 -1.0076 -27.7807 -0.9974 0.0256 -0.0676
2.9049 -7.0298 -7.0695 -0.3470 0.0098 -0.9378
-0.7801 -0.8631 28.0721 0.9820 -0.0249 -0.1874

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.801
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8213
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.143
_diffrn_reflns_theta_min         2.032
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.801
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -23.00   0.50    1.02    --   -8.66 123.00  47.00   54
  2  ω    -63.00 -37.00   0.50    1.02    --   -8.66 150.00-149.00   52
  3  ω     24.00  76.00   0.50    1.02    --    9.13-150.00 164.00  104
  4  ω     28.00  55.00   0.50    1.02    --    9.13-123.00 -33.00   54
  5  ω    -24.00  25.00   0.50    1.02    --   -8.66 -99.00  60.00   98
  6  ω    -25.00  16.00   0.50    1.02    --   -8.66 -99.00 -30.00   82
  7  ω    -13.00  83.00   0.50    1.02    --    9.13  57.00  30.00  192
  8  ω    -25.00  12.00   0.50    1.02    --    9.13 -99.00 -60.00   74
  9  ω     14.00  39.00   0.50    1.02    --    9.13 -99.00 -60.00   50
 10  ω    -22.00  48.00   0.50    1.02    --    9.13 -99.00-120.00  140
 11  ω    -58.00  27.00   0.50    1.02    --    9.13 -57.00-120.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0114955000
_diffrn_orient_matrix_UB_12      0.0094562000
_diffrn_orient_matrix_UB_13      0.0349517000
_diffrn_orient_matrix_UB_21      0.1366546000
_diffrn_orient_matrix_UB_22      0.0505825000
_diffrn_orient_matrix_UB_23      0.0044647000
_diffrn_orient_matrix_UB_31      -0.0206332000
_diffrn_orient_matrix_UB_32      0.1282063000
_diffrn_orient_matrix_UB_33      -0.0033060000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1976
_reflns_number_total             2557
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.082
_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)+(0.0891P)²+0.0523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1594
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3)
;
_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
O16 O 0.3248(2) 0.1861(2) 0.51998(5) 0.0400(3) Uani 1 1 d . . . . .
N15 N 0.0678(2) 0.3613(2) 0.44219(6) 0.0367(3) Uani 1 1 d . . . . .
C6 C 0.2671(3) 0.4415(3) 0.68507(7) 0.0347(3) Uani 1 1 d . . . . .
H6 H 0.178588 0.556632 0.704329 0.042 Uiso 1 1 calc R . . . .
C14 C 0.1549(3) 0.3432(3) 0.50405(7) 0.0344(4) Uani 1 1 d . . . . .
C5 C 0.2383(3) 0.3888(3) 0.61648(7) 0.0342(3) Uani 1 1 d . . . . .
C1 C 0.4288(3) 0.3206(3) 0.72434(7) 0.0347(4) Uani 1 1 d . . . . .
C13 C -0.0947(3) 0.5265(3) 0.43876(7) 0.0339(4) Uani 1 1 d . . . . .
C7 C 0.4659(3) 0.3757(3) 0.79874(7) 0.0347(3) Uani 1 1 d . . . . .
H7 H 0.357094 0.498655 0.809629 0.042 Uiso 1 1 calc R . . . .
C4 C 0.3721(3) 0.2146(3) 0.58867(7) 0.0357(4) Uani 1 1 d . . . . .
C2 C 0.5591(3) 0.1464(3) 0.69355(8) 0.0404(4) Uani 1 1 d . . . . .
H2 H 0.667212 0.065795 0.720061 0.049 Uiso 1 1 calc R . . . .
C3 C 0.5336(3) 0.0901(3) 0.62600(8) 0.0409(4) Uani 1 1 d . . . . .
H3 H 0.620836 -0.025810 0.606612 0.049 Uiso 1 1 calc R . . . .
C8 C 0.7483(3) 0.5057(3) 0.82026(8) 0.0439(4) Uani 1 1 d . . . . .
H8A H 0.862486 0.392678 0.807731 0.053 Uiso 1 1 calc R . . . .
H8B H 0.798376 0.667280 0.796852 0.053 Uiso 1 1 calc R . . . .
C12 C 0.3751(3) 0.1326(3) 0.83938(8) 0.0433(4) Uani 1 1 d . . . . .
H12A H 0.191448 0.060828 0.828022 0.052 Uiso 1 1 calc R . . . .
H12B H 0.472160 0.002565 0.827611 0.052 Uiso 1 1 calc R . . . .
C9 C 0.7852(4) 0.5629(3) 0.89494(9) 0.0499(4) Uani 1 1 d . . . . .
H9A H 0.968597 0.634786 0.906650 0.060 Uiso 1 1 calc R . . . .
H9B H 0.687258 0.692122 0.906793 0.060 Uiso 1 1 calc R . . . .
C10 C 0.6941(4) 0.3191(3) 0.93424(8) 0.0487(4) Uani 1 1 d . . . . .
H10A H 0.805506 0.197775 0.926476 0.058 Uiso 1 1 calc R . . . .
H10B H 0.708985 0.364217 0.981518 0.058 Uiso 1 1 calc R . . . .
C11 C 0.4134(4) 0.1903(4) 0.91409(8) 0.0492(4) Uani 1 1 d . . . . .
H11A H 0.299824 0.303628 0.926849 0.059 Uiso 1 1 calc R . . . .
H11B H 0.364304 0.028985 0.937680 0.059 Uiso 1 1 calc R . . . .


_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
O16 C14 1.3698(16) . ?
O16 C4 1.3886(17) . ?
N15 C14 1.3130(19) . ?
N15 C13 1.3421(17) . ?
C6 H6 0.9300 . ?
C6 C5 1.394(2) . ?
C6 C1 1.387(2) . ?
C14 C13 1.413(2) 2_566 ?
C5 C13 1.439(2) 2_566 ?
C5 C4 1.396(2) . ?
C1 C7 1.512(2) . ?
C1 C2 1.409(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.528(2) . ?
C7 C12 1.529(2) . ?
C4 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.519(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.520(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.517(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.513(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
C14 O16 C4 105.34(11) . . ?
C14 N15 C13 110.66(13) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C1 C6 C5 119.44(13) . . ?
O16 C14 C13 111.40(12) . 2_566 ?
N15 C14 O16 121.32(13) . . ?
N15 C14 C13 127.28(13) . 2_566 ?
C6 C5 C13 135.43(13) . 2_566 ?
C6 C5 C4 119.32(13) . . ?
C4 C5 C13 105.25(13) . 2_566 ?
C6 C1 C7 120.66(13) . . ?
C6 C1 C2 118.78(14) . . ?
C2 C1 C7 120.56(12) . . ?
N15 C13 C14 122.06(13) . 2_566 ?
N15 C13 C5 132.03(13) . 2_566 ?
C14 C13 C5 105.91(12) 2_566 2_566 ?
C1 C7 H7 107.2 . . ?
C1 C7 C8 112.24(13) . . ?
C1 C7 C12 112.73(12) . . ?
C8 C7 H7 107.2 . . ?
C8 C7 C12 110.03(12) . . ?
C12 C7 H7 107.2 . . ?
O16 C4 C5 112.10(12) . . ?
C3 C4 O16 124.96(13) . . ?
C3 C4 C5 122.94(14) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 C1 123.02(13) . . ?
C3 C2 H2 118.5 . . ?
C4 C3 C2 116.50(14) . . ?
C4 C3 H3 121.8 . . ?
C2 C3 H3 121.8 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 112.25(14) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C12 H12A 109.1 . . ?
C7 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C11 C12 C7 112.28(13) . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.48(14) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.10(13) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 C12 111.58(14) . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?

_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.863
