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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_181107_hk_scaffold
_database_code_depnum_ccdc_archive 'CCDC 2179518'
loop_
_audit_author_name
_audit_author_address
'Toshiaki Wayama'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-06-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
toshiakiw@g.ecc.u-tokyo.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        50619WayamaKaneko
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H14N2O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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                   9.6012(6)
_cell_length_b                   8.8018(5)
_cell_length_c                   16.4194(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.399(6)
_cell_angle_gamma                90
_cell_volume                     1355.20(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3643
_cell_measurement_temperature    170
_cell_measurement_theta_max      32.2430
_cell_measurement_theta_min      3.1640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 10 2 0.1044
0 11 -12 0.0835
-7 -10 -2 0.0913
1 -3 22 0.2672
10 -4 -17 0.1241
-2 4 -21 0.1877
-11 7 1 0.1387
0 -3 22 0.2669
10 -4 -17 0.1272
0 3 -22 0.1896
-6 6 -15 0.1772
-7 -11 0 0.0818
8 9 5 0.1324
11 -7 1 0.1937
13 1 -13 0.1207
6 -5 16 0.2415
-10 6 16 0.1011

_exptl_crystal_preparation       'vapor difussion'
_exptl_crystal_recrystallization_method 'vapor difussion'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.188
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
7.2592 10.1139 2.3153 -0.0000 -0.9995 0.0312
0.3583 10.6373 -11.7299 -0.0000 -0.6247 -0.7809
-7.0996 -10.2873 -1.8020 0.0000 1.0000 0.0000
0.6358 -3.1829 21.5818 0.4027 0.0000 0.9153
9.9983 -4.0632 -17.0143 -0.9986 -0.0000 -0.0526
-1.9502 3.8667 -20.5044 -0.2953 0.0000 -0.9554
-11.1796 6.8268 1.3291 0.7526 -0.0000 -0.6585
0.3213 -3.0138 21.7967 0.4276 0.0000 0.9040
10.1497 -4.2130 -16.5880 -0.9997 0.0000 -0.0256
-0.0692 2.8767 -21.9571 -0.4472 -0.0000 -0.8944
-6.3249 5.8403 -14.5766 0.1104 0.0000 -0.9939
-6.6607 -10.6846 -0.4834 0.0000 0.9968 0.0797
7.8933 9.2038 4.6129 -0.0000 -0.9850 0.1724
11.0000 -7.0000 1.0000 -0.6926 -0.0010 0.7409
13.0000 1.0000 -13.0000 -0.8996 -0.4985 0.0395
6.0000 -5.0000 16.0000 -0.0369 -0.0548 1.0021
-10.0000 6.0000 16.0000 1.0289 -0.1206 -0.0520

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8738
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.640
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   25.59    --   30.00  54.00-120.00  193
  2  ω     29.00  55.00   1.00   25.59    --   30.00  54.00-120.00   26
  3  ω     -6.00 113.00   1.00   25.59    --   30.00  54.00  90.00  119
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2332
_reflns_number_total             3051
_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 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.051
_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)+(0.0496P)²+0.1907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00B(H00C,H00D), C00E(H00G,H00H)
2.b Aromatic/amide H refined with riding coordinates:
 N002(H002), C00C(H00E), C00D(H00F), C00H(H00K), C00I(H00L)
2.c X=CH2 refined with riding coordinates:
 C00G(H00I,H00J)
2.d :
 C00J(H00M)
;
_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
O001 O 0.08087(9) 0.50222(11) 0.66949(6) 0.0334(2) Uani 1 1 d . . . . .
N002 N 0.19784(11) 0.43128(12) 0.41909(6) 0.0270(2) Uani 1 1 d . . . . .
H002 H 0.125320 0.481904 0.392908 0.032 Uiso 1 1 calc R U . . .
N003 N 0.31358(11) 0.44147(12) 0.68963(7) 0.0270(2) Uani 1 1 d . . . . .
C004 C 0.19184(13) 0.49621(13) 0.64268(8) 0.0253(3) Uani 1 1 d . . . . .
C005 C 0.19375(12) 0.54576(14) 0.55547(8) 0.0252(3) Uani 1 1 d . . . . .
C006 C 0.38568(13) 0.27165(14) 0.44751(8) 0.0273(3) Uani 1 1 d . . . . .
C007 C 0.25854(12) 0.44313(14) 0.50332(8) 0.0248(3) Uani 1 1 d . . . . .
C008 C 0.27249(13) 0.32540(14) 0.38421(8) 0.0268(3) Uani 1 1 d . . . . .
C009 C 0.37536(12) 0.34818(14) 0.52310(8) 0.0264(3) Uani 1 1 d . . . . .
C00A C 0.31021(14) 0.37623(15) 0.77109(8) 0.0301(3) Uani 1 1 d . . . . .
H00A H 0.384928 0.300496 0.785044 0.036 Uiso 1 1 calc R U . . .
H00B H 0.219538 0.325346 0.767744 0.036 Uiso 1 1 calc R U . . .
C00B C 0.45236(13) 0.45818(15) 0.66603(8) 0.0297(3) Uani 1 1 d . . . . .
H00C H 0.527715 0.453560 0.715890 0.036 Uiso 1 1 calc R U . . .
H00D H 0.456696 0.557179 0.640741 0.036 Uiso 1 1 calc R U . . .
C00C C 0.25205(14) 0.27594(15) 0.30172(9) 0.0332(3) Uani 1 1 d . . . . .
H00E H 0.176748 0.312014 0.260888 0.040 Uiso 1 1 calc R U . . .
C00D C 0.48181(14) 0.16551(15) 0.42638(9) 0.0328(3) Uani 1 1 d . . . . .
H00F H 0.557623 0.128838 0.466668 0.039 Uiso 1 1 calc R U . . .
C00E C 0.47791(13) 0.33627(15) 0.60550(8) 0.0312(3) Uani 1 1 d . . . . .
H00G H 0.574512 0.345366 0.597067 0.037 Uiso 1 1 calc R U . . .
H00H H 0.468488 0.237027 0.629433 0.037 Uiso 1 1 calc R U . . .
C00F C 0.32946(15) 0.49041(16) 0.83794(9) 0.0355(3) Uani 1 1 d . . . . .
C00G C 0.12435(14) 0.67140(15) 0.52559(9) 0.0326(3) Uani 1 1 d . . . . .
H00I H 0.115349 0.697211 0.469781 0.039 Uiso 1 1 calc R U . . .
H00J H 0.084796 0.733479 0.560507 0.039 Uiso 1 1 calc R U . . .
C00H C 0.34761(16) 0.17165(16) 0.28305(10) 0.0388(3) Uani 1 1 d . . . . .
H00K H 0.336576 0.136807 0.228569 0.047 Uiso 1 1 calc R U . . .
C00I C 0.46141(15) 0.11688(15) 0.34468(10) 0.0380(3) Uani 1 1 d . . . . .
H00L H 0.524187 0.046541 0.330181 0.046 Uiso 1 1 calc R U . . .
C00J C 0.34178(19) 0.5806(2) 0.89193(11) 0.0529(4) Uani 1 1 d . . . . .
H00M H 0.351512 0.651877 0.934588 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C004 1.2382(15) . ?
N002 H002 0.8600 . ?
N002 C007 1.3846(16) . ?
N002 C008 1.3735(16) . ?
N003 C004 1.3438(16) . ?
N003 C00A 1.4623(17) . ?
N003 C00B 1.4727(16) . ?
C004 C005 1.5007(18) . ?
C005 C007 1.4713(17) . ?
C005 C00G 1.3293(17) . ?
C006 C008 1.4142(17) . ?
C006 C009 1.4343(18) . ?
C006 C00D 1.4080(18) . ?
C007 C009 1.3805(17) . ?
C008 C00C 1.3958(19) . ?
C009 C00E 1.4962(18) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00F 1.4703(19) . ?
C00B H00C 0.9700 . ?
C00B H00D 0.9700 . ?
C00B C00E 1.5181(18) . ?
C00C H00E 0.9300 . ?
C00C C00H 1.3781(19) . ?
C00D H00F 0.9300 . ?
C00D C00I 1.381(2) . ?
C00E H00G 0.9700 . ?
C00E H00H 0.9700 . ?
C00F C00J 1.177(2) . ?
C00G H00I 0.9300 . ?
C00G H00J 0.9300 . ?
C00H H00K 0.9300 . ?
C00H C00I 1.405(2) . ?
C00I H00L 0.9300 . ?
C00J H00M 0.9300 . ?

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
C007 N002 H002 125.6 . . ?
C008 N002 H002 125.6 . . ?
C008 N002 C007 108.80(10) . . ?
C004 N003 C00A 118.57(11) . . ?
C004 N003 C00B 122.54(11) . . ?
C00A N003 C00B 118.61(10) . . ?
O001 C004 N003 121.35(12) . . ?
O001 C004 C005 120.97(11) . . ?
N003 C004 C005 117.66(11) . . ?
C007 C005 C004 118.05(10) . . ?
C00G C005 C004 119.08(12) . . ?
C00G C005 C007 122.48(12) . . ?
C008 C006 C009 107.09(11) . . ?
C00D C006 C008 118.81(12) . . ?
C00D C006 C009 134.07(12) . . ?
N002 C007 C005 119.19(10) . . ?
C009 C007 N002 109.63(11) . . ?
C009 C007 C005 131.18(12) . . ?
N002 C008 C006 107.94(11) . . ?
N002 C008 C00C 129.71(12) . . ?
C00C C008 C006 122.31(12) . . ?
C006 C009 C00E 126.53(11) . . ?
C007 C009 C006 106.51(11) . . ?
C007 C009 C00E 126.79(12) . . ?
N003 C00A H00A 109.0 . . ?
N003 C00A H00B 109.0 . . ?
N003 C00A C00F 112.98(11) . . ?
H00A C00A H00B 107.8 . . ?
C00F C00A H00A 109.0 . . ?
C00F C00A H00B 109.0 . . ?
N003 C00B H00C 109.1 . . ?
N003 C00B H00D 109.1 . . ?
N003 C00B C00E 112.60(10) . . ?
H00C C00B H00D 107.8 . . ?
C00E C00B H00C 109.1 . . ?
C00E C00B H00D 109.1 . . ?
C008 C00C H00E 121.2 . . ?
C00H C00C C008 117.51(13) . . ?
C00H C00C H00E 121.2 . . ?
C006 C00D H00F 120.6 . . ?
C00I C00D C006 118.76(13) . . ?
C00I C00D H00F 120.6 . . ?
C009 C00E C00B 112.03(10) . . ?
C009 C00E H00G 109.2 . . ?
C009 C00E H00H 109.2 . . ?
C00B C00E H00G 109.2 . . ?
C00B C00E H00H 109.2 . . ?
H00G C00E H00H 107.9 . . ?
C00J C00F C00A 178.35(17) . . ?
C005 C00G H00I 120.0 . . ?
C005 C00G H00J 120.0 . . ?
H00I C00G H00J 120.0 . . ?
C00C C00H H00K 119.3 . . ?
C00C C00H C00I 121.34(14) . . ?
C00I C00H H00K 119.3 . . ?
C00D C00I C00H 121.27(13) . . ?
C00D C00I H00L 119.4 . . ?
C00H C00I H00L 119.4 . . ?
C00F C00J H00M 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C004 C005 C007 -130.83(12) . . . . ?
O001 C004 C005 C00G 42.12(17) . . . . ?
N002 C007 C009 C006 -1.13(14) . . . . ?
N002 C007 C009 C00E 174.51(11) . . . . ?
N002 C008 C00C C00H 177.30(13) . . . . ?
N003 C004 C005 C007 47.42(15) . . . . ?
N003 C004 C005 C00G -139.62(12) . . . . ?
N003 C00B C00E C009 65.41(14) . . . . ?
C004 N003 C00A C00F -86.52(14) . . . . ?
C004 N003 C00B C00E -83.66(14) . . . . ?
C004 C005 C007 N002 142.72(11) . . . . ?
C004 C005 C007 C009 -36.45(18) . . . . ?
C005 C007 C009 C006 178.11(12) . . . . ?
C005 C007 C009 C00E -6.3(2) . . . . ?
C006 C008 C00C C00H -0.35(19) . . . . ?
C006 C009 C00E C00B 167.19(11) . . . . ?
C006 C00D C00I C00H 0.2(2) . . . . ?
C007 N002 C008 C006 -1.54(13) . . . . ?
C007 N002 C008 C00C -179.46(12) . . . . ?
C007 C009 C00E C00B -7.59(18) . . . . ?
C008 N002 C007 C005 -177.65(10) . . . . ?
C008 N002 C007 C009 1.69(13) . . . . ?
C008 C006 C009 C007 0.17(13) . . . . ?
C008 C006 C009 C00E -175.47(11) . . . . ?
C008 C006 C00D C00I -0.48(18) . . . . ?
C008 C00C C00H C00I 0.1(2) . . . . ?
C009 C006 C008 N002 0.84(13) . . . . ?
C009 C006 C008 C00C 178.94(11) . . . . ?
C009 C006 C00D C00I -178.32(13) . . . . ?
C00A N003 C004 O001 5.27(18) . . . . ?
C00A N003 C004 C005 -172.98(10) . . . . ?
C00A N003 C00B C00E 102.52(13) . . . . ?
C00B N003 C004 O001 -168.55(11) . . . . ?
C00B N003 C004 C005 13.20(17) . . . . ?
C00B N003 C00A C00F 87.54(14) . . . . ?
C00C C00H C00I C00D 0.0(2) . . . . ?
C00D C006 C008 N002 -177.53(11) . . . . ?
C00D C006 C008 C00C 0.57(18) . . . . ?
C00D C006 C009 C007 178.18(13) . . . . ?
C00D C006 C009 C00E 2.5(2) . . . . ?
C00G C005 C007 N002 -29.98(17) . . . . ?
C00G C005 C007 C009 150.84(14) . . . . ?

_olex2_exptl_crystal_mounting_method 'manual mounting'
_olex2_submission_original_sample_id 250619WayamaKaneko
_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.718

####################################################################### 
# 
# 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_exp_11
_database_code_depnum_ccdc_archive 'CCDC 2179523'
loop_
_audit_author_name
_audit_author_address
'Toshiaki Wayama'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   15.1685(9)
_cell_length_b                   9.9416(3)
_cell_length_c                   12.7215(6)
_cell_angle_alpha                90
_cell_angle_beta                 118.988(6)
_cell_angle_gamma                90
_cell_volume                     1678.06(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5784
_cell_measurement_temperature    170
_cell_measurement_theta_max      32.0930
_cell_measurement_theta_min      2.6700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
18 -2 -9 0.2028
-7 -6 18 0.1630
13 -9 -11 0.1483
18 1 -5 0.2435
2 12 9 0.1574
-14 8 11 0.1036
0 -12 -10 0.1126
8 6 -18 0.1611
3 -8 14 0.2041
18 -3 -9 0.2057
-8 -6 18 0.1641
-18 2 9 0.1633
1 8 -16 0.1273
13 -9 -10 0.1483
3 12 7 0.1666
-13 9 10 0.1096
-1 -13 -8 0.1019
12 -5 -17 0.1549
1 -5 -18 0.1529
-12 5 17 0.1157
4 14 -3 0.1860
-12 10 5 0.1376
1 -14 4 0.1281
-18 -2 10 0.1775
5 13 -7 0.1869

_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.262
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.560
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00    7.61    --   30.00  54.00  30.00  193
  2  ω    -74.00 119.00   1.00    7.61    --   30.00  54.00 -30.00  193
  3  ω    -74.00 -35.00   1.00    7.61    --   30.00  54.00-120.00   39
  4  ω    -74.00 119.00   1.00    7.61    --   30.00  54.00-180.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3550
_reflns_number_total             3828
_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 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1656 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.2137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0755
_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 Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00I(H00C,H00D), C00K(H00F,H00H), C00O(H00N,H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00J(H00J), C00L(H00L), C00M(H00M)
2.c :
 C00G(H00G)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.33011(10) 0.49270(14) 0.42629(12) 0.0275(3) Uani 1 1 d . . . . .
O002 O 0.58681(12) 0.19525(14) 0.45091(13) 0.0348(3) Uani 1 1 d . . . . .
O003 O 0.26245(10) 0.51842(15) 0.22680(12) 0.0326(3) Uani 1 1 d . . . . .
N004 N 0.57063(11) 0.40244(16) 0.52366(13) 0.0220(3) Uani 1 1 d . . . . .
N005 N 0.42920(12) 0.75081(15) 0.30835(14) 0.0255(3) Uani 1 1 d . . . . .
C006 C 0.54819(14) 0.30536(18) 0.43605(16) 0.0247(4) Uani 1 1 d . . . . .
C007 C 0.33449(14) 0.50967(17) 0.32507(16) 0.0215(4) Uani 1 1 d . . . . .
C008 C 0.63409(13) 0.55965(18) 0.66929(17) 0.0227(4) Uani 1 1 d . . . . .
C009 C 0.45167(15) 0.88401(19) 0.15982(16) 0.0268(4) Uani 1 1 d . . . . .
C00A C 0.46726(14) 0.36604(18) 0.32174(16) 0.0238(4) Uani 1 1 d . . . . .
C00B C 0.44344(14) 0.50865(18) 0.34721(15) 0.0206(4) Uani 1 1 d . . . . .
C00C C 0.52046(13) 0.52420(18) 0.47688(16) 0.0205(3) Uani 1 1 d . . . . .
C00D C 0.55780(13) 0.62282(18) 0.55945(16) 0.0216(3) Uani 1 1 d . . . . .
C00E C 0.69486(15) 0.6068(2) 0.78625(17) 0.0291(4) Uani 1 1 d . . . . .
H00E H 0.690929 0.695756 0.806119 0.035 Uiso 1 1 calc R U . . .
C00F C 0.51487(16) 0.81400(19) 0.41297(17) 0.0290(4) Uani 1 1 d . . . . .
H00A H 0.505642 0.910788 0.406923 0.035 Uiso 1 1 calc R U . . .
H00B H 0.576237 0.794194 0.409984 0.035 Uiso 1 1 calc R U . . .
C00G C 0.51107(16) 0.9094(2) 0.12778(18) 0.0320(4) Uani 1 1 d . . . . .
H00G H 0.557803 0.929288 0.102570 0.038 Uiso 1 1 calc R U . . .
C00H C 0.64229(13) 0.42302(19) 0.64389(15) 0.0228(4) Uani 1 1 d . . . . .
C00I C 0.38296(15) 0.8447(2) 0.20641(18) 0.0293(4) Uani 1 1 d . . . . .
H00C H 0.361718 0.924912 0.231444 0.035 Uiso 1 1 calc R U . . .
H00D H 0.323329 0.803106 0.142106 0.035 Uiso 1 1 calc R U . . .
C00J C 0.70994(15) 0.3344(2) 0.72823(18) 0.0300(4) Uani 1 1 d . . . . .
H00J H 0.715297 0.245725 0.708645 0.036 Uiso 1 1 calc R U . . .
C00K C 0.45317(14) 0.62158(18) 0.27133(16) 0.0237(4) Uani 1 1 d . . . . .
H00F H 0.521265 0.623811 0.282991 0.028 Uiso 1 1 calc R U . . .
H00H H 0.407150 0.605599 0.186819 0.028 Uiso 1 1 calc R U . . .
C00L C 0.76115(17) 0.5176(2) 0.87196(19) 0.0351(5) Uani 1 1 d . . . . .
H00L H 0.801108 0.547482 0.950386 0.042 Uiso 1 1 calc R U . . .
C00M C 0.76953(17) 0.3842(2) 0.84367(19) 0.0354(5) Uani 1 1 d . . . . .
H00M H 0.815758 0.327657 0.903073 0.042 Uiso 1 1 calc R U . . .
C00N C 0.42418(18) 0.2989(2) 0.21929(19) 0.0344(5) Uani 1 1 d . . . . .
C00O C 0.52806(16) 0.76796(19) 0.53431(16) 0.0283(4) Uani 1 1 d . . . . .
H00N H 0.579297 0.822844 0.597366 0.034 Uiso 1 1 calc R U . . .
H00O H 0.465306 0.781612 0.535682 0.034 Uiso 1 1 calc R U . . .
C00P C 0.22975(16) 0.4848(3) 0.4128(2) 0.0352(5) Uani 1 1 d . . . . .
H00I H 0.446(2) 0.206(3) 0.217(2) 0.043(7) Uiso 1 1 d . . . . .
H00K H 0.372(2) 0.337(3) 0.149(2) 0.039(7) Uiso 1 1 d . . . . .
H00P H 0.194(2) 0.572(3) 0.379(3) 0.052(8) Uiso 1 1 d . . . . .
H00Q H 0.243(3) 0.475(3) 0.498(3) 0.068(10) Uiso 1 1 d . . . . .
H00R H 0.189(2) 0.410(3) 0.357(3) 0.043(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C007 1.332(2) . ?
O001 C00P 1.449(2) . ?
O002 C006 1.212(2) . ?
O003 C007 1.200(2) . ?
N004 C006 1.386(2) . ?
N004 C00C 1.400(2) . ?
N004 C00H 1.397(2) . ?
N005 C00F 1.476(3) . ?
N005 C00I 1.471(2) . ?
N005 C00K 1.473(2) . ?
C006 C00A 1.502(3) . ?
C007 C00B 1.536(2) . ?
C008 C00D 1.456(2) . ?
C008 C00E 1.398(3) . ?
C008 C00H 1.416(3) . ?
C009 C00G 1.182(3) . ?
C009 C00I 1.480(3) . ?
C00A C00B 1.536(2) . ?
C00A C00N 1.321(3) . ?
C00B C00C 1.497(2) . ?
C00B C00K 1.534(2) . ?
C00C C00D 1.345(3) . ?
C00D C00O 1.499(3) . ?
C00E H00E 0.9300 . ?
C00E C00L 1.387(3) . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00F C00O 1.527(3) . ?
C00G H00G 0.9300 . ?
C00H C00J 1.383(3) . ?
C00I H00C 0.9700 . ?
C00I H00D 0.9700 . ?
C00J H00J 0.9300 . ?
C00J C00M 1.390(3) . ?
C00K H00F 0.9700 . ?
C00K H00H 0.9700 . ?
C00L H00L 0.9300 . ?
C00L C00M 1.396(3) . ?
C00M H00M 0.9300 . ?
C00N H00I 0.99(3) . ?
C00N H00K 0.94(3) . ?
C00O H00N 0.9700 . ?
C00O H00O 0.9700 . ?
C00P H00P 1.01(3) . ?
C00P H00Q 1.00(4) . ?
C00P H00R 1.01(3) . ?

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
C007 O001 C00P 115.72(15) . . ?
C006 N004 C00C 112.91(15) . . ?
C006 N004 C00H 137.71(16) . . ?
C00H N004 C00C 108.24(15) . . ?
C00I N005 C00F 111.12(15) . . ?
C00I N005 C00K 110.95(14) . . ?
C00K N005 C00F 114.43(15) . . ?
O002 C006 N004 126.26(17) . . ?
O002 C006 C00A 128.32(17) . . ?
N004 C006 C00A 105.42(15) . . ?
O001 C007 C00B 112.04(15) . . ?
O003 C007 O001 124.71(17) . . ?
O003 C007 C00B 123.16(16) . . ?
C00E C008 C00D 133.21(18) . . ?
C00E C008 C00H 118.62(17) . . ?
C00H C008 C00D 108.17(16) . . ?
C00G C009 C00I 175.6(2) . . ?
C006 C00A C00B 109.39(15) . . ?
C00N C00A C006 122.24(18) . . ?
C00N C00A C00B 128.32(18) . . ?
C00A C00B C007 108.04(14) . . ?
C00C C00B C007 113.39(14) . . ?
C00C C00B C00A 100.95(14) . . ?
C00C C00B C00K 110.86(15) . . ?
C00K C00B C007 107.63(14) . . ?
C00K C00B C00A 116.02(15) . . ?
N004 C00C C00B 110.62(14) . . ?
C00D C00C N004 111.22(16) . . ?
C00D C00C C00B 138.09(17) . . ?
C008 C00D C00O 129.57(16) . . ?
C00C C00D C008 105.85(16) . . ?
C00C C00D C00O 124.45(17) . . ?
C008 C00E H00E 120.8 . . ?
C00L C00E C008 118.40(19) . . ?
C00L C00E H00E 120.8 . . ?
N005 C00F H00A 108.7 . . ?
N005 C00F H00B 108.7 . . ?
N005 C00F C00O 114.24(16) . . ?
H00A C00F H00B 107.6 . . ?
C00O C00F H00A 108.7 . . ?
C00O C00F H00B 108.7 . . ?
C009 C00G H00G 180.0 . . ?
N004 C00H C008 106.42(15) . . ?
C00J C00H N004 130.32(18) . . ?
C00J C00H C008 123.26(17) . . ?
N005 C00I C009 113.16(16) . . ?
N005 C00I H00C 108.9 . . ?
N005 C00I H00D 108.9 . . ?
C009 C00I H00C 108.9 . . ?
C009 C00I H00D 108.9 . . ?
H00C C00I H00D 107.8 . . ?
C00H C00J H00J 121.6 . . ?
C00H C00J C00M 116.78(19) . . ?
C00M C00J H00J 121.6 . . ?
N005 C00K C00B 108.86(14) . . ?
N005 C00K H00F 109.9 . . ?
N005 C00K H00H 109.9 . . ?
C00B C00K H00F 109.9 . . ?
C00B C00K H00H 109.9 . . ?
H00F C00K H00H 108.3 . . ?
C00E C00L H00L 119.1 . . ?
C00E C00L C00M 121.8(2) . . ?
C00M C00L H00L 119.1 . . ?
C00J C00M C00L 121.13(19) . . ?
C00J C00M H00M 119.4 . . ?
C00L C00M H00M 119.4 . . ?
C00A C00N H00I 119.6(15) . . ?
C00A C00N H00K 121.0(16) . . ?
H00I C00N H00K 119(2) . . ?
C00D C00O C00F 112.49(16) . . ?
C00D C00O H00N 109.1 . . ?
C00D C00O H00O 109.1 . . ?
C00F C00O H00N 109.1 . . ?
C00F C00O H00O 109.1 . . ?
H00N C00O H00O 107.8 . . ?
O001 C00P H00P 108.8(17) . . ?
O001 C00P H00Q 103(2) . . ?
O001 C00P H00R 112.0(16) . . ?
H00P C00P H00Q 109(2) . . ?
H00P C00P H00R 109(2) . . ?
H00Q C00P H00R 115(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C007 C00B C00A 96.38(17) . . . . ?
O001 C007 C00B C00C -14.6(2) . . . . ?
O001 C007 C00B C00K -137.63(15) . . . . ?
O002 C006 C00A C00B -179.43(19) . . . . ?
O002 C006 C00A C00N 2.8(3) . . . . ?
O003 C007 C00B C00A -80.3(2) . . . . ?
O003 C007 C00B C00C 168.65(17) . . . . ?
O003 C007 C00B C00K 45.7(2) . . . . ?
N004 C006 C00A C00B 0.65(19) . . . . ?
N004 C006 C00A C00N -177.14(18) . . . . ?
N004 C00C C00D C008 -3.0(2) . . . . ?
N004 C00C C00D C00O 173.32(17) . . . . ?
N004 C00H C00J C00M -177.29(19) . . . . ?
N005 C00F C00O C00D 66.8(2) . . . . ?
C006 N004 C00C C00B 9.1(2) . . . . ?
C006 N004 C00C C00D -168.33(16) . . . . ?
C006 N004 C00H C008 166.7(2) . . . . ?
C006 N004 C00H C00J -14.0(4) . . . . ?
C006 C00A C00B C007 -115.02(16) . . . . ?
C006 C00A C00B C00C 4.21(17) . . . . ?
C006 C00A C00B C00K 124.08(17) . . . . ?
C007 C00B C00C N004 107.54(17) . . . . ?
C007 C00B C00C C00D -76.0(3) . . . . ?
C007 C00B C00K N005 59.68(19) . . . . ?
C008 C00D C00O C00F 135.69(19) . . . . ?
C008 C00E C00L C00M 1.1(3) . . . . ?
C008 C00H C00J C00M 2.0(3) . . . . ?
C00A C00B C00C N004 -7.76(18) . . . . ?
C00A C00B C00C C00D 168.7(2) . . . . ?
C00A C00B C00K N005 -179.21(15) . . . . ?
C00B C00C C00D C008 -179.4(2) . . . . ?
C00B C00C C00D C00O -3.1(3) . . . . ?
C00C N004 C006 O002 174.17(19) . . . . ?
C00C N004 C006 C00A -5.90(19) . . . . ?
C00C N004 C00H C008 0.37(19) . . . . ?
C00C N004 C00H C00J 179.74(19) . . . . ?
C00C C00B C00K N005 -64.86(18) . . . . ?
C00C C00D C00O C00F -39.7(3) . . . . ?
C00D C008 C00E C00L 179.8(2) . . . . ?
C00D C008 C00H N004 -2.13(19) . . . . ?
C00D C008 C00H C00J 178.44(17) . . . . ?
C00E C008 C00D C00C -176.1(2) . . . . ?
C00E C008 C00D C00O 7.8(3) . . . . ?
C00E C008 C00H N004 177.27(16) . . . . ?
C00E C008 C00H C00J -2.2(3) . . . . ?
C00E C00L C00M C00J -1.3(4) . . . . ?
C00F N005 C00I C009 64.0(2) . . . . ?
C00F N005 C00K C00B 84.78(18) . . . . ?
C00H N004 C006 O002 8.3(4) . . . . ?
C00H N004 C006 C00A -171.8(2) . . . . ?
C00H N004 C00C C00B 179.19(15) . . . . ?
C00H N004 C00C C00D 1.7(2) . . . . ?
C00H C008 C00D C00C 3.1(2) . . . . ?
C00H C008 C00D C00O -172.88(18) . . . . ?
C00H C008 C00E C00L 0.5(3) . . . . ?
C00H C00J C00M C00L -0.3(3) . . . . ?
C00I N005 C00F C00O 146.13(16) . . . . ?
C00I N005 C00K C00B -148.52(15) . . . . ?
C00K N005 C00F C00O -87.3(2) . . . . ?
C00K N005 C00I C009 -64.5(2) . . . . ?
C00K C00B C00C N004 -131.26(16) . . . . ?
C00K C00B C00C C00D 45.2(3) . . . . ?
C00N C00A C00B C007 62.6(2) . . . . ?
C00N C00A C00B C00C -178.2(2) . . . . ?
C00N C00A C00B C00K -58.3(3) . . . . ?
C00P O001 C007 O003 0.0(3) . . . . ?
C00P O001 C007 C00B -176.67(17) . . . . ?

_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
;
####################################################################### 
# 
# 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_181127_hk_diels-alder
_database_code_depnum_ccdc_archive 'CCDC 2179775'
loop_
_audit_author_name
_audit_author_address
'Toshiaki Wayama'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2022-06-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C21 H22 N2 O4'
_chemical_formula_sum            'C21 H22 N2 O4'
_chemical_formula_weight         366.420
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           ' P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,-y+1/2,z

_symmetry_Int_Tables_number      33
_cell_length_a                   10.3562(3)
_cell_length_b                   12.9953(4)
_cell_length_c                   14.1689(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1906.88(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    173
_cell_measurement_theta_max      31.5080
_cell_measurement_theta_min      3.6670
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             776.402
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 12 -15 0.1404
-2 10 17 0.1547
-14 2 -7 0.2333
-11 -11 -6 0.2216
-1 -14 13 0.1479
11 7 11 0.2215
8 15 -4 0.2265
-8 10 13 0.1587
-2 10 17 0.1529
10 3 13 0.2446
13 -1 8 0.2411
5 -10 -15 0.1199

_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.279
_diffrn_ambient_temperature      173
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12481
_diffrn_reflns_point_group_measured_fraction_full 0.8514
_diffrn_reflns_point_group_measured_fraction_max 0.8508
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.88
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   0.50    4.79    --   30.00  54.00 -60.00  386
  2  ω    -74.00 119.00   0.50    4.79    --   30.00  54.00 -60.00  386
  3  ω     25.00  52.00   0.50    4.79    --   30.00  54.00-150.00   54
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.689
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              17
_reflns_limit_l_min              -14
_reflns_number_gt                2740
_reflns_number_total             2965
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.1133
_refine_diff_density_min         -0.1693
_refine_diff_density_rms         0.0357
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.7(8)
_refine_ls_d_res_high            0.8306
_refine_ls_d_res_low             7.0845
_refine_ls_goodness_of_fit_ref   1.0495
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.0495
_refine_ls_shift/su_max          0.0112
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.1936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0830
_olex2_refinement_description    
;
;
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_refinement_flags_posn
O001 O -0.59047(11) -0.53733(10) -0.37388(10) 0.0358(3) Uani 1.000000 .
O002 O -0.64070(11) -0.34795(9) -0.54693(9) 0.0342(3) Uani 1.000000 .
O003 O -0.55969(12) -0.41876(11) -0.67899(10) 0.0401(3) Uani 1.000000 .
O004 O -0.44378(12) -0.65236(10) -0.42201(11) 0.0414(4) Uani 1.000000 .
N005 N -0.14408(13) -0.44348(10) -0.36764(10) 0.0258(3) Uani 1.000000 .
N006 N -0.32821(13) -0.51978(11) -0.66200(10) 0.0283(3) Uani 1.000000 .
H006 H -0.37476(13) -0.50413(11) -0.71018(10) 0.0340(4) Uiso 1.000000 R
C007 C -0.23567(15) -0.59853(13) -0.66040(12) 0.0269(4) Uani 1.000000 .
C008 C -0.33427(15) -0.47154(12) -0.57697(11) 0.0234(3) Uani 1.000000 .
C009 C -0.21542(14) -0.50077(12) -0.52096(12) 0.0222(3) Uani 1.000000 .
C00A C -0.16950(15) -0.59470(12) -0.57506(12) 0.0244(3) Uani 1.000000 .
C00B C -0.54514(16) -0.39373(13) -0.59659(13) 0.0278(4) Uani 1.000000 .
C00C C -0.46997(16) -0.56706(13) -0.39635(12) 0.0260(4) Uani 1.000000 .
C00D C -0.37507(14) -0.48005(11) -0.38268(12) 0.0227(3) Uani 1.000000 .
H00D H -0.37295(14) -0.46255(11) -0.31542(12) 0.0273(4) Uiso 1.000000 R
C00E C -0.41911(16) -0.38397(12) -0.43803(12) 0.0259(4) Uani 1.000000 .
H00a H -0.50205(16) -0.36062(12) -0.41452(12) 0.0311(4) Uiso 1.000000 R
H00b H -0.35703(16) -0.32882(12) -0.42971(12) 0.0311(4) Uiso 1.000000 R
C00F C -0.42995(15) -0.41121(12) -0.54132(12) 0.0239(3) Uani 1.000000 .
C00G C -0.23892(14) -0.51280(12) -0.41263(12) 0.0212(3) Uani 1.000000 .
H00G H -0.22276(14) -0.58406(12) -0.39333(12) 0.0255(4) Uiso 1.000000 R
C00H C -0.04057(16) -0.57908(15) -0.27134(13) 0.0310(4) Uani 1.000000 .
C00I C -0.10395(17) -0.47663(14) -0.27346(13) 0.0310(4) Uani 1.000000 .
H00c H -0.04472(17) -0.42600(14) -0.24785(13) 0.0372(5) Uiso 1.000000 R
H00e H -0.17925(17) -0.47849(14) -0.23277(13) 0.0372(5) Uiso 1.000000 R
C00J C -0.03909(16) -0.42699(14) -0.43411(13) 0.0295(4) Uani 1.000000 .
H00f H 0.01013(16) -0.36583(14) -0.41842(13) 0.0354(5) Uiso 1.000000 R
H00h H 0.01852(16) -0.48580(14) -0.43636(13) 0.0354(5) Uiso 1.000000 R
C00K C -0.07592(17) -0.66781(14) -0.55490(14) 0.0327(4) Uani 1.000000 .
H00K H -0.03119(17) -0.66630(14) -0.49800(14) 0.0392(5) Uiso 1.000000 R
C00L C -0.11138(16) -0.41386(13) -0.52601(13) 0.0280(4) Uani 1.000000 .
H00i H -0.05462(16) -0.42335(13) -0.57977(13) 0.0336(5) Uiso 1.000000 R
H00j H -0.15124(16) -0.34645(13) -0.52992(13) 0.0336(5) Uiso 1.000000 R
C00M C -0.21165(18) -0.67319(16) -0.72783(13) 0.0372(4) Uani 1.000000 .
H00M H -0.25644(18) -0.67473(16) -0.78471(13) 0.0446(5) Uiso 1.000000 R
C00N C -0.1171(2) -0.74602(16) -0.70646(15) 0.0437(5) Uani 1.000000 .
H00N H -0.0985(2) -0.79735(16) -0.75014(15) 0.0524(6) Uiso 1.000000 R
C10 C 0.00694(19) -0.66159(17) -0.27233(15) 0.0400(4) Uani 1.000000 .
H10 H 0.04439(19) -0.72663(17) -0.27310(15) 0.0480(5) Uiso 1.000000 R
C00P C -0.0505(2) -0.74383(15) -0.62217(15) 0.0415(5) Uani 1.000000 .
H00P H 0.0121(2) -0.79345(15) -0.60998(15) 0.0498(6) Uiso 1.000000 R
C00Q C -0.76228(17) -0.33778(18) -0.59634(17) 0.0469(5) Uani 1.000000 .
H00l H -0.8211(6) -0.2979(11) -0.5588(5) 0.0703(8) Uiso 1.000000 GR
H00o H -0.7482(3) -0.3039(11) -0.6556(5) 0.0703(8) Uiso 1.000000 GR
H00q H -0.7982(8) -0.4048(2) -0.6073(10) 0.0703(8) Uiso 1.000000 GR
C00R C -0.69026(19) -0.61448(18) -0.38581(19) 0.0546(6) Uani 1.000000 .
H00r H -0.6722(9) -0.6723(6) -0.3457(9) 0.0819(9) Uiso 1.000000 GR
H00s H -0.7725(3) -0.5856(5) -0.3692(12) 0.0819(9) Uiso 1.000000 GR
H00t H -0.6921(11) -0.6367(10) -0.4504(3) 0.0819(9) Uiso 1.000000 GR


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
O001 C00C 1.345(2) . ?
O001 C00R 1.450(2) . ?
O002 C00B 1.352(2) . ?
O002 C00Q 1.447(2) . ?
O003 C00B 1.221(2) . ?
O004 C00C 1.198(2) . ?
N005 C00G 1.477(2) . ?
N005 C00I 1.463(2) . ?
N005 C00J 1.454(2) . ?
N006 H006 0.8600 . ?
N006 C007 1.402(2) . ?
N006 C008 1.360(2) . ?
C007 C00A 1.391(2) . ?
C007 C00M 1.384(3) . ?
C008 C009 1.513(2) . ?
C008 C00F 1.361(2) . ?
C009 C00A 1.518(2) . ?
C009 C00G 1.562(2) . ?
C009 C00L 1.563(2) . ?
C00A C00K 1.387(2) . ?
C00B C00F 1.445(2) . ?
C00C C00D 1.511(2) . ?
C00D H00D 0.9800 . ?
C00D C00E 1.543(2) . ?
C00D C00G 1.533(2) . ?
C00E H00a 0.9700 . ?
C00E H00b 0.9700 . ?
C00E C00F 1.510(2) . ?
C00G H00G 0.9800 . ?
C00H C00I 1.485(3) . ?
C00H C10 1.180(3) . ?
C00I H00c 0.9700 . ?
C00I H00e 0.9700 . ?
C00J H00f 0.9700 . ?
C00J H00h 0.9700 . ?
C00J C00L 1.512(3) . ?
C00K H00K 0.9300 . ?
C00K C00P 1.398(3) . ?
C00L H00i 0.9700 . ?
C00L H00j 0.9700 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.395(3) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.380(3) . ?
C10 H10 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00l 0.9600 . ?
C00Q H00o 0.9600 . ?
C00Q H00q 0.9600 . ?
C00R H00r 0.9600 . ?
C00R H00s 0.9600 . ?
C00R H00t 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
C00R O001 C00C 115.81(14) . . ?
C00Q O002 C00B 115.17(14) . . ?
C00I N005 C00G 113.77(13) . . ?
C00J N005 C00G 107.90(13) . . ?
C00J N005 C00I 114.95(13) . . ?
C007 N006 H006 124.64(9) . . ?
C008 N006 H006 124.64(9) . . ?
C008 N006 C007 110.71(14) . . ?
C00A C007 N006 108.95(14) . . ?
C00M C007 N006 128.55(17) . . ?
C00M C007 C00A 122.46(16) . . ?
C009 C008 N006 108.16(13) . . ?
C00F C008 N006 128.92(15) . . ?
C00F C008 C009 122.84(14) . . ?
C00A C009 C008 101.06(13) . . ?
C00G C009 C008 114.45(12) . . ?
C00G C009 C00A 117.69(13) . . ?
C00L C009 C008 110.82(13) . . ?
C00L C009 C00A 110.00(13) . . ?
C00L C009 C00G 102.99(13) . . ?
C009 C00A C007 108.27(14) . . ?
C00K C00A C007 119.93(16) . . ?
C00K C00A C009 131.75(16) . . ?
O003 C00B O002 121.62(15) . . ?
C00F C00B O002 113.04(15) . . ?
C00F C00B O003 125.32(16) . . ?
O004 C00C O001 123.23(15) . . ?
C00D C00C O001 111.01(13) . . ?
C00D C00C O004 125.76(15) . . ?
H00D C00D C00C 108.24(9) . . ?
C00E C00D C00C 110.37(13) . . ?
C00E C00D H00D 108.24(9) . . ?
C00G C00D C00C 110.81(12) . . ?
C00G C00D H00D 108.24(8) . . ?
C00G C00D C00E 110.84(13) . . ?
H00a C00E C00D 109.89(8) . . ?
H00b C00E C00D 109.89(8) . . ?
H00b C00E H00a 108.3 . . ?
C00F C00E C00D 108.96(13) . . ?
C00F C00E H00a 109.89(9) . . ?
C00F C00E H00b 109.89(9) . . ?
C00B C00F C008 119.38(15) . . ?
C00E C00F C008 116.15(14) . . ?
C00E C00F C00B 123.36(14) . . ?
C009 C00G N005 105.04(12) . . ?
C00D C00G N005 108.83(12) . . ?
C00D C00G C009 112.81(13) . . ?
H00G C00G N005 110.01(8) . . ?
H00G C00G C009 110.01(8) . . ?
H00G C00G C00D 110.01(8) . . ?
C10 C00H C00I 177.6(2) . . ?
C00H C00I N005 114.09(15) . . ?
H00c C00I N005 108.73(9) . . ?
H00c C00I C00H 108.73(10) . . ?
H00e C00I N005 108.73(9) . . ?
H00e C00I C00H 108.73(10) . . ?
H00e C00I H00c 107.6 . . ?
H00f C00J N005 111.41(9) . . ?
H00h C00J N005 111.41(9) . . ?
H00h C00J H00f 109.3 . . ?
C00L C00J N005 101.78(13) . . ?
C00L C00J H00f 111.41(9) . . ?
C00L C00J H00h 111.41(10) . . ?
H00K C00K C00A 120.80(11) . . ?
C00P C00K C00A 118.39(18) . . ?
C00P C00K H00K 120.80(12) . . ?
C00J C00L C009 102.73(13) . . ?
H00i C00L C009 111.22(9) . . ?
H00i C00L C00J 111.22(10) . . ?
H00j C00L C009 111.22(8) . . ?
H00j C00L C00J 111.22(10) . . ?
H00j C00L H00i 109.1 . . ?
H00M C00M C007 121.57(11) . . ?
C00N C00M C007 116.86(18) . . ?
C00N C00M H00M 121.57(11) . . ?
H00N C00N C00M 119.16(11) . . ?
C00P C00N C00M 121.67(18) . . ?
C00P C00N H00N 119.16(11) . . ?
H10 C10 C00H 180.0 . . ?
C00N C00P C00K 120.69(18) . . ?
H00P C00P C00K 119.65(12) . . ?
H00P C00P C00N 119.65(11) . . ?
H00l C00Q O002 109.5 . . ?
H00o C00Q O002 109.5 . . ?
H00o C00Q H00l 109.5 . . ?
H00q C00Q O002 109.5 . . ?
H00q C00Q H00l 109.5 . . ?
H00q C00Q H00o 109.5 . . ?
H00r C00R O001 109.5 . . ?
H00s C00R O001 109.5 . . ?
H00s C00R H00r 109.5 . . ?
H00t C00R O001 109.5 . . ?
H00t C00R H00r 109.5 . . ?
H00t C00R H00s 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C00C C00D C00E -54.27(16) . . . . ?
O001 C00C C00D C00G -177.43(14) . . . . ?
O002 C00B C00F C008 169.16(13) . . . . ?
O002 C00B C00F C00E 1.72(18) . . . . ?
O003 C00B C00F C008 -9.1(2) . . . . ?
O003 C00B C00F C00E -176.58(16) . . . . ?
O004 C00C C00D C00E 127.02(19) . . . . ?
O004 C00C C00D C00G 3.9(2) . . . . ?
N005 C00G C009 C008 -125.20(12) . . . . ?
N005 C00G C009 C00A 116.34(12) . . . . ?
N005 C00G C009 C00L -4.83(12) . . . . ?
N005 C00G C00D C00C -159.67(13) . . . . ?
N005 C00G C00D C00E 77.44(14) . . . . ?
N005 C00J C00L C009 -43.15(13) . . . . ?
N006 C007 C00A C009 -5.01(15) . . . . ?
N006 C007 C00A C00K 177.42(13) . . . . ?
N006 C007 C00M C00N -177.04(19) . . . . ?
N006 C008 C009 C00A -16.84(13) . . . . ?
N006 C008 C009 C00G -144.35(12) . . . . ?
N006 C008 C009 C00L 99.72(14) . . . . ?
N006 C008 C00F C00B 1.2(2) . . . . ?
N006 C008 C00F C00E 169.51(17) . . . . ?
C007 C00A C009 C008 12.98(14) . . . . ?
C007 C00A C009 C00G 138.35(12) . . . . ?
C007 C00A C009 C00L -104.18(14) . . . . ?
C007 C00A C00K C00P 0.26(19) . . . . ?
C007 C00M C00N C00P -0.1(2) . . . . ?
C008 C009 C00A C00K -169.83(13) . . . . ?
C008 C009 C00G C00D -6.80(15) . . . . ?
C008 C009 C00L C00J 151.97(15) . . . . ?
C008 C00F C00E C00D -41.50(15) . . . . ?
C009 C00A C00K C00P -176.66(19) . . . . ?
C009 C00G C00D C00C 84.18(14) . . . . ?
C009 C00G C00D C00E -38.72(14) . . . . ?
C00A C00K C00P C00N -0.1(2) . . . . ?
C00B C00F C00E C00D 126.32(16) . . . . ?
C00C C00D C00E C00F -58.65(14) . . . . ?
C00K C00P C00N C00M 0.0(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_mo_241220wayamakaneko2_0m
_database_code_depnum_ccdc_archive 'CCDC 2466308'
loop_
_audit_author_name
_audit_author_address
'Toshiaki Wayama'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-06-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
toshiakiw@g.ecc.u-tokyo.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        241220WayamaKaneko
_chemical_formula_moiety         'C21 H20 N2 O3'
_chemical_formula_sum            'C21 H20 N2 O3'
_chemical_formula_weight         348.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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                   9.3868(6)
_cell_length_b                   10.7718(6)
_cell_length_c                   18.7809(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.291(3)
_cell_angle_gamma                90
_cell_volume                     1862.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3100
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      19.89
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6670
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0961 before and 0.0658 after correction.
The Ratio of minimum to maximum transmission is 0.8946.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26401
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1905
_reflns_number_total             4037
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.011
_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)+(0.0481P)²+0.2744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1352
_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:
 C009(H00A,H00B), C00F(H00C,H00D), C00G(H00E,H00F), C00I(H00G,H00I), C00M(H00M,
 H00N)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00N(H00O), C00O(H00P)
2.c X=CH2 refined with riding coordinates:
 C00K(H00K,H00L)
2.d Idealised Me refined as rotating group:
 C00P(H00Q,H00R,H00S)
2.e :
 C00Q(H00T)
;
_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
O001 O 0.77208(17) 0.96228(13) 0.35232(9) 0.0740(5) Uani 1 1 d . . . . .
O002 O 0.78080(17) 0.69440(14) 0.16598(9) 0.0784(5) Uani 1 1 d . . . . .
N003 N 0.71573(17) 0.69115(14) 0.27621(9) 0.0537(4) Uani 1 1 d . . . . .
O004 O 0.57025(19) 1.07387(13) 0.33015(10) 0.0882(5) Uani 1 1 d . . . . .
N005 N 0.45456(18) 0.86470(15) 0.42833(9) 0.0596(5) Uani 1 1 d . . . . .
C006 C 0.6460(2) 0.74275(17) 0.32990(11) 0.0521(5) Uani 1 1 d . . . . .
C007 C 0.5500(2) 0.85419(17) 0.31285(10) 0.0518(5) Uani 1 1 d . . . . .
C008 C 0.6304(3) 0.97574(19) 0.33319(11) 0.0577(6) Uani 1 1 d . . . . .
C009 C 0.4189(2) 0.85111(19) 0.34965(11) 0.0579(6) Uani 1 1 d . . . . .
H00A H 0.352880 0.917254 0.329718 0.069 Uiso 1 1 calc R U . . .
H00B H 0.368262 0.772998 0.338045 0.069 Uiso 1 1 calc R U . . .
C00A C 0.7095(2) 0.73880(18) 0.20717(13) 0.0585(6) Uani 1 1 d . . . . .
C00B C 0.6118(2) 0.84661(19) 0.18954(11) 0.0593(6) Uani 1 1 d . . . . .
C00C C 0.7795(2) 0.57912(18) 0.37856(13) 0.0629(6) Uani 1 1 d . . . . .
C00D C 0.7991(2) 0.58940(18) 0.30717(13) 0.0596(6) Uani 1 1 d . . . . .
C00E C 0.6829(2) 0.67734(18) 0.39202(12) 0.0604(6) Uani 1 1 d . . . . .
C00F C 0.4911(2) 0.85786(19) 0.23008(10) 0.0597(6) Uani 1 1 d . . . . .
H00C H 0.422884 0.790335 0.216466 0.072 Uiso 1 1 calc R U . . .
H00D H 0.439891 0.935364 0.217284 0.072 Uiso 1 1 calc R U . . .
C00G C 0.3338(3) 0.9255(2) 0.45420(13) 0.0728(7) Uani 1 1 d . . . . .
H00E H 0.318561 1.007072 0.432143 0.087 Uiso 1 1 calc R U . . .
H00F H 0.361200 0.937016 0.506315 0.087 Uiso 1 1 calc R U . . .
C00H C 0.8837(2) 0.5072(2) 0.27680(15) 0.0765(7) Uani 1 1 d . . . . .
H00H H 0.896164 0.515416 0.229107 0.092 Uiso 1 1 calc R U . . .
C00I C 0.4953(3) 0.7476(2) 0.46670(12) 0.0785(7) Uani 1 1 d . . . . .
H00G H 0.427381 0.683658 0.445510 0.094 Uiso 1 1 calc R U . . .
H00I H 0.486737 0.757428 0.517029 0.094 Uiso 1 1 calc R U . . .
C00J C 0.8475(3) 0.4825(2) 0.42195(15) 0.0813(8) Uani 1 1 d . . . . .
H00J H 0.836186 0.473676 0.469789 0.098 Uiso 1 1 calc R U . . .
C00K C 0.6397(3) 0.9284(2) 0.14214(13) 0.0889(8) Uani 1 1 d . . . . .
H00K H 0.719769 0.917781 0.120402 0.107 Uiso 1 1 calc R U . . .
H00L H 0.579369 0.996912 0.130346 0.107 Uiso 1 1 calc R U . . .
C00L C 0.1961(3) 0.8562(3) 0.43808(14) 0.0829(7) Uani 1 1 d . . . . .
C00M C 0.6479(3) 0.7050(2) 0.46428(13) 0.0864(8) Uani 1 1 d . . . . .
H00M H 0.714756 0.768475 0.487182 0.104 Uiso 1 1 calc R U . . .
H00N H 0.667339 0.630724 0.493813 0.104 Uiso 1 1 calc R U . . .
C00N C 0.9486(3) 0.4123(2) 0.3211(2) 0.0954(9) Uani 1 1 d . . . . .
H00O H 1.005380 0.354646 0.302511 0.114 Uiso 1 1 calc R U . . .
C00O C 0.9318(3) 0.4007(2) 0.3920(2) 0.0991(10) Uani 1 1 d . . . . .
H00P H 0.978342 0.336151 0.420260 0.119 Uiso 1 1 calc R U . . .
C00P C 0.8560(3) 1.0765(2) 0.36748(17) 0.1038(10) Uani 1 1 d . . . . .
H00Q H 0.850684 1.122678 0.323306 0.156 Uiso 1 1 calc R U . . .
H00R H 0.955548 1.056492 0.387279 0.156 Uiso 1 1 calc R U . . .
H00S H 0.817069 1.125600 0.401829 0.156 Uiso 1 1 calc R U . . .
C00Q C 0.0903(4) 0.7998(3) 0.42248(18) 0.1257(12) Uani 1 1 d . . . . .
H00T H 0.004950 0.754284 0.409882 0.151 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C008 1.316(2) . ?
O001 C00P 1.459(3) . ?
O002 C00A 1.216(2) . ?
N003 C006 1.419(2) . ?
N003 C00A 1.385(3) . ?
N003 C00D 1.405(2) . ?
O004 C008 1.195(2) . ?
N005 C009 1.457(2) . ?
N005 C00G 1.472(3) . ?
N005 C00I 1.466(3) . ?
C006 C007 1.497(3) . ?
C006 C00E 1.349(3) . ?
C007 C008 1.522(3) . ?
C007 C009 1.525(3) . ?
C007 C00F 1.545(3) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C00A C00B 1.477(3) . ?
C00B C00F 1.488(3) . ?
C00B C00K 1.315(3) . ?
C00C C00D 1.393(3) . ?
C00C C00E 1.447(3) . ?
C00C C00J 1.397(3) . ?
C00D C00H 1.385(3) . ?
C00E C00M 1.488(3) . ?
C00F H00C 0.9700 . ?
C00F H00D 0.9700 . ?
C00G H00E 0.9700 . ?
C00G H00F 0.9700 . ?
C00G C00L 1.472(3) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.382(4) . ?
C00I H00G 0.9700 . ?
C00I H00I 0.9700 . ?
C00I C00M 1.513(3) . ?
C00J H00J 0.9300 . ?
C00J C00O 1.375(4) . ?
C00K H00K 0.9300 . ?
C00K H00L 0.9300 . ?
C00L C00Q 1.152(3) . ?
C00M H00M 0.9700 . ?
C00M H00N 0.9700 . ?
C00N H00O 0.9300 . ?
C00N C00O 1.377(4) . ?
C00O H00P 0.9300 . ?
C00P H00Q 0.9600 . ?
C00P H00R 0.9600 . ?
C00P H00S 0.9600 . ?
C00Q H00T 0.9300 . ?

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
C008 O001 C00P 116.02(18) . . ?
C00A N003 C006 125.40(17) . . ?
C00A N003 C00D 126.49(18) . . ?
C00D N003 C006 107.98(17) . . ?
C009 N005 C00G 109.92(16) . . ?
C009 N005 C00I 113.47(16) . . ?
C00I N005 C00G 111.38(18) . . ?
N003 C006 C007 120.27(17) . . ?
C00E C006 N003 109.50(17) . . ?
C00E C006 C007 130.23(18) . . ?
C006 C007 C008 112.82(16) . . ?
C006 C007 C009 113.00(16) . . ?
C006 C007 C00F 108.51(16) . . ?
C008 C007 C009 108.03(16) . . ?
C008 C007 C00F 107.01(16) . . ?
C009 C007 C00F 107.17(16) . . ?
O001 C008 C007 113.50(17) . . ?
O004 C008 O001 123.6(2) . . ?
O004 C008 C007 122.9(2) . . ?
N005 C009 C007 114.32(16) . . ?
N005 C009 H00A 108.7 . . ?
N005 C009 H00B 108.7 . . ?
C007 C009 H00A 108.7 . . ?
C007 C009 H00B 108.7 . . ?
H00A C009 H00B 107.6 . . ?
O002 C00A N003 121.5(2) . . ?
O002 C00A C00B 124.2(2) . . ?
N003 C00A C00B 114.33(18) . . ?
C00A C00B C00F 116.80(18) . . ?
C00K C00B C00A 118.8(2) . . ?
C00K C00B C00F 124.4(2) . . ?
C00D C00C C00E 108.38(18) . . ?
C00D C00C C00J 119.3(2) . . ?
C00J C00C C00E 132.3(2) . . ?
C00C C00D N003 107.00(18) . . ?
C00H C00D N003 130.3(2) . . ?
C00H C00D C00C 122.7(2) . . ?
C006 C00E C00C 107.14(19) . . ?
C006 C00E C00M 128.26(19) . . ?
C00C C00E C00M 124.3(2) . . ?
C007 C00F H00C 109.5 . . ?
C007 C00F H00D 109.5 . . ?
C00B C00F C007 110.78(17) . . ?
C00B C00F H00C 109.5 . . ?
C00B C00F H00D 109.5 . . ?
H00C C00F H00D 108.1 . . ?
N005 C00G H00E 108.7 . . ?
N005 C00G H00F 108.7 . . ?
N005 C00G C00L 114.13(18) . . ?
H00E C00G H00F 107.6 . . ?
C00L C00G H00E 108.7 . . ?
C00L C00G H00F 108.7 . . ?
C00D C00H H00H 121.8 . . ?
C00N C00H C00D 116.5(3) . . ?
C00N C00H H00H 121.8 . . ?
N005 C00I H00G 108.8 . . ?
N005 C00I H00I 108.8 . . ?
N005 C00I C00M 113.8(2) . . ?
H00G C00I H00I 107.7 . . ?
C00M C00I H00G 108.8 . . ?
C00M C00I H00I 108.8 . . ?
C00C C00J H00J 120.9 . . ?
C00O C00J C00C 118.2(3) . . ?
C00O C00J H00J 120.9 . . ?
C00B C00K H00K 120.0 . . ?
C00B C00K H00L 120.0 . . ?
H00K C00K H00L 120.0 . . ?
C00Q C00L C00G 176.7(3) . . ?
C00E C00M C00I 117.9(2) . . ?
C00E C00M H00M 107.8 . . ?
C00E C00M H00N 107.8 . . ?
C00I C00M H00M 107.8 . . ?
C00I C00M H00N 107.8 . . ?
H00M C00M H00N 107.2 . . ?
C00H C00N H00O 119.0 . . ?
C00O C00N C00H 121.9(3) . . ?
C00O C00N H00O 119.0 . . ?
C00J C00O C00N 121.4(3) . . ?
C00J C00O H00P 119.3 . . ?
C00N C00O H00P 119.3 . . ?
O001 C00P H00Q 109.5 . . ?
O001 C00P H00R 109.5 . . ?
O001 C00P H00S 109.5 . . ?
H00Q C00P H00R 109.5 . . ?
H00Q C00P H00S 109.5 . . ?
H00R C00P H00S 109.5 . . ?
C00L C00Q H00T 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O002 C00A C00B C00F 155.8(2) . . . . ?
O002 C00A C00B C00K -27.1(3) . . . . ?
N003 C006 C007 C008 -93.2(2) . . . . ?
N003 C006 C007 C009 143.88(17) . . . . ?
N003 C006 C007 C00F 25.2(2) . . . . ?
N003 C006 C00E C00C -0.3(2) . . . . ?
N003 C006 C00E C00M 173.3(2) . . . . ?
N003 C00A C00B C00F -24.9(2) . . . . ?
N003 C00A C00B C00K 152.2(2) . . . . ?
N003 C00D C00H C00N -177.4(2) . . . . ?
N005 C00I C00M C00E -61.8(3) . . . . ?
C006 N003 C00A O002 174.58(18) . . . . ?
C006 N003 C00A C00B -4.7(3) . . . . ?
C006 N003 C00D C00C 0.3(2) . . . . ?
C006 N003 C00D C00H 178.2(2) . . . . ?
C006 C007 C008 O001 9.0(2) . . . . ?
C006 C007 C008 O004 -172.8(2) . . . . ?
C006 C007 C009 N005 68.6(2) . . . . ?
C006 C007 C00F C00B -51.3(2) . . . . ?
C006 C00E C00M C00I 43.1(4) . . . . ?
C007 C006 C00E C00C -179.61(19) . . . . ?
C007 C006 C00E C00M -5.9(4) . . . . ?
C008 C007 C009 N005 -57.0(2) . . . . ?
C008 C007 C00F C00B 70.7(2) . . . . ?
C009 N005 C00G C00L 60.9(2) . . . . ?
C009 N005 C00I C00M 76.8(2) . . . . ?
C009 C007 C008 O001 134.61(18) . . . . ?
C009 C007 C008 O004 -47.2(3) . . . . ?
C009 C007 C00F C00B -173.59(16) . . . . ?
C00A N003 C006 C007 3.3(3) . . . . ?
C00A N003 C006 C00E -176.04(17) . . . . ?
C00A N003 C00D C00C 176.31(17) . . . . ?
C00A N003 C00D C00H -5.8(3) . . . . ?
C00A C00B C00F C007 54.1(2) . . . . ?
C00C C00D C00H C00N 0.3(3) . . . . ?
C00C C00E C00M C00I -144.2(2) . . . . ?
C00C C00J C00O C00N -0.4(4) . . . . ?
C00D N003 C006 C007 179.39(16) . . . . ?
C00D N003 C006 C00E 0.0(2) . . . . ?
C00D N003 C00A O002 -0.8(3) . . . . ?
C00D N003 C00A C00B 179.92(17) . . . . ?
C00D C00C C00E C006 0.5(2) . . . . ?
C00D C00C C00E C00M -173.5(2) . . . . ?
C00D C00C C00J C00O -0.1(3) . . . . ?
C00D C00H C00N C00O -0.8(4) . . . . ?
C00E C006 C007 C008 86.0(3) . . . . ?
C00E C006 C007 C009 -36.9(3) . . . . ?
C00E C006 C007 C00F -155.6(2) . . . . ?
C00E C00C C00D N003 -0.5(2) . . . . ?
C00E C00C C00D C00H -178.63(18) . . . . ?
C00E C00C C00J C00O 178.3(2) . . . . ?
C00F C007 C008 O001 -110.29(19) . . . . ?
C00F C007 C008 O004 67.9(2) . . . . ?
C00F C007 C009 N005 -171.95(16) . . . . ?
C00G N005 C009 C007 149.96(17) . . . . ?
C00G N005 C00I C00M -158.50(19) . . . . ?
C00H C00N C00O C00J 0.9(4) . . . . ?
C00I N005 C009 C007 -84.6(2) . . . . ?
C00I N005 C00G C00L -65.7(3) . . . . ?
C00J C00C C00D N003 178.26(18) . . . . ?
C00J C00C C00D C00H 0.1(3) . . . . ?
C00J C00C C00E C006 -178.0(2) . . . . ?
C00J C00C C00E C00M 8.0(4) . . . . ?
C00K C00B C00F C007 -122.8(2) . . . . ?
C00P O001 C008 O004 -2.4(3) . . . . ?
C00P O001 C008 C007 175.82(19) . . . . ?

_olex2_exptl_crystal_mounting_method 'manual mounting'
_olex2_submission_original_sample_id mo_241220wayamakaneko2_0m
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_10
_database_code_depnum_ccdc_archive 'CCDC 2179524'
loop_
_audit_author_name
_audit_author_address
'Toshiaki Wayama'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-06-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
toshiakiw@g.ecc.u-tokyo.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        250619WayamaKaneko
_chemical_formula_moiety         'C21 H23 N2 O4'
_chemical_formula_sum            'C21 H23 N2 O4'
_chemical_formula_weight         367.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H22 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9894(10)
_cell_length_b                   12.6714(7)
_cell_length_c                   13.1685(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.823(9)
_cell_angle_gamma                90
_cell_volume                     1934.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3907
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.1120
_cell_measurement_theta_min      3.0090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             780
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
14 11 -11 0.2460
-3 -12 -11 0.0620
13 11 -11 0.2446
-10 2 18 0.0601
1 13 11 0.1207
3 10 12 0.1142
6 6 12 0.1142
11 -4 8 0.1142
-7 -6 -11 0.1011
-7 15 -4 0.1237
10 -10 6 0.1088
17 -6 -6 0.1780
-2 17 5 0.1345

_exptl_crystal_preparation       'vapor difussion'
_exptl_crystal_recrystallization_method vapordifussion
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.192
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
13.6630 10.7130 -11.0425 -0.1024 0.2301 0.9678
-2.8032 -11.8885 -10.8149 0.4062 -0.9123 -0.0526
13.2586 11.2786 -10.6663 -0.0865 0.2663 0.9600
-9.7757 2.0446 18.3524 -0.2011 0.6189 -0.7593
1.0000 13.0000 11.0000 -0.2964 0.9606 0.0269
3.0000 10.0000 12.0000 -0.4988 0.8618 -0.0255
6.0000 6.0000 12.0000 -0.7308 0.6900 -0.0465
11.0000 -4.0000 8.0000 -1.0061 0.1217 -0.0462
-7.0000 -6.0000 -11.0000 0.7435 -0.6640 -0.0103
-7.0000 15.0000 -4.0000 0.8056 0.5416 0.3122
10.0000 -10.0000 6.0000 -0.9690 -0.2281 -0.1651
17.0000 -6.0000 -6.0000 -0.7803 -0.3789 0.4829
-2.0000 17.0000 5.0000 0.1877 0.9444 0.2274

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13260
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.100
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   29.15    --   30.00  54.00 -60.00  193
  2  ω    -74.00 119.00   1.00   29.15    --   30.00  54.00  90.00  193
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2507
_reflns_number_total             3951
_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 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.040
_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)+(0.0837P)²+0.1845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1522
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N004(H004), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00F(H00C,H00D), C00G(H00E,H00F), C00J(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00K(H00K), C00L(H00L), C00N(H00N)
2.d X=CH2 refined with riding coordinates:
 C00Q(H00S,H00T)
2.e Idealised Me refined as rotating group:
 C00O(H00J,H00M,H00O), C00P(H00P,H00Q,H00R)
2.f :
 C00R(H00U)
;
_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
O001 O 0.43371(11) 0.70006(11) 0.67683(12) 0.0579(4) Uani 1 1 d . . . . .
O002 O 0.47607(13) 0.52917(13) 0.71232(14) 0.0688(5) Uani 1 1 d . . . . .
N003 N 0.17720(13) 0.43890(13) 0.63529(12) 0.0429(4) Uani 1 1 d . . . . .
N004 N 0.32632(13) 0.58618(13) 0.42026(12) 0.0439(4) Uani 1 1 d . . . . .
H004 H 0.404798 0.576042 0.485175 0.053 Uiso 1 1 calc R U . . .
O005 O 0.25380(16) 0.55841(14) 0.90862(13) 0.0772(5) Uani 1 1 d . . . . .
C006 C 0.40777(16) 0.59755(16) 0.66558(15) 0.0425(5) Uani 1 1 d . . . . .
O007 O 0.34172(17) 0.43393(19) 0.85866(15) 0.1002(7) Uani 1 1 d . . . . .
C008 C 0.28026(15) 0.58333(15) 0.58520(15) 0.0400(4) Uani 1 1 d . . . . .
H008 H 0.236317 0.626045 0.616444 0.048 Uiso 1 1 calc R U . . .
C009 C 0.24114(14) 0.47148(15) 0.57875(14) 0.0389(4) Uani 1 1 d . . . . .
C00A C 0.25396(15) 0.38920(15) 0.51921(15) 0.0405(4) Uani 1 1 d . . . . .
C00B C 0.19802(15) 0.29937(15) 0.53992(15) 0.0419(4) Uani 1 1 d . . . . .
C00C C 0.15296(15) 0.33242(16) 0.61381(15) 0.0436(5) Uani 1 1 d . . . . .
C00D C 0.25335(16) 0.62972(16) 0.46763(15) 0.0434(5) Uani 1 1 d . . . . .
H00A H 0.171560 0.615496 0.414448 0.052 Uiso 1 1 calc R U . . .
H00B H 0.263887 0.707213 0.474616 0.052 Uiso 1 1 calc R U . . .
C00E C 0.16256(17) 0.49789(17) 0.71956(16) 0.0499(5) Uani 1 1 d . . . . .
C00F C 0.33898(18) 0.66037(18) 0.34115(17) 0.0544(5) Uani 1 1 d . . . . .
H00C H 0.394245 0.630690 0.316055 0.065 Uiso 1 1 calc R U . . .
H00D H 0.371821 0.727248 0.381743 0.065 Uiso 1 1 calc R U . . .
C00G C 0.31776(18) 0.39118(16) 0.44901(17) 0.0506(5) Uani 1 1 d . . . . .
H00E H 0.301962 0.324432 0.405463 0.061 Uiso 1 1 calc R U . . .
H00F H 0.401490 0.393378 0.500948 0.061 Uiso 1 1 calc R U . . .
C00H C 0.2644(2) 0.49380(19) 0.83602(17) 0.0571(6) Uani 1 1 d . . . . .
C00I C 0.18536(17) 0.19370(17) 0.50557(18) 0.0529(5) Uani 1 1 d . . . . .
H00I H 0.214333 0.169753 0.455038 0.063 Uiso 1 1 calc R U . . .
C00J C 0.28838(18) 0.48295(16) 0.36574(17) 0.0507(5) Uani 1 1 d . . . . .
H00G H 0.324456 0.470134 0.314781 0.061 Uiso 1 1 calc R U . . .
H00H H 0.203770 0.484829 0.318003 0.061 Uiso 1 1 calc R U . . .
C00K C 0.09569(18) 0.2632(2) 0.65344(18) 0.0595(6) Uani 1 1 d . . . . .
H00K H 0.064580 0.286303 0.702517 0.071 Uiso 1 1 calc R U . . .
C00L C 0.1304(2) 0.12480(19) 0.5459(2) 0.0651(6) Uani 1 1 d . . . . .
H00L H 0.122663 0.052688 0.523988 0.078 Uiso 1 1 calc R U . . .
C00M C 0.2296(2) 0.6832(2) 0.24035(19) 0.0639(6) Uani 1 1 d . . . . .
C00N C 0.0863(2) 0.15936(19) 0.6181(2) 0.0668(7) Uani 1 1 d . . . . .
H00N H 0.048278 0.110176 0.644103 0.080 Uiso 1 1 calc R U . . .
C00O C 0.55159(18) 0.7287(2) 0.7519(2) 0.0685(7) Uani 1 1 d . . . . .
H00J H 0.603515 0.693076 0.727299 0.103 Uiso 1 1 calc R U . . .
H00M H 0.570444 0.707073 0.829797 0.103 Uiso 1 1 calc R U . . .
H00O H 0.560776 0.805254 0.749527 0.103 Uiso 1 1 calc R U . . .
C00P C 0.3491(3) 0.5572(2) 1.0237(2) 0.0935(9) Uani 1 1 d . . . . .
H00P H 0.420310 0.579223 1.021275 0.140 Uiso 1 1 calc R U . . .
H00Q H 0.358798 0.485669 1.054995 0.140 Uiso 1 1 calc R U . . .
H00R H 0.332215 0.605912 1.072041 0.140 Uiso 1 1 calc R U . . .
C00Q C 0.0682(2) 0.5503(3) 0.6957(2) 0.0901(9) Uani 1 1 d . . . . .
H00S H 0.007114 0.549734 0.620412 0.108 Uiso 1 1 calc R U . . .
H00T H 0.060460 0.589227 0.753536 0.108 Uiso 1 1 calc R U . . .
C00R C 0.1398(3) 0.6968(2) 0.1616(2) 0.0927(9) Uani 1 1 d . . . . .
H00U H 0.067041 0.707813 0.097732 0.111 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C006 1.333(2) . ?
O001 C00O 1.445(2) . ?
O002 C006 1.193(2) . ?
N003 C009 1.405(2) . ?
N003 C00C 1.385(2) . ?
N003 C00E 1.420(2) . ?
N004 H004 1.0000 . ?
N004 C00D 1.458(2) . ?
N004 C00F 1.467(2) . ?
N004 C00J 1.466(2) . ?
O005 C00H 1.312(3) . ?
O005 C00P 1.462(3) . ?
C006 C008 1.521(3) . ?
O007 C00H 1.185(3) . ?
C008 H008 1.0000 . ?
C008 C009 1.495(3) . ?
C008 C00D 1.541(2) . ?
C009 C00A 1.359(2) . ?
C00A C00B 1.441(3) . ?
C00A C00G 1.494(3) . ?
C00B C00C 1.407(3) . ?
C00B C00I 1.399(3) . ?
C00C C00K 1.395(3) . ?
C00D H00A 0.9900 . ?
C00D H00B 0.9900 . ?
C00E C00H 1.508(3) . ?
C00E C00Q 1.302(3) . ?
C00F H00C 0.9900 . ?
C00F H00D 0.9900 . ?
C00F C00M 1.470(3) . ?
C00G H00E 0.9900 . ?
C00G H00F 0.9900 . ?
C00G C00J 1.524(3) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.377(3) . ?
C00J H00G 0.9900 . ?
C00J H00H 0.9900 . ?
C00K H00K 0.9500 . ?
C00K C00N 1.382(3) . ?
C00L H00L 0.9500 . ?
C00L C00N 1.383(4) . ?
C00M C00R 1.172(3) . ?
C00N H00N 0.9500 . ?
C00O H00J 0.9800 . ?
C00O H00M 0.9800 . ?
C00O H00O 0.9800 . ?
C00P H00P 0.9800 . ?
C00P H00Q 0.9800 . ?
C00P H00R 0.9800 . ?
C00Q H00S 0.9500 . ?
C00Q H00T 0.9500 . ?
C00R H00U 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 O001 C00O 117.20(17) . . ?
C009 N003 C00E 125.40(16) . . ?
C00C N003 C009 108.20(14) . . ?
C00C N003 C00E 125.02(15) . . ?
C00D N004 H004 107.0 . . ?
C00D N004 C00F 111.37(16) . . ?
C00D N004 C00J 114.04(15) . . ?
C00F N004 H004 107.0 . . ?
C00J N004 H004 107.0 . . ?
C00J N004 C00F 110.16(15) . . ?
C00H O005 C00P 115.5(2) . . ?
O001 C006 C008 109.51(16) . . ?
O002 C006 O001 123.94(18) . . ?
O002 C006 C008 126.56(19) . . ?
C006 C008 H008 107.1 . . ?
C006 C008 C00D 109.63(14) . . ?
C009 C008 C006 112.78(15) . . ?
C009 C008 H008 107.1 . . ?
C009 C008 C00D 112.78(15) . . ?
C00D C008 H008 107.1 . . ?
N003 C009 C008 121.04(15) . . ?
C00A C009 N003 109.63(16) . . ?
C00A C009 C008 129.28(16) . . ?
C009 C00A C00B 107.06(16) . . ?
C009 C00A C00G 126.18(17) . . ?
C00B C00A C00G 126.73(17) . . ?
C00C C00B C00A 107.36(16) . . ?
C00I C00B C00A 133.67(18) . . ?
C00I C00B C00C 118.93(18) . . ?
N003 C00C C00B 107.70(15) . . ?
N003 C00C C00K 130.29(18) . . ?
C00K C00C C00B 122.01(19) . . ?
N004 C00D C008 112.88(15) . . ?
N004 C00D H00A 109.0 . . ?
N004 C00D H00B 109.0 . . ?
C008 C00D H00A 109.0 . . ?
C008 C00D H00B 109.0 . . ?
H00A C00D H00B 107.8 . . ?
N003 C00E C00H 114.30(17) . . ?
C00Q C00E N003 121.6(2) . . ?
C00Q C00E C00H 124.1(2) . . ?
N004 C00F H00C 108.9 . . ?
N004 C00F H00D 108.9 . . ?
N004 C00F C00M 113.28(16) . . ?
H00C C00F H00D 107.7 . . ?
C00M C00F H00C 108.9 . . ?
C00M C00F H00D 108.9 . . ?
C00A C00G H00E 108.4 . . ?
C00A C00G H00F 108.4 . . ?
C00A C00G C00J 115.41(17) . . ?
H00E C00G H00F 107.5 . . ?
C00J C00G H00E 108.4 . . ?
C00J C00G H00F 108.4 . . ?
O005 C00H C00E 112.8(2) . . ?
O007 C00H O005 124.9(2) . . ?
O007 C00H C00E 122.2(2) . . ?
C00B C00I H00I 120.4 . . ?
C00L C00I C00B 119.2(2) . . ?
C00L C00I H00I 120.4 . . ?
N004 C00J C00G 114.12(16) . . ?
N004 C00J H00G 108.7 . . ?
N004 C00J H00H 108.7 . . ?
C00G C00J H00G 108.7 . . ?
C00G C00J H00H 108.7 . . ?
H00G C00J H00H 107.6 . . ?
C00C C00K H00K 121.5 . . ?
C00N C00K C00C 117.0(2) . . ?
C00N C00K H00K 121.5 . . ?
C00I C00L H00L 119.6 . . ?
C00I C00L C00N 120.8(2) . . ?
C00N C00L H00L 119.6 . . ?
C00R C00M C00F 176.3(3) . . ?
C00K C00N C00L 122.1(2) . . ?
C00K C00N H00N 118.9 . . ?
C00L C00N H00N 118.9 . . ?
O001 C00O H00J 109.5 . . ?
O001 C00O H00M 109.5 . . ?
O001 C00O H00O 109.5 . . ?
H00J C00O H00M 109.5 . . ?
H00J C00O H00O 109.5 . . ?
H00M C00O H00O 109.5 . . ?
O005 C00P H00P 109.5 . . ?
O005 C00P H00Q 109.5 . . ?
O005 C00P H00R 109.5 . . ?
H00P C00P H00Q 109.5 . . ?
H00P C00P H00R 109.5 . . ?
H00Q C00P H00R 109.5 . . ?
C00E C00Q H00S 120.0 . . ?
C00E C00Q H00T 120.0 . . ?
H00S C00Q H00T 120.0 . . ?
C00M C00R H00U 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C006 C008 C009 -173.20(15) . . . . ?
O001 C006 C008 C00D 60.24(18) . . . . ?
O002 C006 C008 C009 7.0(3) . . . . ?
O002 C006 C008 C00D -119.6(2) . . . . ?
N003 C009 C00A C00B -1.1(2) . . . . ?
N003 C009 C00A C00G -179.19(17) . . . . ?
N003 C00C C00K C00N -178.94(19) . . . . ?
N003 C00E C00H O005 172.63(17) . . . . ?
N003 C00E C00H O007 -11.0(3) . . . . ?
C006 C008 C009 N003 103.54(18) . . . . ?
C006 C008 C009 C00A -79.4(2) . . . . ?
C006 C008 C00D N004 54.6(2) . . . . ?
C008 C009 C00A C00B -178.47(16) . . . . ?
C008 C009 C00A C00G 3.5(3) . . . . ?
C009 N003 C00C C00B -2.29(18) . . . . ?
C009 N003 C00C C00K 177.54(19) . . . . ?
C009 N003 C00E C00H -78.7(2) . . . . ?
C009 N003 C00E C00Q 101.3(3) . . . . ?
C009 C008 C00D N004 -71.91(19) . . . . ?
C009 C00A C00B C00C -0.3(2) . . . . ?
C009 C00A C00B C00I -177.84(19) . . . . ?
C009 C00A C00G C00J -48.8(3) . . . . ?
C00A C00B C00C N003 1.59(19) . . . . ?
C00A C00B C00C C00K -178.25(17) . . . . ?
C00A C00B C00I C00L 176.6(2) . . . . ?
C00A C00G C00J N004 68.2(2) . . . . ?
C00B C00A C00G C00J 133.49(19) . . . . ?
C00B C00C C00K C00N 0.9(3) . . . . ?
C00B C00I C00L C00N 1.1(3) . . . . ?
C00C N003 C009 C008 179.75(15) . . . . ?
C00C N003 C009 C00A 2.17(19) . . . . ?
C00C N003 C00E C00H 86.3(2) . . . . ?
C00C N003 C00E C00Q -93.7(3) . . . . ?
C00C C00B C00I C00L -0.7(3) . . . . ?
C00C C00K C00N C00L -0.5(3) . . . . ?
C00D N004 C00F C00M -63.5(2) . . . . ?
C00D N004 C00J C00G -77.1(2) . . . . ?
C00D C008 C009 N003 -131.60(16) . . . . ?
C00D C008 C009 C00A 45.5(2) . . . . ?
C00E N003 C009 C008 -13.1(3) . . . . ?
C00E N003 C009 C00A 169.27(17) . . . . ?
C00E N003 C00C C00B -169.45(17) . . . . ?
C00E N003 C00C C00K 10.4(3) . . . . ?
C00F N004 C00D C008 -153.66(15) . . . . ?
C00F N004 C00J C00G 156.79(17) . . . . ?
C00G C00A C00B C00C 177.76(18) . . . . ?
C00G C00A C00B C00I 0.2(3) . . . . ?
C00I C00B C00C N003 179.58(16) . . . . ?
C00I C00B C00C C00K -0.3(3) . . . . ?
C00I C00L C00N C00K -0.5(4) . . . . ?
C00J N004 C00D C008 80.91(19) . . . . ?
C00J N004 C00F C00M 64.1(2) . . . . ?
C00O O001 C006 O002 -1.0(3) . . . . ?
C00O O001 C006 C008 179.11(16) . . . . ?
C00P O005 C00H O007 2.9(4) . . . . ?
C00P O005 C00H C00E 179.2(2) . . . . ?
C00Q C00E C00H O005 -7.3(3) . . . . ?
C00Q C00E C00H O007 169.1(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'manual mounting'
_olex2_submission_original_sample_id 250619WayamaKaneko
_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 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.943

####################################################################### 
# 
# 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_240926WayamaKaneko
_database_code_depnum_ccdc_archive 'CCDC 2466307'
loop_
_audit_author_name
_audit_author_address
'Toshiaki Wayama'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-06-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
toshiakiw@g.ecc.u-tokyo.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        240916wayamakaneko
_chemical_formula_moiety         'C26 H22 N2 O3'
_chemical_formula_sum            'C26 H22 N2 O3'
_chemical_formula_weight         410.45
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        P1
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.24620(10)
_cell_length_b                   10.95700(10)
_cell_length_c                   11.5332(2)
_cell_angle_alpha                99.6020(10)
_cell_angle_beta                 99.4950(10)
_cell_angle_gamma                111.5150(10)
_cell_volume                     1038.71(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      4.01
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0809 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.9214.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_preparation       vapordifussion
_exptl_crystal_recrystallization_method vapordifussion
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15495
_diffrn_reflns_point_group_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.260
_diffrn_reflns_theta_min         4.011
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                6748
_reflns_number_total             6829
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(5)
_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     561
_refine_ls_number_reflns         6829
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.042
_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)+(0.0350P)²+0.1122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0681
_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:
 C00G(H00A,H00B), C00O(H00C,H00D), C00V(H00E,H00F), C012(H01A,H01B), C016(H01K,
 H01M), C017(H01C,H01D), C01D(H01P,H01Q), C01M(H01V,H01W)
2.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00Q(H00Q), C00Z(H00Z), C010(H010), C013(H013), C014(H014),
 C015(H015), C018(H018), C019(H019), C01A(H01N), C01B(H01O), C01C(H01E),
 C01E(H01F), C01F(H01R), C01G(H01S), C01H(H01T), C01J(H01J), C01K(H01U),
 C01L(H01L), C01O(H01X)
2.c Idealised Me refined as rotating group:
 C01N(H01G,H01H,H01I), C01P(H01Y,H,HA)
2.d :
 C21(H21), C20(H20)
;
_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
O001 O 1.09091(17) 1.01507(15) 0.05456(13) 0.0370(3) Uani 1 1 d . . . . .
O002 O 0.61720(17) 0.53325(14) 0.59028(14) 0.0369(3) Uani 1 1 d . . . . .
O003 O 0.91997(18) 0.91161(15) -0.12741(13) 0.0393(3) Uani 1 1 d . . . . .
O004 O 0.48794(19) 0.64890(14) 0.66953(15) 0.0410(4) Uani 1 1 d . . . . .
O005 O 0.46885(19) 0.21132(15) 0.83398(13) 0.0373(3) Uani 1 1 d . . . . .
O006 O 1.0387(2) 0.65424(15) 0.21053(14) 0.0432(4) Uani 1 1 d . . . . .
N007 N 0.44291(19) 0.22196(15) 0.63380(14) 0.0269(3) Uani 1 1 d . . . . .
N008 N 0.96197(18) 0.83137(15) 0.24384(14) 0.0259(3) Uani 1 1 d . . . . .
N009 N 0.64475(19) 0.92597(15) -0.00376(14) 0.0276(3) Uani 1 1 d . . . . .
N00A N 0.1979(2) 0.43266(16) 0.45653(15) 0.0300(3) Uani 1 1 d . . . . .
C00B C 0.4957(2) 0.54388(18) 0.63135(16) 0.0259(4) Uani 1 1 d . . . . .
C00C C 0.9536(2) 0.92512(17) -0.01974(16) 0.0253(4) Uani 1 1 d . . . . .
C00D C 0.3831(2) 0.28712(17) 0.55697(17) 0.0244(4) Uani 1 1 d . . . . .
C00E C 0.8767(2) 0.89058(18) 0.17934(16) 0.0242(4) Uani 1 1 d . . . . .
C00F C 0.8890(2) 0.71017(17) 0.04560(17) 0.0250(4) Uani 1 1 d . . . . .
C00G C 0.6705(2) 0.80024(18) -0.01551(17) 0.0261(4) Uani 1 1 d . . . . .
H00A H 0.646459 0.754895 -0.102401 0.031 Uiso 1 1 calc R U . . .
H00B H 0.597375 0.737946 0.022897 0.031 Uiso 1 1 calc R U . . .
C00H C 0.9787(2) 0.87851(18) 0.36819(17) 0.0283(4) Uani 1 1 d . . . . .
C00I C 0.4464(2) 0.10746(18) 0.56252(18) 0.0287(4) Uani 1 1 d . . . . .
C00J C 0.8445(2) 0.83282(17) 0.04584(16) 0.0238(4) Uani 1 1 d . . . . .
C00K C 0.8529(2) 0.61350(18) -0.05613(17) 0.0266(4) Uani 1 1 d . . . . .
H00K H 0.807467 0.633207 -0.126945 0.032 Uiso 1 1 calc R U . . .
C00L C 0.3438(2) 0.21880(18) 0.43995(17) 0.0260(4) Uani 1 1 d . . . . .
C00M C 0.8691(2) 0.48342(18) -0.08088(18) 0.0285(4) Uani 1 1 d . . . . .
C00N C 0.3875(2) 0.10421(18) 0.44093(18) 0.0277(4) Uani 1 1 d . . . . .
C00O C 0.5941(2) 0.9649(2) 0.10621(19) 0.0330(4) Uani 1 1 d . . . . .
H00C H 0.522416 0.881922 0.124572 0.040 Uiso 1 1 calc R U . . .
H00D H 0.531589 1.019345 0.089711 0.040 Uiso 1 1 calc R U . . .
C00P C 0.3933(2) 0.38191(18) 0.75766(17) 0.0255(4) Uani 1 1 d . . . . .
C00Q C 1.0587(2) 0.8540(2) 0.46796(18) 0.0324(4) Uani 1 1 d . . . . .
H00Q H 1.112347 0.795045 0.459501 0.039 Uiso 1 1 calc R U . . .
C00R C 0.8978(2) 0.96529(18) 0.37658(17) 0.0275(4) Uani 1 1 d . . . . .
C00S C 0.9726(2) 0.72179(19) 0.17261(17) 0.0290(4) Uani 1 1 d . . . . .
C00T C -0.0694(3) 0.4391(2) 0.4374(2) 0.0432(5) Uani 1 1 d . . . . .
C00U C 0.8322(2) 0.97072(18) 0.25456(17) 0.0258(4) Uani 1 1 d . . . . .
C00V C 0.2042(2) 0.40796(19) 0.57863(17) 0.0289(4) Uani 1 1 d . . . . .
H00E H 0.116645 0.320388 0.574350 0.035 Uiso 1 1 calc R U . . .
H00F H 0.189838 0.480489 0.632896 0.035 Uiso 1 1 calc R U . . .
C00W C 0.4422(2) 0.26499(18) 0.75435(17) 0.0275(4) Uani 1 1 d . . . . .
C00X C 0.3980(2) 0.46687(18) 0.98147(18) 0.0291(4) Uani 1 1 d . . . . .
C00Y C 0.3665(2) 0.40530(17) 0.62909(16) 0.0245(4) Uani 1 1 d . . . . .
C00Z C 0.5204(3) 0.4420(2) 1.04650(19) 0.0348(4) Uani 1 1 d . . . . .
H00Z H 0.576444 0.399449 1.004685 0.042 Uiso 1 1 calc R U . . .
C010 C 0.3662(2) 0.45554(19) 0.85025(18) 0.0287(4) Uani 1 1 d . . . . .
H010 H 0.315979 0.511958 0.825772 0.034 Uiso 1 1 calc R U . . .
C011 C 0.3686(3) 0.8329(2) -0.1345(2) 0.0390(5) Uani 1 1 d . . . . .
C012 C 0.5382(2) 0.9244(2) -0.11354(18) 0.0315(4) Uani 1 1 d . . . . .
H01A H 0.577572 0.898035 -0.184395 0.038 Uiso 1 1 calc R U . . .
H01B H 0.545273 1.017471 -0.109073 0.038 Uiso 1 1 calc R U . . .
C013 C 0.3773(3) -0.0019(2) 0.3489(2) 0.0356(4) Uani 1 1 d . . . . .
H013 H 0.338731 -0.006584 0.265994 0.043 Uiso 1 1 calc R U . . .
C014 C 0.8959(3) 1.0281(2) 0.49195(18) 0.0354(4) Uani 1 1 d . . . . .
H014 H 0.841048 1.085983 0.501246 0.042 Uiso 1 1 calc R U . . .
C015 C 0.8596(3) 0.4265(2) -0.2014(2) 0.0347(4) Uani 1 1 d . . . . .
H015 H 0.847925 0.474079 -0.261609 0.042 Uiso 1 1 calc R U . . .
C016 C 0.1392(3) 0.3079(2) 0.35816(18) 0.0338(4) Uani 1 1 d . . . . .
H01K H 0.092870 0.325708 0.282384 0.041 Uiso 1 1 calc R U . . .
H01M H 0.051383 0.236437 0.378092 0.041 Uiso 1 1 calc R U . . .
C017 C 0.7333(3) 1.0461(2) 0.21732(18) 0.0329(4) Uani 1 1 d . . . . .
H01C H 0.803373 1.130415 0.199835 0.040 Uiso 1 1 calc R U . . .
H01D H 0.690092 1.072107 0.285974 0.040 Uiso 1 1 calc R U . . .
C018 C 0.9758(3) 1.0041(2) 0.59238(19) 0.0396(5) Uani 1 1 d . . . . .
H018 H 0.975200 1.046361 0.671121 0.048 Uiso 1 1 calc R U . . .
C019 C 0.8820(3) 0.4091(2) 0.00518(19) 0.0346(4) Uani 1 1 d . . . . .
H019 H 0.888479 0.445434 0.087582 0.042 Uiso 1 1 calc R U . . .
C01A C 0.3127(3) 0.5245(2) 1.0461(2) 0.0378(5) Uani 1 1 d . . . . .
H01N H 0.228331 0.541612 1.002887 0.045 Uiso 1 1 calc R U . . .
C01B C 0.3496(3) 0.5565(2) 1.1707(2) 0.0473(6) Uani 1 1 d . . . . .
H01O H 0.288073 0.591992 1.213021 0.057 Uiso 1 1 calc R U . . .
C01C C 1.0568(3) 0.9198(2) 0.58094(18) 0.0369(5) Uani 1 1 d . . . . .
H01E H 1.111919 0.906957 0.651912 0.044 Uiso 1 1 calc R U . . .
C01D C 0.0997(3) 0.5101(2) 0.4356(2) 0.0395(5) Uani 1 1 d . . . . .
H01P H 0.103288 0.531866 0.355885 0.047 Uiso 1 1 calc R U . . .
H01Q H 0.147641 0.596691 0.498545 0.047 Uiso 1 1 calc R U . . .
C01E C 0.8853(3) 0.2835(2) -0.0291(2) 0.0413(5) Uani 1 1 d . . . . .
H01F H 0.892615 0.233531 0.029831 0.050 Uiso 1 1 calc R U . . .
C01F C 0.4759(4) 0.5370(2) 1.2342(2) 0.0522(7) Uani 1 1 d . . . . .
H01R H 0.504810 0.563225 1.320411 0.063 Uiso 1 1 calc R U . . .
C01G C 0.4247(3) -0.0996(2) 0.3819(2) 0.0437(5) Uani 1 1 d . . . . .
H01S H 0.418974 -0.171754 0.320289 0.052 Uiso 1 1 calc R U . . .
C01H C 0.5611(3) 0.4793(2) 1.1727(2) 0.0475(6) Uani 1 1 d . . . . .
H01T H 0.647375 0.465225 1.216802 0.057 Uiso 1 1 calc R U . . .
C21 C -0.2037(3) 0.3778(3) 0.4411(3) 0.0560(6) Uani 1 1 d . . . . .
H21 H -0.311174 0.328726 0.443983 0.067 Uiso 1 1 calc R U . . .
C01J C 0.8781(3) 0.2293(2) -0.1483(2) 0.0437(5) Uani 1 1 d . . . . .
H01J H 0.880779 0.142868 -0.170964 0.052 Uiso 1 1 calc R U . . .
C01K C 0.4929(3) 0.0089(2) 0.5960(2) 0.0385(5) Uani 1 1 d . . . . .
H01U H 0.531320 0.012546 0.678661 0.046 Uiso 1 1 calc R U . . .
C01L C 0.8671(3) 0.3017(2) -0.2342(2) 0.0429(5) Uani 1 1 d . . . . .
H01L H 0.864599 0.265992 -0.315745 0.051 Uiso 1 1 calc R U . . .
C01M C 0.2643(3) 0.2532(2) 0.33386(18) 0.0343(4) Uani 1 1 d . . . . .
H01V H 0.211854 0.170898 0.265924 0.041 Uiso 1 1 calc R U . . .
H01W H 0.347943 0.321538 0.307517 0.041 Uiso 1 1 calc R U . . .
C01N C 1.2049(3) 1.0989(2) -0.0029(2) 0.0463(6) Uani 1 1 d . . . . .
H01G H 1.227272 1.040740 -0.065379 0.070 Uiso 1 1 calc R U . . .
H01H H 1.304785 1.157161 0.058317 0.070 Uiso 1 1 calc R U . . .
H01I H 1.159579 1.155137 -0.040226 0.070 Uiso 1 1 calc R U . . .
C01O C 0.4807(3) -0.0951(2) 0.5029(2) 0.0445(5) Uani 1 1 d . . . . .
H01X H 0.511071 -0.164701 0.522012 0.053 Uiso 1 1 calc R U . . .
C01P C 0.7443(3) 0.6610(2) 0.5916(2) 0.0430(5) Uani 1 1 d . . . . .
H01Y H 0.702583 0.704416 0.534684 0.065 Uiso 1 1 calc R U . . .
H H 0.833238 0.643950 0.567439 0.065 Uiso 1 1 calc R U . . .
HA H 0.782538 0.720743 0.673572 0.065 Uiso 1 1 calc R U . . .
C20 C 0.2322(3) 0.7619(3) -0.1481(3) 0.0605(7) Uani 1 1 d . . . . .
H20 H 0.122511 0.704856 -0.158972 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00C 1.326(2) . ?
O001 C01N 1.455(2) . ?
O002 C00B 1.324(2) . ?
O002 C01P 1.457(2) . ?
O003 C00C 1.199(2) . ?
O004 C00B 1.194(2) . ?
O005 C00W 1.209(2) . ?
O006 C00S 1.210(2) . ?
N007 C00D 1.393(2) . ?
N007 C00I 1.395(2) . ?
N007 C00W 1.393(2) . ?
N008 C00E 1.393(2) . ?
N008 C00H 1.403(2) . ?
N008 C00S 1.382(2) . ?
N009 C00G 1.470(2) . ?
N009 C00O 1.474(2) . ?
N009 C012 1.464(3) . ?
N00A C00V 1.474(2) . ?
N00A C016 1.479(3) . ?
N00A C01D 1.471(3) . ?
C00B C00Y 1.543(2) . ?
C00C C00J 1.540(2) . ?
C00D C00L 1.347(3) . ?
C00D C00Y 1.490(2) . ?
C00E C00J 1.498(2) . ?
C00E C00U 1.349(3) . ?
C00F C00J 1.542(2) . ?
C00F C00K 1.344(3) . ?
C00F C00S 1.501(3) . ?
C00G H00A 0.9900 . ?
C00G H00B 0.9900 . ?
C00G C00J 1.529(3) . ?
C00H C00Q 1.383(3) . ?
C00H C00R 1.410(3) . ?
C00I C00N 1.408(3) . ?
C00I C01K 1.387(3) . ?
C00K H00K 0.9500 . ?
C00K C00M 1.473(3) . ?
C00L C00N 1.454(3) . ?
C00L C01M 1.497(3) . ?
C00M C015 1.400(3) . ?
C00M C019 1.401(3) . ?
C00N C013 1.401(3) . ?
C00O H00C 0.9900 . ?
C00O H00D 0.9900 . ?
C00O C017 1.525(3) . ?
C00P C00W 1.504(3) . ?
C00P C00Y 1.542(2) . ?
C00P C010 1.343(3) . ?
C00Q H00Q 0.9500 . ?
C00Q C01C 1.386(3) . ?
C00R C00U 1.458(3) . ?
C00R C014 1.398(3) . ?
C00T C01D 1.475(3) . ?
C00T C21 1.187(4) . ?
C00U C017 1.499(3) . ?
C00V H00E 0.9900 . ?
C00V H00F 0.9900 . ?
C00V C00Y 1.530(3) . ?
C00X C00Z 1.391(3) . ?
C00X C010 1.468(3) . ?
C00X C01A 1.406(3) . ?
C00Z H00Z 0.9500 . ?
C00Z C01H 1.391(3) . ?
C010 H010 0.9500 . ?
C011 C012 1.471(3) . ?
C011 C20 1.180(4) . ?
C012 H01A 0.9900 . ?
C012 H01B 0.9900 . ?
C013 H013 0.9500 . ?
C013 C01G 1.380(3) . ?
C014 H014 0.9500 . ?
C014 C018 1.385(3) . ?
C015 H015 0.9500 . ?
C015 C01L 1.386(3) . ?
C016 H01K 0.9900 . ?
C016 H01M 0.9900 . ?
C016 C01M 1.528(3) . ?
C017 H01C 0.9900 . ?
C017 H01D 0.9900 . ?
C018 H018 0.9500 . ?
C018 C01C 1.390(3) . ?
C019 H019 0.9500 . ?
C019 C01E 1.381(3) . ?
C01A H01N 0.9500 . ?
C01A C01B 1.374(3) . ?
C01B H01O 0.9500 . ?
C01B C01F 1.379(4) . ?
C01C H01E 0.9500 . ?
C01D H01P 0.9900 . ?
C01D H01Q 0.9900 . ?
C01E H01F 0.9500 . ?
C01E C01J 1.384(3) . ?
C01F H01R 0.9500 . ?
C01F C01H 1.387(4) . ?
C01G H01S 0.9500 . ?
C01G C01O 1.392(4) . ?
C01H H01T 0.9500 . ?
C21 H21 0.9500 . ?
C01J H01J 0.9500 . ?
C01J C01L 1.382(4) . ?
C01K H01U 0.9500 . ?
C01K C01O 1.386(3) . ?
C01L H01L 0.9500 . ?
C01M H01V 0.9900 . ?
C01M H01W 0.9900 . ?
C01N H01G 0.9800 . ?
C01N H01H 0.9800 . ?
C01N H01I 0.9800 . ?
C01O H01X 0.9500 . ?
C01P H01Y 0.9800 . ?
C01P H 0.9800 . ?
C01P HA 0.9800 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C O001 C01N 115.64(16) . . ?
C00B O002 C01P 115.26(16) . . ?
C00D N007 C00I 108.17(15) . . ?
C00D N007 C00W 113.20(15) . . ?
C00W N007 C00I 135.91(16) . . ?
C00E N008 C00H 108.70(15) . . ?
C00S N008 C00E 113.62(15) . . ?
C00S N008 C00H 135.28(16) . . ?
C00G N009 C00O 114.67(15) . . ?
C012 N009 C00G 111.78(15) . . ?
C012 N009 C00O 111.73(15) . . ?
C00V N00A C016 113.74(14) . . ?
C01D N00A C00V 109.63(16) . . ?
C01D N00A C016 110.59(17) . . ?
O002 C00B C00Y 112.68(15) . . ?
O004 C00B O002 124.20(17) . . ?
O004 C00B C00Y 123.09(17) . . ?
O001 C00C C00J 112.74(15) . . ?
O003 C00C O001 124.20(17) . . ?
O003 C00C C00J 122.96(17) . . ?
N007 C00D C00Y 110.32(15) . . ?
C00L C00D N007 111.22(16) . . ?
C00L C00D C00Y 138.12(17) . . ?
N008 C00E C00J 109.84(15) . . ?
C00U C00E N008 111.14(16) . . ?
C00U C00E C00J 138.47(18) . . ?
C00K C00F C00J 122.07(17) . . ?
C00K C00F C00S 129.43(17) . . ?
C00S C00F C00J 108.49(15) . . ?
N009 C00G H00A 109.7 . . ?
N009 C00G H00B 109.7 . . ?
N009 C00G C00J 109.66(14) . . ?
H00A C00G H00B 108.2 . . ?
C00J C00G H00A 109.7 . . ?
C00J C00G H00B 109.7 . . ?
N008 C00H C00R 105.87(16) . . ?
C00Q C00H N008 130.56(19) . . ?
C00Q C00H C00R 123.54(18) . . ?
N007 C00I C00N 106.73(16) . . ?
C01K C00I N007 130.3(2) . . ?
C01K C00I C00N 122.98(19) . . ?
C00C C00J C00F 107.53(13) . . ?
C00E C00J C00C 114.80(15) . . ?
C00E C00J C00F 100.98(14) . . ?
C00E C00J C00G 109.68(15) . . ?
C00G C00J C00C 108.04(15) . . ?
C00G C00J C00F 115.92(14) . . ?
C00F C00K H00K 113.3 . . ?
C00F C00K C00M 133.48(18) . . ?
C00M C00K H00K 113.3 . . ?
C00D C00L C00N 105.72(16) . . ?
C00D C00L C01M 125.81(17) . . ?
C00N C00L C01M 128.40(17) . . ?
C015 C00M C00K 116.82(17) . . ?
C015 C00M C019 118.17(18) . . ?
C019 C00M C00K 124.85(17) . . ?
C00I C00N C00L 108.09(16) . . ?
C013 C00N C00I 118.86(18) . . ?
C013 C00N C00L 133.02(19) . . ?
N009 C00O H00C 108.8 . . ?
N009 C00O H00D 108.8 . . ?
N009 C00O C017 113.72(16) . . ?
H00C C00O H00D 107.7 . . ?
C017 C00O H00C 108.8 . . ?
C017 C00O H00D 108.8 . . ?
C00W C00P C00Y 108.85(15) . . ?
C010 C00P C00W 129.60(17) . . ?
C010 C00P C00Y 121.46(16) . . ?
C00H C00Q H00Q 121.7 . . ?
C00H C00Q C01C 116.7(2) . . ?
C01C C00Q H00Q 121.7 . . ?
C00H C00R C00U 108.73(16) . . ?
C014 C00R C00H 118.26(19) . . ?
C014 C00R C00U 133.01(19) . . ?
O006 C00S N008 124.50(18) . . ?
O006 C00S C00F 130.06(18) . . ?
N008 C00S C00F 105.44(15) . . ?
C21 C00T C01D 177.0(3) . . ?
C00E C00U C00R 105.53(16) . . ?
C00E C00U C017 126.15(17) . . ?
C00R C00U C017 128.32(16) . . ?
N00A C00V H00E 109.8 . . ?
N00A C00V H00F 109.8 . . ?
N00A C00V C00Y 109.26(15) . . ?
H00E C00V H00F 108.3 . . ?
C00Y C00V H00E 109.8 . . ?
C00Y C00V H00F 109.8 . . ?
O005 C00W N007 124.86(17) . . ?
O005 C00W C00P 129.99(18) . . ?
N007 C00W C00P 105.06(15) . . ?
C00Z C00X C010 124.15(17) . . ?
C00Z C00X C01A 118.52(19) . . ?
C01A C00X C010 116.72(19) . . ?
C00D C00Y C00B 114.22(14) . . ?
C00D C00Y C00P 101.30(14) . . ?
C00D C00Y C00V 110.83(15) . . ?
C00P C00Y C00B 108.32(15) . . ?
C00V C00Y C00B 106.55(14) . . ?
C00V C00Y C00P 115.83(15) . . ?
C00X C00Z H00Z 120.0 . . ?
C00X C00Z C01H 120.1(2) . . ?
C01H C00Z H00Z 120.0 . . ?
C00P C010 C00X 133.28(19) . . ?
C00P C010 H010 113.4 . . ?
C00X C010 H010 113.4 . . ?
C20 C011 C012 177.9(3) . . ?
N009 C012 C011 115.22(17) . . ?
N009 C012 H01A 108.5 . . ?
N009 C012 H01B 108.5 . . ?
C011 C012 H01A 108.5 . . ?
C011 C012 H01B 108.5 . . ?
H01A C012 H01B 107.5 . . ?
C00N C013 H013 120.8 . . ?
C01G C013 C00N 118.3(2) . . ?
C01G C013 H013 120.8 . . ?
C00R C014 H014 120.7 . . ?
C018 C014 C00R 118.6(2) . . ?
C018 C014 H014 120.7 . . ?
C00M C015 H015 119.5 . . ?
C01L C015 C00M 120.9(2) . . ?
C01L C015 H015 119.5 . . ?
N00A C016 H01K 108.3 . . ?
N00A C016 H01M 108.3 . . ?
N00A C016 C01M 115.81(17) . . ?
H01K C016 H01M 107.4 . . ?
C01M C016 H01K 108.3 . . ?
C01M C016 H01M 108.3 . . ?
C00O C017 H01C 108.9 . . ?
C00O C017 H01D 108.9 . . ?
C00U C017 C00O 113.54(16) . . ?
C00U C017 H01C 108.9 . . ?
C00U C017 H01D 108.9 . . ?
H01C C017 H01D 107.7 . . ?
C014 C018 H018 119.1 . . ?
C014 C018 C01C 121.71(19) . . ?
C01C C018 H018 119.1 . . ?
C00M C019 H019 119.8 . . ?
C01E C019 C00M 120.35(19) . . ?
C01E C019 H019 119.8 . . ?
C00X C01A H01N 119.5 . . ?
C01B C01A C00X 121.1(2) . . ?
C01B C01A H01N 119.5 . . ?
C01A C01B H01O 120.1 . . ?
C01A C01B C01F 119.8(2) . . ?
C01F C01B H01O 120.1 . . ?
C00Q C01C C018 121.3(2) . . ?
C00Q C01C H01E 119.4 . . ?
C018 C01C H01E 119.4 . . ?
N00A C01D C00T 114.19(18) . . ?
N00A C01D H01P 108.7 . . ?
N00A C01D H01Q 108.7 . . ?
C00T C01D H01P 108.7 . . ?
C00T C01D H01Q 108.7 . . ?
H01P C01D H01Q 107.6 . . ?
C019 C01E H01F 119.6 . . ?
C019 C01E C01J 120.9(2) . . ?
C01J C01E H01F 119.6 . . ?
C01B C01F H01R 119.9 . . ?
C01B C01F C01H 120.2(2) . . ?
C01H C01F H01R 119.9 . . ?
C013 C01G H01S 119.1 . . ?
C013 C01G C01O 121.8(2) . . ?
C01O C01G H01S 119.1 . . ?
C00Z C01H H01T 119.9 . . ?
C01F C01H C00Z 120.2(2) . . ?
C01F C01H H01T 119.9 . . ?
C00T C21 H21 180.0 . . ?
C01E C01J H01J 120.2 . . ?
C01L C01J C01E 119.59(19) . . ?
C01L C01J H01J 120.2 . . ?
C00I C01K H01U 121.6 . . ?
C01O C01K C00I 116.8(2) . . ?
C01O C01K H01U 121.6 . . ?
C015 C01L H01L 120.0 . . ?
C01J C01L C015 120.1(2) . . ?
C01J C01L H01L 120.0 . . ?
C00L C01M C016 114.81(16) . . ?
C00L C01M H01V 108.6 . . ?
C00L C01M H01W 108.6 . . ?
C016 C01M H01V 108.6 . . ?
C016 C01M H01W 108.6 . . ?
H01V C01M H01W 107.5 . . ?
O001 C01N H01G 109.5 . . ?
O001 C01N H01H 109.5 . . ?
O001 C01N H01I 109.5 . . ?
H01G C01N H01H 109.5 . . ?
H01G C01N H01I 109.5 . . ?
H01H C01N H01I 109.5 . . ?
C01G C01O H01X 119.3 . . ?
C01K C01O C01G 121.3(2) . . ?
C01K C01O H01X 119.3 . . ?
O002 C01P H01Y 109.5 . . ?
O002 C01P H 109.5 . . ?
O002 C01P HA 109.5 . . ?
H01Y C01P H 109.5 . . ?
H01Y C01P HA 109.5 . . ?
H C01P HA 109.5 . . ?
C011 C20 H20 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C00C C00J C00E 22.9(2) . . . . ?
O001 C00C C00J C00F -88.56(18) . . . . ?
O001 C00C C00J C00G 145.64(16) . . . . ?
O002 C00B C00Y C00D -13.1(2) . . . . ?
O002 C00B C00Y C00P 98.91(18) . . . . ?
O002 C00B C00Y C00V -135.84(16) . . . . ?
O003 C00C C00J C00E -160.56(18) . . . . ?
O003 C00C C00J C00F 88.0(2) . . . . ?
O003 C00C C00J C00G -37.8(2) . . . . ?
O004 C00B C00Y C00D 168.92(18) . . . . ?
O004 C00B C00Y C00P -79.0(2) . . . . ?
O004 C00B C00Y C00V 46.2(2) . . . . ?
N007 C00D C00L C00N -2.4(2) . . . . ?
N007 C00D C00L C01M 174.92(17) . . . . ?
N007 C00D C00Y C00B 105.38(17) . . . . ?
N007 C00D C00Y C00P -10.81(18) . . . . ?
N007 C00D C00Y C00V -134.27(16) . . . . ?
N007 C00I C00N C00L -1.4(2) . . . . ?
N007 C00I C00N C013 -179.80(17) . . . . ?
N007 C00I C01K C01O 179.2(2) . . . . ?
N008 C00E C00J C00C -102.73(17) . . . . ?
N008 C00E C00J C00F 12.59(18) . . . . ?
N008 C00E C00J C00G 135.43(15) . . . . ?
N008 C00E C00U C00R 1.6(2) . . . . ?
N008 C00E C00U C017 -177.31(17) . . . . ?
N008 C00H C00Q C01C 178.13(19) . . . . ?
N008 C00H C00R C00U -0.37(19) . . . . ?
N008 C00H C00R C014 -179.65(16) . . . . ?
N009 C00G C00J C00C -61.60(18) . . . . ?
N009 C00G C00J C00E 64.20(18) . . . . ?
N009 C00G C00J C00F 177.71(14) . . . . ?
N009 C00O C017 C00U -61.3(2) . . . . ?
N00A C00V C00Y C00B 58.81(18) . . . . ?
N00A C00V C00Y C00D -66.01(19) . . . . ?
N00A C00V C00Y C00P 179.35(14) . . . . ?
N00A C016 C01M C00L 59.1(2) . . . . ?
C00D N007 C00I C00N 0.0(2) . . . . ?
C00D N007 C00I C01K -178.7(2) . . . . ?
C00D N007 C00W O005 170.04(18) . . . . ?
C00D N007 C00W C00P -6.8(2) . . . . ?
C00D C00L C00N C00I 2.4(2) . . . . ?
C00D C00L C00N C013 -179.6(2) . . . . ?
C00D C00L C01M C016 -36.4(3) . . . . ?
C00E N008 C00H C00Q -176.96(19) . . . . ?
C00E N008 C00H C00R 1.34(19) . . . . ?
C00E N008 C00S O006 -178.59(19) . . . . ?
C00E N008 C00S C00F 2.0(2) . . . . ?
C00E C00U C017 C00O 40.7(3) . . . . ?
C00F C00K C00M C015 -163.0(2) . . . . ?
C00F C00K C00M C019 21.7(3) . . . . ?
C00G N009 C00O C017 85.4(2) . . . . ?
C00G N009 C012 C011 71.6(2) . . . . ?
C00H N008 C00E C00J -175.07(14) . . . . ?
C00H N008 C00E C00U -1.9(2) . . . . ?
C00H N008 C00S O006 -18.7(3) . . . . ?
C00H N008 C00S C00F 161.85(19) . . . . ?
C00H C00Q C01C C018 1.1(3) . . . . ?
C00H C00R C00U C00E -0.8(2) . . . . ?
C00H C00R C00U C017 178.14(18) . . . . ?
C00H C00R C014 C018 1.1(3) . . . . ?
C00I N007 C00D C00L 1.6(2) . . . . ?
C00I N007 C00D C00Y 176.18(14) . . . . ?
C00I N007 C00W O005 11.6(3) . . . . ?
C00I N007 C00W C00P -165.2(2) . . . . ?
C00I C00N C013 C01G 0.4(3) . . . . ?
C00I C01K C01O C01G 0.2(3) . . . . ?
C00J C00E C00U C00R 171.9(2) . . . . ?
C00J C00E C00U C017 -7.1(4) . . . . ?
C00J C00F C00K C00M -174.54(18) . . . . ?
C00J C00F C00S O006 -173.0(2) . . . . ?
C00J C00F C00S N008 6.38(19) . . . . ?
C00K C00F C00J C00C -71.0(2) . . . . ?
C00K C00F C00J C00E 168.37(17) . . . . ?
C00K C00F C00J C00G 50.0(2) . . . . ?
C00K C00F C00S O006 7.3(3) . . . . ?
C00K C00F C00S N008 -173.29(18) . . . . ?
C00K C00M C015 C01L -177.39(19) . . . . ?
C00K C00M C019 C01E 175.4(2) . . . . ?
C00L C00D C00Y C00B -82.2(3) . . . . ?
C00L C00D C00Y C00P 161.6(2) . . . . ?
C00L C00D C00Y C00V 38.2(3) . . . . ?
C00L C00N C013 C01G -177.4(2) . . . . ?
C00M C015 C01L C01J 2.4(3) . . . . ?
C00M C019 C01E C01J 0.8(3) . . . . ?
C00N C00I C01K C01O 0.7(3) . . . . ?
C00N C00L C01M C016 140.38(19) . . . . ?
C00N C013 C01G C01O 0.4(3) . . . . ?
C00O N009 C00G C00J -89.59(18) . . . . ?
C00O N009 C012 C011 -58.4(2) . . . . ?
C00Q C00H C00R C00U 178.09(17) . . . . ?
C00Q C00H C00R C014 -1.2(3) . . . . ?
C00R C00H C00Q C01C 0.1(3) . . . . ?
C00R C00U C017 C00O -137.98(19) . . . . ?
C00R C014 C018 C01C 0.0(3) . . . . ?
C00S N008 C00E C00J -9.9(2) . . . . ?
C00S N008 C00E C00U 163.27(16) . . . . ?
C00S N008 C00H C00Q 22.5(3) . . . . ?
C00S N008 C00H C00R -159.2(2) . . . . ?
C00S C00F C00J C00C 109.30(16) . . . . ?
C00S C00F C00J C00E -11.33(18) . . . . ?
C00S C00F C00J C00G -129.74(16) . . . . ?
C00S C00F C00K C00M 5.1(3) . . . . ?
C00U C00E C00J C00C 86.9(3) . . . . ?
C00U C00E C00J C00F -157.7(2) . . . . ?
C00U C00E C00J C00G -34.9(3) . . . . ?
C00U C00R C014 C018 -177.9(2) . . . . ?
C00V N00A C016 C01M -83.2(2) . . . . ?
C00V N00A C01D C00T -62.7(2) . . . . ?
C00W N007 C00D C00L -162.77(16) . . . . ?
C00W N007 C00D C00Y 11.8(2) . . . . ?
C00W N007 C00I C00N 159.14(19) . . . . ?
C00W N007 C00I C01K -19.6(4) . . . . ?
C00W C00P C00Y C00B -113.77(16) . . . . ?
C00W C00P C00Y C00D 6.68(18) . . . . ?
C00W C00P C00Y C00V 126.65(17) . . . . ?
C00W C00P C010 C00X 11.9(4) . . . . ?
C00X C00Z C01H C01F 2.3(3) . . . . ?
C00X C01A C01B C01F 2.6(3) . . . . ?
C00Y C00D C00L C00N -174.8(2) . . . . ?
C00Y C00D C00L C01M 2.5(4) . . . . ?
C00Y C00P C00W O005 -177.1(2) . . . . ?
C00Y C00P C00W N007 -0.48(19) . . . . ?
C00Y C00P C010 C00X -171.73(19) . . . . ?
C00Z C00X C010 C00P 26.9(3) . . . . ?
C00Z C00X C01A C01B 0.4(3) . . . . ?
C010 C00P C00W O005 -0.4(3) . . . . ?
C010 C00P C00W N007 176.22(19) . . . . ?
C010 C00P C00Y C00B 69.2(2) . . . . ?
C010 C00P C00Y C00D -170.33(17) . . . . ?
C010 C00P C00Y C00V -50.4(2) . . . . ?
C010 C00X C00Z C01H 167.90(19) . . . . ?
C010 C00X C01A C01B -171.01(19) . . . . ?
C012 N009 C00G C00J 141.93(16) . . . . ?
C012 N009 C00O C017 -146.08(17) . . . . ?
C013 C01G C01O C01K -0.7(4) . . . . ?
C014 C00R C00U C00E 178.4(2) . . . . ?
C014 C00R C00U C017 -2.7(3) . . . . ?
C014 C018 C01C C00Q -1.1(3) . . . . ?
C015 C00M C019 C01E 0.1(3) . . . . ?
C016 N00A C00V C00Y 87.90(19) . . . . ?
C016 N00A C01D C00T 63.5(2) . . . . ?
C019 C00M C015 C01L -1.7(3) . . . . ?
C019 C01E C01J C01L -0.2(4) . . . . ?
C01A C00X C00Z C01H -2.8(3) . . . . ?
C01A C00X C010 C00P -162.2(2) . . . . ?
C01A C01B C01F C01H -3.1(4) . . . . ?
C01B C01F C01H C00Z 0.6(4) . . . . ?
C01D N00A C00V C00Y -147.72(16) . . . . ?
C01D N00A C016 C01M 152.93(17) . . . . ?
C01E C01J C01L C015 -1.4(4) . . . . ?
C01K C00I C00N C00L 177.38(18) . . . . ?
C01K C00I C00N C013 -1.0(3) . . . . ?
C01M C00L C00N C00I -174.89(18) . . . . ?
C01M C00L C00N C013 3.2(3) . . . . ?
C01N O001 C00C O003 -1.0(3) . . . . ?
C01N O001 C00C C00J 175.53(17) . . . . ?
C01P O002 C00B O004 -1.3(3) . . . . ?
C01P O002 C00B C00Y -179.25(17) . . . . ?

_olex2_exptl_crystal_mounting_method 'manual mounting'
_olex2_submission_original_sample_id 240916wayamakaneko
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_241125wayamakaneko_3b2b27797e8dbfef_a
_database_code_depnum_ccdc_archive 'CCDC 2466313'
loop_
_audit_author_name
_audit_author_address
'Toshiaki Wayama'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2024-11-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
toshiakiw@g.ecc.u-tokyo.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        241125WayamaKAneko
_chemical_formula_moiety         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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                   11.146(5)
_cell_length_b                   11.436(6)
_cell_length_c                   12.862(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.204(13)
_cell_angle_gamma                90
_cell_volume                     1635.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    554
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      17.46
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8855
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1094 before and 0.0857 after correction.
The Ratio of minimum to maximum transmission is 0.8855.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_lustre     translucent
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_preparation       'slow evapolation from acetone'
_exptl_crystal_recrystallization_method 'slow evapolation from acetone'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1346
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49044
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_min         1.832
_diffrn_ambient_temperature      300.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1866
_reflns_number_total             4028
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.037
_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)+(0.0974P)²+1.0374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.2506
_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:
 C6(H6A,H6B), C7(H7A,H7B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O 0.0106(3) 0.3876(3) 0.6809(2) 0.0936(9) Uani 1 1 d . . . . .
O2 O 0.3432(3) 0.7005(2) 0.4339(2) 0.0847(9) Uani 1 1 d . . . . .
O1 O 0.0654(2) 0.2498(2) 0.5735(2) 0.0774(8) Uani 1 1 d . . . . .
N2 N 0.3212(3) 0.0989(2) 0.4689(2) 0.0596(7) Uani 1 1 d . . . . .
C3 C 0.1930(4) -0.0552(4) 0.6725(4) 0.0903(13) Uani 1 1 d . . . . .
N4 N 0.3037(2) 0.5053(2) 0.45523(18) 0.0525(6) Uani 1 1 d . . . . .
C1 C -0.0178(4) 0.1708(4) 0.6192(4) 0.0952(14) Uani 1 1 d . . . . .
H1A H -0.096583 0.205192 0.615401 0.143 Uiso 1 1 calc R U . . .
H1B H 0.008615 0.156625 0.690828 0.143 Uiso 1 1 calc R U . . .
H1C H -0.020617 0.098152 0.581662 0.143 Uiso 1 1 calc R U . . .
C20 C 0.0707(3) 0.3579(3) 0.6118(3) 0.0632(9) Uani 1 1 d . . . . .
C2 C 0.1526(3) 0.4390(3) 0.5626(2) 0.0560(8) Uani 1 1 d . . . . .
C4 C 0.2396(3) 0.4135(2) 0.4950(2) 0.0510(7) Uani 1 1 d . . . . .
C5 C 0.2853(3) 0.2993(2) 0.4512(2) 0.0523(7) Uani 1 1 d . . . . .
C6 C 0.3314(3) 0.2067(2) 0.5316(2) 0.0571(8) Uani 1 1 d . . . . .
H6A H 0.414026 0.221780 0.557077 0.068 Uiso 1 1 calc R U . . .
H6B H 0.281359 0.203367 0.590159 0.068 Uiso 1 1 calc R U . . .
C7 C 0.3455(3) -0.0083(3) 0.5298(3) 0.0714(10) Uani 1 1 d . . . . .
H7A H 0.425713 -0.002634 0.564183 0.086 Uiso 1 1 calc R U . . .
H7B H 0.345339 -0.073825 0.481917 0.086 Uiso 1 1 calc R U . . .
C8 C 0.2606(3) -0.0338(3) 0.6091(3) 0.0730(10) Uani 1 1 d . . . . .
C9 C 0.2864(3) 0.6250(3) 0.4770(3) 0.0636(9) Uani 1 1 d . . . . .
C10 C 0.1993(3) 0.6458(3) 0.5509(3) 0.0687(9) Uani 1 1 d . . . . .
H10 H 0.185552 0.721989 0.572236 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1371(3) 0.5586(3) 0.5901(3) 0.0653(9) Uani 1 1 d . . . . .
H11 H 0.080947 0.576628 0.637613 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3933(3) 0.4624(2) 0.3913(2) 0.0517(7) Uani 1 1 d . . . . .
C13 C 0.3861(3) 0.3418(3) 0.3880(2) 0.0529(7) Uani 1 1 d . . . . .
C14 C 0.4645(3) 0.2788(3) 0.3319(2) 0.0631(9) Uani 1 1 d . . . . .
H14 H 0.460586 0.197601 0.329857 0.076 Uiso 1 1 calc R U . . .
C15 C 0.5492(3) 0.3381(3) 0.2785(3) 0.0680(9) Uani 1 1 d . . . . .
H15 H 0.602668 0.296661 0.240360 0.082 Uiso 1 1 calc R U . . .
C16 C 0.5544(3) 0.4584(3) 0.2818(3) 0.0668(9) Uani 1 1 d . . . . .
H16 H 0.611169 0.496950 0.244875 0.080 Uiso 1 1 calc R U . . .
C17 C 0.4775(3) 0.5236(3) 0.3386(2) 0.0626(9) Uani 1 1 d . . . . .
H17 H 0.482057 0.604782 0.341384 0.075 Uiso 1 1 calc R U . . .
C18 C 0.2045(3) 0.1031(3) 0.4116(3) 0.0685(10) Uani 1 1 d . . . . .
H18A H 0.141498 0.079539 0.455434 0.082 Uiso 1 1 calc R U . . .
H18B H 0.202381 0.052346 0.351085 0.082 Uiso 1 1 calc R U . . .
C19 C 0.1895(3) 0.2306(3) 0.3790(3) 0.0663(9) Uani 1 1 d . . . . .
H19A H 0.108838 0.257865 0.389450 0.080 Uiso 1 1 calc R U . . .
H19B H 0.204465 0.240462 0.306211 0.080 Uiso 1 1 calc R U . . .
H3 H 0.138(4) -0.075(4) 0.728(4) 0.125(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C20 1.200(4) . ?
O2 C9 1.227(4) . ?
O1 C1 1.450(4) . ?
O1 C20 1.330(4) . ?
N2 C6 1.473(4) . ?
N2 C7 1.469(4) . ?
N2 C18 1.449(5) . ?
C3 C8 1.174(5) . ?
C3 H3 1.01(5) . ?
N4 C4 1.388(4) . ?
N4 C9 1.413(4) . ?
N4 C12 1.427(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C20 C2 1.476(4) . ?
C2 C4 1.380(4) . ?
C2 C11 1.426(4) . ?
C4 C5 1.526(4) . ?
C5 C6 1.541(4) . ?
C5 C13 1.514(4) . ?
C5 C19 1.573(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.471(4) . ?
C9 C10 1.427(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.334(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 C17 1.386(4) . ?
C13 C14 1.377(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.523(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 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
C20 O1 C1 116.2(3) . . ?
C7 N2 C6 113.8(3) . . ?
C18 N2 C6 106.3(2) . . ?
C18 N2 C7 115.0(3) . . ?
C8 C3 H3 178(3) . . ?
C4 N4 C9 125.3(3) . . ?
C4 N4 C12 110.7(2) . . ?
C9 N4 C12 124.0(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C20 O1 121.7(3) . . ?
O3 C20 C2 122.4(3) . . ?
O1 C20 C2 115.9(3) . . ?
C4 C2 C20 128.5(3) . . ?
C4 C2 C11 117.5(3) . . ?
C11 C2 C20 114.0(3) . . ?
N4 C4 C5 108.5(2) . . ?
C2 C4 N4 118.5(3) . . ?
C2 C4 C5 133.0(3) . . ?
C4 C5 C6 116.4(2) . . ?
C4 C5 C19 114.5(3) . . ?
C6 C5 C19 103.4(2) . . ?
C13 C5 C4 101.8(2) . . ?
C13 C5 C6 110.9(2) . . ?
C13 C5 C19 110.0(2) . . ?
N2 C6 C5 101.5(3) . . ?
N2 C6 H6A 111.5 . . ?
N2 C6 H6B 111.5 . . ?
C5 C6 H6A 111.5 . . ?
C5 C6 H6B 111.5 . . ?
H6A C6 H6B 109.3 . . ?
N2 C7 H7A 108.4 . . ?
N2 C7 H7B 108.4 . . ?
N2 C7 C8 115.6(3) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C3 C8 C7 179.4(4) . . ?
O2 C9 N4 120.6(3) . . ?
O2 C9 C10 125.6(3) . . ?
N4 C9 C10 113.7(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C2 C11 H11 118.4 . . ?
C10 C11 C2 123.2(3) . . ?
C10 C11 H11 118.4 . . ?
C13 C12 N4 108.6(2) . . ?
C13 C12 C17 122.0(3) . . ?
C17 C12 N4 129.4(3) . . ?
C12 C13 C5 110.4(2) . . ?
C14 C13 C5 129.6(3) . . ?
C14 C13 C12 120.0(3) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.9(3) . . ?
C17 C16 H16 119.1 . . ?
C12 C17 H17 121.5 . . ?
C16 C17 C12 116.9(3) . . ?
C16 C17 H17 121.5 . . ?
N2 C18 H18A 110.9 . . ?
N2 C18 H18B 110.9 . . ?
N2 C18 C19 104.4(3) . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 H18A 110.9 . . ?
C19 C18 H18B 110.9 . . ?
C5 C19 H19A 110.7 . . ?
C5 C19 H19B 110.7 . . ?
C18 C19 C5 105.0(3) . . ?
C18 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C20 C2 C4 168.9(4) . . . . ?
O3 C20 C2 C11 -11.2(5) . . . . ?
O2 C9 C10 C11 176.5(4) . . . . ?
O1 C20 C2 C4 -12.4(5) . . . . ?
O1 C20 C2 C11 167.5(3) . . . . ?
N2 C18 C19 C5 -17.1(3) . . . . ?
N4 C4 C5 C6 123.6(3) . . . . ?
N4 C4 C5 C13 3.0(3) . . . . ?
N4 C4 C5 C19 -115.7(3) . . . . ?
N4 C9 C10 C11 -3.3(5) . . . . ?
N4 C12 C13 C5 1.0(4) . . . . ?
N4 C12 C13 C14 -179.3(3) . . . . ?
N4 C12 C17 C16 179.9(3) . . . . ?
C1 O1 C20 O3 0.7(5) . . . . ?
C1 O1 C20 C2 -178.1(3) . . . . ?
C20 C2 C4 N4 177.7(3) . . . . ?
C20 C2 C4 C5 -2.7(6) . . . . ?
C20 C2 C11 C10 -177.5(3) . . . . ?
C2 C4 C5 C6 -56.0(5) . . . . ?
C2 C4 C5 C13 -176.7(3) . . . . ?
C2 C4 C5 C19 64.7(4) . . . . ?
C4 N4 C9 O2 -176.2(3) . . . . ?
C4 N4 C9 C10 3.6(5) . . . . ?
C4 N4 C12 C13 1.0(4) . . . . ?
C4 N4 C12 C17 -178.7(3) . . . . ?
C4 C2 C11 C10 2.4(5) . . . . ?
C4 C5 C6 N2 158.4(2) . . . . ?
C4 C5 C13 C12 -2.4(3) . . . . ?
C4 C5 C13 C14 178.0(3) . . . . ?
C4 C5 C19 C18 -137.1(3) . . . . ?
C5 C13 C14 C15 179.1(3) . . . . ?
C6 N2 C7 C8 64.1(4) . . . . ?
C6 N2 C18 C19 39.4(3) . . . . ?
C6 C5 C13 C12 -126.9(3) . . . . ?
C6 C5 C13 C14 53.5(4) . . . . ?
C6 C5 C19 C18 -9.5(3) . . . . ?
C7 N2 C6 C5 -172.8(2) . . . . ?
C7 N2 C18 C19 166.3(3) . . . . ?
C9 N4 C4 C2 -0.9(5) . . . . ?
C9 N4 C4 C5 179.4(3) . . . . ?
C9 N4 C12 C13 179.1(3) . . . . ?
C9 N4 C12 C17 -0.6(5) . . . . ?
C9 C10 C11 C2 0.4(6) . . . . ?
C11 C2 C4 N4 -2.2(5) . . . . ?
C11 C2 C4 C5 177.5(3) . . . . ?
C12 N4 C4 C2 177.1(3) . . . . ?
C12 N4 C4 C5 -2.6(3) . . . . ?
C12 N4 C9 O2 6.0(5) . . . . ?
C12 N4 C9 C10 -174.2(3) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C5 C6 N2 -85.9(3) . . . . ?
C13 C5 C19 C18 109.0(3) . . . . ?
C13 C12 C17 C16 0.3(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C12 -0.9(5) . . . . ?
C17 C12 C13 C5 -179.3(3) . . . . ?
C17 C12 C13 C14 0.4(5) . . . . ?
C18 N2 C6 C5 -45.2(3) . . . . ?
C18 N2 C7 C8 -58.8(4) . . . . ?
C19 C5 C6 N2 32.0(3) . . . . ?
C19 C5 C13 C12 119.4(3) . . . . ?
C19 C5 C13 C14 -60.2(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'manual mounting'
_olex2_submission_original_sample_id 241125WayamaKaneko
_olex2_submission_special_instructions 'No special instructions were received'


