# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_p2
_database_code_depnum_ccdc_archive 'CCDC 2119444'
loop_
_audit_author_name
_audit_author_address
'Yasuhiro Kubota'
;Gifu University
Japan
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-11-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 N2 O2'
_chemical_formula_sum            'C10 H12 N2 O2'
_chemical_formula_weight         192.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.13210(10)
_cell_length_b                   9.99270(10)
_cell_length_c                   15.33430(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.2250(10)
_cell_angle_gamma                90
_cell_volume                     939.621(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4474
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6110
_cell_measurement_theta_min      2.8540
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.773
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 6 0.0848
0 5 -6 0.0979
3 -2 -5 0.1365
4 0 -2 0.1369
1 -4 -8 0.1270
0 4 8 0.1053
-4 1 2 0.1401
-1 -4 -8 0.1510
4 0 -1 0.1279
2 -1 9 0.1333
-1 -6 1 0.1352
-2 -3 -7 0.1653
2 -5 3 0.1081
1 -6 -2 0.0903
-1 -5 -5 0.1317
-1 6 0 0.1217
3 -4 0 0.1080
0 -6 -5 0.1041
-2 6 3 0.1247
-2 3 7 0.1031
-2 2 7 0.0988
-4 0 3 0.1349
-1 1 9 0.0732
-2 0 8 0.1065

_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.184
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1077 -5.2993 5.7343 -0.9968 -0.0791 -0.0090
-0.0858 5.3298 -5.6699 0.9967 0.0791 0.0187
3.3634 -1.8681 -4.5124 0.0790 -0.9962 0.0363
3.9977 -0.0025 -1.9965 0.1536 -0.9130 0.4361
0.9987 -4.0002 -7.9918 0.0189 -0.7779 -0.6939
0.0007 3.9998 7.9925 -0.0114 0.5710 0.8361
-3.9975 1.0016 1.9954 -0.0326 0.9700 -0.3598
-1.0002 -3.9994 -7.9931 0.0040 -0.3642 -0.9783
3.9977 -0.0021 -0.9969 0.0917 -0.8701 0.5024
1.9986 -0.9959 8.9990 -0.6639 -0.0846 0.8054
-1.0006 -5.9936 1.0057 -0.7959 -0.0922 -0.5335
-1.9994 -2.9995 -6.9953 0.0557 -0.0576 -0.9778
1.9978 -4.9949 3.0058 -0.7765 -0.5698 0.1021
0.9982 -5.9957 -1.9918 -0.5951 -0.6345 -0.4482
-1.0004 -4.9972 -4.9932 -0.3030 -0.2925 -0.8555
-0.9982 5.9949 -0.0074 0.7191 0.5487 0.3155
2.9975 -3.9975 0.0065 -0.4620 -0.8483 0.1215
-0.0012 -5.9966 -4.9914 -0.4166 -0.5563 -0.7895
-1.9977 5.9966 2.9908 0.5257 0.8842 0.3724
-1.9983 3.0011 6.9926 -0.0854 0.8848 0.4090
-1.9985 2.0020 6.9937 -0.2065 0.8278 0.3328
-3.9977 0.0029 2.9961 -0.2156 0.9559 -0.3697
-0.9993 1.0034 8.9948 -0.4441 0.6498 0.5314
-1.9989 0.0043 7.9956 -0.5106 0.7567 0.2466

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0098
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5182
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.749
_diffrn_reflns_theta_min         5.283
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  74.00   0.50    0.05    --   67.84-125.00-120.00   52
  2  ω     26.00  90.00   0.50    0.05    --   67.84-125.00 -30.00  128
  3  ω     38.00  66.00   0.50    0.05    --   67.84   0.00 120.00   56
  4  ω     76.00 102.00   0.50    0.05    --   67.84   0.00 120.00   52
  5  ω    -97.00 -45.00   0.50    0.05    --  -69.93   0.00-120.00  104
  6  ω    -95.00 -57.00   0.50    0.05    --  -68.75 125.00-180.00   76
  7  ω   -102.00 -74.00   0.50    0.05    --  -80.25 125.00-120.00   56
  8  ω    -74.00 -40.00   0.50    0.05    --  -69.93 125.00  90.00   68
  9  ω   -104.00 -57.00   0.50    0.05    --  -80.25 125.00 120.00   94
 10  ω   -104.00 -40.00   0.50    0.05    --  -68.75 -15.00 120.00  128
 11  ω   -119.00 -58.00   0.50    0.05    --  -80.25 -15.00  90.00  122
 12  ω   -111.00 -50.00   0.50    0.05    --  -69.93 -15.00   0.00  122
 13  ω   -121.00 -51.00   0.50    0.05    --  -80.25 -15.00 -30.00  140
 14  ω   -120.00 -64.00   0.50    0.05    --  -80.25 -15.00-150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0075209000
_diffrn_orient_matrix_UB_12      0.1211212000
_diffrn_orient_matrix_UB_13      -0.0620455000
_diffrn_orient_matrix_UB_21      -0.2069328000
_diffrn_orient_matrix_UB_22      0.0571201000
_diffrn_orient_matrix_UB_23      0.0428817000
_diffrn_orient_matrix_UB_31      0.1422660000
_diffrn_orient_matrix_UB_32      0.0764009000
_diffrn_orient_matrix_UB_33      0.0663614000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1799
_reflns_number_total             1848
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_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         0.258
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1848
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.092
_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)+(0.0394P)²+0.3588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C)
;
_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
O2 O -0.04640(12) 0.85918(7) 0.58823(5) 0.01940(19) Uani 1 1 d . . . . .
O1 O -0.09874(13) 0.68033(8) 0.50031(5) 0.0220(2) Uani 1 1 d . . . . .
N1 N 0.28346(14) 0.56047(9) 0.57795(6) 0.0186(2) Uani 1 1 d . . . . .
H1 H 0.225196 0.503041 0.541119 0.022 Uiso 1 1 calc R U . . .
N2 N 0.70060(14) 0.64224(9) 0.71945(6) 0.0192(2) Uani 1 1 d . . . . .
C2 C 0.20152(17) 0.68553(11) 0.59895(7) 0.0173(2) Uani 1 1 d . . . . .
C3 C 0.33643(17) 0.74865(10) 0.65958(7) 0.0176(2) Uani 1 1 d . . . . .
H3 H 0.317951 0.834714 0.684812 0.021 Uiso 1 1 calc R U . . .
C7 C 0.47184(17) 0.54242(11) 0.62499(7) 0.0181(2) Uani 1 1 d . . . . .
C4 C 0.50560(17) 0.65710(11) 0.67514(7) 0.0174(2) Uani 1 1 d . . . . .
C5 C 0.78355(18) 0.51889(11) 0.69682(7) 0.0213(2) Uani 1 1 d . . . . .
H5 H 0.916870 0.483505 0.718571 0.026 Uiso 1 1 calc R U . . .
C8 C 0.00597(17) 0.73667(11) 0.55727(7) 0.0173(2) Uani 1 1 d . . . . .
C6 C 0.64949(18) 0.45353(11) 0.63891(7) 0.0219(2) Uani 1 1 d . . . . .
H6 H 0.670815 0.367720 0.613676 0.026 Uiso 1 1 calc R U . . .
C9 C -0.23749(17) 0.92133(11) 0.54966(7) 0.0202(2) Uani 1 1 d . . . . .
H9A H -0.363395 0.859420 0.551825 0.024 Uiso 1 1 calc R U . . .
H9B H -0.209414 0.944787 0.487988 0.024 Uiso 1 1 calc R U . . .
C1 C 0.79293(18) 0.73488(12) 0.78235(7) 0.0230(3) Uani 1 1 d . . . . .
H1A H 0.738562 0.825308 0.770472 0.034 Uiso 1 1 calc R U . . .
H1B H 0.952285 0.734018 0.777753 0.034 Uiso 1 1 calc R U . . .
H1C H 0.750347 0.707909 0.841319 0.034 Uiso 1 1 calc R U . . .
C10 C -0.28410(19) 1.04565(12) 0.60201(8) 0.0272(3) Uani 1 1 d . . . . .
H10A H -0.410281 1.092189 0.576939 0.041 Uiso 1 1 calc R U . . .
H10B H -0.156731 1.104840 0.600645 0.041 Uiso 1 1 calc R U . . .
H10C H -0.315591 1.020766 0.662478 0.041 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
O2 C8 1.3522(13) . ?
O2 C9 1.4502(12) . ?
O1 C8 1.2196(13) . ?
N1 H1 0.8800 . ?
N1 C2 1.3853(14) . ?
N1 C7 1.3714(14) . ?
N2 C4 1.3810(14) . ?
N2 C5 1.3784(14) . ?
N2 C1 1.4503(14) . ?
C2 C3 1.3930(15) . ?
C2 C8 1.4497(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.4029(15) . ?
C7 C4 1.3951(15) . ?
C7 C6 1.4210(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3730(16) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5071(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C9 115.92(8) . . ?
C2 N1 H1 126.2 . . ?
C7 N1 H1 126.2 . . ?
C7 N1 C2 107.57(9) . . ?
C4 N2 C1 126.41(9) . . ?
C5 N2 C4 106.97(9) . . ?
C5 N2 C1 126.50(9) . . ?
N1 C2 C3 110.40(9) . . ?
N1 C2 C8 121.04(9) . . ?
C3 C2 C8 128.52(10) . . ?
C2 C3 H3 127.6 . . ?
C2 C3 C4 104.78(9) . . ?
C4 C3 H3 127.6 . . ?
N1 C7 C4 107.74(9) . . ?
N1 C7 C6 143.60(10) . . ?
C4 C7 C6 108.58(10) . . ?
N2 C4 C3 142.38(10) . . ?
N2 C4 C7 108.01(9) . . ?
C7 C4 C3 109.50(9) . . ?
N2 C5 H5 124.2 . . ?
C6 C5 N2 111.57(10) . . ?
C6 C5 H5 124.2 . . ?
O2 C8 C2 111.19(9) . . ?
O1 C8 O2 122.97(10) . . ?
O1 C8 C2 125.82(10) . . ?
C7 C6 H6 127.6 . . ?
C5 C6 C7 104.86(10) . . ?
C5 C6 H6 127.6 . . ?
O2 C9 H9A 110.3 . . ?
O2 C9 H9B 110.3 . . ?
O2 C9 C10 106.88(8) . . ?
H9A C9 H9B 108.6 . . ?
C10 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 0.02(11) . . . . ?
N1 C2 C8 O2 179.13(8) . . . . ?
N1 C2 C8 O1 -2.29(17) . . . . ?
N1 C7 C4 N2 -177.13(8) . . . . ?
N1 C7 C4 C3 0.00(12) . . . . ?
N1 C7 C6 C5 175.87(14) . . . . ?
N2 C5 C6 C7 -0.09(12) . . . . ?
C2 N1 C7 C4 0.01(11) . . . . ?
C2 N1 C7 C6 -176.09(14) . . . . ?
C2 C3 C4 N2 175.52(14) . . . . ?
C2 C3 C4 C7 -0.02(12) . . . . ?
C3 C2 C8 O2 -3.58(15) . . . . ?
C3 C2 C8 O1 175.01(10) . . . . ?
C7 N1 C2 C3 -0.02(12) . . . . ?
C7 N1 C2 C8 177.72(9) . . . . ?
C4 N2 C5 C6 0.35(12) . . . . ?
C4 C7 C6 C5 -0.21(12) . . . . ?
C5 N2 C4 C3 -176.05(14) . . . . ?
C5 N2 C4 C7 -0.47(12) . . . . ?
C8 O2 C9 C10 171.96(9) . . . . ?
C8 C2 C3 C4 -177.50(10) . . . . ?
C6 C7 C4 N2 0.43(12) . . . . ?
C6 C7 C4 C3 177.56(9) . . . . ?
C9 O2 C8 O1 0.14(14) . . . . ?
C9 O2 C8 C2 178.77(8) . . . . ?
C1 N2 C4 C3 7.8(2) . . . . ?
C1 N2 C4 C7 -176.66(10) . . . . ?
C1 N2 C5 C6 176.54(10) . . . . ?

_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 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.670
####################################################################### 
# 
# 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_p5
_database_code_depnum_ccdc_archive 'CCDC 2075567'
loop_
_audit_author_name
_audit_author_address
'Yasuhiro Kubota'
;Gifu University
Japan
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-11-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N3 O2'
_chemical_formula_sum            'C20 H25 N3 O2'
_chemical_formula_weight         339.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.6244(3)
_cell_length_b                   12.3177(3)
_cell_length_c                   14.0897(6)
_cell_angle_alpha                90.747(3)
_cell_angle_beta                 96.017(3)
_cell_angle_gamma                93.379(2)
_cell_volume                     1830.20(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14435
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      75.1560
_cell_measurement_theta_min      3.1490
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 9 0.0086
-1 1 -9 0.0086
-6 -3 3 0.0907
-3 -7 0 0.0780
-6 4 2 0.0458
6 -4 -2 0.0561
7 1 -1 0.0455
-3 7 2 0.0684

_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.017
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.2066 -0.8444 8.7604 -0.0255 -0.9925 -0.1194
-1.2066 0.8444 -8.7604 0.0255 0.9925 0.1194
-6.1371 -2.8978 2.6359 -0.0035 -0.1869 0.9824
-2.9509 -6.9652 -0.3700 -0.6626 0.0178 0.7488
-6.1962 3.7933 1.8825 0.7532 -0.0184 0.6575
6.0412 -4.1303 -1.8978 -0.7847 0.0193 -0.6196
6.7383 1.2181 -1.2757 -0.1970 0.0038 -0.9804
-2.9302 7.3146 1.6882 0.9990 -0.0256 0.0368

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26401
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.496
_diffrn_reflns_theta_min         3.154
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  95.00   0.50    0.50    --   67.84   0.00 150.00  124
  2  ω     48.00  73.00   0.50    0.50    --   67.84-135.00-115.00   50
  3  ω     41.00  66.00   0.50    0.50    --   69.39-135.00-115.00   50
  4  ω     46.00 109.00   0.50    0.50    --   67.84  15.00-120.00  126
  5  ω     33.00  94.00   0.50    0.50    --   67.84   0.00-150.00  122
  6  ω     37.00  82.00   0.50    0.50    --   69.39-134.00  64.00   90
  7  ω     28.00  63.00   0.50    0.50    --   67.84-125.00 120.00   70
  8  ω     39.00  64.00   0.50    0.50    --   67.84-134.00  64.00   50
  9  ω     32.00  77.00   0.50    0.50    --   67.84-125.00  30.00   90
 10  ω     32.00  96.00   0.50    0.50    --   69.39-125.00   0.00  128
 11  ω   -119.00 -76.00   0.50    0.50    --  -80.25-135.00-115.00   86
 12  ω   -106.00 -57.00   0.50    0.50    --  -80.25 -15.00 -90.00   98
 13  ω   -111.00 -84.00   0.50    0.50    --  -69.93 -15.00-180.00   54
 14  ω    -78.00 -43.00   0.50    0.50    --  -69.93 -15.00-180.00   70
 15  ω   -102.00 -55.00   0.50    0.50    --  -80.25 -15.00-180.00   94
 16  ω    -88.00 -61.00   0.50    0.50    --  -80.25 -15.00-150.00   54
 17  ω    -86.00 -58.00   0.50    0.50    --  -80.25 -15.00   0.00   56
 18  ω   -122.00 -92.00   0.50    0.50    --  -80.25 -15.00   0.00   60
 19  ω    -89.00 -59.00   0.50    0.50    --  -80.25 -15.00 120.00   60
 20  ω    -98.00 -71.00   0.50    0.50    --  -80.25   0.00 -90.00   54
 21  ω    -85.00 -52.00   0.50    0.50    --  -69.93   0.00-150.00   66
 22  ω    -80.00 -53.00   0.50    0.50    --  -80.25   0.00-150.00   54
 23  ω   -111.00 -53.00   0.50    0.50    --  -80.25 135.00 -49.00  116
 24  ω    -88.00 -63.00   0.50    0.50    --  -68.75 135.00 -49.00   50
 25  ω    -80.00 -51.00   0.50    0.50    --  -68.75 125.00-180.00   58
 26  ω    -95.00 -65.00   0.50    0.50    --  -68.75 125.00  30.00   60
 27  ω    -88.00 -63.00   0.50    0.50    --  -68.75 134.00 130.00   50
 28  ω   -100.00 -70.00   0.50    0.50    --  -69.93 134.00 130.00   60
 29  ω   -110.00 -70.00   0.50    0.50    --  -80.25 134.00 130.00   80
 30  ω    -92.00 -32.00   0.50    0.50    --  -68.75 125.00  90.00  120
 31  ω   -103.00 -41.00   0.50    0.50    --  -80.25 125.00 120.00  124
 32  ω   -106.00 -38.00   0.50    0.50    --  -80.25 125.00  60.00  136
 33  ω    -96.00 -45.00   0.50    0.50    --  -69.93 125.00   0.00  102
 34  ω   -106.00 -45.00   0.50    0.50    --  -80.25 125.00 -90.00  122
 35  ω    -95.00 -62.00   0.50    0.50    --  -68.75 125.00-120.00   66
 36  ω    -66.00 -41.00   0.50    0.50    --  -80.25 125.00-150.00   50
 37  ω   -103.00 -39.00   0.50    0.50    --  -80.25 125.00-180.00  128
 38  ω   -106.00 -80.00   0.50    0.50    --  -80.25 125.00-120.00   52
 39  ω   -100.00 -35.00   0.50    0.50    --  -75.44 123.00-142.40  130
 40  ω   -102.00 -76.00   0.50    0.50    --  -80.25 125.00   0.00   52
 41  ω    -63.00 -38.00   0.50    0.50    --  -80.25 125.00   0.00   50
 42  ω    -63.00 -33.00   0.50    0.50    --  -75.44 124.00  63.79   60
 43  ω   -100.00 -75.00   0.50    0.50    --  -75.44 124.00  63.79   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471372000
_diffrn_orient_matrix_UB_12      0.1143233000
_diffrn_orient_matrix_UB_13      0.0146007000
_diffrn_orient_matrix_UB_21      -0.0223624000
_diffrn_orient_matrix_UB_22      0.0127016000
_diffrn_orient_matrix_UB_23      -0.1089913000
_diffrn_orient_matrix_UB_31      -0.1364399000
_diffrn_orient_matrix_UB_32      -0.0497150000
_diffrn_orient_matrix_UB_33      0.0003660000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6589
_reflns_number_total             7268
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_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         0.336
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         7268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.080
_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)+(0.1065P)²+0.6744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1694
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C17'(H17C,H17D), C19'(H19C,H19D), C9(H9A,H9B), C9'(H9'A,H9'B),
  C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1'(H1'), N1(H1), C6'(H6'), C12(H12), C16(H16), C15'(H15'), C15(H15),
 C3'(H3'), C6(H6), C13(H13), C3(H3), C13'(H13'), C16'(H16'), C12'(H12')
2.c Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C1(H1A,H1B,H1C), C18'(H18D,H18E,H18F), C20(H20A,H20B,
 H20C), C10(H10A,H10B,H10C), C20'(H20D,H20E,H20F), C10'(H10D,H10E,H10F),
 C18(H18A,H18B,H18C)
;
_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
O2 O 0.67155(12) 0.10851(10) 0.28992(8) 0.0284(3) Uani 1 1 d . . . . .
O1 O 0.57328(12) -0.00554(10) 0.38585(9) 0.0310(3) Uani 1 1 d . . . . .
O1' O 1.36547(12) 0.81112(10) 1.11470(9) 0.0309(3) Uani 1 1 d . . . . .
O2' O 1.15583(12) 0.79247(11) 1.13403(9) 0.0339(3) Uani 1 1 d . . . . .
N2 N 0.64838(13) 0.43412(11) 0.56233(10) 0.0239(3) Uani 1 1 d . . . . .
N1' N 1.31392(13) 0.67706(11) 0.94656(10) 0.0240(3) Uani 1 1 d . . . . .
H1' H 1.395317 0.696873 0.955003 0.029 Uiso 1 1 calc R U . . .
N1 N 0.56918(13) 0.16172(12) 0.52096(10) 0.0253(3) Uani 1 1 d . . . . .
H1 H 0.537820 0.099657 0.541425 0.030 Uiso 1 1 calc R U . . .
N2' N 1.06588(13) 0.52945(12) 0.81909(10) 0.0241(3) Uani 1 1 d . . . . .
N3 N 0.59255(13) 0.73245(12) 0.95000(10) 0.0254(3) Uani 1 1 d . . . . .
N00A N 1.06887(14) 0.16129(12) 0.47661(10) 0.0275(3) Uani 1 1 d . . . . .
C7 C 0.58057(15) 0.25880(14) 0.56944(12) 0.0237(3) Uani 1 1 d . . . . .
C11 C 0.60328(15) 0.50073(14) 0.72493(12) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.60069(15) 0.65768(13) 0.87579(12) 0.0237(3) Uani 1 1 d . . . . .
C7' C 1.25487(15) 0.60963(14) 0.87565(12) 0.0236(3) Uani 1 1 d . . . . .
C4' C 1.12597(15) 0.59954(14) 0.88763(12) 0.0247(3) Uani 1 1 d . . . . .
C5 C 0.60305(15) 0.41645(14) 0.65045(12) 0.0233(3) Uani 1 1 d . . . . .
C4 C 0.63477(15) 0.33630(14) 0.51264(12) 0.0238(3) Uani 1 1 d . . . . .
C6' C 1.27601(15) 0.54309(14) 0.79708(12) 0.0252(3) Uani 1 1 d . . . . .
H6' H 1.354398 0.533670 0.772122 0.030 Uiso 1 1 calc R U . . .
C12 C 0.58643(15) 0.61070(14) 0.70650(12) 0.0254(3) Uani 1 1 d . . . . .
H12 H 0.575693 0.633630 0.642196 0.030 Uiso 1 1 calc R U . . .
C8 C 0.61651(15) 0.08583(14) 0.36972(12) 0.0254(3) Uani 1 1 d . . . . .
C16 C 0.61675(15) 0.47154(14) 0.82114(12) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.626759 0.397397 0.836259 0.030 Uiso 1 1 calc R U . . .
C15' C 1.20447(15) 0.25493(14) 0.60652(12) 0.0252(3) Uani 1 1 d . . . . .
H15' H 1.269200 0.206068 0.600388 0.030 Uiso 1 1 calc R U . . .
C15 C 0.61602(15) 0.54648(14) 0.89470(12) 0.0252(3) Uani 1 1 d . . . . .
H15 H 0.625938 0.523075 0.958884 0.030 Uiso 1 1 calc R U . . .
C5' C 1.15786(15) 0.49431(14) 0.76400(12) 0.0246(3) Uani 1 1 d . . . . .
C2' C 1.22229(16) 0.70865(14) 1.00289(12) 0.0252(3) Uani 1 1 d . . . . .
C11' C 1.13096(15) 0.41114(14) 0.68843(12) 0.0246(3) Uani 1 1 d . . . . .
C14' C 1.09164(15) 0.24417(14) 0.54331(12) 0.0245(3) Uani 1 1 d . . . . .
C8' C 1.25807(16) 0.77571(13) 1.08743(12) 0.0253(3) Uani 1 1 d . . . . .
C3' C 1.10407(16) 0.66233(14) 0.96796(12) 0.0262(4) Uani 1 1 d . . . . .
H3' H 1.025434 0.671025 0.992781 0.031 Uiso 1 1 calc R U . . .
C6 C 0.56038(15) 0.30808(14) 0.65695(12) 0.0244(3) Uani 1 1 d . . . . .
H6 H 0.525142 0.274456 0.709265 0.029 Uiso 1 1 calc R U . . .
C2 C 0.61585(15) 0.17811(14) 0.43356(12) 0.0246(3) Uani 1 1 d . . . . .
C13 C 0.58498(16) 0.68703(14) 0.77956(12) 0.0262(4) Uani 1 1 d . . . . .
H13 H 0.573101 0.760828 0.764116 0.031 Uiso 1 1 calc R U . . .
C19 C 0.64684(16) 0.70825(14) 1.04692(12) 0.0266(4) Uani 1 1 d . . . . .
H19A H 0.605465 0.639239 1.066572 0.032 Uiso 1 1 calc R U . . .
H19B H 0.626305 0.766440 1.090878 0.032 Uiso 1 1 calc R U . . .
C3 C 0.65874(15) 0.28677(14) 0.42626(12) 0.0241(3) Uani 1 1 d . . . . .
H3 H 0.695841 0.319889 0.374506 0.029 Uiso 1 1 calc R U . . .
C13' C 1.00096(16) 0.32226(15) 0.55409(13) 0.0283(4) Uani 1 1 d . . . . .
H13' H 0.924681 0.319209 0.512170 0.034 Uiso 1 1 calc R U . . .
C16' C 1.22230(15) 0.33476(14) 0.67669(12) 0.0249(3) Uani 1 1 d . . . . .
H16' H 1.298595 0.338576 0.718601 0.030 Uiso 1 1 calc R U . . .
C17' C 0.96474(17) 0.16491(15) 0.40048(13) 0.0290(4) Uani 1 1 d . . . . .
H17C H 0.885613 0.176003 0.429740 0.035 Uiso 1 1 calc R U . . .
H17D H 0.954060 0.093474 0.366678 0.035 Uiso 1 1 calc R U . . .
C1' C 0.93230(16) 0.49460(15) 0.81411(13) 0.0294(4) Uani 1 1 d . . . . .
H1'A H 0.902925 0.502415 0.877356 0.044 Uiso 1 1 calc R U . . .
H1'B H 0.920389 0.418245 0.792932 0.044 Uiso 1 1 calc R U . . .
H1'C H 0.883455 0.539638 0.768672 0.044 Uiso 1 1 calc R U . . .
C12' C 1.02114(16) 0.40240(14) 0.62403(12) 0.0277(4) Uani 1 1 d . . . . .
H12' H 0.958362 0.453478 0.628688 0.033 Uiso 1 1 calc R U . . .
C1 C 0.70526(17) 0.53320(14) 0.52572(13) 0.0283(4) Uani 1 1 d . . . . .
H1A H 0.638414 0.576524 0.495231 0.043 Uiso 1 1 calc R U . . .
H1B H 0.762671 0.514382 0.478783 0.043 Uiso 1 1 calc R U . . .
H1C H 0.753003 0.575438 0.578478 0.043 Uiso 1 1 calc R U . . .
C19' C 1.16009(17) 0.07841(14) 0.46782(13) 0.0294(4) Uani 1 1 d . . . . .
H19C H 1.113190 0.009274 0.445848 0.035 Uiso 1 1 calc R U . . .
H19D H 1.204628 0.066285 0.531756 0.035 Uiso 1 1 calc R U . . .
C18' C 0.98201(19) 0.25331(17) 0.32742(14) 0.0369(4) Uani 1 1 d . . . . .
H18D H 0.905645 0.253381 0.281916 0.055 Uiso 1 1 calc R U . . .
H18E H 1.055177 0.239074 0.293174 0.055 Uiso 1 1 calc R U . . .
H18F H 0.996310 0.324312 0.360211 0.055 Uiso 1 1 calc R U . . .
C9 C 0.68482(19) 0.01494(15) 0.22880(13) 0.0318(4) Uani 1 1 d . . . . .
H9A H 0.600363 -0.016110 0.201844 0.038 Uiso 1 1 calc R U . . .
H9B H 0.729121 -0.041933 0.265731 0.038 Uiso 1 1 calc R U . . .
C9' C 1.17759(19) 0.84194(16) 1.22831(13) 0.0341(4) Uani 1 1 d . . . . .
H9'A H 1.238270 0.906153 1.228798 0.041 Uiso 1 1 calc R U . . .
H9'B H 1.212261 0.789352 1.275205 0.041 Uiso 1 1 calc R U . . .
C20 C 0.79023(17) 0.69824(17) 1.05860(14) 0.0333(4) Uani 1 1 d . . . . .
H20A H 0.811547 0.637968 1.018316 0.050 Uiso 1 1 calc R U . . .
H20B H 0.818570 0.684239 1.125525 0.050 Uiso 1 1 calc R U . . .
H20C H 0.832555 0.766081 1.039453 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5850(2) 0.84822(15) 0.92755(14) 0.0361(4) Uani 1 1 d . . . . .
H17A H 0.558053 0.886425 0.983564 0.043 Uiso 1 1 calc R U . . .
H17B H 0.517918 0.854734 0.873970 0.043 Uiso 1 1 calc R U . . .
C10 C 0.7607(2) 0.05383(17) 0.15002(14) 0.0396(5) Uani 1 1 d . . . . .
H10A H 0.771224 -0.007371 0.107008 0.059 Uiso 1 1 calc R U . . .
H10B H 0.844132 0.083960 0.177584 0.059 Uiso 1 1 calc R U . . .
H10C H 0.715976 0.110206 0.114172 0.059 Uiso 1 1 calc R U . . .
C20' C 1.25845(19) 0.10670(18) 0.39949(15) 0.0400(5) Uani 1 1 d . . . . .
H20D H 1.215656 0.116446 0.335367 0.060 Uiso 1 1 calc R U . . .
H20E H 1.316134 0.047650 0.397817 0.060 Uiso 1 1 calc R U . . .
H20F H 1.306866 0.174219 0.421280 0.060 Uiso 1 1 calc R U . . .
C10' C 1.0501(2) 0.8752(2) 1.25199(16) 0.0466(5) Uani 1 1 d . . . . .
H10D H 1.020980 0.932339 1.208701 0.070 Uiso 1 1 calc R U . . .
H10E H 1.057446 0.902779 1.318015 0.070 Uiso 1 1 calc R U . . .
H10F H 0.988995 0.812122 1.244646 0.070 Uiso 1 1 calc R U . . .
C18 C 0.7058(3) 0.90664(18) 0.90103(16) 0.0487(6) Uani 1 1 d . . . . .
H18A H 0.735546 0.868641 0.846842 0.073 Uiso 1 1 calc R U . . .
H18B H 0.771065 0.907492 0.955675 0.073 Uiso 1 1 calc R U . . .
H18C H 0.688857 0.981502 0.883455 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
O2 C8 1.346(2) . ?
O2 C9 1.452(2) . ?
O1 C8 1.223(2) . ?
O1' C8' 1.219(2) . ?
O2' C8' 1.351(2) . ?
O2' C9' 1.445(2) . ?
N2 C5 1.393(2) . ?
N2 C4 1.378(2) . ?
N2 C1 1.454(2) . ?
N1' H1' 0.8800 . ?
N1' C7' 1.366(2) . ?
N1' C2' 1.388(2) . ?
N1 H1 0.8800 . ?
N1 C7 1.362(2) . ?
N1 C2 1.388(2) . ?
N2' C4' 1.367(2) . ?
N2' C5' 1.395(2) . ?
N2' C1' 1.453(2) . ?
N3 C14 1.397(2) . ?
N3 C19 1.467(2) . ?
N3 C17 1.470(2) . ?
N00A C14' 1.372(2) . ?
N00A C17' 1.461(2) . ?
N00A C19' 1.461(2) . ?
C7 C4 1.391(2) . ?
C7 C6 1.409(2) . ?
C11 C5 1.466(2) . ?
C11 C12 1.401(2) . ?
C11 C16 1.402(2) . ?
C14 C15 1.414(2) . ?
C14 C13 1.403(2) . ?
C7' C4' 1.396(2) . ?
C7' C6' 1.413(2) . ?
C4' C3' 1.410(2) . ?
C5 C6 1.392(2) . ?
C4 C3 1.408(2) . ?
C6' H6' 0.9500 . ?
C6' C5' 1.391(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C8 C2 1.441(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.380(2) . ?
C15' H15' 0.9500 . ?
C15' C14' 1.415(2) . ?
C15' C16' 1.376(2) . ?
C15 H15 0.9500 . ?
C5' C11' 1.462(2) . ?
C2' C8' 1.445(2) . ?
C2' C3' 1.387(2) . ?
C11' C16' 1.411(2) . ?
C11' C12' 1.399(2) . ?
C14' C13' 1.419(2) . ?
C3' H3' 0.9500 . ?
C6 H6 0.9500 . ?
C2 C3 1.397(2) . ?
C13 H13 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.527(2) . ?
C3 H3 0.9500 . ?
C13' H13' 0.9500 . ?
C13' C12' 1.377(2) . ?
C16' H16' 0.9500 . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C17' C18' 1.525(3) . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C12' H12' 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
C19' C20' 1.522(3) . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.506(3) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C9' C10' 1.507(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.518(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C9 114.87(14) . . ?
C8' O2' C9' 117.77(14) . . ?
C5 N2 C1 129.20(14) . . ?
C4 N2 C5 107.35(14) . . ?
C4 N2 C1 123.42(14) . . ?
C7' N1' H1' 126.2 . . ?
C7' N1' C2' 107.64(14) . . ?
C2' N1' H1' 126.2 . . ?
C7 N1 H1 126.1 . . ?
C7 N1 C2 107.83(14) . . ?
C2 N1 H1 126.1 . . ?
C4' N2' C5' 107.25(13) . . ?
C4' N2' C1' 123.69(14) . . ?
C5' N2' C1' 128.86(14) . . ?
C14 N3 C19 119.44(13) . . ?
C14 N3 C17 118.86(14) . . ?
C19 N3 C17 116.12(14) . . ?
C14' N00A C17' 120.40(14) . . ?
C14' N00A C19' 121.45(14) . . ?
C17' N00A C19' 117.13(14) . . ?
N1 C7 C4 108.14(14) . . ?
N1 C7 C6 142.75(16) . . ?
C4 C7 C6 109.08(15) . . ?
C12 C11 C5 124.01(15) . . ?
C12 C11 C16 116.48(15) . . ?
C16 C11 C5 119.48(15) . . ?
N3 C14 C15 120.83(15) . . ?
N3 C14 C13 122.10(15) . . ?
C13 C14 C15 116.91(15) . . ?
N1' C7' C4' 108.02(14) . . ?
N1' C7' C6' 143.60(15) . . ?
C4' C7' C6' 108.31(15) . . ?
N2' C4' C7' 108.87(14) . . ?
N2' C4' C3' 142.07(15) . . ?
C7' C4' C3' 109.01(15) . . ?
N2 C5 C11 124.07(15) . . ?
C6 C5 N2 110.04(15) . . ?
C6 C5 C11 125.88(15) . . ?
N2 C4 C7 108.17(14) . . ?
N2 C4 C3 142.48(16) . . ?
C7 C4 C3 109.33(15) . . ?
C7' C6' H6' 127.2 . . ?
C5' C6' C7' 105.50(14) . . ?
C5' C6' H6' 127.2 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.81(15) . . ?
C13 C12 H12 119.1 . . ?
O2 C8 C2 113.70(15) . . ?
O1 C8 O2 122.21(16) . . ?
O1 C8 C2 124.08(16) . . ?
C11 C16 H16 118.8 . . ?
C15 C16 C11 122.46(15) . . ?
C15 C16 H16 118.8 . . ?
C14' C15' H15' 119.3 . . ?
C16' C15' H15' 119.3 . . ?
C16' C15' C14' 121.31(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.87(15) . . ?
C16 C15 H15 119.6 . . ?
N2' C5' C11' 123.04(15) . . ?
C6' C5' N2' 110.06(15) . . ?
C6' C5' C11' 126.71(15) . . ?
N1' C2' C8' 120.25(15) . . ?
C3' C2' N1' 110.32(15) . . ?
C3' C2' C8' 129.34(15) . . ?
C16' C11' C5' 118.78(15) . . ?
C12' C11' C5' 124.77(15) . . ?
C12' C11' C16' 116.43(15) . . ?
N00A C14' C15' 122.19(15) . . ?
N00A C14' C13' 121.37(15) . . ?
C15' C14' C13' 116.42(15) . . ?
O1' C8' O2' 124.07(16) . . ?
O1' C8' C2' 125.31(15) . . ?
O2' C8' C2' 110.60(15) . . ?
C4' C3' H3' 127.5 . . ?
C2' C3' C4' 105.00(14) . . ?
C2' C3' H3' 127.5 . . ?
C7 C6 H6 127.3 . . ?
C5 C6 C7 105.36(15) . . ?
C5 C6 H6 127.3 . . ?
N1 C2 C8 118.25(15) . . ?
N1 C2 C3 110.04(14) . . ?
C3 C2 C8 131.68(16) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.47(15) . . ?
C12 C13 H13 119.3 . . ?
N3 C19 H19A 108.5 . . ?
N3 C19 H19B 108.5 . . ?
N3 C19 C20 114.97(14) . . ?
H19A C19 H19B 107.5 . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C4 C3 H3 127.7 . . ?
C2 C3 C4 104.66(15) . . ?
C2 C3 H3 127.7 . . ?
C14' C13' H13' 119.3 . . ?
C12' C13' C14' 121.41(16) . . ?
C12' C13' H13' 119.3 . . ?
C15' C16' C11' 122.16(15) . . ?
C15' C16' H16' 118.9 . . ?
C11' C16' H16' 118.9 . . ?
N00A C17' H17C 108.5 . . ?
N00A C17' H17D 108.5 . . ?
N00A C17' C18' 114.89(15) . . ?
H17C C17' H17D 107.5 . . ?
C18' C17' H17C 108.5 . . ?
C18' C17' H17D 108.5 . . ?
N2' C1' H1'A 109.5 . . ?
N2' C1' H1'B 109.5 . . ?
N2' C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
C11' C12' H12' 118.9 . . ?
C13' C12' C11' 122.22(15) . . ?
C13' C12' H12' 118.9 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N00A C19' H19C 108.7 . . ?
N00A C19' H19D 108.7 . . ?
N00A C19' C20' 114.38(15) . . ?
H19C C19' H19D 107.6 . . ?
C20' C19' H19C 108.7 . . ?
C20' C19' H19D 108.7 . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18E 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
O2 C9 H9A 110.3 . . ?
O2 C9 H9B 110.3 . . ?
O2 C9 C10 107.19(15) . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
O2' C9' H9'A 110.6 . . ?
O2' C9' H9'B 110.6 . . ?
O2' C9' C10' 105.82(16) . . ?
H9'A C9' H9'B 108.7 . . ?
C10' C9' H9'A 110.6 . . ?
C10' C9' H9'B 110.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C17 H17A 108.2 . . ?
N3 C17 H17B 108.2 . . ?
N3 C17 C18 116.25(17) . . ?
H17A C17 H17B 107.4 . . ?
C18 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C19' C20' H20D 109.5 . . ?
C19' C20' H20E 109.5 . . ?
C19' C20' H20F 109.5 . . ?
H20D C20' H20E 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C9' C10' H10D 109.5 . . ?
C9' C10' H10E 109.5 . . ?
C9' C10' H10F 109.5 . . ?
H10D C10' H10E 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O2 C8 C2 N1 -175.61(13) . . . . ?
O2 C8 C2 C3 2.0(3) . . . . ?
O1 C8 C2 N1 3.4(2) . . . . ?
O1 C8 C2 C3 -179.02(17) . . . . ?
N2 C5 C6 C7 -0.12(18) . . . . ?
N2 C4 C3 C2 178.5(2) . . . . ?
N1' C7' C4' N2' -178.03(13) . . . . ?
N1' C7' C4' C3' 0.06(19) . . . . ?
N1' C7' C6' C5' 176.3(2) . . . . ?
N1' C2' C8' O1' 1.7(3) . . . . ?
N1' C2' C8' O2' -177.02(14) . . . . ?
N1' C2' C3' C4' 0.47(19) . . . . ?
N1 C7 C4 N2 -178.95(13) . . . . ?
N1 C7 C4 C3 -0.26(18) . . . . ?
N1 C7 C6 C5 178.0(2) . . . . ?
N1 C2 C3 C4 -0.69(17) . . . . ?
N2' C4' C3' C2' 176.7(2) . . . . ?
N2' C5' C11' C16' -141.50(17) . . . . ?
N2' C5' C11' C12' 40.1(3) . . . . ?
N3 C14 C15 C16 176.24(15) . . . . ?
N3 C14 C13 C12 -176.43(15) . . . . ?
N00A C14' C13' C12' 176.86(17) . . . . ?
C7 N1 C2 C8 178.65(14) . . . . ?
C7 N1 C2 C3 0.55(18) . . . . ?
C7 C4 C3 C2 0.58(17) . . . . ?
C11 C5 C6 C7 -179.15(14) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C16 C15 C14 0.4(2) . . . . ?
C14 N3 C19 C20 63.0(2) . . . . ?
C14 N3 C17 C18 -72.3(2) . . . . ?
C7' N1' C2' C8' 176.43(14) . . . . ?
C7' N1' C2' C3' -0.45(19) . . . . ?
C7' C4' C3' C2' -0.32(19) . . . . ?
C7' C6' C5' N2' 0.46(19) . . . . ?
C7' C6' C5' C11' -174.60(16) . . . . ?
C4' N2' C5' C6' -0.62(19) . . . . ?
C4' N2' C5' C11' 174.65(15) . . . . ?
C4' C7' C6' C5' -0.13(19) . . . . ?
C5 N2 C4 C7 0.39(17) . . . . ?
C5 N2 C4 C3 -177.6(2) . . . . ?
C5 C11 C12 C13 178.73(15) . . . . ?
C5 C11 C16 C15 -179.09(15) . . . . ?
C4 N2 C5 C11 178.88(14) . . . . ?
C4 N2 C5 C6 -0.17(18) . . . . ?
C4 C7 C6 C5 0.37(18) . . . . ?
C6' C7' C4' N2' -0.25(19) . . . . ?
C6' C7' C4' C3' 177.84(14) . . . . ?
C6' C5' C11' C16' 33.0(3) . . . . ?
C6' C5' C11' C12' -145.44(18) . . . . ?
C12 C11 C5 N2 33.4(2) . . . . ?
C12 C11 C5 C6 -147.69(17) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
C8 O2 C9 C10 -173.73(15) . . . . ?
C8 C2 C3 C4 -178.45(17) . . . . ?
C16 C11 C5 N2 -148.82(16) . . . . ?
C16 C11 C5 C6 30.1(2) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C15' C14' C13' C12' -1.5(3) . . . . ?
C15 C14 C13 C12 -1.0(2) . . . . ?
C5' N2' C4' C7' 0.53(19) . . . . ?
C5' N2' C4' C3' -176.5(2) . . . . ?
C5' C11' C16' C15' -179.23(16) . . . . ?
C5' C11' C12' C13' 179.93(17) . . . . ?
C2' N1' C7' C4' 0.23(18) . . . . ?
C2' N1' C7' C6' -176.2(2) . . . . ?
C14' N00A C17' C18' 67.9(2) . . . . ?
C14' N00A C19' C20' -89.4(2) . . . . ?
C14' C15' C16' C11' -1.2(3) . . . . ?
C14' C13' C12' C11' -0.4(3) . . . . ?
C8' O2' C9' C10' 166.54(17) . . . . ?
C8' C2' C3' C4' -176.04(17) . . . . ?
C3' C2' C8' O1' 177.93(17) . . . . ?
C3' C2' C8' O2' -0.8(3) . . . . ?
C6 C7 C4 N2 -0.48(18) . . . . ?
C6 C7 C4 C3 178.21(13) . . . . ?
C2 N1 C7 C4 -0.17(18) . . . . ?
C2 N1 C7 C6 -177.8(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C19 N3 C14 C15 23.4(2) . . . . ?
C19 N3 C14 C13 -161.33(16) . . . . ?
C19 N3 C17 C18 81.3(2) . . . . ?
C16' C15' C14' N00A -176.06(16) . . . . ?
C16' C15' C14' C13' 2.3(2) . . . . ?
C16' C11' C12' C13' 1.5(3) . . . . ?
C17' N00A C14' C15' -167.51(16) . . . . ?
C17' N00A C14' C13' 14.2(3) . . . . ?
C17' N00A C19' C20' 79.1(2) . . . . ?
C1' N2' C4' C7' 175.85(15) . . . . ?
C1' N2' C4' C3' -1.2(3) . . . . ?
C1' N2' C5' C6' -175.62(16) . . . . ?
C1' N2' C5' C11' -0.3(3) . . . . ?
C12' C11' C16' C15' -0.7(3) . . . . ?
C1 N2 C5 C11 1.1(3) . . . . ?
C1 N2 C5 C6 -177.90(15) . . . . ?
C1 N2 C4 C7 178.29(14) . . . . ?
C1 N2 C4 C3 0.3(3) . . . . ?
C19' N00A C14' C15' 0.6(3) . . . . ?
C19' N00A C14' C13' -177.66(16) . . . . ?
C19' N00A C17' C18' -100.73(18) . . . . ?
C9 O2 C8 O1 -4.8(2) . . . . ?
C9 O2 C8 C2 174.19(14) . . . . ?
C9' O2' C8' O1' -9.1(3) . . . . ?
C9' O2' C8' C2' 169.61(15) . . . . ?
C17 N3 C14 C15 176.05(16) . . . . ?
C17 N3 C14 C13 -8.7(2) . . . . ?
C17 N3 C19 C20 -90.40(19) . . . . ?

_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 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.591
