# Supplementary Information (SI) for CrystEngComm.
# 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_1108_1
_database_code_depnum_ccdc_archive 'CCDC 2419033'
loop_
_audit_author_name
_audit_author_address
'Keiyo Nakai'
;SPERA PHARMA
Japan
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2025-01-23
_audit_creation_method           
;
Olex2 1.5-ac7-002
(compiled 2024.05.10 svn.r6303ca7c for Rigaku Oxford Diffraction, GUI svn.r6967)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            7_Cyano_L_Trp
_chemical_name_systematic        7_Cyano_L_Trp
_chemical_formula_moiety         'C12 H11 N3 O2'
_chemical_formula_sum            'C12 H11 N3 O2'
_chemical_formula_weight         229.24
_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 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_diffrn_oxdiff_scatteringfactors_ed 
;
Peng,L.M. (1999) Micron 30, 625-648
;
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.81(12)
_cell_length_b                   4.94(8)
_cell_length_c                   17.74(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.86(17)
_cell_angle_gamma                90
_cell_volume                     1030(21)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1605
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      0.9240
_cell_measurement_theta_min      0.0700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
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    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             186
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_unetI/netI     0.2236
_diffrn_reflns_Laue_measured_fraction_full 0.649
_diffrn_reflns_Laue_measured_fraction_max 0.647
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6125
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_theta_full        0.863
_diffrn_reflns_theta_max         0.946
_diffrn_reflns_theta_min         0.070
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-ED
_diffrn_measured_fraction_theta_full 0.649
_diffrn_measured_fraction_theta_max 0.647
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  60.00   0.15    0.15    --    0.00   0.00   0.00  800
;
_diffrn_measurement_device       'electron diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy-ED, HyPix-ED, electron source at 200keV'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0014559000
_diffrn_orient_matrix_UB_12      -0.0000496000
_diffrn_orient_matrix_UB_13      -0.0011348000
_diffrn_orient_matrix_UB_21      0.0001789000
_diffrn_orient_matrix_UB_22      -0.0050490000
_diffrn_orient_matrix_UB_23      -0.0000802000
_diffrn_orient_matrix_UB_31      -0.0015536000
_diffrn_orient_matrix_UB_32      -0.0005580000
_diffrn_orient_matrix_UB_33      0.0008541000
_diffrn_radiation_monochromator  'transmission electron microscope'
_diffrn_radiation_probe          electron
_diffrn_radiation_type           'transmission electron microscope'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'transmission electron microscope'
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.770
_reflns_Friedel_fraction_max     0.750
_reflns_number_gt                1245
_reflns_number_total             3407
_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 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.105a 64-bit (release 11-01-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac7-002 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-002 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       9405(20)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     259
_refine_ls_R_factor_all          0.2544
_refine_ls_R_factor_gt           0.1854
_refine_ls_restrained_S_all      1.144
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4603
_refine_ls_wR_factor_ref         0.5176
_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, All N(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C016(H016), C020(H020)
3.b Secondary CH2 refined with riding coordinates:
 C019(H01A,H01B), C030(H03A,H03B)
3.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C011(H011), C014(H014), C015(H015), C021(H021), N022(H022),
 C026(H026), C025(H025), C027(H027), C028(H028)
3.d Fitted pentagon refined as free rotating group:
 C023(N022,C026,C032,C018)
3.e Idealised Me refined as rotating group:
 N009(H00A,H00B,H00C), N012(H01C,H01D,H01E)
;
_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
C001 C 0.931(3) -0.076(5) 0.257(2) 0.090(7) Uani 1 1 d . . . . .
O002 O 0.522(2) 0.691(4) 0.5928(17) 0.077(6) Uani 1 1 d . . . . .
C003 C 0.552(3) 0.560(4) 0.6445(19) 0.074(6) Uani 1 1 d . . . . .
C004 C 0.864(2) 0.429(4) 0.3771(19) 0.071(6) Uani 1 1 d . . . . .
C005 C 0.841(3) 0.271(4) 0.323(2) 0.076(6) Uani 1 1 d . . . . .
O006 O 0.7778(19) 0.547(3) 0.5786(14) 0.068(5) Uani 1 1 d . . . . .
N007 N 1.007(3) 0.176(4) 0.3698(19) 0.088(7) Uani 1 1 d . . . . .
H007 H 1.071961 0.097334 0.379201 0.106 Uiso 1 1 calc R U . . .
C008 C 0.752(2) 0.399(3) 0.5224(17) 0.068(6) Uani 1 1 d . . . . .
N009 N 0.627(2) 0.741(3) 0.4665(18) 0.069(7) Uani 1 1 d . . . . .
H00A H 0.599269 0.718232 0.510821 0.083 Uiso 1 1 calc R U . . .
H00B H 0.570396 0.745547 0.429550 0.083 Uiso 1 1 calc R U . . .
H00C H 0.665988 0.895298 0.467102 0.083 Uiso 1 1 calc R U . . .
O010 O 0.763(3) 0.155(3) 0.526(2) 0.104(10) Uani 1 1 d . . . . .
C011 C 0.557(3) 1.394(5) 0.947(2) 0.094(9) Uani 1 1 d . . . . .
H011 H 0.491826 1.492597 0.953957 0.113 Uiso 1 1 calc R U . . .
N012 N 0.686(2) 0.912(3) 0.6669(16) 0.070(7) Uani 1 1 d . . . . .
H01C H 0.707284 0.875069 0.621408 0.084 Uiso 1 1 calc R U . . .
H01D H 0.745374 0.972174 0.697109 0.084 Uiso 1 1 calc R U . . .
H01E H 0.631986 1.039205 0.662506 0.084 Uiso 1 1 calc R U . . .
O013 O 0.526(2) 0.326(3) 0.6566(18) 0.084(8) Uani 1 1 d . . . . .
C014 C 0.653(3) 1.444(5) 0.993(2) 0.089(8) Uani 1 1 d . . . . .
H014 H 0.654845 1.580741 1.029589 0.107 Uiso 1 1 calc R U . . .
C015 C 0.969(3) 0.372(5) 0.410(2) 0.083(7) Uani 1 1 d . . . . .
H015 H 1.007493 0.455302 0.452118 0.100 Uiso 1 1 calc R U . . .
C016 C 0.644(2) 0.681(4) 0.698(2) 0.075(6) Uani 1 1 d . . . . .
H016 H 0.704630 0.549804 0.710433 0.090 Uiso 1 1 calc R U . . .
C017 C 0.928(3) 0.113(4) 0.311(2) 0.082(7) Uani 1 1 d . . . . .
C019 C 0.790(2) 0.631(3) 0.4077(17) 0.069(7) Uani 1 1 d . . . . .
H01A H 0.752412 0.733590 0.365649 0.083 Uiso 1 1 calc R U . . .
H01B H 0.837499 0.756671 0.438898 0.083 Uiso 1 1 calc R U . . .
C020 C 0.701(2) 0.523(4) 0.4540(16) 0.061(5) Uani 1 1 d . . . . .
H020 H 0.656685 0.384480 0.424053 0.073 Uiso 1 1 calc R U . . .
C021 C 0.553(3) 1.206(4) 0.893(2) 0.089(8) Uani 1 1 d . . . . .
H021 H 0.484725 1.180351 0.862675 0.107 Uiso 1 1 calc R U . . .
C023 C 0.7375(17) 1.098(3) 0.9311(11) 0.082(6) Uani 1 1 d G . . . .
N022 N 0.8245(14) 0.922(3) 0.9108(12) 0.082(6) Uani 1 1 d G . . . .
H022 H 0.892059 0.908908 0.933655 0.099 Uiso 1 1 calc R U . . .
C026 C 0.7805(17) 0.773(3) 0.8460(12) 0.089(8) Uani 1 1 d G . . . .
H026 H 0.819570 0.642752 0.820867 0.107 Uiso 1 1 calc R U . . .
C032 C 0.6662(16) 0.856(4) 0.8263(12) 0.081(6) Uani 1 1 d G . . . .
C018 C 0.6396(14) 1.057(3) 0.8789(13) 0.088(7) Uani 1 1 d G . . . .
C024 C 0.745(3) 1.293(4) 0.986(2) 0.083(7) Uani 1 1 d . . . . .
C025 C 0.839(3) -0.090(5) 0.207(2) 0.098(8) Uani 1 1 d . . . . .
H025 H 0.839582 -0.199895 0.164612 0.118 Uiso 1 1 calc R U . . .
C027 C 0.744(3) 0.242(4) 0.269(2) 0.090(7) Uani 1 1 d . . . . .
H027 H 0.681520 0.355122 0.269435 0.108 Uiso 1 1 calc R U . . .
C028 C 0.746(3) 0.052(6) 0.218(2) 0.107(10) Uani 1 1 d . . . . .
H028 H 0.678578 0.012678 0.188125 0.129 Uiso 1 1 calc R U . . .
C029 C 0.851(3) 1.353(7) 1.031(3) 0.099(9) Uani 1 1 d . . . . .
C030 C 0.588(3) 0.766(5) 0.769(2) 0.081(7) Uani 1 1 d . . . . .
H03A H 0.533242 0.908023 0.755537 0.097 Uiso 1 1 calc R U . . .
H03B H 0.547430 0.612022 0.786919 0.097 Uiso 1 1 calc R U . . .
C1 C 1.027(3) -0.226(5) 0.257(2) 0.098(10) Uani 1 1 d . . . . .
N2 N 1.113(3) -0.324(5) 0.253(2) 0.106(11) Uani 1 1 d . . . . .
N15 N 0.940(3) 1.384(7) 1.065(3) 0.115(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C001 C017 1.33(5) . ?
C001 C025 1.33(5) . ?
C001 C1 1.35(5) . ?
O002 C003 1.15(4) . ?
C003 O013 1.22(3) . ?
C003 C016 1.48(5) . ?
C004 C005 1.25(5) . ?
C004 C015 1.35(4) . ?
C004 C019 1.47(3) . ?
C005 C017 1.33(4) . ?
C005 C027 1.42(5) . ?
O006 C008 1.25(4) . ?
N007 H007 0.8600 . ?
N007 C015 1.31(4) . ?
N007 C017 1.37(5) . ?
C008 O010 1.21(3) . ?
C008 C020 1.44(4) . ?
N009 H00A 0.8900 . ?
N009 H00B 0.8900 . ?
N009 H00C 0.8900 . ?
N009 C020 1.41(3) . ?
C011 H011 0.9300 . ?
C011 C014 1.35(5) . ?
C011 C021 1.34(5) . ?
N012 H01C 0.8900 . ?
N012 H01D 0.8900 . ?
N012 H01E 0.8900 . ?
N012 C016 1.38(3) . ?
C014 H014 0.9300 . ?
C014 C024 1.34(4) . ?
C015 H015 0.9300 . ?
C016 H016 0.9800 . ?
C016 C030 1.54(4) . ?
C019 H01A 0.9700 . ?
C019 H01B 0.9700 . ?
C019 C020 1.50(3) . ?
C020 H020 0.9800 . ?
C021 H021 0.9300 . ?
C021 C018 1.30(3) . ?
C023 N022 1.4200 . ?
C023 C018 1.4200 . ?
C023 C024 1.37(3) . ?
N022 H022 0.8600 . ?
N022 C026 1.4200 . ?
C026 H026 0.9300 . ?
C026 C032 1.4200 . ?
C032 C018 1.4200 . ?
C032 C030 1.38(4) . ?
C024 C029 1.44(6) . ?
C025 H025 0.9300 . ?
C025 C028 1.34(5) . ?
C027 H027 0.9300 . ?
C027 C028 1.30(5) . ?
C028 H028 0.9300 . ?
C029 N15 1.17(6) . ?
C030 H03A 0.9700 . ?
C030 H03B 0.9700 . ?
C1 N2 1.14(5) . ?

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
C017 C001 C025 115(3) . . ?
C017 C001 C1 118(4) . . ?
C025 C001 C1 127(3) . . ?
O002 C003 O013 127(4) . . ?
O002 C003 C016 115(2) . . ?
O013 C003 C016 117(3) . . ?
C005 C004 C015 109(3) . . ?
C005 C004 C019 128(3) . . ?
C015 C004 C019 123(3) . . ?
C004 C005 C017 112(4) . . ?
C004 C005 C027 133(3) . . ?
C017 C005 C027 114(3) . . ?
C015 N007 H007 125.0 . . ?
C015 N007 C017 110(3) . . ?
C017 N007 H007 125.0 . . ?
O006 C008 C020 118(2) . . ?
O010 C008 O006 122(3) . . ?
O010 C008 C020 120(2) . . ?
H00A N009 H00B 109.5 . . ?
H00A N009 H00C 109.5 . . ?
H00B N009 H00C 109.5 . . ?
C020 N009 H00A 109.5 . . ?
C020 N009 H00B 109.5 . . ?
C020 N009 H00C 109.5 . . ?
C014 C011 H011 119.0 . . ?
C021 C011 H011 119.0 . . ?
C021 C011 C014 122(3) . . ?
H01C N012 H01D 109.5 . . ?
H01C N012 H01E 109.5 . . ?
H01D N012 H01E 109.5 . . ?
C016 N012 H01C 109.5 . . ?
C016 N012 H01D 109.5 . . ?
C016 N012 H01E 109.5 . . ?
C011 C014 H014 120.7 . . ?
C024 C014 C011 119(3) . . ?
C024 C014 H014 120.7 . . ?
C004 C015 H015 127.2 . . ?
N007 C015 C004 106(3) . . ?
N007 C015 H015 127.2 . . ?
C003 C016 H016 110.6 . . ?
C003 C016 C030 107(2) . . ?
N012 C016 C003 111(3) . . ?
N012 C016 H016 110.6 . . ?
N012 C016 C030 107(2) . . ?
C030 C016 H016 110.6 . . ?
C001 C017 N007 129(3) . . ?
C005 C017 C001 128(4) . . ?
C005 C017 N007 103(3) . . ?
C004 C019 H01A 108.3 . . ?
C004 C019 H01B 108.3 . . ?
C004 C019 C020 115.9(17) . . ?
H01A C019 H01B 107.4 . . ?
C020 C019 H01A 108.3 . . ?
C020 C019 H01B 108.3 . . ?
C008 C020 C019 111(2) . . ?
C008 C020 H020 108.4 . . ?
N009 C020 C008 114(2) . . ?
N009 C020 C019 106.9(19) . . ?
N009 C020 H020 108.4 . . ?
C019 C020 H020 108.4 . . ?
C011 C021 H021 118.1 . . ?
C018 C021 C011 124(4) . . ?
C018 C021 H021 118.1 . . ?
N022 C023 C018 108.0 . . ?
C024 C023 N022 128.1(19) . . ?
C024 C023 C018 123.6(19) . . ?
C023 N022 H022 126.0 . . ?
C023 N022 C026 108.0 . . ?
C026 N022 H022 126.0 . . ?
N022 C026 H026 126.0 . . ?
N022 C026 C032 108.0 . . ?
C032 C026 H026 126.0 . . ?
C026 C032 C018 108.0 . . ?
C030 C032 C026 129.5(18) . . ?
C030 C032 C018 122.5(18) . . ?
C021 C018 C023 114(2) . . ?
C021 C018 C032 138(2) . . ?
C023 C018 C032 108.0 . . ?
C014 C024 C023 118(4) . . ?
C014 C024 C029 120(3) . . ?
C023 C024 C029 122(3) . . ?
C001 C025 H025 119.8 . . ?
C001 C025 C028 120(3) . . ?
C028 C025 H025 119.8 . . ?
C005 C027 H027 120.9 . . ?
C028 C027 C005 118(3) . . ?
C028 C027 H027 120.9 . . ?
C025 C028 H028 118.3 . . ?
C027 C028 C025 123(4) . . ?
C027 C028 H028 118.3 . . ?
N15 C029 C024 175(4) . . ?
C016 C030 H03A 109.0 . . ?
C016 C030 H03B 109.0 . . ?
C032 C030 C016 113(2) . . ?
C032 C030 H03A 109.0 . . ?
C032 C030 H03B 109.0 . . ?
H03A C030 H03B 107.8 . . ?
N2 C1 C001 171(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C001 C025 C028 C027 12(6) . . . . ?
O002 C003 C016 N012 -10(3) . . . . ?
O002 C003 C016 C030 107(3) . . . . ?
C003 C016 C030 C032 174(2) . . . . ?
C004 C005 C017 C001 -180(3) . . . . ?
C004 C005 C017 N007 5(3) . . . . ?
C004 C005 C027 C028 -180(4) . . . . ?
C004 C019 C020 C008 65(3) . . . . ?
C004 C019 C020 N009 -170(3) . . . . ?
C005 C004 C015 N007 2(3) . . . . ?
C005 C004 C019 C020 75(4) . . . . ?
C005 C027 C028 C025 -10(6) . . . . ?
O006 C008 C020 N009 -35(3) . . . . ?
O006 C008 C020 C019 85(3) . . . . ?
O010 C008 C020 N009 140(3) . . . . ?
O010 C008 C020 C019 -100(3) . . . . ?
C011 C014 C024 C023 1(4) . . . . ?
C011 C014 C024 C029 176(3) . . . . ?
C011 C021 C018 C023 4(4) . . . . ?
C011 C021 C018 C032 -177(2) . . . . ?
N012 C016 C030 C032 -68(3) . . . . ?
O013 C003 C016 N012 164(2) . . . . ?
O013 C003 C016 C030 -80(3) . . . . ?
C014 C011 C021 C018 0(5) . . . . ?
C015 C004 C005 C017 -5(3) . . . . ?
C015 C004 C005 C027 -179(3) . . . . ?
C015 C004 C019 C020 -99(3) . . . . ?
C015 N007 C017 C001 -179(3) . . . . ?
C015 N007 C017 C005 -4(3) . . . . ?
C017 C001 C025 C028 -9(5) . . . . ?
C017 C005 C027 C028 6(4) . . . . ?
C017 N007 C015 C004 2(3) . . . . ?
C019 C004 C005 C017 -180(2) . . . . ?
C019 C004 C005 C027 6(5) . . . . ?
C019 C004 C015 N007 177(2) . . . . ?
C021 C011 C014 C024 -3(5) . . . . ?
C023 N022 C026 C032 0.0 . . . . ?
N022 C023 C018 C021 179(2) . . . . ?
N022 C023 C018 C032 0.0 . . . . ?
N022 C023 C024 C014 177(2) . . . . ?
N022 C023 C024 C029 2(4) . . . . ?
N022 C026 C032 C018 0.0 . . . . ?
N022 C026 C032 C030 -179(3) . . . . ?
C026 C032 C018 C021 -179(3) . . . . ?
C026 C032 C018 C023 0.0 . . . . ?
C026 C032 C030 C016 -33(3) . . . . ?
C018 C023 N022 C026 0.0 . . . . ?
C018 C023 C024 C014 4(4) . . . . ?
C018 C023 C024 C029 -171(2) . . . . ?
C018 C032 C030 C016 148.4(18) . . . . ?
C024 C023 N022 C026 -174(3) . . . . ?
C024 C023 C018 C021 -6(3) . . . . ?
C024 C023 C018 C032 175(3) . . . . ?
C025 C001 C017 C005 5(5) . . . . ?
C025 C001 C017 N007 179(3) . . . . ?
C027 C005 C017 C001 -4(4) . . . . ?
C027 C005 C017 N007 -179(2) . . . . ?
C030 C032 C018 C021 0(3) . . . . ?
C030 C032 C018 C023 179(2) . . . . ?
C1 C001 C017 C005 -176(3) . . . . ?
C1 C001 C017 N007 -3(5) . . . . ?
C1 C001 C025 C028 173(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.149
_oxdiff_exptl_absorpt_empirical_full_min 0.546
# start Validation Reply Form
_vrf_PLAT084_1108_1              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.52 Report
RESPONSE: Multiple scattering effects
;
_vrf_PLAT035_1108_1              
;
PROBLEM: _chemical_absolute_configuration Info  Not Given     Please Do !
RESPONSE: The absolute configuration has not been determined by dynamical refinement.
The absolute configuration has already been determined by other methods.
;
_vrf_PLAT082_1108_1              
;
PROBLEM: High R1 Value ..................................       0.19 Report
RESPONSE: Multiple scattering effects
;
_vrf_PLAT149_1108_1              
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.17 Degree
RESPONSE: Multiple scattering effects
;
_vrf_PLAT340_1108_1              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0475 Ang.
RESPONSE: Multiple scattering effects
;
# end Validation Reply Form

####################################################################### 
# 
# 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_tyh237_entry11_dry
_database_code_depnum_ccdc_archive 'CCDC 2419168'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2025-01-23 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2024-12-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N3 O2'
_chemical_formula_sum            'C10 H11 N3 O2'
_chemical_formula_weight         205.22
_chemical_absolute_configuration rm
_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      tetragonal
_space_group_IT_number           79
_space_group_name_H-M_alt        'I 4'
_space_group_name_Hall           'I 4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   18.69560(8)
_cell_length_b                   18.69560(8)
_cell_length_c                   5.95062(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2079.89(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5593
_cell_measurement_temperature    223
_cell_measurement_theta_max      71.18
_cell_measurement_theta_min      4.73
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.651
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/H2O'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6721
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.652
_diffrn_reflns_theta_min         4.731
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                1942
_reflns_number_total             1974
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.119
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 838 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1974
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+0.3361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0619
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C6(H6), C5(H5)
2.d Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C)
;
_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 0.10061(6) 0.66655(5) 0.58659(19) 0.0305(3) Uani 1 1 d . . . . .
O1 O 0.11704(6) 0.55634(6) 0.71803(19) 0.0321(3) Uani 1 1 d . . . . .
N1 N 0.31713(7) 0.72175(7) 0.2898(2) 0.0302(3) Uani 1 1 d . . . . .
H1 H 0.333777 0.761796 0.236746 0.036 Uiso 1 1 calc R U . . .
N3 N 0.09068(6) 0.62469(6) 0.1566(2) 0.0245(3) Uani 1 1 d . . . . .
H3A H 0.102385 0.611176 0.016220 0.029 Uiso 1 1 calc R U . . .
H3B H 0.107854 0.668872 0.183095 0.029 Uiso 1 1 calc R U . . .
H3C H 0.042769 0.624944 0.171291 0.029 Uiso 1 1 calc R U . . .
N2 N 0.38519(7) 0.71577(8) 0.6320(3) 0.0337(3) Uani 1 1 d . . . . .
C10 C 0.11204(7) 0.60166(7) 0.5622(2) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.25127(7) 0.62122(8) 0.3179(3) 0.0255(3) Uani 1 1 d . . . . .
C3 C 0.29669(8) 0.62643(8) 0.5112(3) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.33723(8) 0.69011(8) 0.4864(3) 0.0266(3) Uani 1 1 d . . . . .
C1 C 0.26598(8) 0.67944(8) 0.1897(3) 0.0293(3) Uani 1 1 d . . . . .
H1A H 0.244136 0.689531 0.051026 0.035 Uiso 1 1 calc R U . . .
C8 C 0.20158(8) 0.55999(8) 0.2666(3) 0.0276(3) Uani 1 1 d . . . . .
H8A H 0.217510 0.518013 0.351531 0.033 Uiso 1 1 calc R U . . .
H8B H 0.205720 0.548407 0.106468 0.033 Uiso 1 1 calc R U . . .
C9 C 0.12216(7) 0.57358(7) 0.3209(3) 0.0230(3) Uani 1 1 d . . . . .
H9 H 0.096263 0.527591 0.307463 0.028 Uiso 1 1 calc R U . . .
C4 C 0.31103(8) 0.58434(8) 0.6974(3) 0.0312(3) Uani 1 1 d . . . . .
H4 H 0.286384 0.541221 0.721907 0.037 Uiso 1 1 calc R U . . .
C6 C 0.39693(9) 0.67327(10) 0.8101(3) 0.0371(4) Uani 1 1 d . . . . .
H6 H 0.430349 0.688592 0.917909 0.045 Uiso 1 1 calc R U . . .
C5 C 0.36281(9) 0.60787(10) 0.8459(3) 0.0374(4) Uani 1 1 d . . . . .
H5 H 0.375040 0.579772 0.971109 0.045 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 C10 1.2402(18) . ?
O1 C10 1.2595(19) . ?
N1 H1 0.8700 . ?
N1 C7 1.364(2) . ?
N1 C1 1.377(2) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N3 H3C 0.9000 . ?
N3 C9 1.4882(19) . ?
N2 C7 1.336(2) . ?
N2 C6 1.343(3) . ?
C10 C9 1.541(2) . ?
C2 C3 1.433(2) . ?
C2 C1 1.357(2) . ?
C2 C8 1.505(2) . ?
C3 C7 1.419(2) . ?
C3 C4 1.385(2) . ?
C1 H1A 0.9400 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 C9 1.5406(19) . ?
C9 H9 0.9900 . ?
C4 H4 0.9400 . ?
C4 C5 1.383(3) . ?
C6 H6 0.9400 . ?
C6 C5 1.395(3) . ?
C5 H5 0.9400 . ?

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
C7 N1 H1 125.9 . . ?
C7 N1 C1 108.25(12) . . ?
C1 N1 H1 125.9 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C9 N3 H3A 109.5 . . ?
C9 N3 H3B 109.5 . . ?
C9 N3 H3C 109.5 . . ?
C7 N2 C6 114.16(14) . . ?
O2 C10 O1 125.79(14) . . ?
O2 C10 C9 117.61(13) . . ?
O1 C10 C9 116.60(12) . . ?
C3 C2 C8 125.47(14) . . ?
C1 C2 C3 106.05(13) . . ?
C1 C2 C8 128.37(15) . . ?
C7 C3 C2 106.85(13) . . ?
C4 C3 C2 135.89(14) . . ?
C4 C3 C7 117.17(15) . . ?
N1 C7 C3 107.83(14) . . ?
N2 C7 N1 125.84(14) . . ?
N2 C7 C3 126.31(15) . . ?
N1 C1 H1A 124.5 . . ?
C2 C1 N1 111.01(14) . . ?
C2 C1 H1A 124.5 . . ?
C2 C8 H8A 108.5 . . ?
C2 C8 H8B 108.5 . . ?
C2 C8 C9 115.26(12) . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
N3 C9 C10 110.17(11) . . ?
N3 C9 C8 110.43(12) . . ?
N3 C9 H9 108.1 . . ?
C10 C9 C8 111.73(12) . . ?
C10 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.77(14) . . ?
C5 C4 H4 121.1 . . ?
N2 C6 H6 117.8 . . ?
N2 C6 C5 124.34(17) . . ?
C5 C6 H6 117.8 . . ?
C4 C5 C6 120.10(17) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?

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
O2 C10 C9 N3 -20.49(17) . . . . ?
O2 C10 C9 C8 102.65(14) . . . . ?
O1 C10 C9 N3 160.33(12) . . . . ?
O1 C10 C9 C8 -76.52(15) . . . . ?
N2 C6 C5 C4 -2.7(3) . . . . ?
C2 C3 C7 N1 0.31(15) . . . . ?
C2 C3 C7 N2 178.65(14) . . . . ?
C2 C3 C4 C5 176.98(16) . . . . ?
C2 C8 C9 N3 72.15(17) . . . . ?
C2 C8 C9 C10 -50.85(18) . . . . ?
C3 C2 C1 N1 -0.68(17) . . . . ?
C3 C2 C8 C9 101.25(17) . . . . ?
C3 C4 C5 C6 2.2(2) . . . . ?
C7 N1 C1 C2 0.90(17) . . . . ?
C7 N2 C6 C5 -0.2(2) . . . . ?
C7 C3 C4 C5 0.9(2) . . . . ?
C1 N1 C7 N2 -179.07(14) . . . . ?
C1 N1 C7 C3 -0.72(16) . . . . ?
C1 C2 C3 C7 0.22(16) . . . . ?
C1 C2 C3 C4 -176.17(17) . . . . ?
C1 C2 C8 C9 -83.2(2) . . . . ?
C8 C2 C3 C7 176.58(13) . . . . ?
C8 C2 C3 C4 0.2(3) . . . . ?
C8 C2 C1 N1 -176.90(14) . . . . ?
C4 C3 C7 N1 177.49(13) . . . . ?
C4 C3 C7 N2 -4.2(2) . . . . ?
C6 N2 C7 N1 -178.19(15) . . . . ?
C6 N2 C7 C3 3.8(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.623 136.7 40.8 ?
2 0.500 0.500 -0.144 136.7 40.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_tyh237
_database_code_depnum_ccdc_archive 'CCDC 2419169'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2025-01-23 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H11 N3 O2'
_chemical_formula_moiety         'C10 H11 N3 O2'
_chemical_formula_weight         205.22
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.02963(16)
_cell_length_b                   5.82382(10)
_cell_length_c                   9.72260(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.326(2)
_cell_angle_gamma                90.0000
_cell_volume                     472.955(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4209
_cell_measurement_theta_min      4.92
_cell_measurement_theta_max      73.04
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.015
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             216.00
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.590
_exptl_absorpt_correction_T_max  0.987

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            4931
_diffrn_reflns_av_R_equivalents  0.1355
_diffrn_reflns_theta_max         68.128
_diffrn_reflns_theta_min         4.917
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1695
_reflns_number_gt                1622
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.963

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1837
_refine_ls_wR_factor_gt          0.1823
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1695
_refine_ls_number_parameters     152
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1420P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.2(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9659(4) 0.2572(6) 0.7619(4) 0.0330(8) Uani 1 1 d . . . . .
O2 O 0.8667(3) 0.4072(5) 0.5329(3) 0.0264(8) Uani 1 1 d . . . . .
N1 N 0.4363(4) 0.7212(7) 0.6222(4) 0.0286(9) Uani 1 1 d . . . . .
N2 N 0.3254(5) 0.3949(8) 0.7000(5) 0.0347(10) Uani 1 1 d . . . . .
N3 N 0.9351(4) 0.8357(6) 0.6205(4) 0.0230(8) Uani 1 1 d . . . . .
C1 C 0.5872(5) 0.8117(8) 0.6607(5) 0.0262(10) Uani 1 1 d . . . . .
H1 H 0.6107 0.9482 0.6214 0.031 Uiso 1 1 calc R U . . .
C2 C 0.6989(5) 0.6768(8) 0.7638(4) 0.0216(9) Uani 1 1 d . . . . .
C3 C 0.6120(5) 0.4908(7) 0.7943(4) 0.0215(9) Uani 1 1 d . . . . .
C4 C 0.6478(5) 0.3002(8) 0.8870(4) 0.0259(10) Uani 1 1 d . . . . .
H4 H 0.7543 0.2648 0.9476 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5234(6) 0.1640(9) 0.8881(5) 0.0316(10) Uani 1 1 d . . . . .
H5 H 0.5439 0.0362 0.9517 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3665(6) 0.2173(9) 0.7938(5) 0.0348(11) Uani 1 1 d . . . . .
H7 H 0.2841 0.1211 0.7967 0.042 Uiso 1 1 calc R U . . .
C8 C 0.4475(5) 0.5266(8) 0.7048(5) 0.0250(9) Uani 1 1 d . . . . .
C9 C 0.8761(5) 0.7156(8) 0.8383(4) 0.0230(9) Uani 1 1 d . . . . .
H9A H 0.9176 0.6196 0.9277 0.028 Uiso 1 1 calc R U . . .
H9B H 0.8948 0.8763 0.8701 0.028 Uiso 1 1 calc R U . . .
C10 C 0.9702(4) 0.6621(7) 0.7401(4) 0.0205(9) Uani 1 1 d . . . . .
H10 H 1.0859 0.6693 0.8026 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9318(4) 0.4196(7) 0.6738(5) 0.0211(9) Uani 1 1 d . . . . .
H2 H 0.340(7) 0.796(11) 0.562(6) 0.029(13) Uiso 1 1 d . . . . .
H3 H 0.838(8) 0.805(12) 0.542(7) 0.035(15) Uiso 1 1 d . . . . .
H6 H 0.939(8) 0.981(13) 0.670(7) 0.039(16) Uiso 1 1 d . . . . .
H8 H 1.016(8) 0.836(12) 0.573(7) 0.043(16) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.234(6) . ?
O2 C11 1.271(5) . ?
N1 C8 1.370(6) . ?
N1 C1 1.374(6) . ?
N1 H2 0.95(6) . ?
N2 C8 1.329(6) . ?
N2 C7 1.335(7) . ?
N3 C10 1.481(5) . ?
N3 H3 0.94(6) . ?
N3 H6 0.96(8) . ?
N3 H8 1.01(7) . ?
C1 C2 1.368(6) . ?
C1 H1 0.9400 . ?
C2 C3 1.433(6) . ?
C2 C9 1.502(6) . ?
C3 C4 1.389(6) . ?
C3 C8 1.423(6) . ?
C4 C5 1.378(7) . ?
C4 H4 0.9400 . ?
C5 C7 1.399(7) . ?
C5 H5 0.9400 . ?
C7 H7 0.9400 . ?
C9 C10 1.532(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.536(6) . ?
C10 H10 0.9900 . ?

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 N1 C1 108.3(4) . . ?
C8 N1 H2 126(4) . . ?
C1 N1 H2 125(4) . . ?
C8 N2 C7 114.3(4) . . ?
C10 N3 H3 111(4) . . ?
C10 N3 H6 105(4) . . ?
H3 N3 H6 114(6) . . ?
C10 N3 H8 113(4) . . ?
H3 N3 H8 105(5) . . ?
H6 N3 H8 109(5) . . ?
C2 C1 N1 110.9(4) . . ?
C2 C1 H1 124.5 . . ?
N1 C1 H1 124.5 . . ?
C1 C2 C3 106.1(4) . . ?
C1 C2 C9 128.4(4) . . ?
C3 C2 C9 125.5(4) . . ?
C4 C3 C8 116.4(4) . . ?
C4 C3 C2 136.7(4) . . ?
C8 C3 C2 106.8(4) . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C7 119.5(5) . . ?
C4 C5 H5 120.2 . . ?
C7 C5 H5 120.2 . . ?
N2 C7 C5 124.7(4) . . ?
N2 C7 H7 117.7 . . ?
C5 C7 H7 117.7 . . ?
N2 C8 N1 125.5(4) . . ?
N2 C8 C3 126.6(4) . . ?
N1 C8 C3 107.9(4) . . ?
C2 C9 C10 114.2(3) . . ?
C2 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C2 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N3 C10 C9 110.3(3) . . ?
N3 C10 C11 110.6(3) . . ?
C9 C10 C11 111.0(3) . . ?
N3 C10 H10 108.3 . . ?
C9 C10 H10 108.3 . . ?
C11 C10 H10 108.3 . . ?
O1 C11 O2 126.6(4) . . ?
O1 C11 C10 117.1(3) . . ?
O2 C11 C10 116.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 1.9(5) . . . . ?
N1 C1 C2 C3 -1.0(5) . . . . ?
N1 C1 C2 C9 -178.3(4) . . . . ?
C1 C2 C3 C4 -178.2(5) . . . . ?
C9 C2 C3 C4 -0.9(7) . . . . ?
C1 C2 C3 C8 -0.2(4) . . . . ?
C9 C2 C3 C8 177.1(4) . . . . ?
C8 C3 C4 C5 -1.2(6) . . . . ?
C2 C3 C4 C5 176.7(5) . . . . ?
C3 C4 C5 C7 1.7(6) . . . . ?
C8 N2 C7 C5 -1.7(7) . . . . ?
C4 C5 C7 N2 -0.2(7) . . . . ?
C7 N2 C8 N1 -178.6(4) . . . . ?
C7 N2 C8 C3 2.3(7) . . . . ?
C1 N1 C8 N2 178.7(4) . . . . ?
C1 N1 C8 C3 -2.0(5) . . . . ?
C4 C3 C8 N2 -0.9(6) . . . . ?
C2 C3 C8 N2 -179.3(4) . . . . ?
C4 C3 C8 N1 179.9(3) . . . . ?
C2 C3 C8 N1 1.4(4) . . . . ?
C1 C2 C9 C10 -76.6(6) . . . . ?
C3 C2 C9 C10 106.7(4) . . . . ?
C2 C9 C10 N3 70.2(5) . . . . ?
C2 C9 C10 C11 -52.6(5) . . . . ?
N3 C10 C11 O1 175.2(4) . . . . ?
C9 C10 C11 O1 -62.1(4) . . . . ?
N3 C10 C11 O2 -5.3(5) . . . . ?
C9 C10 C11 O2 117.4(4) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H2 O2 . . 2_656 2.793(4) 0.95(5) 1.85(6) 169(6) no
N3 H3 O2 . . . 2.633(5) 0.94(5) 2.34(7) 98(5) no
N3 H6 O1 . . 1_565 2.775(5) 0.96(8) 1.81(8) 174(7) no
N3 H8 O2 . . 2_756 2.762(6) 1.01(8) 1.78(8) 165(6) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH3CN/H2O'
####################################################################### 
# 
# 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_tyh184
_database_code_depnum_ccdc_archive 'CCDC 2419170'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2025-01-23 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT353_tyh184              
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N5       - H5B      .       1.13 Ang.
RESPONSE: This is due to hydrogen bonding between H5B and O3.
;
# Added during the CSD deposition process: Thursday 23 January 2025 05:56 AM
# end Validation Reply Form

_audit_creation_date             2023-12-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3 O2, C11 H12 N2 O2'
_chemical_formula_sum            'C23 H23 N5 O4'
_chemical_formula_weight         433.46
_chemical_absolute_configuration rmad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.43660(10)
_cell_length_b                   5.76640(10)
_cell_length_c                   19.6310(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.2100(10)
_cell_angle_gamma                90
_cell_volume                     1047.84(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6717
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      74.57
_cell_measurement_theta_min      5.92
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.692
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16079
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.223
_diffrn_reflns_theta_min         4.593
_diffrn_ambient_temperature      223.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                3558
_reflns_number_total             4013
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.060
_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)+(0.0401P)²+0.1410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0922
_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 Ternary CH refined with riding coordinates:
 C10(H10), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4A), N1(H1), C4(H4), C1(H1A), C13(H13), C5(H5), C6(H6), C16(H16),
 C19(H19), C17(H17), C18(H18)
;
_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
O2 O 0.61984(17) 0.3941(3) 0.51668(8) 0.0334(5) Uani 1 1 d . . . . .
O4 O 0.88293(17) 0.7187(3) 0.48018(9) 0.0321(4) Uani 1 1 d . . . . .
O3 O 0.7615(2) 0.8609(4) 0.38045(10) 0.0457(5) Uani 1 1 d . . . . .
O1 O 0.7383(2) 0.2557(4) 0.61784(10) 0.0449(5) Uani 1 1 d . . . . .
N5 N 0.8346(3) 0.2795(4) 0.43931(12) 0.0309(5) Uani 1 1 d . . . . .
N2 N 0.6684(3) 0.8360(4) 0.55624(11) 0.0288(5) Uani 1 1 d . . . . .
N4 N 0.9036(3) 0.8363(5) 0.19207(13) 0.0516(7) Uani 1 1 d . . . . .
H4A H 0.931069 0.958106 0.171882 0.062 Uiso 1 1 calc R U . . .
C23 C 0.8202(3) 0.7005(5) 0.41768(14) 0.0287(6) Uani 1 1 d . . . . .
N1 N 0.5854(2) 0.2978(5) 0.80535(11) 0.0407(6) Uani 1 1 d . . . . .
H1 H 0.557863 0.178947 0.826823 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6857(3) 0.6562(5) 0.61158(13) 0.0282(6) Uani 1 1 d . . . . .
H10 H 0.780924 0.677859 0.642526 0.034 Uiso 1 1 calc R U . . .
C3 C 0.7066(3) 0.6141(5) 0.78090(13) 0.0336(6) Uani 1 1 d . . . . .
C20 C 0.7924(3) 0.6934(6) 0.16361(15) 0.0423(7) Uani 1 1 d . . . . .
C2 C 0.5964(3) 0.5597(5) 0.72177(13) 0.0337(6) Uani 1 1 d . . . . .
C11 C 0.6812(3) 0.4154(5) 0.57945(13) 0.0282(6) Uani 1 1 d . . . . .
C9 C 0.5671(3) 0.6886(6) 0.65463(13) 0.0344(6) Uani 1 1 d . . . . .
H9A H 0.557913 0.854168 0.664193 0.041 Uiso 1 1 calc R U . . .
H9B H 0.474694 0.636002 0.627149 0.041 Uiso 1 1 calc R U . . .
C22 C 0.8148(3) 0.4604(5) 0.38436(13) 0.0273(6) Uani 1 1 d . . . . .
H22 H 0.718075 0.439519 0.354687 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8101(3) 0.7888(6) 0.79626(14) 0.0443(8) Uani 1 1 d . . . . .
H4 H 0.818939 0.902156 0.762916 0.053 Uiso 1 1 calc R U . . .
C14 C 0.8960(3) 0.5677(5) 0.27254(13) 0.0359(6) Uani 1 1 d . . . . .
C1 C 0.5256(3) 0.3685(6) 0.73909(13) 0.0379(7) Uani 1 1 d . . . . .
H1A H 0.447386 0.295767 0.709950 0.045 Uiso 1 1 calc R U . . .
C15 C 0.7845(3) 0.5193(6) 0.21331(14) 0.0369(7) Uani 1 1 d . . . . .
C21 C 0.9287(3) 0.4311(5) 0.33872(13) 0.0352(6) Uani 1 1 d . . . . .
H21A H 1.022906 0.479689 0.365280 0.042 Uiso 1 1 calc R U . . .
H21B H 0.935555 0.266518 0.327391 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7761(3) 0.2777(6) 0.94840(14) 0.0520(7) Uani 1 1 d . . . . .
C8 C 0.6961(3) 0.4470(6) 0.83188(13) 0.0370(6) Uani 1 1 d . . . . .
C7 C 0.7867(3) 0.4512(7) 0.89751(14) 0.0448(7) Uani 1 1 d . . . . .
C13 C 0.9653(3) 0.7601(6) 0.25669(16) 0.0452(7) Uani 1 1 d . . . . .
H13 H 1.044232 0.830612 0.285954 0.054 Uiso 1 1 calc R U . . .
N3 N 0.7689(3) 0.1383(6) 0.98870(14) 0.0707(8) Uani 1 1 d . . . . .
C5 C 0.8993(3) 0.7937(7) 0.86075(16) 0.0541(9) Uani 1 1 d . . . . .
H5 H 0.969162 0.911415 0.870957 0.065 Uiso 1 1 calc R U . . .
C6 C 0.8885(3) 0.6295(8) 0.91081(16) 0.0528(9) Uani 1 1 d . . . . .
H6 H 0.950491 0.638007 0.954437 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6817(3) 0.3427(6) 0.19627(15) 0.0443(7) Uani 1 1 d . . . . .
H16 H 0.674389 0.224012 0.228208 0.053 Uiso 1 1 calc R U . . .
C19 C 0.7014(4) 0.6967(7) 0.09897(16) 0.0548(9) Uani 1 1 d . . . . .
H19 H 0.708146 0.814388 0.066605 0.066 Uiso 1 1 calc R U . . .
C17 C 0.5916(3) 0.3457(8) 0.13200(16) 0.0559(9) Uani 1 1 d . . . . .
H17 H 0.522488 0.227709 0.120162 0.067 Uiso 1 1 calc R U . . .
C18 C 0.6015(4) 0.5224(8) 0.08392(17) 0.0603(10) Uani 1 1 d . . . . .
H18 H 0.538227 0.521199 0.040545 0.072 Uiso 1 1 calc R U . . .
H2A H 0.574(3) 0.836(7) 0.5289(14) 0.044(8) Uiso 1 1 d . . . . .
H5A H 0.926(4) 0.287(8) 0.4685(16) 0.056(10) Uiso 1 1 d . . . . .
H5B H 0.814(4) 0.103(9) 0.415(2) 0.079(13) Uiso 1 1 d . . . . .
H2B H 0.737(3) 0.807(6) 0.5247(16) 0.048(8) Uiso 1 1 d . . . . .
H2C H 0.685(3) 0.993(7) 0.5763(15) 0.038(8) Uiso 1 1 d . . . . .
H5C H 0.769(3) 0.307(6) 0.4671(14) 0.039(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
O2 C11 1.262(3) . ?
O4 C23 1.259(3) . ?
O3 C23 1.240(3) . ?
O1 C11 1.244(3) . ?
N5 C22 1.486(4) . ?
N5 H5A 0.94(3) . ?
N5 H5B 1.13(5) . ?
N5 H5C 0.92(3) . ?
N2 C10 1.488(3) . ?
N2 H2A 0.95(3) . ?
N2 H2B 1.00(3) . ?
N2 H2C 0.99(4) . ?
N4 H4A 0.8700 . ?
N4 C20 1.366(4) . ?
N4 C13 1.362(4) . ?
C23 C22 1.528(4) . ?
N1 H1 0.8700 . ?
N1 C1 1.375(3) . ?
N1 C8 1.376(4) . ?
C10 H10 0.9900 . ?
C10 C11 1.522(4) . ?
C10 C9 1.539(3) . ?
C3 C2 1.435(4) . ?
C3 C4 1.395(4) . ?
C3 C8 1.407(4) . ?
C20 C15 1.412(4) . ?
C20 C19 1.387(4) . ?
C2 C9 1.492(4) . ?
C2 C1 1.366(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C22 H22 0.9900 . ?
C22 C21 1.537(3) . ?
C4 H4 0.9400 . ?
C4 C5 1.378(4) . ?
C14 C15 1.435(4) . ?
C14 C21 1.499(4) . ?
C14 C13 1.355(4) . ?
C1 H1A 0.9400 . ?
C15 C16 1.401(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C12 C7 1.431(5) . ?
C12 N3 1.139(4) . ?
C8 C7 1.401(4) . ?
C7 C6 1.396(5) . ?
C13 H13 0.9400 . ?
C5 H5 0.9400 . ?
C5 C6 1.383(5) . ?
C6 H6 0.9400 . ?
C16 H16 0.9400 . ?
C16 C17 1.378(4) . ?
C19 H19 0.9400 . ?
C19 C18 1.371(5) . ?
C17 H17 0.9400 . ?
C17 C18 1.404(6) . ?
C18 H18 0.9400 . ?

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
C22 N5 H5A 112(2) . . ?
C22 N5 H5B 110(2) . . ?
C22 N5 H5C 108(2) . . ?
H5A N5 H5B 111(3) . . ?
H5A N5 H5C 106(2) . . ?
H5B N5 H5C 110(3) . . ?
C10 N2 H2A 112(2) . . ?
C10 N2 H2B 110(2) . . ?
C10 N2 H2C 111.2(18) . . ?
H2A N2 H2B 108(2) . . ?
H2A N2 H2C 107(3) . . ?
H2B N2 H2C 109(3) . . ?
C20 N4 H4A 125.0 . . ?
C13 N4 H4A 125.0 . . ?
C13 N4 C20 110.0(3) . . ?
O4 C23 C22 117.6(2) . . ?
O3 C23 O4 125.7(3) . . ?
O3 C23 C22 116.7(2) . . ?
C1 N1 H1 125.8 . . ?
C1 N1 C8 108.3(3) . . ?
C8 N1 H1 125.8 . . ?
N2 C10 H10 108.5 . . ?
N2 C10 C11 110.0(2) . . ?
N2 C10 C9 109.1(2) . . ?
C11 C10 H10 108.5 . . ?
C11 C10 C9 111.9(2) . . ?
C9 C10 H10 108.5 . . ?
C4 C3 C2 134.4(3) . . ?
C4 C3 C8 119.0(2) . . ?
C8 C3 C2 106.6(2) . . ?
N4 C20 C15 106.6(2) . . ?
N4 C20 C19 131.0(3) . . ?
C19 C20 C15 122.4(3) . . ?
C3 C2 C9 125.9(3) . . ?
C1 C2 C3 106.7(2) . . ?
C1 C2 C9 127.4(2) . . ?
O2 C11 C10 117.6(2) . . ?
O1 C11 O2 125.6(3) . . ?
O1 C11 C10 116.8(2) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C2 C9 C10 113.3(2) . . ?
C2 C9 H9A 108.9 . . ?
C2 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N5 C22 C23 109.7(2) . . ?
N5 C22 H22 108.2 . . ?
N5 C22 C21 110.0(2) . . ?
C23 C22 H22 108.2 . . ?
C23 C22 C21 112.3(2) . . ?
C21 C22 H22 108.2 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C15 C14 C21 126.5(3) . . ?
C13 C14 C15 106.5(3) . . ?
C13 C14 C21 127.0(3) . . ?
N1 C1 H1A 124.9 . . ?
C2 C1 N1 110.1(2) . . ?
C2 C1 H1A 124.9 . . ?
C20 C15 C14 107.1(3) . . ?
C16 C15 C20 118.6(3) . . ?
C16 C15 C14 134.3(3) . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C14 C21 C22 113.5(2) . . ?
C14 C21 H21A 108.9 . . ?
C14 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
N3 C12 C7 179.3(3) . . ?
N1 C8 C3 108.2(2) . . ?
N1 C8 C7 129.9(3) . . ?
C7 C8 C3 121.8(3) . . ?
C8 C7 C12 121.1(3) . . ?
C6 C7 C12 121.5(3) . . ?
C6 C7 C8 117.3(3) . . ?
N4 C13 H13 125.0 . . ?
C14 C13 N4 109.9(3) . . ?
C14 C13 H13 125.0 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C20 C19 H19 121.2 . . ?
C18 C19 C20 117.7(3) . . ?
C18 C19 H19 121.2 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?

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
O4 C23 C22 N5 22.0(3) . . . . ?
O4 C23 C22 C21 -100.7(3) . . . . ?
O3 C23 C22 N5 -157.7(2) . . . . ?
O3 C23 C22 C21 79.6(3) . . . . ?
N5 C22 C21 C14 166.2(2) . . . . ?
N2 C10 C11 O2 -22.5(3) . . . . ?
N2 C10 C11 O1 157.9(2) . . . . ?
N2 C10 C9 C2 -165.0(2) . . . . ?
N4 C20 C15 C14 0.4(3) . . . . ?
N4 C20 C15 C16 -177.7(3) . . . . ?
N4 C20 C19 C18 177.6(3) . . . . ?
C23 C22 C21 C14 -71.3(3) . . . . ?
N1 C8 C7 C12 2.5(5) . . . . ?
N1 C8 C7 C6 -178.2(3) . . . . ?
C3 C2 C9 C10 70.3(4) . . . . ?
C3 C2 C1 N1 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C3 C8 C7 C12 -179.0(3) . . . . ?
C3 C8 C7 C6 0.3(4) . . . . ?
C20 N4 C13 C14 -0.5(3) . . . . ?
C20 C15 C16 C17 -0.4(4) . . . . ?
C20 C19 C18 C17 -0.3(5) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C2 C3 C8 N1 0.1(3) . . . . ?
C2 C3 C8 C7 -178.7(3) . . . . ?
C11 C10 C9 C2 72.9(3) . . . . ?
C9 C10 C11 O2 99.1(3) . . . . ?
C9 C10 C11 O1 -80.6(3) . . . . ?
C9 C2 C1 N1 179.1(3) . . . . ?
C4 C3 C2 C9 2.3(5) . . . . ?
C4 C3 C2 C1 -178.0(3) . . . . ?
C4 C3 C8 N1 178.7(2) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C14 C15 C16 C17 -177.8(3) . . . . ?
C1 N1 C8 C3 -0.4(3) . . . . ?
C1 N1 C8 C7 178.2(3) . . . . ?
C1 C2 C9 C10 -109.3(3) . . . . ?
C15 C20 C19 C18 -0.2(5) . . . . ?
C15 C14 C21 C22 -71.9(4) . . . . ?
C15 C14 C13 N4 0.7(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C21 C14 C15 C20 179.4(2) . . . . ?
C21 C14 C15 C16 -3.0(5) . . . . ?
C21 C14 C13 N4 -179.3(3) . . . . ?
C12 C7 C6 C5 178.8(3) . . . . ?
C8 N1 C1 C2 0.6(3) . . . . ?
C8 C3 C2 C9 -179.4(3) . . . . ?
C8 C3 C2 C1 0.3(3) . . . . ?
C8 C3 C4 C5 0.0(4) . . . . ?
C8 C7 C6 C5 -0.5(5) . . . . ?
C13 N4 C20 C15 0.1(3) . . . . ?
C13 N4 C20 C19 -177.9(3) . . . . ?
C13 C14 C15 C20 -0.6(3) . . . . ?
C13 C14 C15 C16 177.0(3) . . . . ?
C13 C14 C21 C22 108.1(3) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C19 C20 C15 C14 178.6(3) . . . . ?
C19 C20 C15 C16 0.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOH/H2O'
