# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_Sa5fHCl
_database_code_depnum_ccdc_archive 'CCDC 2407032'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Palacky University
Czech Republic
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_audit_creation_date             2024-12-02
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N4, Cl, H2 O'
_chemical_formula_sum            'C23 H27 Cl N4 O'
_chemical_formula_weight         410.93
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
_chemical_oxdiff_usercomment     'DT B'
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'
Cl Cl 0.3639 0.7018 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.13520(10)
_cell_length_b                   11.23990(10)
_cell_length_c                   18.2950(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2084.14(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8454
_cell_measurement_temperature    99.98(15)
_cell_measurement_theta_max      68.3090
_cell_measurement_theta_min      4.6030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10810
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.402
_diffrn_reflns_theta_min         4.617
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  25.00   0.50    0.50    --  -42.75  70.00 -99.00   82
  2  ω    -45.00 -20.00   0.50    0.50    --  -42.75  70.00 -99.00   50
  3  ω    -45.00 -20.00   0.50    0.50    --  -42.75 -70.00 129.00   50
  4  ω    -21.00  15.00   0.50    0.50    --   44.32 -70.00 129.00   72
  5  ω     41.00  66.00   0.50    0.50    --   44.32 -70.00 129.00   50
  6  ω   -146.00 -93.00   0.50    3.50    --  -93.31 -70.00 129.00  106
  7  ω    -81.00 -56.00   0.50    3.50    --  -93.31  70.00 -99.00   50
  8  ω     29.00  64.00   0.50    3.50    --   94.87 -70.00 129.00   70
  9  ω      6.00  31.00   0.50    0.50    --  -42.75  11.00  60.00   50
 10  ω     65.00 104.00   0.50    0.50    --   44.32 138.00   0.00   78
 11  ω    -21.00  30.00   0.50    0.50    --   44.32 -32.00   0.00  102
 12  ω    -21.00  18.00   0.50    0.50    --   44.32 -11.00 -30.00   78
 13  ω    -20.00  28.00   0.50    0.50    --   44.32 -21.00 -60.00   96
 14  ω    -19.00  15.00   0.50    0.50    --   44.32 -21.00 120.00   68
 15  ω     29.00  54.00   0.50    0.50    --   44.32  70.00 -99.00   50
 16  ω     77.00 102.00   0.50    0.50    --   44.32  70.00 -99.00   50
 17  ω    -54.00 -28.00   0.50    3.50    --  -93.31  50.00  90.00   52
 18  ω   -127.00-101.00   0.50    3.50    --  -93.31 -25.00-180.00   52
 19  ω   -158.00-131.00   0.50    3.50    --  -93.31 -25.00-180.00   54
 20  ω    -51.00 -26.00   0.50    3.50    --  -93.31  59.00-120.00   50
 21  ω    -61.00 -32.00   0.50    3.50    --  -93.31 117.00   0.00   58
 22  ω   -108.00 -73.00   0.50    3.50    --  -93.31 117.00   0.00   70
 23  ω   -106.00 -38.00   0.50    3.50    --  -93.31  77.00  30.00  136
 24  ω    -80.00 -30.00   0.50    3.50    --  -93.31  68.00  90.00  100
 25  ω   -158.00 -95.00   0.50    3.50    --  -93.31 -68.00  90.00  126
 26  ω     29.00  55.00   0.50    3.50    --   94.87 -50.00-120.00   52
 27  ω     45.00  70.00   0.50    3.50    --   94.87 -68.00  60.00   50
 28  ω    129.00 157.00   0.50    3.50    --   94.87  68.00-150.00   56
 29  ω     93.00 118.00   0.50    3.50    --   94.87  70.00 -99.00   50
 30  ω     73.00 100.00   0.50    3.50    --   94.87  68.00-150.00   54
 31  ω     31.00  56.00   0.50    3.50    --   94.87 -50.00  90.00   50
 32  ω     54.00 105.00   0.50    3.50    --   94.87 -96.00 120.00  102
 33  ω     25.00  51.00   0.50    3.50    --   94.87 -96.00 120.00   52
 34  ω     90.00 163.00   0.50    3.50    --   94.87  25.00 -30.00  146
 35  ω     31.00  56.00   0.50    3.50    --   94.87 -59.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0973157000
_diffrn_orient_matrix_UB_12      -0.0094567000
_diffrn_orient_matrix_UB_13      0.0644624000
_diffrn_orient_matrix_UB_21      0.0517695000
_diffrn_orient_matrix_UB_22      -0.1258220000
_diffrn_orient_matrix_UB_23      0.0170682000
_diffrn_orient_matrix_UB_31      0.1046065000
_diffrn_orient_matrix_UB_32      0.0535525000
_diffrn_orient_matrix_UB_33      0.0514457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3700
_reflns_number_total             3796
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.022(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.039
_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)+(0.0395P)²+0.3485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0688
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.978(13)
 0.022(13)
2. 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, All O(H,H) groups
3.a Free rotating group:
 O1(H1D,H1E)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C20(H20A,H20B), C22(H22A,H22B), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C12(H12), C13(H13), C9(H9), C8(H8), C7(H7), C6(H6),
 C15(H15), C17(H17), C16(H16)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_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
Cl1 Cl 0.11053(5) 0.65293(4) 0.47787(3) 0.02958(14) Uani 1 1 d . . . . .
N1 N 0.34167(16) 0.37629(14) 0.28711(9) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.22783(16) 0.46754(14) 0.37328(9) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.208207 0.504768 0.414180 0.026 Uiso 1 1 calc R U . . .
O1 O 0.20361(18) 0.14463(17) 0.05056(10) 0.0429(4) Uani 1 1 d G . . . .
H1D H 0.124623 0.170131 0.040455 0.064 Uiso 1 1 d G U . . .
H1E H 0.255914 0.198014 0.031902 0.064 Uiso 1 1 d G U . . .
N4 N 0.46019(17) 0.47419(14) 0.38423(9) 0.0205(3) Uani 1 1 d . . . . .
N3 N 0.36572(19) 0.19052(14) 0.38783(9) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.35029(19) 0.44025(16) 0.35034(11) 0.0193(4) Uani 1 1 d . . . . .
C4 C 0.20771(19) 0.36976(17) 0.26709(11) 0.0208(4) Uani 1 1 d . . . . .
C11 C 0.47379(19) 0.34216(18) 0.18069(11) 0.0223(4) Uani 1 1 d . . . . .
H11 H 0.414519 0.392026 0.154625 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4968(2) 0.18173(16) 0.36245(11) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.44773(18) 0.31290(17) 0.25203(11) 0.0188(4) Uani 1 1 d . . . . .
C19 C 0.52822(19) 0.23133(16) 0.29202(10) 0.0194(4) Uani 1 1 d . . . . .
C1 C 0.58462(19) 0.49524(18) 0.34523(11) 0.0241(4) Uani 1 1 d . . . . .
H1A H 0.646466 0.430493 0.355861 0.036 Uiso 1 1 calc R U . . .
H1B H 0.622764 0.570983 0.361278 0.036 Uiso 1 1 calc R U . . .
H1C H 0.567677 0.498303 0.292529 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1372(2) 0.42721(17) 0.32169(11) 0.0223(4) Uani 1 1 d . . . . .
C12 C 0.5879(2) 0.29868(18) 0.14589(12) 0.0260(4) Uani 1 1 d . . . . .
H12 H 0.602916 0.313971 0.095497 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6513(2) 0.20095(17) 0.25887(11) 0.0235(4) Uani 1 1 d . . . . .
C13 C 0.6768(2) 0.23414(18) 0.18566(12) 0.0261(4) Uani 1 1 d . . . . .
H13 H 0.757718 0.211020 0.163604 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1475(2) 0.32128(17) 0.20598(11) 0.0242(4) Uani 1 1 d . . . . .
H9 H 0.196224 0.280044 0.169556 0.029 Uiso 1 1 calc R U . . .
C2 C 0.4472(2) 0.52933(19) 0.45672(10) 0.0248(4) Uani 1 1 d . . . . .
H2A H 0.400278 0.605177 0.452152 0.037 Uiso 1 1 calc R U . . .
H2B H 0.535153 0.543454 0.477267 0.037 Uiso 1 1 calc R U . . .
H2C H 0.397669 0.476116 0.489064 0.037 Uiso 1 1 calc R U . . .
C23 C 0.2698(2) 0.11512(18) 0.34769(11) 0.0258(4) Uani 1 1 d . . . . .
H23A H 0.301518 0.031983 0.344443 0.031 Uiso 1 1 calc R U . . .
H23B H 0.255133 0.145963 0.297654 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0112(2) 0.3366(2) 0.20106(12) 0.0297(5) Uani 1 1 d . . . . .
H8 H -0.034467 0.305655 0.159882 0.036 Uiso 1 1 calc R U . . .
C7 C -0.0599(2) 0.3965(2) 0.25540(13) 0.0312(5) Uani 1 1 d . . . . .
H7 H -0.152553 0.405779 0.249857 0.037 Uiso 1 1 calc R U . . .
C6 C 0.0011(2) 0.44263(19) 0.31721(13) 0.0274(4) Uani 1 1 d . . . . .
H6 H -0.047271 0.482477 0.354334 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7476(2) 0.13990(19) 0.30064(13) 0.0309(5) Uani 1 1 d . . . . .
H15 H 0.831384 0.122667 0.279878 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5939(2) 0.12326(18) 0.40061(12) 0.0311(5) Uani 1 1 d . . . . .
H17 H 0.575422 0.093994 0.448245 0.037 Uiso 1 1 calc R U . . .
C20 C 0.3374(3) 0.1666(2) 0.46492(12) 0.0393(6) Uani 1 1 d . . . . .
H20A H 0.379977 0.225762 0.497317 0.047 Uiso 1 1 calc R U . . .
H20B H 0.365810 0.085619 0.479292 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7204(3) 0.1059(2) 0.37034(14) 0.0358(6) Uani 1 1 d . . . . .
H16 H 0.787603 0.069985 0.399065 0.043 Uiso 1 1 calc R U . . .
C22 C 0.1425(3) 0.1225(2) 0.39320(14) 0.0418(6) Uani 1 1 d . . . . .
H22A H 0.104584 0.042429 0.401284 0.050 Uiso 1 1 calc R U . . .
H22B H 0.075938 0.173109 0.368691 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1875(3) 0.1786(2) 0.46591(15) 0.0500(8) Uani 1 1 d . . . . .
H21A H 0.160889 0.263202 0.468660 0.060 Uiso 1 1 calc R U . . .
H21B H 0.149174 0.135442 0.508056 0.060 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
N1 C3 1.365(3) . ?
N1 C4 1.408(3) . ?
N1 C10 1.440(2) . ?
N2 H2 0.8800 . ?
N2 C3 1.346(3) . ?
N2 C5 1.393(3) . ?
O1 H1D 0.8702 . ?
O1 H1E 0.8703 . ?
N4 C3 1.331(3) . ?
N4 C1 1.468(2) . ?
N4 C2 1.470(2) . ?
N3 C18 1.410(3) . ?
N3 C23 1.484(3) . ?
N3 C20 1.464(3) . ?
C4 C5 1.387(3) . ?
C4 C9 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.372(3) . ?
C11 C12 1.408(3) . ?
C18 C19 1.440(3) . ?
C18 C17 1.374(3) . ?
C10 C19 1.429(3) . ?
C19 C14 1.429(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C5 C6 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.367(3) . ?
C14 C13 1.414(3) . ?
C14 C15 1.417(3) . ?
C13 H13 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.396(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C22 1.538(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.400(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.359(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.411(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.526(4) . ?
C16 H16 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C21 1.541(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 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
C3 N1 C4 108.03(16) . . ?
C3 N1 C10 126.19(16) . . ?
C4 N1 C10 125.30(16) . . ?
C3 N2 H2 125.6 . . ?
C3 N2 C5 108.81(17) . . ?
C5 N2 H2 125.6 . . ?
H1D O1 H1E 104.5 . . ?
C3 N4 C1 122.60(16) . . ?
C3 N4 C2 117.82(16) . . ?
C1 N4 C2 116.57(16) . . ?
C18 N3 C23 114.45(16) . . ?
C18 N3 C20 119.27(19) . . ?
C20 N3 C23 104.08(16) . . ?
N2 C3 N1 109.00(17) . . ?
N4 C3 N1 126.84(17) . . ?
N4 C3 N2 124.14(17) . . ?
C5 C4 N1 106.56(17) . . ?
C9 C4 N1 130.92(18) . . ?
C9 C4 C5 122.51(18) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.35(19) . . ?
C12 C11 H11 119.8 . . ?
N3 C18 C19 118.43(17) . . ?
C17 C18 N3 122.72(19) . . ?
C17 C18 C19 118.8(2) . . ?
C11 C10 N1 116.68(17) . . ?
C11 C10 C19 122.08(18) . . ?
C19 C10 N1 121.02(17) . . ?
C10 C19 C18 125.47(18) . . ?
C14 C19 C18 118.73(18) . . ?
C14 C19 C10 115.77(18) . . ?
N4 C1 H1A 109.5 . . ?
N4 C1 H1B 109.5 . . ?
N4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C5 C6 130.7(2) . . ?
C4 C5 N2 107.46(17) . . ?
C4 C5 C6 121.7(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.02(19) . . ?
C13 C12 H12 120.5 . . ?
C13 C14 C19 119.91(19) . . ?
C13 C14 C15 120.84(19) . . ?
C15 C14 C19 119.24(19) . . ?
C12 C13 C14 121.59(19) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C4 C9 H9 122.0 . . ?
C4 C9 C8 116.08(19) . . ?
C8 C9 H9 122.0 . . ?
N4 C2 H2A 109.5 . . ?
N4 C2 H2B 109.5 . . ?
N4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C23 H23A 110.8 . . ?
N3 C23 H23B 110.8 . . ?
N3 C23 C22 104.52(17) . . ?
H23A C23 H23B 108.9 . . ?
C22 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
C9 C8 H8 119.2 . . ?
C9 C8 C7 121.5(2) . . ?
C7 C8 H8 119.2 . . ?
C8 C7 H7 119.1 . . ?
C6 C7 C8 121.9(2) . . ?
C6 C7 H7 119.1 . . ?
C5 C6 H6 121.9 . . ?
C7 C6 C5 116.3(2) . . ?
C7 C6 H6 121.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C18 C17 H17 119.4 . . ?
C18 C17 C16 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
N3 C20 H20A 111.6 . . ?
N3 C20 H20B 111.6 . . ?
N3 C20 C21 101.0(2) . . ?
H20A C20 H20B 109.4 . . ?
C21 C20 H20A 111.6 . . ?
C21 C20 H20B 111.6 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C23 C22 H22A 111.0 . . ?
C23 C22 H22B 111.0 . . ?
C23 C22 C21 104.0(2) . . ?
H22A C22 H22B 109.0 . . ?
C21 C22 H22A 111.0 . . ?
C21 C22 H22B 111.0 . . ?
C20 C21 C22 104.4(2) . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
C22 C21 H21A 110.9 . . ?
C22 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?

_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 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.804
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.978(13)
2 0.022(13)

####################################################################### 
# 
# 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_Ra5f
_database_code_depnum_ccdc_archive 'CCDC 2407034'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Palacky University
Czech Republic
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_audit_creation_date             2024-11-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N4, C2 H6 O'
_chemical_formula_sum            'C25 H30 N4 O'
_chemical_formula_weight         402.53
_chemical_absolute_configuration ad
_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           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                   7.46170(10)
_cell_length_b                   13.90680(10)
_cell_length_c                   10.46010(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.5230(10)
_cell_angle_gamma                90
_cell_volume                     1083.376(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18399
_cell_measurement_temperature    89.9(4)
_cell_measurement_theta_max      69.7260
_cell_measurement_theta_min      4.2230
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.821
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.115a (Rigaku Oxford Diffraction, 2024)
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    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23039
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.603
_diffrn_reflns_theta_min         4.235
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      89.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  -2.00   0.50    0.40    --  -42.75 110.00 116.00   88
  2  ω    -82.00 -55.00   0.50    0.40    --  -42.75 110.00 116.00   54
  3  ω    -98.00 -67.00   0.50    1.50    --  -95.95 110.00 116.00   62
  4  ω   -146.00-121.00   0.50    1.50    --  -95.95-110.00  21.00   50
  5  ω     82.00 113.00   0.50    1.50    --   97.51 110.00 116.00   62
  6  ω     46.00  88.00   0.50    1.50    --   97.51-110.00  21.00   84
  7  ω    -27.00   0.00   0.50    0.40    --   10.00 106.00  45.08   54
  8  ω    -22.00   7.00   0.50    0.40    --   14.00 103.00-138.68   58
  9  ω    -13.00  12.00   0.50    0.40    --   22.00 102.00  99.71   50
 10  ω     -3.00  27.00   0.50    0.40    --   26.00  97.00-151.13   60
 11  ω     -2.00  23.00   0.50    0.40    --   30.00  97.00-105.53   50
 12  ω      2.00  27.00   0.50    0.40    --   34.00  95.00 -47.19   50
 13  ω     10.00  35.00   0.50    0.40    --   38.00  85.00-173.61   50
 14  ω    -34.00  -7.00   0.50    0.40    --  -38.00 -94.00  60.66   54
 15  ω    -34.00  -8.00   0.50    0.40    --  -38.00 -91.00 104.91   52
 16  ω      8.00  33.00   0.50    0.40    --   38.00  92.00  58.11   50
 17  ω      7.00  32.00   0.50    0.40    --   38.00  94.00  82.67   50
 18  ω    -35.00  -9.00   0.50    0.40    --  -38.00 -90.00 -56.52   52
 19  ω     12.00  41.00   0.50    0.40    --   42.00  92.00-147.98   58
 20  ω    -41.00 -15.00   0.50    0.40    --  -42.00 -82.00 106.03   52
 21  ω     12.00  37.00   0.50    0.40    --   42.00  90.00   5.83   50
 22  ω    -95.00 -19.00   0.50    0.40    --  -42.75 138.00-150.00  152
 23  ω    -99.00 -59.00   0.50    0.40    --  -42.75 138.00 -30.00   80
 24  ω    -90.00 -20.00   0.50    0.40    --  -42.75 138.00 150.00  140
 25  ω     49.00  75.00   0.50    0.40    --   44.32-110.00  21.00   52
 26  ω     16.00  41.00   0.50    0.40    --   44.32  86.00  10.69   50
 27  ω     17.00  42.00   0.50    0.40    --   46.00  88.00 -28.67   50
 28  ω     16.00  41.00   0.50    0.40    --   46.00  91.00 -55.33   50
 29  ω     16.00  41.00   0.50    0.40    --   46.00  90.00-108.09   50
 30  ω    -41.00 -16.00   0.50    0.40    --  -46.00 -92.00 167.57   50
 31  ω     26.00  51.00   0.50    0.40    --   50.00  77.00  42.88   50
 32  ω    -86.00 -37.00   0.50    0.40    --  -54.00 -62.00  86.62   98
 33  ω    -61.00 -29.00   0.50    0.40    --  -54.00 -77.00 134.29   64
 34  ω    -71.00 -34.00   0.50    0.40    --  -58.00 -73.00   8.28   74
 35  ω   -119.00 -94.00   0.50    0.40    --  -58.00 -73.00   8.28   50
 36  ω    -59.00 -33.00   0.50    0.40    --  -58.00 -76.00-168.44   52
 37  ω    -69.00 -33.00   0.50    0.40    --  -58.00 -76.00-128.88   72
 38  ω    -59.00 -34.00   0.50    0.40    --  -58.00 -73.00 -97.31   50
 39  ω     33.00  59.00   0.50    0.40    --   58.00  77.00 -12.75   52
 40  ω    -61.00 -33.00   0.50    0.40    --  -58.00 -77.00 -30.12   56
 41  ω   -124.00 -85.00   0.50    0.40    --  -58.00 -77.00 -30.12   78
 42  ω   -122.00 -96.00   0.50    0.40    --  -58.00 -73.00 -97.31   52
 43  ω   -117.00 -91.00   0.50    0.40    --  -58.00 -76.00-168.44   52
 44  ω    -62.00 -37.00   0.50    0.40    --  -62.00 -75.00  96.17   50
 45  ω    -70.00 -40.00   0.50    0.40    --  -62.00 -69.00  68.39   60
 46  ω    -70.00 -39.00   0.50    0.40    --  -62.00 -70.00  37.32   62
 47  ω    -65.00 -39.00   0.50    0.40    --  -62.00 -70.00 151.10   52
 48  ω    -89.00 -41.00   0.50    0.40    --  -62.00 -67.00  55.11   96
 49  ω   -127.00-102.00   0.50    0.40    --  -62.00 -67.00  55.11   50
 50  ω    -71.00 -45.00   0.50    0.40    --  -62.00 -57.00 100.84   52
 51  ω    -86.00 -41.00   0.50    0.40    --  -66.00 -76.00-123.49   90
 52  ω   -128.00 -97.00   0.50    0.40    --  -66.00 -76.00-123.49   62
 53  ω    -70.00 -45.00   0.50    1.50    --  -70.00 -76.00  69.58   50
 54  ω    -70.00 -45.00   0.50    1.50    --  -70.00 -75.00 -39.36   50
 55  ω   -128.00-103.00   0.50    1.50    --  -70.00 -75.00 -39.36   50
 56  ω     45.00  71.00   0.50    0.40    --   70.00  77.00  59.64   52
 57  ω    109.00 136.00   0.50    0.40    --   70.00  77.00  59.64   54
 58  ω    -82.00 -49.00   0.50    1.50    --  -74.00 -77.00 107.26   66
 59  ω   -128.00-103.00   0.50    1.50    --  -74.00 -77.00 107.26   50
 60  ω     52.00  78.00   0.50    1.50    --   74.00  75.00 117.20   52
 61  ω    -88.00 -49.00   0.50    1.50    --  -74.00 -77.00 -54.31   78
 62  ω   -138.00 -96.00   0.50    1.50    --  -74.00 -77.00 -54.31   84
 63  ω    -85.00 -55.00   0.50    1.50    --  -78.00 -74.00 -81.71   60
 64  ω    -78.00 -53.00   0.50    1.50    --  -78.00 -75.00 129.33   50
 65  ω    -82.00 -54.00   0.50    1.50    --  -78.00 -75.00 155.78   56
 66  ω   -145.00-120.00   0.50    1.50    --  -78.00 -76.00 103.39   50
 67  ω    -82.00 -53.00   0.50    1.50    --  -78.00 -75.00   9.36   58
 68  ω   -138.00-112.00   0.50    1.50    --  -78.00 -75.00   9.36   52
 69  ω   -108.00 -53.00   0.50    1.50    --  -78.00 -76.00 103.39  110
 70  ω    -88.00 -58.00   0.50    1.50    --  -78.00 -67.00-141.76   60
 71  ω   -109.00 -60.00   0.50    1.50    --  -82.00 -77.00 173.70   98
 72  ω    -84.00 -58.00   0.50    1.50    --  -82.00 -74.00 -96.92   52
 73  ω   -118.00 -58.00   0.50    1.50    --  -82.00 -74.00  57.39  120
 74  ω    -90.00 -59.00   0.50    1.50    --  -82.00 -71.00-158.47   62
 75  ω   -148.00-122.00   0.50    1.50    --  -82.00 -71.00-158.47   52
 76  ω    -83.00 -58.00   0.50    1.50    --  -82.00 -73.00  -4.99   50
 77  ω    -85.00 -59.00   0.50    1.50    --  -82.00 -75.00-113.22   52
 78  ω   -106.00 -61.00   0.50    1.50    --  -86.00 -75.00 -30.39   90
 79  ω    -87.00 -61.00   0.50    1.50    --  -86.00 -76.00-128.76   52
 80  ω   -150.00-102.00   0.50    1.50    --  -86.00 -76.00-128.76   96
 81  ω    -94.00 -61.00   0.50    1.50    --  -86.00 -75.00  46.76   66
 82  ω    -98.00 -63.00   0.50    1.50    --  -86.00 -76.00  -3.66   70
 83  ω    -89.00 -63.00   0.50    1.50    --  -86.00 -74.00 -89.29   52
 84  ω   -147.00 -97.00   0.50    1.50    --  -86.00 -74.00 -89.29  100
 85  ω   -129.00 -99.00   0.50    1.50    --  -86.00 -75.00  46.76   60
 86  ω    -88.00 -63.00   0.50    1.50    --  -86.00 -73.00 140.49   50
 87  ω    -91.00 -63.00   0.50    1.50    --  -86.00 -69.00-172.65   56
 88  ω   -133.00 -66.00   0.50    1.50    --  -90.00 -76.00 137.33  134
 89  ω   -136.00 -88.00   0.50    1.50    --  -94.00 -60.00 179.03   96
 90  ω   -160.00-130.00   0.50    1.50    --  -95.95 -76.00 117.88   60
 91  ω   -126.00 -75.00   0.50    1.50    --  -95.95 -68.00 -60.00  102
 92  ω   -162.00 -79.00   0.50    1.50    --  -95.95 -68.00-150.00  166
 93  ω   -105.00 -33.00   0.50    1.50    --  -95.95  77.00 120.00  144
 94  ω    -81.00 -40.00   0.50    1.50    --  -95.95  68.00  60.00   82
 95  ω   -164.00 -75.00   0.50    1.50    --  -95.95 -77.00   0.00  178
 96  ω   -143.00 -90.00   0.50    1.50    --  -95.95 -33.00   0.00  106
 97  ω    -99.00 -74.00   0.50    1.50    --  -95.95 -68.00  90.00   50
 98  ω   -132.00-106.00   0.50    1.50    --  -95.95 -68.00  90.00   52
 99  ω    -98.00 -71.00   0.50    1.50    --  -95.95 -77.00-180.00   54
100  ω    -74.00 -33.00   0.50    1.50    --  -95.95  68.00 -30.00   82
101  ω   -107.00 -71.00   0.50    1.50    --  -95.95 -76.00 117.88   72
102  ω   -162.00 -99.00   0.50    1.50    --  -95.95 -59.00-120.00  126
103  ω   -165.00 -84.00   0.50    1.50    --  -95.95 -96.00 -60.00  162
104  ω   -161.00 -77.00   0.50    1.50    --  -95.95 -77.00 -90.00  168
105  ω   -159.00 -76.00   0.50    1.50    --  -95.95 -77.00 -30.00  166
106  ω    -68.00 -30.00   0.50    1.50    --  -95.95 145.00 150.00   76
107  ω   -127.00 -88.00   0.50    1.50    --  -95.95 145.00 150.00   78
108  ω    -64.00 -38.00   0.50    1.50    --  -95.95 110.00 116.00   52
109  ω   -100.00 -74.00   0.50    1.50    --  -95.95 -77.00  30.00   52
110  ω   -148.00-119.00   0.50    1.50    --  -95.95 -77.00  30.00   58
111  ω     73.00 154.00   0.50    1.50    --   97.51  77.00  90.00  162
112  ω     74.00 126.00   0.50    1.50    --   97.51  77.00 -60.00  104
113  ω    129.00 155.00   0.50    1.50    --   97.51  68.00 -90.00   52
114  ω     31.00  56.00   0.50    1.50    --   97.51 -50.00 150.00   50
115  ω     43.00  68.00   0.50    1.50    --   97.51 -59.00  60.00   50
116  ω     76.00 102.00   0.50    1.50    --   97.51  68.00 -90.00   52
117  ω    137.00 162.00   0.50    1.50    --   97.51  68.00-120.00   50
118  ω     79.00 105.00   0.50    1.50    --   97.51  68.00-120.00   52
119  ω    117.00 162.00   0.50    1.50    --   97.51 117.00   0.00   90
120  ω     73.00 160.00   0.50    1.50    --   97.51  77.00  60.00  174
121  ω     73.00 144.00   0.50    1.50    --   97.51  77.00  30.00  142
122  ω     75.00 163.00   0.50    1.50    --   97.51  68.00 120.00  176
123  ω     33.00  67.00   0.50    1.50    --   97.51 -59.00-120.00   68
124  ω     38.00 107.00   0.50    1.50    --   97.51 -96.00 -90.00  138
125  ω     31.00  56.00   0.50    1.50    --   97.51 -50.00 -30.00   50
126  ω     78.00 109.00   0.50    1.50    --   97.51-117.00   0.00   62
127  ω     40.00  74.00   0.50    1.50    --   97.51-117.00   0.00   68
128  ω     31.00  56.00   0.50    1.50    --   97.51 -59.00   0.00   50
129  ω     80.00 162.00   0.50    1.50    --   97.51 117.00 -30.00  164
130  ω     31.00  56.00   0.50    1.50    --   97.51 -50.00 -90.00   50
131  ω     76.00 102.00   0.50    1.50    --   97.51  68.00  90.00   52
132  ω     37.00 101.00   0.50    1.50    --   97.51-117.00-150.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0263931000
_diffrn_orient_matrix_UB_12      -0.0394180000
_diffrn_orient_matrix_UB_13      -0.1375397000
_diffrn_orient_matrix_UB_21      -0.0348130000
_diffrn_orient_matrix_UB_22      -0.1010501000
_diffrn_orient_matrix_UB_23      0.0535251000
_diffrn_orient_matrix_UB_31      -0.2021699000
_diffrn_orient_matrix_UB_32      0.0224572000
_diffrn_orient_matrix_UB_33      -0.0005856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3922
_reflns_number_total             4030
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.57a 64-bit (release 20-05-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1834 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4030
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+0.1274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0717
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.1038(2) 0.30262(11) 0.91336(14) 0.0350(4) Uani 1 1 d . . . . .
H1 H 0.128888 0.340335 0.854334 0.052 Uiso 1 1 calc R U . . .
C24 C 0.2626(3) 0.27854(15) 0.9875(2) 0.0338(5) Uani 1 1 d . . . . .
H24A H 0.352980 0.254541 0.929822 0.041 Uiso 1 1 calc R U . . .
H24B H 0.235761 0.225814 1.046969 0.041 Uiso 1 1 calc R U . . .
C25 C 0.3413(3) 0.36196(18) 1.0638(2) 0.0405(5) Uani 1 1 d . . . . .
H25A H 0.379438 0.411920 1.005253 0.061 Uiso 1 1 calc R U . . .
H25B H 0.445063 0.339904 1.117933 0.061 Uiso 1 1 calc R U . . .
H25C H 0.250502 0.388329 1.117905 0.061 Uiso 1 1 calc R U . . .
N1 N 0.2636(2) 0.53085(10) 0.55885(13) 0.0182(3) Uani 1 1 d . . . . .
N2 N 0.2036(2) 0.43762(11) 0.72733(14) 0.0211(3) Uani 1 1 d . . . . .
N3 N 0.2773(2) 0.35735(11) 0.53868(15) 0.0292(4) Uani 1 1 d . . . . .
N4 N 0.6256(2) 0.47972(11) 0.59806(14) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.2243(2) 0.59314(13) 0.65790(16) 0.0196(4) Uani 1 1 d . . . . .
C2 C 0.2222(3) 0.69282(14) 0.66475(17) 0.0246(4) Uani 1 1 d . . . . .
H2 H 0.247966 0.731992 0.593764 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1803(3) 0.73210(15) 0.78173(18) 0.0303(5) Uani 1 1 d . . . . .
H3 H 0.178193 0.800043 0.790936 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1414(3) 0.67474(15) 0.88560(19) 0.0303(5) Uani 1 1 d . . . . .
H4 H 0.112135 0.704266 0.963530 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1446(3) 0.57491(14) 0.87713(17) 0.0251(4) Uani 1 1 d . . . . .
H5 H 0.117752 0.535863 0.947978 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1884(2) 0.53402(13) 0.76179(17) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.2474(2) 0.43852(13) 0.60664(16) 0.0190(4) Uani 1 1 d . . . . .
C8 C 0.2430(3) 0.34734(13) 0.40247(18) 0.0264(4) Uani 1 1 d . . . . .
H8A H 0.140853 0.304004 0.384971 0.040 Uiso 1 1 calc R U . . .
H8B H 0.349486 0.320710 0.365001 0.040 Uiso 1 1 calc R U . . .
H8C H 0.215285 0.410487 0.364644 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2825(4) 0.26753(15) 0.6102(2) 0.0400(6) Uani 1 1 d . . . . .
H9A H 0.361594 0.274826 0.687912 0.060 Uiso 1 1 calc R U . . .
H9B H 0.328296 0.216146 0.556997 0.060 Uiso 1 1 calc R U . . .
H9C H 0.161169 0.251142 0.633830 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3196(2) 0.56327(12) 0.43746(16) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.1942(3) 0.61503(12) 0.36459(17) 0.0212(4) Uani 1 1 d . . . . .
H11 H 0.083175 0.630727 0.399265 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2265(3) 0.64529(13) 0.23973(17) 0.0241(4) Uani 1 1 d . . . . .
H12 H 0.140783 0.683402 0.191762 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3831(3) 0.61894(13) 0.18876(17) 0.0234(4) Uani 1 1 d . . . . .
H13 H 0.402723 0.635841 0.102731 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5174(3) 0.56684(13) 0.26142(17) 0.0215(4) Uani 1 1 d . . . . .
C15 C 0.6780(3) 0.54014(13) 0.20469(17) 0.0250(4) Uani 1 1 d . . . . .
H15 H 0.694920 0.557433 0.118402 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8077(3) 0.49006(14) 0.27278(19) 0.0259(4) Uani 1 1 d . . . . .
H16 H 0.911794 0.469439 0.232568 0.031 Uiso 1 1 calc R U . . .
C17 C 0.7883(3) 0.46850(12) 0.40332(18) 0.0235(4) Uani 1 1 d . . . . .
H17 H 0.881811 0.434840 0.450041 0.028 Uiso 1 1 calc R U . . .
C18 C 0.6381(2) 0.49489(12) 0.46453(17) 0.0200(4) Uani 1 1 d . . . . .
C19 C 0.4919(2) 0.54138(12) 0.39215(16) 0.0184(4) Uani 1 1 d . . . . .
C20 C 0.6708(3) 0.56420(13) 0.67916(17) 0.0237(4) Uani 1 1 d . . . . .
H20A H 0.581112 0.616058 0.664117 0.028 Uiso 1 1 calc R U . . .
H20B H 0.791296 0.589423 0.662633 0.028 Uiso 1 1 calc R U . . .
C21 C 0.6670(3) 0.52433(15) 0.81585(18) 0.0280(4) Uani 1 1 d . . . . .
H21A H 0.551329 0.539372 0.852984 0.034 Uiso 1 1 calc R U . . .
H21B H 0.765994 0.551669 0.871807 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6904(3) 0.41415(15) 0.80046(19) 0.0302(5) Uani 1 1 d . . . . .
H22A H 0.791766 0.390230 0.857205 0.036 Uiso 1 1 calc R U . . .
H22B H 0.579730 0.379579 0.820882 0.036 Uiso 1 1 calc R U . . .
C23 C 0.7285(3) 0.40087(15) 0.65996(19) 0.0277(4) Uani 1 1 d . . . . .
H23A H 0.858234 0.407111 0.646935 0.033 Uiso 1 1 calc R U . . .
H23B H 0.685549 0.337561 0.627405 0.033 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
O1 H1 0.8400 . ?
O1 C24 1.416(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.507(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 C1 1.395(2) . ?
N1 C7 1.386(2) . ?
N1 C10 1.434(2) . ?
N2 C6 1.395(2) . ?
N2 C7 1.324(2) . ?
N3 C7 1.360(2) . ?
N3 C8 1.439(2) . ?
N3 C9 1.455(3) . ?
N4 C18 1.421(2) . ?
N4 C20 1.476(2) . ?
N4 C23 1.466(2) . ?
C1 C2 1.388(3) . ?
C1 C6 1.401(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.374(3) . ?
C10 C19 1.430(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.407(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.364(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.419(3) . ?
C14 C15 1.419(3) . ?
C14 C19 1.437(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.358(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.414(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(3) . ?
C18 C19 1.442(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.535(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.552(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.525(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 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
C24 O1 H1 109.5 . . ?
O1 C24 H24A 108.9 . . ?
O1 C24 H24B 108.9 . . ?
O1 C24 C25 113.19(18) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C10 123.26(14) . . ?
C7 N1 C1 106.29(14) . . ?
C7 N1 C10 130.34(14) . . ?
C7 N2 C6 105.44(14) . . ?
C7 N3 C8 124.97(15) . . ?
C7 N3 C9 116.36(15) . . ?
C8 N3 C9 115.06(15) . . ?
C18 N4 C20 114.84(14) . . ?
C18 N4 C23 118.73(15) . . ?
C23 N4 C20 104.26(14) . . ?
N1 C1 C6 105.69(15) . . ?
C2 C1 N1 131.43(17) . . ?
C2 C1 C6 122.85(17) . . ?
C1 C2 H2 121.9 . . ?
C1 C2 C3 116.15(18) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 121.97(19) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.09(18) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 117.98(18) . . ?
C6 C5 H5 121.0 . . ?
N2 C6 C1 109.94(15) . . ?
C5 C6 N2 130.12(16) . . ?
C5 C6 C1 119.94(16) . . ?
N2 C7 N1 112.63(15) . . ?
N2 C7 N3 123.29(16) . . ?
N3 C7 N1 124.06(15) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 115.49(16) . . ?
C11 C10 C19 121.55(16) . . ?
C19 C10 N1 122.93(15) . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.46(18) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.83(17) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.44(16) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C19 120.35(17) . . ?
C15 C14 C13 119.76(16) . . ?
C15 C14 C19 119.88(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.52(17) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.22(18) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.85(17) . . ?
C18 C17 H17 119.1 . . ?
N4 C18 C19 119.30(15) . . ?
C17 C18 N4 121.51(16) . . ?
C17 C18 C19 119.17(16) . . ?
C10 C19 C14 115.94(16) . . ?
C10 C19 C18 125.99(15) . . ?
C14 C19 C18 118.05(16) . . ?
N4 C20 H20A 111.1 . . ?
N4 C20 H20B 111.1 . . ?
N4 C20 C21 103.36(15) . . ?
H20A C20 H20B 109.1 . . ?
C21 C20 H20A 111.1 . . ?
C21 C20 H20B 111.1 . . ?
C20 C21 H21A 110.8 . . ?
C20 C21 H21B 110.8 . . ?
C20 C21 C22 104.55(16) . . ?
H21A C21 H21B 108.9 . . ?
C22 C21 H21A 110.8 . . ?
C22 C21 H21B 110.8 . . ?
C21 C22 H22A 110.9 . . ?
C21 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
C23 C22 C21 104.38(16) . . ?
C23 C22 H22A 110.9 . . ?
C23 C22 H22B 110.9 . . ?
N4 C23 C22 102.21(15) . . ?
N4 C23 H23A 111.3 . . ?
N4 C23 H23B 111.3 . . ?
C22 C23 H23A 111.3 . . ?
C22 C23 H23B 111.3 . . ?
H23A C23 H23B 109.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.370
_oxdiff_exptl_absorpt_empirical_full_min 0.744
####################################################################### 
# 
# 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_Sa5f
_database_code_depnum_ccdc_archive 'CCDC 2407035'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Palacky University
Czech Republic
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_audit_creation_date             2024-11-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N4, C2 H6 O'
_chemical_formula_sum            'C25 H30 N4 O'
_chemical_formula_weight         402.53
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O '
_chemical_oxdiff_usercomment     'DT B'
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                   7.4550(2)
_cell_length_b                   13.9094(2)
_cell_length_c                   10.4634(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.455(2)
_cell_angle_gamma                90
_cell_volume                     1083.03(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13763
_cell_measurement_temperature    89.9(4)
_cell_measurement_theta_max      68.2460
_cell_measurement_theta_min      4.2150
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.115a (Rigaku Oxford Diffraction, 2024)
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    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23167
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.642
_diffrn_reflns_theta_min         4.233
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      89.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -24.00   0.50    2.00    --  -42.75 136.00 -45.00   58
  2  ω    -91.00 -57.00   0.50    2.00    --  -42.75 136.00 -45.00   68
  3  ω    -64.00 -24.00   0.50    2.00    --  -42.75 133.00 136.00   80
  4  ω     34.00  99.00   0.50    2.00    --   44.32-136.00-110.00  130
  5  ω     31.00  58.00   0.50    2.00    --   44.32-133.00  67.00   54
  6  ω    -99.00 -74.00   0.50    6.20    --  -93.31 136.00 -45.00   50
  7  ω   -130.00-105.00   0.50    6.20    --  -93.31-136.00-110.00   50
  8  ω    -94.00 -67.00   0.50    6.20    --  -93.31 133.00 136.00   54
  9  ω     74.00 108.00   0.50    6.20    --   94.87-133.00  67.00   68
 10  ω     94.00 121.00   0.50    6.20    --   94.87 136.00 -45.00   54
 11  ω     90.00 115.00   0.50    6.20    --   94.87 133.00 136.00   50
 12  ω     66.00 120.00   0.50    6.20    --   94.87-136.00-110.00  108
 13  ω    -55.00 -16.00   0.50    2.00    --   -4.00 129.00  56.70   78
 14  ω    -35.00 -10.00   0.50    2.00    --    8.00 118.00-127.58   50
 15  ω    -12.00  14.00   0.50    2.00    --   20.00 100.00  62.69   52
 16  ω     -9.00  16.00   0.50    2.00    --   24.00 101.00-126.93   50
 17  ω      4.00  29.00   0.50    2.00    --   36.00  96.00  82.18   50
 18  ω      5.00  30.00   0.50    2.00    --   36.00  94.00  32.07   50
 19  ω      4.00  30.00   0.50    2.00    --   36.00  96.00-162.82   52
 20  ω      4.00  29.00   0.50    2.00    --   36.00  95.00 134.90   50
 21  ω      4.00  29.00   0.50    2.00    --   36.00  96.00 -18.87   50
 22  ω     12.00  39.00   0.50    2.00    --   40.00  89.00 169.33   54
 23  ω     12.00  37.00   0.50    2.00    --   40.00  85.00   3.07   50
 24  ω     11.00  36.00   0.50    2.00    --   40.00  89.00 -99.97   50
 25  ω     11.00  36.00   0.50    2.00    --   40.00  87.00 141.78   50
 26  ω     10.00  35.00   0.50    2.00    --   40.00  90.00 -57.31   50
 27  ω     11.00  36.00   0.50    2.00    --   40.00  89.00 -78.98   50
 28  ω      9.00  34.00   0.50    2.00    --   40.00  93.00-147.87   50
 29  ω     17.00  42.00   0.50    2.00    --   44.00  83.00-148.67   50
 30  ω     15.00  40.00   0.50    2.00    --   44.00  89.00-134.86   50
 31  ω     15.00  40.00   0.50    2.00    --   44.00  88.00 -96.06   50
 32  ω     14.00  39.00   0.50    2.00    --   44.00  92.00 139.30   50
 33  ω     17.00  42.00   0.50    2.00    --   44.00  83.00 -47.86   50
 34  ω     14.00  39.00   0.50    2.00    --   44.32  92.00  71.29   50
 35  ω     16.00  41.00   0.50    2.00    --   44.32  87.00   2.61   50
 36  ω     83.00 108.00   0.50    2.00    --   44.32  77.00  60.00   50
 37  ω     21.00  52.00   0.50    2.00    --   44.32  77.00  60.00   62
 38  ω     23.00  50.00   0.50    2.00    --   48.00  76.00 -79.87   54
 39  ω    -49.00 -24.00   0.50    2.00    --  -48.00 -72.00  50.87   50
 40  ω     90.00 120.00   0.50    2.00    --   52.00  77.00 -56.07   60
 41  ω    -54.00 -28.00   0.50    2.00    --  -52.00 -73.00-176.65   52
 42  ω    -55.00 -28.00   0.50    2.00    --  -52.00 -73.00 102.57   54
 43  ω     28.00  53.00   0.50    2.00    --   52.00  77.00 -56.07   50
 44  ω   -117.00 -92.00   0.50    2.00    --  -52.00 -73.00-176.65   50
 45  ω   -105.00 -77.00   0.50    2.00    --  -52.00 -73.00 102.57   56
 46  ω    -58.00 -29.00   0.50    2.00    --  -52.00 -70.00 -57.03   58
 47  ω   -121.00 -90.00   0.50    2.00    --  -56.00 -58.00  14.80   62
 48  ω   -121.00 -81.00   0.50    2.00    --  -56.00 -70.00-153.55   80
 49  ω     33.00  83.00   0.50    2.00    --   56.00  76.00 145.95  100
 50  ω    -87.00 -37.00   0.50    2.00    --  -56.00 -58.00  14.80  100
 51  ω    -58.00 -33.00   0.50    2.00    --  -56.00 -70.00-153.55   50
 52  ω   -121.00 -84.00   0.50    2.00    --  -60.00 -76.00 -68.59   74
 53  ω     35.00  62.00   0.50    2.00    --   60.00  77.00 179.02   54
 54  ω    -61.00 -35.00   0.50    2.00    --  -60.00 -76.00 -68.59   52
 55  ω    -75.00 -39.00   0.50    2.00    --  -64.00 -75.00 -76.03   72
 56  ω    -71.00 -41.00   0.50    2.00    --  -64.00 -69.00 -10.36   60
 57  ω    -67.00 -41.00   0.50    2.00    --  -64.00 -70.00 -25.82   52
 58  ω    -67.00 -42.00   0.50    2.00    --  -64.00 -68.00  58.45   50
 59  ω   -129.00-102.00   0.50    2.00    --  -64.00 -68.00  58.45   54
 60  ω    -64.00 -39.00   0.50    2.00    --  -64.00 -77.00 107.44   50
 61  ω    -70.00 -45.00   0.50    2.00    --  -68.00 -73.00  84.28   50
 62  ω   -123.00 -93.00   0.50    2.00    --  -68.00 -73.00  84.28   60
 63  ω    -68.00 -43.00   0.50    2.00    --  -68.00 -76.00 -23.89   50
 64  ω    -69.00 -44.00   0.50    2.00    --  -68.00 -72.00  32.01   50
 65  ω   -123.00 -96.00   0.50    2.00    --  -68.00 -72.00  32.01   54
 66  ω   -134.00 -81.00   0.50    6.20    --  -72.00 -76.00-125.62  106
 67  ω    -75.00 -48.00   0.50    6.20    --  -72.00 -76.00-144.20   54
 68  ω    -73.00 -47.00   0.50    6.20    --  -72.00 -76.00-125.62   52
 69  ω    -74.00 -47.00   0.50    6.20    --  -72.00 -76.00-169.18   54
 70  ω     51.00  80.00   0.50    6.20    --   72.00  76.00  59.95   58
 71  ω    -74.00 -47.00   0.50    6.20    --  -72.00 -76.00 168.48   54
 72  ω    -88.00 -61.00   0.50    6.20    --  -72.00 -66.00  71.70   54
 73  ω    -76.00 -51.00   0.50    6.20    --  -76.00 -77.00-154.44   50
 74  ω   -143.00-118.00   0.50    6.20    --  -76.00 -77.00-154.44   50
 75  ω    -87.00 -51.00   0.50    6.20    --  -76.00 -76.00 156.48   72
 76  ω   -141.00 -94.00   0.50    6.20    --  -76.00 -76.00 156.48   94
 77  ω    -91.00 -52.00   0.50    6.20    --  -76.00 -73.00 -92.06   78
 78  ω    -76.00 -51.00   0.50    6.20    --  -76.00 -75.00 129.24   50
 79  ω   -140.00-113.00   0.50    6.20    --  -76.00 -75.00 129.24   54
 80  ω    -88.00 -58.00   0.50    6.20    --  -80.00 -76.00 151.33   60
 81  ω    -87.00 -60.00   0.50    6.20    --  -80.00 -62.00 -12.97   54
 82  ω    -92.00 -55.00   0.50    6.20    --  -80.00 -75.00 -98.30   74
 83  ω   -136.00-109.00   0.50    6.20    --  -80.00 -75.00 -98.30   54
 84  ω    -87.00 -61.00   0.50    6.20    --  -84.00 -71.00 -64.57   52
 85  ω   -143.00-116.00   0.50    6.20    --  -84.00 -71.00 -64.57   54
 86  ω    -91.00 -59.00   0.50    6.20    --  -84.00 -75.00  48.20   64
 87  ω   -106.00 -62.00   0.50    6.20    --  -84.00 -67.00-148.56   88
 88  ω   -147.00 -94.00   0.50    6.20    --  -84.00 -75.00 117.07  106
 89  ω     61.00  96.00   0.50    6.20    --   84.00  72.00 110.38   70
 90  ω   -117.00 -61.00   0.50    6.20    --  -84.00 -69.00 -23.68  112
 91  ω    -88.00 -61.00   0.50    6.20    --  -84.00 -75.00 117.07   54
 92  ω   -141.00 -65.00   0.50    6.20    --  -88.00 -69.00-178.02  152
 93  ω    -96.00 -63.00   0.50    6.20    --  -88.00 -76.00-114.41   66
 94  ω   -146.00 -63.00   0.50    6.20    --  -88.00 -77.00 -26.97  166
 95  ω   -157.00 -99.00   0.50    6.20    --  -93.31-117.00 -90.00  116
 96  ω    -94.00 -68.00   0.50    6.20    --  -93.31 -77.00 115.03   52
 97  ω   -138.00 -71.00   0.50    6.20    --  -93.31 -72.00 -43.77  134
 98  ω   -122.00 -68.00   0.50    6.20    --  -93.31 -77.00  30.00  108
 99  ω    -54.00 -23.00   0.50    6.20    --  -93.31  96.00 120.00   62
100  ω   -100.00 -70.00   0.50    6.20    --  -93.31 -72.00  18.73   60
101  ω   -104.00 -55.00   0.50    6.20    --  -93.31  96.00 120.00   98
102  ω   -148.00-113.00   0.50    6.20    --  -93.31 -72.00  18.73   70
103  ω   -151.00-115.00   0.50    6.20    --  -93.31 -77.00 115.03   72
104  ω    -90.00 -24.00   0.50    6.20    --  -93.31  96.00 150.00  132
105  ω   -160.00 -70.00   0.50    6.20    --  -93.31 -72.00  79.60  180
106  ω   -104.00 -25.00   0.50    6.20    --  -93.31  96.00 -30.00  158
107  ω   -148.00-121.00   0.50    6.20    --  -93.31 -77.00-150.00   54
108  ω   -123.00 -68.00   0.50    6.20    --  -93.31 -77.00 150.00  110
109  ω    -80.00 -55.00   0.50    6.20    --  -93.31  68.00  90.00   50
110  ω   -159.00-129.00   0.50    6.20    --  -93.31 -77.00 150.00   60
111  ω   -137.00-112.00   0.50    6.20    --  -93.31-133.00  67.00   50
112  ω    -93.00 -68.00   0.50    6.20    --  -93.31 -77.00 -69.15   50
113  ω   -157.00 -68.00   0.50    6.20    --  -93.31 -77.00  60.00  178
114  ω   -146.00 -68.00   0.50    6.20    --  -93.31 -77.00   0.00  156
115  ω   -111.00 -71.00   0.50    6.20    --  -93.31 -77.00-150.00   80
116  ω    -82.00 -34.00   0.50    6.20    --  -93.31  77.00 -60.00   96
117  ω   -139.00-112.00   0.50    6.20    --  -93.31 -77.00 -69.15   54
118  ω     97.00 124.00   0.50    6.20    --   94.87  77.00 -30.00   54
119  ω     71.00 157.00   0.50    6.20    --   94.87  77.00-120.00  172
120  ω    111.00 136.00   0.50    6.20    --   94.87  59.00 -60.00   50
121  ω     80.00 106.00   0.50    6.20    --   94.87  59.00 -60.00   52
122  ω     72.00 159.00   0.50    6.20    --   94.87  77.00  90.00  174
123  ω     70.00  96.00   0.50    6.20    --   94.87  77.00-180.00   52
124  ω     74.00 159.00   0.50    6.20    --   94.87  77.00 -90.00  170
125  ω     91.00 162.00   0.50    6.20    --   94.87  59.00-180.00  142
126  ω     29.00  56.00   0.50    6.20    --   94.87 -50.00 -60.00   54
127  ω     29.00  80.00   0.50    6.20    --   94.87 -68.00 -90.00  102
128  ω     30.00  57.00   0.50    6.20    --   94.87 -68.00-120.00   54
129  ω     96.00 157.00   0.50    6.20    --   94.87  77.00-150.00  122
130  ω     29.00  56.00   0.50    6.20    --   94.87 -50.00  90.00   54
131  ω     29.00  56.00   0.50    6.20    --   94.87 -50.00  60.00   54
132  ω     31.00  56.00   0.50    6.20    --   94.87 -50.00  30.00   50
133  ω     44.00  91.00   0.50    6.20    --   94.87 -77.00   0.00   94
134  ω     71.00 118.00   0.50    6.20    --   94.87  77.00  60.00   94
135  ω    125.00 158.00   0.50    6.20    --   94.87  68.00 120.00   66
136  ω     73.00 106.00   0.50    6.20    --   94.87  68.00 120.00   66
137  ω     40.00  80.00   0.50    6.20    --   94.87 -68.00  60.00   80
138  ω     42.00  67.00   0.50    6.20    --   94.87 -59.00-180.00   50
139  ω    119.00 146.00   0.50    6.20    --   94.87  42.00 150.00   54
140  ω     77.00 104.00   0.50    6.20    --   94.87-117.00 -90.00   54
141  ω    120.00 156.00   0.50    6.20    --   94.87  68.00  60.00   72
142  ω    134.00 159.00   0.50    6.20    --   94.87  68.00  30.00   50
143  ω     40.00  74.00   0.50    6.20    --   94.87-117.00 -90.00   68
144  ω     73.00 100.00   0.50    6.20    --   94.87  68.00  60.00   54
145  ω     76.00 103.00   0.50    6.20    --   94.87  68.00  30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0057336000
_diffrn_orient_matrix_UB_12      -0.0230787000
_diffrn_orient_matrix_UB_13      -0.1437092000
_diffrn_orient_matrix_UB_21      0.0019713000
_diffrn_orient_matrix_UB_22      0.1083184000
_diffrn_orient_matrix_UB_23      -0.0306487000
_diffrn_orient_matrix_UB_31      0.2069078000
_diffrn_orient_matrix_UB_32      -0.0004975000
_diffrn_orient_matrix_UB_33      0.0131615000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3766
_reflns_number_total             3941
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.57a 64-bit (release 20-05-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.17(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²+0.1170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.8962(3) 0.69729(14) 0.08643(19) 0.0412(5) Uani 1 1 d . . . . .
H1 H 0.871368 0.658856 0.144717 0.062 Uiso 1 1 calc R U . . .
C23 C 0.7375(4) 0.7213(2) 0.0125(3) 0.0406(7) Uani 1 1 d . . . . .
H23A H 0.764336 0.774106 -0.046810 0.049 Uiso 1 1 calc R U . . .
H23B H 0.646988 0.745181 0.070282 0.049 Uiso 1 1 calc R U . . .
C24 C 0.6589(4) 0.6382(2) -0.0638(3) 0.0467(7) Uani 1 1 d . . . . .
H24A H 0.749757 0.611903 -0.118053 0.070 Uiso 1 1 calc R U . . .
H24B H 0.555049 0.660323 -0.117795 0.070 Uiso 1 1 calc R U . . .
H24C H 0.620670 0.588122 -0.005422 0.070 Uiso 1 1 calc R U . . .
N1 N 0.7366(3) 0.46931(13) 0.44106(18) 0.0236(4) Uani 1 1 d . . . . .
N2 N 0.7963(3) 0.56215(15) 0.27238(19) 0.0275(4) Uani 1 1 d . . . . .
N3 N 0.7228(3) 0.64260(15) 0.4615(2) 0.0350(5) Uani 1 1 d . . . . .
N4 N 0.3741(3) 0.52003(15) 0.40222(19) 0.0263(4) Uani 1 1 d . . . . .
C00B C 0.5080(3) 0.45857(16) 0.6079(2) 0.0252(5) Uani 1 1 d . . . . .
C1 C 0.7758(3) 0.40683(18) 0.3420(2) 0.0250(5) Uani 1 1 d . . . . .
C2 C 0.7776(3) 0.30707(18) 0.3350(2) 0.0309(6) Uani 1 1 d . . . . .
H2 H 0.751440 0.267903 0.405943 0.037 Uiso 1 1 calc R U . . .
C3 C 0.8198(4) 0.2678(2) 0.2181(2) 0.0361(6) Uani 1 1 d . . . . .
H3 H 0.822048 0.199912 0.208821 0.043 Uiso 1 1 calc R U . . .
C4 C 0.8588(4) 0.3254(2) 0.1145(3) 0.0364(6) Uani 1 1 d . . . . .
H4 H 0.888415 0.295938 0.036567 0.044 Uiso 1 1 calc R U . . .
C5 C 0.8554(3) 0.42494(19) 0.1227(2) 0.0309(6) Uani 1 1 d . . . . .
H5 H 0.882416 0.463918 0.051880 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8110(3) 0.46599(17) 0.2381(2) 0.0257(5) Uani 1 1 d . . . . .
C7 C 0.7525(3) 0.56123(17) 0.3934(2) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.7178(5) 0.7322(2) 0.3894(3) 0.0464(8) Uani 1 1 d . . . . .
H8A H 0.839213 0.748196 0.365111 0.070 Uiso 1 1 calc R U . . .
H8B H 0.672910 0.783940 0.442507 0.070 Uiso 1 1 calc R U . . .
H8C H 0.638068 0.724878 0.312115 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7565(4) 0.65265(18) 0.5968(2) 0.0327(6) Uani 1 1 d . . . . .
H9A H 0.790081 0.590092 0.634134 0.049 Uiso 1 1 calc R U . . .
H9B H 0.647875 0.676254 0.634735 0.049 Uiso 1 1 calc R U . . .
H9C H 0.854807 0.698482 0.614277 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6806(3) 0.43656(16) 0.5626(2) 0.0237(5) Uani 1 1 d . . . . .
C11 C 0.8058(3) 0.38488(16) 0.6355(2) 0.0271(5) Uani 1 1 d . . . . .
H11 H 0.917040 0.369188 0.600840 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7736(3) 0.35465(17) 0.7601(2) 0.0295(5) Uani 1 1 d . . . . .
H12 H 0.859363 0.316482 0.807928 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6165(4) 0.38113(17) 0.8114(2) 0.0294(5) Uani 1 1 d . . . . .
H13 H 0.596719 0.364351 0.897439 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4828(3) 0.43304(17) 0.7387(2) 0.0269(5) Uani 1 1 d . . . . .
C15 C 0.3216(3) 0.45994(17) 0.7960(2) 0.0306(5) Uani 1 1 d . . . . .
H15 H 0.304681 0.442976 0.882418 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1920(3) 0.50991(19) 0.7272(3) 0.0317(6) Uani 1 1 d . . . . .
H16 H 0.087338 0.530309 0.767083 0.038 Uiso 1 1 calc R U . . .
C17 C 0.2117(3) 0.53162(17) 0.5975(3) 0.0298(6) Uani 1 1 d . . . . .
H17 H 0.118527 0.565686 0.551052 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3622(3) 0.50495(16) 0.5356(2) 0.0253(5) Uani 1 1 d . . . . .
C19 C 0.2712(4) 0.5988(2) 0.3404(3) 0.0339(6) Uani 1 1 d . . . . .
H19A H 0.314200 0.662118 0.372842 0.041 Uiso 1 1 calc R U . . .
H19B H 0.141315 0.592621 0.353540 0.041 Uiso 1 1 calc R U . . .
C20 C 0.3092(4) 0.5855(2) 0.1999(3) 0.0371(6) Uani 1 1 d . . . . .
H20A H 0.419898 0.620085 0.179293 0.045 Uiso 1 1 calc R U . . .
H20B H 0.207668 0.609350 0.143253 0.045 Uiso 1 1 calc R U . . .
C21 C 0.3326(4) 0.4759(2) 0.1848(2) 0.0351(6) Uani 1 1 d . . . . .
H21A H 0.233481 0.448526 0.128940 0.042 Uiso 1 1 calc R U . . .
H21B H 0.448276 0.460891 0.147401 0.042 Uiso 1 1 calc R U . . .
C22 C 0.3291(3) 0.43575(18) 0.3211(2) 0.0301(5) Uani 1 1 d . . . . .
H22A H 0.208664 0.410337 0.337733 0.036 Uiso 1 1 calc R U . . .
H22B H 0.419137 0.383998 0.335848 0.036 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
O1 H1 0.8400 . ?
O1 C23 1.414(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.504(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 C1 1.397(3) . ?
N1 C7 1.380(3) . ?
N1 C10 1.436(3) . ?
N2 C6 1.391(3) . ?
N2 C7 1.327(3) . ?
N3 C7 1.363(3) . ?
N3 C8 1.457(3) . ?
N3 C9 1.429(3) . ?
N4 C18 1.419(3) . ?
N4 C19 1.466(3) . ?
N4 C22 1.474(3) . ?
C00B C10 1.431(3) . ?
C00B C14 1.437(3) . ?
C00B C18 1.440(3) . ?
C1 C2 1.390(4) . ?
C1 C6 1.401(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.404(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.368(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.415(4) . ?
C14 C15 1.425(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.361(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.407(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.525(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.544(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.534(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 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
C23 O1 H1 109.5 . . ?
O1 C23 H23A 108.9 . . ?
O1 C23 H23B 108.9 . . ?
O1 C23 C24 113.3(2) . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C10 123.00(18) . . ?
C7 N1 C1 106.35(18) . . ?
C7 N1 C10 130.53(19) . . ?
C7 N2 C6 105.36(19) . . ?
C7 N3 C8 116.1(2) . . ?
C7 N3 C9 125.1(2) . . ?
C9 N3 C8 115.3(2) . . ?
C18 N4 C19 118.9(2) . . ?
C18 N4 C22 115.03(19) . . ?
C19 N4 C22 104.22(19) . . ?
C10 C00B C14 115.8(2) . . ?
C10 C00B C18 126.0(2) . . ?
C14 C00B C18 118.3(2) . . ?
N1 C1 C6 105.5(2) . . ?
C2 C1 N1 131.5(2) . . ?
C2 C1 C6 122.9(2) . . ?
C1 C2 H2 121.9 . . ?
C1 C2 C3 116.1(2) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.0(2) . . ?
C6 C5 H5 121.0 . . ?
N2 C6 C1 110.1(2) . . ?
N2 C6 C5 130.1(2) . . ?
C5 C6 C1 119.8(2) . . ?
N2 C7 N1 112.7(2) . . ?
N2 C7 N3 123.3(2) . . ?
N3 C7 N1 124.1(2) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C00B C10 N1 122.8(2) . . ?
C11 C10 N1 115.7(2) . . ?
C11 C10 C00B 121.5(2) . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C00B 120.7(2) . . ?
C13 C14 C15 119.5(2) . . ?
C15 C14 C00B 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
N4 C18 C00B 119.6(2) . . ?
C17 C18 N4 121.5(2) . . ?
C17 C18 C00B 118.9(2) . . ?
N4 C19 H19A 111.3 . . ?
N4 C19 H19B 111.3 . . ?
N4 C19 C20 102.2(2) . . ?
H19A C19 H19B 109.2 . . ?
C20 C19 H19A 111.3 . . ?
C20 C19 H19B 111.3 . . ?
C19 C20 H20A 110.9 . . ?
C19 C20 H20B 110.9 . . ?
C19 C20 C21 104.3(2) . . ?
H20A C20 H20B 108.9 . . ?
C21 C20 H20A 110.9 . . ?
C21 C20 H20B 110.9 . . ?
C20 C21 H21A 110.8 . . ?
C20 C21 H21B 110.8 . . ?
H21A C21 H21B 108.9 . . ?
C22 C21 C20 104.8(2) . . ?
C22 C21 H21A 110.8 . . ?
C22 C21 H21B 110.8 . . ?
N4 C22 C21 103.3(2) . . ?
N4 C22 H22A 111.1 . . ?
N4 C22 H22B 111.1 . . ?
C21 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.661
####################################################################### 
# 
# 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_Ra5fHCl
_database_code_depnum_ccdc_archive 'CCDC 2407033'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Palacky University
Czech Republic
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_audit_creation_date             2024-12-02
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N4, Cl, H2 O'
_chemical_formula_sum            'C23 H27 Cl N4 O'
_chemical_formula_weight         410.93
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl Br'
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'
Cl Cl 0.3639 0.7018 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.13790(5)
_cell_length_b                   11.24899(6)
_cell_length_c                   18.30377(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2087.382(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    46096
_cell_measurement_temperature    99.99(13)
_cell_measurement_theta_max      69.6590
_cell_measurement_theta_min      4.5930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            54502
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.784
_diffrn_reflns_theta_min         4.614
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  -2.00   0.50    0.70    --  -43.75 111.00-120.00  154
  2  ω      4.00  35.00   0.50    0.70    --   45.32-111.00 145.00   62
  3  ω   -122.00 -97.00   0.50    2.50    --  -95.95-111.00 145.00   50
  4  ω    -87.00 -61.00   0.50    2.50    --  -95.95 111.00-120.00   52
  5  ω     56.00 102.00   0.50    2.50    --   97.51-111.00 145.00   92
  6  ω     90.00 152.00   0.50    2.50    --   97.51 111.00-120.00  124
  7  ω    -51.00 -12.00   0.50    0.70    --   -6.00 122.00  87.04   78
  8  ω    -50.00  -2.00   0.50    0.70    --  -10.00 110.00 -42.84   96
  9  ω    -55.00 -30.00   0.50    0.70    --   14.00 161.00 -90.89   50
 10  ω    -15.00  13.00   0.50    0.70    --   18.00 102.00-159.70   56
 11  ω     -9.00  16.00   0.50    0.70    --   26.00 101.00 -58.27   50
 12  ω     -4.00  21.00   0.50    0.70    --   30.00 100.00 129.07   50
 13  ω     -2.00  23.00   0.50    0.70    --   30.00  97.00-128.54   50
 14  ω     -4.00  21.00   0.50    0.70    --   30.00 100.00  19.03   50
 15  ω      0.00  25.00   0.50    0.70    --   30.00  96.00  89.05   50
 16  ω      2.00  27.00   0.50    0.70    --   34.00  95.00 130.77   50
 17  ω      2.00  27.00   0.50    0.70    --   34.00  96.00  44.31   50
 18  ω      2.00  27.00   0.50    0.70    --   34.00  97.00 -75.48   50
 19  ω      7.00  32.00   0.50    0.70    --   38.00  93.00-124.51   50
 20  ω    -35.00  -9.00   0.50    0.70    --  -38.00 -87.00-122.67   52
 21  ω     10.00  35.00   0.50    0.70    --   38.00  86.00 137.93   50
 22  ω    -34.00  -9.00   0.50    0.70    --  -38.00 -90.00 -92.06   50
 23  ω      8.00  33.00   0.50    0.70    --   38.00  92.00  73.19   50
 24  ω     13.00  38.00   0.50    0.70    --   42.00  88.00  14.51   50
 25  ω    -40.00 -14.00   0.50    0.70    --  -43.75 -89.00 127.40   52
 26  ω    -43.00 -17.00   0.50    0.70    --  -43.75 -87.00  15.24   52
 27  ω    -51.00 -26.00   0.50    0.70    --  -43.75 138.00 -90.00   50
 28  ω    -99.00 -57.00   0.50    0.70    --  -43.75 138.00 -90.00   84
 29  ω     43.00  69.00   0.50    0.70    --   45.32-111.00 145.00   52
 30  ω     16.00  41.00   0.50    0.70    --   46.00  91.00-129.32   50
 31  ω    -43.00 -17.00   0.50    0.70    --  -46.00 -87.00 -37.66   52
 32  ω     17.00  42.00   0.50    0.70    --   46.00  88.00 -72.75   50
 33  ω     16.00  41.00   0.50    0.70    --   46.00  92.00 144.62   50
 34  ω    -51.00 -25.00   0.50    0.70    --  -46.00 -70.00 -99.26   52
 35  ω     16.00  41.00   0.50    0.70    --   46.00  92.00-108.28   50
 36  ω     16.00  41.00   0.50    0.70    --   46.00  91.00  92.60   50
 37  ω    -41.00 -16.00   0.50    0.70    --  -46.00 -90.00 151.56   50
 38  ω     16.00  41.00   0.50    0.70    --   46.00  92.00 -48.64   50
 39  ω    -62.00 -27.00   0.50    0.70    --  -50.00 -77.00-109.99   70
 40  ω    -70.00 -27.00   0.50    0.70    --  -50.00 -71.00 -30.51   86
 41  ω     29.00  90.00   0.50    0.70    --   54.00  77.00 171.10  122
 42  ω    -54.00 -29.00   0.50    0.70    --  -54.00 -77.00 -54.19   50
 43  ω     30.00  66.00   0.50    0.70    --   54.00  77.00-145.39   72
 44  ω   -104.00 -78.00   0.50    0.70    --  -54.00 -77.00 -54.19   52
 45  ω    -59.00 -33.00   0.50    0.70    --  -54.00 -71.00 -22.19   52
 46  ω    -61.00 -35.00   0.50    0.70    --  -58.00 -73.00  87.55   52
 47  ω    -60.00 -34.00   0.50    0.70    --  -58.00 -72.00  93.15   52
 48  ω    -58.00 -33.00   0.50    0.70    --  -58.00 -76.00-176.04   50
 49  ω   -125.00 -96.00   0.50    0.70    --  -58.00 -76.00-176.04   58
 50  ω   -115.00 -75.00   0.50    0.70    --  -58.00 -76.00  74.73   80
 51  ω    -66.00 -33.00   0.50    0.70    --  -58.00 -76.00  74.73   66
 52  ω     35.00  61.00   0.50    0.70    --   58.00  75.00  56.52   52
 53  ω     95.00 120.00   0.50    0.70    --   58.00  75.00  56.52   50
 54  ω    -64.00 -34.00   0.50    0.70    --  -58.00 -75.00-134.36   60
 55  ω     38.00  64.00   0.50    0.70    --   62.00  77.00  88.07   52
 56  ω     90.00 116.00   0.50    0.70    --   62.00  77.00  88.07   52
 57  ω    -63.00 -38.00   0.50    0.70    --  -62.00 -72.00-124.85   50
 58  ω   -101.00 -37.00   0.50    0.70    --  -62.00 -76.00 -89.34  128
 59  ω    -64.00 -39.00   0.50    0.70    --  -62.00 -70.00-153.18   50
 60  ω     37.00  63.00   0.50    0.70    --   62.00  77.00-160.92   52
 61  ω     43.00  69.00   0.50    0.70    --   66.00  73.00  49.57   52
 62  ω     43.00  79.00   0.50    0.70    --   66.00  70.00  76.61   72
 63  ω     42.00  68.00   0.50    0.70    --   66.00  77.00-133.90   52
 64  ω     43.00  68.00   0.50    0.70    --   66.00  71.00  25.39   50
 65  ω    -80.00 -45.00   0.50    2.50    --  -70.00 -76.00 133.67   70
 66  ω     46.00  80.00   0.50    0.70    --   70.00  73.00 -19.51   68
 67  ω    112.00 137.00   0.50    0.70    --   70.00  75.00 -74.57   50
 68  ω     50.00  82.00   0.50    0.70    --   70.00  75.00 -74.57   64
 69  ω   -105.00 -77.00   0.50    2.50    --  -70.00 -72.00 -43.71   56
 70  ω    -84.00 -45.00   0.50    2.50    --  -70.00 -76.00 101.61   78
 71  ω    -73.00 -46.00   0.50    2.50    --  -70.00 -72.00 -43.71   54
 72  ω   -122.00 -47.00   0.50    2.50    --  -70.00 -73.00  60.97  150
 73  ω    -70.00 -45.00   0.50    2.50    --  -70.00 -77.00  88.97   50
 74  ω   -139.00 -91.00   0.50    2.50    --  -74.00 -77.00  43.68   96
 75  ω   -138.00 -49.00   0.50    2.50    --  -74.00 -77.00 -91.87  178
 76  ω   -101.00 -49.00   0.50    2.50    --  -74.00 -77.00-164.58  104
 77  ω    -89.00 -49.00   0.50    2.50    --  -74.00 -76.00 165.32   80
 78  ω    -85.00 -49.00   0.50    2.50    --  -74.00 -75.00-144.86   72
 79  ω    -84.00 -50.00   0.50    2.50    --  -74.00 -77.00  43.68   68
 80  ω    -80.00 -53.00   0.50    2.50    --  -78.00 -76.00   0.04   54
 81  ω    -82.00 -53.00   0.50    2.50    --  -78.00 -77.00 101.29   58
 82  ω    -82.00 -56.00   0.50    2.50    --  -78.00 -73.00 175.74   52
 83  ω    -83.00 -56.00   0.50    2.50    --  -78.00 -73.00  68.11   54
 84  ω    -79.00 -54.00   0.50    2.50    --  -78.00 -74.00  81.09   50
 85  ω    -95.00 -60.00   0.50    2.50    --  -82.00 -74.00 -70.20   70
 86  ω    -84.00 -58.00   0.50    2.50    --  -82.00 -74.00-113.63   52
 87  ω    -88.00 -57.00   0.50    2.50    --  -82.00 -77.00 -49.99   62
 88  ω    -88.00 -57.00   0.50    2.50    --  -82.00 -75.00  48.20   62
 89  ω   -146.00-120.00   0.50    2.50    --  -82.00 -75.00  48.20   52
 90  ω   -123.00 -57.00   0.50    2.50    --  -82.00 -77.00 -22.84  132
 91  ω    -83.00 -57.00   0.50    2.50    --  -82.00 -75.00 -13.95   52
 92  ω    -82.00 -57.00   0.50    2.50    --  -82.00 -77.00 123.89   50
 93  ω   -138.00-112.00   0.50    2.50    --  -82.00 -77.00 123.89   52
 94  ω    -91.00 -57.00   0.50    2.50    --  -82.00 -77.00 163.15   68
 95  ω   -124.00 -91.00   0.50    2.50    --  -82.00 -76.00 137.83   66
 96  ω    -83.00 -57.00   0.50    2.50    --  -82.00 -76.00 137.83   52
 97  ω    -92.00 -57.00   0.50    2.50    --  -82.00 -77.00  26.91   70
 98  ω   -153.00 -62.00   0.50    2.50    --  -86.00 -73.00 -82.24  182
 99  ω    -88.00 -62.00   0.50    2.50    --  -86.00 -73.00-120.11   52
100  ω   -103.00 -61.00   0.50    2.50    --  -86.00 -75.00 129.79   84
101  ω    -96.00 -63.00   0.50    2.50    --  -86.00 -74.00-140.43   66
102  ω   -154.00-115.00   0.50    2.50    --  -86.00 -74.00-140.43   78
103  ω    -88.00 -62.00   0.50    2.50    --  -86.00 -73.00 101.13   52
104  ω   -151.00 -93.00   0.50    2.50    --  -86.00 -73.00 101.13  116
105  ω   -101.00 -63.00   0.50    2.50    --  -86.00 -73.00   3.57   76
106  ω    -90.00 -65.00   0.50    2.50    --  -86.00 -75.00  92.73   50
107  ω    -95.00 -62.00   0.50    2.50    --  -86.00 -74.00 178.43   66
108  ω   -114.00 -66.00   0.50    2.50    --  -90.00 -72.00 163.61   96
109  ω    -96.00 -65.00   0.50    2.50    --  -90.00 -77.00-150.30   62
110  ω    -95.00 -65.00   0.50    2.50    --  -90.00 -75.00 -33.84   60
111  ω    120.00 153.00   0.50    2.50    --   90.00  75.00-141.40   66
112  ω     66.00  92.00   0.50    2.50    --   90.00  75.00-141.40   52
113  ω    -94.00 -69.00   0.50    2.50    --  -90.00 -72.00 -50.83   50
114  ω    -96.00 -70.00   0.50    2.50    --  -90.00 -63.00  58.33   52
115  ω    -93.00 -67.00   0.50    2.50    --  -90.00 -73.00-111.91   52
116  ω   -150.00-124.00   0.50    2.50    --  -90.00 -73.00-111.91   52
117  ω    -98.00 -72.00   0.50    2.50    --  -94.00 -67.00  -2.43   52
118  ω   -153.00-127.00   0.50    2.50    --  -94.00 -67.00  -2.43   52
119  ω   -123.00 -70.00   0.50    2.50    --  -94.00 -74.00  28.82  106
120  ω   -156.00-129.00   0.50    2.50    --  -94.00 -74.00  28.82   54
121  ω   -162.00 -74.00   0.50    2.50    --  -95.95 -68.00 150.00  176
122  ω   -121.00 -76.00   0.50    2.50    --  -95.95 -59.00 120.00   90
123  ω   -162.00 -77.00   0.50    2.50    --  -95.95 -68.00-180.00  170
124  ω    -82.00 -33.00   0.50    2.50    --  -95.95  96.00-120.00   98
125  ω    -72.00 -37.00   0.50    2.50    --  -95.95 117.00-180.00   70
126  ω   -110.00 -80.00   0.50    2.50    --  -95.95 117.00-180.00   60
127  ω   -105.00 -72.00   0.50    2.50    --  -95.95 -77.00  90.00   66
128  ω   -157.00-115.00   0.50    2.50    --  -95.95 -77.00  90.00   84
129  ω    -79.00 -29.00   0.50    2.50    --  -95.95  68.00-120.00  100
130  ω   -125.00 -74.00   0.50    2.50    --  -95.95 -77.00-150.00  102
131  ω   -164.00-128.00   0.50    2.50    --  -95.95 -77.00-150.00   72
132  ω   -143.00-114.00   0.50    2.50    --  -95.95 -59.00  60.00   58
133  ω    -50.00 -25.00   0.50    2.50    --  -95.95  96.00  60.00   50
134  ω   -104.00 -64.00   0.50    2.50    --  -95.95  96.00  60.00   80
135  ω    -69.00 -43.00   0.50    2.50    --  -95.95  59.00  60.00   52
136  ω   -164.00 -71.00   0.50    2.50    --  -95.95 -77.00  60.00  186
137  ω   -161.00 -92.00   0.50    2.50    --  -95.95 -33.00-150.00  138
138  ω    -97.00 -72.00   0.50    2.50    --  -95.95 -75.00-116.56   50
139  ω   -163.00-138.00   0.50    2.50    --  -95.95 -75.00-116.56   50
140  ω    -99.00 -73.00   0.50    2.50    --  -95.95 -77.00   0.00   52
141  ω    -66.00 -40.00   0.50    2.50    --  -95.95 117.00 -90.00   52
142  ω   -163.00-116.00   0.50    2.50    --  -95.95 -77.00   0.00   94
143  ω   -108.00 -81.00   0.50    2.50    --  -95.95 117.00 -90.00   54
144  ω   -164.00 -72.00   0.50    2.50    --  -95.95 -77.00 120.00  184
145  ω    -96.00 -71.00   0.50    2.50    --  -95.95 -77.00 -60.00   50
146  ω   -148.00-122.00   0.50    2.50    --  -95.95 -77.00 -60.00   52
147  ω     40.00  82.00   0.50    2.50    --   97.51-117.00 -30.00   84
148  ω     34.00  83.00   0.50    2.50    --   97.51 -68.00 120.00   98
149  ω     73.00 157.00   0.50    2.50    --   97.51  77.00 -60.00  168
150  ω     95.00 121.00   0.50    2.50    --   97.51 -86.00  90.00   52
151  ω     32.00  78.00   0.50    2.50    --   97.51 -86.00  90.00   92
152  ω     32.00  57.00   0.50    2.50    --   97.51 -50.00 -30.00   50
153  ω     36.00  96.00   0.50    2.50    --   97.51 -77.00 -30.00  120
154  ω     73.00 130.00   0.50    2.50    --   97.51  77.00-120.00  114
155  ω    125.00 156.00   0.50    2.50    --   97.51  77.00-150.00   62
156  ω     73.00 106.00   0.50    2.50    --   97.51  77.00-150.00   66
157  ω     77.00 137.00   0.50    2.50    --   97.51  68.00  60.00  120
158  ω     75.00 105.00   0.50    2.50    --   97.51  68.00 -60.00   60
159  ω     33.00 107.00   0.50    2.50    --   97.51-117.00  90.00  148
160  ω     76.00 157.00   0.50    2.50    --   97.51  77.00 -30.00  162
161  ω    113.00 138.00   0.50    2.50    --   97.51  68.00   0.00   50
162  ω     77.00 106.00   0.50    2.50    --   97.51  68.00   0.00   58
163  ω     31.00  67.00   0.50    2.50    --   97.51 -59.00 150.00   72
164  ω    112.00 153.00   0.50    2.50    --   97.51  77.00 -90.00   82
165  ω     73.00  98.00   0.50    2.50    --   97.51  77.00 -90.00   50
166  ω     67.00 106.00   0.50    2.50    --   97.51-117.00   0.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0371991000
_diffrn_orient_matrix_UB_12      0.0202507000
_diffrn_orient_matrix_UB_13      0.0806331000
_diffrn_orient_matrix_UB_21      -0.1439140000
_diffrn_orient_matrix_UB_22      0.0339075000
_diffrn_orient_matrix_UB_23      0.0171591000
_diffrn_orient_matrix_UB_31      -0.0314123000
_diffrn_orient_matrix_UB_32      -0.1311801000
_diffrn_orient_matrix_UB_33      0.0169213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3868
_reflns_number_total             3931
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.016(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.067
_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)+(0.0352P)²+0.5046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0653
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.984(13)
 0.016(13)
2. 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, All O(H,H) groups
3.a Free rotating group:
 O1(H1D,H1E)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.88951(5) 0.34680(4) 0.52192(2) 0.02890(12) Uani 1 1 d . . . . .
O1 O 0.79584(17) 0.85595(16) 0.94970(10) 0.0439(4) Uani 1 1 d G . . . .
H1D H 0.746188 0.802860 0.970646 0.066 Uiso 1 1 d G U . . .
H1E H 0.876034 0.833557 0.959553 0.066 Uiso 1 1 d G U . . .
N1 N 0.65820(15) 0.62387(13) 0.71295(8) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.77204(16) 0.53267(14) 0.62676(9) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.791568 0.495554 0.585846 0.027 Uiso 1 1 calc R U . . .
N003 N 0.53973(16) 0.52629(14) 0.61587(8) 0.0211(3) Uani 1 1 d . . . . .
N3 N 0.63449(18) 0.80938(14) 0.61232(8) 0.0261(4) Uani 1 1 d . . . . .
C1 C 0.41506(18) 0.50509(18) 0.65478(11) 0.0245(4) Uani 1 1 d . . . . .
H1A H 0.353453 0.570085 0.644444 0.037 Uiso 1 1 calc R U . . .
H1B H 0.431941 0.501339 0.707448 0.037 Uiso 1 1 calc R U . . .
H1C H 0.376675 0.429714 0.638385 0.037 Uiso 1 1 calc R U . . .
C2 C 0.5527(2) 0.47082(18) 0.54349(10) 0.0253(4) Uani 1 1 d . . . . .
H2A H 0.599976 0.395190 0.548178 0.038 Uiso 1 1 calc R U . . .
H2B H 0.602062 0.523955 0.511023 0.038 Uiso 1 1 calc R U . . .
H2C H 0.464875 0.456342 0.523026 0.038 Uiso 1 1 calc R U . . .
C3 C 0.64965(18) 0.55999(16) 0.64977(10) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.79212(18) 0.63046(17) 0.73291(10) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.85236(19) 0.67876(17) 0.79389(11) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.803670 0.719790 0.830374 0.030 Uiso 1 1 calc R U . . .
C6 C 0.9886(2) 0.66378(19) 0.79876(12) 0.0302(4) Uani 1 1 d . . . . .
H6 H 1.034223 0.695120 0.839820 0.036 Uiso 1 1 calc R U . . .
C7 C 1.0599(2) 0.6037(2) 0.74467(12) 0.0321(5) Uani 1 1 d . . . . .
H7 H 1.152486 0.594346 0.750292 0.039 Uiso 1 1 calc R U . . .
C8 C 0.99861(19) 0.55740(19) 0.68282(12) 0.0282(4) Uani 1 1 d . . . . .
H8 H 1.046885 0.517486 0.645712 0.034 Uiso 1 1 calc R U . . .
C9 C 0.86290(19) 0.57285(16) 0.67846(11) 0.0227(4) Uani 1 1 d . . . . .
C10 C 0.55247(18) 0.68730(16) 0.74803(10) 0.0193(4) Uani 1 1 d . . . . .
C11 C 0.52600(19) 0.65801(18) 0.81918(10) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.585058 0.608032 0.845272 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4119(2) 0.70147(17) 0.85389(11) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.396911 0.686194 0.904253 0.032 Uiso 1 1 calc R U . . .
C13 C 0.32294(19) 0.76594(18) 0.81417(11) 0.0265(4) Uani 1 1 d . . . . .
H13 H 0.241983 0.788881 0.836173 0.032 Uiso 1 1 calc R U . . .
C14 C 0.34877(19) 0.79936(17) 0.74083(11) 0.0241(4) Uani 1 1 d . . . . .
C15 C 0.2524(2) 0.86047(19) 0.69930(12) 0.0315(5) Uani 1 1 d . . . . .
H15 H 0.168732 0.877920 0.720110 0.038 Uiso 1 1 calc R U . . .
C16 C 0.2798(2) 0.8942(2) 0.62946(13) 0.0366(5) Uani 1 1 d . . . . .
H16 H 0.212729 0.929862 0.600607 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4063(2) 0.87681(18) 0.59943(11) 0.0317(5) Uani 1 1 d . . . . .
H17 H 0.424883 0.906095 0.551842 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5035(2) 0.81835(16) 0.63759(10) 0.0230(4) Uani 1 1 d . . . . .
C19 C 0.47181(19) 0.76875(16) 0.70807(10) 0.0199(4) Uani 1 1 d . . . . .
C20 C 0.6629(3) 0.8332(2) 0.53506(11) 0.0403(6) Uani 1 1 d . . . . .
H20A H 0.634629 0.914046 0.520613 0.048 Uiso 1 1 calc R U . . .
H20B H 0.620304 0.773983 0.502715 0.048 Uiso 1 1 calc R U . . .
C21 C 0.8126(3) 0.8210(2) 0.53416(13) 0.0501(7) Uani 1 1 d . . . . .
H21A H 0.850947 0.863796 0.491939 0.060 Uiso 1 1 calc R U . . .
H21B H 0.839007 0.736405 0.531609 0.060 Uiso 1 1 calc R U . . .
C22 C 0.8577(3) 0.8774(2) 0.60674(13) 0.0424(6) Uani 1 1 d . . . . .
H22A H 0.924275 0.826997 0.631313 0.051 Uiso 1 1 calc R U . . .
H22B H 0.895597 0.957414 0.598497 0.051 Uiso 1 1 calc R U . . .
C23 C 0.7303(2) 0.88503(18) 0.65229(11) 0.0261(4) Uani 1 1 d . . . . .
H23A H 0.745026 0.854514 0.702360 0.031 Uiso 1 1 calc R U . . .
H23B H 0.698555 0.968100 0.655343 0.031 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
O1 H1D 0.8701 . ?
O1 H1E 0.8701 . ?
N1 C3 1.364(2) . ?
N1 C4 1.408(2) . ?
N1 C10 1.439(2) . ?
N2 H2 0.8800 . ?
N2 C3 1.346(2) . ?
N2 C9 1.396(3) . ?
N003 C1 1.470(2) . ?
N003 C2 1.470(2) . ?
N003 C3 1.331(2) . ?
N3 C18 1.410(3) . ?
N3 C20 1.468(2) . ?
N3 C23 1.484(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 C5 1.383(3) . ?
C4 C9 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C10 C11 1.370(3) . ?
C10 C19 1.429(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.407(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.367(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.418(3) . ?
C14 C15 1.416(3) . ?
C14 C19 1.426(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.362(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.409(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(3) . ?
C18 C19 1.442(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.523(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.542(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.539(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 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
H1D O1 H1E 104.5 . . ?
C3 N1 C4 108.00(15) . . ?
C3 N1 C10 126.31(16) . . ?
C4 N1 C10 125.20(15) . . ?
C3 N2 H2 125.6 . . ?
C3 N2 C9 108.80(16) . . ?
C9 N2 H2 125.6 . . ?
C1 N003 C2 116.41(15) . . ?
C3 N003 C1 122.70(15) . . ?
C3 N003 C2 117.77(16) . . ?
C18 N3 C20 119.21(18) . . ?
C18 N3 C23 114.45(15) . . ?
C20 N3 C23 104.00(16) . . ?
N003 C1 H1A 109.5 . . ?
N003 C1 H1B 109.5 . . ?
N003 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N003 C2 H2A 109.5 . . ?
N003 C2 H2B 109.5 . . ?
N003 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 N1 109.09(16) . . ?
N003 C3 N1 126.77(17) . . ?
N003 C3 N2 124.13(16) . . ?
C5 C4 N1 130.98(17) . . ?
C5 C4 C9 122.30(18) . . ?
C9 C4 N1 106.70(16) . . ?
C4 C5 H5 121.9 . . ?
C4 C5 C6 116.19(19) . . ?
C6 C5 H5 121.9 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.6(2) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.69(19) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 121.9 . . ?
C9 C8 C7 116.2(2) . . ?
C9 C8 H8 121.9 . . ?
C4 C9 N2 107.26(16) . . ?
C4 C9 C8 121.93(19) . . ?
C8 C9 N2 130.70(19) . . ?
C11 C10 N1 116.80(17) . . ?
C11 C10 C19 121.91(17) . . ?
C19 C10 N1 121.05(16) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.43(18) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.12(18) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.49(18) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C19 119.70(18) . . ?
C15 C14 C13 120.62(19) . . ?
C15 C14 C19 119.67(18) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.34(19) . . ?
C18 C17 H17 119.3 . . ?
N3 C18 C19 118.40(17) . . ?
C17 C18 N3 122.83(18) . . ?
C17 C18 C19 118.70(19) . . ?
C10 C19 C18 125.34(17) . . ?
C14 C19 C10 116.10(17) . . ?
C14 C19 C18 118.53(17) . . ?
N3 C20 H20A 111.6 . . ?
N3 C20 H20B 111.6 . . ?
N3 C20 C21 100.9(2) . . ?
H20A C20 H20B 109.4 . . ?
C21 C20 H20A 111.6 . . ?
C21 C20 H20B 111.6 . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
C20 C21 C22 104.43(19) . . ?
H21A C21 H21B 108.9 . . ?
C22 C21 H21A 110.9 . . ?
C22 C21 H21B 110.9 . . ?
C21 C22 H22A 111.0 . . ?
C21 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
C23 C22 C21 103.9(2) . . ?
C23 C22 H22A 111.0 . . ?
C23 C22 H22B 111.0 . . ?
N3 C23 C22 104.49(16) . . ?
N3 C23 H23A 110.9 . . ?
N3 C23 H23B 110.9 . . ?
C22 C23 H23A 110.9 . . ?
C22 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?

_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 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.897
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.984(13)
2 0.016(13)

