# Supplementary Information (SI) for RSC Medicinal 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_20JLR006_KM-028-02
_database_code_depnum_ccdc_archive 'CCDC 2482160'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;
_audit_creation_date             2020-06-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl), C10 H20 N2'
_chemical_formula_sum            'C10 H20 Cl2 N2'
_chemical_formula_weight         239.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C80 H160 Cl16 N16 '
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'

_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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   13.2264(2)
_cell_length_b                   10.8785(2)
_cell_length_c                   16.7754(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2413.70(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7681
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.5430
_cell_measurement_theta_min      5.2950
_shelx_estimated_absorpt_T_max   0.741
_shelx_estimated_absorpt_T_min   0.448
_exptl_absorpt_coefficient_mu    4.553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.72a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14194
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.837
_diffrn_reflns_theta_min         5.274
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  -4.00   1.00    0.25    --  -21.00 114.00 -24.00   58
  2  ω    -93.00 -43.00   1.00    0.25    --  -21.00-173.00 105.00   50
  3  ω     27.00  91.00   1.00    0.25    --   47.89-114.00-114.00   64
  4  ω    102.00 171.00   1.00    1.00    --  106.80 114.00 -24.00   69
  5  ω     35.00 109.00   1.00    1.00    --  106.80-114.00-114.00   74
  6  ω    -93.00   2.00   1.00    0.25    --  -21.00 -77.00-120.00   95
  7  ω    -23.00  63.00   1.00    0.25    --   47.89 -57.00-150.00   86
  8  ω    -26.00  23.00   1.00    0.25    --   47.89 -19.00  60.00   49
  9  ω     35.00 102.00   1.00    1.00    --  106.80 -77.00 -90.00   67
 10  ω     95.00 171.00   1.00    1.00    --  106.80  45.00-120.00   76
 11  ω     35.00  68.00   1.00    1.00    --  106.80 -61.00  60.00   33
 12  ω     35.00 102.00   1.00    1.00    --  106.80 -77.00   0.00   67
 13  ω     95.00 171.00   1.00    1.00    --  106.80  30.00 150.00   76
 14  ω     35.00  68.00   1.00    1.00    --  106.80 -61.00 120.00   33
 15  ω     35.00  68.00   1.00    1.00    --  106.80 -61.00  90.00   33
 16  ω     26.00 119.00   1.00    0.25    --   47.89  77.00 -30.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0270499000
_diffrn_orient_matrix_UB_12      -0.1284929000
_diffrn_orient_matrix_UB_13      -0.0321875000
_diffrn_orient_matrix_UB_21      0.0108763000
_diffrn_orient_matrix_UB_22      -0.0536234000
_diffrn_orient_matrix_UB_23      0.0845267000
_diffrn_orient_matrix_UB_31      -0.1127973000
_diffrn_orient_matrix_UB_32      0.0257318000
_diffrn_orient_matrix_UB_33      0.0158636000
_diffrn_oxdiff_digest_frames     
;
01ea111f80f385a60176d85528528a1426010235118
;
_diffrn_oxdiff_digest_hkl        
;
01aaa987d16f0849f93a55d27b33bebd8c58e5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2198
_reflns_number_total             2492
_reflns_odcompleteness_completeness 99.96
_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 1.171.41.72a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.72a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.72a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.085
_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)+(0.0749P)²+1.9536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1453
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 N10(H10A,H10B), C6(H6A,H6B), C12(H12A,H12B), C3(H3A,H3B), C7(H7A,H7B),
 C11(H11A,H11B), C8(H8A,H8B), C2(H2A,H2B)
;
_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
Cl2 Cl 0.60021(5) 0.18652(6) 0.60303(4) 0.0400(2) Uani 1 1 d . . . . .
Cl1 Cl 0.33383(5) 0.46321(6) 0.64687(4) 0.0453(2) Uani 1 1 d . . . . .
N1 N 0.41081(17) 0.2811(2) 0.51642(14) 0.0379(5) Uani 1 1 d . . . . .
N10 N 0.55387(16) 0.3074(2) 0.28306(12) 0.0355(5) Uani 1 1 d . . . . .
H10A H 0.5711 0.3001 0.2307 0.043 Uiso 1 1 calc R . . . .
H10B H 0.5641 0.3867 0.2984 0.043 Uiso 1 1 calc R . . . .
C4 C 0.44316(17) 0.2312(2) 0.38207(14) 0.0300(5) Uani 1 1 d . . . . .
C5 C 0.44161(17) 0.3410(2) 0.44001(14) 0.0303(5) Uani 1 1 d . . . . .
H5 H 0.5107 0.3776 0.4450 0.036 Uiso 1 1 calc R . . . .
C9 C 0.44485(18) 0.2721(2) 0.29512(15) 0.0347(5) Uani 1 1 d . . . . .
H9 H 0.4292 0.1996 0.2606 0.042 Uiso 1 1 calc R . . . .
C6 C 0.36500(18) 0.4392(2) 0.41697(16) 0.0347(5) Uani 1 1 d . . . . .
H6A H 0.3714 0.5099 0.4538 0.042 Uiso 1 1 calc R . . . .
H6B H 0.2959 0.4054 0.4226 0.042 Uiso 1 1 calc R . . . .
C12 C 0.54227(19) 0.1560(2) 0.38804(16) 0.0378(6) Uani 1 1 d . . . . .
H12A H 0.5677 0.1549 0.4435 0.045 Uiso 1 1 calc R . . . .
H12B H 0.5313 0.0702 0.3702 0.045 Uiso 1 1 calc R . . . .
C3 C 0.3494(2) 0.1585(2) 0.40736(17) 0.0406(6) Uani 1 1 d . . . . .
H3A H 0.2884 0.1898 0.3799 0.049 Uiso 1 1 calc R . . . .
H3B H 0.3576 0.0702 0.3946 0.049 Uiso 1 1 calc R . . . .
C7 C 0.3804(2) 0.4834(2) 0.33150(17) 0.0408(6) Uani 1 1 d . . . . .
H7A H 0.3283 0.5454 0.3182 0.049 Uiso 1 1 calc R . . . .
H7B H 0.4475 0.5229 0.3266 0.049 Uiso 1 1 calc R . . . .
C11 C 0.6167(2) 0.2219(3) 0.33308(17) 0.0406(6) Uani 1 1 d . . . . .
H11A H 0.6669 0.2686 0.3646 0.049 Uiso 1 1 calc R . . . .
H11B H 0.6529 0.1621 0.2990 0.049 Uiso 1 1 calc R . . . .
C8 C 0.3734(2) 0.3764(3) 0.27342(16) 0.0418(6) Uani 1 1 d . . . . .
H8A H 0.3896 0.4060 0.2191 0.050 Uiso 1 1 calc R . . . .
H8B H 0.3031 0.3450 0.2728 0.050 Uiso 1 1 calc R . . . .
C2 C 0.3409(2) 0.1775(3) 0.4970(2) 0.0529(8) Uani 1 1 d . . . . .
H2A H 0.2706 0.1986 0.5119 0.063 Uiso 1 1 calc R . . . .
H2B H 0.3610 0.1021 0.5259 0.063 Uiso 1 1 calc R . . . .
H1A H 0.377(2) 0.334(3) 0.5517(18) 0.039(8) Uiso 1 1 d . . . . .
H1B H 0.461(3) 0.249(4) 0.541(2) 0.063(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.495(3) . ?
N1 C2 1.494(4) . ?
N1 H1A 0.94(3) . ?
N1 H1B 0.86(4) . ?
N10 H10A 0.9100 . ?
N10 H10B 0.9100 . ?
N10 C9 1.506(3) . ?
N10 C11 1.503(3) . ?
C4 C5 1.540(3) . ?
C4 C9 1.525(4) . ?
C4 C12 1.549(3) . ?
C4 C3 1.531(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.522(3) . ?
C9 H9 1.0000 . ?
C9 C8 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.526(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.527(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.522(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 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
C5 N1 H1A 113.7(19) . . ?
C5 N1 H1B 112(2) . . ?
C2 N1 C5 108.1(2) . . ?
C2 N1 H1A 107.8(19) . . ?
C2 N1 H1B 106(3) . . ?
H1A N1 H1B 108(3) . . ?
H10A N10 H10B 108.5 . . ?
C9 N10 H10A 110.3 . . ?
C9 N10 H10B 110.3 . . ?
C11 N10 H10A 110.3 . . ?
C11 N10 H10B 110.3 . . ?
C11 N10 C9 107.2(2) . . ?
C5 C4 C12 112.36(19) . . ?
C9 C4 C5 112.19(19) . . ?
C9 C4 C12 101.75(19) . . ?
C9 C4 C3 115.3(2) . . ?
C3 C4 C5 102.43(19) . . ?
C3 C4 C12 113.2(2) . . ?
N1 C5 C4 101.92(19) . . ?
N1 C5 H5 110.5 . . ?
N1 C5 C6 110.0(2) . . ?
C4 C5 H5 110.5 . . ?
C6 C5 C4 113.13(19) . . ?
C6 C5 H5 110.5 . . ?
N10 C9 C4 102.53(19) . . ?
N10 C9 H9 108.7 . . ?
N10 C9 C8 111.9(2) . . ?
C4 C9 H9 108.7 . . ?
C8 C9 C4 115.9(2) . . ?
C8 C9 H9 108.7 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.8(2) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C4 C12 H12A 110.8 . . ?
C4 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
C11 C12 C4 104.9(2) . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C2 C3 C4 105.3(2) . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.7(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
N10 C11 C12 105.8(2) . . ?
N10 C11 H11A 110.6 . . ?
N10 C11 H11B 110.6 . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 C9 112.3(2) . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N1 C2 C3 105.8(2) . . ?
N1 C2 H2A 110.6 . . ?
N1 C2 H2B 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C6 C7 -167.7(2) . . . . ?
N10 C9 C8 C7 -68.9(3) . . . . ?
C4 C5 C6 C7 -54.5(3) . . . . ?
C4 C9 C8 C7 48.2(3) . . . . ?
C4 C12 C11 N10 -14.3(3) . . . . ?
C4 C3 C2 N1 13.5(3) . . . . ?
C5 N1 C2 C3 12.6(3) . . . . ?
C5 C4 C9 N10 78.4(2) . . . . ?
C5 C4 C9 C8 -43.8(3) . . . . ?
C5 C4 C12 C11 -85.3(2) . . . . ?
C5 C4 C3 C2 -33.4(3) . . . . ?
C5 C6 C7 C8 57.7(3) . . . . ?
C9 N10 C11 C12 -12.3(3) . . . . ?
C9 C4 C5 N1 164.59(19) . . . . ?
C9 C4 C5 C6 46.5(3) . . . . ?
C9 C4 C12 C11 34.9(2) . . . . ?
C9 C4 C3 C2 -155.5(2) . . . . ?
C6 C7 C8 C9 -53.8(3) . . . . ?
C12 C4 C5 N1 -81.5(2) . . . . ?
C12 C4 C5 C6 160.4(2) . . . . ?
C12 C4 C9 N10 -41.9(2) . . . . ?
C12 C4 C9 C8 -164.1(2) . . . . ?
C12 C4 C3 C2 87.9(3) . . . . ?
C3 C4 C5 N1 40.3(2) . . . . ?
C3 C4 C5 C6 -77.7(2) . . . . ?
C3 C4 C9 N10 -164.9(2) . . . . ?
C3 C4 C9 C8 73.0(3) . . . . ?
C3 C4 C12 C11 159.2(2) . . . . ?
C11 N10 C9 C4 34.3(2) . . . . ?
C11 N10 C9 C8 159.1(2) . . . . ?
C2 N1 C5 C4 -33.1(2) . . . . ?
C2 N1 C5 C6 87.1(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 2.442
_oxdiff_exptl_absorpt_empirical_full_min 0.417
####################################################################### 
# 
# 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_22JLR010_KM-120-01-F1
_database_code_depnum_ccdc_archive 'CCDC 2482164'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;

_audit_creation_date             2022-07-22T11:51:53-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H23 N5 O2 S'
_chemical_formula_sum            'C16 H23 N5 O2 S'
_chemical_formula_weight         349.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.34716(11)
_cell_length_b                   11.19722(7)
_cell_length_c                   20.29496(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.8741(6)
_cell_angle_gamma                90
_cell_volume                     3445.85(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    172.9(2)
_cell_measurement_reflns_used    28086
_cell_measurement_theta_min      2.255
_cell_measurement_theta_max      31.592

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.146
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.1364
1 0 0 0.108
1 0 -1 0.1129
0 0 -1 0.0916
0 0 1 0.1099
-1 1 1 0.0956
1 -1 -1 0.084
-1 1 0 0.0779
1 -1 0 0.0683
-1 1 -1 0.0865
1 -1 1 0.0983
0 1 1 0.1106
0 -1 -1 0.0871
0 1 0 0.0883
0 -1 0 0.0696
0 1 -1 0.101
0 -1 1 0.0789
-1 -1 -1 0.0653
1 1 1 0.1173
1 1 0 0.097
-1 -1 0 0.0641
1 1 -1 0.1104
-1 -1 1 0.0777
5 5 -27 0.0941
9 -4 23 0.1216
-9 -5 26 0.0985
-21 0 0 0.088
-17 -4 20 0.0995


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
        Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.97

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      172.9(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0000836
_diffrn_orient_matrix_ub_12      -0.0605636
_diffrn_orient_matrix_ub_13      -0.0102443
_diffrn_orient_matrix_ub_21      -0.0406861
_diffrn_orient_matrix_ub_22      -0.0092456
_diffrn_orient_matrix_ub_23      0.0117254
_diffrn_orient_matrix_ub_31      -0.0230504
_diffrn_orient_matrix_ub_32      0.0161388
_diffrn_orient_matrix_ub_33      -0.0317654
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_number            51621
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.031
_diffrn_reflns_theta_max         31.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             5507
_reflns_number_gt                5041
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+2.3289P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5507
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   SQUEEZE                                                  #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S1 S 0.84197(2) 0.58198(2) 0.52003(2) 0.01915(7) Uani 1 1 d . . . . .
O1 O 0.92421(5) 0.54429(8) 0.55722(4) 0.02793(16) Uani 1 1 d . . . . .
O2 O 0.84124(6) 0.68481(8) 0.47743(4) 0.03307(19) Uani 1 1 d . . . . .
N3 N 0.52232(6) 0.64911(8) 0.95769(4) 0.02269(17) Uani 1 1 d . . . . .
N4 N 0.55939(6) 0.44780(8) 0.93230(4) 0.02255(17) Uani 1 1 d . . . . .
N5 N 0.62678(6) 0.42933(8) 0.83336(4) 0.02328(17) Uani 1 1 d . . . . .
N2 N 0.65653(6) 0.58699(8) 0.76783(4) 0.02330(17) Uani 1 1 d . . . . .
N1 N 0.77496(6) 0.61251(8) 0.57130(4) 0.02277(17) Uani 1 1 d . . . . .
C12 C 0.58495(6) 0.62475(8) 0.86547(5) 0.01930(17) Uani 1 1 d . . . . .
C11 C 0.62266(6) 0.54850(9) 0.82168(5) 0.01977(17) Uani 1 1 d . . . . .
C15 C 0.55558(6) 0.56627(9) 0.91954(5) 0.01942(17) Uani 1 1 d . . . . .
C7 C 0.75675(7) 0.59122(9) 0.69004(5) 0.01992(17) Uani 1 1 d . . . . .
C6 C 0.70357(7) 0.50668(9) 0.72853(5) 0.02032(18) Uani 1 1 d . . . . .
C13 C 0.56743(7) 0.74964(9) 0.87336(5) 0.02360(19) Uani 1 1 d . . . . .
C3 C 0.75661(7) 0.52848(9) 0.62274(5) 0.02076(18) Uani 1 1 d . . . . .
C16 C 0.59521(7) 0.38734(9) 0.88678(5) 0.0241(2) Uani 1 1 d . . . . .
C9 C 0.69979(8) 0.70561(9) 0.68312(5) 0.0255(2) Uani 1 1 d . . . . .
C14 C 0.52915(7) 0.76028(9) 0.92968(5) 0.0245(2) Uani 1 1 d . . . . .
C10 C 0.66073(8) 0.71177(9) 0.74796(5) 0.0252(2) Uani 1 1 d . . . . .
C8 C 0.84975(8) 0.61444(12) 0.72596(6) 0.0315(2) Uani 1 1 d . . . . .
C4 C 0.66707(8) 0.46560(11) 0.60785(5) 0.0288(2) Uani 1 1 d . . . . .
C5 C 0.64359(8) 0.43164(10) 0.67604(5) 0.0274(2) Uani 1 1 d . . . . .
C2 C 0.79682(8) 0.45904(12) 0.47123(6) 0.0306(2) Uani 1 1 d . . . . .
C1 C 0.84787(10) 0.43143(15) 0.41466(7) 0.0420(3) Uani 1 1 d . . . . .
H6 H 0.7418(9) 0.4570(12) 0.7599(7) 0.020(3) Uiso 1 1 d . . . . .
H3A H 0.8068(9) 0.4691(12) 0.6276(7) 0.021(3) Uiso 1 1 d . . . . .
H10A H 0.6009(10) 0.7463(13) 0.7401(7) 0.031(4) Uiso 1 1 d . . . . .
H10B H 0.7003(10) 0.7571(14) 0.7829(8) 0.035(4) Uiso 1 1 d . . . . .
H3 H 0.4996(11) 0.6308(14) 0.9928(8) 0.036(4) Uiso 1 1 d . . . . .
H16 H 0.5984(9) 0.3028(13) 0.8928(7) 0.026(3) Uiso 1 1 d . . . . .
H1 H 0.7348(11) 0.6572(16) 0.5560(9) 0.044(5) Uiso 1 1 d . . . . .
H13 H 0.5785(10) 0.8166(14) 0.8453(8) 0.032(4) Uiso 1 1 d . . . . .
H2A H 0.7356(12) 0.4809(16) 0.4544(9) 0.045(5) Uiso 1 1 d . . . . .
H9A H 0.7341(11) 0.7762(16) 0.6764(8) 0.043(4) Uiso 1 1 d . . . . .
H9B H 0.6505(10) 0.7010(14) 0.6449(8) 0.032(4) Uiso 1 1 d . . . . .
H4A H 0.6675(12) 0.3987(16) 0.5778(9) 0.045(5) Uiso 1 1 d . . . . .
H4B H 0.6210(12) 0.5232(17) 0.5829(9) 0.049(5) Uiso 1 1 d . . . . .
H5A H 0.6566(12) 0.3437(18) 0.6867(9) 0.053(5) Uiso 1 1 d . . . . .
H8A H 0.8828(11) 0.5373(16) 0.7354(8) 0.041(4) Uiso 1 1 d . . . . .
H14 H 0.5087(10) 0.8277(13) 0.9486(7) 0.029(4) Uiso 1 1 d . . . . .
H8B H 0.8483(12) 0.6502(17) 0.7708(9) 0.050(5) Uiso 1 1 d . . . . .
H8C H 0.8797(12) 0.6656(16) 0.6994(9) 0.047(5) Uiso 1 1 d . . . . .
H2B H 0.7964(12) 0.3863(17) 0.5005(10) 0.050(5) Uiso 1 1 d . . . . .
H5B H 0.5837(12) 0.4441(16) 0.6790(9) 0.045(5) Uiso 1 1 d . . . . .
H1A H 0.8473(13) 0.5022(19) 0.3824(11) 0.062(6) Uiso 1 1 d . . . . .
H1B H 0.8208(14) 0.3628(19) 0.3893(11) 0.061(6) Uiso 1 1 d . . . . .
H1C H 0.9098(13) 0.4092(16) 0.4319(10) 0.051(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4307(8) . ?
S1 O2 1.4389(8) . ?
S1 N1 1.6085(8) . ?
S1 C2 1.7734(12) . ?
N3 C15 1.3573(12) . ?
N3 C14 1.3791(13) . ?
N3 H3 0.864(17) . ?
N4 C15 1.3512(13) . ?
N4 C16 1.3306(13) . ?
N5 C11 1.3551(12) . ?
N5 C16 1.3391(12) . ?
N2 C11 1.3510(12) . ?
N2 C6 1.4642(12) . ?
N2 C10 1.4584(13) . ?
N1 C3 1.4646(12) . ?
N1 H1 0.817(18) . ?
C12 C11 1.4186(13) . ?
C12 C15 1.4103(12) . ?
C12 C13 1.4376(14) . ?
C7 C6 1.5393(13) . ?
C7 C3 1.5355(13) . ?
C7 C9 1.5449(14) . ?
C7 C8 1.5216(15) . ?
C6 C5 1.5446(15) . ?
C6 H6 0.971(14) . ?
C13 C14 1.3686(13) . ?
C13 H13 0.972(16) . ?
C3 C4 1.5321(15) . ?
C3 H3A 1.011(14) . ?
C16 H16 0.955(15) . ?
C9 C10 1.5294(14) . ?
C9 H9A 0.971(18) . ?
C9 H9B 0.998(15) . ?
C14 H14 0.924(15) . ?
C10 H10A 0.987(15) . ?
C10 H10B 0.999(16) . ?
C8 H8A 1.005(17) . ?
C8 H8B 0.997(19) . ?
C8 H8C 0.953(19) . ?
C4 C5 1.5309(15) . ?
C4 H4A 0.966(18) . ?
C4 H4B 1.030(19) . ?
C5 H5A 1.02(2) . ?
C5 H5B 0.941(18) . ?
C2 C1 1.5182(17) . ?
C2 H2A 0.979(18) . ?
C2 H2B 1.009(19) . ?
C1 H1A 1.03(2) . ?
C1 H1B 0.98(2) . ?
C1 H1C 0.99(2) . ?

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
O1 S1 O2 118.52(5) . . ?
O1 S1 N1 108.75(5) . . ?
O1 S1 C2 107.61(6) . . ?
O2 S1 N1 105.79(5) . . ?
O2 S1 C2 108.63(6) . . ?
N1 S1 C2 107.01(5) . . ?
C15 N3 C14 108.82(8) . . ?
C15 N3 H3 122.9(11) . . ?
C14 N3 H3 128.3(11) . . ?
C16 N4 C15 112.14(8) . . ?
C16 N5 C11 118.32(9) . . ?
C11 N2 C6 121.89(8) . . ?
C11 N2 C10 124.63(8) . . ?
C10 N2 C6 113.02(7) . . ?
S1 N1 H1 113.9(12) . . ?
C3 N1 S1 122.48(7) . . ?
C3 N1 H1 116.6(12) . . ?
C11 C12 C13 139.17(9) . . ?
C15 C12 C11 114.72(9) . . ?
C15 C12 C13 106.09(8) . . ?
N5 C11 C12 119.71(8) . . ?
N2 C11 N5 116.25(8) . . ?
N2 C11 C12 124.04(9) . . ?
N3 C15 C12 108.66(8) . . ?
N4 C15 N3 124.80(8) . . ?
N4 C15 C12 126.54(9) . . ?
C6 C7 C9 102.65(8) . . ?
C3 C7 C6 104.01(8) . . ?
C3 C7 C9 112.05(8) . . ?
C8 C7 C6 113.18(8) . . ?
C8 C7 C3 112.14(8) . . ?
C8 C7 C9 112.19(9) . . ?
N2 C6 C7 104.09(8) . . ?
N2 C6 C5 114.73(9) . . ?
N2 C6 H6 107.0(8) . . ?
C7 C6 C5 106.90(8) . . ?
C7 C6 H6 111.8(8) . . ?
C5 C6 H6 112.1(8) . . ?
C12 C13 H13 129.2(9) . . ?
C14 C13 C12 106.83(9) . . ?
C14 C13 H13 124.0(9) . . ?
N1 C3 C7 111.47(8) . . ?
N1 C3 C4 114.83(9) . . ?
N1 C3 H3A 105.4(8) . . ?
C7 C3 H3A 108.5(8) . . ?
C4 C3 C7 105.30(8) . . ?
C4 C3 H3A 111.3(8) . . ?
N4 C16 N5 128.55(10) . . ?
N4 C16 H16 115.7(9) . . ?
N5 C16 H16 115.8(9) . . ?
C7 C9 H9A 112.0(10) . . ?
C7 C9 H9B 112.2(9) . . ?
C10 C9 C7 104.52(8) . . ?
C10 C9 H9A 112.2(10) . . ?
C10 C9 H9B 108.7(9) . . ?
H9A C9 H9B 107.2(13) . . ?
N3 C14 H14 120.9(9) . . ?
C13 C14 N3 109.59(9) . . ?
C13 C14 H14 129.5(9) . . ?
N2 C10 C9 103.57(8) . . ?
N2 C10 H10A 109.9(9) . . ?
N2 C10 H10B 109.8(9) . . ?
C9 C10 H10A 110.9(9) . . ?
C9 C10 H10B 111.0(9) . . ?
H10A C10 H10B 111.5(12) . . ?
C7 C8 H8A 110.7(10) . . ?
C7 C8 H8B 110.8(11) . . ?
C7 C8 H8C 109.3(11) . . ?
H8A C8 H8B 104.7(14) . . ?
H8A C8 H8C 110.5(15) . . ?
H8B C8 H8C 110.8(15) . . ?
C3 C4 H4A 112.8(11) . . ?
C3 C4 H4B 109.6(10) . . ?
C5 C4 C3 105.36(9) . . ?
C5 C4 H4A 113.8(11) . . ?
C5 C4 H4B 111.1(11) . . ?
H4A C4 H4B 104.2(14) . . ?
C6 C5 H5A 107.6(11) . . ?
C6 C5 H5B 111.1(11) . . ?
C4 C5 C6 106.86(8) . . ?
C4 C5 H5A 111.4(10) . . ?
C4 C5 H5B 112.9(11) . . ?
H5A C5 H5B 106.9(15) . . ?
S1 C2 H2A 105.7(10) . . ?
S1 C2 H2B 109.6(11) . . ?
C1 C2 S1 112.19(10) . . ?
C1 C2 H2A 111.5(11) . . ?
C1 C2 H2B 109.4(11) . . ?
H2A C2 H2B 108.3(15) . . ?
C2 C1 H1A 111.8(12) . . ?
C2 C1 H1B 109.3(12) . . ?
C2 C1 H1C 111.2(11) . . ?
H1A C1 H1B 107.9(17) . . ?
H1A C1 H1C 109.3(16) . . ?
H1B C1 H1C 107.1(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C3 C7 135.79(8) . . . . ?
S1 N1 C3 C4 -104.58(10) . . . . ?
O1 S1 N1 C3 -52.42(10) . . . . ?
O1 S1 C2 C1 -70.71(11) . . . . ?
O2 S1 N1 C3 179.26(9) . . . . ?
O2 S1 C2 C1 58.77(11) . . . . ?
N2 C6 C5 C4 119.14(10) . . . . ?
N1 S1 C2 C1 172.56(10) . . . . ?
N1 C3 C4 C5 -154.61(9) . . . . ?
C12 C13 C14 N3 0.41(13) . . . . ?
C11 N5 C16 N4 -0.51(18) . . . . ?
C11 N2 C6 C7 -160.94(9) . . . . ?
C11 N2 C6 C5 82.60(12) . . . . ?
C11 N2 C10 C9 -177.24(10) . . . . ?
C11 C12 C15 N3 179.18(9) . . . . ?
C11 C12 C15 N4 -0.71(15) . . . . ?
C11 C12 C13 C14 -179.01(12) . . . . ?
C15 N3 C14 C13 -0.34(13) . . . . ?
C15 N4 C16 N5 0.76(17) . . . . ?
C15 C12 C11 N5 0.95(14) . . . . ?
C15 C12 C11 N2 -178.45(10) . . . . ?
C15 C12 C13 C14 -0.33(12) . . . . ?
C7 C6 C5 C4 4.30(12) . . . . ?
C7 C3 C4 C5 -31.61(11) . . . . ?
C7 C9 C10 N2 -28.16(11) . . . . ?
C6 N2 C11 N5 -6.43(15) . . . . ?
C6 N2 C11 C12 172.99(10) . . . . ?
C6 N2 C10 C9 10.42(12) . . . . ?
C6 C7 C3 N1 159.10(8) . . . . ?
C6 C7 C3 C4 33.98(10) . . . . ?
C6 C7 C9 C10 35.10(11) . . . . ?
C13 C12 C11 N5 179.55(12) . . . . ?
C13 C12 C11 N2 0.2(2) . . . . ?
C13 C12 C15 N3 0.13(11) . . . . ?
C13 C12 C15 N4 -179.76(10) . . . . ?
C3 C7 C6 N2 -145.27(8) . . . . ?
C3 C7 C6 C5 -23.46(10) . . . . ?
C3 C7 C9 C10 146.11(9) . . . . ?
C3 C4 C5 C6 16.71(12) . . . . ?
C16 N4 C15 N3 -179.96(10) . . . . ?
C16 N4 C15 C12 -0.09(15) . . . . ?
C16 N5 C11 N2 179.01(10) . . . . ?
C16 N5 C11 C12 -0.43(15) . . . . ?
C9 C7 C6 N2 -28.37(10) . . . . ?
C9 C7 C6 C5 93.44(9) . . . . ?
C9 C7 C3 N1 48.95(11) . . . . ?
C9 C7 C3 C4 -76.17(10) . . . . ?
C14 N3 C15 N4 -179.99(10) . . . . ?
C14 N3 C15 C12 0.12(12) . . . . ?
C10 N2 C11 N5 -178.11(10) . . . . ?
C10 N2 C11 C12 1.30(17) . . . . ?
C10 N2 C6 C7 11.64(12) . . . . ?
C10 N2 C6 C5 -104.82(10) . . . . ?
C8 C7 C6 N2 92.77(10) . . . . ?
C8 C7 C6 C5 -145.42(10) . . . . ?
C8 C7 C3 N1 -78.25(11) . . . . ?
C8 C7 C3 C4 156.62(9) . . . . ?
C8 C7 C9 C10 -86.71(10) . . . . ?
C2 S1 N1 C3 63.56(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 N4 0.864(17) 2.081(17) 2.9324(12) 168.1(15) 5_667 yes
N1 H1 O2 0.817(18) 2.170(19) 2.9605(12) 163.0(17) 7_666 yes
C1 H1C O1 0.99(2) 2.58(2) 3.4669(18) 149.4(14) 5_766 yes


#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_21JLR003_KM-045-F1
_database_code_depnum_ccdc_archive 'CCDC 2482161'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C23 H27 N5'
_chemical_formula_sum            'C23 H27 N5'
_chemical_formula_weight         373.49

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.89197(15)
_cell_length_b                   8.29233(13)
_cell_length_c                   15.5755(2)
_cell_angle_alpha                88.6463(13)
_cell_angle_beta                 79.6474(14)
_cell_angle_gamma                84.9350(14)
_cell_volume                     998.76(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    17517
_cell_measurement_theta_min      2.874
_cell_measurement_theta_max      79.137

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.133
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.0985
-1 1 1 0.0925
1 -1 -1 0.1007
-1 0 1 0.0661
1 0 -1 0.0805
0 0 -1 0.0667
0 0 1 0.0667
1 0 1 0.0922
-1 0 -1 0.084
-1 -1 1 0.0795
1 1 -1 0.0928
0 1 -1 0.0934
0 -1 1 0.1144
1 1 0 0.0885
-1 -1 0 0.0885
1 -1 1 0.0992
-1 1 -1 0.0909
0 -1 0 0.1045
0 1 0 0.0893
1 0 0 0.072
-1 1 0 0.0966
-1 0 0 0.0802
4 2 7 0.0861
3 1 -7 0.0731
-2 -1 -10 0.081

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 -0.999 -1.0036 -0.1988 0.0522 -0.0484
-1.0001 0.998 1.0046 0.2665 -0.0931 -0.1344
1.0001 -0.998 -1.0046 -0.2665 0.0931 0.1344
-0.9994 -0.0017 1.0018 0.1386 0.0299 -0.1919
0.9994 0.0017 -1.0018 -0.1386 -0.0299 0.1919
-0.0005 0.0007 -1.0008 -0.071 -0.0708 0.009
0.0005 -0.0007 1.0008 0.071 0.0708 -0.009
1.0004 0.0003 0.9998 0.0033 0.1116 0.1738
-1.0004 -0.0003 -0.9998 -0.0033 -0.1116 -0.1738
-0.9987 -1.0015 0.999 0.0107 0.1529 -0.2493
0.9987 1.0015 -0.999 -0.0107 -0.1529 0.2493
-0.0012 1.0005 -0.998 0.0569 -0.1937 0.0665
0.0012 -1.0005 0.998 -0.0569 0.1937 -0.0665
0.9992 1.0007 0.0018 0.0603 -0.0821 0.2402
-0.9992 -1.0007 -0.0018 -0.0603 0.0821 -0.2402
1.0011 -0.9995 0.997 -0.1246 0.2346 0.1164
-1.0011 0.9995 -0.997 0.1246 -0.2346 -0.1164
0.0007 -0.9997 -0.0028 -0.1279 0.123 -0.0574
-0.0007 0.9997 0.0028 0.1279 -0.123 0.0574
0.9999 0.001 -0.001 -0.0676 0.0408 0.1828
-1.0006 0.9987 0.0038 0.1955 -0.1638 -0.1254
-0.9999 -0.001 0.001 0.0676 -0.0408 -0.1828
4.1718 1.9273 6.5172 0.4266 0.3939 0.8142
3.0072 1.2414 -6.7703 -0.5259 -0.5074 0.6826
-2.345 -1.1588 -9.5136 -0.665 -0.6251 -0.4088


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.77768
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.926
_oxdiff_exptl_absorpt_empirical_details 
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.105
_oxdiff_exptl_absorpt_empirical_full_min 0.616

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0676827
_diffrn_orient_matrix_ub_12      0.1276849
_diffrn_orient_matrix_ub_13      0.0710268
_diffrn_orient_matrix_ub_21      0.0410416
_diffrn_orient_matrix_ub_22      -0.1231655
_diffrn_orient_matrix_ub_23      0.0705884
_diffrn_orient_matrix_ub_31      0.1827606
_diffrn_orient_matrix_ub_32      0.0575756
_diffrn_orient_matrix_ub_33      -0.0090923
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_number            29835
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.884
_diffrn_reflns_theta_max         70.855
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             3846
_reflns_number_gt                3460
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
        List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00 -25.00   0.50    0.35    --  -21.00 149.00-111.00  114
  2  ω    -67.00 -11.00   0.50    0.35    --  -21.00 123.00  84.00  112
  3  ω     33.00  94.00   0.50    0.35    --   47.66-123.00   4.00  122
  4  ω     42.00 110.00   0.50    1.90    --  113.25-123.00   4.00  136
  5  ω     96.00 177.00   0.50    1.90    --  113.25 123.00  84.00  162
  6  ω    -34.00  51.00   0.50    0.35    --  -21.00  45.00-180.00  170
  7  ω    -93.00  -6.00   0.50    0.35    --  -21.00 -57.00-120.00  174
  8  ω     -3.00  34.00   0.50    0.35    --   28.00  94.00-179.58   74
  9  ω     -1.00  27.00   0.50    0.35    --   32.00  98.00  -8.20   56
 10  ω     16.00  43.00   0.50    0.35    --   44.00  88.00-178.87   54
 11  ω    -24.00  70.00   0.50    0.35    --   47.66 -77.00-180.00  188
 12  ω    -27.00  23.00   0.50    0.35    --   47.66 -19.00  90.00  100
 13  ω     25.00 120.00   0.50    0.35    --   47.66  77.00 120.00  190
 14  ω     34.00  95.00   0.50    0.35    --   47.66-125.00 150.00  122
 15  ω     27.00 121.00   0.50    0.35    --   48.00  74.00 -29.08  188
 16  ω     30.00 125.00   0.50    0.35    --   52.00  75.00 -84.71  190
 17  ω     29.00 125.00   0.50    0.35    --   52.00  77.00  67.83  192
 18  ω     29.00 125.00   0.50    0.35    --   52.00  77.00-139.71  192
 19  ω     34.00 129.00   0.50    0.35    --   56.00  75.00   9.30  190
 20  ω     39.00 132.00   0.50    0.35    --   60.00  74.00  58.82  186
 21  ω     38.00 132.00   0.50    0.35    --   60.00  76.00 -28.14  188
 22  ω     39.00 132.00   0.50    0.35    --   60.00  73.00 151.80  186
 23  ω     42.00 137.00   0.50    0.35    --   64.00  76.00 161.87  190
 24  ω     45.00 137.00   0.50    0.35    --   64.00  68.00-115.84  184
 25  ω     41.00 137.00   0.50    0.35    --   64.00  77.00  14.18  192
 26  ω     42.00 137.00   0.50    0.35    --   64.00  75.00 -84.30  190
 27  ω     45.00 140.00   0.50    0.35    --   68.00  77.00 105.41  190
 28  ω     48.00 140.00   0.50    0.35    --   68.00  71.00-179.80  184
 29  ω     47.00 140.00   0.50    0.35    --   68.00  74.00  88.81  186
 30  ω     46.00 140.00   0.50    0.35    --   68.00  75.00-167.60  188
 31  ω     47.00 140.00   0.50    0.35    --   68.00  73.00  28.07  186
 32  ω     46.00 140.00   0.50    0.35    --   68.00  76.00 -97.93  188
 33  ω     62.00 134.00   0.50    0.35    --   76.00  58.00 155.15  144
 34  ω    139.00 173.00   0.50    1.90    --  113.25  77.00-180.00   68
 35  ω     92.00 119.00   0.50    1.90    --  113.25  77.00-180.00   54
 36  ω     67.00 106.00   0.50    1.90    --  113.25 -94.00 150.00   78
 37  ω     98.00 148.00   0.50    1.90    --  113.25  61.00 -90.00  100
 38  ω    130.00 177.00   0.50    1.90    --  113.25  77.00 150.00   94
 39  ω     42.00  67.00   0.50    1.90    --  113.25 -61.00  60.00   50
 40  ω     99.00 150.00   0.50    1.90    --  113.25  61.00-150.00  102
 41  ω     91.00 118.00   0.50    1.90    --  113.25  77.00 120.00   54
 42  ω     93.00 120.00   0.50    1.90    --  113.25  77.00 150.00   54
 43  ω     79.00 107.00   0.50    1.90    --  113.25-125.00-180.00   56
 44  ω     92.00 117.00   0.50    1.90    --  113.25  77.00-150.00   50
 45  ω     42.00  78.00   0.50    1.90    --  113.25-125.00-180.00   72
 46  ω    142.00 174.00   0.50    1.90    --  113.25  61.00-120.00   64
 47  ω     81.00 106.00   0.50    1.90    --  113.25 -94.00-180.00   50
 48  ω    135.00 172.00   0.50    1.90    --  113.25  77.00-150.00   74
 49  ω     91.00 124.00   0.50    1.90    --  113.25  77.00   0.00   66
 50  ω    134.00 170.00   0.50    1.90    --  113.25  77.00   0.00   72
 51  ω     97.00 158.00   0.50    1.90    --  113.25  61.00 -60.00  122
 52  ω    122.00 177.00   0.50    1.90    --  113.25  77.00 120.00  110
 53  ω     91.00 136.00   0.50    1.90    --  113.25  77.00 -60.00   90
 54  ω    146.00 174.00   0.50    1.90    --  113.25  77.00 -60.00   56
 55  ω     93.00 151.00   0.50    1.90    --  113.25  77.00 -90.00  116
 56  ω     97.00 161.00   0.50    1.90    --  113.25  61.00 -30.00  128
 57  ω     91.00 136.00   0.50    1.90    --  113.25  77.00  60.00   90
 58  ω    115.00 169.00   0.50    1.90    --  113.25  45.00 120.00  108
 59  ω     63.00 106.00   0.50    1.90    --  113.25 -94.00-120.00   86
 60  ω     98.00 136.00   0.50    1.90    --  113.25  61.00-120.00   76
 61  ω    152.00 177.00   0.50    1.90    --  113.25  61.00  90.00   50
 62  ω     91.00 138.00   0.50    1.90    --  113.25  77.00-120.00   94
 63  ω     97.00 133.00   0.50    1.90    --  113.25  61.00  90.00   72
 64  ω     71.00 104.00   0.50    1.90    --  113.25 -94.00  30.00   66
 65  ω    130.00 175.00   0.50    1.90    --  113.25  77.00 -30.00   90
 66  ω     42.00  67.00   0.50    1.90    --  113.25 -61.00 120.00   50
 67  ω     91.00 122.00   0.50    1.90    --  113.25  77.00 -30.00   62
 68  ω     42.00  68.00   0.50    1.90    --  113.25 -61.00  90.00   52
 69  ω     42.00  75.00   0.50    1.90    --  113.25 -94.00-180.00   66
 70  ω     45.00  99.00   0.50    1.90    --  113.25 -77.00-180.00  108
 71  ω     45.00  99.00   0.50    1.90    --  113.25 -77.00  60.00  108
 72  ω     98.00 170.00   0.50    1.90    --  113.25  61.00  60.00  144
 73  ω     84.00 111.00   0.50    1.90    --  113.25-125.00  30.00   54
 74  ω     50.00  77.00   0.50    1.90    --  113.25-125.00  30.00   54
 75  ω    132.00 159.00   0.50    1.90    --  113.25  61.00   0.00   54
 76  ω     42.00  67.00   0.50    1.90    --  113.25 -61.00 -60.00   50
 77  ω     43.00  81.00   0.50    1.90    --  113.25-125.00 -30.00   76
 78  ω     97.00 127.00   0.50    1.90    --  113.25  61.00 150.00   60
 79  ω    147.00 174.00   0.50    1.90    --  113.25  61.00  30.00   54
 80  ω    101.00 154.00   0.50    1.90    --  113.25 125.00   0.00  106
 81  ω     44.00  97.00   0.50    1.90    --  113.25 -77.00  30.00  106
 82  ω     91.00 133.00   0.50    1.90    --  113.25  77.00  90.00   84
 83  ω     91.00 124.00   0.50    1.90    --  113.25  77.00  30.00   66
 84  ω     97.00 125.00   0.50    1.90    --  113.25  61.00  30.00   56
 85  ω     74.00 101.00   0.50    1.90    --  113.25 -77.00-120.00   54
 86  ω     47.00  74.00   0.50    1.90    --  113.25 -77.00   0.00   54
 87  ω     42.00  67.00   0.50    1.90    --  113.25 -61.00-120.00   50
 88  ω    100.00 127.00   0.50    1.90    --  113.25  61.00   0.00   54
 89  ω    100.00 157.00   0.50    1.90    --  113.25  61.00-180.00  114
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0977P)²+0.5048P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3846
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1707
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.049
_olex2_refinement_description    
;
        1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
        2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
        2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C12(H12A,H12B), C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B),
 C16(H16A,H16B), C13(H13A,H13B), C15(H15A,H15B)
        2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C5(H5), C23(H23), C19(H19), C22(H22), C20(H20),
 C21(H21)
;

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
N2 N 0.67678(19) 0.11897(19) 0.03455(11) 0.0388(4) Uani 1 1 d . . . . .
N3 N 0.82751(19) 0.3319(2) 0.07942(11) 0.0409(4) Uani 1 1 d . . . . .
N1 N 0.36866(19) 0.17696(19) 0.05930(10) 0.0376(4) Uani 1 1 d . . . . .
H1 H 0.342154 0.087622 0.037351 0.045 Uiso 1 1 calc R U . . .
N4 N 0.6978(2) 0.5681(2) 0.14728(11) 0.0407(4) Uani 1 1 d . . . . .
N5 N 0.3615(2) 0.7783(2) 0.39357(11) 0.0435(4) Uani 1 1 d . . . . .
C4 C 0.5301(2) 0.2129(2) 0.06594(11) 0.0348(4) Uani 1 1 d . . . . .
C6 C 0.6799(2) 0.4235(2) 0.11172(12) 0.0359(4) Uani 1 1 d . . . . .
C3 C 0.5195(2) 0.3647(2) 0.10526(11) 0.0348(4) Uani 1 1 d . . . . .
C1 C 0.2531(2) 0.3040(2) 0.09273(13) 0.0399(4) Uani 1 1 d . . . . .
H1A H 0.131563 0.309224 0.095436 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3392(2) 0.4203(2) 0.12110(13) 0.0398(4) Uani 1 1 d . . . . .
H2 H 0.289564 0.52024 0.146772 0.048 Uiso 1 1 calc R U . . .
C18 C 0.1273(3) 0.8158(3) 0.52079(14) 0.0480(5) Uani 1 1 d . . . . .
C10 C 0.6134(2) 0.7290(2) 0.28484(13) 0.0413(4) Uani 1 1 d . . . . .
C11 C 0.5556(2) 0.6597(2) 0.20479(12) 0.0397(4) Uani 1 1 d . . . . .
H11 H 0.465481 0.583711 0.226583 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8161(2) 0.1897(2) 0.04410(13) 0.0414(4) Uani 1 1 d . . . . .
H5 H 0.923338 0.130372 0.022647 0.05 Uiso 1 1 calc R U . . .
C14 C 0.4633(3) 0.8558(2) 0.31958(13) 0.0433(5) Uani 1 1 d . . . . .
H14 H 0.509251 0.954831 0.338866 0.052 Uiso 1 1 calc R U . . .
C17 C 0.2458(3) 0.8957(3) 0.44979(15) 0.0494(5) Uani 1 1 d . . . . .
H17A H 0.175881 0.963953 0.413794 0.059 Uiso 1 1 calc R U . . .
H17B H 0.315827 0.967259 0.476297 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4670(3) 0.8074(3) 0.16513(13) 0.0458(5) Uani 1 1 d . . . . .
H12A H 0.390316 0.774223 0.126139 0.055 Uiso 1 1 calc R U . . .
H12B H 0.553281 0.875371 0.131581 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7843(3) 0.8071(3) 0.25973(14) 0.0464(5) Uani 1 1 d . . . . .
H9A H 0.765022 0.908179 0.226462 0.056 Uiso 1 1 calc R U . . .
H9B H 0.825255 0.835753 0.313421 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8595(2) 0.6463(3) 0.12454(14) 0.0469(5) Uani 1 1 d . . . . .
H7A H 0.840699 0.743709 0.088343 0.056 Uiso 1 1 calc R U . . .
H7B H 0.948494 0.570955 0.089627 0.056 Uiso 1 1 calc R U . . .
C23 C -0.0047(3) 0.7309(3) 0.50143(16) 0.0545(5) Uani 1 1 d . . . . .
H23 H -0.017061 0.719986 0.442337 0.065 Uiso 1 1 calc R U . . .
C8 C 0.9230(3) 0.6941(3) 0.20470(16) 0.0513(5) Uani 1 1 d . . . . .
H8A H 1.030264 0.749586 0.187679 0.062 Uiso 1 1 calc R U . . .
H8B H 0.949714 0.596351 0.23919 0.062 Uiso 1 1 calc R U . . .
C16 C 0.6145(3) 0.6051(3) 0.36151(14) 0.0500(5) Uani 1 1 d . . . . .
H16A H 0.5726 0.501578 0.347373 0.06 Uiso 1 1 calc R U . . .
H16B H 0.731905 0.583745 0.37553 0.06 Uiso 1 1 calc R U . . .
C13 C 0.3623(3) 0.8985(3) 0.24459(14) 0.0520(5) Uani 1 1 d . . . . .
H13A H 0.244084 0.862639 0.258975 0.062 Uiso 1 1 calc R U . . .
H13B H 0.354181 1.016667 0.23334 0.062 Uiso 1 1 calc R U . . .
C15 C 0.4909(3) 0.6898(3) 0.43681(15) 0.0527(5) Uani 1 1 d . . . . .
H15A H 0.437736 0.610333 0.479495 0.063 Uiso 1 1 calc R U . . .
H15B H 0.551095 0.764536 0.467169 0.063 Uiso 1 1 calc R U . . .
C19 C 0.1427(3) 0.8268(3) 0.60856(16) 0.0592(6) Uani 1 1 d . . . . .
H19 H 0.233895 0.88172 0.623519 0.071 Uiso 1 1 calc R U . . .
C22 C -0.1186(3) 0.6618(3) 0.56709(18) 0.0637(6) Uani 1 1 d . . . . .
H22 H -0.207773 0.603179 0.552867 0.076 Uiso 1 1 calc R U . . .
C20 C 0.0278(4) 0.7591(3) 0.67345(17) 0.0699(7) Uani 1 1 d . . . . .
H20 H 0.039215 0.768992 0.732744 0.084 Uiso 1 1 calc R U . . .
C21 C -0.1028(4) 0.6779(3) 0.65307(18) 0.0683(7) Uani 1 1 d . . . . .
H21 H -0.182598 0.632451 0.698166 0.082 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C4 1.357(2) . ?
N2 C5 1.324(2) . ?
N3 C6 1.356(2) . ?
N3 C5 1.329(3) . ?
N1 H1 0.88 . ?
N1 C4 1.356(2) . ?
N1 C1 1.378(2) . ?
N4 C6 1.361(2) . ?
N4 C11 1.469(2) . ?
N4 C7 1.466(2) . ?
N5 C14 1.452(3) . ?
N5 C17 1.464(2) . ?
N5 C15 1.458(3) . ?
C4 C3 1.402(3) . ?
C6 C3 1.417(2) . ?
C3 C2 1.436(2) . ?
C1 H1A 0.95 . ?
C1 C2 1.353(3) . ?
C2 H2 0.95 . ?
C18 C17 1.497(3) . ?
C18 C23 1.387(3) . ?
C18 C19 1.400(3) . ?
C10 C11 1.542(3) . ?
C10 C14 1.542(3) . ?
C10 C9 1.531(3) . ?
C10 C16 1.558(3) . ?
C11 H11 1 . ?
C11 C12 1.530(3) . ?
C5 H5 0.95 . ?
C14 H14 1 . ?
C14 C13 1.546(3) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C12 C13 1.533(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C9 C8 1.526(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C7 C8 1.500(3) . ?
C23 H23 0.95 . ?
C23 C22 1.384(4) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C16 C15 1.525(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C19 H19 0.95 . ?
C19 C20 1.376(4) . ?
C22 H22 0.95 . ?
C22 C21 1.378(4) . ?
C20 H20 0.95 . ?
C20 C21 1.366(4) . ?
C21 H21 0.95 . ?

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
C5 N2 C4 111.32(15) . . ?
C5 N3 C6 118.84(16) . . ?
C4 N1 H1 125.8 . . ?
C4 N1 C1 108.44(15) . . ?
C1 N1 H1 125.8 . . ?
C6 N4 C11 122.87(15) . . ?
C6 N4 C7 120.77(15) . . ?
C7 N4 C11 116.22(15) . . ?
C14 N5 C17 112.02(16) . . ?
C14 N5 C15 103.82(16) . . ?
C15 N5 C17 113.74(17) . . ?
N2 C4 C3 126.53(16) . . ?
N1 C4 N2 124.42(16) . . ?
N1 C4 C3 108.95(15) . . ?
N3 C6 N4 116.82(16) . . ?
N3 C6 C3 118.51(16) . . ?
N4 C6 C3 124.66(16) . . ?
C4 C3 C6 115.50(16) . . ?
C4 C3 C2 105.63(15) . . ?
C6 C3 C2 138.62(17) . . ?
N1 C1 H1A 125.2 . . ?
C2 C1 N1 109.63(16) . . ?
C2 C1 H1A 125.2 . . ?
C3 C2 H2 126.3 . . ?
C1 C2 C3 107.34(16) . . ?
C1 C2 H2 126.3 . . ?
C23 C18 C17 120.6(2) . . ?
C23 C18 C19 117.8(2) . . ?
C19 C18 C17 121.6(2) . . ?
C11 C10 C16 113.21(17) . . ?
C14 C10 C11 103.10(15) . . ?
C14 C10 C16 103.79(16) . . ?
C9 C10 C11 111.84(16) . . ?
C9 C10 C14 111.34(16) . . ?
C9 C10 C16 112.83(18) . . ?
N4 C11 C10 112.65(15) . . ?
N4 C11 H11 107.8 . . ?
N4 C11 C12 117.00(16) . . ?
C10 C11 H11 107.8 . . ?
C12 C11 C10 103.48(16) . . ?
C12 C11 H11 107.8 . . ?
N2 C5 N3 129.28(17) . . ?
N2 C5 H5 115.4 . . ?
N3 C5 H5 115.4 . . ?
N5 C14 C10 105.26(16) . . ?
N5 C14 H14 110.2 . . ?
N5 C14 C13 113.15(17) . . ?
C10 C14 H14 110.2 . . ?
C10 C14 C13 107.57(16) . . ?
C13 C14 H14 110.2 . . ?
N5 C17 C18 112.36(17) . . ?
N5 C17 H17A 109.1 . . ?
N5 C17 H17B 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C11 C12 H12A 111 . . ?
C11 C12 H12B 111 . . ?
C11 C12 C13 103.89(16) . . ?
H12A C12 H12B 109 . . ?
C13 C12 H12A 111 . . ?
C13 C12 H12B 111 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C8 C9 C10 111.80(16) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
N4 C7 H7A 109.4 . . ?
N4 C7 H7B 109.4 . . ?
N4 C7 C8 111.29(17) . . ?
H7A C7 H7B 108 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 C9 109.47(17) . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C10 C16 H16A 111.1 . . ?
C10 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?
C15 C16 C10 103.22(17) . . ?
C15 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
C12 C13 C14 105.00(16) . . ?
C12 C13 H13A 110.7 . . ?
C12 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
N5 C15 C16 103.17(17) . . ?
N5 C15 H15A 111.1 . . ?
N5 C15 H15B 111.1 . . ?
C16 C15 H15A 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.5 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C22 C21 H21 120 . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C4 C3 C6 0.3(3) . . . . ?
N2 C4 C3 C2 175.70(18) . . . . ?
N3 C6 C3 C4 0.7(3) . . . . ?
N3 C6 C3 C2 -172.6(2) . . . . ?
N1 C4 C3 C6 -176.21(16) . . . . ?
N1 C4 C3 C2 -0.8(2) . . . . ?
N1 C1 C2 C3 -0.2(2) . . . . ?
N4 C6 C3 C4 179.72(17) . . . . ?
N4 C6 C3 C2 6.4(4) . . . . ?
N4 C11 C12 C13 -165.80(17) . . . . ?
N4 C7 C8 C9 -57.7(2) . . . . ?
N5 C14 C13 C12 -121.16(18) . . . . ?
C4 N2 C5 N3 0.8(3) . . . . ?
C4 N1 C1 C2 -0.4(2) . . . . ?
C4 C3 C2 C1 0.6(2) . . . . ?
C6 N3 C5 N2 0.2(3) . . . . ?
C6 N4 C11 C10 136.53(19) . . . . ?
C6 N4 C11 C12 -103.7(2) . . . . ?
C6 N4 C7 C8 -129.4(2) . . . . ?
C6 C3 C2 C1 174.3(2) . . . . ?
C1 N1 C4 N2 -175.87(17) . . . . ?
C1 N1 C4 C3 0.7(2) . . . . ?
C18 C23 C22 C21 0.5(4) . . . . ?
C18 C19 C20 C21 0.9(4) . . . . ?
C10 C11 C12 C13 -41.3(2) . . . . ?
C10 C14 C13 C12 -5.3(2) . . . . ?
C10 C9 C8 C7 57.2(2) . . . . ?
C10 C16 C15 N5 34.4(2) . . . . ?
C11 N4 C6 N3 -163.23(17) . . . . ?
C11 N4 C6 C3 17.7(3) . . . . ?
C11 N4 C7 C8 54.7(2) . . . . ?
C11 C10 C14 N5 101.29(17) . . . . ?
C11 C10 C14 C13 -19.6(2) . . . . ?
C11 C10 C9 C8 -50.9(2) . . . . ?
C11 C10 C16 C15 -121.59(18) . . . . ?
C11 C12 C13 C14 28.5(2) . . . . ?
C5 N2 C4 N1 175.03(18) . . . . ?
C5 N2 C4 C3 -1.0(3) . . . . ?
C5 N3 C6 N4 179.98(18) . . . . ?
C5 N3 C6 C3 -0.9(3) . . . . ?
C14 N5 C17 C18 173.96(18) . . . . ?
C14 N5 C15 C16 -46.6(2) . . . . ?
C14 C10 C11 N4 164.59(16) . . . . ?
C14 C10 C11 C12 37.29(18) . . . . ?
C14 C10 C9 C8 -165.63(18) . . . . ?
C14 C10 C16 C15 -10.5(2) . . . . ?
C17 N5 C14 C10 162.75(17) . . . . ?
C17 N5 C14 C13 -80.1(2) . . . . ?
C17 N5 C15 C16 -168.59(18) . . . . ?
C17 C18 C23 C22 -177.6(2) . . . . ?
C17 C18 C19 C20 176.9(2) . . . . ?
C9 C10 C11 N4 44.9(2) . . . . ?
C9 C10 C11 C12 -82.43(18) . . . . ?
C9 C10 C14 N5 -138.65(17) . . . . ?
C9 C10 C14 C13 100.4(2) . . . . ?
C9 C10 C16 C15 110.12(19) . . . . ?
C7 N4 C6 N3 21.2(3) . . . . ?
C7 N4 C6 C3 -157.88(19) . . . . ?
C7 N4 C11 C10 -47.7(2) . . . . ?
C7 N4 C11 C12 72.1(2) . . . . ?
C23 C18 C17 N5 -69.7(3) . . . . ?
C23 C18 C19 C20 -1.7(3) . . . . ?
C23 C22 C21 C20 -1.4(4) . . . . ?
C16 C10 C11 N4 -83.9(2) . . . . ?
C16 C10 C11 C12 148.76(16) . . . . ?
C16 C10 C14 N5 -17.0(2) . . . . ?
C16 C10 C14 C13 -137.91(18) . . . . ?
C16 C10 C9 C8 78.1(2) . . . . ?
C15 N5 C14 C10 39.61(19) . . . . ?
C15 N5 C14 C13 156.80(18) . . . . ?
C15 N5 C17 C18 -68.7(2) . . . . ?
C19 C18 C17 N5 111.7(2) . . . . ?
C19 C18 C23 C22 1.0(3) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A N3 0.95 2.45 3.390(2) 171.6 1_455 yes


#----------------------------------------------------------------------------#
#                       SHELX RES FILE                                       #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                       SHELX HKL FILE                                       #
#----------------------------------------------------------------------------#


# END of CIF
####################################################################### 
# 
# 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_22JLR020_KM-157-01
_database_code_depnum_ccdc_archive 'CCDC 2482165'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;

_audit_creation_date             2022-12-22T19:49:56-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C14 H20 N5, C2 H3 O2, 3(H2 O)'
_chemical_formula_sum            'C16 H29 N5 O5'
_chemical_formula_weight         371.44

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3008(3)
_cell_length_b                   10.3514(3)
_cell_length_c                   10.8884(3)
_cell_angle_alpha                61.817(3)
_cell_angle_beta                 77.117(3)
_cell_angle_gamma                83.188(3)
_cell_volume                     997.48(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    15323
_cell_measurement_theta_min      4.414
_cell_measurement_theta_max      79.371

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.028
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 1 0.034
0 -1 0 0.052
1 1 0 0.0431
-1 0 0 0.0204
1 0 0 0.0076
-1 1 0 0.0395
1 -1 0 0.0421
-1 -1 -1 0.0372
-1 0 -1 0.0158
0 1 1 0.0487
0 0 -1 0.0158
0 0 1 0.0456
0 -1 1 0.0358
0 1 -1 0.0384
-1 0 1 0.0314
1 -1 -1 0.0339
1 0 -1 0.0094


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.77
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
        Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.979

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1461767
_diffrn_orient_matrix_ub_12      0.0169422
_diffrn_orient_matrix_ub_13      -0.0782443
_diffrn_orient_matrix_ub_21      0.0440767
_diffrn_orient_matrix_ub_22      -0.0072217
_diffrn_orient_matrix_ub_23      0.1293608
_diffrn_orient_matrix_ub_31      0.0152492
_diffrn_orient_matrix_ub_32      -0.1678578
_diffrn_orient_matrix_ub_33      0.0623077
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_number            22904
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.404
_diffrn_reflns_theta_max         67.708
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             3607
_reflns_number_gt                3312
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.1766P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3607
_refine_ls_number_parameters     361
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.029

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O -0.14316(8) 0.52716(9) 0.89866(9) 0.03703(19) Uani 1 1 d . . . . .
O1 O -0.13506(8) 0.26810(9) 0.89547(10) 0.0424(2) Uani 1 1 d . . . . .
O2 O -0.21233(8) 0.07104(9) 0.90935(9) 0.0415(2) Uani 1 1 d . . . . .
O4 O -0.40481(9) 0.96255(11) 0.83942(10) 0.0473(2) Uani 1 1 d . . . . .
N5 N 0.11151(9) 0.15979(10) 0.87650(10) 0.0313(2) Uani 1 1 d . . . . .
N4 N 0.50352(9) 0.16545(11) 0.58185(10) 0.0333(2) Uani 1 1 d . . . . .
N3 N 0.52463(9) 0.31863(10) 0.33899(10) 0.0338(2) Uani 1 1 d . . . . .
N2 N 0.73609(9) 0.40458(10) 0.18389(10) 0.0347(2) Uani 1 1 d . . . . .
N1 N 0.92344(10) 0.31079(11) 0.30172(11) 0.0376(2) Uani 1 1 d . . . . .
O5 O -0.3014(4) 0.7561(2) 0.7440(4) 0.0520(8) Uani 0.843(14) 1 d . . P A 1
C6 C 0.58132(10) 0.24164(11) 0.45476(11) 0.0304(2) Uani 1 1 d . . . . .
C3 C 0.72205(10) 0.24168(12) 0.43806(11) 0.0313(2) Uani 1 1 d . . . . .
C4 C 0.79121(10) 0.32496(11) 0.30031(11) 0.0311(2) Uani 1 1 d . . . . .
C10 C 0.13910(10) 0.16468(12) 0.73237(11) 0.0314(2) Uani 1 1 d . . . . .
C7 C 0.36094(10) 0.14569(12) 0.60438(11) 0.0320(2) Uani 1 1 d . . . . .
C15 C -0.22492(11) 0.20173(12) 0.88741(11) 0.0344(2) Uani 1 1 d . . . . .
C5 C 0.60464(11) 0.39368(12) 0.21345(12) 0.0350(2) Uani 1 1 d . . . . .
C8 C 0.31586(11) -0.00648(12) 0.72099(12) 0.0334(2) Uani 1 1 d . . . . .
C11 C 0.26998(10) 0.25192(12) 0.65082(12) 0.0321(2) Uani 1 1 d . . . . .
C14 C 0.19264(11) 0.27680(13) 0.86478(13) 0.0366(3) Uani 1 1 d . . . . .
C9 C 0.16479(11) 0.01110(13) 0.74232(13) 0.0353(2) Uani 1 1 d . . . . .
C13 C 0.31950(11) 0.27183(13) 0.76445(13) 0.0355(3) Uani 1 1 d . . . . .
C2 C 0.81998(12) 0.17381(14) 0.52567(13) 0.0399(3) Uani 1 1 d . . . . .
C1 C 0.94031(12) 0.21873(15) 0.43858(13) 0.0433(3) Uani 1 1 d . . . . .
C12 C 0.24740(13) 0.39955(14) 0.52677(14) 0.0445(3) Uani 1 1 d . . . . .
C16 C -0.35315(13) 0.28219(17) 0.85096(19) 0.0532(4) Uani 1 1 d . . . . .
H10 H 0.0639(13) 0.2146(14) 0.6884(13) 0.032(3) Uiso 1 1 d . . . . .
H9A H 0.1203(14) -0.0640(16) 0.8301(15) 0.040(3) Uiso 1 1 d . . . . .
H13A H 0.3713(12) 0.1854(14) 0.8182(13) 0.030(3) Uiso 1 1 d . . . . .
H5 H 0.5581(13) 0.4465(14) 0.1339(14) 0.034(3) Uiso 1 1 d . . . . .
H8A H 0.3478(12) -0.0283(14) 0.8049(14) 0.033(3) Uiso 1 1 d . . . . .
H7 H 0.3412(12) 0.1615(14) 0.5131(14) 0.034(3) Uiso 1 1 d . . . . .
H4 H 0.5428(14) 0.1130(16) 0.6525(16) 0.042(4) Uiso 1 1 d . . . . .
H8B H 0.3478(13) -0.0814(16) 0.6940(14) 0.039(3) Uiso 1 1 d . . . . .
H14A H 0.1432(14) 0.3720(16) 0.8208(15) 0.042(3) Uiso 1 1 d . . . . .
H9B H 0.1334(13) 0.0090(14) 0.6652(14) 0.036(3) Uiso 1 1 d . . . . .
H2 H 0.8055(14) 0.1068(17) 0.6263(17) 0.048(4) Uiso 1 1 d . . . . .
H5A H 0.1389(14) 0.0685(16) 0.9468(15) 0.041(3) Uiso 1 1 d . . . . .
H14B H 0.2033(13) 0.2533(15) 0.9610(15) 0.040(3) Uiso 1 1 d . . . . .
H12A H 0.1874(16) 0.4627(17) 0.5627(16) 0.052(4) Uiso 1 1 d . . . . .
H1 H 0.9847(16) 0.3552(17) 0.2313(17) 0.046(4) Uiso 1 1 d . . . . .
H13B H 0.3693(14) 0.3606(16) 0.7214(15) 0.041(3) Uiso 1 1 d . . . . .
H12B H 0.3349(16) 0.4486(17) 0.4755(17) 0.053(4) Uiso 1 1 d . . . . .
H12C H 0.2067(15) 0.3849(17) 0.4591(17) 0.052(4) Uiso 1 1 d . . . . .
H5B H 0.0188(16) 0.1813(17) 0.9009(16) 0.049(4) Uiso 1 1 d . . . . .
H1A H 1.0292(15) 0.1899(16) 0.4586(16) 0.049(4) Uiso 1 1 d . . . . .
H16A H -0.426(2) 0.233(2) 0.924(2) 0.084(6) Uiso 1 1 d . . . . .
H16B H -0.351(2) 0.378(2) 0.833(2) 0.080(6) Uiso 1 1 d . . . . .
H16C H -0.368(2) 0.283(3) 0.762(3) 0.113(8) Uiso 1 1 d . . . . .
H3A H -0.1745(17) 0.4960(19) 0.988(2) 0.060(5) Uiso 1 1 d . . . . .
H3B H -0.1428(16) 0.450(2) 0.8887(18) 0.058(5) Uiso 1 1 d . . . . .
H4A H -0.345(2) 0.990(2) 0.869(2) 0.075(6) Uiso 1 1 d . . . . .
H4B H -0.3637(19) 0.886(2) 0.817(2) 0.072(5) Uiso 1 1 d . . . . .
H5C H -0.259(2) 0.678(2) 0.798(2) 0.075(6) Uiso 1 1 d . . . . .
H5D H -0.364(2) 0.727(2) 0.717(2) 0.078(6) Uiso 1 1 d . . . . .
O5A O -0.351(2) 0.722(2) 0.811(3) 0.065(4) Uani 0.157(14) 1 d . U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 H3A 0.86(2) . ?
O3 H3B 0.856(19) . ?
O1 C15 1.2572(14) . ?
O2 C15 1.2534(14) . ?
O4 H4A 0.88(2) . ?
O4 H4B 0.96(2) . ?
N5 C10 1.5085(14) . ?
N5 C14 1.4927(14) . ?
N5 H5A 0.953(15) . ?
N5 H5B 0.962(16) . ?
N4 C6 1.3430(14) . ?
N4 C7 1.4568(14) . ?
N4 H4 0.862(16) . ?
N3 C6 1.3543(14) . ?
N3 C5 1.3408(15) . ?
N2 C4 1.3533(15) . ?
N2 C5 1.3257(15) . ?
N1 C4 1.3553(14) . ?
N1 C1 1.3762(17) . ?
N1 H1 0.847(16) . ?
O5 H5C 0.88(2) . ?
O5 H5D 0.89(2) . ?
C6 C3 1.4202(15) . ?
C3 C4 1.3958(15) . ?
C3 C2 1.4314(16) . ?
C10 C11 1.5553(14) . ?
C10 C9 1.5361(16) . ?
C10 H10 0.966(13) . ?
C7 C8 1.5265(16) . ?
C7 C11 1.5532(15) . ?
C7 H7 0.992(13) . ?
C15 C16 1.5021(17) . ?
C5 H5 0.977(13) . ?
C8 C9 1.5233(15) . ?
C8 H8A 0.957(13) . ?
C8 H8B 0.953(14) . ?
C11 C13 1.5429(15) . ?
C11 C12 1.5231(16) . ?
C14 C13 1.5180(16) . ?
C14 H14A 1.002(15) . ?
C14 H14B 0.986(14) . ?
C9 H9A 0.957(15) . ?
C9 H9B 0.975(14) . ?
C13 H13A 0.979(13) . ?
C13 H13B 0.962(15) . ?
C2 C1 1.3594(18) . ?
C2 H2 0.969(16) . ?
C1 H1A 0.968(16) . ?
C12 H12A 1.001(16) . ?
C12 H12B 0.999(16) . ?
C12 H12C 1.000(16) . ?
C16 H16A 0.95(2) . ?
C16 H16B 0.92(2) . ?
C16 H16C 1.01(3) . ?
O5A H5C 1.01(2) . ?
O5A H5D 1.04(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H3A O3 H3B 102.6(16) . . ?
H4A O4 H4B 106.5(16) . . ?
C10 N5 H5A 111.7(8) . . ?
C10 N5 H5B 109.4(9) . . ?
C14 N5 C10 106.95(8) . . ?
C14 N5 H5A 107.6(8) . . ?
C14 N5 H5B 108.8(9) . . ?
H5A N5 H5B 112.2(12) . . ?
C6 N4 C7 124.66(9) . . ?
C6 N4 H4 117.2(9) . . ?
C7 N4 H4 117.3(9) . . ?
C5 N3 C6 118.06(9) . . ?
C5 N2 C4 112.20(9) . . ?
C4 N1 C1 108.29(10) . . ?
C4 N1 H1 125.7(10) . . ?
C1 N1 H1 125.9(10) . . ?
H5C O5 H5D 108.1(18) . . ?
N4 C6 N3 119.32(10) . . ?
N4 C6 C3 121.68(10) . . ?
N3 C6 C3 119.00(10) . . ?
C6 C3 C2 137.37(10) . . ?
C4 C3 C6 115.91(10) . . ?
C4 C3 C2 106.69(10) . . ?
N2 C4 N1 125.45(10) . . ?
N2 C4 C3 125.89(10) . . ?
N1 C4 C3 108.65(10) . . ?
N5 C10 C11 105.89(8) . . ?
N5 C10 C9 112.00(9) . . ?
N5 C10 H10 106.6(7) . . ?
C11 C10 H10 112.1(7) . . ?
C9 C10 C11 107.23(8) . . ?
C9 C10 H10 112.9(7) . . ?
N4 C7 C8 112.61(9) . . ?
N4 C7 C11 115.34(9) . . ?
N4 C7 H7 107.2(7) . . ?
C8 C7 C11 104.03(8) . . ?
C8 C7 H7 109.8(7) . . ?
C11 C7 H7 107.7(7) . . ?
O1 C15 C16 118.58(11) . . ?
O2 C15 O1 122.78(10) . . ?
O2 C15 C16 118.64(11) . . ?
N3 C5 H5 114.3(8) . . ?
N2 C5 N3 128.92(10) . . ?
N2 C5 H5 116.8(8) . . ?
C7 C8 H8A 109.9(8) . . ?
C7 C8 H8B 112.4(8) . . ?
C9 C8 C7 102.00(9) . . ?
C9 C8 H8A 111.7(8) . . ?
C9 C8 H8B 112.8(8) . . ?
H8A C8 H8B 108.0(11) . . ?
C7 C11 C10 103.20(8) . . ?
C13 C11 C10 103.86(9) . . ?
C13 C11 C7 112.28(9) . . ?
C12 C11 C10 112.55(9) . . ?
C12 C11 C7 113.27(9) . . ?
C12 C11 C13 111.06(10) . . ?
N5 C14 C13 102.47(9) . . ?
N5 C14 H14A 107.3(8) . . ?
N5 C14 H14B 108.2(8) . . ?
C13 C14 H14A 111.2(8) . . ?
C13 C14 H14B 115.7(8) . . ?
H14A C14 H14B 111.3(11) . . ?
C10 C9 H9A 112.7(8) . . ?
C10 C9 H9B 109.1(8) . . ?
C8 C9 C10 103.99(8) . . ?
C8 C9 H9A 113.0(8) . . ?
C8 C9 H9B 109.7(8) . . ?
H9A C9 H9B 108.2(11) . . ?
C11 C13 H13A 110.1(7) . . ?
C11 C13 H13B 110.5(8) . . ?
C14 C13 C11 104.01(9) . . ?
C14 C13 H13A 107.6(7) . . ?
C14 C13 H13B 112.1(8) . . ?
H13A C13 H13B 112.2(11) . . ?
C3 C2 H2 127.8(9) . . ?
C1 C2 C3 106.30(11) . . ?
C1 C2 H2 125.8(9) . . ?
N1 C1 H1A 119.9(9) . . ?
C2 C1 N1 110.07(11) . . ?
C2 C1 H1A 129.9(9) . . ?
C11 C12 H12A 109.8(9) . . ?
C11 C12 H12B 109.2(9) . . ?
C11 C12 H12C 109.9(9) . . ?
H12A C12 H12B 109.5(12) . . ?
H12A C12 H12C 109.9(12) . . ?
H12B C12 H12C 108.5(13) . . ?
C15 C16 H16A 110.6(13) . . ?
C15 C16 H16B 112.2(12) . . ?
C15 C16 H16C 109.1(14) . . ?
H16A C16 H16B 110.7(18) . . ?
H16A C16 H16C 107.0(18) . . ?
H16B C16 H16C 107.0(19) . . ?
H5C O5A H5D 89(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C10 C11 C7 125.35(9) . . . . ?
N5 C10 C11 C13 8.02(11) . . . . ?
N5 C10 C11 C12 -112.19(10) . . . . ?
N5 C10 C9 C8 -94.51(10) . . . . ?
N5 C14 C13 C11 41.13(11) . . . . ?
N4 C6 C3 C4 179.79(10) . . . . ?
N4 C6 C3 C2 2.3(2) . . . . ?
N4 C7 C8 C9 169.70(9) . . . . ?
N4 C7 C11 C10 -154.28(9) . . . . ?
N4 C7 C11 C13 -43.05(13) . . . . ?
N4 C7 C11 C12 83.74(12) . . . . ?
N3 C6 C3 C4 0.85(15) . . . . ?
N3 C6 C3 C2 -176.67(12) . . . . ?
C6 N4 C7 C8 143.04(10) . . . . ?
C6 N4 C7 C11 -97.77(12) . . . . ?
C6 N3 C5 N2 0.04(18) . . . . ?
C6 C3 C4 N2 0.32(16) . . . . ?
C6 C3 C4 N1 -178.54(9) . . . . ?
C6 C3 C2 C1 177.81(13) . . . . ?
C3 C2 C1 N1 0.05(15) . . . . ?
C4 N2 C5 N3 1.04(17) . . . . ?
C4 N1 C1 C2 -0.24(15) . . . . ?
C4 C3 C2 C1 0.14(14) . . . . ?
C10 N5 C14 C13 -36.52(11) . . . . ?
C10 C11 C13 C14 -30.18(11) . . . . ?
C7 N4 C6 N3 6.80(16) . . . . ?
C7 N4 C6 C3 -172.13(10) . . . . ?
C7 C8 C9 C10 -40.02(11) . . . . ?
C7 C11 C13 C14 -141.00(9) . . . . ?
C5 N3 C6 N4 -179.99(10) . . . . ?
C5 N3 C6 C3 -1.03(15) . . . . ?
C5 N2 C4 N1 177.48(10) . . . . ?
C5 N2 C4 C3 -1.19(15) . . . . ?
C8 C7 C11 C10 -30.45(10) . . . . ?
C8 C7 C11 C13 80.78(11) . . . . ?
C8 C7 C11 C12 -152.43(10) . . . . ?
C11 C10 C9 C8 21.24(11) . . . . ?
C11 C7 C8 C9 44.12(10) . . . . ?
C14 N5 C10 C11 17.60(11) . . . . ?
C14 N5 C10 C9 134.17(9) . . . . ?
C9 C10 C11 C7 5.61(11) . . . . ?
C9 C10 C11 C13 -111.72(9) . . . . ?
C9 C10 C11 C12 128.07(10) . . . . ?
C2 C3 C4 N2 178.56(10) . . . . ?
C2 C3 C4 N1 -0.29(12) . . . . ?
C1 N1 C4 N2 -178.53(11) . . . . ?
C1 N1 C4 C3 0.33(13) . . . . ?
C12 C11 C13 C14 91.04(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O4 0.862(16) 2.038(16) 2.8835(13) 166.6(13) 1_645 yes
N5 H5A O2 0.953(15) 1.801(15) 2.7300(12) 164.1(13) 2_557 yes
N1 H1 O3 0.847(16) 1.991(17) 2.8175(13) 165.0(14) 2_666 yes
N5 H5B O1 0.962(16) 1.725(16) 2.6571(12) 162.2(14) . yes
O3 H3A N2 0.86(2) 1.93(2) 2.7806(13) 169.8(16) 1_456 yes
O3 H3B O1 0.856(19) 1.841(19) 2.6894(12) 170.9(16) . yes
O4 H4A O2 0.88(2) 1.91(2) 2.7894(13) 172.4(18) 1_565 yes
O4 H4B O5 0.96(2) 1.85(2) 2.800(3) 168.9(17) . yes
O4 H4B O5A 0.96(2) 1.71(2) 2.627(10) 157.8(19) . yes
O5 H5C O3 0.88(2) 1.89(2) 2.7655(17) 171(2) . yes
O5A H5C O3 1.01(2) 1.89(2) 2.760(10) 142(2) . yes
O5 H5D N3 0.89(2) 2.06(2) 2.952(2) 171.7(18) 2_566 yes
O5A H5D N3 1.04(3) 2.06(2) 2.866(9) 132(2) 2_566 yes

#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#



#----------------------------------------------------------------------------#
#                   SHELX HKL FILE                                           #
#----------------------------------------------------------------------------#


# END of CIF
####################################################################### 
# 
# 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_21JLR017_MK-065(22-55)
_database_code_depnum_ccdc_archive 'CCDC 2482162'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;

_audit_creation_date             2021-12-06T15:20:37-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C19 H25 N O5'
_chemical_formula_sum            'C19 H25 N O5'
_chemical_formula_weight         347.4

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.32883(17)
_cell_length_b                   12.61335(13)
_cell_length_c                   13.40303(17)
_cell_angle_alpha                65.3764(11)
_cell_angle_beta                 76.8583(11)
_cell_angle_gamma                86.5176(10)
_cell_volume                     1843.76(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    54597
_cell_measurement_theta_min      3.678
_cell_measurement_theta_max      79.769

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0554
1 1 1 0.0953
-1 1 -1 0.0514
1 -1 1 0.0663
0 -1 0 0.058
0 1 0 0.035
-1 0 -1 0.0764
1 0 1 0.0819
-1 1 0 0.0377
1 -1 0 0.0499
0 -1 -1 0.0929
0 1 1 0.0955
-1 1 1 0.061
1 0 0 0.0539
-1 0 0 0.0303
-1 0 1 0.0765
0 0 1 0.096
0 0 -1 0.0836
-1 -1 1 0.0672
-1 -1 0 0.0589
1 1 0 0.0589
5 -3 -6 0.0739
-2 -5 -8 0.0894

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0003 1.0005 -1 -0.2148 0.0569 -0.0035
1.0006 0.9998 1.0001 -0.0294 -0.0014 0.1732
-1.0001 1.0006 -0.9999 -0.2198 -0.044 -0.0829
1.0001 -1.0006 0.9999 0.2198 0.044 0.0829
-0.0003 -1.0002 -0.0001 0.1246 0.0227 -0.0451
0.0003 1.0002 0.0001 -0.1246 -0.0227 0.0451
-1.0003 0.0004 -1 -0.0952 -0.0213 -0.128
1.0003 -0.0004 1 0.0952 0.0213 0.128
-1.0001 1.0002 0.0001 -0.1297 -0.1235 -0.0342
1.0001 -1.0002 -0.0001 0.1297 0.1235 0.0342
-0.0003 -0.9999 -1.0002 0.0345 0.1023 -0.0938
0.0003 0.9999 1.0002 -0.0345 -0.1023 0.0938
-1.0001 0.9999 1.0002 -0.0395 -0.2031 0.0144
1.0004 -0.0001 -0.0001 0.005 0.1009 0.0794
-1.0004 0.0001 0.0001 -0.005 -0.1009 -0.0794
-1.0004 -0.0003 1.0002 0.0851 -0.1805 -0.0307
0 -0.0003 1.0001 0.0901 -0.0796 0.0487
0 0.0003 -1.0001 -0.0901 0.0796 -0.0487
-1.0006 -1.0004 1.0001 0.2097 -0.1578 -0.0758
-1.0006 -1.0001 0 0.1196 -0.0782 -0.1245
1.0006 1.0001 0 -0.1196 0.0782 0.1245
5.001 -2.9989 -6.0012 -0.1418 1.0499 -0.0306
-2.002 -4.9983 -8.001 -0.1081 0.5483 -0.7737


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.58861
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.94
_oxdiff_exptl_absorpt_empirical_details 
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.757

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0050367
_diffrn_orient_matrix_ub_12      -0.124618
_diffrn_orient_matrix_ub_13      0.090098
_diffrn_orient_matrix_ub_21      0.100838
_diffrn_orient_matrix_ub_22      -0.022686
_diffrn_orient_matrix_ub_23      -0.0795826
_diffrn_orient_matrix_ub_31      0.0793459
_diffrn_orient_matrix_ub_32      0.0450958
_diffrn_orient_matrix_ub_33      0.0486811
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_number            72714
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.684
_diffrn_reflns_theta_max         73.993
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             7471
_reflns_number_gt                6984
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
        List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00  -3.00   0.50    0.60    --  -23.00 -69.00-159.00  184
  2  ω    -42.00  50.00   0.50    0.60    --  -23.00  69.00 -26.00  184
  3  ω     29.00 120.00   0.50    0.60    --   47.95  69.00 -26.00  182
  4  ω     94.00 177.00   0.50    2.00    --  113.25  69.00 -26.00  166
  5  ω     42.00  81.00   0.50    2.00    --  113.25 -69.00-159.00   78
  6  ω    -70.00 -12.00   0.50    0.60    --  -23.00 125.00-120.00  116
  7  ω    -95.00 -10.00   0.50    0.60    --  -23.00 -45.00 -30.00  170
  8  ω     -2.00  28.00   0.50    0.60    --   30.00  97.00 -42.74   60
  9  ω      5.00  42.00   0.50    0.60    --   34.00  91.00 100.11   74
 10  ω      8.00  41.00   0.50    0.60    --   38.00  92.00   9.16   66
 11  ω     13.00  42.00   0.50    0.60    --   42.00  91.00 118.45   58
 12  ω     17.00  43.00   0.50    0.60    --   46.00  90.00-107.70   52
 13  ω    -24.00  67.00   0.50    0.60    --   47.95 -69.00-159.00  182
 14  ω     -1.00  81.00   0.50    0.60    --   47.95 -99.00 150.00  164
 15  ω     28.00 122.00   0.50    0.60    --   50.00  76.00-136.87  188
 16  ω     28.00 122.00   0.50    0.60    --   50.00  75.00   5.11  188
 17  ω     31.00 126.00   0.50    0.60    --   54.00  77.00  22.64  190
 18  ω     36.00 131.00   0.50    0.60    --   58.00  76.00 -68.47  190
 19  ω     35.00 131.00   0.50    0.60    --   58.00  77.00  69.23  192
 20  ω     36.00 131.00   0.50    0.60    --   58.00  75.00 170.64  190
 21  ω     36.00 131.00   0.50    0.60    --   58.00  76.00 -98.83  190
 22  ω     40.00 135.00   0.50    0.60    --   62.00  76.00 -53.83  190
 23  ω     46.00 139.00   0.50    0.60    --   66.00  71.00  31.66  186
 24  ω     44.00 139.00   0.50    0.60    --   66.00  75.00  46.26  190
 25  ω     43.00 139.00   0.50    0.60    --   66.00  77.00 171.30  192
 26  ω     44.00 139.00   0.50    0.60    --   66.00  76.00-166.50  190
 27  ω     44.00 139.00   0.50    0.60    --   66.00  75.00 102.10  190
 28  ω     48.00 143.00   0.50    0.60    --   70.00  76.00 -49.29  190
 29  ω     51.00 143.00   0.50    0.60    --   70.00  67.00 144.09  184
 30  ω     47.00 143.00   0.50    0.60    --   70.00  77.00-143.32  192
 31  ω     48.00 143.00   0.50    0.60    --   70.00  75.00-121.85  190
 32  ω     48.00 143.00   0.50    0.60    --   70.00  75.00 -20.40  190
 33  ω     52.00 146.00   0.50    0.60    --   74.00  76.00  70.84  188
 34  ω     59.00 151.00   0.50    0.60    --   78.00  69.00-175.14  184
 35  ω     56.00 151.00   0.50    0.60    --   78.00  76.00-115.72  190
 36  ω     55.00 151.00   0.50    0.60    --   78.00  77.00 -18.23  192
 37  ω     57.00 151.00   0.50    0.60    --   78.00  74.00 148.38  188
 38  ω     64.00 151.00   0.50    0.60    --   78.00  54.00  44.10  174
 39  ω     61.00  97.00   0.50    2.00    --   82.00  72.00-107.16   72
 40  ω    116.00 158.00   0.50    2.00    --   86.00  57.00-162.10   84
 41  ω     72.00 108.00   0.50    2.00    --   86.00  57.00-162.10   72
 42  ω     73.00  99.00   0.50    2.00    --   90.00  64.00  51.73   52
 43  ω    137.00 162.00   0.50    2.00    --   90.00  72.00 -53.82   50
 44  ω     75.00 102.00   0.50    2.00    --   90.00  65.00  91.21   54
 45  ω     69.00 116.00   0.50    2.00    --   90.00  72.00 -53.82   94
 46  ω     72.00 108.00   0.50    2.00    --   94.00  76.00  55.04   72
 47  ω    137.00 163.00   0.50    2.00    --   94.00  59.00 136.14   52
 48  ω    141.00 167.00   0.50    2.00    --   94.00  76.00  55.04   52
 49  ω     80.00 106.00   0.50    2.00    --   94.00  59.00 136.14   52
 50  ω    140.00 175.00   0.50    2.00    --  106.00  62.00-112.17   70
 51  ω     89.00 127.00   0.50    2.00    --  106.00  62.00-112.17   76
 52  ω    142.00 176.00   0.50    2.00    --  113.25  77.00-120.00   68
 53  ω     92.00 129.00   0.50    2.00    --  113.25  77.00-120.00   74
 54  ω     49.00 104.00   0.50    2.00    --  113.25 -94.00  60.00  110
 55  ω     76.00 104.00   0.50    2.00    --  113.25 -94.00 120.00   56
 56  ω     98.00 169.00   0.50    2.00    --  113.25  61.00 -30.00  142
 57  ω     44.00  71.00   0.50    2.00    --  113.25 -94.00 120.00   54
 58  ω     92.00 158.00   0.50    2.00    --  113.25  77.00  60.00  132
 59  ω     81.00 106.00   0.50    2.00    --  113.25 -94.00-150.00   50
 60  ω     54.00 105.00   0.50    2.00    --  113.25 -94.00 -90.00  102
 61  ω    105.00 131.00   0.50    2.00    --  113.25  61.00 -60.00   52
 62  ω     50.00  77.00   0.50    2.00    --  113.25 -94.00-150.00   54
 63  ω     76.00 104.00   0.50    2.00    --  113.25 -94.00   0.00   56
 64  ω     42.00 102.00   0.50    2.00    --  113.25 -94.00 -60.00  120
 65  ω     42.00  72.00   0.50    2.00    --  113.25 -94.00   0.00   60
 66  ω    141.00 172.00   0.50    2.00    --  113.25  61.00 -90.00   62
 67  ω    152.00 177.00   0.50    2.00    --  113.25  61.00  90.00   50
 68  ω     98.00 125.00   0.50    2.00    --  113.25  61.00  90.00   54
 69  ω     98.00 125.00   0.50    2.00    --  113.25  61.00 -90.00   54
 70  ω    127.00 170.00   0.50    2.00    --  113.25  70.00 177.55   86
 71  ω     48.00 101.00   0.50    2.00    --  113.25 -77.00   0.00  106
 72  ω     99.00 151.00   0.50    2.00    --  113.25  61.00 120.00  104
 73  ω     94.00 120.00   0.50    2.00    --  113.25  70.00 177.55   52
 74  ω     75.00 106.00   0.50    2.00    --  113.25 -94.00 150.00   62
 75  ω     45.00  72.00   0.50    2.00    --  113.25 -94.00 150.00   54
 76  ω     98.00 149.00   0.50    2.00    --  113.25  61.00-150.00  102
 77  ω     74.00 104.00   0.50    2.00    --  113.25 -94.00  90.00   60
 78  ω     44.00  75.00   0.50    2.00    --  113.25 -77.00  60.00   62
 79  ω     79.00 106.00   0.50    2.00    --  113.25 -97.00  -7.71   54
 80  ω    141.00 177.00   0.50    2.00    --  113.25  77.00 120.00   72
 81  ω    140.00 172.00   0.50    2.00    --  113.25  77.00-150.00   64
 82  ω     93.00 126.00   0.50    2.00    --  113.25  77.00 120.00   66
 83  ω     91.00 123.00   0.50    2.00    --  113.25  77.00-150.00   64
 84  ω     44.00  76.00   0.50    2.00    --  113.25 -97.00  -7.71   64
 85  ω     93.00 147.00   0.50    2.00    --  113.25  77.00  30.00  108
 86  ω    117.00 177.00   0.50    2.00    --  113.25  90.00  63.51  120
 87  ω    135.00 177.00   0.50    2.00    --  113.25  77.00-180.00   84
 88  ω     93.00 123.00   0.50    2.00    --  113.25  77.00-180.00   60
 89  ω    129.00 177.00   0.50    2.00    --  113.25  77.00 150.00   96
 90  ω    100.00 176.00   0.50    2.00    --  113.25  61.00  30.00  152
 91  ω     94.00 163.00   0.50    2.00    --  113.25  68.00  -6.36  138
 92  ω     97.00 160.00   0.50    2.00    --  113.25  61.00 150.00  126
 93  ω     91.00 120.00   0.50    2.00    --  113.25  77.00 150.00   58
 94  ω     78.00 104.00   0.50    2.00    --  113.25 -94.00-180.00   52
 95  ω    131.00 177.00   0.50    2.00    --  113.25  30.00-120.00   92
 96  ω     44.00  84.00   0.50    2.00    --  113.25 -77.00-120.00   80
 97  ω     42.00  74.00   0.50    2.00    --  113.25 -94.00-180.00   64
 98  ω    148.00 176.00   0.50    2.00    --  113.25  73.00 -82.00   56
 99  ω    134.00 175.00   0.50    2.00    --  113.25  77.00 -60.00   82
100  ω     93.00 124.00   0.50    2.00    --  113.25  77.00 -60.00   62
101  ω    125.00 176.00   0.50    2.00    --  113.25  77.00  90.00  102
102  ω    151.00 176.00   0.50    2.00    --  113.25  77.00   0.00   50
103  ω     91.00 121.00   0.50    2.00    --  113.25  77.00   0.00   60
104  ω     91.00 117.00   0.50    2.00    --  113.25  77.00  90.00   52
105  ω     92.00 126.00   0.50    2.00    --  113.25  73.00 -82.00   68
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.3909P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00096(14)
_refine_ls_number_reflns         7471
_refine_ls_number_parameters     652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.033
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.086
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.03
_olex2_refinement_description    
;
;

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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
O9 O 0.31037(6) 0.40526(6) 0.36625(6) 0.03366(16) Uani 1 1 d . . . . .
O2 O 0.40825(6) 0.08250(6) 0.85771(6) 0.03628(17) Uani 1 1 d . . . . .
O4 O 0.48165(6) 0.35321(7) 0.84973(6) 0.03827(17) Uani 1 1 d . . . . .
O3 O 0.26856(7) 0.48391(7) 0.69574(6) 0.04082(18) Uani 1 1 d . . . . .
O8 O 0.55830(6) 0.35878(7) 0.19124(7) 0.04248(18) Uani 1 1 d . . . . .
O7 O 0.12282(6) 0.68817(7) -0.02137(7) 0.04183(19) Uani 1 1 d . . . . .
O5 O 0.41971(7) 0.35466(7) 0.52045(6) 0.04193(19) Uani 1 1 d . . . . .
O1 O 0.37880(8) -0.00205(7) 0.74502(7) 0.0486(2) Uani 1 1 d . . . . .
O10 O 0.36830(8) 0.38594(8) 0.01984(7) 0.0505(2) Uani 1 1 d . . . . .
O6 O -0.04746(7) 0.69312(9) 0.08551(8) 0.0571(2) Uani 1 1 d . . . . .
N1 N 0.52733(7) 0.12236(7) 0.69252(7) 0.03210(18) Uani 1 1 d . . . . .
N2 N 0.10318(7) 0.63180(8) 0.16346(8) 0.0387(2) Uani 1 1 d . . . . .
C15 C 0.46623(8) 0.36527(8) 0.67598(8) 0.02684(19) Uani 1 1 d . . . . .
C34 C 0.33634(8) 0.41493(8) 0.18539(8) 0.02729(19) Uani 1 1 d . . . . .
C16 C 0.42248(8) 0.37930(8) 0.77246(8) 0.02867(19) Uani 1 1 d . . . . .
C19 C 0.39284(8) 0.37770(8) 0.60421(8) 0.0301(2) Uani 1 1 d . . . . .
C35 C 0.37356(8) 0.38795(8) 0.28102(8) 0.02710(19) Uani 1 1 d . . . . .
C14 C 0.58318(8) 0.32678(9) 0.65031(8) 0.0301(2) Uani 1 1 d . . . . .
C6 C 0.64527(9) 0.01910(8) 0.58499(8) 0.0328(2) Uani 1 1 d . . . . .
C38 C 0.40168(9) 0.37909(9) 0.10319(8) 0.0333(2) Uani 1 1 d . . . . .
C13 C 0.59626(8) 0.19598(9) 0.71574(8) 0.0312(2) Uani 1 1 d . . . . .
C33 C 0.22392(8) 0.46536(9) 0.17298(9) 0.0320(2) Uani 1 1 d . . . . .
C8 C 0.43310(9) 0.06221(9) 0.76395(8) 0.0342(2) Uani 1 1 d . . . . .
C17 C 0.30737(9) 0.42307(10) 0.79603(9) 0.0354(2) Uani 1 1 d . . . . .
C32 C 0.21812(8) 0.59323(9) 0.15456(9) 0.0321(2) Uani 1 1 d . . . . .
C9 C 0.30926(9) 0.02539(9) 0.94679(8) 0.0343(2) Uani 1 1 d . . . . .
C36 C 0.48370(9) 0.33319(10) 0.29586(9) 0.0360(2) Uani 1 1 d . . . . .
C7 C 0.56245(10) 0.11273(10) 0.58539(8) 0.0367(2) Uani 1 1 d . . . . .
C27 C 0.05091(8) 0.67248(9) 0.07602(10) 0.0389(2) Uani 1 1 d . . . . .
C5 C 0.68752(10) -0.05024(9) 0.67820(9) 0.0391(2) Uani 1 1 d . . . . .
C18 C 0.27593(9) 0.41517(10) 0.63427(10) 0.0386(2) Uani 1 1 d . . . . .
C25 C 0.06197(9) 0.67376(10) 0.33318(10) 0.0415(3) Uani 1 1 d . . . . .
C37 C 0.51212(10) 0.32526(11) 0.12120(10) 0.0415(2) Uani 1 1 d . . . . .
C11 C 0.31849(11) 0.06700(11) 1.03580(10) 0.0430(3) Uani 1 1 d . . . . .
C1 C 0.68229(11) 0.00375(10) 0.48607(10) 0.0434(3) Uani 1 1 d . . . . .
C28 C 0.08616(9) 0.73245(10) -0.12834(10) 0.0417(3) Uani 1 1 d . . . . .
C4 C 0.76746(11) -0.13108(10) 0.67191(12) 0.0471(3) Uani 1 1 d . . . . .
C20 C 0.09865(10) 0.62424(11) 0.43283(10) 0.0453(3) Uani 1 1 d . . . . .
C10 C 0.31621(11) -0.10677(10) 0.99280(10) 0.0434(3) Uani 1 1 d . . . . .
C26 C 0.03653(10) 0.59887(11) 0.27780(10) 0.0449(3) Uani 1 1 d . . . . .
C12 C 0.20449(11) 0.06835(13) 0.90314(13) 0.0513(3) Uani 1 1 d . . . . .
C21 C 0.11940(11) 0.69059(12) 0.48729(12) 0.0517(3) Uani 1 1 d . . . . .
C24 C 0.04817(12) 0.79420(12) 0.28785(12) 0.0557(3) Uani 1 1 d . . . . .
C3 C 0.80482(12) -0.14435(11) 0.57274(13) 0.0554(3) Uani 1 1 d . . . . .
C2 C 0.76110(13) -0.07769(12) 0.48036(12) 0.0576(4) Uani 1 1 d . . . . .
C22 C 0.10425(11) 0.80972(13) 0.44177(13) 0.0556(3) Uani 1 1 d . . . . .
C23 C 0.06941(13) 0.86060(13) 0.34180(14) 0.0629(4) Uani 1 1 d . . . . .
C31 C 0.19417(13) 0.74769(16) -0.21395(12) 0.0615(4) Uani 1 1 d . . . . .
C30 C 0.0335(2) 0.84932(17) -0.15160(18) 0.0849(6) Uani 1 1 d . . . . .
C29 C 0.0097(2) 0.6435(2) -0.12654(19) 0.0892(7) Uani 1 1 d . . . . .
H13A H 0.5758(9) 0.1754(10) 0.7963(10) 0.030(3) Uiso 1 1 d . . . . .
H32A H 0.2482(10) 0.6052(10) 0.2127(10) 0.031(3) Uiso 1 1 d . . . . .
H13B H 0.6754(11) 0.1778(10) 0.6948(10) 0.036(3) Uiso 1 1 d . . . . .
H32B H 0.2622(11) 0.6426(11) 0.0809(11) 0.039(3) Uiso 1 1 d . . . . .
H14A H 0.6052(10) 0.3469(10) 0.5699(11) 0.034(3) Uiso 1 1 d . . . . .
H17A H 0.2549(11) 0.3566(11) 0.8503(11) 0.038(3) Uiso 1 1 d . . . . .
H33A H 0.1686(11) 0.4190(11) 0.2429(11) 0.042(3) Uiso 1 1 d . . . . .
H36A H 0.5178(11) 0.3644(11) 0.3375(11) 0.041(3) Uiso 1 1 d . . . . .
H7A H 0.5983(11) 0.1903(12) 0.5259(11) 0.046(3) Uiso 1 1 d . . . . .
H18A H 0.2267(11) 0.3417(12) 0.6786(11) 0.045(3) Uiso 1 1 d . . . . .
H14B H 0.6336(11) 0.3686(11) 0.6705(10) 0.038(3) Uiso 1 1 d . . . . .
H5 H 0.6628(11) -0.0412(12) 0.7478(12) 0.049(4) Uiso 1 1 d . . . . .
H37A H 0.5000(12) 0.2380(13) 0.1530(12) 0.050(4) Uiso 1 1 d . . . . .
H33B H 0.2056(11) 0.4576(11) 0.1088(11) 0.045(3) Uiso 1 1 d . . . . .
H36B H 0.4693(11) 0.2461(12) 0.3393(11) 0.043(3) Uiso 1 1 d . . . . .
H7B H 0.4950(12) 0.0989(12) 0.5638(11) 0.047(3) Uiso 1 1 d . . . . .
H4A H 0.7950(12) -0.1785(13) 0.7386(13) 0.055(4) Uiso 1 1 d . . . . .
H11A H 0.2534(13) 0.0346(13) 1.1009(13) 0.056(4) Uiso 1 1 d . . . . .
H26A H -0.0411(13) 0.6038(13) 0.2720(12) 0.058(4) Uiso 1 1 d . . . . .
H17B H 0.3081(10) 0.4768(11) 0.8304(11) 0.041(3) Uiso 1 1 d . . . . .
H10A H 0.3043(12) -0.1360(12) 0.9365(12) 0.053(4) Uiso 1 1 d . . . . .
H10B H 0.3892(13) -0.1316(13) 1.0117(12) 0.055(4) Uiso 1 1 d . . . . .
H18B H 0.2502(12) 0.4600(12) 0.5662(12) 0.049(4) Uiso 1 1 d . . . . .
H26B H 0.0503(11) 0.5127(13) 0.3253(12) 0.050(4) Uiso 1 1 d . . . . .
H1 H 0.6517(12) 0.0514(13) 0.4213(13) 0.054(4) Uiso 1 1 d . . . . .
H11B H 0.3173(13) 0.1516(14) 1.0059(12) 0.056(4) Uiso 1 1 d . . . . .
H11C H 0.3909(13) 0.0415(13) 1.0615(12) 0.056(4) Uiso 1 1 d . . . . .
H10C H 0.2568(13) -0.1409(13) 1.0621(13) 0.057(4) Uiso 1 1 d . . . . .
H12A H 0.2041(13) 0.0499(14) 0.8383(14) 0.064(4) Uiso 1 1 d . . . . .
H20 H 0.1096(13) 0.5402(14) 0.4643(13) 0.058(4) Uiso 1 1 d . . . . .
H37B H 0.5649(12) 0.3497(12) 0.0494(12) 0.050(4) Uiso 1 1 d . . . . .
H12B H 0.1402(15) 0.0305(15) 0.9630(15) 0.073(5) Uiso 1 1 d . . . . .
H21 H 0.1438(14) 0.6541(15) 0.5602(15) 0.072(5) Uiso 1 1 d . . . . .
H24 H 0.0223(13) 0.8249(14) 0.2214(14) 0.063(4) Uiso 1 1 d . . . . .
H31A H 0.1782(13) 0.7721(14) -0.2914(14) 0.068(5) Uiso 1 1 d . . . . .
H3 H 0.8621(14) -0.2005(14) 0.5691(13) 0.065(4) Uiso 1 1 d . . . . .
H9 H 0.3486(14) 0.3855(15) 0.4262(15) 0.071(5) Uiso 1 1 d . . . . .
H2 H 0.7837(15) -0.0875(15) 0.4117(15) 0.076(5) Uiso 1 1 d . . . . .
H22 H 0.1185(14) 0.8600(14) 0.4808(14) 0.067(5) Uiso 1 1 d . . . . .
H12C H 0.1990(15) 0.1555(17) 0.8781(15) 0.077(5) Uiso 1 1 d . . . . .
H4 H 0.4423(15) 0.3673(15) 0.9130(15) 0.078(5) Uiso 1 1 d . . . . .
H23 H 0.0607(15) 0.9437(17) 0.3101(16) 0.084(5) Uiso 1 1 d . . . . .
H31B H 0.2499(19) 0.809(2) -0.2140(18) 0.107(7) Uiso 1 1 d . . . . .
H31C H 0.231(2) 0.673(2) -0.194(2) 0.119(8) Uiso 1 1 d . . . . .
H29A H -0.0602(18) 0.6377(18) -0.0701(18) 0.092(6) Uiso 1 1 d . . . . .
H29B H -0.0050(19) 0.670(2) -0.200(2) 0.107(7) Uiso 1 1 d . . . . .
H30A H 0.0310(17) 0.8808(18) -0.2301(18) 0.090(6) Uiso 1 1 d . . . . .
H30B H -0.042(3) 0.845(2) -0.099(3) 0.150(11) Uiso 1 1 d . . . . .
H29C H 0.046(3) 0.565(3) -0.102(3) 0.152(12) Uiso 1 1 d . . . . .
H30C H 0.085(3) 0.897(3) -0.143(3) 0.160(13) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O9 C35 1.3199(11) . ?
O9 H9 0.959(18) . ?
O2 C8 1.3498(12) . ?
O2 C9 1.4702(12) . ?
O4 C16 1.3203(12) . ?
O4 H4 0.956(19) . ?
O3 C17 1.4187(13) . ?
O3 C18 1.4109(13) . ?
O8 C36 1.4103(13) . ?
O8 C37 1.4096(14) . ?
O7 C27 1.3449(14) . ?
O7 C28 1.4725(13) . ?
O5 C19 1.2432(12) . ?
O1 C8 1.2182(13) . ?
O10 C38 1.2446(13) . ?
O6 C27 1.2141(13) . ?
N1 C13 1.4624(13) . ?
N1 C8 1.3557(14) . ?
N1 C7 1.4561(12) . ?
N2 C32 1.4652(12) . ?
N2 C27 1.3617(14) . ?
N2 C26 1.4611(15) . ?
C15 C16 1.3625(13) . ?
C15 C19 1.4218(13) . ?
C15 C14 1.5038(13) . ?
C34 C35 1.3617(13) . ?
C34 C38 1.4263(13) . ?
C34 C33 1.5043(13) . ?
C16 C17 1.5049(14) . ?
C19 C18 1.5084(14) . ?
C35 C36 1.5016(13) . ?
C14 C13 1.5308(14) . ?
C14 H14A 0.974(12) . ?
C14 H14B 0.986(13) . ?
C6 C7 1.5145(15) . ?
C6 C5 1.3882(15) . ?
C6 C1 1.3898(14) . ?
C38 C37 1.5080(16) . ?
C13 H13A 0.973(12) . ?
C13 H13B 0.993(13) . ?
C33 C32 1.5263(14) . ?
C33 H33A 0.993(13) . ?
C33 H33B 0.980(14) . ?
C17 H17A 0.997(13) . ?
C17 H17B 0.967(13) . ?
C32 H32A 1.002(12) . ?
C32 H32B 0.971(13) . ?
C9 C11 1.5174(15) . ?
C9 C10 1.5220(15) . ?
C9 C12 1.5161(16) . ?
C36 H36A 0.976(13) . ?
C36 H36B 1.010(13) . ?
C7 H7A 1.015(14) . ?
C7 H7B 0.988(14) . ?
C5 C4 1.3892(16) . ?
C5 H5 0.966(14) . ?
C18 H18A 1.013(14) . ?
C18 H18B 0.966(14) . ?
C25 C20 1.3870(17) . ?
C25 C26 1.5060(19) . ?
C25 C24 1.3972(17) . ?
C37 H37A 1.008(14) . ?
C37 H37B 0.968(15) . ?
C11 H11A 0.999(15) . ?
C11 H11B 0.971(16) . ?
C11 H11C 1.016(16) . ?
C1 C2 1.3840(18) . ?
C1 H1 0.971(15) . ?
C28 C31 1.510(2) . ?
C28 C30 1.512(2) . ?
C28 C29 1.4983(19) . ?
C4 C3 1.380(2) . ?
C4 H4A 0.969(15) . ?
C20 C21 1.385(2) . ?
C20 H20 0.977(16) . ?
C10 H10A 1.007(15) . ?
C10 H10B 0.988(16) . ?
C10 H10C 0.990(16) . ?
C26 H26A 0.974(16) . ?
C26 H26B 1.032(14) . ?
C12 H12A 0.990(17) . ?
C12 H12B 0.968(18) . ?
C12 H12C 1.009(19) . ?
C21 C22 1.385(2) . ?
C21 H21 1.000(18) . ?
C24 C23 1.382(2) . ?
C24 H24 0.934(16) . ?
C3 C2 1.383(2) . ?
C3 H3 0.977(16) . ?
C2 H2 0.956(18) . ?
C22 C23 1.380(2) . ?
C22 H22 1.019(17) . ?
C23 H23 0.96(2) . ?
C31 H31A 1.016(17) . ?
C31 H31B 1.07(2) . ?
C31 H31C 0.98(3) . ?
C30 H30A 0.96(2) . ?
C30 H30B 1.02(3) . ?
C30 H30C 0.96(3) . ?
C29 H29A 0.99(2) . ?
C29 H29B 0.96(2) . ?
C29 H29C 1.01(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C35 O9 H9 110.7(10) . . ?
C8 O2 C9 120.34(8) . . ?
C16 O4 H4 111.9(11) . . ?
C18 O3 C17 110.83(8) . . ?
C37 O8 C36 111.47(8) . . ?
C27 O7 C28 121.30(8) . . ?
C8 N1 C13 124.53(8) . . ?
C8 N1 C7 117.71(9) . . ?
C7 N1 C13 117.76(8) . . ?
C27 N2 C32 123.73(9) . . ?
C27 N2 C26 118.99(9) . . ?
C26 N2 C32 115.76(9) . . ?
C16 C15 C19 116.93(9) . . ?
C16 C15 C14 122.41(8) . . ?
C19 C15 C14 120.39(8) . . ?
C35 C34 C38 117.05(9) . . ?
C35 C34 C33 121.73(8) . . ?
C38 C34 C33 120.70(8) . . ?
O4 C16 C15 119.75(9) . . ?
O4 C16 C17 117.71(8) . . ?
C15 C16 C17 122.54(9) . . ?
O5 C19 C15 122.72(9) . . ?
O5 C19 C18 118.82(9) . . ?
C15 C19 C18 118.41(8) . . ?
O9 C35 C34 120.10(8) . . ?
O9 C35 C36 117.79(8) . . ?
C34 C35 C36 122.05(8) . . ?
C15 C14 C13 113.46(8) . . ?
C15 C14 H14A 108.4(7) . . ?
C15 C14 H14B 109.1(7) . . ?
C13 C14 H14A 109.4(7) . . ?
C13 C14 H14B 107.3(7) . . ?
H14A C14 H14B 109.1(10) . . ?
C5 C6 C7 122.94(9) . . ?
C5 C6 C1 118.64(10) . . ?
C1 C6 C7 118.41(10) . . ?
O10 C38 C34 122.16(10) . . ?
O10 C38 C37 118.94(9) . . ?
C34 C38 C37 118.81(9) . . ?
N1 C13 C14 113.48(8) . . ?
N1 C13 H13A 107.5(7) . . ?
N1 C13 H13B 108.0(7) . . ?
C14 C13 H13A 110.0(7) . . ?
C14 C13 H13B 108.5(7) . . ?
H13A C13 H13B 109.2(10) . . ?
C34 C33 C32 113.92(8) . . ?
C34 C33 H33A 107.9(7) . . ?
C34 C33 H33B 107.8(8) . . ?
C32 C33 H33A 108.3(7) . . ?
C32 C33 H33B 109.2(8) . . ?
H33A C33 H33B 109.6(11) . . ?
O2 C8 N1 111.38(9) . . ?
O1 C8 O2 124.93(10) . . ?
O1 C8 N1 123.69(9) . . ?
O3 C17 C16 111.64(8) . . ?
O3 C17 H17A 110.5(7) . . ?
O3 C17 H17B 107.3(8) . . ?
C16 C17 H17A 110.0(7) . . ?
C16 C17 H17B 109.9(8) . . ?
H17A C17 H17B 107.3(10) . . ?
N2 C32 C33 111.60(8) . . ?
N2 C32 H32A 107.3(7) . . ?
N2 C32 H32B 108.8(7) . . ?
C33 C32 H32A 110.5(7) . . ?
C33 C32 H32B 110.5(7) . . ?
H32A C32 H32B 108.1(10) . . ?
O2 C9 C11 102.07(8) . . ?
O2 C9 C10 110.68(9) . . ?
O2 C9 C12 109.96(9) . . ?
C11 C9 C10 110.08(9) . . ?
C12 C9 C11 110.94(10) . . ?
C12 C9 C10 112.63(10) . . ?
O8 C36 C35 111.44(8) . . ?
O8 C36 H36A 107.4(8) . . ?
O8 C36 H36B 110.6(7) . . ?
C35 C36 H36A 109.4(8) . . ?
C35 C36 H36B 107.8(7) . . ?
H36A C36 H36B 110.2(10) . . ?
N1 C7 C6 114.87(8) . . ?
N1 C7 H7A 108.6(7) . . ?
N1 C7 H7B 107.8(8) . . ?
C6 C7 H7A 107.7(8) . . ?
C6 C7 H7B 110.2(8) . . ?
H7A C7 H7B 107.4(11) . . ?
O7 C27 N2 111.10(8) . . ?
O6 C27 O7 124.97(11) . . ?
O6 C27 N2 123.92(11) . . ?
C6 C5 C4 120.72(11) . . ?
C6 C5 H5 120.0(8) . . ?
C4 C5 H5 119.2(8) . . ?
O3 C18 C19 112.77(9) . . ?
O3 C18 H18A 111.2(8) . . ?
O3 C18 H18B 108.4(8) . . ?
C19 C18 H18A 107.2(8) . . ?
C19 C18 H18B 109.4(8) . . ?
H18A C18 H18B 107.9(11) . . ?
C20 C25 C26 120.54(11) . . ?
C20 C25 C24 117.66(13) . . ?
C24 C25 C26 121.79(12) . . ?
O8 C37 C38 112.84(8) . . ?
O8 C37 H37A 111.7(8) . . ?
O8 C37 H37B 107.5(8) . . ?
C38 C37 H37A 107.4(8) . . ?
C38 C37 H37B 109.4(8) . . ?
H37A C37 H37B 108.0(11) . . ?
C9 C11 H11A 109.3(9) . . ?
C9 C11 H11B 110.5(9) . . ?
C9 C11 H11C 110.3(8) . . ?
H11A C11 H11B 107.9(12) . . ?
H11A C11 H11C 110.3(12) . . ?
H11B C11 H11C 108.5(12) . . ?
C6 C1 H1 118.6(9) . . ?
C2 C1 C6 120.51(12) . . ?
C2 C1 H1 120.9(9) . . ?
O7 C28 C31 102.80(9) . . ?
O7 C28 C30 110.85(12) . . ?
O7 C28 C29 109.72(12) . . ?
C31 C28 C30 109.64(14) . . ?
C29 C28 C31 110.96(15) . . ?
C29 C28 C30 112.46(18) . . ?
C5 C4 H4A 118.7(9) . . ?
C3 C4 C5 120.12(12) . . ?
C3 C4 H4A 121.1(9) . . ?
C25 C20 H20 118.0(9) . . ?
C21 C20 C25 121.70(12) . . ?
C21 C20 H20 120.3(9) . . ?
C9 C10 H10A 110.7(8) . . ?
C9 C10 H10B 110.9(9) . . ?
C9 C10 H10C 107.7(9) . . ?
H10A C10 H10B 109.3(12) . . ?
H10A C10 H10C 109.1(12) . . ?
H10B C10 H10C 109.0(12) . . ?
N2 C26 C25 113.51(10) . . ?
N2 C26 H26A 106.2(9) . . ?
N2 C26 H26B 108.3(8) . . ?
C25 C26 H26A 111.2(9) . . ?
C25 C26 H26B 109.7(8) . . ?
H26A C26 H26B 107.7(12) . . ?
C9 C12 H12A 110.4(9) . . ?
C9 C12 H12B 108.9(10) . . ?
C9 C12 H12C 111.2(10) . . ?
H12A C12 H12B 109.5(14) . . ?
H12A C12 H12C 108.3(14) . . ?
H12B C12 H12C 108.5(14) . . ?
C20 C21 C22 119.89(13) . . ?
C20 C21 H21 121.4(10) . . ?
C22 C21 H21 118.7(10) . . ?
C25 C24 H24 115.7(10) . . ?
C23 C24 C25 120.68(13) . . ?
C23 C24 H24 123.6(10) . . ?
C4 C3 C2 119.50(12) . . ?
C4 C3 H3 119.2(9) . . ?
C2 C3 H3 121.3(9) . . ?
C1 C2 H2 118.6(11) . . ?
C3 C2 C1 120.48(12) . . ?
C3 C2 H2 120.9(11) . . ?
C21 C22 H22 121.1(9) . . ?
C23 C22 C21 119.13(14) . . ?
C23 C22 H22 119.7(9) . . ?
C24 C23 H23 120.7(11) . . ?
C22 C23 C24 120.93(13) . . ?
C22 C23 H23 118.4(11) . . ?
C28 C31 H31A 109.7(9) . . ?
C28 C31 H31B 111.4(12) . . ?
C28 C31 H31C 109.0(14) . . ?
H31A C31 H31B 111.1(15) . . ?
H31A C31 H31C 107.9(16) . . ?
H31B C31 H31C 107.6(18) . . ?
C28 C30 H30A 104.9(12) . . ?
C28 C30 H30B 114.0(16) . . ?
C28 C30 H30C 105.9(19) . . ?
H30A C30 H30B 113.9(19) . . ?
H30A C30 H30C 108(2) . . ?
H30B C30 H30C 109(2) . . ?
C28 C29 H29A 107.8(12) . . ?
C28 C29 H29B 108.1(14) . . ?
C28 C29 H29C 108.9(18) . . ?
H29A C29 H29B 110.6(18) . . ?
H29A C29 H29C 109(2) . . ?
H29B C29 H29C 113(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O9 C35 C36 O8 -157.94(9) . . . . ?
O4 C16 C17 O3 160.04(9) . . . . ?
O5 C19 C18 O3 -154.68(9) . . . . ?
O10 C38 C37 O8 158.88(10) . . . . ?
C15 C16 C17 O3 -20.44(14) . . . . ?
C15 C19 C18 O3 28.07(13) . . . . ?
C15 C14 C13 N1 60.48(11) . . . . ?
C34 C35 C36 O8 24.85(14) . . . . ?
C34 C38 C37 O8 -24.32(14) . . . . ?
C34 C33 C32 N2 -169.67(8) . . . . ?
C16 C15 C19 O5 -172.04(9) . . . . ?
C16 C15 C19 C18 5.10(13) . . . . ?
C16 C15 C14 C13 76.70(12) . . . . ?
C19 C15 C16 O4 170.70(9) . . . . ?
C19 C15 C16 C17 -8.81(14) . . . . ?
C19 C15 C14 C13 -97.17(10) . . . . ?
C35 C34 C38 O10 170.66(10) . . . . ?
C35 C34 C38 C37 -6.03(14) . . . . ?
C35 C34 C33 C32 74.15(12) . . . . ?
C14 C15 C16 O4 -3.37(14) . . . . ?
C14 C15 C16 C17 177.13(9) . . . . ?
C14 C15 C19 O5 2.15(14) . . . . ?
C14 C15 C19 C18 179.29(9) . . . . ?
C6 C5 C4 C3 -0.83(18) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C38 C34 C35 O9 -171.46(9) . . . . ?
C38 C34 C35 C36 5.69(14) . . . . ?
C38 C34 C33 C32 -114.31(10) . . . . ?
C13 N1 C8 O2 2.47(13) . . . . ?
C13 N1 C8 O1 -177.27(10) . . . . ?
C13 N1 C7 C6 86.27(11) . . . . ?
C33 C34 C35 O9 0.37(14) . . . . ?
C33 C34 C35 C36 177.52(9) . . . . ?
C33 C34 C38 O10 -1.26(15) . . . . ?
C33 C34 C38 C37 -177.95(9) . . . . ?
C8 O2 C9 C11 176.79(9) . . . . ?
C8 O2 C9 C10 59.67(12) . . . . ?
C8 O2 C9 C12 -65.41(12) . . . . ?
C8 N1 C13 C14 -105.25(11) . . . . ?
C8 N1 C7 C6 -93.59(12) . . . . ?
C17 O3 C18 C19 -57.71(12) . . . . ?
C32 N2 C27 O7 -8.89(15) . . . . ?
C32 N2 C27 O6 172.07(11) . . . . ?
C32 N2 C26 C25 77.82(12) . . . . ?
C9 O2 C8 O1 -0.02(16) . . . . ?
C9 O2 C8 N1 -179.76(8) . . . . ?
C36 O8 C37 C38 55.57(12) . . . . ?
C7 N1 C13 C14 74.91(11) . . . . ?
C7 N1 C8 O2 -177.69(8) . . . . ?
C7 N1 C8 O1 2.57(15) . . . . ?
C7 C6 C5 C4 -176.83(11) . . . . ?
C7 C6 C1 C2 177.56(12) . . . . ?
C27 O7 C28 C31 174.29(11) . . . . ?
C27 O7 C28 C30 57.21(17) . . . . ?
C27 O7 C28 C29 -67.60(18) . . . . ?
C27 N2 C32 C33 -85.99(12) . . . . ?
C27 N2 C26 C25 -115.69(12) . . . . ?
C5 C6 C7 N1 -1.89(15) . . . . ?
C5 C6 C1 C2 -1.10(17) . . . . ?
C5 C4 C3 C2 -0.8(2) . . . . ?
C18 O3 C17 C16 53.41(12) . . . . ?
C25 C20 C21 C22 -0.45(18) . . . . ?
C25 C24 C23 C22 -0.3(2) . . . . ?
C37 O8 C36 C35 -55.36(12) . . . . ?
C1 C6 C7 N1 179.52(10) . . . . ?
C1 C6 C5 C4 1.77(17) . . . . ?
C28 O7 C27 O6 -0.56(17) . . . . ?
C28 O7 C27 N2 -179.59(9) . . . . ?
C4 C3 C2 C1 1.5(2) . . . . ?
C20 C25 C26 N2 -120.89(11) . . . . ?
C20 C25 C24 C23 -0.69(19) . . . . ?
C20 C21 C22 C23 -0.53(19) . . . . ?
C26 N2 C32 C33 79.79(12) . . . . ?
C26 N2 C27 O7 -174.23(10) . . . . ?
C26 N2 C27 O6 6.72(17) . . . . ?
C26 C25 C20 C21 -178.01(11) . . . . ?
C26 C25 C24 C23 178.36(12) . . . . ?
C21 C22 C23 C24 0.9(2) . . . . ?
C24 C25 C20 C21 1.06(17) . . . . ?
C24 C25 C26 N2 60.09(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C17 H17A O6 0.997(13) 2.533(13) 3.3548(14) 139.5(9) 2_566 yes
C36 H36A O5 0.976(13) 2.430(13) 3.0546(13) 121.4(10) . yes
C17 H17B O10 0.967(13) 2.576(13) 3.0973(13) 113.9(9) 1_556 yes
C10 H10A O1 1.007(15) 2.406(14) 2.9449(14) 112.7(10) . yes
C12 H12A O1 0.990(17) 2.433(16) 3.0272(17) 118.0(12) . yes
O9 H9 O5 0.959(18) 1.603(18) 2.5611(10) 176.4(16) . yes
O4 H4 O10 0.956(19) 1.612(19) 2.5665(11) 175.8(17) 1_556 yes
C29 H29A O6 0.99(2) 2.50(2) 3.080(3) 117.1(15) . yes
C30 H30B O6 1.02(3) 2.40(3) 2.925(2) 110(2) . yes


#----------------------------------------------------------------------------#
#                       SHELX RES FILE                                       #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                       SHELX HKL FILE                                       #
#----------------------------------------------------------------------------#


# END of CIF
####################################################################### 
# 
# 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_22JLR009_KM-113-01-F1-(30-38)
_database_code_depnum_ccdc_archive 'CCDC 2482163'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;

_audit_creation_date             2022-07-22T09:40:40-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H30 N2 O2'
_chemical_formula_sum            'C20 H30 N2 O2'
_chemical_formula_weight         330.46

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.73159(14)
_cell_length_b                   10.58664(16)
_cell_length_c                   10.70354(16)
_cell_angle_alpha                78.4669(13)
_cell_angle_beta                 74.0757(13)
_cell_angle_gamma                68.5821(14)
_cell_volume                     981.04(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    172.99(10)
_cell_measurement_reflns_used    26106
_cell_measurement_theta_min      4.301
_cell_measurement_theta_max      79.54

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.124
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_F_000             360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 0 0.0804
-1 1 0 0.058
0 -1 -1 0.1009
1 -1 -1 0.0842
-1 0 0 0.0956
1 0 0 0.0826
-1 -1 -1 0.09
1 1 1 0.104
-1 0 1 0.107
1 0 -1 0.0954
-1 -1 0 0.1434
1 1 0 0.1137
0 0 -1 0.1139
0 0 1 0.1075
0 -1 1 0.117
0 1 -1 0.0873
0 -1 0 0.0991
0 1 0 0.1123
1 -1 1 0.0656
-1 1 -1 0.058
1 0 1 0.0606
-1 0 -1 0.075
0 -6 -3 0.0758
3 5 6 0.1034


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.90772
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.933

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      172.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1670972
_diffrn_orient_matrix_ub_12      -0.0920136
_diffrn_orient_matrix_ub_13      -0.0249031
_diffrn_orient_matrix_ub_21      0.0398667
_diffrn_orient_matrix_ub_22      0.1051844
_diffrn_orient_matrix_ub_23      -0.1130244
_diffrn_orient_matrix_ub_31      0.0297821
_diffrn_orient_matrix_ub_32      0.0721872
_diffrn_orient_matrix_ub_33      0.0963805
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_number            37418
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.322
_diffrn_reflns_theta_max         70.419
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3730
_reflns_number_gt                3504
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0799P)²+0.2697P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3730
_refine_ls_number_parameters     307
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.60766(12) 0.78124(10) 0.94176(12) 0.0513(3) Uani 1 1 d . . . . .
O1 O 0.61696(14) 0.56997(11) 1.04496(12) 0.0555(3) Uani 1 1 d . . . . .
N2 N 0.4526(4) 0.6813(5) 0.9145(4) 0.0463(7) Uani 0.803(3) 1 d . . P A 1
N1 N 0.26879(19) 0.78069(17) 0.55128(16) 0.0659(4) Uani 1 1 d . . . . .
C16 C 0.56586(17) 0.66909(15) 0.97015(15) 0.0466(4) Uani 1 1 d . . . . .
C17 C 0.72630(18) 0.78911(16) 0.99777(18) 0.0523(4) Uani 1 1 d . . . . .
C6 C 0.1486(2) 0.7667(2) 0.38221(19) 0.0664(5) Uani 1 1 d . . . . .
C18 C 0.7427(2) 0.92597(18) 0.9322(2) 0.0644(5) Uani 1 1 d . . . . .
H18A H 0.771719 0.924741 0.837115 0.097 Uiso 1 1 calc R U . . .
H18B H 0.820816 0.942379 0.961866 0.097 Uiso 1 1 calc R U . . .
H18C H 0.646029 0.998899 0.95537 0.097 Uiso 1 1 calc R U . . .
C11 C 0.3014(4) 0.8738(3) 0.6217(3) 0.0557(7) Uani 0.803(3) 1 d . . P A 1
H11 H 0.326919 0.950141 0.559339 0.067 Uiso 0.803(3) 1 calc R U P A 1
C20 C 0.6718(2) 0.7902(2) 1.1442(2) 0.0692(5) Uani 1 1 d . . . . .
H20A H 0.572276 0.860388 1.164103 0.104 Uiso 1 1 calc R U . . .
H20B H 0.743818 0.810206 1.179191 0.104 Uiso 1 1 calc R U . . .
H20C H 0.664022 0.700634 1.18427 0.104 Uiso 1 1 calc R U . . .
C19 C 0.8729(2) 0.67480(19) 0.9587(2) 0.0703(6) Uani 1 1 d . . . . .
H19A H 0.861593 0.587343 1.00224 0.105 Uiso 1 1 calc R U . . .
H19B H 0.954384 0.689527 0.98486 0.105 Uiso 1 1 calc R U . . .
H19C H 0.897791 0.67349 0.863735 0.105 Uiso 1 1 calc R U . . .
C14 C 0.3802(3) 0.7960(2) 0.8297(3) 0.0471(5) Uani 0.803(3) 1 d . . P A 1
H14 H 0.396731 0.878472 0.846262 0.056 Uiso 0.803(3) 1 calc R U P A 1
C7 C 0.2075(2) 0.8516(2) 0.4362(2) 0.0724(6) Uani 1 1 d . . . . .
H7A H 0.287778 0.876901 0.367693 0.087 Uiso 1 1 calc R U . . .
H7B H 0.124447 0.936966 0.460156 0.087 Uiso 1 1 calc R U . . .
C13 C 0.2103(4) 0.8254(4) 0.8541(4) 0.0576(7) Uani 0.803(3) 1 d . . P A 1
H13A H 0.1564 0.865133 0.937476 0.069 Uiso 0.803(3) 1 calc R U P A 1
H13B H 0.186364 0.742021 0.854805 0.069 Uiso 0.803(3) 1 calc R U P A 1
C10 C 0.4390(2) 0.7810(2) 0.6828(3) 0.0541(6) Uani 0.803(3) 1 d . . P A 1
C3 C 0.0363(3) 0.6098(3) 0.2854(3) 0.0878(7) Uani 1 1 d . . . . .
H3 H -0.002247 0.555613 0.252614 0.105 Uiso 1 1 calc R U . . .
C1 C 0.2177(3) 0.7180(3) 0.2625(2) 0.0804(6) Uani 1 1 d . . . . .
H1 H 0.305522 0.738239 0.212113 0.096 Uiso 1 1 calc R U . . .
C2 C 0.1605(3) 0.6402(3) 0.2152(2) 0.0900(7) Uani 1 1 d . . . . .
H2A H 0.209014 0.60768 0.132295 0.108 Uiso 1 1 calc R U . . .
C5 C 0.0207(3) 0.7349(3) 0.4530(3) 0.0878(7) Uani 1 1 d . . . . .
H5 H -0.029169 0.767322 0.535778 0.105 Uiso 1 1 calc R U . . .
C12 C 0.1710(3) 0.9293(2) 0.7359(3) 0.0615(6) Uani 0.803(3) 1 d . . P A 1
H12A H 0.073188 0.934716 0.720415 0.074 Uiso 0.803(3) 1 calc R U P A 1
H12B H 0.165124 1.021201 0.749239 0.074 Uiso 0.803(3) 1 calc R U P A 1
C4 C -0.0341(3) 0.6578(3) 0.4051(3) 0.1001(8) Uani 1 1 d . . . . .
H4 H -0.121835 0.636972 0.454708 0.12 Uiso 1 1 calc R U . . .
C9 C 0.4660(3) 0.6400(3) 0.6490(2) 0.0728(8) Uani 0.803(3) 1 d . . P A 1
H9A H 0.575055 0.58572 0.633031 0.087 Uiso 0.803(3) 1 calc R U P A 1
H9B H 0.40971 0.589995 0.719998 0.087 Uiso 0.803(3) 1 calc R U P A 1
C8 C 0.4068(3) 0.6695(3) 0.5255(3) 0.0795(8) Uani 0.803(3) 1 d . . P A 1
H8A H 0.479347 0.695348 0.448824 0.095 Uiso 0.803(3) 1 calc R U P A 1
H8B H 0.388146 0.588986 0.509121 0.095 Uiso 0.803(3) 1 calc R U P A 1
C15 C 0.5792(3) 0.8249(4) 0.6292(3) 0.0858(9) Uani 0.803(3) 1 d . . P A 1
H15A H 0.613862 0.816717 0.535203 0.129 Uiso 0.803(3) 1 calc R U P A 1
H15B H 0.659595 0.766087 0.673952 0.129 Uiso 0.803(3) 1 calc R U P A 1
H15C H 0.553984 0.919926 0.644005 0.129 Uiso 0.803(3) 1 calc R U P A 1
C21 C 0.3124(11) 0.7907(10) 0.7352(10) 0.059(2) Uani 0.197(3) 1 d . . P A 2
C22 C 0.2686(15) 0.6631(14) 0.7409(11) 0.081(4) Uani 0.197(3) 1 d . . P A 2
H22A H 0.359757 0.581742 0.722778 0.097 Uiso 0.197(3) 1 calc R U P A 2
H22B H 0.20533 0.644375 0.827499 0.097 Uiso 0.197(3) 1 calc R U P A 2
C23 C 0.1813(17) 0.7006(15) 0.6360(13) 0.091(4) Uani 0.197(3) 1 d . . P A 2
H23A H 0.18911 0.620398 0.59694 0.11 Uiso 0.197(3) 1 calc R U P A 2
H23B H 0.07378 0.755262 0.665809 0.11 Uiso 0.197(3) 1 calc R U P A 2
C28 C 0.4576(15) 0.7650(12) 0.7650(12) 0.064(3) Uani 0.197(3) 1 d . . P A 2
H28 H 0.46603 0.853697 0.774817 0.077 Uiso 0.197(3) 1 calc R U P A 2
C27 C 0.5815(14) 0.7039(17) 0.6357(13) 0.090(4) Uani 0.197(3) 1 d . U P A 2
H27A H 0.682568 0.70737 0.63294 0.108 Uiso 0.197(3) 1 calc R U P A 2
H27B H 0.589615 0.609015 0.630568 0.108 Uiso 0.197(3) 1 calc R U P A 2
C26 C 0.5120(17) 0.8007(18) 0.5313(16) 0.105(4) Uani 0.197(3) 1 d . U P A 2
H26A H 0.549708 0.758928 0.448265 0.125 Uiso 0.197(3) 1 calc R U P A 2
H26B H 0.538484 0.885164 0.516994 0.125 Uiso 0.197(3) 1 calc R U P A 2
C24 C 0.337(2) 0.835(2) 0.577(2) 0.099(6) Uani 0.197(3) 1 d . U P A 2
H24 H 0.287511 0.93539 0.559724 0.118 Uiso 0.197(3) 1 calc R U P A 2
C25 C 0.195(2) 0.880(2) 0.8162(16) 0.086(5) Uani 0.197(3) 1 d . . P A 2
H25A H 0.098784 0.895581 0.793554 0.129 Uiso 0.197(3) 1 calc R U P A 2
H25B H 0.190598 0.840924 0.907578 0.129 Uiso 0.197(3) 1 calc R U P A 2
H25C H 0.213317 0.967593 0.804165 0.129 Uiso 0.197(3) 1 calc R U P A 2
N2A N 0.4947(19) 0.665(2) 0.8827(18) 0.052(4) Uani 0.197(3) 1 d . U P A 2
H2 H 0.436(2) 0.610(2) 0.919(2) 0.062(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C16 1.3446(18) . ?
O2 C17 1.4729(18) . ?
O1 C16 1.2211(18) . ?
N2 C16 1.347(5) . ?
N2 C14 1.442(5) . ?
N2 H2 0.82(2) . ?
N1 C11 1.516(4) . ?
N1 C7 1.464(2) . ?
N1 C8 1.428(3) . ?
N1 C23 1.436(13) . ?
N1 C24 1.13(2) . ?
C16 N2A 1.32(2) . ?
C17 C18 1.523(2) . ?
C17 C20 1.511(3) . ?
C17 C19 1.513(2) . ?
C6 C7 1.496(3) . ?
C6 C1 1.377(3) . ?
C6 C5 1.387(3) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C11 H11 1 . ?
C11 C10 1.565(3) . ?
C11 C12 1.530(4) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C14 H14 1 . ?
C14 C13 1.523(4) . ?
C14 C10 1.538(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C13 C12 1.536(4) . ?
C10 C9 1.518(3) . ?
C10 C15 1.527(3) . ?
C3 H3 0.95 . ?
C3 C2 1.348(4) . ?
C3 C4 1.376(4) . ?
C1 H1 0.95 . ?
C1 C2 1.379(4) . ?
C2 H2A 0.95 . ?
C5 H5 0.95 . ?
C5 C4 1.359(4) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C4 H4 0.95 . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C9 C8 1.516(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C21 C22 1.545(14) . ?
C21 C28 1.451(14) . ?
C21 C24 1.64(2) . ?
C21 C25 1.40(2) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C22 C23 1.496(16) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C28 H28 1 . ?
C28 C27 1.63(2) . ?
C28 N2A 1.51(2) . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C27 C26 1.486(19) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C26 C24 1.56(2) . ?
C24 H24 1 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
N2A H2 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O2 C17 120.57(12) . . ?
C16 N2 C14 127.2(4) . . ?
C16 N2 H2 114.3(15) . . ?
C14 N2 H2 117.4(15) . . ?
C7 N1 C11 112.94(17) . . ?
C8 N1 C11 105.4(2) . . ?
C8 N1 C7 114.94(18) . . ?
C23 N1 C7 112.7(5) . . ?
C24 N1 C7 111.7(10) . . ?
C24 N1 C23 129.3(11) . . ?
O2 C16 N2 112.6(2) . . ?
O1 C16 O2 124.31(14) . . ?
O1 C16 N2 122.9(2) . . ?
O1 C16 N2A 122.9(10) . . ?
N2A C16 O2 110.6(9) . . ?
O2 C17 C18 101.98(13) . . ?
O2 C17 C20 109.79(14) . . ?
O2 C17 C19 110.47(14) . . ?
C20 C17 C18 111.01(15) . . ?
C20 C17 C19 112.93(16) . . ?
C19 C17 C18 110.12(15) . . ?
C1 C6 C7 122.0(2) . . ?
C1 C6 C5 118.0(2) . . ?
C5 C6 C7 120.0(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C11 H11 110.8 . . ?
N1 C11 C10 105.4(2) . . ?
N1 C11 C12 112.4(2) . . ?
C10 C11 H11 110.8 . . ?
C12 C11 H11 110.8 . . ?
C12 C11 C10 106.4(2) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C14 H14 107.9 . . ?
N2 C14 C13 113.1(3) . . ?
N2 C14 C10 114.9(2) . . ?
C13 C14 H14 107.9 . . ?
C13 C14 C10 104.8(2) . . ?
C10 C14 H14 107.9 . . ?
N1 C7 C6 112.55(17) . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C14 C13 H13A 111.5 . . ?
C14 C13 H13B 111.5 . . ?
C14 C13 C12 101.4(2) . . ?
H13A C13 H13B 109.3 . . ?
C12 C13 H13A 111.5 . . ?
C12 C13 H13B 111.5 . . ?
C14 C10 C11 103.86(19) . . ?
C9 C10 C11 103.4(2) . . ?
C9 C10 C14 113.70(19) . . ?
C9 C10 C15 111.9(2) . . ?
C15 C10 C11 113.2(2) . . ?
C15 C10 C14 110.4(2) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C6 C1 H1 119.7 . . ?
C6 C1 C2 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C11 C12 C13 104.2(2) . . ?
C11 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C13 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109 . . ?
C8 C9 C10 103.5(2) . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
N1 C8 C9 104.0(2) . . ?
N1 C8 H8A 110.9 . . ?
N1 C8 H8B 110.9 . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 109 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C21 C24 98.1(10) . . ?
C28 C21 C22 115.7(9) . . ?
C28 C21 C24 105.2(11) . . ?
C25 C21 C22 108.1(12) . . ?
C25 C21 C28 111.6(12) . . ?
C25 C21 C24 117.8(12) . . ?
C21 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109 . . ?
C23 C22 C21 103.5(9) . . ?
C23 C22 H22A 111.1 . . ?
C23 C22 H22B 111.1 . . ?
N1 C23 C22 94.8(8) . . ?
N1 C23 H23A 112.8 . . ?
N1 C23 H23B 112.8 . . ?
C22 C23 H23A 112.8 . . ?
C22 C23 H23B 112.8 . . ?
H23A C23 H23B 110.2 . . ?
C21 C28 H28 109 . . ?
C21 C28 C27 104.4(10) . . ?
C21 C28 N2A 117.2(11) . . ?
C27 C28 H28 109 . . ?
N2A C28 H28 109 . . ?
N2A C28 C27 108.0(11) . . ?
C28 C27 H27A 111.7 . . ?
C28 C27 H27B 111.7 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 C28 100.2(11) . . ?
C26 C27 H27A 111.7 . . ?
C26 C27 H27B 111.7 . . ?
C27 C26 H26A 110.2 . . ?
C27 C26 H26B 110.2 . . ?
C27 C26 C24 107.6(12) . . ?
H26A C26 H26B 108.5 . . ?
C24 C26 H26A 110.2 . . ?
C24 C26 H26B 110.2 . . ?
N1 C24 C21 100.3(13) . . ?
N1 C24 C26 125.7(19) . . ?
N1 C24 H24 108.8 . . ?
C21 C24 H24 108.8 . . ?
C26 C24 C21 103.0(14) . . ?
C26 C24 H24 108.8 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 N2A C28 129.1(17) . . ?
C16 N2A H2 109(2) . . ?
C28 N2A H2 118(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C16 N2A C28 -0.6(16) . . . . ?
O1 C16 N2A C28 -164.4(11) . . . . ?
N2 C14 C13 C12 -169.2(3) . . . . ?
N2 C14 C10 C11 153.5(3) . . . . ?
N2 C14 C10 C9 41.9(3) . . . . ?
N2 C14 C10 C15 -84.9(3) . . . . ?
N1 C11 C10 C14 -122.6(2) . . . . ?
N1 C11 C10 C9 -3.7(3) . . . . ?
N1 C11 C10 C15 117.6(3) . . . . ?
N1 C11 C12 C13 91.6(2) . . . . ?
C16 O2 C17 C18 176.10(14) . . . . ?
C16 O2 C17 C20 -66.13(19) . . . . ?
C16 O2 C17 C19 59.1(2) . . . . ?
C16 N2 C14 C13 -141.7(3) . . . . ?
C16 N2 C14 C10 98.1(4) . . . . ?
C17 O2 C16 O1 2.4(2) . . . . ?
C17 O2 C16 N2 177.8(2) . . . . ?
C17 O2 C16 N2A -161.1(7) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
C11 N1 C7 C6 -169.2(2) . . . . ?
C11 N1 C8 C9 40.3(3) . . . . ?
C11 C10 C9 C8 27.0(3) . . . . ?
C14 N2 C16 O2 1.7(4) . . . . ?
C14 N2 C16 O1 177.2(3) . . . . ?
C14 C13 C12 C11 40.9(3) . . . . ?
C14 C10 C9 C8 138.9(2) . . . . ?
C7 N1 C11 C10 -148.98(19) . . . . ?
C7 N1 C11 C12 95.5(2) . . . . ?
C7 N1 C8 C9 165.4(2) . . . . ?
C7 N1 C23 C22 -173.9(7) . . . . ?
C7 N1 C24 C21 151.3(7) . . . . ?
C7 N1 C24 C26 -94.4(18) . . . . ?
C7 C6 C1 C2 -179.83(19) . . . . ?
C7 C6 C5 C4 180.0(2) . . . . ?
C13 C14 C10 C11 28.8(2) . . . . ?
C13 C14 C10 C9 -82.8(2) . . . . ?
C13 C14 C10 C15 150.4(2) . . . . ?
C10 C11 C12 C13 -23.4(3) . . . . ?
C10 C14 C13 C12 -43.3(3) . . . . ?
C10 C9 C8 N1 -42.7(3) . . . . ?
C1 C6 C7 N1 -112.1(2) . . . . ?
C1 C6 C5 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C5 C6 C7 N1 68.0(3) . . . . ?
C5 C6 C1 C2 0.0(3) . . . . ?
C12 C11 C10 C14 -3.1(3) . . . . ?
C12 C11 C10 C9 115.9(2) . . . . ?
C12 C11 C10 C15 -122.9(3) . . . . ?
C4 C3 C2 C1 0.4(4) . . . . ?
C8 N1 C11 C10 -22.7(3) . . . . ?
C8 N1 C11 C12 -138.2(2) . . . . ?
C8 N1 C7 C6 69.8(3) . . . . ?
C15 C10 C9 C8 -95.1(3) . . . . ?
C21 C22 C23 N1 33.9(12) . . . . ?
C21 C28 C27 C26 44.9(12) . . . . ?
C21 C28 N2A C16 -141.7(13) . . . . ?
C22 C21 C28 C27 74.1(11) . . . . ?
C22 C21 C28 N2A -45.3(17) . . . . ?
C22 C21 C24 N1 21.3(15) . . . . ?
C22 C21 C24 C26 -109.3(14) . . . . ?
C23 N1 C7 C6 -38.8(7) . . . . ?
C23 N1 C24 C21 2(2) . . . . ?
C23 N1 C24 C26 116.1(18) . . . . ?
C28 C21 C22 C23 -146.2(11) . . . . ?
C28 C21 C24 N1 140.8(13) . . . . ?
C28 C21 C24 C26 10.3(16) . . . . ?
C28 C27 C26 C24 -37.8(17) . . . . ?
C27 C28 N2A C16 100.8(16) . . . . ?
C27 C26 C24 N1 -94(2) . . . . ?
C27 C26 C24 C21 19.1(19) . . . . ?
C24 N1 C7 C6 166.4(11) . . . . ?
C24 N1 C23 C22 -25(2) . . . . ?
C24 C21 C22 C23 -34.9(13) . . . . ?
C24 C21 C28 C27 -32.9(12) . . . . ?
C24 C21 C28 N2A -152.4(14) . . . . ?
C25 C21 C22 C23 87.9(13) . . . . ?
C25 C21 C28 C27 -161.8(12) . . . . ?
C25 C21 C28 N2A 78.8(17) . . . . ?
C25 C21 C24 N1 -94.1(17) . . . . ?
C25 C21 C24 C26 135.3(16) . . . . ?
N2A C28 C27 C26 170.3(13) . . . . ?

#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   SHELX HKL FILE                                           #
#----------------------------------------------------------------------------#


# END of CIF
####################################################################### 
# 
# 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_22JLR022_KM-174-F1
_database_code_depnum_ccdc_archive 'CCDC 2482166'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;

_audit_creation_date             2023-02-07T16:58:13-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C17 H20 N6 O'
_chemical_formula_sum            'C17 H20 N6 O'
_chemical_formula_weight         324.39

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2112(2)
_cell_length_b                   18.3624(5)
_cell_length_c                   10.9157(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.184(2)
_cell_angle_gamma                90
_cell_volume                     1643.30(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    13619
_cell_measurement_theta_min      4.69
_cell_measurement_theta_max      78.692

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.0669
1 -1 1 0.0555
1 0 0 0.0364
-1 0 0 0.0405
-1 1 0 0.0447
1 -1 0 0.034
0 -1 0 0.0199
0 1 0 0.0463
1 -1 -1 0.0419
-1 1 1 0.0745
1 0 -1 0.0497
0 1 1 0.072
-1 -1 0 0.0309
1 1 0 0.0345
-1 -1 1 0.066
1 1 -1 0.0561
0 0 -1 0.0497
0 0 1 0.0703
1 1 1 0.0591
-1 -1 -1 0.0499
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0007 -0.9984 1.0001 -0.1471 0.0255 -0.0683
0.9994 -0.9986 1.0009 -0.2373 -0.0018 0.0943
1.0002 -0.0003 0.0008 -0.0902 -0.0272 0.1626
-1.0002 0.0003 -0.0008 0.0902 0.0272 -0.1626
-0.9999 0.9987 -0.0010 0.1328 0.0907 -0.1283
0.9999 -0.9987 0.0010 -0.1328 -0.0907 0.1283
-0.0003 -0.9984 0.0002 -0.0426 -0.0634 -0.0343
0.0003 0.9984 -0.0002 0.0426 0.0634 0.0343
1.0004 -0.9988 -0.9989 -0.0283 -0.1796 0.1624
-1.0004 0.9988 0.9989 0.0283 0.1796 -0.1624
1.0007 -0.0003 -0.9991 0.0143 -0.1161 0.1967
-0.0002 0.9985 0.9998 -0.0619 0.1524 0.0002
-1.0005 -0.9982 -0.0007 0.0476 -0.0362 -0.1969
1.0005 0.9982 0.0007 -0.0476 0.0362 0.1969
-1.0009 -0.9981 0.9993 -0.0569 0.0527 -0.2309
1.0009 0.9981 -0.9993 0.0569 -0.0527 0.2309
0.0005 -0.0001 -0.9999 0.1045 -0.0889 0.0341
-0.0005 0.0001 0.9999 -0.1045 0.0889 -0.0341
1.0000 0.9983 1.0006 -0.1521 0.1251 0.1628
-1.0000 -0.9983 -1.0006 0.1521 -0.1251 -0.1628

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
        Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.962
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.956
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 4.557
_oxdiff_exptl_absorpt_empirical_full_min 0.411

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0900818
_diffrn_orient_matrix_ub_12      0.0426979
_diffrn_orient_matrix_ub_13      -0.1045366
_diffrn_orient_matrix_ub_21      -0.0272564
_diffrn_orient_matrix_ub_22      0.0635691
_diffrn_orient_matrix_ub_23      0.0888924
_diffrn_orient_matrix_ub_31      0.1626056
_diffrn_orient_matrix_ub_32      0.0342753
_diffrn_orient_matrix_ub_33      -0.0339943
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_number            30043
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.718
_diffrn_reflns_theta_max         74.501
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             3369
_reflns_number_gt                3058
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  43.00   0.50    1.30    --  -23.00  90.00 -66.00  190
  2  ω    -20.00  76.00   0.50    1.30    --   47.42 -90.00 179.00  192
  3  ω    101.00 177.00   0.50   10.00    --  113.25  90.00 -66.00  152
  4  ω     42.00 105.00   0.50   10.00    --  113.25 -90.00 179.00  126
  5  ω    -46.00  50.00   0.50    1.30    --  -23.00  77.00   0.00  192
  6  ω    -95.00 -10.00   0.50    1.30    --  -23.00 -45.00-150.00  170
  7  ω    -68.00 -12.00   0.50    1.30    --  -23.00 125.00  90.00  112
  8  ω    -27.00  23.00   0.50    1.30    --   47.42 -19.00-180.00  100
  9  ω     33.00 119.00   0.50    1.30    --   47.42  57.00   0.00  172
 10  ω    -25.00  40.00   0.50    1.30    --   47.42 -38.00-120.00  130
 11  ω    -27.00  23.00   0.50    1.30    --   47.42 -19.00   0.00  100
 12  ω    -25.00  40.00   0.50    1.30    --   47.42 -38.00-180.00  130
 13  ω     42.00 106.00   0.50   10.00    --  113.25 -94.00 -90.00  128
 14  ω    101.00 177.00   0.50   10.00    --  113.25  30.00-150.00  152
 15  ω    101.00 177.00   0.50   10.00    --  113.25  45.00 -90.00  152
 16  ω     42.00 102.00   0.50   10.00    --  113.25 -77.00-180.00  120
 17  ω    101.00 177.00   0.50   10.00    --  113.25  45.00 -30.00  152
 18  ω    101.00 177.00   0.50   10.00    --  113.25  30.00  60.00  152
 19  ω     42.00  68.00   0.50   10.00    --  113.25 -61.00 -60.00   52
 20  ω     91.00 177.00   0.50   10.00    --  113.25  77.00 -90.00  172
 21  ω     42.00 102.00   0.50   10.00    --  113.25 -77.00  90.00  120
 22  ω     42.00  68.00   0.50   10.00    --  113.25 -61.00 120.00   52
 23  ω     42.00 106.00   0.50   10.00    --  113.25 -94.00 120.00  128
 24  ω     42.00  68.00   0.50   10.00    --  113.25 -61.00-180.00   52
 25  ω     42.00  68.00   0.50   10.00    --  113.25 -61.00-150.00   52
 26  ω     97.00 177.00   0.50   10.00    --  113.25  61.00-120.00  160
 27  ω     91.00 177.00   0.50   10.00    --  113.25  77.00  60.00  172
 28  ω     42.00 102.00   0.50   10.00    --  113.25 -77.00-120.00  120
 29  ω     91.00 177.00   0.50   10.00    --  113.25  77.00 -30.00  172
 30  ω     91.00 177.00   0.50   10.00    --  113.25  77.00-150.00  172
 31  ω    101.00 177.00   0.50   10.00    --  113.25  31.00  16.78  152
 32  ω     42.00 102.00   0.50   10.00    --  113.25 -77.00 -60.00  120
 33  ω     42.00  68.00   0.50   10.00    --  113.25 -61.00 150.00   52
 34  ω     42.00 106.00   0.50   10.00    --  113.25 -94.00 -60.00  128
 35  ω     42.00 106.00   0.50   10.00    --  113.25 -94.00-150.00  128
 36  ω     97.00 177.00   0.50   10.00    --  113.25  61.00 120.00  160
 37  ω     42.00 102.00   0.50   10.00    --  113.25 -77.00  30.00  120
 38  ω     42.00 102.00   0.50   10.00    --  113.25 -77.00 120.00  120
 39  ω     42.00 106.00   0.50   10.00    --  113.25 -94.00-120.00  128
 40  ω    100.00 177.00   0.50   10.00    --  113.25  52.00  77.85  154
 41  ω    101.00 177.00   0.50   10.00    --  113.25  45.00  30.00  152
 42  ω     42.00  68.00   0.50   10.00    --  113.25 -61.00  60.00   52
 43  ω     74.50 119.00   0.50    1.30    --   47.42  77.00 -90.00   89
 44  ω     25.00  75.00   0.50    1.30    --   47.42  77.00  30.00  100
 45  ω     74.50 119.00   0.50    1.30    --   47.42  77.00-180.00   89
 46  ω     25.00  45.00   0.50    1.30    --   47.42  77.00  90.00   40
 47  ω     25.00  70.00   0.50    1.30    --   47.42  77.00-120.00   90
 48  ω     89.50 119.00   0.50    1.30    --   47.42  77.00 120.00   59
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1019P)²+0.5535P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0083(11)
_refine_ls_number_reflns         3369
_refine_ls_number_parameters     309
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.065
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1812
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C12, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C15A) \\sim Ueq, Uanis(N5A) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C7A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C8A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C16A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H10A)=Sof(H14D)=Sof(H14E)=Sof(H12C)=Sof(H12D)=Sof(H12E)=Sof(C13A)=
 Sof(H13A)=Sof(N5A)=Sof(O1A)=Sof(C15A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C16A)=Sof(H16C)=
 Sof(H16D)=1-FVAR(1)
 Sof(N5)=Sof(O1)=Sof(H10)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C13)=Sof(H13)=Sof(C15)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(H12A)=Sof(H12B)=Sof(C9)=Sof(C16)=Sof(H16A)=
 Sof(H16B)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C11)=Sof(H11A)=Sof(H11B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C10(H10A), C13(H13), C13A(H13A)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14D,H14E), C12(H12A,H12B), C16(H16A,H16B), C8(H8A,H8B),
 C11(H11A,H11B), C8A(H8AA,H8AB), C11A(H11C,H11D), C7A(H7AA,H7AB), C16A(H16C,
 H16D)
5.c Me refined with riding coordinates:
 C12(H12C,H12D,H12E)
5.d Aromatic/amide H refined with riding coordinates:
 C5(H5A), C2(H2), C1(H1A)
5.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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
N3 N 0.4507(2) 0.91175(10) 0.62619(14) 0.0546(4) Uani 1 1 d . . . . .
N2 N 0.2003(2) 0.97496(10) 0.57487(15) 0.0573(4) Uani 1 1 d . . . . .
N4 N 0.6034(2) 0.85267(10) 0.48621(14) 0.0552(4) Uani 1 1 d . . . . .
N1 N 0.1181(2) 0.97277(10) 0.36058(16) 0.0575(4) Uani 1 1 d . . . . .
N5 N 0.9302(3) 0.66113(14) 0.3734(2) 0.0524(5) Uani 0.878(4) 1 d . . P A 1
O1 O 1.0449(3) 0.65685(19) 0.5668(2) 0.0753(8) Uani 0.878(4) 1 d . . P A 1
C3 C 0.3524(2) 0.91469(11) 0.41567(17) 0.0511(4) Uani 1 1 d . . . . .
C6 C 0.4706(2) 0.89206(10) 0.50774(16) 0.0505(4) Uani 1 1 d . . . . .
C4 C 0.2221(2) 0.95499(11) 0.45769(17) 0.0532(5) Uani 1 1 d . . . . .
C10 C 0.6312(2) 0.81478(11) 0.37051(17) 0.0534(5) Uani 1 1 d . . . . .
H10 H 0.618318 0.849429 0.29996 0.064 Uiso 0.878(4) 1 calc R U P A 1
H10A H 0.529729 0.804933 0.318245 0.064 Uiso 0.122(4) 1 calc R U P A 2
C5 C 0.3210(3) 0.95204(12) 0.65073(18) 0.0575(5) Uani 1 1 d . . . . .
H5A H 0.314442 0.966194 0.734025 0.069 Uiso 1 1 calc R U . . .
C2 C 0.3222(3) 0.90888(12) 0.28481(18) 0.0570(5) Uani 1 1 d . . . . .
H2 H 0.389152 0.884888 0.229136 0.068 Uiso 1 1 calc R U . . .
C1 C 0.1805(3) 0.94411(12) 0.25627(19) 0.0591(5) Uani 1 1 d . . . . .
H1A H 0.131015 0.948466 0.175849 0.071 Uiso 1 1 calc R U . . .
N6 N 1.3209(3) 0.51181(15) 0.5757(2) 0.0873(7) Uani 1 1 d . . . . .
C7 C 0.7350(3) 0.83829(17) 0.5791(2) 0.0546(6) Uani 0.878(4) 1 d . . P A 1
H7A H 0.710875 0.794966 0.628952 0.066 Uiso 0.878(4) 1 calc R U P A 1
H7B H 0.753978 0.880702 0.63406 0.066 Uiso 0.878(4) 1 calc R U P A 1
C17 C 1.2560(3) 0.54689(14) 0.50257(19) 0.0646(6) Uani 1 1 d . . . . .
C13 C 0.7881(3) 0.70430(15) 0.4014(2) 0.0517(6) Uani 0.878(4) 1 d . . P A 1
H13 H 0.764632 0.695052 0.488922 0.062 Uiso 0.878(4) 1 calc R U P A 1
C15 C 1.0419(5) 0.6401(3) 0.4585(4) 0.0578(10) Uani 0.878(4) 1 d . . P A 1
C14 C 0.9016(3) 0.80377(14) 0.2713(2) 0.0660(6) Uani 1 1 d . . . . .
H14A H 0.851022 0.777616 0.200748 0.099 Uiso 0.878(4) 1 calc R U P A 1
H14B H 1.01526 0.788073 0.284864 0.099 Uiso 0.878(4) 1 calc R U P A 1
H14C H 0.898315 0.856255 0.254997 0.099 Uiso 0.878(4) 1 calc R U P A 1
H14D H 0.88074 0.78131 0.189454 0.079 Uiso 0.122(4) 1 calc R U P A 2
H14E H 1.005847 0.83096 0.273033 0.079 Uiso 0.122(4) 1 calc R U P A 2
C12 C 0.6354(3) 0.68465(13) 0.3218(2) 0.0654(6) Uani 1 1 d . U . . .
H12A H 0.589121 0.637508 0.346905 0.079 Uiso 0.878(4) 1 calc R U P A 1
H12B H 0.658593 0.682413 0.233861 0.079 Uiso 0.878(4) 1 calc R U P A 1
H12C H 0.52427 0.676879 0.347626 0.098 Uiso 0.122(4) 1 calc R U P A 2
H12D H 0.63079 0.706263 0.239603 0.098 Uiso 0.122(4) 1 calc R U P A 2
H12E H 0.69274 0.63789 0.320295 0.098 Uiso 0.122(4) 1 calc R U P A 2
C9 C 0.8089(3) 0.78729(13) 0.38489(19) 0.0522(6) Uani 0.878(4) 1 d . . P A 1
C16 C 1.1826(4) 0.59521(19) 0.4071(3) 0.0572(7) Uani 0.878(4) 1 d . . P A 1
H16A H 1.139963 0.565726 0.336467 0.069 Uiso 0.878(4) 1 calc R U P A 1
H16B H 1.26678 0.628593 0.377929 0.069 Uiso 0.878(4) 1 calc R U P A 1
C8 C 0.8793(3) 0.82497(14) 0.5018(2) 0.0580(6) Uani 0.878(4) 1 d . . P A 1
H8A H 0.960703 0.793363 0.545945 0.07 Uiso 0.878(4) 1 calc R U P A 1
H8B H 0.932232 0.871535 0.481551 0.07 Uiso 0.878(4) 1 calc R U P A 1
C11 C 0.5203(3) 0.74841(15) 0.3480(3) 0.0630(7) Uani 0.878(4) 1 d . . P A 1
H11A H 0.442269 0.756963 0.277006 0.076 Uiso 0.878(4) 1 calc R U P A 1
H11B H 0.458091 0.738022 0.421138 0.076 Uiso 0.878(4) 1 calc R U P A 1
C13A C 0.900(2) 0.7483(8) 0.3721(13) 0.050(4) Uani 0.122(4) 1 d . . P A 2
H13A H 0.961302 0.773205 0.441897 0.06 Uiso 0.122(4) 1 calc R U P A 2
N5A N 0.996(2) 0.6842(9) 0.3538(15) 0.050(4) Uani 0.122(4) 1 d . U P A 2
O1A O 1.119(4) 0.6763(14) 0.542(2) 0.103(7) Uani 0.122(4) 1 d . U P A 2
C15A C 1.086(4) 0.650(2) 0.444(3) 0.055(7) Uani 0.122(4) 1 d . U P A 2
C8A C 0.728(4) 0.7365(18) 0.560(2) 0.109(9) Uani 0.122(4) 1 d . U P A 2
H8AA H 0.644029 0.702048 0.585639 0.131 Uiso 0.122(4) 1 calc R U P A 2
H8AB H 0.83566 0.721525 0.59795 0.131 Uiso 0.122(4) 1 calc R U P A 2
C9A C 0.733(3) 0.7396(11) 0.4184(17) 0.060(4) Uani 0.122(4) 1 d . U P A 2
C11A C 0.761(2) 0.8519(9) 0.3059(15) 0.054(4) Uani 0.122(4) 1 d . . P A 2
H11C H 0.805269 0.891849 0.358649 0.065 Uiso 0.122(4) 1 calc R U P A 2
H11D H 0.711354 0.874159 0.230117 0.065 Uiso 0.122(4) 1 calc R U P A 2
C7A C 0.692(3) 0.8055(15) 0.592(2) 0.071(6) Uani 0.122(4) 1 d . U P A 2
H7AA H 0.794298 0.830475 0.619446 0.085 Uiso 0.122(4) 1 calc R U P A 2
H7AB H 0.62129 0.80378 0.662141 0.085 Uiso 0.122(4) 1 calc R U P A 2
H5 H 0.947(3) 0.6497(14) 0.300(3) 0.062(7) Uiso 1 1 d . . . . .
C16A C 1.137(3) 0.5666(13) 0.406(2) 0.058(5) Uani 0.122(4) 1 d . U P A 2
H16C H 1.041928 0.533636 0.403948 0.069 Uiso 0.122(4) 1 calc R U P A 2
H16D H 1.185781 0.565612 0.32465 0.069 Uiso 0.122(4) 1 calc R U P A 2
H1 H 0.026(4) 0.9967(15) 0.370(3) 0.075(8) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C6 1.361(2) . ?
N3 C5 1.336(3) . ?
N2 C4 1.352(3) . ?
N2 C5 1.324(3) . ?
N4 C6 1.341(3) . ?
N4 C10 1.471(2) . ?
N4 C7 1.464(3) . ?
N4 C7A 1.58(2) . ?
N1 C4 1.363(3) . ?
N1 C1 1.379(3) . ?
N1 H1 0.89(3) . ?
N5 C13 1.457(4) . ?
N5 C15 1.326(5) . ?
N5 H5 0.85(3) . ?
O1 C15 1.221(5) . ?
C3 C6 1.420(3) . ?
C3 C4 1.399(3) . ?
C3 C2 1.440(3) . ?
C10 H10 1 . ?
C10 H10A 1 . ?
C10 C9 1.544(3) . ?
C10 C11 1.533(3) . ?
C10 C9A 1.68(2) . ?
C10 C11A 1.476(16) . ?
C5 H5A 0.95 . ?
C2 H2 0.95 . ?
C2 C1 1.353(3) . ?
C1 H1A 0.95 . ?
N6 C17 1.135(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C7 C8 1.512(4) . ?
C17 C16 1.472(4) . ?
C17 C16A 1.44(2) . ?
C13 H13 1 . ?
C13 C12 1.529(3) . ?
C13 C9 1.545(4) . ?
C15 C16 1.550(5) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C14 H14D 0.99 . ?
C14 H14E 0.99 . ?
C14 C9 1.521(3) . ?
C14 C13A 1.500(15) . ?
C14 C11A 1.518(17) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C12 H12C 0.98 . ?
C12 H12D 0.98 . ?
C12 H12E 0.98 . ?
C12 C11 1.541(3) . ?
C12 C9A 1.635(19) . ?
C9 C8 1.536(3) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C13A H13A 1 . ?
C13A N5A 1.436(19) . ?
C13A C9A 1.50(3) . ?
N5A C15A 1.35(4) . ?
N5A H5 0.94(3) . ?
O1A C15A 1.19(4) . ?
C15A C16A 1.65(4) . ?
C8A H8AA 0.99 . ?
C8A H8AB 0.99 . ?
C8A C9A 1.55(3) . ?
C8A C7A 1.35(4) . ?
C11A H11C 0.99 . ?
C11A H11D 0.99 . ?
C7A H7AA 0.99 . ?
C7A H7AB 0.99 . ?
C16A H16C 0.99 . ?
C16A H16D 0.99 . ?

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
C5 N3 C6 118.46(17) . . ?
C5 N2 C4 111.80(18) . . ?
C6 N4 C10 124.91(16) . . ?
C6 N4 C7 123.51(17) . . ?
C6 N4 C7A 120.9(9) . . ?
C10 N4 C7A 106.1(9) . . ?
C7 N4 C10 111.46(17) . . ?
C4 N1 C1 107.77(18) . . ?
C4 N1 H1 121.8(19) . . ?
C1 N1 H1 130.4(19) . . ?
C13 N5 H5 120.4(17) . . ?
C15 N5 C13 122.8(3) . . ?
C15 N5 H5 116.7(18) . . ?
C6 C3 C2 138.88(19) . . ?
C4 C3 C6 115.33(17) . . ?
C4 C3 C2 105.79(17) . . ?
N3 C6 C3 118.76(18) . . ?
N4 C6 N3 116.85(17) . . ?
N4 C6 C3 124.39(17) . . ?
N2 C4 N1 124.08(19) . . ?
N2 C4 C3 126.69(18) . . ?
N1 C4 C3 109.21(17) . . ?
N4 C10 H10 110.2 . . ?
N4 C10 H10A 114.3 . . ?
N4 C10 C9 104.96(16) . . ?
N4 C10 C11 113.24(18) . . ?
N4 C10 C9A 102.7(7) . . ?
N4 C10 C11A 110.0(7) . . ?
C9 C10 H10 110.2 . . ?
C11 C10 H10 110.2 . . ?
C11 C10 C9 107.83(18) . . ?
C9A C10 H10A 114.3 . . ?
C11A C10 H10A 114.3 . . ?
C11A C10 C9A 99.8(9) . . ?
N3 C5 H5A 115.6 . . ?
N2 C5 N3 128.89(19) . . ?
N2 C5 H5A 115.6 . . ?
C3 C2 H2 126.5 . . ?
C1 C2 C3 106.93(19) . . ?
C1 C2 H2 126.5 . . ?
N1 C1 H1A 124.9 . . ?
C2 C1 N1 110.29(18) . . ?
C2 C1 H1A 124.9 . . ?
N4 C7 H7A 111.3 . . ?
N4 C7 H7B 111.3 . . ?
N4 C7 C8 102.33(19) . . ?
H7A C7 H7B 109.2 . . ?
C8 C7 H7A 111.3 . . ?
C8 C7 H7B 111.3 . . ?
N6 C17 C16 176.0(3) . . ?
N6 C17 C16A 158.2(11) . . ?
N5 C13 H13 107.9 . . ?
N5 C13 C12 113.2(2) . . ?
N5 C13 C9 114.7(2) . . ?
C12 C13 H13 107.9 . . ?
C12 C13 C9 105.0(2) . . ?
C9 C13 H13 107.9 . . ?
N5 C15 C16 113.7(3) . . ?
O1 C15 N5 125.6(4) . . ?
O1 C15 C16 120.6(4) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14D C14 H14E 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
C13A C14 H14D 111.8 . . ?
C13A C14 H14E 111.8 . . ?
C13A C14 C11A 100.1(8) . . ?
C11A C14 H14D 111.8 . . ?
C11A C14 H14E 111.8 . . ?
C13 C12 H12A 111.4 . . ?
C13 C12 H12B 111.4 . . ?
C13 C12 C11 101.98(19) . . ?
H12A C12 H12B 109.2 . . ?
H12C C12 H12D 109.5 . . ?
H12C C12 H12E 109.5 . . ?
H12D C12 H12E 109.5 . . ?
C11 C12 H12A 111.4 . . ?
C11 C12 H12B 111.4 . . ?
C9A C12 H12C 109.5 . . ?
C9A C12 H12D 109.5 . . ?
C9A C12 H12E 109.5 . . ?
C10 C9 C13 102.97(18) . . ?
C14 C9 C10 111.40(18) . . ?
C14 C9 C13 110.8(2) . . ?
C14 C9 C8 113.94(19) . . ?
C8 C9 C10 104.29(18) . . ?
C8 C9 C13 112.73(19) . . ?
C17 C16 C15 110.4(3) . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C7 C8 C9 105.45(19) . . ?
C7 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C10 C11 C12 105.58(19) . . ?
C10 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
C14 C13A H13A 102.9 . . ?
N5A C13A C14 115.3(13) . . ?
N5A C13A H13A 102.9 . . ?
N5A C13A C9A 118.7(17) . . ?
C9A C13A C14 111.4(13) . . ?
C9A C13A H13A 102.9 . . ?
C13A N5A H5 115(2) . . ?
C15A N5A C13A 124(2) . . ?
C15A N5A H5 110(3) . . ?
N5A C15A C16A 113(2) . . ?
O1A C15A N5A 124(3) . . ?
O1A C15A C16A 124(3) . . ?
H8AA C8A H8AB 109 . . ?
C9A C8A H8AA 111 . . ?
C9A C8A H8AB 111 . . ?
C7A C8A H8AA 111 . . ?
C7A C8A H8AB 111 . . ?
C7A C8A C9A 104(2) . . ?
C12 C9A C10 95.2(11) . . ?
C13A C9A C10 104.8(12) . . ?
C13A C9A C12 105.8(13) . . ?
C13A C9A C8A 114(2) . . ?
C8A C9A C10 107.6(16) . . ?
C8A C9A C12 125.8(18) . . ?
C10 C11A C14 115.5(10) . . ?
C10 C11A H11C 108.4 . . ?
C10 C11A H11D 108.4 . . ?
C14 C11A H11C 108.4 . . ?
C14 C11A H11D 108.4 . . ?
H11C C11A H11D 107.5 . . ?
N4 C7A H7AA 108.5 . . ?
N4 C7A H7AB 108.5 . . ?
C8A C7A N4 115(2) . . ?
C8A C7A H7AA 108.5 . . ?
C8A C7A H7AB 108.5 . . ?
H7AA C7A H7AB 107.5 . . ?
C17 C16A C15A 102.7(18) . . ?
C17 C16A H16C 111.2 . . ?
C17 C16A H16D 111.2 . . ?
C15A C16A H16C 111.2 . . ?
C15A C16A H16D 111.2 . . ?
H16C C16A H16D 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C10 C9 C13 107.64(18) . . . . ?
N4 C10 C9 C14 -133.60(19) . . . . ?
N4 C10 C9 C8 -10.3(2) . . . . ?
N4 C10 C11 C12 -127.5(2) . . . . ?
N4 C10 C9A C12 138.9(7) . . . . ?
N4 C10 C9A C13A -113.2(10) . . . . ?
N4 C10 C9A C8A 8.8(19) . . . . ?
N4 C10 C11A C14 125.9(9) . . . . ?
N4 C7 C8 C9 -34.0(3) . . . . ?
N5 C13 C12 C11 -167.2(2) . . . . ?
N5 C13 C9 C10 158.93(18) . . . . ?
N5 C13 C9 C14 39.7(3) . . . . ?
N5 C13 C9 C8 -89.3(2) . . . . ?
N5 C15 C16 C17 -154.0(3) . . . . ?
O1 C15 C16 C17 30.1(6) . . . . ?
C3 C2 C1 N1 0.5(2) . . . . ?
C6 N3 C5 N2 2.5(3) . . . . ?
C6 N4 C10 C9 172.08(19) . . . . ?
C6 N4 C10 C11 -70.6(3) . . . . ?
C6 N4 C10 C9A -145.2(7) . . . . ?
C6 N4 C10 C11A 109.3(7) . . . . ?
C6 N4 C7 C8 -154.9(2) . . . . ?
C6 N4 C7A C8A 133(2) . . . . ?
C6 C3 C4 N2 1.2(3) . . . . ?
C6 C3 C4 N1 -179.73(17) . . . . ?
C6 C3 C2 C1 179.5(2) . . . . ?
C4 N2 C5 N3 -2.4(3) . . . . ?
C4 N1 C1 C2 -0.4(2) . . . . ?
C4 C3 C6 N3 -1.1(3) . . . . ?
C4 C3 C6 N4 179.53(19) . . . . ?
C4 C3 C2 C1 -0.4(2) . . . . ?
C10 N4 C6 N3 167.91(18) . . . . ?
C10 N4 C6 C3 -12.8(3) . . . . ?
C10 N4 C7 C8 28.7(3) . . . . ?
C10 N4 C7A C8A -17(3) . . . . ?
C10 C9 C8 C7 27.6(2) . . . . ?
C5 N3 C6 N4 178.94(18) . . . . ?
C5 N3 C6 C3 -0.4(3) . . . . ?
C5 N2 C4 N1 -178.51(19) . . . . ?
C5 N2 C4 C3 0.5(3) . . . . ?
C2 C3 C6 N3 178.9(2) . . . . ?
C2 C3 C6 N4 -0.4(4) . . . . ?
C2 C3 C4 N2 -178.9(2) . . . . ?
C2 C3 C4 N1 0.2(2) . . . . ?
C1 N1 C4 N2 179.2(2) . . . . ?
C1 N1 C4 C3 0.1(2) . . . . ?
N6 C17 C16A C15A 137(2) . . . . ?
C7 N4 C6 N3 -8.0(3) . . . . ?
C7 N4 C6 C3 171.4(2) . . . . ?
C7 N4 C10 C9 -11.6(2) . . . . ?
C7 N4 C10 C11 105.8(2) . . . . ?
C13 N5 C15 O1 -3.9(7) . . . . ?
C13 N5 C15 C16 -179.6(3) . . . . ?
C13 C12 C11 C10 32.4(2) . . . . ?
C13 C9 C8 C7 -83.3(3) . . . . ?
C15 N5 C13 C12 -144.6(3) . . . . ?
C15 N5 C13 C9 94.9(4) . . . . ?
C14 C9 C8 C7 149.3(2) . . . . ?
C14 C13A N5A C15A 141(2) . . . . ?
C14 C13A C9A C10 -18.3(15) . . . . ?
C14 C13A C9A C12 81.6(14) . . . . ?
C14 C13A C9A C8A -135.8(18) . . . . ?
C12 C13 C9 C10 34.0(2) . . . . ?
C12 C13 C9 C14 -85.2(2) . . . . ?
C12 C13 C9 C8 145.82(19) . . . . ?
C9 C10 C11 C12 -11.8(2) . . . . ?
C9 C13 C12 C11 -41.4(2) . . . . ?
C11 C10 C9 C13 -13.4(2) . . . . ?
C11 C10 C9 C14 105.4(2) . . . . ?
C11 C10 C9 C8 -131.26(19) . . . . ?
C13A C14 C11A C10 -29.4(13) . . . . ?
C13A N5A C15A O1A -14(5) . . . . ?
C13A N5A C15A C16A 163(2) . . . . ?
N5A C13A C9A C10 -155.8(12) . . . . ?
N5A C13A C9A C12 -55.9(18) . . . . ?
N5A C13A C9A C8A 87(2) . . . . ?
N5A C15A C16A C17 169(2) . . . . ?
O1A C15A C16A C17 -14(4) . . . . ?
C9A C10 C11A C14 18.5(13) . . . . ?
C9A C13A N5A C15A -83(3) . . . . ?
C9A C8A C7A N4 22(3) . . . . ?
C11A C10 C9A C12 -107.8(10) . . . . ?
C11A C10 C9A C13A 0.1(13) . . . . ?
C11A C10 C9A C8A 122.1(19) . . . . ?
C11A C14 C13A N5A 167.0(14) . . . . ?
C11A C14 C13A C9A 27.9(14) . . . . ?
C7A N4 C6 N3 23.6(13) . . . . ?
C7A N4 C6 C3 -157.1(13) . . . . ?
C7A N4 C10 C9A 3.4(13) . . . . ?
C7A N4 C10 C11A -102.1(13) . . . . ?
C7A C8A C9A C10 -19(3) . . . . ?
C7A C8A C9A C12 -129(2) . . . . ?
C7A C8A C9A C13A 97(3) . . . . ?

#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   SHELX HKL FILE                                           #
#----------------------------------------------------------------------------#


# END of CIF
####################################################################### 
# 
# 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_22JLR017_KM-113-02-f4
_database_code_depnum_ccdc_archive 'CCDC 2482168'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;

_audit_creation_date             2022-11-02T15:03:52-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C30 H41 N3'
_chemical_formula_sum            'C30 H41 N3'
_chemical_formula_weight         443.66

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.39323(11)
_cell_length_b                   18.53440(16)
_cell_length_c                   6.83259(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.9405(10)
_cell_angle_gamma                90
_cell_volume                     1315.42(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.01(10)
_cell_measurement_reflns_used    26342
_cell_measurement_theta_min      4.238
_cell_measurement_theta_max      77.751

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.12
_exptl_crystal_F_000             484
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 1 0.0691
-1 1 -1 0.0732
-1 1 0 0.073
1 -1 0 0.0654
0 -1 -1 0.1287
1 0 1 0.077
-1 1 1 0.1149
1 1 1 0.0827
-1 -1 -1 0.0894
-1 0 0 0.0612
1 0 0 0.0426
-1 -1 0 0.0908
1 1 0 0.0648
-1 0 1 0.0988
1 0 -1 0.1232
0 -1 0 0.1176
0 -1 1 0.0758
0 1 -1 0.1071
2 -11 -1 0.0943
-2 11 0 0.095
-2 10 -2 0.0996


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.69593
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.951

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1158209
_diffrn_orient_matrix_ub_12      0.0452181
_diffrn_orient_matrix_ub_13      -0.0757363
_diffrn_orient_matrix_ub_21      -0.0911249
_diffrn_orient_matrix_ub_22      -0.0627434
_diffrn_orient_matrix_ub_23      0.0463857
_diffrn_orient_matrix_ub_31      -0.016508
_diffrn_orient_matrix_ub_32      0.0304865
_diffrn_orient_matrix_ub_33      0.2073791
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_number            49699
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.256
_diffrn_reflns_theta_max         72.802
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             2627
_reflns_number_gt                2468
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.3339P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     306
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1357
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.024

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
N1 N 0.8462(13) 0.1302(12) 0.149(2) 0.0612(12) Uani 0.5078(19) 1 d . U P A -1
N2 N 0.5 0 0 0.0658(5) Uani 1 2 d S . P . .
H2A H 0.432(7) 0.032(4) 0.011(11) 0.079 Uiso 0.25 1 d . U P B -2
H2B H 0.488(7) -0.005(4) -0.138(11) 0.079 Uiso 0.25 1 d . U P C -1
C10 C 0.6566(12) 0.0998(6) -0.0504(11) 0.061(2) Uani 0.5078(19) 1 d . . P A -1
C2 C 1.0494(13) 0.1066(8) 0.461(2) 0.084(3) Uani 0.51(2) 1 d . U P A -1
H2 H 0.967017 0.085583 0.476102 0.101 Uiso 0.51(2) 1 calc R U P A -1
C11 C 0.5400(3) 0.06593(14) 0.0560(4) 0.0563(7) Uani 0.5078(19) 1 d . . P A -1
H11 H 0.465501 0.098958 0.028448 0.068 Uiso 0.5078(19) 1 calc R U P A -1
C1 C 1.0527(9) 0.1624(5) 0.3204(13) 0.0664(14) Uani 0.51(2) 1 d . U P A -1
C3 C 1.1440(11) 0.0783(7) 0.5762(16) 0.0800(18) Uani 0.51(2) 1 d . U P A -1
H3 H 1.13228 0.03491 0.647356 0.096 Uiso 0.51(2) 1 calc R U P A -1
C6 C 1.1785(9) 0.1907(4) 0.3257(15) 0.0769(15) Uani 0.51(2) 1 d . U P A -1
H6 H 1.198523 0.224932 0.227909 0.092 Uiso 0.51(2) 1 calc R U P A -1
C4 C 1.2574(9) 0.1151(4) 0.5856(13) 0.0815(17) Uani 0.51(2) 1 d . U P A -1
H4 H 1.323593 0.101269 0.677222 0.098 Uiso 0.51(2) 1 calc R U P A -1
C9A C 0.6540(3) 0.1137(2) 0.2249(5) 0.0687(10) Uani 0.4922(19) 1 d . . P A -2
H9AA H 0.657794 0.064978 0.28432 0.082 Uiso 0.4922(19) 1 calc R U P A -2
H9AB H 0.578958 0.13984 0.275485 0.082 Uiso 0.4922(19) 1 calc R U P A -2
C13A C 0.8212(4) 0.04975(18) -0.1675(5) 0.0638(8) Uani 0.4922(19) 1 d . . P A
-2
H13A H 0.911432 0.034916 -0.139295 0.077 Uiso 0.4922(19) 1 calc R U P A -2
H13B H 0.808121 0.05671 -0.310436 0.077 Uiso 0.4922(19) 1 calc R U P A -2
C12A C 0.7276(3) -0.00573(16) -0.0912(4) 0.0562(7) Uani 0.4922(19) 1 d . . P A
-2
H12A H 0.718518 -0.047493 -0.180953 0.067 Uiso 0.4922(19) 1 calc R U P A -2
H12B H 0.754797 -0.023011 0.040916 0.067 Uiso 0.4922(19) 1 calc R U P A -2
C12 C 0.5742(3) 0.07455(17) 0.2719(4) 0.0678(9) Uani 0.5078(19) 1 d . . P A -1
H12C H 0.638807 0.038427 0.317 0.081 Uiso 0.5078(19) 1 calc R U P A -1
H12D H 0.497079 0.07061 0.352438 0.081 Uiso 0.5078(19) 1 calc R U P A -1
C5 C 1.2757(7) 0.1728(3) 0.4610(12) 0.0779(17) Uani 0.51(2) 1 d . U P A -1
H5 H 1.353512 0.19976 0.468144 0.093 Uiso 0.51(2) 1 calc R U P A -1
C14 C 0.7131(3) 0.15391(16) 0.1014(5) 0.0666(8) Uani 0.5078(19) 1 d . U P A -1
H14 H 0.712848 0.203803 0.045673 0.08 Uiso 0.5078(19) 1 calc R U P A -1
C9 C 0.7693(3) 0.0449(2) -0.0707(5) 0.0679(9) Uani 0.5078(19) 1 d . . P A -1
H9A H 0.761143 0.003918 0.021087 0.082 Uiso 0.5078(19) 1 calc R U P A -1
H9B H 0.772702 0.026051 -0.206059 0.082 Uiso 0.5078(19) 1 calc R U P A -1
C8 C 0.8867(3) 0.09040(19) -0.0183(5) 0.0722(9) Uani 0.5078(19) 1 d . U P A -1
H8A H 0.962348 0.059807 0.015206 0.087 Uiso 0.5078(19) 1 calc R U P A -1
H8B H 0.908014 0.123086 -0.127146 0.087 Uiso 0.5078(19) 1 calc R U P A -1
C13 C 0.6295(4) 0.1505(2) 0.2778(7) 0.0829(12) Uani 0.5078(19) 1 d . . P A -1
H13C H 0.560045 0.187024 0.268312 0.099 Uiso 0.5078(19) 1 calc R U P A -1
H13D H 0.681199 0.158645 0.400127 0.099 Uiso 0.5078(19) 1 calc R U P A -1
C7 C 0.9290(4) 0.18806(18) 0.2161(6) 0.0744(9) Uani 0.5078(19) 1 d . U P A -1
H7A H 0.881084 0.21897 0.306727 0.089 Uiso 0.5078(19) 1 calc R U P A -1
H7B H 0.951635 0.218043 0.102433 0.089 Uiso 0.5078(19) 1 calc R U P A -1
C8A C 0.7777(3) 0.15493(19) 0.2684(6) 0.0739(9) Uani 0.4922(19) 1 d . U P A -2
H8AA H 0.767049 0.20717 0.242373 0.089 Uiso 0.4922(19) 1 calc R U P A -2
H8AB H 0.809261 0.147745 0.405347 0.089 Uiso 0.4922(19) 1 calc R U P A -2
C21A C 0.9869(4) 0.1579(2) 0.1156(6) 0.0730(9) Uani 0.4922(19) 1 d . U P A -2
H21A H 0.972957 0.210631 0.104581 0.088 Uiso 0.4922(19) 1 calc R U P A -2
H21B H 1.027599 0.14148 -0.005528 0.088 Uiso 0.4922(19) 1 calc R U P A -2
C11A C 0.6039(3) 0.03759(14) -0.0859(4) 0.0497(7) Uani 0.4922(19) 1 d . . P A
-2
H11A H 0.576701 0.047657 -0.225029 0.06 Uiso 0.4922(19) 1 calc R U P A -2
C14A C 0.7889(3) 0.11784(16) -0.0569(5) 0.0609(8) Uani 0.4922(19) 1 d . U P A
-2
H14A H 0.801372 0.162098 -0.137759 0.073 Uiso 0.4922(19) 1 calc R U P A -2
C15A C 0.5609(4) 0.17225(18) -0.0828(7) 0.0873(13) Uani 0.4922(19) 1 d . . P A
-2
H15A H 0.47151 0.165713 -0.044927 0.131 Uiso 0.4922(19) 1 calc R U P A -2
H15B H 0.564602 0.172163 -0.225939 0.131 Uiso 0.4922(19) 1 calc R U P A -2
H15C H 0.593532 0.218362 -0.031527 0.131 Uiso 0.4922(19) 1 calc R U P A -2
C15 C 0.6172(4) 0.1319(3) -0.2420(6) 0.0976(15) Uani 0.5078(19) 1 d . . P A -1
H15D H 0.580639 0.094331 -0.327993 0.146 Uiso 0.5078(19) 1 calc R U P A -1
H15E H 0.69252 0.153243 -0.302444 0.146 Uiso 0.5078(19) 1 calc R U P A -1
H15F H 0.552535 0.16948 -0.222305 0.146 Uiso 0.5078(19) 1 calc R U P A -1
C1A C 1.0767(9) 0.1430(6) 0.2881(15) 0.0689(16) Uani 0.49(2) 1 d . U P A -2
C6A C 1.1769(12) 0.1879(7) 0.273(2) 0.123(4) Uani 0.49(2) 1 d . U P A -2
H6A H 1.175533 0.229247 0.19021 0.148 Uiso 0.49(2) 1 calc R U P A -2
C2A C 1.0551(12) 0.0900(8) 0.4188(19) 0.0722(18) Uani 0.49(2) 1 d . U P A -2
H2AA H 0.98007 0.060761 0.419291 0.087 Uiso 0.49(2) 1 calc R U P A -2
C3A C 1.1602(14) 0.0844(9) 0.555(2) 0.113(3) Uani 0.49(2) 1 d . U P A -2
H3A H 1.152307 0.053432 0.664477 0.135 Uiso 0.49(2) 1 calc R U P A -2
C4A C 1.2703(12) 0.1207(9) 0.536(3) 0.153(5) Uani 0.49(2) 1 d . U P A -2
H4A H 1.340469 0.11311 0.626054 0.183 Uiso 0.49(2) 1 calc R U P A -2
C5A C 1.2810(9) 0.1682(7) 0.387(3) 0.158(5) Uani 0.49(2) 1 d . U P A -2
H5A H 1.362872 0.188337 0.361978 0.189 Uiso 0.49(2) 1 calc R U P A -2
C10A C 0.6457(12) 0.1090(6) 0.0036(11) 0.0527(16) Uani 0.4922(19) 1 d . . P A
-2
N1A N 0.8611(12) 0.1217(11) 0.132(2) 0.0585(16) Uani 0.4922(19) 1 d . U P A -2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C14 1.477(14) . ?
N1 C8 1.435(8) . ?
N1 C7 1.441(19) . ?
N2 H2A 0.92(7) . ?
N2 H2B 0.95(8) . ?
N2 C11 1.342(3) . ?
N2 C11A 1.428(3) . ?
C10 C11 1.565(12) . ?
C10 C14 1.544(11) . ?
C10 C9 1.563(12) . ?
C10 C15 1.483(11) . ?
C2 H2 0.95 . ?
C2 C1 1.411(16) . ?
C2 C3 1.346(18) . ?
C11 H11 1 . ?
C11 C12 1.514(4) . ?
C1 C6 1.407(13) . ?
C1 C7 1.525(10) . ?
C3 H3 0.95 . ?
C3 C4 1.361(10) . ?
C6 H6 0.95 . ?
C6 C5 1.386(10) . ?
C4 H4 0.95 . ?
C4 C5 1.384(9) . ?
C9A H9AA 0.99 . ?
C9A H9AB 0.99 . ?
C9A C8A 1.517(5) . ?
C9A C10A 1.514(8) . ?
C13A H13A 0.99 . ?
C13A H13B 0.99 . ?
C13A C12A 1.520(4) . ?
C13A C14A 1.514(5) . ?
C12A H12A 0.99 . ?
C12A H12B 0.99 . ?
C12A C11A 1.517(4) . ?
C12 H12C 0.99 . ?
C12 H12D 0.99 . ?
C12 C13 1.521(5) . ?
C5 H5 0.95 . ?
C14 H14 1 . ?
C14 C13 1.510(5) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C9 C8 1.516(5) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C13 H13C 0.99 . ?
C13 H13D 0.99 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8A H8AA 0.99 . ?
C8A H8AB 0.99 . ?
C8A N1A 1.435(7) . ?
C21A H21A 0.99 . ?
C21A H21B 0.99 . ?
C21A C1A 1.504(9) . ?
C21A N1A 1.477(19) . ?
C11A H11A 1 . ?
C11A C10A 1.516(11) . ?
C14A H14A 1 . ?
C14A C10A 1.567(12) . ?
C14A N1A 1.470(14) . ?
C15A H15A 0.98 . ?
C15A H15B 0.98 . ?
C15A H15C 0.98 . ?
C15A C10A 1.569(11) . ?
C15 H15D 0.98 . ?
C15 H15E 0.98 . ?
C15 H15F 0.98 . ?
C1A C6A 1.341(15) . ?
C1A C2A 1.351(16) . ?
C6A H6A 0.95 . ?
C6A C5A 1.364(13) . ?
C2A H2AA 0.95 . ?
C2A C3A 1.413(18) . ?
C3A H3A 0.95 . ?
C3A C4A 1.337(14) . ?
C4A H4A 0.95 . ?
C4A C5A 1.352(14) . ?
C5A H5A 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C14 106.0(9) . . ?
C8 N1 C7 116.7(11) . . ?
C7 N1 C14 113.2(12) . . ?
C11 N2 H2B 114(5) . . ?
C11A N2 H2A 109(5) . . ?
C14 C10 C11 103.4(4) . . ?
C14 C10 C9 102.3(8) . . ?
C9 C10 C11 112.0(7) . . ?
C15 C10 C11 112.1(8) . . ?
C15 C10 C14 114.8(8) . . ?
C15 C10 C9 111.6(5) . . ?
C1 C2 H2 114.7 . . ?
C3 C2 H2 114.7 . . ?
C3 C2 C1 130.5(11) . . ?
N2 C11 C10 118.1(4) . . ?
N2 C11 H11 105.9 . . ?
N2 C11 C12 115.7(2) . . ?
C10 C11 H11 105.9 . . ?
C12 C11 C10 104.5(4) . . ?
C12 C11 H11 105.9 . . ?
C2 C1 C7 120.4(8) . . ?
C6 C1 C2 107.4(8) . . ?
C6 C1 C7 131.6(8) . . ?
C2 C3 H3 121.7 . . ?
C2 C3 C4 116.5(9) . . ?
C4 C3 H3 121.7 . . ?
C1 C6 H6 117.1 . . ?
C5 C6 C1 125.7(7) . . ?
C5 C6 H6 117.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(7) . . ?
C5 C4 H4 120.2 . . ?
H9AA C9A H9AB 109 . . ?
C8A C9A H9AA 110.9 . . ?
C8A C9A H9AB 110.9 . . ?
C10A C9A H9AA 110.9 . . ?
C10A C9A H9AB 110.9 . . ?
C10A C9A C8A 104.1(6) . . ?
H13A C13A H13B 109 . . ?
C12A C13A H13A 111 . . ?
C12A C13A H13B 111 . . ?
C14A C13A H13A 111 . . ?
C14A C13A H13B 111 . . ?
C14A C13A C12A 103.7(3) . . ?
C13A C12A H12A 111.4 . . ?
C13A C12A H12B 111.4 . . ?
H12A C12A H12B 109.3 . . ?
C11A C12A C13A 101.7(3) . . ?
C11A C12A H12A 111.4 . . ?
C11A C12A H12B 111.4 . . ?
C11 C12 H12C 111.5 . . ?
C11 C12 H12D 111.5 . . ?
C11 C12 C13 101.5(3) . . ?
H12C C12 H12D 109.3 . . ?
C13 C12 H12C 111.5 . . ?
C13 C12 H12D 111.5 . . ?
C6 C5 H5 120.6 . . ?
C4 C5 C6 118.8(6) . . ?
C4 C5 H5 120.6 . . ?
N1 C14 C10 106.6(7) . . ?
N1 C14 H14 110.4 . . ?
N1 C14 C13 111.8(7) . . ?
C10 C14 H14 110.4 . . ?
C13 C14 C10 107.0(4) . . ?
C13 C14 H14 110.4 . . ?
C10 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C8 C9 C10 102.5(5) . . ?
C8 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
N1 C8 C9 102.6(8) . . ?
N1 C8 H8A 111.2 . . ?
N1 C8 H8B 111.2 . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.2 . . ?
C12 C13 H13C 110.9 . . ?
C12 C13 H13D 110.9 . . ?
C14 C13 C12 104.2(3) . . ?
C14 C13 H13C 110.9 . . ?
C14 C13 H13D 110.9 . . ?
H13C C13 H13D 108.9 . . ?
N1 C7 C1 113.7(8) . . ?
N1 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C1 C7 H7A 108.8 . . ?
C1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9A C8A H8AA 111.7 . . ?
C9A C8A H8AB 111.7 . . ?
H8AA C8A H8AB 109.4 . . ?
N1A C8A C9A 100.6(7) . . ?
N1A C8A H8AA 111.7 . . ?
N1A C8A H8AB 111.7 . . ?
H21A C21A H21B 107.8 . . ?
C1A C21A H21A 109.1 . . ?
C1A C21A H21B 109.1 . . ?
N1A C21A H21A 109.1 . . ?
N1A C21A H21B 109.1 . . ?
N1A C21A C1A 112.6(8) . . ?
N2 C11A C12A 113.9(2) . . ?
N2 C11A H11A 106.8 . . ?
N2 C11A C10A 118.1(4) . . ?
C12A C11A H11A 106.8 . . ?
C10A C11A C12A 103.9(5) . . ?
C10A C11A H11A 106.8 . . ?
C13A C14A H14A 111.9 . . ?
C13A C14A C10A 105.8(4) . . ?
C10A C14A H14A 111.9 . . ?
N1A C14A C13A 111.3(6) . . ?
N1A C14A H14A 111.9 . . ?
N1A C14A C10A 103.6(7) . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C10A C15A H15A 109.5 . . ?
C10A C15A H15B 109.5 . . ?
C10A C15A H15C 109.5 . . ?
C10 C15 H15D 109.5 . . ?
C10 C15 H15E 109.5 . . ?
C10 C15 H15F 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C6A C1A C21A 106.6(9) . . ?
C6A C1A C2A 130.6(12) . . ?
C2A C1A C21A 122.6(8) . . ?
C1A C6A H6A 123.5 . . ?
C1A C6A C5A 113.0(10) . . ?
C5A C6A H6A 123.5 . . ?
C1A C2A H2AA 124.9 . . ?
C1A C2A C3A 110.2(13) . . ?
C3A C2A H2AA 124.9 . . ?
C2A C3A H3A 118.5 . . ?
C4A C3A C2A 122.9(11) . . ?
C4A C3A H3A 118.5 . . ?
C3A C4A H4A 120.2 . . ?
C3A C4A C5A 119.6(9) . . ?
C5A C4A H4A 120.2 . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A C6A 121.5(8) . . ?
C4A C5A H5A 119.3 . . ?
C9A C10A C11A 117.3(7) . . ?
C9A C10A C14A 103.6(7) . . ?
C9A C10A C15A 110.2(5) . . ?
C11A C10A C14A 104.3(5) . . ?
C11A C10A C15A 110.5(7) . . ?
C14A C10A C15A 110.5(7) . . ?
C8A N1A C21A 114.2(10) . . ?
C8A N1A C14A 106.8(8) . . ?
C14A N1A C21A 112.5(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C14 C13 C12 -89.3(9) . . . . ?
N2 C11 C12 C13 173.4(3) . . . . ?
N2 C11A C10A C9A 42.3(9) . . . . ?
N2 C11A C10A C14A 156.1(3) . . . . ?
N2 C11A C10A C15A -85.2(6) . . . . ?
C10 C11 C12 C13 41.8(5) . . . . ?
C10 C14 C13 C12 27.1(6) . . . . ?
C10 C9 C8 N1 43.2(10) . . . . ?
C2 C1 C6 C5 -7.4(11) . . . . ?
C2 C1 C7 N1 -44.8(9) . . . . ?
C2 C3 C4 C5 -8.1(17) . . . . ?
C11 C10 C14 N1 118.6(11) . . . . ?
C11 C10 C14 C13 -1.3(7) . . . . ?
C11 C10 C9 C8 -137.0(6) . . . . ?
C11 C12 C13 C14 -42.6(4) . . . . ?
C1 C2 C3 C4 12(2) . . . . ?
C1 C6 C5 C4 10.2(13) . . . . ?
C3 C2 C1 C6 -4.0(15) . . . . ?
C3 C2 C1 C7 -176.2(15) . . . . ?
C3 C4 C5 C6 -1.5(13) . . . . ?
C6 C1 C7 N1 145.2(10) . . . . ?
C9A C8A N1A C21A 171.1(11) . . . . ?
C9A C8A N1A C14A 46.0(15) . . . . ?
C13A C12A C11A N2 -174.2(2) . . . . ?
C13A C12A C11A C10A -44.4(4) . . . . ?
C13A C14A C10A C9A 120.6(5) . . . . ?
C13A C14A C10A C11A -2.7(6) . . . . ?
C13A C14A C10A C15A -121.4(5) . . . . ?
C13A C14A N1A C8A -144.5(10) . . . . ?
C13A C14A N1A C21A 89.4(12) . . . . ?
C12A C13A C14A C10A -24.5(4) . . . . ?
C12A C13A C14A N1A 87.4(9) . . . . ?
C12A C11A C10A C9A -84.9(7) . . . . ?
C12A C11A C10A C14A 28.9(5) . . . . ?
C12A C11A C10A C15A 147.6(5) . . . . ?
C14 N1 C8 C9 -42.9(15) . . . . ?
C14 N1 C7 C1 163.2(9) . . . . ?
C14 C10 C11 N2 -155.4(4) . . . . ?
C14 C10 C11 C12 -25.2(7) . . . . ?
C14 C10 C9 C8 -26.9(6) . . . . ?
C9 C10 C11 N2 -46.0(8) . . . . ?
C9 C10 C11 C12 84.2(6) . . . . ?
C9 C10 C14 N1 2.2(11) . . . . ?
C9 C10 C14 C13 -117.7(5) . . . . ?
C8 N1 C14 C10 25.3(16) . . . . ?
C8 N1 C14 C13 142.0(10) . . . . ?
C8 N1 C7 C1 -73.3(16) . . . . ?
C7 N1 C14 C10 154.4(9) . . . . ?
C7 N1 C14 C13 -88.9(13) . . . . ?
C7 N1 C8 C9 -170.0(11) . . . . ?
C7 C1 C6 C5 163.6(8) . . . . ?
C8A C9A C10A C11A 137.6(7) . . . . ?
C8A C9A C10A C14A 23.4(6) . . . . ?
C8A C9A C10A C15A -94.7(7) . . . . ?
C21A C1A C6A C5A -163.7(9) . . . . ?
C21A C1A C2A C3A 175.0(12) . . . . ?
C14A C13A C12A C11A 42.3(3) . . . . ?
C15 C10 C11 N2 80.4(7) . . . . ?
C15 C10 C11 C12 -149.4(5) . . . . ?
C15 C10 C14 N1 -119.0(11) . . . . ?
C15 C10 C14 C13 121.2(7) . . . . ?
C15 C10 C9 C8 96.4(8) . . . . ?
C1A C21A N1A C8A 75.2(15) . . . . ?
C1A C21A N1A C14A -162.9(9) . . . . ?
C1A C6A C5A C4A -16(2) . . . . ?
C1A C2A C3A C4A -8(2) . . . . ?
C6A C1A C2A C3A -0.6(17) . . . . ?
C2A C1A C6A C5A 12.4(19) . . . . ?
C2A C3A C4A C5A 4(3) . . . . ?
C3A C4A C5A C6A 10(2) . . . . ?
C10A C9A C8A N1A -42.4(10) . . . . ?
C10A C14A N1A C8A -31.2(16) . . . . ?
C10A C14A N1A C21A -157.3(8) . . . . ?
N1A C21A C1A C6A -169.7(9) . . . . ?
N1A C21A C1A C2A 13.8(12) . . . . ?
N1A C14A C10A C9A 3.4(10) . . . . ?
N1A C14A C10A C11A -119.8(9) . . . . ?
N1A C14A C10A C15A 121.4(9) . . . . ?

#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   SHELX HKL FILE                                           #
#----------------------------------------------------------------------------#


# END of CIF
####################################################################### 
# 
# 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_23JLR016_KM-174-UBE9-2
_database_code_depnum_ccdc_archive 'CCDC 2482167'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina'
;University of Bern
Switzerland
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2025-11-13 downloaded from the CCDC.
;

_audit_creation_date             2023-09-01T14:22:47-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'Cl, C17 H21 N6 O'
_chemical_formula_sum            'C17 H21 Cl N6 O'
_chemical_formula_weight         360.85
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_Int_Tables_number      1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   9.50207(14)
_cell_length_b                   9.90958(14)
_cell_length_c                   10.51714(17)
_cell_angle_alpha                117.9068(15)
_cell_angle_beta                 91.6054(13)
_cell_angle_gamma                92.5887(12)
_cell_volume                     872.90(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.00(10)
_cell_measurement_reflns_used    22651
_cell_measurement_theta_min      2.183
_cell_measurement_theta_max      33.57

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.031
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             380
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
13 2 -3 0.0272
2 -14 9 0.1467
-13 -2 4 0.0212
-3 -3 -10 0.0116
4 4 10 0.0157
-12 -4 7 0.0441
3 14 -7 0.1317

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
13.0527 1.9944 -3.3463 -0.1979 -0.0565 -0.9786
1.7311 -13.7223 8.9459 -0.9337 -0.2217 0.2811
-12.9603 -2.4185 3.6168 0.168 0.0494 0.9845
-3.3597 -3.2759 -10.4307 -0.2317 0.9581 0.1683
4.286 3.6126 9.8316 0.2285 -0.9418 -0.2464
-11.8613 -4.4666 6.7216 0.0225 -0.1317 0.991
2.9984 13.9876 -6.9766 0.855 -0.0213 -0.5862


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
        Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.528
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.993
_oxdiff_exptl_absorpt_empirical_details 
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.252
_oxdiff_exptl_absorpt_empirical_full_min 0.869

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_diffrn_ambient_temperature      173.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0238621
_diffrn_orient_matrix_ub_12      0.0701611
_diffrn_orient_matrix_ub_13      0.0078651
_diffrn_orient_matrix_ub_21      -0.0182028
_diffrn_orient_matrix_ub_22      -0.0350272
_diffrn_orient_matrix_ub_23      -0.0749909
_diffrn_orient_matrix_ub_31      -0.0685578
_diffrn_orient_matrix_ub_32      -0.020966
_diffrn_orient_matrix_ub_33      0.0125274
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_number            53059
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.149
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_coverage         0.992
_reflns_number_total             10595
_reflns_number_gt                8975
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
        List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
        --------------------------------------------------------------------------
  1  ω    -11.00  94.00   0.50    7.00    --   13.07  31.00 -62.00  210
  2  ω    -68.00  37.00   0.50    7.00    --   13.07 -31.00 137.00  210
  3  ω    -35.00  68.00   0.50    7.00    --  -13.54  31.00 -62.00  206
  4  ω    -95.00  10.00   0.50    7.00    --  -13.54 -31.00 137.00  210
  5  ω     -7.00  94.00   0.50    7.00    --   13.07  38.00  90.00  202
  6  ω    -80.00 -21.00   0.50    7.00    --  -13.54 139.00  74.39  118
  7  ω    -83.00 -24.00   0.50    7.00    --  -13.54 144.00  -1.65  118
  8  ω    -19.00  29.00   0.50    7.00    --  -13.54 -99.00-120.00   96
  9  ω    -74.00 -17.00   0.50    7.00    --  -13.54 131.00 150.90  114
 10  ω    -74.00 -17.00   0.50    7.00    --  -13.54 130.00 -94.84  114
 11  ω    -19.00  29.00   0.50    7.00    --  -13.54 -99.00  60.00   96
 12  ω    -19.00  29.00   0.50    7.00    --  -13.54 -99.00 -60.00   96
 13  ω    -62.00  88.00   0.50    7.00    --   13.07   0.00-150.00  300
 14  ω    -62.00  88.00   0.50    7.00    --   13.07   0.00-180.00  300
 15  ω    -25.00  94.00   0.50    7.00    --   13.07  19.00  30.00  238
 16  ω    -62.00  38.00   0.50    7.00    --   13.07   0.00-120.00  200
 17  ω    -88.00 -27.00   0.50    7.00    --  -13.54 151.00  95.40  122
 18  ω    -82.00 -23.00   0.50    7.00    --  -13.54 142.00 171.11  118
 19  ω    -89.00 -28.00   0.50    7.00    --  -13.54 153.00 177.22  122
 20  ω    -84.00 -25.00   0.50    7.00    --  -13.54 146.00-140.24  118
 21  ω    -86.00 -26.00   0.50    7.00    --  -13.54 148.00 -51.20  120
 22  ω    -19.00  29.00   0.50    7.00    --  -13.54 -99.00 120.00   96
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   TWINNING                                                 #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.0698P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10595
_refine_ls_number_parameters     607
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 3639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(14)
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_olex2_refinement_description    
;
        1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
        2. Rigid bond restraints
 N7, C18, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N7A, C18A, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2, C1, N1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2, C1A, N1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
        3. Uiso/Uaniso restraints and constraints
        C18A \\sim C18: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
        0.008 within 1.7A
        Uanis(N1A) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for
        terminal atoms of 0.01
        Uanis(N7) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(N7A) \\sim Ueq, Uanis(C18A)
        \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005
        4. Others
 Sof(H2BC)=Sof(H2BD)=Sof(N1A)=Sof(C1A)=1-FVAR(1)
 Sof(H2AA)=Sof(H2AB)=Sof(C1)=Sof(N1)=FVAR(1)
 Sof(H19C)=Sof(H19D)=Sof(N7A)=Sof(C18A)=1-FVAR(2)
 Sof(H19A)=Sof(H19B)=Sof(C18)=Sof(N7)=FVAR(2)
        5.a Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD), C19(H19A,H19B), C19(H19C,H19D)
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.56821(6) 1.03269(7) 0.74542(7) 0.03297(17) Uani 1 1 d . . . . .
Cl2 Cl 0.43770(6) -0.03374(8) 0.23929(7) 0.03651(18) Uani 1 1 d . . . . .
N6 N 0.1448(2) 0.0796(3) 0.3706(2) 0.0246(5) Uani 1 1 d . . . . .
N9 N 0.8057(2) 0.6830(3) 0.4257(3) 0.0274(5) Uani 1 1 d . . . . .
N10 N 1.2728(3) 0.8917(3) 0.5454(3) 0.0302(5) Uani 1 1 d . . . . .
N11 N 1.0963(3) 1.0390(3) 0.7020(3) 0.0288(5) Uani 1 1 d . . . . .
O1 O 0.6567(3) 0.6212(3) 0.7468(3) 0.0531(7) Uani 1 1 d . . . . .
N3 N 0.1989(2) 0.3010(3) 0.5853(2) 0.0241(5) Uani 1 1 d . . . . .
N2 N 0.4771(2) 0.7280(3) 0.8892(3) 0.0299(5) Uani 1 1 d . . . . .
H2 H 0.454(4) 0.793(4) 0.969(4) 0.036 Uiso 1 1 d . U . . .
N8 N 0.5083(2) 0.3147(3) 0.0615(2) 0.0278(5) Uani 1 1 d . . . . .
H8 H 0.535(4) 0.240(4) -0.009(4) 0.033 Uiso 1 1 d . U . . .
N12 N 0.8668(3) 0.9217(3) 0.6215(2) 0.0237(5) Uani 1 1 d . . . . .
N5 N -0.0834(3) -0.0396(3) 0.2796(3) 0.0281(5) Uani 1 1 d . . . . .
O2 O 0.3345(3) 0.4096(3) 0.2170(3) 0.0478(6) Uani 1 1 d . . . . .
C29 C 0.9043(3) 0.7923(3) 0.5033(3) 0.0227(5) Uani 1 1 d . . . . .
N4 N -0.2653(3) 0.0972(3) 0.4306(3) 0.0308(6) Uani 1 1 d . . . . .
C13 C -0.0462(3) 0.2064(3) 0.5029(3) 0.0245(5) Uani 1 1 d . . . . .
C33 C 1.1376(3) 0.9159(3) 0.5831(3) 0.0235(5) Uani 1 1 d . . . . .
C32 C 1.2753(3) 0.7561(4) 0.4214(4) 0.0381(7) Uani 1 1 d . . . . .
H32 H 1.365(4) 0.720(5) 0.371(4) 0.046 Uiso 1 1 d . U . . .
C24 C 0.8286(3) 0.5419(3) 0.2910(3) 0.0297(6) Uani 1 1 d . . . . .
H24 H 0.916(4) 0.492(4) 0.302(4) 0.036 Uiso 1 1 d . U . . .
C30 C 1.0507(3) 0.7906(3) 0.4787(3) 0.0241(5) Uani 1 1 d . . . . .
C16 C -0.1281(3) 0.0811(3) 0.3965(3) 0.0248(5) Uani 1 1 d . . . . .
C25 C 0.6931(3) 0.4369(3) 0.2667(3) 0.0275(5) Uani 1 1 d . . . . .
C34 C 0.9609(3) 1.0352(3) 0.7136(3) 0.0283(6) Uani 1 1 d . . . . .
H34 H 0.916(4) 1.117(4) 0.794(4) 0.034 Uiso 1 1 d . U . . .
C31 C 1.1421(3) 0.6895(4) 0.3761(4) 0.0338(7) Uani 1 1 d . . . . .
H31 H 1.127(4) 0.590(5) 0.282(4) 0.041 Uiso 1 1 d . U . . .
C10 C 0.3928(3) 0.3571(3) 0.7467(3) 0.0293(5) Uani 1 1 d . . . . .
H10A H 0.491(4) 0.384(4) 0.768(4) 0.035 Uiso 1 1 d . U . . .
H10B H 0.374(4) 0.284(4) 0.784(4) 0.035 Uiso 1 1 d . U . . .
C12 C 0.1019(3) 0.2020(3) 0.4916(3) 0.0215(5) Uani 1 1 d . . . . .
C17 C 0.0530(3) -0.0337(3) 0.2712(3) 0.0286(6) Uani 1 1 d . . . . .
H17 H 0.097(4) -0.110(4) 0.195(4) 0.034 Uiso 1 1 d . U . . .
C8 C 0.3048(3) 0.4972(3) 0.8090(3) 0.0245(5) Uani 1 1 d . . . . .
C3 C 0.6123(3) 0.7184(4) 0.8588(3) 0.0321(6) Uani 1 1 d . . . . .
C11 C 0.3512(3) 0.2771(3) 0.5855(3) 0.0280(5) Uani 1 1 d . . . . .
H11A H 0.393(4) 0.325(4) 0.530(4) 0.034 Uiso 1 1 d . U . . .
H11B H 0.360(4) 0.176(4) 0.551(4) 0.034 Uiso 1 1 d . U . . .
C20 C 0.3805(3) 0.3062(4) 0.1093(3) 0.0314(6) Uani 1 1 d . . . . .
C2 C 0.7130(4) 0.8427(4) 0.9731(4) 0.0417(7) Uani 1 1 d . U . . .
H2AA H 0.719325 0.934378 0.958313 0.05 Uiso 0.807(9) 1 calc R U P A 1
H2AB H 0.679964 0.872729 1.070603 0.05 Uiso 0.807(9) 1 calc R U P A 1
H2BC H 0.668417 0.940653 1.002604 0.05 Uiso 0.193(9) 1 calc R U P A 2
H2BD H 0.714004 0.824102 1.057719 0.05 Uiso 0.193(9) 1 calc R U P A 2
C26 C 0.7284(4) 0.2743(4) 0.2267(4) 0.0390(7) Uani 1 1 d . . . . .
H26A H 0.776(5) 0.228(5) 0.139(5) 0.058 Uiso 1 1 d . U . . .
H26B H 0.640(5) 0.203(5) 0.214(5) 0.058 Uiso 1 1 d . U . . .
H26C H 0.788(5) 0.269(5) 0.299(5) 0.058 Uiso 1 1 d . U . . .
C14 C -0.1430(3) 0.3043(4) 0.6033(4) 0.0360(7) Uani 1 1 d . . . . .
H14 H -0.116(4) 0.404(5) 0.677(4) 0.043 Uiso 1 1 d . U . . .
C4 C 0.3674(3) 0.6284(3) 0.7831(3) 0.0303(5) Uani 1 1 d . . . . .
H4A H 0.408(4) 0.582(4) 0.688(4) 0.036 Uiso 1 1 d . U . . .
C9 C 0.2757(3) 0.5508(4) 0.9668(3) 0.0314(6) Uani 1 1 d . . . . .
H9A H 0.228(4) 0.481(5) 0.986(4) 0.047 Uiso 1 1 d . U . . .
H9B H 0.220(4) 0.638(5) 1.008(5) 0.047 Uiso 1 1 d . U . . .
H9C H 0.359(4) 0.579(5) 1.027(4) 0.047 Uiso 1 1 d . U . . .
C27 C 0.6204(3) 0.5138(4) 0.4101(3) 0.0347(6) Uani 1 1 d . . . . .
H27A H 0.522(4) 0.490(4) 0.397(4) 0.042 Uiso 1 1 d . U . . .
H27B H 0.657(4) 0.475(4) 0.477(4) 0.042 Uiso 1 1 d . U . . .
C22 C 0.7250(4) 0.4555(4) 0.0474(4) 0.0364(7) Uani 1 1 d . . . . .
H22A H 0.701(4) 0.495(5) -0.005(4) 0.044 Uiso 1 1 d . U . . .
H22B H 0.764(4) 0.350(5) -0.009(4) 0.044 Uiso 1 1 d . U . . .
C21 C 0.6110(3) 0.4437(3) 0.1406(3) 0.0265(5) Uani 1 1 d . . . . .
H21 H 0.560(3) 0.534(4) 0.184(4) 0.032 Uiso 1 1 d . U . . .
C7 C 0.1668(3) 0.4461(3) 0.7110(3) 0.0271(6) Uani 1 1 d . . . . .
H7 H 0.094(4) 0.424(4) 0.758(4) 0.032 Uiso 1 1 d . U . . .
C19 C 0.2953(4) 0.1560(4) 0.0220(4) 0.0418(8) Uani 1 1 d . U . . .
H19A H 0.30948 0.083919 0.061292 0.05 Uiso 0.42(2) 1 calc R U P B 1
H19B H 0.318447 0.107124 -0.080541 0.05 Uiso 0.42(2) 1 calc R U P B 1
H19C H 0.306701 0.123966 -0.081305 0.05 Uiso 0.58(2) 1 calc R U P B 2
H19D H 0.336818 0.078134 0.042919 0.05 Uiso 0.58(2) 1 calc R U P B 2
C28 C 0.6595(3) 0.6824(3) 0.4693(3) 0.0347(6) Uani 1 1 d . . . . .
H28A H 0.602(4) 0.732(5) 0.431(4) 0.042 Uiso 1 1 d . U . . .
H28B H 0.653(4) 0.737(4) 0.572(4) 0.042 Uiso 1 1 d . U . . .
C5 C 0.2404(4) 0.7107(4) 0.7698(4) 0.0423(8) Uani 1 1 d . . . . .
H5A H 0.270(4) 0.778(5) 0.727(4) 0.051 Uiso 1 1 d . U . . .
H5B H 0.207(5) 0.767(5) 0.868(5) 0.051 Uiso 1 1 d . U . . .
C15 C -0.2729(3) 0.2334(5) 0.5536(4) 0.0389(7) Uani 1 1 d . . . . .
H15 H -0.357(5) 0.270(5) 0.590(4) 0.047 Uiso 1 1 d . U . . .
C23 C 0.8380(4) 0.5679(4) 0.1577(3) 0.0446(8) Uani 1 1 d . . . . .
H23A H 0.822(4) 0.670(5) 0.179(5) 0.053 Uiso 1 1 d . U . . .
H23B H 0.935(5) 0.551(5) 0.126(4) 0.053 Uiso 1 1 d . U . . .
C6 C 0.1382(4) 0.5740(4) 0.6695(4) 0.0439(8) Uani 1 1 d . . . . .
H6A H 0.149(4) 0.547(5) 0.572(5) 0.053 Uiso 1 1 d . U . . .
H6B H 0.042(5) 0.602(5) 0.680(4) 0.053 Uiso 1 1 d . U . . .
C1 C 0.8534(5) 0.7758(7) 0.9567(5) 0.0453(12) Uani 0.807(9) 1 d . U P A 1
N1 N 0.9582(5) 0.7177(7) 0.9436(5) 0.0684(17) Uani 0.807(9) 1 d . U P A 1
C18 C 0.1415(14) 0.211(2) 0.0421(19) 0.051(3) Uani 0.42(2) 1 d . U P B 1
N7 N 0.0297(11) 0.246(2) 0.0585(13) 0.073(4) Uani 0.42(2) 1 d . U P B 1
N1A N 0.9593(19) 0.883(3) 0.927(2) 0.068(6) Uani 0.193(9) 1 d . U P A 2
C1A C 0.849(2) 0.868(3) 0.9518(18) 0.041(5) Uani 0.193(9) 1 d . U P A 2
N7A N 0.0333(8) 0.1568(19) 0.0609(10) 0.081(3) Uani 0.58(2) 1 d . U P B 2
C18A C 0.1510(10) 0.1532(16) 0.0435(13) 0.047(2) Uani 0.58(2) 1 d . U P B 2
H6 H 0.240(5) 0.068(5) 0.345(5) 0.057(13) Uiso 1 1 d . . . . .
H10 H 1.339(5) 0.942(5) 0.594(5) 0.039(11) Uiso 1 1 d . . . . .
H4 H -0.332(5) 0.049(5) 0.381(5) 0.039(11) Uiso 1 1 d . . . . .
H12 H 0.785(3) 0.934(3) 0.637(3) 0.014(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N6 C12 1.373(4) . ?
N6 C17 1.370(4) . ?
N6 H6 0.95(5) . ?
N9 C29 1.325(4) . ?
N9 C24 1.483(4) . ?
N9 C28 1.475(3) . ?
N10 C33 1.354(4) . ?
N10 C32 1.367(5) . ?
N10 H10 0.79(5) . ?
N11 C33 1.360(4) . ?
N11 C34 1.296(4) . ?
O1 C3 1.223(4) . ?
N3 C12 1.321(3) . ?
N3 C11 1.477(3) . ?
N3 C7 1.481(3) . ?
N2 H2 0.82(4) . ?
N2 C3 1.329(4) . ?
N2 C4 1.454(4) . ?
N8 H8 0.82(4) . ?
N8 C20 1.341(4) . ?
N8 C21 1.457(3) . ?
N12 C29 1.375(4) . ?
N12 C34 1.358(4) . ?
N12 H12 0.80(3) . ?
N5 C16 1.350(4) . ?
N5 C17 1.302(4) . ?
O2 C20 1.227(4) . ?
C29 C30 1.421(4) . ?
N4 C16 1.358(4) . ?
N4 C15 1.371(5) . ?
N4 H4 0.79(5) . ?
C13 C16 1.402(4) . ?
C13 C12 1.417(4) . ?
C13 C14 1.441(4) . ?
C33 C30 1.418(4) . ?
C32 H32 1.00(4) . ?
C32 C31 1.364(5) . ?
C24 H24 1.02(4) . ?
C24 C25 1.555(4) . ?
C24 C23 1.544(5) . ?
C30 C31 1.429(4) . ?
C25 C26 1.520(4) . ?
C25 C27 1.536(4) . ?
C25 C21 1.550(4) . ?
C34 H34 0.98(4) . ?
C31 H31 1.02(4) . ?
C10 H10A 0.95(4) . ?
C10 H10B 0.98(4) . ?
C10 C8 1.530(4) . ?
C10 C11 1.528(4) . ?
C17 H17 0.93(4) . ?
C8 C4 1.546(4) . ?
C8 C9 1.525(4) . ?
C8 C7 1.553(3) . ?
C3 C2 1.524(4) . ?
C11 H11A 0.99(4) . ?
C11 H11B 0.90(4) . ?
C20 C19 1.512(5) . ?
C2 H2AA 0.99 . ?
C2 H2AB 0.99 . ?
C2 H2BC 0.99 . ?
C2 H2BD 0.99 . ?
C2 C1 1.495(6) . ?
C2 C1A 1.352(19) . ?
C26 H26A 0.95(5) . ?
C26 H26B 1.03(4) . ?
C26 H26C 0.95(5) . ?
C14 H14 0.94(4) . ?
C14 C15 1.354(5) . ?
C4 H4A 0.99(4) . ?
C4 C5 1.526(4) . ?
C9 H9A 0.91(4) . ?
C9 H9B 0.96(4) . ?
C9 H9C 0.95(4) . ?
C27 H27A 0.95(4) . ?
C27 H27B 1.01(4) . ?
C27 C28 1.508(4) . ?
C22 H22A 0.85(4) . ?
C22 H22B 1.02(4) . ?
C22 C21 1.518(4) . ?
C22 C23 1.534(4) . ?
C21 H21 0.95(3) . ?
C7 H7 0.94(3) . ?
C7 C6 1.552(5) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C19 H19C 0.99 . ?
C19 H19D 0.99 . ?
C19 C18 1.570(15) . ?
C19 C18A 1.397(10) . ?
C28 H28A 0.95(4) . ?
C28 H28B 0.96(4) . ?
C5 H5A 1.00(4) . ?
C5 H5B 0.98(4) . ?
C5 C6 1.542(5) . ?
C15 H15 0.92(4) . ?
C23 H23A 0.95(5) . ?
C23 H23B 0.98(4) . ?
C6 H6A 0.94(4) . ?
C6 H6B 0.96(4) . ?
C1 N1 1.152(7) . ?
C18 N7 1.124(17) . ?
N1A C1A 1.10(2) . ?
N7A C18A 1.138(11) . ?

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
C12 N6 H6 124(3) . . ?
C17 N6 C12 123.1(2) . . ?
C17 N6 H6 113(3) . . ?
C29 N9 C24 125.2(2) . . ?
C29 N9 C28 123.4(2) . . ?
C28 N9 C24 111.3(2) . . ?
C33 N10 C32 108.9(3) . . ?
C33 N10 H10 124(3) . . ?
C32 N10 H10 126(3) . . ?
C34 N11 C33 112.8(2) . . ?
C12 N3 C11 124.9(2) . . ?
C12 N3 C7 123.9(2) . . ?
C11 N3 C7 111.1(2) . . ?
C3 N2 H2 120(3) . . ?
C3 N2 C4 121.2(2) . . ?
C4 N2 H2 119(3) . . ?
C20 N8 H8 119(2) . . ?
C20 N8 C21 122.6(2) . . ?
C21 N8 H8 118(2) . . ?
C29 N12 H12 119(2) . . ?
C34 N12 C29 123.8(3) . . ?
C34 N12 H12 117(2) . . ?
C17 N5 C16 113.0(2) . . ?
N9 C29 N12 119.2(2) . . ?
N9 C29 C30 126.5(3) . . ?
N12 C29 C30 114.3(2) . . ?
C16 N4 C15 108.1(3) . . ?
C16 N4 H4 127(3) . . ?
C15 N4 H4 123(3) . . ?
C16 C13 C12 116.3(3) . . ?
C16 C13 C14 106.4(3) . . ?
C12 C13 C14 137.1(3) . . ?
N10 C33 N11 124.8(3) . . ?
N10 C33 C30 107.8(3) . . ?
N11 C33 C30 127.4(3) . . ?
N10 C32 H32 122(2) . . ?
C31 C32 N10 110.5(3) . . ?
C31 C32 H32 127(2) . . ?
N9 C24 H24 111(2) . . ?
N9 C24 C25 104.0(2) . . ?
N9 C24 C23 113.5(3) . . ?
C25 C24 H24 111(2) . . ?
C23 C24 H24 110(2) . . ?
C23 C24 C25 107.1(2) . . ?
C29 C30 C31 137.0(3) . . ?
C33 C30 C29 116.2(3) . . ?
C33 C30 C31 106.7(2) . . ?
N5 C16 N4 123.7(3) . . ?
N5 C16 C13 127.7(3) . . ?
N4 C16 C13 108.6(3) . . ?
C26 C25 C24 111.5(2) . . ?
C26 C25 C27 112.4(3) . . ?
C26 C25 C21 111.2(2) . . ?
C27 C25 C24 104.5(2) . . ?
C27 C25 C21 113.4(2) . . ?
C21 C25 C24 103.2(2) . . ?
N11 C34 N12 125.5(3) . . ?
N11 C34 H34 122(2) . . ?
N12 C34 H34 112(2) . . ?
C32 C31 C30 106.0(3) . . ?
C32 C31 H31 120(2) . . ?
C30 C31 H31 134(2) . . ?
H10A C10 H10B 104(3) . . ?
C8 C10 H10A 112(2) . . ?
C8 C10 H10B 115(2) . . ?
C11 C10 H10A 113(2) . . ?
C11 C10 H10B 108(2) . . ?
C11 C10 C8 104.2(2) . . ?
N6 C12 C13 114.7(2) . . ?
N3 C12 N6 118.7(2) . . ?
N3 C12 C13 126.6(3) . . ?
N6 C17 H17 114(2) . . ?
N5 C17 N6 124.8(3) . . ?
N5 C17 H17 121(2) . . ?
C10 C8 C4 112.4(2) . . ?
C10 C8 C7 104.81(19) . . ?
C4 C8 C7 102.0(2) . . ?
C9 C8 C10 112.6(2) . . ?
C9 C8 C4 112.3(2) . . ?
C9 C8 C7 112.0(2) . . ?
O1 C3 N2 124.4(3) . . ?
O1 C3 C2 120.3(3) . . ?
N2 C3 C2 115.2(3) . . ?
N3 C11 C10 101.7(2) . . ?
N3 C11 H11A 106(2) . . ?
N3 C11 H11B 107(2) . . ?
C10 C11 H11A 115(2) . . ?
C10 C11 H11B 108(2) . . ?
H11A C11 H11B 117(3) . . ?
N8 C20 C19 115.0(3) . . ?
O2 C20 N8 123.9(3) . . ?
O2 C20 C19 121.2(3) . . ?
C3 C2 H2AA 110.5 . . ?
C3 C2 H2AB 110.5 . . ?
C3 C2 H2BC 106.4 . . ?
C3 C2 H2BD 106.4 . . ?
H2AA C2 H2AB 108.7 . . ?
H2BC C2 H2BD 106.5 . . ?
C1 C2 C3 106.3(3) . . ?
C1 C2 H2AA 110.5 . . ?
C1 C2 H2AB 110.5 . . ?
C1A C2 C3 123.8(9) . . ?
C1A C2 H2BC 106.4 . . ?
C1A C2 H2BD 106.4 . . ?
C25 C26 H26A 112(3) . . ?
C25 C26 H26B 113(2) . . ?
C25 C26 H26C 113(3) . . ?
H26A C26 H26B 107(4) . . ?
H26A C26 H26C 106(4) . . ?
H26B C26 H26C 105(4) . . ?
C13 C14 H14 123(2) . . ?
C15 C14 C13 105.9(3) . . ?
C15 C14 H14 130(2) . . ?
N2 C4 C8 115.0(2) . . ?
N2 C4 H4A 108(2) . . ?
N2 C4 C5 114.3(2) . . ?
C8 C4 H4A 108(2) . . ?
C5 C4 C8 105.0(2) . . ?
C5 C4 H4A 106(2) . . ?
C8 C9 H9A 116(3) . . ?
C8 C9 H9B 114(2) . . ?
C8 C9 H9C 113(2) . . ?
H9A C9 H9B 104(3) . . ?
H9A C9 H9C 104(4) . . ?
H9B C9 H9C 106(3) . . ?
C25 C27 H27A 112(2) . . ?
C25 C27 H27B 110(2) . . ?
H27A C27 H27B 106(3) . . ?
C28 C27 C25 104.8(2) . . ?
C28 C27 H27A 113(2) . . ?
C28 C27 H27B 111(2) . . ?
H22A C22 H22B 113(3) . . ?
C21 C22 H22A 115(3) . . ?
C21 C22 H22B 109(2) . . ?
C21 C22 C23 103.4(2) . . ?
C23 C22 H22A 106(3) . . ?
C23 C22 H22B 110(2) . . ?
N8 C21 C25 113.9(2) . . ?
N8 C21 C22 113.0(2) . . ?
N8 C21 H21 108(2) . . ?
C25 C21 H21 106(2) . . ?
C22 C21 C25 104.4(2) . . ?
C22 C21 H21 112(2) . . ?
N3 C7 C8 104.2(2) . . ?
N3 C7 H7 108(2) . . ?
N3 C7 C6 112.5(2) . . ?
C8 C7 H7 109(2) . . ?
C6 C7 C8 107.3(2) . . ?
C6 C7 H7 115(2) . . ?
C20 C19 H19A 111.6 . . ?
C20 C19 H19B 111.6 . . ?
C20 C19 H19C 108 . . ?
C20 C19 H19D 108 . . ?
C20 C19 C18 100.7(7) . . ?
H19A C19 H19B 109.4 . . ?
H19C C19 H19D 107.2 . . ?
C18 C19 H19A 111.6 . . ?
C18 C19 H19B 111.6 . . ?
C18A C19 C20 117.2(6) . . ?
C18A C19 H19C 108 . . ?
C18A C19 H19D 108 . . ?
N9 C28 C27 102.3(2) . . ?
N9 C28 H28A 110(2) . . ?
N9 C28 H28B 112(2) . . ?
C27 C28 H28A 114(2) . . ?
C27 C28 H28B 111(2) . . ?
H28A C28 H28B 106(3) . . ?
C4 C5 H5A 109(2) . . ?
C4 C5 H5B 106(3) . . ?
C4 C5 C6 101.1(3) . . ?
H5A C5 H5B 114(3) . . ?
C6 C5 H5A 114(2) . . ?
C6 C5 H5B 112(3) . . ?
N4 C15 H15 122(3) . . ?
C14 C15 N4 110.9(3) . . ?
C14 C15 H15 127(3) . . ?
C24 C23 H23A 113(3) . . ?
C24 C23 H23B 108(2) . . ?
C22 C23 C24 105.4(2) . . ?
C22 C23 H23A 110(3) . . ?
C22 C23 H23B 114(2) . . ?
H23A C23 H23B 106(3) . . ?
C7 C6 H6A 115(2) . . ?
C7 C6 H6B 113(3) . . ?
C5 C6 C7 105.1(2) . . ?
C5 C6 H6A 111(3) . . ?
C5 C6 H6B 111(3) . . ?
H6A C6 H6B 101(4) . . ?
N1 C1 C2 176.6(6) . . ?
N7 C18 C19 176.5(16) . . ?
N1A C1A C2 176(2) . . ?
N7A C18A C19 177.1(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N9 C29 C30 C33 -175.2(3) . . . . ?
N9 C29 C30 C31 1.0(6) . . . . ?
N9 C24 C25 C26 -134.7(3) . . . . ?
N9 C24 C25 C27 -13.1(3) . . . . ?
N9 C24 C25 C21 105.8(2) . . . . ?
N9 C24 C23 C22 -124.3(3) . . . . ?
N10 C33 C30 C29 177.5(2) . . . . ?
N10 C33 C30 C31 0.1(3) . . . . ?
N10 C32 C31 C30 0.1(4) . . . . ?
N11 C33 C30 C29 -1.7(4) . . . . ?
N11 C33 C30 C31 -179.1(3) . . . . ?
O1 C3 C2 C1 -28.0(5) . . . . ?
O1 C3 C2 C1A 9.8(14) . . . . ?
N3 C7 C6 C5 -126.1(3) . . . . ?
N2 C3 C2 C1 153.9(4) . . . . ?
N2 C3 C2 C1A -168.3(13) . . . . ?
N2 C4 C5 C6 -171.8(3) . . . . ?
N8 C20 C19 C18 -148.6(8) . . . . ?
N8 C20 C19 C18A -164.4(6) . . . . ?
N12 C29 C30 C33 3.9(4) . . . . ?
N12 C29 C30 C31 -179.8(3) . . . . ?
O2 C20 C19 C18 32.7(9) . . . . ?
O2 C20 C19 C18A 17.0(7) . . . . ?
C29 N9 C24 C25 166.0(3) . . . . ?
C29 N9 C24 C23 -77.9(4) . . . . ?
C29 N9 C28 C27 -146.8(3) . . . . ?
C29 N12 C34 N11 1.3(5) . . . . ?
C29 C30 C31 C32 -176.7(4) . . . . ?
C13 C14 C15 N4 0.8(4) . . . . ?
C33 N10 C32 C31 -0.1(4) . . . . ?
C33 N11 C34 N12 1.3(4) . . . . ?
C33 C30 C31 C32 -0.2(4) . . . . ?
C32 N10 C33 N11 179.2(3) . . . . ?
C32 N10 C33 C30 -0.1(3) . . . . ?
C24 N9 C29 N12 176.2(3) . . . . ?
C24 N9 C29 C30 -4.7(5) . . . . ?
C24 N9 C28 C27 29.3(3) . . . . ?
C24 C25 C27 C28 31.0(3) . . . . ?
C24 C25 C21 N8 158.3(2) . . . . ?
C24 C25 C21 C22 34.5(3) . . . . ?
C16 N5 C17 N6 1.4(4) . . . . ?
C16 N4 C15 C14 -2.0(4) . . . . ?
C16 C13 C12 N6 4.7(4) . . . . ?
C16 C13 C12 N3 -174.4(3) . . . . ?
C16 C13 C14 C15 0.6(4) . . . . ?
C25 C24 C23 C22 -10.1(4) . . . . ?
C25 C27 C28 N9 -36.4(3) . . . . ?
C34 N11 C33 N10 180.0(3) . . . . ?
C34 N11 C33 C30 -1.0(4) . . . . ?
C34 N12 C29 N9 175.3(3) . . . . ?
C34 N12 C29 C30 -4.0(4) . . . . ?
C10 C8 C4 N2 -84.6(3) . . . . ?
C10 C8 C4 C5 149.0(2) . . . . ?
C10 C8 C7 N3 -12.8(3) . . . . ?
C10 C8 C7 C6 -132.2(3) . . . . ?
C12 N6 C17 N5 -0.3(5) . . . . ?
C12 N3 C11 C10 -145.1(3) . . . . ?
C12 N3 C7 C8 164.4(3) . . . . ?
C12 N3 C7 C6 -79.7(3) . . . . ?
C12 C13 C16 N5 -4.2(5) . . . . ?
C12 C13 C16 N4 174.6(2) . . . . ?
C12 C13 C14 C15 -174.7(4) . . . . ?
C17 N6 C12 N3 176.2(3) . . . . ?
C17 N6 C12 C13 -2.9(4) . . . . ?
C17 N5 C16 N4 -177.6(3) . . . . ?
C17 N5 C16 C13 0.9(4) . . . . ?
C8 C10 C11 N3 -37.3(3) . . . . ?
C8 C4 C5 C6 -44.9(3) . . . . ?
C8 C7 C6 C5 -12.0(4) . . . . ?
C3 N2 C4 C8 104.7(3) . . . . ?
C3 N2 C4 C5 -133.8(3) . . . . ?
C11 N3 C12 N6 -12.0(4) . . . . ?
C11 N3 C12 C13 167.0(3) . . . . ?
C11 N3 C7 C8 -11.3(3) . . . . ?
C11 N3 C7 C6 104.5(3) . . . . ?
C11 C10 C8 C4 -78.7(3) . . . . ?
C11 C10 C8 C9 153.3(2) . . . . ?
C11 C10 C8 C7 31.3(3) . . . . ?
C20 N8 C21 C25 80.0(3) . . . . ?
C20 N8 C21 C22 -161.1(3) . . . . ?
C26 C25 C27 C28 152.0(3) . . . . ?
C26 C25 C21 N8 38.7(3) . . . . ?
C26 C25 C21 C22 -85.1(3) . . . . ?
C14 C13 C16 N5 179.4(3) . . . . ?
C14 C13 C16 N4 -1.8(3) . . . . ?
C14 C13 C12 N6 179.7(3) . . . . ?
C14 C13 C12 N3 0.6(6) . . . . ?
C4 N2 C3 O1 -5.4(5) . . . . ?
C4 N2 C3 C2 172.6(3) . . . . ?
C4 C8 C7 N3 104.6(2) . . . . ?
C4 C8 C7 C6 -14.9(3) . . . . ?
C4 C5 C6 C7 34.3(4) . . . . ?
C9 C8 C4 N2 43.6(3) . . . . ?
C9 C8 C4 C5 -82.9(3) . . . . ?
C9 C8 C7 N3 -135.1(2) . . . . ?
C9 C8 C7 C6 105.4(3) . . . . ?
C27 C25 C21 N8 -89.3(3) . . . . ?
C27 C25 C21 C22 147.0(2) . . . . ?
C21 N8 C20 O2 5.5(5) . . . . ?
C21 N8 C20 C19 -173.1(3) . . . . ?
C21 C25 C27 C28 -80.7(3) . . . . ?
C21 C22 C23 C24 31.5(4) . . . . ?
C7 N3 C12 N6 172.9(2) . . . . ?
C7 N3 C12 C13 -8.1(5) . . . . ?
C7 N3 C11 C10 30.6(3) . . . . ?
C7 C8 C4 N2 163.7(2) . . . . ?
C7 C8 C4 C5 37.2(3) . . . . ?
C28 N9 C29 N12 -8.3(4) . . . . ?
C28 N9 C29 C30 170.9(3) . . . . ?
C28 N9 C24 C25 -10.1(3) . . . . ?
C28 N9 C24 C23 106.0(3) . . . . ?
C15 N4 C16 N5 -178.8(3) . . . . ?
C15 N4 C16 C13 2.3(3) . . . . ?
C23 C24 C25 C26 104.8(3) . . . . ?
C23 C24 C25 C27 -133.6(3) . . . . ?
C23 C24 C25 C21 -14.7(3) . . . . ?
C23 C22 C21 N8 -165.6(3) . . . . ?
C23 C22 C21 C25 -41.3(3) . . . . ?


#----------------------------------------------------------------------------#
#                   VALIDATION REPLY FORM                                    #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   SHELX RES FILE                                           #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   SHELX HKL FILE                                           #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   SHELX FAB FILE                                           #
#----------------------------------------------------------------------------#

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
