# Supplementary Information (SI) for RSC Mechanochemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ProNA
_database_code_depnum_ccdc_archive 'CCDC 2371670'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 N O2, C6 H4 N O2'
_chemical_formula_sum            'C22 H26 N2 O4'
_chemical_formula_weight         382.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C88  H92  N8  O16  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.3968(3)
_cell_length_b                   8.65850(10)
_cell_length_c                   16.3567(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.839(2)
_cell_angle_gamma                90
_cell_volume                     2051.15(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12708
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3920
_cell_measurement_theta_min      5.4940
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0300
5 0 7 0.0207
-5 -1 -7 0.0300
-4 5 3 0.0552
-3 -5 -2 0.0812
-2 0 -9 0.0374
8 -1 -9 0.0318
6 4 -7 0.0529
0 -6 0 0.0810
4 4 4 0.0384
9 0 1 0.0168
7 4 0 0.0345
-9 0 -1 0.0281

_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0025 -0.0007 0.9990 -0.0391 0.1118 -0.0103
4.8831 -0.2266 6.9404 -0.9539 -0.2829 -0.0997
-4.9669 -0.6292 -6.7981 0.9573 0.2841 -0.0532
-3.6697 5.1630 2.7767 -0.1321 0.4472 0.8847
-2.7238 -5.0747 -2.3215 0.4566 0.1346 -0.8794
-1.9994 -0.1292 -9.0572 0.9979 -0.0257 0.0592
8.0603 -0.8763 -8.6019 0.3822 -0.9216 -0.0676
6.0790 3.5609 -6.9656 0.2737 -0.6588 0.7008
0.4454 -5.6112 0.1545 0.0403 -0.0988 -0.9943
3.8771 4.0911 4.2368 -0.6953 -0.2056 0.6887
9.0986 -0.0569 0.8495 -0.6084 -0.7936 -0.0091
7.2411 3.5943 -0.0605 -0.4652 -0.6075 0.6438
-9.0444 0.4285 -0.9197 0.6067 0.7913 0.0756

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27202
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.036
_diffrn_reflns_theta_min         3.051
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  26.00   0.50    3.40    --  -47.76   8.00  48.00  100
  2  ω   -121.00 -29.00   0.50    3.40    --  -47.76  -8.00-126.00  184
  3  ω     29.00 122.00   0.50    3.40    --   47.76   8.00  48.00  186
  4  ω   -165.00 -73.00   0.50   13.59    --  -91.75  -8.00-126.00  184
  5  ω     88.00 178.00   0.50   13.59    --  107.31   8.00  48.00  180
  6  ω   -120.00 -73.00   0.50    3.40    --  -47.76-125.00-120.00   94
  7  ω     34.00  96.00   0.50    3.40    --   47.76-125.00-180.00  124
  8  ω    -26.00  28.00   0.50    3.40    --   47.76  -8.00-126.00  108
  9  ω    -25.00  45.00   0.50    3.40    --   47.76 -38.00 120.00  140
 10  ω   -103.00 -19.00   0.50   13.59    --  -91.75  77.00-180.00  168
 11  ω    -85.00 -19.00   0.50   13.59    --  -91.75 125.00  60.00  132
 12  ω   -163.00 -86.00   0.50   13.59    --  -91.75 -99.00   0.00  154
 13  ω     35.00  68.00   0.50   13.59    --  107.31 -57.00-180.00   66
 14  ω     35.00  68.00   0.50   13.59    --  107.31 -57.00 -60.00   66
 15  ω     35.00  68.00   0.50   13.59    --  107.31 -57.00  30.00   66
 16  ω     35.00 106.00   0.50   13.59    --  107.31 -99.00 -90.00  142
 17  ω     94.00 178.00   0.50   13.59    --  107.31  38.00 -60.00  168
 18  ω     35.00 106.00   0.50   13.59    --  107.31 -99.00-180.00  142
 19  ω     35.00  68.00   0.50   13.59    --  107.31 -57.00 150.00   66
 20  ω     35.00 106.00   0.50   13.59    --  107.31 -99.00  90.00  142
 21  ω     35.00 106.00   0.50   13.59    --  107.31 -99.00 -30.00  142
 22  ω     25.00 121.00   0.50    3.40    --   47.76  77.00 -60.00  192
 23  ω     25.00 121.00   0.50    3.40    --   47.76  77.00 120.00  192
 24  ω     25.00 121.00   0.50    3.40    --   47.76  77.00  30.00  192
 25  ω    -27.00  29.00   0.50    3.40    --   47.76 -19.00 -90.00  112
 26  ω     25.00 121.00   0.50    3.40    --   47.76  77.00  90.00  192
 27  ω     25.00 121.00   0.50    3.40    --   47.76  77.00-150.00  192
 28  ω   -163.00-132.00   0.50   13.59    --  -91.75 -77.00-120.00   62
 29  ω     95.00 178.00   0.50   13.59    --  107.31  19.00 150.00  166
;
_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      -0.0578827000
_diffrn_orient_matrix_UB_12      -0.0144490000
_diffrn_orient_matrix_UB_13      -0.0971948000
_diffrn_orient_matrix_UB_21      -0.0892410000
_diffrn_orient_matrix_UB_22      0.0111387000
_diffrn_orient_matrix_UB_23      0.0223844000
_diffrn_orient_matrix_UB_31      0.0009674000
_diffrn_orient_matrix_UB_32      0.1770182000
_diffrn_orient_matrix_UB_33      -0.0092715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3592
_reflns_number_total             4208
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+1.2002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1248
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.13401(11) 0.16947(19) 0.82226(10) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.08419(12) 0.0615(2) 0.76295(10) 0.0311(4) Uani 1 1 d . . . . .
H2 H 0.104792 0.029262 0.717103 0.037 Uiso 1 1 calc R U . . .
C3 C 0.00282(13) -0.0010(2) 0.77028(11) 0.0352(4) Uani 1 1 d . . . . .
H3 H -0.031057 -0.074769 0.728634 0.042 Uiso 1 1 calc R U . . .
C4 C -0.02860(12) 0.0409(2) 0.83500(11) 0.0351(4) Uani 1 1 d . . . . .
H4 H -0.083625 -0.003402 0.838633 0.042 Uiso 1 1 calc R U . . .
C5 C 0.02107(11) 0.1511(2) 0.89715(11) 0.0291(4) Uani 1 1 d . . . . .
C6 C -0.01041(12) 0.2019(2) 0.96499(12) 0.0357(4) Uani 1 1 d . . . . .
H6 H -0.065219 0.158675 0.969726 0.043 Uiso 1 1 calc R U . . .
C7 C 0.03610(14) 0.3105(2) 1.02298(12) 0.0382(4) Uani 1 1 d . . . . .
H7 H 0.013682 0.342577 1.067682 0.046 Uiso 1 1 calc R U . . .
C8 C 0.11729(13) 0.3756(2) 1.01723(11) 0.0344(4) Uani 1 1 d . . . . .
H8 H 0.149189 0.452500 1.057749 0.041 Uiso 1 1 calc R U . . .
C9 C 0.15087(11) 0.32924(19) 0.95359(10) 0.0275(3) Uani 1 1 d . . . . .
H9 H 0.206278 0.373426 0.950816 0.033 Uiso 1 1 calc R U . . .
C10 C 0.10399(11) 0.21643(18) 0.89208(9) 0.0242(3) Uani 1 1 d . . . . .
C11 C 0.23806(12) 0.2120(2) 0.74582(11) 0.0299(4) Uani 1 1 d . . . . .
H11A H 0.184710 0.227371 0.691821 0.036 Uiso 1 1 calc R U . . .
H11B H 0.259933 0.104222 0.746978 0.036 Uiso 1 1 calc R U . . .
C12 C 0.31434(11) 0.32333(19) 0.74908(11) 0.0278(3) Uani 1 1 d . . . . .
H12 H 0.362713 0.321032 0.808148 0.033 Uiso 1 1 calc R U . . .
C13 C 0.35673(12) 0.2775(2) 0.68110(11) 0.0294(4) Uani 1 1 d . . . . .
H13A H 0.377271 0.168544 0.689912 0.035 Uiso 1 1 calc R U . . .
H13B H 0.309960 0.287082 0.622308 0.035 Uiso 1 1 calc R U . . .
C14 C 0.49320(11) 0.32445(19) 0.63466(10) 0.0265(3) Uani 1 1 d . . . . .
H14 H 0.510111 0.213747 0.648993 0.032 Uiso 1 1 calc R U . . .
C15 C 0.58126(11) 0.4199(2) 0.66060(11) 0.0311(4) Uani 1 1 d . . . . .
H15A H 0.565479 0.529638 0.650890 0.047 Uiso 1 1 calc R U . . .
H15B H 0.618671 0.388906 0.625404 0.047 Uiso 1 1 calc R U . . .
H15C H 0.616389 0.402792 0.722217 0.047 Uiso 1 1 calc R U . . .
C16 C 0.43735(12) 0.3365(2) 0.53840(10) 0.0320(4) Uani 1 1 d . . . . .
H16A H 0.382934 0.269595 0.524862 0.048 Uiso 1 1 calc R U . . .
H16B H 0.475513 0.303933 0.504213 0.048 Uiso 1 1 calc R U . . .
H16C H 0.417588 0.443660 0.524063 0.048 Uiso 1 1 calc R U . . .
N1 N 0.43653(9) 0.37884(16) 0.68825(9) 0.0250(3) Uani 1 1 d . . . . .
H1A H 0.4172(14) 0.481(3) 0.6730(13) 0.037(5) Uiso 1 1 d . . . . .
H1B H 0.4751(15) 0.382(2) 0.7483(15) 0.043(6) Uiso 1 1 d . . . . .
O1 O 0.21172(8) 0.24184(14) 0.82040(7) 0.0309(3) Uani 1 1 d . . . . .
O2 O 0.28038(8) 0.47713(14) 0.72871(8) 0.0307(3) Uani 1 1 d . . . . .
H2A H 0.2828(17) 0.524(3) 0.7819(16) 0.057(7) Uiso 1 1 d . . . . .
C17 C 0.34122(11) 0.79792(18) 0.52845(10) 0.0250(3) Uani 1 1 d . . . . .
C18 C 0.26793(11) 0.69658(19) 0.51660(11) 0.0282(3) Uani 1 1 d . . . . .
H18 H 0.265176 0.633267 0.563090 0.034 Uiso 1 1 calc R U . . .
C19 C 0.19893(11) 0.6892(2) 0.43597(11) 0.0305(4) Uani 1 1 d . . . . .
H19 H 0.147413 0.622594 0.426497 0.037 Uiso 1 1 calc R U . . .
C20 C 0.20672(11) 0.7810(2) 0.36961(11) 0.0303(4) Uani 1 1 d . . . . .
H20 H 0.159468 0.775003 0.314354 0.036 Uiso 1 1 calc R U . . .
C21 C 0.34238(12) 0.88646(18) 0.45777(10) 0.0280(3) Uani 1 1 d . . . . .
H21 H 0.392020 0.956640 0.465820 0.034 Uiso 1 1 calc R U . . .
C22 C 0.41824(12) 0.80992(19) 0.61512(10) 0.0281(3) Uani 1 1 d . . . . .
N2 N 0.27713(10) 0.87790(16) 0.37896(9) 0.0301(3) Uani 1 1 d . . . . .
O3 O 0.43239(9) 0.69554(14) 0.66486(7) 0.0359(3) Uani 1 1 d . . . . .
O4 O 0.46226(9) 0.93305(14) 0.63280(8) 0.0406(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(2) . ?
C1 C10 1.429(2) . ?
C1 O1 1.3600(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.407(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.354(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.415(3) . ?
C5 C6 1.423(2) . ?
C5 C10 1.424(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.355(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.403(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.506(2) . ?
C11 O1 1.4336(18) . ?
C12 H12 1.0000 . ?
C12 C13 1.521(2) . ?
C12 O2 1.428(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 N1 1.482(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.520(2) . ?
C14 C16 1.520(2) . ?
C14 N1 1.5069(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 H1A 0.94(2) . ?
N1 H1B 0.96(2) . ?
O2 H2A 0.95(3) . ?
C17 C18 1.390(2) . ?
C17 C21 1.392(2) . ?
C17 C22 1.512(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(2) . ?
C20 H20 0.9500 . ?
C20 N2 1.338(2) . ?
C21 H21 0.9500 . ?
C21 N2 1.341(2) . ?
C22 O3 1.253(2) . ?
C22 O4 1.244(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
C2 C1 C10 120.13(15) . . ?
O1 C1 C2 125.50(14) . . ?
O1 C1 C10 114.35(14) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.02(15) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.88(17) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.55(16) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.65(16) . . ?
C4 C5 C10 120.17(15) . . ?
C6 C5 C10 118.17(16) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.43(16) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.22(16) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.48(17) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.70(16) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C1 118.23(15) . . ?
C9 C10 C1 122.72(14) . . ?
C9 C10 C5 118.99(14) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
O1 C11 H11A 110.3 . . ?
O1 C11 H11B 110.3 . . ?
O1 C11 C12 107.27(13) . . ?
C11 C12 H12 109.7 . . ?
C11 C12 C13 109.28(13) . . ?
C13 C12 H12 109.7 . . ?
O2 C12 C11 111.66(13) . . ?
O2 C12 H12 109.7 . . ?
O2 C12 C13 106.66(13) . . ?
C12 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N1 C13 C12 109.76(13) . . ?
N1 C13 H13A 109.7 . . ?
N1 C13 H13B 109.7 . . ?
C15 C14 H14 108.6 . . ?
C16 C14 H14 108.6 . . ?
C16 C14 C15 112.91(13) . . ?
N1 C14 H14 108.6 . . ?
N1 C14 C15 107.78(13) . . ?
N1 C14 C16 110.20(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 N1 C14 113.42(12) . . ?
C13 N1 H1A 110.9(13) . . ?
C13 N1 H1B 107.7(13) . . ?
C14 N1 H1A 109.5(12) . . ?
C14 N1 H1B 108.8(13) . . ?
H1A N1 H1B 106.2(18) . . ?
C1 O1 C11 116.16(13) . . ?
C12 O2 H2A 106.5(15) . . ?
C18 C17 C21 118.05(15) . . ?
C18 C17 C22 121.03(14) . . ?
C21 C17 C22 120.92(15) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.05(15) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.54(15) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 118.2 . . ?
N2 C20 C19 123.60(15) . . ?
N2 C20 H20 118.2 . . ?
C17 C21 H21 118.3 . . ?
N2 C21 C17 123.46(16) . . ?
N2 C21 H21 118.3 . . ?
O3 C22 C17 117.57(15) . . ?
O4 C22 C17 117.98(15) . . ?
O4 C22 O3 124.45(16) . . ?
C20 N2 C21 117.28(14) . . ?

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
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C10 C5 -1.2(2) . . . . ?
C2 C1 C10 C9 -178.42(15) . . . . ?
C2 C1 O1 C11 5.9(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 178.34(17) . . . . ?
C3 C4 C5 C10 -0.6(3) . . . . ?
C4 C5 C6 C7 -178.22(17) . . . . ?
C4 C5 C10 C1 1.0(2) . . . . ?
C4 C5 C10 C9 178.32(15) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C5 C10 C1 -177.91(15) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C1 177.09(15) . . . . ?
C8 C9 C10 C5 -0.1(2) . . . . ?
C10 C1 C2 C3 1.0(2) . . . . ?
C10 C1 O1 C11 -172.84(13) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
C11 C12 C13 N1 -175.66(13) . . . . ?
C12 C11 O1 C1 170.14(13) . . . . ?
C12 C13 N1 C14 169.63(13) . . . . ?
C15 C14 N1 C13 -169.71(13) . . . . ?
C16 C14 N1 C13 66.68(17) . . . . ?
O1 C1 C2 C3 -177.69(15) . . . . ?
O1 C1 C10 C5 177.57(13) . . . . ?
O1 C1 C10 C9 0.4(2) . . . . ?
O1 C11 C12 C13 169.69(13) . . . . ?
O1 C11 C12 O2 -72.55(16) . . . . ?
O2 C12 C13 N1 63.49(17) . . . . ?
C17 C18 C19 C20 1.4(2) . . . . ?
C17 C21 N2 C20 1.6(2) . . . . ?
C18 C17 C21 N2 -0.7(2) . . . . ?
C18 C17 C22 O3 24.2(2) . . . . ?
C18 C17 C22 O4 -154.72(16) . . . . ?
C18 C19 C20 N2 -0.5(3) . . . . ?
C19 C20 N2 C21 -1.0(2) . . . . ?
C21 C17 C18 C19 -0.8(2) . . . . ?
C21 C17 C22 O3 -154.81(15) . . . . ?
C21 C17 C22 O4 26.3(2) . . . . ?
C22 C17 C18 C19 -179.89(14) . . . . ?
C22 C17 C21 N2 178.39(14) . . . . ?

_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 3.123
_oxdiff_exptl_absorpt_empirical_full_min 0.689
####################################################################### 
# 
# 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_AteNA
_database_code_depnum_ccdc_archive 'CCDC 2371677'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H23 N2 O3, C6 H4 N O2, C H4 O'
_chemical_formula_sum            'C21 H31 N3 O6'
_chemical_formula_weight         421.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.5713(2)
_cell_length_b                   9.0568(3)
_cell_length_c                   16.9380(5)
_cell_angle_alpha                77.3660(10)
_cell_angle_beta                 88.6140(10)
_cell_angle_gamma                76.5550(10)
_cell_volume                     1101.85(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0920 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.9535.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35708
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.370
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4259
_reflns_number_total             5440
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5440
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+1.8568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1388
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C21-O6 = C21A-O6A
 1.43 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C21 \\sim O6 \\sim C21A \\sim O6A: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
4. Others
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(O6A)=Sof(H6A)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(O6)=Sof(H6)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C11(H11A,H11B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19), C20(H20)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C21A(H21D,H21E,
 H21F)
5.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O6A(H6A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2218(3) 1.0663(2) 0.93928(11) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.3823(3) 1.1203(2) 0.89628(12) 0.0174(4) Uani 1 1 d . . . . .
H2A H 0.342770 1.231792 0.869560 0.021 Uiso 1 1 calc R U . . .
H2B H 0.478911 1.109769 0.936890 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4594(3) 1.0288(2) 0.83373(12) 0.0154(4) Uani 1 1 d . . . . .
C4 C 0.3991(3) 1.0788(2) 0.75312(12) 0.0158(4) Uani 1 1 d . . . . .
H4 H 0.309914 1.173524 0.737245 0.019 Uiso 1 1 calc R U . . .
C5 C 0.4661(3) 0.9933(2) 0.69505(12) 0.0151(4) Uani 1 1 d . . . . .
H5 H 0.422943 1.028774 0.640410 0.018 Uiso 1 1 calc R U . . .
C6 C 0.5974(3) 0.8553(2) 0.71878(12) 0.0154(4) Uani 1 1 d . . . . .
C7 C 0.6609(3) 0.8039(2) 0.79874(12) 0.0171(4) Uani 1 1 d . . . . .
H7 H 0.751024 0.709800 0.814465 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5924(3) 0.8902(2) 0.85533(12) 0.0177(4) Uani 1 1 d . . . . .
H8 H 0.636618 0.854604 0.909824 0.021 Uiso 1 1 calc R U . . .
C9 C 0.5967(3) 0.7921(2) 0.58814(11) 0.0172(4) Uani 1 1 d . . . . .
H9A H 0.611954 0.893508 0.556072 0.021 Uiso 1 1 calc R U . . .
H9B H 0.465397 0.794327 0.591060 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6966(3) 0.6602(2) 0.54977(11) 0.0158(4) Uani 1 1 d . . . . .
H10 H 0.829128 0.658662 0.548324 0.019 Uiso 1 1 calc R U . . .
C11 C 0.6702(3) 0.5047(2) 0.59925(12) 0.0168(4) Uani 1 1 d . . . . .
H11A H 0.682960 0.502033 0.657611 0.020 Uiso 1 1 calc R U . . .
H11B H 0.545983 0.494523 0.588774 0.020 Uiso 1 1 calc R U . . .
C12 C 0.7873(3) 0.2121(2) 0.62394(12) 0.0167(4) Uani 1 1 d . . . . .
H12 H 0.659806 0.203246 0.616540 0.020 Uiso 1 1 calc R U . . .
C13 C 0.9152(3) 0.0912(2) 0.58720(14) 0.0273(5) Uani 1 1 d . . . . .
H13A H 0.885120 0.109477 0.529386 0.041 Uiso 1 1 calc R U . . .
H13B H 0.902449 -0.012907 0.614362 0.041 Uiso 1 1 calc R U . . .
H13C H 1.040632 0.098901 0.594100 0.041 Uiso 1 1 calc R U . . .
C14 C 0.8284(3) 0.1885(3) 0.71373(12) 0.0232(4) Uani 1 1 d . . . . .
H14A H 0.952865 0.197639 0.721659 0.035 Uiso 1 1 calc R U . . .
H14B H 0.815754 0.084847 0.741774 0.035 Uiso 1 1 calc R U . . .
H14C H 0.743092 0.267725 0.735707 0.035 Uiso 1 1 calc R U . . .
N1 N 0.0789(3) 1.1766(2) 0.94953(11) 0.0225(4) Uani 1 1 d . . . . .
H1A H 0.075(4) 1.273(3) 0.9307(16) 0.029(7) Uiso 1 1 d . . . . .
H1B H -0.013(4) 1.147(3) 0.9759(16) 0.028(7) Uiso 1 1 d . . . . .
N2 N 0.8057(2) 0.37128(18) 0.57834(10) 0.0138(3) Uani 1 1 d . . . . .
H2C H 0.798(3) 0.372(3) 0.5221(16) 0.028(7) Uiso 1 1 d . . . . .
H2D H 0.918(3) 0.382(3) 0.5912(14) 0.020(6) Uiso 1 1 d . . . . .
O1 O 0.2289(2) 0.92563(17) 0.96431(9) 0.0239(3) Uani 1 1 d . . . . .
O2 O 0.67551(19) 0.76167(16) 0.66729(8) 0.0187(3) Uani 1 1 d . . . . .
O3 O 0.6258(2) 0.69373(17) 0.46975(9) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.713(4) 0.651(3) 0.4381(18) 0.042(8) Uiso 1 1 d . . . . .
C15 C 0.1565(2) 0.5551(2) 0.63708(11) 0.0151(4) Uani 1 1 d . . . . .
C16 C 0.1411(3) 0.5874(2) 0.72060(11) 0.0149(4) Uani 1 1 d . . . . .
C17 C 0.1781(3) 0.7221(2) 0.73640(12) 0.0191(4) Uani 1 1 d . . . . .
H17 H 0.208429 0.798698 0.693771 0.023 Uiso 1 1 calc R U . . .
C18 C 0.1700(3) 0.7424(2) 0.81517(13) 0.0218(4) Uani 1 1 d . . . . .
H18 H 0.193884 0.833515 0.827468 0.026 Uiso 1 1 calc R U . . .
C19 C 0.1267(3) 0.6281(2) 0.87549(12) 0.0213(4) Uani 1 1 d . . . . .
H19 H 0.123807 0.641957 0.929537 0.026 Uiso 1 1 calc R U . . .
C20 C 0.0955(3) 0.4815(2) 0.78520(12) 0.0184(4) Uani 1 1 d . . . . .
H20 H 0.067257 0.390768 0.774503 0.022 Uiso 1 1 calc R U . . .
N3 N 0.0886(3) 0.4986(2) 0.86184(10) 0.0226(4) Uani 1 1 d . . . . .
O4 O 0.2009(2) 0.65367(17) 0.58115(8) 0.0209(3) Uani 1 1 d . . . . .
O5 O 0.12697(19) 0.42611(16) 0.62897(8) 0.0173(3) Uani 1 1 d . . . . .
C21 C 0.6152(9) 0.4254(9) 0.9177(4) 0.0546(17) Uani 0.575(5) 1 d D U P A 1
H21A H 0.576867 0.539214 0.906691 0.082 Uiso 0.575(5) 1 calc R U P A 1
H21B H 0.575872 0.388030 0.872537 0.082 Uiso 0.575(5) 1 calc R U P A 1
H21C H 0.747817 0.393305 0.924068 0.082 Uiso 0.575(5) 1 calc R U P A 1
O6 O 0.5368(5) 0.3624(4) 0.9888(2) 0.0483(11) Uani 0.575(5) 1 d D U P A 1
H6 H 0.601838 0.274463 1.009807 0.072 Uiso 0.575(5) 1 calc R U P A 1
C21A C 0.6445(14) 0.4078(13) 0.8812(6) 0.057(2) Uani 0.425(5) 1 d D U P A 2
H21D H 0.706358 0.418999 0.829483 0.086 Uiso 0.425(5) 1 calc R U P A 2
H21E H 0.516812 0.463980 0.872398 0.086 Uiso 0.425(5) 1 calc R U P A 2
H21F H 0.651487 0.297388 0.904088 0.086 Uiso 0.425(5) 1 calc R U P A 2
O6A O 0.7302(6) 0.4707(6) 0.9360(3) 0.0426(13) Uani 0.425(5) 1 d D U P A 2
H6A H 0.651213 0.514185 0.964549 0.064 Uiso 0.425(5) 1 calc R U P A 2


_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
C1 C2 1.524(3) . ?
C1 N1 1.328(3) . ?
C1 O1 1.241(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.510(3) . ?
C3 C4 1.394(3) . ?
C3 C8 1.397(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 C7 1.391(3) . ?
C6 O2 1.376(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.522(3) . ?
C9 O2 1.425(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.527(3) . ?
C10 O3 1.413(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N2 1.494(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.517(3) . ?
C12 C14 1.518(3) . ?
C12 N2 1.515(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 H1A 0.86(3) . ?
N1 H1B 0.88(3) . ?
N2 H2C 0.95(3) . ?
N2 H2D 0.92(3) . ?
O3 H3 0.91(3) . ?
C15 C16 1.503(3) . ?
C15 O4 1.250(2) . ?
C15 O5 1.275(2) . ?
C16 C17 1.394(3) . ?
C16 C20 1.383(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9500 . ?
C19 N3 1.338(3) . ?
C20 H20 0.9500 . ?
C20 N3 1.339(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 O6 1.396(6) . ?
O6 H6 0.8400 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C21A O6A 1.428(7) . ?
O6A H6A 0.8400 . ?

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
N1 C1 C2 116.75(18) . . ?
O1 C1 C2 120.53(18) . . ?
O1 C1 N1 122.71(19) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.63(16) . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C4 C3 C2 121.16(17) . . ?
C4 C3 C8 118.03(18) . . ?
C8 C3 C2 120.80(18) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.73(18) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.71(18) . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.52(18) . . ?
O2 C6 C5 124.28(17) . . ?
O2 C6 C7 115.19(17) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.85(18) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.15(18) . . ?
C7 C8 H8 119.4 . . ?
H9A C9 H9B 108.7 . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
O2 C9 H9A 110.5 . . ?
O2 C9 H9B 110.5 . . ?
O2 C9 C10 106.09(15) . . ?
C9 C10 H10 109.3 . . ?
C9 C10 C11 109.97(16) . . ?
C11 C10 H10 109.3 . . ?
O3 C10 C9 106.46(15) . . ?
O3 C10 H10 109.3 . . ?
O3 C10 C11 112.51(16) . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N2 C11 C10 111.34(15) . . ?
N2 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C13 C12 H12 108.8 . . ?
C13 C12 C14 111.46(17) . . ?
C14 C12 H12 108.8 . . ?
N2 C12 H12 108.8 . . ?
N2 C12 C13 107.87(16) . . ?
N2 C12 C14 111.09(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 H1A 121.3(18) . . ?
C1 N1 H1B 117.8(17) . . ?
H1A N1 H1B 121(2) . . ?
C11 N2 C12 114.79(15) . . ?
C11 N2 H2C 111.3(15) . . ?
C11 N2 H2D 106.8(15) . . ?
C12 N2 H2C 106.4(15) . . ?
C12 N2 H2D 107.5(15) . . ?
H2C N2 H2D 110(2) . . ?
C6 O2 C9 118.24(15) . . ?
C10 O3 H3 108.9(18) . . ?
O4 C15 C16 118.29(17) . . ?
O4 C15 O5 124.66(18) . . ?
O5 C15 C16 117.03(17) . . ?
C17 C16 C15 121.42(17) . . ?
C20 C16 C15 120.95(17) . . ?
C20 C16 C17 117.60(18) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 118.98(19) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.79(19) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 118.3 . . ?
N3 C19 C18 123.43(19) . . ?
N3 C19 H19 118.3 . . ?
C16 C20 H20 117.9 . . ?
N3 C20 C16 124.22(19) . . ?
N3 C20 H20 117.9 . . ?
C19 N3 C20 116.96(18) . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 C21 H21A 109.5 . . ?
O6 C21 H21B 109.5 . . ?
O6 C21 H21C 109.5 . . ?
C21 O6 H6 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
O6A C21A H21D 109.5 . . ?
O6A C21A H21E 109.5 . . ?
O6A C21A H21F 109.5 . . ?
C21A O6A H6A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 92.2(2) . . . . ?
C1 C2 C3 C8 -87.1(2) . . . . ?
C2 C3 C4 C5 -178.45(18) . . . . ?
C2 C3 C8 C7 178.56(18) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C3 C8 C7 -0.8(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C4 C5 C6 O2 -179.23(17) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C5 C6 O2 C9 -11.4(3) . . . . ?
C6 C7 C8 C3 0.2(3) . . . . ?
C7 C6 O2 C9 169.62(17) . . . . ?
C8 C3 C4 C5 0.9(3) . . . . ?
C9 C10 C11 N2 -163.79(16) . . . . ?
C10 C9 O2 C6 -173.42(16) . . . . ?
C10 C11 N2 C12 -179.16(15) . . . . ?
C13 C12 N2 C11 171.90(17) . . . . ?
C14 C12 N2 C11 -65.7(2) . . . . ?
N1 C1 C2 C3 -135.82(19) . . . . ?
O1 C1 C2 C3 45.5(3) . . . . ?
O2 C6 C7 C8 179.43(17) . . . . ?
O2 C9 C10 C11 60.8(2) . . . . ?
O2 C9 C10 O3 -177.03(15) . . . . ?
O3 C10 C11 N2 77.7(2) . . . . ?
C15 C16 C17 C18 -177.01(18) . . . . ?
C15 C16 C20 N3 176.34(19) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C16 C20 N3 C19 0.8(3) . . . . ?
C17 C16 C20 N3 -1.5(3) . . . . ?
C17 C18 C19 N3 -1.2(3) . . . . ?
C18 C19 N3 C20 0.6(3) . . . . ?
C20 C16 C17 C18 0.8(3) . . . . ?
O4 C15 C16 C17 -1.1(3) . . . . ?
O4 C15 C16 C20 -178.87(18) . . . . ?
O5 C15 C16 C17 177.30(18) . . . . ?
O5 C15 C16 C20 -0.5(3) . . . . ?

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

data_MetINA
_database_code_depnum_ccdc_archive 'CCDC 2371673'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H26 N O3, C6 H4 N O2'
_chemical_formula_sum            'C21 H30 N2 O5'
_chemical_formula_weight         390.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.75330(10)
_cell_length_b                   8.87140(10)
_cell_length_c                   16.1407(2)
_cell_angle_alpha                86.5820(10)
_cell_angle_beta                 78.5720(10)
_cell_angle_gamma                78.7090(10)
_cell_volume                     1066.88(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    33285
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3020
_cell_measurement_theta_min      2.7700
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (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_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 3 2 0.1063
2 -5 1 0.1152
-1 -6 -1 0.0698
-5 -3 -2 0.1054
-4 3 -1 0.1255
1 6 0 0.0673
5 0 5 0.1342
0 0 10 0.0581
-5 0 -5 0.1165
1 0 -10 0.0463
-1 0 -10 0.0550
3 3 -5 0.0730
1 3 -8 0.0550
-4 -2 4 0.1092
0 -5 -5 0.0756
-5 -3 -4 0.0934
2 0 10 0.0929
0 -1 10 0.0617
-1 4 -8 0.0758
1 -5 -3 0.0830

_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            52647
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.507
_diffrn_reflns_theta_min         2.794
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 131.00   0.50    0.16    --   58.00  77.00 165.98  192
  2  ω     31.00 126.00   0.50    0.16    --   54.00  77.00 112.33  190
  3  ω     43.00 139.00   0.50    0.16    --   66.00  77.00 -32.47  192
  4  ω     85.00 133.00   0.50    0.16    --  107.75  77.00-150.00   96
  5  ω    143.00 172.00   0.50    0.16    --  107.75  77.00-150.00   58
  6  ω    126.00 152.00   0.50    0.16    --  107.75  77.00 -30.00   52
  7  ω     88.00 114.00   0.50    0.16    --  107.75  77.00 -30.00   52
  8  ω     85.00 111.00   0.50    0.16    --  107.75  77.00-120.00   52
  9  ω    114.00 177.00   0.50    0.16    --  107.75  77.00-120.00  126
 10  ω     85.00 110.00   0.50    0.16    --  107.75  77.00  90.00   50
 11  ω    119.00 176.00   0.50    0.16    --  107.75  77.00  90.00  114
 12  ω    129.00 177.00   0.50    0.16    --  107.75  77.00 120.00   96
 13  ω     86.00 112.00   0.50    0.16    --  107.75  77.00 120.00   52
 14  ω     85.00 149.00   0.50    0.16    --  107.75  77.00 150.00  128
 15  ω    141.00 167.00   0.50    0.16    --  107.75  77.00   0.00   52
 16  ω    125.00 178.00   0.50    0.16    --  107.75  77.00  30.00  106
 17  ω     85.00 120.00   0.50    0.16    --  107.75  77.00  30.00   70
 18  ω     86.00 117.00   0.50    0.16    --  107.75  77.00   0.00   62
 19  ω    136.00 162.00   0.50    0.16    --  107.75  77.00 -90.00   52
 20  ω     87.00 116.00   0.50    0.16    --  107.75  77.00-180.00   58
 21  ω    123.00 149.00   0.50    0.16    --  107.75  77.00-180.00   52
 22  ω     44.00 139.00   0.50    0.16    --   66.00  76.00 -67.69  190
 23  ω     87.00 113.00   0.50    0.16    --  107.75  77.00 -90.00   52
 24  ω     86.00 151.00   0.50    0.16    --  107.75  77.00 -60.00  130
 25  ω     48.00 143.00   0.50    0.16    --   70.00  76.00-100.87  190
 26  ω     28.00 122.00   0.50    0.16    --   50.00  76.00-122.75  188
 27  ω     44.00 139.00   0.50    0.16    --   66.00  76.00 -17.07  190
 28  ω     85.00 111.00   0.50    0.16    --  107.75  77.00  60.00   52
 29  ω    136.00 177.00   0.50    0.16    --  107.75  77.00  60.00   82
 30  ω     44.00 139.00   0.50    0.16    --   66.00  75.00 124.49  190
 31  ω     44.00 139.00   0.50    0.16    --   66.00  75.00 105.24  190
 32  ω     37.00 131.00   0.50    0.16    --   58.00  74.00  85.12  188
 33  ω     32.00 126.00   0.50    0.16    --   54.00  75.00  48.75  188
 34  ω     98.00 130.00   0.50    0.16    --  107.75  61.00  90.00   64
 35  ω     45.00 139.00   0.50    0.16    --   66.00  73.00 -47.56  188
 36  ω     93.00 162.00   0.50    0.16    --  107.75  61.00   0.00  138
 37  ω     33.00 126.00   0.50    0.16    --   54.00  73.00-125.69  186
 38  ω     37.00 131.00   0.50    0.16    --   58.00  74.00-164.65  188
 39  ω     93.00 118.00   0.50    0.16    --  107.75  61.00-180.00   50
 40  ω    132.00 160.00   0.50    0.16    --  107.75  61.00-150.00   56
 41  ω    127.00 172.00   0.50    0.16    --  107.75  61.00-180.00   90
 42  ω     94.00 127.00   0.50    0.16    --  107.75  61.00-150.00   66
 43  ω     91.00 118.00   0.50    0.16    --  107.75  61.00 -90.00   54
 44  ω    123.00 178.00   0.50    0.16    --  107.75  61.00 -90.00  110
 45  ω    105.00 155.00   0.50    0.16    --  107.75  61.00-120.00  100
 46  ω     93.00 164.00   0.50    0.16    --  107.75  61.00 -60.00  142
 47  ω     91.00 178.00   0.50    0.16    --  107.75  61.00 -30.00  174
 48  ω     91.00 139.00   0.50    0.16    --  107.75  61.00  30.00   96
 49  ω     91.00 133.00   0.50    0.16    --  107.75  61.00 150.00   84
 50  ω    138.00 173.00   0.50    0.16    --  107.75  61.00 150.00   70
 51  ω    147.00 172.00   0.50    0.16    --  107.75  61.00 120.00   50
 52  ω     93.00 143.00   0.50    0.16    --  107.75  61.00 120.00  100
 53  ω     99.00 124.00   0.50    0.16    --  107.75  45.00  90.00   50
 54  ω     97.00 130.00   0.50    0.16    --  107.75  45.00 120.00   66
 55  ω    104.00 130.00   0.50    0.16    --  107.75  30.00  90.00   52
 56  ω    153.00 178.00   0.50    0.16    --  107.75  30.00  90.00   50
 57  ω     33.00 120.00   0.50    0.16    --   47.77  57.00-150.00  174
 58  ω     85.00 173.00   0.50    0.16    --  107.75 140.00-151.00  176
 59  ω     93.00 178.00   0.50    0.16    --  107.75 129.00  35.00  170
 60  ω     70.00 101.00   0.50    0.16    --  107.75 -77.00 -60.00   62
 61  ω     77.00 105.00   0.50    0.16    --  107.75 -77.00   0.00   56
 62  ω     36.00  62.00   0.50    0.16    --  107.75 -77.00   0.00   52
 63  ω     37.00  72.00   0.50    0.16    --  107.75 -61.00  30.00   70
 64  ω     41.00  67.00   0.50    0.16    --  107.75 -61.00   0.00   52
 65  ω     43.00  73.00   0.50    0.16    --  107.75 -61.00-150.00   60
 66  ω     37.00 106.00   0.50    0.16    --  107.75 -77.00  60.00  138
 67  ω     68.00  98.00   0.50    0.16    --  107.75 -77.00  90.00   60
 68  ω     36.00  65.00   0.50    0.16    --  107.75 -61.00 120.00   58
 69  ω     45.00  70.00   0.50    0.16    --  107.75 -61.00 150.00   50
 70  ω     43.00 104.00   0.50    0.16    --   47.77-140.00 150.00  122
 71  ω     43.00 123.00   0.50    0.16    --  107.75-140.00 150.00  160
 72  ω     37.00 115.00   0.50    0.16    --  107.75-129.00 -36.00  156
 73  ω     45.00 111.00   0.50    0.16    --  107.75-125.00 -60.00  132
 74  ω     65.00  91.00   0.50    0.16    --  107.75-125.00 -90.00   52
 75  ω     36.00  61.00   0.50    0.16    --  107.75-125.00 -90.00   50
 76  ω     38.00  63.00   0.50    0.16    --  107.75-125.00-150.00   50
 77  ω     76.00 101.00   0.50    0.16    --  107.75-125.00-150.00   50
 78  ω     35.00  72.00   0.50    0.16    --  107.75 -94.00-180.00   74
 79  ω     49.00  98.00   0.50    0.16    --  107.75 -94.00-150.00   98
 80  ω     79.00 106.00   0.50    0.16    --  107.75 -94.00-180.00   54
 81  ω     51.00 105.00   0.50    0.16    --  107.75 -94.00 -60.00  108
 82  ω     36.00  96.00   0.50    0.16    --  107.75 -94.00 -30.00  120
 83  ω     37.00  98.00   0.50    0.16    --   47.77-129.00 -36.00  122
 84  ω     76.00 106.00   0.50    0.16    --  107.75 -94.00   0.00   60
 85  ω     37.00  63.00   0.50    0.16    --  107.75 -94.00   0.00   52
 86  ω     66.00  92.00   0.50    0.16    --  107.75 -94.00  90.00   52
 87  ω     52.00 106.00   0.50    0.16    --  107.75 -94.00 150.00  108
 88  ω     14.00  43.00   0.50    0.16    --   42.00  89.00 -96.59   58
 89  ω     13.00  43.00   0.50    0.16    --   42.00  90.00 -25.79   60
 90  ω    -21.00   7.00   0.50    0.16    --   14.00 103.00  83.70   56
 91  ω     17.00  43.00   0.50    0.16    --   46.00  90.00  63.76   52
 92  ω    -25.00  28.00   0.50    0.16    --  -47.77  19.00-150.00  106
 93  ω    -97.00 -21.00   0.50    0.16    --  -47.77 140.00-151.00  152
 94  ω    -83.00 -58.00   0.50    0.16    --  -86.25 140.00-151.00   50
 95  ω    -76.00 -51.00   0.50    0.16    --  -86.25 129.00  35.00   50
 96  ω    -88.00 -15.00   0.50    0.16    --  -47.77 129.00  35.00  146
 97  ω   -123.00 -35.00   0.50    0.16    --  -47.77 -19.00-180.00  176
 98  ω   -120.00 -25.00   0.50    0.16    --  -47.77 -77.00-120.00  190
 99  ω    -88.00 -63.00   0.50    0.16    --  -86.25 -77.00-120.00   50
100  ω    -88.00 -63.00   0.50    0.16    --  -86.25 -77.00 -60.00   50
101  ω   -122.00 -36.00   0.50    0.16    --  -47.77 -23.00  19.56  172
102  ω    -88.00 -63.00   0.50    0.16    --  -86.25 -77.00 120.00   50
103  ω    -92.00 -63.00   0.50    0.16    --  -86.25 -77.00  90.00   58
104  ω   -101.00 -64.00   0.50    0.16    --  -86.25 -76.00 160.08   74
105  ω   -159.00-121.00   0.50    0.16    --  -86.25 -77.00  90.00   76
106  ω    -90.00 -64.00   0.50    0.16    --  -86.25 -77.00  60.00   52
107  ω    -81.00 -55.00   0.50    0.16    --  -78.00 -76.00  52.20   52
108  ω    -91.00 -65.00   0.50    0.16    --  -86.25 -77.00  30.00   52
109  ω    -92.00 -66.00   0.50    0.16    --  -86.25 -74.00   6.36   52
110  ω    -82.00 -56.00   0.50    0.16    --  -78.00 -74.00  15.77   52
111  ω   -111.00 -64.00   0.50    0.16    --  -86.00 -74.00 -11.78   94
112  ω   -146.00 -52.00   0.50    0.16    --  -74.00 -74.00-146.20  188
113  ω    -93.00 -63.00   0.50    0.16    --  -86.25 -77.00-144.70   60
114  ω    -81.00 -55.00   0.50    0.16    --  -74.00 -71.00-118.92   52
115  ω    -94.00 -64.00   0.50    0.16    --  -86.25 -75.00-131.52   60
116  ω    -98.00 -66.00   0.50    0.16    --  -86.25 -70.00-111.23   64
117  ω    -80.00 -54.00   0.50    0.16    --  -74.00 -71.00 -54.86   52
118  ω   -101.00 -67.00   0.50    0.16    --  -86.25 -70.00 -78.20   68
119  ω   -101.00 -67.00   0.50    0.16    --  -86.25 -70.00 -90.56   68
120  ω   -104.00 -66.00   0.50    0.16    --  -86.25 -70.00 -50.44   76
121  ω   -139.00 -45.00   0.50    0.16    --  -66.00 -73.00  31.60  188
122  ω    -84.00 -58.00   0.50    0.16    --  -78.00 -70.00  33.79   52
123  ω    -92.00 -66.00   0.50    0.16    --  -86.25 -70.00  28.45   52
124  ω   -146.00 -53.00   0.50    0.16    --  -74.00 -72.00 112.84  186
125  ω   -143.00 -50.00   0.50    0.16    --  -70.00 -70.00 144.25  186
126  ω   -120.00 -67.00   0.50    0.16    --  -86.25 -69.00 174.90  106
127  ω    -86.00 -61.00   0.50    0.16    --  -78.00 -61.00 169.13   50
128  ω   -100.00 -74.00   0.50    0.16    --  -86.25 -61.00  60.00   52
129  ω   -135.00 -44.00   0.50    0.16    --  -62.00 -64.00  -9.25  182
130  ω    -94.00 -64.00   0.50    0.16    --  -78.00 -58.00 -16.49   60
131  ω   -146.00 -57.00   0.50    0.16    --  -74.00 -63.00-108.02  178
132  ω   -159.00 -71.00   0.50    0.16    --  -86.25-129.00 -36.00  176
133  ω   -120.00 -71.00   0.50    0.16    --  -47.77-129.00 -36.00   98
134  ω   -120.00 -63.00   0.50    0.16    --  -47.77-140.00 150.00  114
135  ω   -157.00 -63.00   0.50    0.16    --  -86.25-140.00 150.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4202
_reflns_number_total             4484
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.91704(17) -0.26318(16) 0.94886(8) 0.0332(3) Uani 1 1 d . . . . .
H1A H 1.033816 -0.279033 0.910557 0.050 Uiso 1 1 calc R U . . .
H1B H 0.923056 -0.332762 0.998118 0.050 Uiso 1 1 calc R U . . .
H1C H 0.885403 -0.156488 0.967507 0.050 Uiso 1 1 calc R U . . .
C2 C 0.61589(15) -0.28359(13) 0.96086(7) 0.0247(2) Uani 1 1 d . . . . .
H2A H 0.576415 -0.179477 0.984721 0.030 Uiso 1 1 calc R U . . .
H2B H 0.624654 -0.359230 1.008186 0.030 Uiso 1 1 calc R U . . .
C3 C 0.48177(15) -0.31607(12) 0.91069(7) 0.0224(2) Uani 1 1 d . . . . .
H3A H 0.530937 -0.414275 0.881083 0.027 Uiso 1 1 calc R U . . .
H3B H 0.370325 -0.328809 0.950389 0.027 Uiso 1 1 calc R U . . .
C4 C 0.43639(14) -0.19113(11) 0.84638(6) 0.0190(2) Uani 1 1 d . . . . .
C5 C 0.52000(14) -0.20017(11) 0.76175(7) 0.0188(2) Uani 1 1 d . . . . .
H5 H 0.609041 -0.287582 0.743377 0.023 Uiso 1 1 calc R U . . .
C6 C 0.47613(14) -0.08371(11) 0.70310(6) 0.0180(2) Uani 1 1 d . . . . .
H6 H 0.534903 -0.091465 0.645566 0.022 Uiso 1 1 calc R U . . .
C7 C 0.34521(14) 0.04366(11) 0.73021(6) 0.0185(2) Uani 1 1 d . . . . .
C8 C 0.26168(15) 0.05573(12) 0.81494(7) 0.0216(2) Uani 1 1 d . . . . .
H8 H 0.173659 0.143687 0.833459 0.026 Uiso 1 1 calc R U . . .
C9 C 0.30723(14) -0.06070(12) 0.87205(7) 0.0212(2) Uani 1 1 d . . . . .
H9 H 0.249682 -0.051809 0.929731 0.025 Uiso 1 1 calc R U . . .
C10 C 0.37821(14) 0.16854(11) 0.59304(6) 0.0192(2) Uani 1 1 d . . . . .
H10A H 0.370910 0.077379 0.562307 0.023 Uiso 1 1 calc R U . . .
H10B H 0.505969 0.171250 0.591172 0.023 Uiso 1 1 calc R U . . .
C11 C 0.28666(14) 0.31497(11) 0.55364(6) 0.0178(2) Uani 1 1 d . . . . .
H11 H 0.158338 0.309669 0.555378 0.021 Uiso 1 1 calc R U . . .
C12 C 0.29640(14) 0.45403(11) 0.60249(6) 0.0188(2) Uani 1 1 d . . . . .
H12A H 0.264755 0.431944 0.663889 0.023 Uiso 1 1 calc R U . . .
H12B H 0.420644 0.473108 0.590052 0.023 Uiso 1 1 calc R U . . .
C13 C 0.17514(14) 0.73790(11) 0.62553(6) 0.0189(2) Uani 1 1 d . . . . .
H13 H 0.301561 0.754197 0.616910 0.023 Uiso 1 1 calc R U . . .
C14 C 0.10456(16) 0.72198(13) 0.71969(7) 0.0245(2) Uani 1 1 d . . . . .
H14A H -0.019729 0.706794 0.729001 0.037 Uiso 1 1 calc R U . . .
H14B H 0.109558 0.815478 0.747838 0.037 Uiso 1 1 calc R U . . .
H14C H 0.178289 0.633385 0.743024 0.037 Uiso 1 1 calc R U . . .
C15 C 0.06452(17) 0.87360(12) 0.58621(7) 0.0282(3) Uani 1 1 d . . . . .
H15A H 0.114278 0.881409 0.525707 0.042 Uiso 1 1 calc R U . . .
H15B H 0.067529 0.968354 0.613710 0.042 Uiso 1 1 calc R U . . .
H15C H -0.059608 0.858583 0.593850 0.042 Uiso 1 1 calc R U . . .
N1 N 0.17243(12) 0.59448(9) 0.57971(5) 0.01642(18) Uani 1 1 d . . . . .
H1D H 0.058(2) 0.5745(15) 0.5921(8) 0.026(3) Uiso 1 1 d . . . . .
H1E H 0.1964(18) 0.6181(15) 0.5212(9) 0.026(3) Uiso 1 1 d . . . . .
O1 O 0.78552(10) -0.29382(9) 0.90613(5) 0.02390(17) Uani 1 1 d . . . . .
O2 O 0.28503(10) 0.16266(8) 0.67843(5) 0.02346(17) Uani 1 1 d . . . . .
O3 O 0.37693(10) 0.31946(9) 0.46832(5) 0.02165(17) Uani 1 1 d . . . . .
H3 H 0.300(2) 0.375(2) 0.4365(11) 0.047(5) Uiso 1 1 d . . . . .
C16 C 0.20056(13) 0.61735(11) 0.35713(6) 0.0174(2) Uani 1 1 d . . . . .
C17 C 0.20094(13) 0.69126(11) 0.27021(6) 0.0174(2) Uani 1 1 d . . . . .
C18 C 0.17036(14) 0.61280(12) 0.20406(6) 0.0194(2) Uani 1 1 d . . . . .
H18 H 0.144136 0.512204 0.212914 0.023 Uiso 1 1 calc R U . . .
C19 C 0.17888(14) 0.68417(12) 0.12496(7) 0.0220(2) Uani 1 1 d . . . . .
H19 H 0.159445 0.628603 0.080196 0.026 Uiso 1 1 calc R U . . .
C20 C 0.23989(15) 0.90124(12) 0.17199(7) 0.0242(2) Uani 1 1 d . . . . .
H20 H 0.263234 1.002562 0.161615 0.029 Uiso 1 1 calc R U . . .
C21 C 0.23585(14) 0.83909(12) 0.25322(7) 0.0213(2) Uani 1 1 d . . . . .
H21 H 0.256707 0.896893 0.296720 0.026 Uiso 1 1 calc R U . . .
N2 N 0.21271(13) 0.82640(11) 0.10740(6) 0.0244(2) Uani 1 1 d . . . . .
O4 O 0.23706(11) 0.69169(9) 0.41255(5) 0.02392(17) Uani 1 1 d . . . . .
O5 O 0.16494(10) 0.48258(8) 0.36797(4) 0.01932(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 O1 1.4138(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5161(16) . ?
C2 O1 1.4215(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5115(14) . ?
C4 C5 1.3909(14) . ?
C4 C9 1.3973(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3973(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3901(14) . ?
C7 C8 1.3931(14) . ?
C7 O2 1.3737(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.3834(15) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5215(14) . ?
C10 O2 1.4269(12) . ?
C11 H11 1.0000 . ?
C11 C12 1.5248(13) . ?
C11 O3 1.4179(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 N1 1.4927(13) . ?
C13 H13 1.0000 . ?
C13 C14 1.5181(14) . ?
C13 C15 1.5192(15) . ?
C13 N1 1.5150(12) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 H1D 0.919(15) . ?
N1 H1E 0.945(14) . ?
O3 H3 0.913(18) . ?
C16 C17 1.5125(14) . ?
C16 O4 1.2485(12) . ?
C16 O5 1.2734(12) . ?
C17 C18 1.3907(14) . ?
C17 C21 1.3910(14) . ?
C18 H18 0.9500 . ?
C18 C19 1.3863(15) . ?
C19 H19 0.9500 . ?
C19 N2 1.3412(14) . ?
C20 H20 0.9500 . ?
C20 C21 1.3886(15) . ?
C20 N2 1.3404(15) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
O1 C2 H2A 109.9 . . ?
O1 C2 H2B 109.9 . . ?
O1 C2 C3 108.71(9) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.55(9) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C5 C4 C3 122.32(9) . . ?
C5 C4 C9 118.16(9) . . ?
C9 C4 C3 119.52(9) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.56(9) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.01(9) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C8 120.26(9) . . ?
O2 C7 C6 124.69(9) . . ?
O2 C7 C8 115.04(9) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.84(10) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.16(10) . . ?
C8 C9 H9 119.4 . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
O2 C10 H10A 110.5 . . ?
O2 C10 H10B 110.5 . . ?
O2 C10 C11 106.10(8) . . ?
C10 C11 H11 109.4 . . ?
C10 C11 C12 109.89(8) . . ?
C12 C11 H11 109.4 . . ?
O3 C11 C10 106.16(8) . . ?
O3 C11 H11 109.4 . . ?
O3 C11 C12 112.43(8) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N1 C12 C11 111.57(8) . . ?
N1 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
C14 C13 H13 108.7 . . ?
C14 C13 C15 111.51(9) . . ?
C15 C13 H13 108.7 . . ?
N1 C13 H13 108.7 . . ?
N1 C13 C14 111.18(8) . . ?
N1 C13 C15 108.03(8) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 N1 C13 114.66(8) . . ?
C12 N1 H1D 107.8(8) . . ?
C12 N1 H1E 112.0(8) . . ?
C13 N1 H1D 108.4(8) . . ?
C13 N1 H1E 107.0(8) . . ?
H1D N1 H1E 106.6(12) . . ?
C1 O1 C2 111.68(9) . . ?
C7 O2 C10 118.42(8) . . ?
C11 O3 H3 109.0(11) . . ?
O4 C16 C17 117.89(9) . . ?
O4 C16 O5 124.83(9) . . ?
O5 C16 C17 117.27(9) . . ?
C18 C17 C16 121.27(9) . . ?
C18 C17 C21 117.68(9) . . ?
C21 C17 C16 121.04(9) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.74(9) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 117.8 . . ?
N2 C19 C18 124.39(10) . . ?
N2 C19 H19 117.8 . . ?
C21 C20 H20 118.1 . . ?
N2 C20 H20 118.1 . . ?
N2 C20 C21 123.72(10) . . ?
C17 C21 H21 120.4 . . ?
C20 C21 C17 119.28(10) . . ?
C20 C21 H21 120.4 . . ?
C20 N2 C19 116.19(9) . . ?

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
C2 C3 C4 C5 96.65(12) . . . . ?
C2 C3 C4 C9 -82.81(12) . . . . ?
C3 C2 O1 C1 179.42(9) . . . . ?
C3 C4 C5 C6 179.87(9) . . . . ?
C3 C4 C9 C8 -179.75(10) . . . . ?
C4 C5 C6 C7 -0.28(15) . . . . ?
C5 C4 C9 C8 0.77(15) . . . . ?
C5 C6 C7 C8 1.13(15) . . . . ?
C5 C6 C7 O2 -177.31(9) . . . . ?
C6 C7 C8 C9 -1.03(16) . . . . ?
C6 C7 O2 C10 -8.99(15) . . . . ?
C7 C8 C9 C4 0.06(16) . . . . ?
C8 C7 O2 C10 172.50(9) . . . . ?
C9 C4 C5 C6 -0.66(15) . . . . ?
C10 C11 C12 N1 -166.37(8) . . . . ?
C11 C10 O2 C7 -177.43(8) . . . . ?
C11 C12 N1 C13 -179.76(8) . . . . ?
C14 C13 N1 C12 -65.67(11) . . . . ?
C15 C13 N1 C12 171.67(9) . . . . ?
O1 C2 C3 C4 -69.31(11) . . . . ?
O2 C7 C8 C9 177.55(9) . . . . ?
O2 C10 C11 C12 59.27(10) . . . . ?
O2 C10 C11 O3 -178.91(8) . . . . ?
O3 C11 C12 N1 75.63(11) . . . . ?
C16 C17 C18 C19 -177.63(9) . . . . ?
C16 C17 C21 C20 178.22(9) . . . . ?
C17 C18 C19 N2 -0.91(16) . . . . ?
C18 C17 C21 C20 -0.40(15) . . . . ?
C18 C19 N2 C20 0.16(16) . . . . ?
C21 C17 C18 C19 0.99(15) . . . . ?
C21 C20 N2 C19 0.48(17) . . . . ?
N2 C20 C21 C17 -0.36(17) . . . . ?
O4 C16 C17 C18 176.79(10) . . . . ?
O4 C16 C17 C21 -1.78(15) . . . . ?
O5 C16 C17 C18 -2.40(14) . . . . ?
O5 C16 C17 C21 179.03(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MetNA
_database_code_depnum_ccdc_archive 'CCDC 2371672'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H26 N O3, C6 H4 N O2'
_chemical_formula_sum            'C21 H30 N2 O5'
_chemical_formula_weight         390.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.08110(10)
_cell_length_b                   9.22040(10)
_cell_length_c                   14.2988(2)
_cell_angle_alpha                99.0000(10)
_cell_angle_beta                 93.9190(10)
_cell_angle_gamma                98.5330(10)
_cell_volume                     1036.07(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21207
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3450
_cell_measurement_theta_min      3.1500
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (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_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -1 -1 0.0717
-5 0 2 0.0640
5 0 -5 0.0609
1 -1 -9 0.0404
-4 0 7 0.0546
5 0 -2 0.0676
-4 -4 3 0.0840
0 -1 -9 0.0374
0 1 9 0.0227
0 -6 3 0.0771
-1 6 -3 0.0860
-2 4 6 0.0617
-2 -4 -4 0.0736
-1 1 -9 0.0431
2 1 -9 0.0561
5 0 4 0.0625
2 -5 7 0.0730
-2 4 -6 0.0756
0 0 9 0.0169
0 -3 9 0.0373
4 -2 5 0.0690
2 2 -8 0.0678
-3 5 -3 0.0835
-1 4 6 0.0535
2 0 -9 0.0468

_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33458
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.829
_diffrn_reflns_theta_min         3.143
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -47.00   0.50    3.15    --  -47.79-165.00 -14.00  144
  2  ω    -83.00  -6.00   0.50    3.15    --  -47.79 116.00-138.00  154
  3  ω   -113.00 -33.00   0.50    3.15    --  -47.79 165.00   9.00  160
  4  ω     55.00 122.00   0.50    3.15    --   47.79-165.00 -14.00  134
  5  ω     28.00  91.00   0.50    3.15    --   47.79-116.00 133.00  126
  6  ω     69.00 120.00   0.50    3.15    --   47.79 165.00   9.00  102
  7  ω   -138.00 -47.00   0.50    3.15    --  -86.25-165.00 -14.00  182
  8  ω   -159.00 -79.00   0.50    3.15    --  -86.25-116.00 133.00  160
  9  ω    -83.00 -13.00   0.50    3.15    --  -86.25 116.00-138.00  140
 10  ω     69.00 155.00   0.50    3.15    --  107.75 165.00   9.00  172
 11  ω     35.00 109.00   0.50    3.15    --  107.75-116.00 133.00  148
 12  ω    101.00 178.00   0.50    3.15    --  107.75 116.00-138.00  154
 13  ω     55.00 139.00   0.50    3.15    --  107.75-165.00 -14.00  168
 14  ω    -25.00  28.00   0.50    3.15    --  -47.79  19.00-180.00  106
 15  ω   -119.00 -73.00   0.50    3.15    --  -47.79-125.00 -30.00   92
 16  ω    -25.00  28.00   0.50    3.15    --  -47.79  19.00 150.00  106
 17  ω   -119.00 -25.00   0.50    3.15    --  -47.79 -77.00  30.00  188
 18  ω   -158.00 -73.00   0.50    3.15    --  -86.25 -45.00-150.00  170
 19  ω     95.00 178.00   0.50    3.15    --  107.75 125.00 -30.00  166
 20  ω     35.00 112.00   0.50    3.15    --  107.75-125.00  90.00  154
 21  ω     35.00  73.00   0.50    3.15    --  107.75 -61.00 150.00   76
 22  ω     35.00 106.00   0.50    3.15    --  107.75 -94.00 120.00  142
 23  ω     35.00 107.00   0.50    3.15    --  107.75 -77.00  30.00  144
 24  ω     35.00 106.00   0.50    3.15    --  107.75 -94.00 -90.00  142
 25  ω     85.00 178.00   0.50    3.15    --  107.75  77.00-150.00  186
 26  ω     95.00 178.00   0.50    3.15    --  107.75  30.00 -60.00  166
 27  ω     35.00  73.00   0.50    3.15    --  107.75 -61.00 120.00   76
 28  ω     35.00 112.00   0.50    3.15    --  107.75-125.00-120.00  154
 29  ω     35.00 112.00   0.50    3.15    --  107.75-125.00  30.00  154
 30  ω     35.00 112.00   0.50    3.15    --  107.75-125.00 120.00  154
 31  ω     95.00 178.00   0.50    3.15    --  107.75 125.00 120.00  166
 32  ω     35.00 106.00   0.50    3.15    --  107.75 -94.00 -60.00  142
 33  ω     95.00 178.00   0.50    3.15    --  107.75 125.00   0.00  166
 34  ω     95.00 178.00   0.50    3.15    --  107.75  45.00 -30.00  166
 35  ω     35.00 106.00   0.50    3.15    --  107.75 -94.00  30.00  142
 36  ω     35.00 106.00   0.50    3.15    --  107.75 -94.00 -30.00  142
 37  ω     35.00 107.00   0.50    3.15    --  107.75 -77.00 120.00  144
 38  ω     95.00 178.00   0.50    3.15    --  107.75  30.00 -90.00  166
 39  ω     35.00 106.00   0.50    3.15    --  107.75 -94.00  90.00  142
 40  ω     95.00 178.00   0.50    3.15    --  107.75 125.00  60.00  166
 41  ω     95.00 178.00   0.50    3.15    --  107.75  45.00   0.00  166
 42  ω     35.00 106.00   0.50    3.15    --  107.75 -94.00-138.35  142
 43  ω     35.00  73.00   0.50    3.15    --  107.75 -61.00   0.00   76
 44  ω     95.00 178.00   0.50    3.15    --  107.75  45.00 150.00  166
 45  ω   -119.00 -25.00   0.50    3.15    --  -47.79 -77.00 150.00  188
 46  ω   -119.00 -25.00   0.50    3.15    --  -47.79 -77.00 120.00  188
 47  ω   -119.00 -25.00   0.50    3.15    --  -47.79 -77.00-150.00  188
 48  ω   -119.00 -33.00   0.50    3.15    --  -47.79 -57.00 -60.00  172
 49  ω   -119.00 -25.00   0.50    3.15    --  -47.79 -77.00 -90.00  188
 50  ω     36.00 121.00   0.50    3.15    --   47.79  38.00  90.00  170
 51  ω     25.00 121.00   0.50    3.15    --   47.79  77.00 -30.00  192
 52  ω     33.00 120.00   0.50    3.15    --   47.79  57.00 120.00  174
 53  ω   -159.00-108.00   0.50    3.15    --  -86.25 -71.00 120.81  102
 54  ω   -159.00 -63.00   0.50    3.15    --  -86.25 -77.00 -60.00  192
 55  ω   -159.00 -63.00   0.50    3.15    --  -86.25 -77.00-180.00  192
 56  ω   -159.00 -65.00   0.50    3.15    --  -86.25 -73.00  30.81  188
 57  ω   -159.00 -63.00   0.50    3.15    --  -86.25 -77.00  90.00  192
 58  ω     91.00 178.00   0.50    3.15    --  107.75  61.00  60.00  174
 59  ω     95.00 178.00   0.50    3.15    --  107.75  45.00-180.00  166
 60  ω     95.00 178.00   0.50    3.15    --  107.75  45.00 120.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3968
_reflns_number_total             4334
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.4267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1072
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38303(19) -0.20645(15) 0.13548(11) 0.0363(3) Uani 1 1 d . . . . .
H1A H 0.305595 -0.284296 0.092515 0.054 Uiso 1 1 calc R U . . .
H1B H 0.404526 -0.239754 0.196332 0.054 Uiso 1 1 calc R U . . .
H1C H 0.489124 -0.186279 0.106935 0.054 Uiso 1 1 calc R U . . .
C2 C 0.26304(17) -0.02939(14) 0.06437(9) 0.0298(3) Uani 1 1 d . . . . .
H2A H 0.187935 -0.111928 0.022226 0.036 Uiso 1 1 calc R U . . .
H2B H 0.363885 -0.001672 0.031408 0.036 Uiso 1 1 calc R U . . .
C3 C 0.17278(16) 0.10311(14) 0.08602(10) 0.0288(3) Uani 1 1 d . . . . .
H3A H 0.133339 0.131522 0.025377 0.035 Uiso 1 1 calc R U . . .
H3B H 0.072624 0.073746 0.119138 0.035 Uiso 1 1 calc R U . . .
C4 C 0.28173(15) 0.23667(13) 0.14685(9) 0.0249(3) Uani 1 1 d . . . . .
C5 C 0.28511(15) 0.26035(13) 0.24511(9) 0.0252(3) Uani 1 1 d . . . . .
H5 H 0.217861 0.190839 0.274975 0.030 Uiso 1 1 calc R U . . .
C6 C 0.38535(15) 0.38436(13) 0.30139(9) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.385492 0.399343 0.368663 0.030 Uiso 1 1 calc R U . . .
C7 C 0.48445(15) 0.48508(13) 0.25769(9) 0.0232(2) Uani 1 1 d . . . . .
C8 C 0.48447(16) 0.46220(13) 0.15917(9) 0.0249(3) Uani 1 1 d . . . . .
H8 H 0.553573 0.530607 0.129422 0.030 Uiso 1 1 calc R U . . .
C9 C 0.38336(16) 0.33930(14) 0.10450(9) 0.0258(3) Uani 1 1 d . . . . .
H9 H 0.383193 0.324648 0.037236 0.031 Uiso 1 1 calc R U . . .
C10 C 0.56858(16) 0.65490(13) 0.40352(9) 0.0248(3) Uani 1 1 d . . . . .
H10A H 0.600485 0.579451 0.440526 0.030 Uiso 1 1 calc R U . . .
H10B H 0.449912 0.664642 0.411926 0.030 Uiso 1 1 calc R U . . .
C11 C 0.68162(15) 0.80365(13) 0.43787(9) 0.0236(2) Uani 1 1 d . . . . .
H11 H 0.801339 0.791751 0.430728 0.028 Uiso 1 1 calc R U . . .
C12 C 0.63500(15) 0.92051(13) 0.38094(9) 0.0242(3) Uani 1 1 d . . . . .
H12A H 0.634001 0.882450 0.312181 0.029 Uiso 1 1 calc R U . . .
H12B H 0.520687 0.940164 0.393414 0.029 Uiso 1 1 calc R U . . .
C13 C 0.71623(16) 1.18897(13) 0.35880(9) 0.0263(3) Uani 1 1 d . . . . .
H13 H 0.602832 1.210195 0.375041 0.032 Uiso 1 1 calc R U . . .
C14 C 0.84579(19) 1.32564(15) 0.39882(11) 0.0353(3) Uani 1 1 d . . . . .
H14A H 0.844176 1.347772 0.468025 0.053 Uiso 1 1 calc R U . . .
H14B H 0.818938 1.410732 0.370777 0.053 Uiso 1 1 calc R U . . .
H14C H 0.957741 1.306506 0.383443 0.053 Uiso 1 1 calc R U . . .
C15 C 0.71276(18) 1.15108(15) 0.25171(10) 0.0316(3) Uani 1 1 d . . . . .
H15A H 0.822670 1.128403 0.234722 0.047 Uiso 1 1 calc R U . . .
H15B H 0.687104 1.235985 0.223078 0.047 Uiso 1 1 calc R U . . .
H15C H 0.626247 1.064312 0.228014 0.047 Uiso 1 1 calc R U . . .
N1 N 0.75707(13) 1.06180(11) 0.40706(8) 0.0231(2) Uani 1 1 d . . . . .
H1D H 0.859(2) 1.0414(18) 0.3929(11) 0.033(4) Uiso 1 1 d . . . . .
H1E H 0.765(2) 1.097(2) 0.4733(13) 0.042(5) Uiso 1 1 d . . . . .
O1 O 0.31074(11) -0.07527(10) 0.15083(7) 0.0296(2) Uani 1 1 d . . . . .
O2 O 0.58862(11) 0.61090(9) 0.30545(6) 0.0266(2) Uani 1 1 d . . . . .
O3 O 0.65946(12) 0.84089(10) 0.53535(6) 0.0289(2) Uani 1 1 d . . . . .
H3 H 0.762(3) 0.907(2) 0.5685(16) 0.069(6) Uiso 1 1 d . . . . .
C16 C 1.10845(15) 0.85215(14) 0.35093(9) 0.0244(3) Uani 1 1 d . . . . .
C17 C 1.02890(14) 0.74620(13) 0.26340(9) 0.0240(3) Uani 1 1 d . . . . .
C18 C 0.92873(16) 0.79252(14) 0.19452(9) 0.0269(3) Uani 1 1 d . . . . .
H18 H 0.908398 0.892358 0.205903 0.032 Uiso 1 1 calc R U . . .
C19 C 0.88954(17) 0.56581(16) 0.09935(10) 0.0332(3) Uani 1 1 d . . . . .
H19 H 0.842616 0.502549 0.041811 0.040 Uiso 1 1 calc R U . . .
C20 C 0.98517(17) 0.50774(15) 0.16364(11) 0.0343(3) Uani 1 1 d . . . . .
H20 H 1.001862 0.406970 0.150796 0.041 Uiso 1 1 calc R U . . .
C21 C 1.05611(16) 0.59934(14) 0.24711(10) 0.0295(3) Uani 1 1 d . . . . .
H21 H 1.122441 0.562425 0.292629 0.035 Uiso 1 1 calc R U . . .
N2 N 0.85914(14) 0.70614(13) 0.11342(8) 0.0319(3) Uani 1 1 d . . . . .
O4 O 1.06772(10) 0.98133(9) 0.36558(6) 0.0258(2) Uani 1 1 d . . . . .
O5 O 1.21110(12) 0.80684(10) 0.40472(7) 0.0315(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 O1 1.4130(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5158(18) . ?
C2 O1 1.4152(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5122(17) . ?
C4 C5 1.3855(18) . ?
C4 C9 1.3975(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3997(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3870(17) . ?
C7 C8 1.3913(17) . ?
C7 O2 1.3801(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.3870(17) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5208(16) . ?
C10 O2 1.4247(15) . ?
C11 H11 1.0000 . ?
C11 C12 1.5226(16) . ?
C11 O3 1.4127(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 N1 1.4919(15) . ?
C13 H13 1.0000 . ?
C13 C14 1.5208(18) . ?
C13 C15 1.5137(18) . ?
C13 N1 1.5155(15) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 H1D 0.901(18) . ?
N1 H1E 0.948(18) . ?
O3 H3 0.99(2) . ?
C16 C17 1.5018(17) . ?
C16 O4 1.2723(15) . ?
C16 O5 1.2530(15) . ?
C17 C18 1.3903(17) . ?
C17 C21 1.3903(17) . ?
C18 H18 0.9500 . ?
C18 N2 1.3357(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(2) . ?
C19 N2 1.3397(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3834(19) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
O1 C2 H2A 109.9 . . ?
O1 C2 H2B 109.9 . . ?
O1 C2 C3 108.86(11) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.23(10) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C5 C4 C3 121.51(11) . . ?
C5 C4 C9 118.27(11) . . ?
C9 C4 C3 120.22(12) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.51(11) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.15(12) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 120.20(11) . . ?
O2 C7 C6 124.48(11) . . ?
O2 C7 C8 115.32(11) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.85(11) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.02(12) . . ?
C8 C9 H9 119.5 . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
O2 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
O2 C10 C11 107.76(10) . . ?
C10 C11 H11 109.4 . . ?
C10 C11 C12 110.74(10) . . ?
C12 C11 H11 109.4 . . ?
O3 C11 C10 105.53(10) . . ?
O3 C11 H11 109.4 . . ?
O3 C11 C12 112.25(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
N1 C12 C11 110.91(10) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
C14 C13 H13 108.5 . . ?
C15 C13 H13 108.5 . . ?
C15 C13 C14 111.47(11) . . ?
C15 C13 N1 111.78(10) . . ?
N1 C13 H13 108.5 . . ?
N1 C13 C14 107.95(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 N1 C13 115.22(9) . . ?
C12 N1 H1D 107.6(10) . . ?
C12 N1 H1E 110.8(11) . . ?
C13 N1 H1D 109.4(10) . . ?
C13 N1 H1E 106.2(11) . . ?
H1D N1 H1E 107.4(15) . . ?
C1 O1 C2 111.94(10) . . ?
C7 O2 C10 117.18(9) . . ?
C11 O3 H3 109.4(13) . . ?
O4 C16 C17 118.17(10) . . ?
O5 C16 C17 117.43(11) . . ?
O5 C16 O4 124.40(12) . . ?
C18 C17 C16 121.14(11) . . ?
C18 C17 C21 117.57(12) . . ?
C21 C17 C16 121.26(11) . . ?
C17 C18 H18 117.8 . . ?
N2 C18 C17 124.42(12) . . ?
N2 C18 H18 117.8 . . ?
C20 C19 H19 118.1 . . ?
N2 C19 H19 118.1 . . ?
N2 C19 C20 123.81(13) . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.65(12) . . ?
C21 C20 H20 120.7 . . ?
C17 C21 H21 120.5 . . ?
C20 C21 C17 119.02(12) . . ?
C20 C21 H21 120.5 . . ?
C18 N2 C19 116.51(12) . . ?

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
C2 C3 C4 C5 -92.02(14) . . . . ?
C2 C3 C4 C9 87.45(14) . . . . ?
C3 C2 O1 C1 174.96(11) . . . . ?
C3 C4 C5 C6 -179.69(11) . . . . ?
C3 C4 C9 C8 -179.81(11) . . . . ?
C4 C5 C6 C7 -0.51(18) . . . . ?
C5 C4 C9 C8 -0.33(18) . . . . ?
C5 C6 C7 C8 -0.35(17) . . . . ?
C5 C6 C7 O2 -179.79(10) . . . . ?
C6 C7 C8 C9 0.84(17) . . . . ?
C6 C7 O2 C10 -12.60(16) . . . . ?
C7 C8 C9 C4 -0.50(18) . . . . ?
C8 C7 O2 C10 167.93(10) . . . . ?
C9 C4 C5 C6 0.84(17) . . . . ?
C10 C11 C12 N1 -173.80(10) . . . . ?
C11 C10 O2 C7 -173.88(9) . . . . ?
C11 C12 N1 C13 -176.41(10) . . . . ?
C14 C13 N1 C12 176.03(11) . . . . ?
C15 C13 N1 C12 -61.04(14) . . . . ?
O1 C2 C3 C4 62.00(14) . . . . ?
O2 C7 C8 C9 -179.66(10) . . . . ?
O2 C10 C11 C12 59.29(13) . . . . ?
O2 C10 C11 O3 -179.01(9) . . . . ?
O3 C11 C12 N1 68.53(13) . . . . ?
C16 C17 C18 N2 177.42(12) . . . . ?
C16 C17 C21 C20 -177.54(12) . . . . ?
C17 C18 N2 C19 0.2(2) . . . . ?
C18 C17 C21 C20 0.87(19) . . . . ?
C19 C20 C21 C17 0.0(2) . . . . ?
C20 C19 N2 C18 0.8(2) . . . . ?
C21 C17 C18 N2 -1.0(2) . . . . ?
N2 C19 C20 C21 -0.9(2) . . . . ?
O4 C16 C17 C18 7.34(18) . . . . ?
O4 C16 C17 C21 -174.31(11) . . . . ?
O5 C16 C17 C18 -172.59(12) . . . . ?
O5 C16 C17 C21 5.76(18) . . . . ?

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

data_LabINA
_database_code_depnum_ccdc_archive 'CCDC 2371679'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-07-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 N2 O3, C6 H4 N O2'
_chemical_formula_sum            'C25 H29 N3 O5'
_chemical_formula_weight         451.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8447(3)
_cell_length_b                   12.5695(6)
_cell_length_c                   12.6336(5)
_cell_angle_alpha                76.247(4)
_cell_angle_beta                 77.590(3)
_cell_angle_gamma                85.371(3)
_cell_volume                     1181.16(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15941
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.0440
_cell_measurement_theta_min      3.5730
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.74a (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_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 1 2 0.0581
-1 8 3 0.0558
-5 -3 -3 0.0710
1 -8 -3 0.0690
0 -2 7 0.0394
0 2 -7 0.0280
4 6 4 0.0714
-3 -7 -4 0.0779
4 -4 -1 0.0685
4 4 6 0.0623
-1 5 6 0.0499
-4 2 2 0.0652
-1 3 8 0.0363
-4 1 2 0.0594
1 3 8 0.0357
-1 -2 7 0.0376
-5 -1 0 0.0613
5 1 1 0.0529
0 -6 4 0.0561
-5 -2 -1 0.0581
0 -8 0 0.0638
-2 -8 -1 0.0663
0 -1 8 0.0337
0 5 7 0.0412

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.064
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33944
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.567
_diffrn_reflns_theta_min         3.622
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -97.00 -21.00   0.50    1.96    --  -47.51 141.00   9.00  152
  2  ω    -89.00 -15.00   0.50    1.96    --  -47.51 129.00-162.00  148
  3  ω   -120.00 -71.00   0.50    1.96    --  -47.51-129.00 123.00   98
  4  ω   -120.00 -63.00   0.50    1.96    --  -47.51-141.00 -48.00  114
  5  ω     43.00 105.00   0.50    1.96    --   47.51-141.00 -48.00  124
  6  ω     37.00  97.00   0.50    1.96    --   47.51-129.00 123.00  120
  7  ω   -159.00 -71.00   0.50    1.96    --  -86.25-129.00 123.00  176
  8  ω   -156.00 -63.00   0.50    1.96    --  -86.25-141.00 -48.00  186
  9  ω     84.00 173.00   0.50    1.96    --  107.75 141.00   9.00  178
 10  ω     43.00 124.00   0.50    1.96    --  107.75-141.00 -48.00  162
 11  ω     93.00 178.00   0.50    1.96    --  107.75 129.00-162.00  170
 12  ω     37.00 115.00   0.50    1.96    --  107.75-129.00 123.00  156
 13  ω    -41.00  25.00   0.50    1.96    --  -47.51  38.00  60.00  132
 14  ω   -120.00 -25.00   0.50    1.96    --  -47.51 -77.00 -60.00  190
 15  ω    -25.00  28.00   0.50    1.96    --  -47.51  19.00-180.00  106
 16  ω   -120.00 -73.00   0.50    1.96    --  -47.51-125.00 -30.00   94
 17  ω    -25.00  45.00   0.50    1.96    --   47.51 -38.00   0.00  140
 18  ω    -49.00 -14.00   0.50    1.96    --  -86.25  45.00   0.00   70
 19  ω    -49.00 -14.00   0.50    1.96    --  -86.25  45.00 -30.00   70
 20  ω    -89.00 -15.00   0.50    1.96    --  -86.25 129.00-162.00  148
 21  ω    -49.00 -14.00   0.50    1.96    --  -86.25  45.00-120.00   70
 22  ω    -49.00 -14.00   0.50    1.96    --  -86.25  45.00  60.00   70
 23  ω     95.00 178.00   0.50    1.96    --  107.75 125.00-180.00  166
 24  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00 -60.00  142
 25  ω     35.00 112.00   0.50    1.96    --  107.75-125.00-150.00  154
 26  ω     35.00  73.00   0.50    1.96    --  107.75 -61.00-180.00   76
 27  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00  30.00  142
 28  ω     95.00 178.00   0.50    1.96    --  107.75 125.00 150.00  166
 29  ω     35.00  73.00   0.50    1.96    --  107.75 -61.00 -30.00   76
 30  ω     95.00 178.00   0.50    1.96    --  107.75 125.00  60.00  166
 31  ω     94.00 178.00   0.50    1.96    --  107.75  15.00 -60.00  168
 32  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00 120.00  142
 33  ω     35.00 112.00   0.50    1.96    --  107.75-125.00-180.00  154
 34  ω     35.00  73.00   0.50    1.96    --  107.75 -61.00 150.00   76
 35  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00-120.00  142
 36  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00   0.00  142
 37  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00 -90.00  142
 38  ω     35.00  73.00   0.50    1.96    --  107.75 -61.00-120.00   76
 39  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00 -30.00  142
 40  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00-150.00  142
 41  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00  60.00  142
 42  ω     95.00 178.00   0.50    1.96    --  107.75  30.00   0.00  166
 43  ω     95.00 178.00   0.50    1.96    --  107.75  30.00-180.00  166
 44  ω     35.00 106.00   0.50    1.96    --  107.75 -94.00  90.00  142
 45  ω     94.00 178.00   0.50    1.96    --  107.75  15.00  90.00  168
 46  ω     35.00  73.00   0.50    1.96    --  107.75 -61.00  90.00   76
 47  ω     35.00 107.00   0.50    1.96    --  107.75 -77.00 -30.00  144
 48  ω     95.00 178.00   0.50    1.96    --  107.75  30.00 -30.00  166
 49  ω   -120.00 -34.00   0.50    1.96    --  -47.51 -38.00  30.00  172
 50  ω    -25.00  28.00   0.50    1.96    --  -47.51  19.00  30.00  106
 51  ω     25.00 120.00   0.50    1.96    --   47.51  77.00   0.00  190
 52  ω     25.00 120.00   0.50    1.96    --   47.51  77.00 120.00  190
 53  ω     33.00 120.00   0.50    1.96    --   47.51  57.00  60.00  174
 54  ω     33.00 120.00   0.50    1.96    --   47.51  57.00 -90.00  174
 55  ω     25.00 120.00   0.50    1.96    --   47.51  77.00 -90.00  190
 56  ω     25.00 120.00   0.50    1.96    --   47.51  77.00 -60.00  190
 57  ω     25.00 120.00   0.50    1.96    --   47.51  77.00-180.00  190
 58  ω     35.00 121.00   0.50    1.96    --   47.51  38.00-150.00  172
 59  ω     25.00 120.00   0.50    1.96    --   47.51  77.00  90.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3890
_reflns_number_total             4927
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4927
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.6614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          ?
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained planarity
 C21, C25B, C24B, N3B, C23B, C22
 with sigma of 0.1
 C25A, C24A, C21, C23A, C22, N3A
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C21 \\sim C22 \\sim N3B \\sim C23B \\sim C25B \\sim C24B \\sim C25A \\sim C24A
\\sim N3A \\sim C23A: within 2A with sigma of 0.02 and sigma for terminal atoms
of 0.04 within 2A
C13 \\sim C14A \\sim C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A \\sim
C14B \\sim C15B \\sim C16A \\sim C17B \\sim C18B \\sim C19B: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C21, C22, N3B, C23B, C25B, C24B, C25A, C24A, N3A, C23A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C13, C14A, C15A, C18A, C17A, C19A, C16A, C14B, C19B, C18B, C16A, C15B, C17B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H22A)=Sof(C23B)=Sof(H23B)=Sof(C24B)=Sof(H24B)=Sof(C25B)=Sof(H25B)=
 Sof(N3B)=1-FVAR(1)
 Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=Sof(N3A)=Sof(C23A)=Sof(H23A)=Sof(H22)=
 FVAR(1)
 Sof(H13C)=Sof(H13D)=Sof(C14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=
 Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=1-FVAR(2)
 Sof(H13A)=Sof(H13B)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=FVAR(2)
 Fixed Sof: H8A(0.5) H8B(0.5) O3A(0.5) H3A(0.5) O3B(0.5) H3B(0.5)
6.a Ternary CH refined with riding coordinates:
 C8(H8A), C8(H8B), C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C13(H13C,H13D), N2(H2A,H2B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A),
 C19A(H19A), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B),
 C25A(H25A), C24A(H24A), C23A(H23A), C22(H22), C22(H22A), C23B(H23B),
 C24B(H24B), C25B(H25B)
6.d Fitted hexagon refined as free rotating group:
 C14A(C15A,C16A,C17A,C18A,C19A), C14B(C15B,C16B,C17B,C18B,C19B), C25A(C24A,N3A,
 C23A,C22,C21)
6.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
6.f Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
6.g Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3A(H3A), O3B(H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5168(3) 0.15511(17) 0.93067(16) 0.0377(5) Uani 1 1 d . . . . .
C2 C 0.6789(3) 0.19779(19) 0.87860(17) 0.0424(5) Uani 1 1 d . . . . .
H2 H 0.753269 0.214913 0.922074 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7340(3) 0.21580(17) 0.76480(16) 0.0381(5) Uani 1 1 d . . . . .
H3 H 0.846199 0.244479 0.731106 0.046 Uiso 1 1 calc R U . . .
C4 C 0.6277(3) 0.19258(15) 0.69852(16) 0.0338(4) Uani 1 1 d . . . . .
C5 C 0.4648(2) 0.15168(15) 0.75022(15) 0.0320(4) Uani 1 1 d . . . . .
H5 H 0.390378 0.136366 0.705833 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4056(2) 0.13205(15) 0.86561(15) 0.0330(4) Uani 1 1 d . . . . .
C7 C 0.2314(3) 0.08630(16) 0.92080(16) 0.0349(4) Uani 1 1 d . . . . .
C8 C 0.6885(3) 0.20904(16) 0.57370(16) 0.0346(4) Uani 1 1 d . . . . .
H8A H 0.593302 0.252212 0.539569 0.042 Uiso 0.5 1 calc R U P A 1
H8B H 0.810095 0.236004 0.556565 0.042 Uiso 0.5 1 calc R U P B 2
C9 C 0.7044(3) 0.10014(16) 0.54095(16) 0.0352(4) Uani 1 1 d . . . . .
H9A H 0.755479 0.044830 0.596489 0.042 Uiso 1 1 calc R U . . .
H9B H 0.586135 0.076614 0.542841 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7586(3) 0.17922(16) 0.32906(16) 0.0344(4) Uani 1 1 d . . . . .
H10 H 0.737059 0.254371 0.343821 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5918(3) 0.14060(19) 0.31021(19) 0.0457(5) Uani 1 1 d . . . . .
H11A H 0.613544 0.068525 0.291957 0.069 Uiso 1 1 calc R U . . .
H11B H 0.552859 0.193054 0.248571 0.069 Uiso 1 1 calc R U . . .
H11C H 0.501234 0.135227 0.377920 0.069 Uiso 1 1 calc R U . . .
C12 C 0.9119(3) 0.18167(16) 0.23146(16) 0.0364(4) Uani 1 1 d . . . . .
H12A H 0.938112 0.106235 0.220388 0.044 Uiso 1 1 calc R U . . .
H12B H 1.015939 0.206547 0.250285 0.044 Uiso 1 1 calc R U . . .
C13 C 0.8800(3) 0.25621(19) 0.12253(18) 0.0491(5) Uani 1 1 d . U . . .
H13A H 0.771505 0.235514 0.105439 0.059 Uiso 0.595(8) 1 calc R U P C 1
H13B H 0.978098 0.247044 0.061044 0.059 Uiso 0.595(8) 1 calc R U P C 1
H13C H 0.989631 0.256740 0.066318 0.059 Uiso 0.405(8) 1 calc R U P C 2
H13D H 0.791203 0.221915 0.097420 0.059 Uiso 0.405(8) 1 calc R U P C 2
C14A C 0.8629(6) 0.3816(3) 0.1323(5) 0.0533(11) Uani 0.595(8) 1 d G U P C 1
C15A C 1.0078(6) 0.4336(3) 0.1404(5) 0.0547(11) Uani 0.595(8) 1 d G U P C 1
H15A H 1.115291 0.393794 0.144322 0.066 Uiso 0.595(8) 1 calc R U P C 1
C16A C 0.9954(7) 0.5440(3) 0.1428(4) 0.0699(13) Uani 0.595(8) 1 d G U P C 1
H16A H 1.094354 0.579605 0.148362 0.084 Uiso 0.595(8) 1 calc R U P C 1
C17A C 0.8381(8) 0.6023(3) 0.1371(4) 0.0812(16) Uani 0.595(8) 1 d G U P C 1
H17A H 0.829563 0.677769 0.138736 0.097 Uiso 0.595(8) 1 calc R U P C 1
C18A C 0.6932(6) 0.5503(3) 0.1290(4) 0.0898(17) Uani 0.595(8) 1 d G U P C 1
H18A H 0.585707 0.590122 0.125068 0.108 Uiso 0.595(8) 1 calc R U P C 1
C19A C 0.7056(5) 0.4399(3) 0.1266(4) 0.0739(14) Uani 0.595(8) 1 d G U P C 1
H19A H 0.606641 0.404310 0.121028 0.089 Uiso 0.595(8) 1 calc R U P C 1
C14B C 0.8252(10) 0.3660(4) 0.1209(7) 0.0579(15) Uani 0.405(8) 1 d G U P C 2
C15B C 0.9372(10) 0.4348(5) 0.1426(7) 0.0638(16) Uani 0.405(8) 1 d G U P C 2
H15B H 1.047793 0.407401 0.158086 0.077 Uiso 0.405(8) 1 calc R U P C 2
C16B C 0.8873(13) 0.5436(5) 0.1416(6) 0.096(4) Uani 0.405(8) 1 d G . P C 2
H16B H 0.963812 0.590603 0.156459 0.116 Uiso 0.405(8) 1 calc R U P C 2
C17B C 0.7255(13) 0.5837(4) 0.1190(6) 0.088(2) Uani 0.405(8) 1 d G U P C 2
H17B H 0.691361 0.658059 0.118291 0.105 Uiso 0.405(8) 1 calc R U P C 2
C18B C 0.6135(10) 0.5149(6) 0.0972(6) 0.089(2) Uani 0.405(8) 1 d G U P C 2
H18B H 0.502888 0.542316 0.081750 0.106 Uiso 0.405(8) 1 calc R U P C 2
C19B C 0.6634(9) 0.4061(5) 0.0982(6) 0.0723(17) Uani 0.405(8) 1 d G U P C 2
H19B H 0.586866 0.359113 0.083377 0.087 Uiso 0.405(8) 1 calc R U P C 2
O1 O 0.4720(2) 0.13789(14) 1.04271(11) 0.0479(4) Uani 1 1 d . . . . .
H1 H 0.375396 0.107262 1.065120 0.072 Uiso 1 1 calc R U . . .
O2 O 0.18990(19) 0.05998(12) 1.02496(11) 0.0413(4) Uani 1 1 d . . . . .
N1 N 0.1202(2) 0.07496(14) 0.85848(14) 0.0379(4) Uani 1 1 d . . . . .
H1A H 0.016279 0.048744 0.890253 0.045 Uiso 1 1 calc R U . . .
H1B H 0.150626 0.093673 0.785462 0.045 Uiso 1 1 calc R U . . .
N2 N 0.8143(2) 0.10289(12) 0.42801(12) 0.0317(4) Uani 1 1 d . . . . .
H2A H 0.821251 0.033754 0.416522 0.038 Uiso 1 1 calc R U . . .
H2B H 0.924167 0.120453 0.429025 0.038 Uiso 1 1 calc R U . . .
O3A O 0.8339(3) 0.2667(2) 0.5305(2) 0.0305(5) Uani 0.5 1 d . . P D 1
H3A H 0.813722 0.331481 0.537861 0.046 Uiso 0.5 1 calc R U P D 1
O3B O 0.5974(4) 0.2867(2) 0.5146(2) 0.0412(7) Uani 0.5 1 d . . P D 2
H3B H 0.621655 0.348592 0.520518 0.062 Uiso 0.5 1 calc R U P D 2
C20 C 0.1729(2) 0.17269(15) 0.51977(16) 0.0317(4) Uani 1 1 d . . . E 2
C25A C 0.2184(9) 0.3578(3) 0.39622(14) 0.053(2) Uani 0.39(2) 1 d G U P E 1
H25A H 0.221561 0.325023 0.335366 0.063 Uiso 0.39(2) 1 calc R U P E 1
C24A C 0.2269(17) 0.4709(3) 0.3783(3) 0.054(2) Uani 0.39(2) 1 d G U P E 1
H24A H 0.235978 0.515391 0.305275 0.065 Uiso 0.39(2) 1 calc R U P E 1
N3A N 0.2222(16) 0.51893(15) 0.4674(4) 0.0435(17) Uani 0.39(2) 1 d G U P E 1
C23A C 0.2090(9) 0.45386(17) 0.5743(3) 0.0427(17) Uani 0.39(2) 1 d G U P E 1
H23A H 0.205808 0.486671 0.635128 0.051 Uiso 0.39(2) 1 calc R U P E 1
C22 C 0.2004(3) 0.34078(15) 0.59216(13) 0.0391(4) Uani 1 1 d G U . . .
H22 H 0.191391 0.296304 0.665221 0.047 Uiso 0.39(2) 1 calc R U P E 1
H22A H 0.168474 0.300251 0.666813 0.047 Uiso 0.61(2) 1 calc R U P E 2
C21 C 0.2051(3) 0.29276(14) 0.50312(14) 0.0365(4) Uani 1 1 d G U . . .
C23B C 0.2442(12) 0.4502(4) 0.5682(5) 0.0532(12) Uani 0.61(2) 1 d . U P E 2
H23B H 0.236784 0.482664 0.629728 0.064 Uiso 0.61(2) 1 calc R U P E 2
C24B C 0.2983(16) 0.4658(4) 0.3861(5) 0.061(2) Uani 0.61(2) 1 d . U P E 2
H24B H 0.331775 0.509158 0.312743 0.073 Uiso 0.61(2) 1 calc R U P E 2
C25B C 0.2575(12) 0.3590(4) 0.3974(4) 0.0527(12) Uani 0.61(2) 1 d . U P E 2
H25B H 0.265046 0.330410 0.333271 0.063 Uiso 0.61(2) 1 calc R U P E 2
N3B N 0.2944(18) 0.5126(4) 0.4693(4) 0.0606(18) Uani 0.61(2) 1 d . U P E 2
O4 O 0.14923(18) 0.14109(11) 0.43708(11) 0.0371(3) Uani 1 1 d . . . . .
O5 O 0.17397(18) 0.11102(11) 0.61429(11) 0.0366(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.386(3) . ?
C1 C6 1.408(3) . ?
C1 O1 1.352(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 C5 1.383(3) . ?
C4 C8 1.515(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(3) . ?
C6 C7 1.487(3) . ?
C7 O2 1.254(2) . ?
C7 N1 1.330(3) . ?
C8 H8A 1.0000 . ?
C8 H8B 1.0000 . ?
C8 C9 1.510(3) . ?
C8 O3A 1.343(3) . ?
C8 O3B 1.338(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 N2 1.494(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.515(3) . ?
C10 C12 1.522(3) . ?
C10 N2 1.507(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.527(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C13 C14A 1.602(4) . ?
C13 C14B 1.409(5) . ?
C14A C15A 1.3900 . ?
C14A C19A 1.3900 . ?
C15A H15A 0.9500 . ?
C15A C16A 1.3900 . ?
C16A H16A 0.9500 . ?
C16A C17A 1.3900 . ?
C17A H17A 0.9500 . ?
C17A C18A 1.3900 . ?
C18A H18A 0.9500 . ?
C18A C19A 1.3900 . ?
C19A H19A 0.9500 . ?
C14B C15B 1.3900 . ?
C14B C19B 1.3900 . ?
C15B H15B 0.9500 . ?
C15B C16B 1.3900 . ?
C16B H16B 0.9500 . ?
C16B C17B 1.3900 . ?
C17B H17B 0.9500 . ?
C17B C18B 1.3900 . ?
C18B H18B 0.9500 . ?
C18B C19B 1.3900 . ?
C19B H19B 0.9500 . ?
O1 H1 0.8400 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
O3A H3A 0.8400 . ?
O3B H3B 0.8400 . ?
C20 C21 1.508(2) . ?
C20 O4 1.255(2) . ?
C20 O5 1.261(2) . ?
C25A H25A 0.9500 . ?
C25A C24A 1.3900 . ?
C25A C21 1.3900 . ?
C24A H24A 0.9500 . ?
C24A N3A 1.3900 . ?
N3A C23A 1.3900 . ?
C23A H23A 0.9500 . ?
C23A C22 1.3900 . ?
C22 H22 0.9500 . ?
C22 H22A 0.9500 . ?
C22 C21 1.3900 . ?
C22 C23B 1.391(5) . ?
C21 C25B 1.392(5) . ?
C23B H23B 0.9500 . ?
C23B N3B 1.305(6) . ?
C24B H24B 0.9500 . ?
C24B C25B 1.373(6) . ?
C24B N3B 1.315(6) . ?
C25B H25B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.20(18) . . ?
O1 C1 C2 118.05(18) . . ?
O1 C1 C6 122.75(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.10(19) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.94(19) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C8 121.53(18) . . ?
C5 C4 C3 118.00(18) . . ?
C5 C4 C8 120.46(17) . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.33(18) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C7 119.56(17) . . ?
C5 C6 C1 118.42(18) . . ?
C5 C6 C7 122.01(17) . . ?
O2 C7 C6 120.03(18) . . ?
O2 C7 N1 120.74(18) . . ?
N1 C7 C6 119.23(17) . . ?
C4 C8 H8A 106.5 . . ?
C4 C8 H8B 105.8 . . ?
C9 C8 C4 110.11(15) . . ?
C9 C8 H8A 106.5 . . ?
C9 C8 H8B 105.8 . . ?
O3A C8 C4 115.02(19) . . ?
O3A C8 H8A 106.5 . . ?
O3A C8 C9 111.79(18) . . ?
O3B C8 C4 114.10(19) . . ?
O3B C8 H8B 105.8 . . ?
O3B C8 C9 114.4(2) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N2 C9 C8 113.55(15) . . ?
N2 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C11 C10 H10 109.0 . . ?
C11 C10 C12 113.48(17) . . ?
C12 C10 H10 109.0 . . ?
N2 C10 H10 109.0 . . ?
N2 C10 C11 110.06(16) . . ?
N2 C10 C12 106.20(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 108.8 . . ?
C10 C12 H12B 108.8 . . ?
C10 C12 C13 113.88(17) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C12 C13 H13C 107.6 . . ?
C12 C13 H13D 107.6 . . ?
C12 C13 C14A 110.2(3) . . ?
H13A C13 H13B 108.1 . . ?
H13C C13 H13D 107.0 . . ?
C14A C13 H13A 109.6 . . ?
C14A C13 H13B 109.6 . . ?
C14B C13 C12 118.9(4) . . ?
C14B C13 H13C 107.6 . . ?
C14B C13 H13D 107.6 . . ?
C15A C14A C13 120.0(3) . . ?
C15A C14A C19A 120.0 . . ?
C19A C14A C13 119.9(3) . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C17A C18A C19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C15B C14B C13 118.5(4) . . ?
C15B C14B C19B 120.0 . . ?
C19B C14B C13 121.5(4) . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C19B C18B C17B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C14B C19B H19B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C1 O1 H1 109.5 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 N2 C10 118.43(15) . . ?
C9 N2 H2A 107.7 . . ?
C9 N2 H2B 107.7 . . ?
C10 N2 H2A 107.7 . . ?
C10 N2 H2B 107.7 . . ?
H2A N2 H2B 107.1 . . ?
C8 O3A H3A 109.5 . . ?
C8 O3B H3B 109.5 . . ?
O4 C20 C21 117.05(16) . . ?
O4 C20 O5 124.63(18) . . ?
O5 C20 C21 118.31(16) . . ?
C24A C25A H25A 120.0 . . ?
C24A C25A C21 120.0 . . ?
C21 C25A H25A 120.0 . . ?
C25A C24A H24A 120.0 . . ?
C25A C24A N3A 120.0 . . ?
N3A C24A H24A 120.0 . . ?
C24A N3A C23A 120.0 . . ?
N3A C23A H23A 120.0 . . ?
C22 C23A N3A 120.0 . . ?
C22 C23A H23A 120.0 . . ?
C23A C22 H22 120.0 . . ?
C23A C22 C21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 H22A 121.1 . . ?
C21 C22 C23B 117.7(3) . . ?
C23B C22 H22A 121.1 . . ?
C22 C21 C20 121.95(15) . . ?
C22 C21 C25A 120.0 . . ?
C22 C21 C25B 116.3(3) . . ?
C25B C21 C20 121.5(3) . . ?
C22 C23B H23B 116.8 . . ?
N3B C23B C22 126.3(5) . . ?
N3B C23B H23B 116.8 . . ?
C25B C24B H24B 117.6 . . ?
N3B C24B H24B 117.6 . . ?
N3B C24B C25B 124.8(4) . . ?
C21 C25B H25B 120.2 . . ?
C24B C25B C21 119.7(4) . . ?
C24B C25B H25B 120.2 . . ?
C23B N3B C24B 115.1(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
O1 H1 O2 0.84 1.82 2.564(2) 146.0 . yes
N2 H2A O5 0.91 1.95 2.854(2) 176.4 2_656 yes
N2 H2B O4 0.91 1.83 2.740(2) 174.2 1_655 yes
O3A H3A N3A 0.84 1.87 2.70(2) 172.0 2_666 yes
O3B H3B N3B 0.84 1.96 2.791(6) 173.6 2_666 yes

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
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C6 C7 O2 -5.9(3) . . . . ?
C1 C6 C7 N1 173.33(18) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -179.96(18) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C2 C3 C4 C8 -178.31(19) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C8 C9 114.8(2) . . . . ?
C3 C4 C8 O3A -12.6(3) . . . . ?
C3 C4 C8 O3B -114.9(2) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -178.96(17) . . . . ?
C4 C8 C9 N2 -161.84(16) . . . . ?
C5 C4 C8 C9 -63.9(2) . . . . ?
C5 C4 C8 O3A 168.7(2) . . . . ?
C5 C4 C8 O3B 66.4(3) . . . . ?
C5 C6 C7 O2 173.10(17) . . . . ?
C5 C6 C7 N1 -7.6(3) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C8 C4 C5 C6 178.00(17) . . . . ?
C8 C9 N2 C10 -60.3(2) . . . . ?
C10 C12 C13 C14A 66.2(3) . . . . ?
C10 C12 C13 C14B 53.0(5) . . . . ?
C11 C10 C12 C13 59.3(2) . . . . ?
C11 C10 N2 C9 -68.3(2) . . . . ?
C12 C10 N2 C9 168.52(16) . . . . ?
C12 C13 C14A C15A 68.3(3) . . . . ?
C12 C13 C14A C19A -115.2(3) . . . . ?
C12 C13 C14B C15B 63.6(5) . . . . ?
C12 C13 C14B C19B -116.4(4) . . . . ?
C13 C14A C15A C16A 176.5(4) . . . . ?
C13 C14A C19A C18A -176.5(4) . . . . ?
C13 C14B C15B C16B 180.0(7) . . . . ?
C13 C14B C19B C18B -180.0(7) . . . . ?
C14A C15A C16A C17A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C15A C16A C17A C18A 0.0 . . . . ?
C16A C17A C18A C19A 0.0 . . . . ?
C17A C18A C19A C14A 0.0 . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?
C14B C15B C16B C17B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
C15B C16B C17B C18B 0.0 . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C17B C18B C19B C14B 0.0 . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
O1 C1 C2 C3 178.99(19) . . . . ?
O1 C1 C6 C5 -179.34(18) . . . . ?
O1 C1 C6 C7 -0.3(3) . . . . ?
N2 C10 C12 C13 -179.65(16) . . . . ?
O3A C8 C9 N2 -32.7(3) . . . . ?
O3B C8 C9 N2 68.1(3) . . . . ?
C20 C21 C25B C24B -175.1(5) . . . . ?
C25A C24A N3A C23A 0.0 . . . . ?
C24A C25A C21 C22 0.0 . . . . ?
C24A N3A C23A C22 0.0 . . . . ?
N3A C23A C22 C21 0.0 . . . . ?
C23A C22 C21 C25A 0.0 . . . . ?
C22 C21 C25B C24B -1.0(7) . . . . ?
C22 C23B N3B C24B 1.9(10) . . . . ?
C21 C25A C24A N3A 0.0 . . . . ?
C21 C22 C23B N3B -2.0(9) . . . . ?
C23B C22 C21 C20 175.5(5) . . . . ?
C23B C22 C21 C25B 1.4(6) . . . . ?
C25B C24B N3B C23B -1.3(9) . . . . ?
N3B C24B C25B C21 1.0(9) . . . . ?
O4 C20 C21 C22 167.73(18) . . . . ?
O4 C20 C21 C25B -18.5(5) . . . . ?
O5 C20 C21 C22 -13.3(3) . . . . ?
O5 C20 C21 C25B 160.5(5) . . . . ?

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

data_ProINA
_database_code_depnum_ccdc_archive 'CCDC 2371671'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 N O2, C6 H4 N O2'
_chemical_formula_sum            'C22 H26 N2 O4'
_chemical_formula_weight         382.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44  N4  O8  H1  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0313(2)
_cell_length_b                   10.0546(2)
_cell_length_c                   13.9004(3)
_cell_angle_alpha                70.899(2)
_cell_angle_beta                 74.871(2)
_cell_angle_gamma                76.988(2)
_cell_volume                     1011.83(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8840
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.9320
_cell_measurement_theta_min      3.3450
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0394
1 -6 -5 0.0393
5 1 1 0.0379
0 1 9 0.0209
1 -2 7 0.0264
0 1 -8 0.0207
-2 6 0 0.0485
-1 5 4 0.0449
0 6 5 0.0420
1 6 3 0.0427
4 2 -4 0.0355
-3 1 5 0.0357
1 6 2 0.0420
-3 1 6 0.0331
3 1 -6 0.0285
0 6 0 0.0412
2 -1 -8 0.0228
1 1 -7 0.0231
-2 2 7 0.0291
0 -2 7 0.0337
0 4 -5 0.0290
0 -2 7 0.0280
0 -2 -9 0.0187
0 -2 -9 0.0187
-1 1 -8 0.0224
0 2 9 0.0266
-2 1 -8 0.0225
1 2 9 0.0260
-2 -1 -9 0.0219
1 3 9 0.0292
2 3 9 0.0333
-4 0 -7 0.0300
-4 0 -7 0.0339
-5 0 -3 0.0403
5 3 4 0.0449
0 6 5 0.0400
4 4 0 0.0468
3 2 8 0.0381
3 3 8 0.0373

_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.041
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
-0.9986 -0.0006 0.0026 -0.1701 -0.0154 0.1056
1.1367 -5.5271 -4.5018 -0.0560 -0.0054 -0.9984
5.1564 1.1843 1.0470 0.9324 0.0735 -0.3539
-0.0835 0.8507 8.5716 0.0697 -0.8876 0.4552
0.8175 -2.4700 6.7569 0.0784 -0.9881 -0.1325
-0.4895 1.2368 -7.7962 -0.0784 0.9919 -0.0995
-1.5551 5.5526 0.3626 -0.0382 0.4690 0.8824
-1.4351 5.4061 4.1174 -0.0020 0.0326 0.9995
0.3990 6.1572 5.0554 0.3463 0.0266 0.9377
0.6448 6.4817 3.2266 0.3908 0.2680 0.8806
3.5503 1.8134 -4.0974 0.6545 0.6907 -0.3075
-3.3729 0.9180 5.0804 -0.5081 -0.5366 0.6737
0.5189 6.4615 2.1881 0.3625 0.3815 0.8503
-2.9892 1.4847 5.6786 -0.4163 -0.5439 0.7286
2.7710 1.0489 -5.7057 0.4815 0.7871 -0.3855
0.1182 6.1626 0.2347 0.2709 0.5673 0.7777
1.5714 -0.7968 -7.5663 0.1917 0.8018 -0.5660
1.2394 1.3815 -7.0310 0.2264 0.9456 -0.2338
-1.6583 1.8175 7.4681 -0.1658 -0.6939 0.7007
-0.4014 -2.4708 6.6230 -0.1301 -0.9915 -0.0090
0.0223 3.7603 -5.2599 0.1256 0.9557 0.2664
0.1234 -2.1596 7.0303 -0.0257 -0.9996 -0.0090
0.3280 -1.7407 -8.5447 -0.0639 0.8028 -0.5928
-0.0880 -2.0257 -8.7446 -0.1475 0.7917 -0.5928
-1.1636 1.4714 -7.6089 -0.1827 0.9831 0.0089
0.0110 2.2415 8.6937 0.1428 -0.7664 0.6263
-1.5456 0.6546 -8.1148 -0.2837 0.9560 -0.0742
0.7348 1.7395 8.9470 0.2473 -0.8323 0.4962
-1.5467 -1.1490 -8.8942 -0.3614 0.8708 -0.3334
0.7605 2.8679 8.8689 0.2968 -0.7147 0.6333
1.5402 3.3528 8.8314 0.4491 -0.6521 0.6109
-3.5302 -0.1141 -7.2829 -0.6481 0.7582 0.0712
-3.9428 -0.2370 -6.7783 -0.7204 0.6832 0.1192
-4.9825 -0.0817 -3.4700 -0.8722 0.3087 0.3795
4.9500 3.0237 4.3854 0.9910 -0.1300 0.0329
-0.4097 5.8512 4.9590 0.1956 -0.0042 0.9807
4.4901 3.8441 0.4802 0.9232 0.3829 0.0313
3.4288 1.9584 8.0885 0.7101 -0.6736 0.2051
3.4792 2.8505 8.0143 0.7544 -0.5787 0.3099

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21381
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.004
_diffrn_reflns_theta_min         3.437
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  25.00   0.50    4.15    --  -47.76  98.00 146.00  210
  2  ω     -5.00  81.00   0.50    4.15    --   47.76 -98.00  39.00  172
  3  ω   -163.00 -86.00   0.50   16.58    --  -91.75 -98.00  39.00  154
  4  ω    -80.00 -19.00   0.50   16.58    --  -91.75  98.00 146.00  122
  5  ω     35.00 106.00   0.50   16.58    --  107.31 -98.00  39.00  142
  6  ω    106.00 178.00   0.50   16.58    --  107.31  98.00 146.00  144
  7  ω   -120.00 -73.00   0.50    4.15    --  -47.76-125.00-150.00   94
  8  ω    -41.00  25.00   0.50    4.15    --  -47.76  38.00 120.00  132
  9  ω    -25.00  28.00   0.50    4.15    --  -47.76  19.00  60.00  106
 10  ω   -123.00 -35.00   0.50    4.15    --  -47.76 -19.00 -30.00  176
 11  ω   -120.00 -73.00   0.50    4.15    --  -47.76-125.00 150.00   94
 12  ω   -163.00 -86.00   0.50   16.58    --  -91.75 -99.00   0.00  154
 13  ω    -85.00 -19.00   0.50   16.58    --  -91.75 125.00-180.00  132
 14  ω    -64.00 -19.00   0.50   16.58    --  -91.75  57.00   0.00   90
 15  ω   -165.00 -78.00   0.50   16.58    --  -91.75 -38.00  60.00  174
 16  ω   -163.00 -69.00   0.50   16.58    --  -91.75 -77.00 120.00  188
 17  ω    -64.00 -19.00   0.50   16.58    --  -91.75  57.00  60.00   90
 18  ω     95.00 178.00   0.50   16.58    --  107.31 125.00 -60.00  166
 19  ω     94.00 178.00   0.50   16.58    --  107.31  38.00 -90.00  168
 20  ω     35.00 111.00   0.50   16.58    --  107.31-125.00-120.00  152
 21  ω     35.00 106.00   0.50   16.58    --  107.31 -99.00-120.00  142
 22  ω     35.00  68.00   0.50   16.58    --  107.31 -57.00   0.00   66
 23  ω     35.00  68.00   0.50   16.58    --  107.31 -57.00-120.00   66
 24  ω     35.00 106.00   0.50   16.58    --  107.31 -99.00 -60.00  142
 25  ω     35.00 106.00   0.50   16.58    --  107.31 -99.00 120.00  142
 26  ω     35.00 106.00   0.50   16.58    --  107.31 -99.00  90.00  142
 27  ω     92.00 178.00   0.50   16.58    --  107.31  57.00-120.00  172
 28  ω     35.00  68.00   0.50   16.58    --  107.31 -57.00 -60.00   66
 29  ω     35.00 106.00   0.50   16.58    --  107.31 -99.00   0.00  142
 30  ω     35.00  68.00   0.50   16.58    --  107.31 -57.00 -90.00   66
 31  ω   -120.00 -33.00   0.50    4.15    --  -47.76 -57.00 -30.00  174
 32  ω   -120.00 -25.00   0.50    4.15    --  -47.76 -77.00 -90.00  190
 33  ω   -120.00 -25.00   0.50    4.15    --  -47.76 -77.00 150.00  190
 34  ω   -120.00 -25.00   0.50    4.15    --  -47.76 -77.00 120.00  190
 35  ω   -120.00 -25.00   0.50    4.15    --  -47.76 -77.00  60.00  190
 36  ω   -120.00 -25.00   0.50    4.15    --  -47.76 -77.00 -30.00  190
 37  ω   -120.00 -33.00   0.50    4.15    --  -47.76 -57.00-180.00  174
 38  ω   -163.00-123.00   0.50   16.58    --  -91.75 -77.00 -60.00   80
 39  ω   -163.00 -69.00   0.50   16.58    --  -91.75 -77.00  60.00  188
 40  ω   -163.00 -69.00   0.50   16.58    --  -91.75 -77.00 150.00  188
 41  ω   -163.00 -69.00   0.50   16.58    --  -91.75 -77.00   0.00  188
 42  ω   -163.00 -69.00   0.50   16.58    --  -91.75 -77.00-120.00  188
 43  ω   -163.00 -69.00   0.50   16.58    --  -91.75 -77.00-180.00  188
;
_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      0.1703591000
_diffrn_orient_matrix_UB_12      0.0404628000
_diffrn_orient_matrix_UB_13      0.0057770000
_diffrn_orient_matrix_UB_21      0.0151162000
_diffrn_orient_matrix_UB_22      0.0960690000
_diffrn_orient_matrix_UB_23      -0.1129432000
_diffrn_orient_matrix_UB_31      -0.1057493000
_diffrn_orient_matrix_UB_32      0.1267172000
_diffrn_orient_matrix_UB_33      0.0395042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3253
_reflns_number_total             4079
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.3376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1077
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3208(2) 0.9408(2) 0.98125(14) 0.0437(4) Uani 1 1 d . . . . .
H1 H 0.299342 1.023725 1.003837 0.052 Uiso 1 1 calc R U . . .
C2 C 0.2327(2) 0.8300(2) 1.03775(13) 0.0423(4) Uani 1 1 d . . . . .
H2 H 0.151574 0.836232 1.100129 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2593(2) 0.7060(2) 1.00560(12) 0.0371(4) Uani 1 1 d . . . . .
C4 C 0.1716(2) 0.5881(2) 1.06390(13) 0.0424(4) Uani 1 1 d . . . . .
H4 H 0.091520 0.590832 1.127272 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2010(2) 0.4717(2) 1.02996(13) 0.0417(4) Uani 1 1 d . . . . .
H5 H 0.141545 0.393472 1.070358 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3180(2) 0.46370(19) 0.93585(12) 0.0365(4) Uani 1 1 d . . . . .
H6 H 0.336336 0.381155 0.913136 0.044 Uiso 1 1 calc R U . . .
C7 C 0.40497(19) 0.57599(17) 0.87753(11) 0.0320(3) Uani 1 1 d . . . . .
C8 C 0.38085(19) 0.69980(18) 0.91102(11) 0.0325(3) Uani 1 1 d . . . . .
C9 C 0.4725(2) 0.81558(18) 0.85506(12) 0.0348(4) Uani 1 1 d . . . . .
H9 H 0.555202 0.811721 0.792759 0.042 Uiso 1 1 calc R U . . .
C10 C 0.4436(2) 0.93299(19) 0.88954(13) 0.0399(4) Uani 1 1 d . . . . .
H10 H 0.506804 1.009773 0.851386 0.048 Uiso 1 1 calc R U . . .
C11 C 0.5400(2) 0.46187(16) 0.74529(12) 0.0319(3) Uani 1 1 d . . . . .
H11A H 0.426223 0.450994 0.735933 0.038 Uiso 1 1 calc R U . . .
H11B H 0.584039 0.373666 0.795414 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6684(2) 0.48643(16) 0.64217(11) 0.0300(3) Uani 1 1 d . . . . .
H12 H 0.784931 0.492025 0.652629 0.036 Uiso 1 1 calc R U . . .
C13 C 0.60628(19) 0.62207(16) 0.56269(11) 0.0293(3) Uani 1 1 d . . . . .
H13A H 0.493185 0.614742 0.550309 0.035 Uiso 1 1 calc R U . . .
H13B H 0.588603 0.704634 0.590093 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6848(2) 0.76644(16) 0.37263(11) 0.0294(3) Uani 1 1 d . . . . .
H14 H 0.575239 0.751138 0.359011 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6511(2) 0.90691(17) 0.39778(13) 0.0394(4) Uani 1 1 d . . . . .
H15A H 0.555498 0.905283 0.458475 0.059 Uiso 1 1 calc R U . . .
H15B H 0.619253 0.984590 0.338105 0.059 Uiso 1 1 calc R U . . .
H15C H 0.756868 0.921780 0.413028 0.059 Uiso 1 1 calc R U . . .
C16 C 0.8292(2) 0.76403(17) 0.27771(12) 0.0352(4) Uani 1 1 d . . . . .
H16A H 0.937240 0.778905 0.290279 0.053 Uiso 1 1 calc R U . . .
H16B H 0.796289 0.839983 0.217471 0.053 Uiso 1 1 calc R U . . .
H16C H 0.847485 0.671650 0.264011 0.053 Uiso 1 1 calc R U . . .
N1 N 0.73751(16) 0.64434(13) 0.46283(9) 0.0266(3) Uani 1 1 d . . . . .
H1A H 0.767(2) 0.561(2) 0.4403(14) 0.041(5) Uiso 1 1 d . . . . .
H1B H 0.841(3) 0.659(2) 0.4769(16) 0.053(6) Uiso 1 1 d . . . . .
O1 O 0.51902(14) 0.58104(12) 0.78399(8) 0.0331(3) Uani 1 1 d . . . . .
O2 O 0.68036(15) 0.36508(11) 0.60907(9) 0.0353(3) Uani 1 1 d . . . . .
H2A H 0.798(3) 0.341(2) 0.5684(18) 0.065(7) Uiso 1 1 d . . . . .
C17 C 0.93136(19) 0.31936(16) 0.40276(12) 0.0287(3) Uani 1 1 d . . . . .
C18 C 0.99795(18) 0.20988(15) 0.34307(11) 0.0271(3) Uani 1 1 d . . . . .
C19 C 1.11750(19) 0.09021(16) 0.37591(12) 0.0302(3) Uani 1 1 d . . . . .
H19 H 1.160729 0.075701 0.436581 0.036 Uiso 1 1 calc R U . . .
C20 C 1.1729(2) -0.00752(17) 0.31935(12) 0.0335(3) Uani 1 1 d . . . . .
H20 H 1.254767 -0.088736 0.342923 0.040 Uiso 1 1 calc R U . . .
C21 C 1.0025(2) 0.12132(17) 0.20257(13) 0.0364(4) Uani 1 1 d . . . . .
H21 H 0.960888 0.132976 0.141842 0.044 Uiso 1 1 calc R U . . .
C22 C 0.9400(2) 0.22510(16) 0.25391(12) 0.0325(3) Uani 1 1 d . . . . .
H22 H 0.858595 0.305570 0.228425 0.039 Uiso 1 1 calc R U . . .
N2 N 1.11780(18) 0.00553(14) 0.23320(10) 0.0352(3) Uani 1 1 d . . . . .
O3 O 0.98380(13) 0.29437(11) 0.48666(8) 0.0318(2) Uani 1 1 d . . . . .
O4 O 0.82587(15) 0.42529(11) 0.36801(9) 0.0359(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.360(3) . ?
C1 C10 1.407(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.413(3) . ?
C3 C4 1.417(3) . ?
C3 C8 1.429(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.351(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.412(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.371(2) . ?
C7 C8 1.424(2) . ?
C7 O1 1.3741(18) . ?
C8 C9 1.413(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.366(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.514(2) . ?
C11 O1 1.4272(18) . ?
C12 H12 1.0000 . ?
C12 C13 1.525(2) . ?
C12 O2 1.4147(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 N1 1.4922(18) . ?
C14 H14 1.0000 . ?
C14 C15 1.514(2) . ?
C14 C16 1.515(2) . ?
C14 N1 1.5148(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 H1A 0.95(2) . ?
N1 H1B 0.96(2) . ?
O2 H2A 0.99(2) . ?
C17 C18 1.512(2) . ?
C17 O3 1.2719(18) . ?
C17 O4 1.2474(18) . ?
C18 C19 1.388(2) . ?
C18 C22 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(2) . ?
C20 H20 0.9500 . ?
C20 N2 1.339(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(2) . ?
C21 N2 1.338(2) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
C2 C1 C10 120.30(17) . . ?
C10 C1 H1 119.8 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.37(16) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 122.55(15) . . ?
C2 C3 C8 118.23(16) . . ?
C4 C3 C8 119.22(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.45(16) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.57(17) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.48(16) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 121.04(14) . . ?
C6 C7 O1 124.50(15) . . ?
O1 C7 C8 114.45(13) . . ?
C7 C8 C3 118.22(15) . . ?
C9 C8 C3 119.00(15) . . ?
C9 C8 C7 122.77(14) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.74(15) . . ?
C10 C9 H9 119.6 . . ?
C1 C10 H10 119.8 . . ?
C9 C10 C1 120.32(17) . . ?
C9 C10 H10 119.8 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
O1 C11 H11A 110.0 . . ?
O1 C11 H11B 110.0 . . ?
O1 C11 C12 108.65(12) . . ?
C11 C12 H12 109.7 . . ?
C11 C12 C13 111.75(12) . . ?
C13 C12 H12 109.7 . . ?
O2 C12 C11 105.02(12) . . ?
O2 C12 H12 109.7 . . ?
O2 C12 C13 110.88(12) . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N1 C13 C12 110.26(12) . . ?
N1 C13 H13A 109.6 . . ?
N1 C13 H13B 109.6 . . ?
C15 C14 H14 108.8 . . ?
C15 C14 C16 111.80(13) . . ?
C15 C14 N1 110.72(12) . . ?
C16 C14 H14 108.8 . . ?
N1 C14 H14 108.8 . . ?
N1 C14 C16 107.81(12) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 N1 C14 116.19(11) . . ?
C13 N1 H1A 110.5(11) . . ?
C13 N1 H1B 107.0(12) . . ?
C14 N1 H1A 106.9(11) . . ?
C14 N1 H1B 109.1(12) . . ?
H1A N1 H1B 106.9(16) . . ?
C7 O1 C11 116.10(12) . . ?
C12 O2 H2A 111.3(13) . . ?
O3 C17 C18 117.25(13) . . ?
O4 C17 C18 118.01(13) . . ?
O4 C17 O3 124.72(14) . . ?
C19 C18 C17 121.42(13) . . ?
C22 C18 C17 120.93(13) . . ?
C22 C18 C19 117.65(14) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.22(14) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 118.1 . . ?
N2 C20 C19 123.83(14) . . ?
N2 C20 H20 118.1 . . ?
C22 C21 H21 118.0 . . ?
N2 C21 H21 118.0 . . ?
N2 C21 C22 124.03(15) . . ?
C18 C22 H22 120.5 . . ?
C21 C22 C18 119.00(14) . . ?
C21 C22 H22 120.5 . . ?
C21 N2 C20 116.26(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
C1 C2 C3 C4 178.85(16) . . . . ?
C1 C2 C3 C8 -0.5(2) . . . . ?
C2 C1 C10 C9 1.5(3) . . . . ?
C2 C3 C4 C5 179.90(16) . . . . ?
C2 C3 C8 C7 -178.73(14) . . . . ?
C2 C3 C8 C9 1.6(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C8 C9 C10 -1.1(2) . . . . ?
C4 C3 C8 C7 1.9(2) . . . . ?
C4 C3 C8 C9 -177.80(14) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C5 C6 C7 O1 -178.70(14) . . . . ?
C6 C7 C8 C3 -1.9(2) . . . . ?
C6 C7 C8 C9 177.71(15) . . . . ?
C6 C7 O1 C11 2.6(2) . . . . ?
C7 C8 C9 C10 179.22(15) . . . . ?
C8 C3 C4 C5 -0.7(2) . . . . ?
C8 C7 O1 C11 -177.00(12) . . . . ?
C8 C9 C10 C1 -0.4(2) . . . . ?
C10 C1 C2 C3 -1.0(3) . . . . ?
C11 C12 C13 N1 178.89(12) . . . . ?
C12 C11 O1 C7 179.63(12) . . . . ?
C12 C13 N1 C14 173.59(12) . . . . ?
C15 C14 N1 C13 61.43(17) . . . . ?
C16 C14 N1 C13 -175.99(12) . . . . ?
O1 C7 C8 C3 177.64(13) . . . . ?
O1 C7 C8 C9 -2.7(2) . . . . ?
O1 C11 C12 C13 -59.20(16) . . . . ?
O1 C11 C12 O2 -179.48(11) . . . . ?
O2 C12 C13 N1 -64.32(16) . . . . ?
C17 C18 C19 C20 179.27(14) . . . . ?
C17 C18 C22 C21 -179.07(14) . . . . ?
C18 C19 C20 N2 0.0(2) . . . . ?
C19 C18 C22 C21 0.3(2) . . . . ?
C19 C20 N2 C21 0.0(2) . . . . ?
C22 C18 C19 C20 -0.1(2) . . . . ?
C22 C21 N2 C20 0.3(2) . . . . ?
N2 C21 C22 C18 -0.4(3) . . . . ?
O3 C17 C18 C19 -2.8(2) . . . . ?
O3 C17 C18 C22 176.50(14) . . . . ?
O4 C17 C18 C19 179.04(14) . . . . ?
O4 C17 C18 C22 -1.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   1354
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.676
####################################################################### 
# 
# 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_AceNA
_database_code_depnum_ccdc_archive 'CCDC 2371675'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H29 N2 O4, C6 H4 N O2'
_chemical_formula_sum            'C24 H33 N3 O6'
_chemical_formula_weight         459.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.1288(2)
_cell_length_b                   13.1402(2)
_cell_length_c                   25.5766(2)
_cell_angle_alpha                76.0570(10)
_cell_angle_beta                 82.4310(10)
_cell_angle_gamma                77.3610(10)
_cell_volume                     3529.68(9)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    46354
_cell_measurement_temperature    100.00(15)
_cell_measurement_theta_max      78.6600
_cell_measurement_theta_min      3.5460
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.119a (Rigaku Oxford Diffraction, 2024)
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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1476
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 2 10 0.0468
5 -2 -10 0.0468
-1 -2 -17 0.0314
1 2 17 0.0314
4 6 -6 0.0271
7 1 6 0.0228
-2 -7 6 0.0589
1 -5 -14 0.0384
-6 0 6 0.0457
-7 -3 -8 0.0443
-3 7 3 0.0459
-4 5 -4 0.0325

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
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
-4.7529 2.4455 9.9516 -0.1749 -0.4882 -0.8550
4.7529 -2.4455 -9.9516 0.1749 0.4882 0.8550
-1.3138 -2.2250 -16.5797 -0.0989 -0.4027 0.9100
1.3138 2.2250 16.5797 0.0989 0.4027 -0.9100
3.9078 5.9908 -6.1447 0.9042 -0.1168 0.4108
6.9092 0.7418 5.8718 0.4295 0.9030 0.0091
-1.8786 -7.0489 5.5314 -0.8750 0.4153 -0.2488
0.8993 -5.3697 -13.8627 -0.3033 0.1472 0.9415
-6.3053 0.0611 5.9491 -0.4565 -0.5994 -0.6575
-6.6831 -2.8915 -8.1939 -0.5983 -0.7807 0.1803
-3.1776 6.6279 3.4578 0.4117 -0.7592 -0.5040
-4.2216 5.0672 -3.9582 0.2837 -0.9528 -0.1078

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            106207
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         81.190
_diffrn_reflns_theta_min         3.533
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -35.00   0.50    1.00    --  -47.63 -34.00  37.00  174
  2  ω     35.00 122.00   0.50    1.00    --   47.63  34.00-165.00  174
  3  ω    -26.00  41.00   0.50    1.00    --   47.63 -34.00  37.00  134
  4  ω     35.00 122.00   0.50    1.00    --   47.63  34.00-165.00  174
  5  ω   -177.00 -93.00   0.50    4.00    -- -106.00 -34.00  37.00  168
  6  ω    100.00 178.00   0.50    4.00    --  113.25  34.00-165.00  156
  7  ω    -38.00  27.00   0.50    1.00    --  -47.63  34.00-165.00  130
  8  ω     16.00  93.00   0.50    1.00    --   47.63-125.00-150.00  154
  9  ω    -25.00  45.00   0.50    1.00    --   47.63 -38.00 120.00  140
 10  ω    -25.00  45.00   0.50    1.00    --   47.63 -38.00 -90.00  140
 11  ω     16.00  93.00   0.50    1.00    --   47.63-125.00-150.00  154
 12  ω    -24.00  63.00   0.50    1.00    --   47.63 -57.00  30.00  174
 13  ω      0.00  80.00   0.50    1.00    --   47.63 -99.00 -60.00  160
 14  ω   -108.00 -37.00   0.50    4.00    -- -106.00 112.00  73.24  142
 15  ω   -126.00 -33.00   0.50    4.00    -- -106.00 145.00 -52.88  186
 16  ω   -126.00 -33.00   0.50    4.00    -- -106.00 145.00 -52.88  186
 17  ω   -125.00 -33.00   0.50    4.00    -- -106.00 143.00 174.50  184
 18  ω   -121.00 -33.00   0.50    4.00    -- -106.00 138.00-131.92  176
 19  ω   -125.00 -33.00   0.50    4.00    -- -106.00 143.00 118.77  184
 20  ω   -122.00 -33.00   0.50    4.00    -- -106.00 139.00  58.89  178
 21  ω   -124.00 -33.00   0.50    4.00    -- -106.00 142.00 -13.81  182
 22  ω   -177.00-110.00   0.50    4.00    -- -106.00 -77.00 120.00  134
 23  ω   -123.00 -33.00   0.50    4.00    -- -106.00 141.00  11.50  180
 24  ω   -121.00 -33.00   0.50    4.00    -- -106.00 138.00-131.92  176
 25  ω   -125.00 -33.00   0.50    4.00    -- -106.00 143.00 -92.20  184
 26  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00-150.00  128
 27  ω    101.00 178.00   0.50    4.00    --  113.25  30.00 150.00  154
 28  ω     42.00 104.00   0.50    4.00    --  113.25 -77.00 -30.00  124
 29  ω    106.00 178.00   0.50    4.00    --  113.25  61.00 -90.00  144
 30  ω    101.00 178.00   0.50    4.00    --  113.25  30.00 150.00  154
 31  ω     42.00  73.00   0.50    4.00    --  113.25 -61.00 -60.00   62
 32  ω     94.00 178.00   0.50    4.00    --  113.25 125.00   0.00  168
 33  ω     44.00 111.00   0.50    4.00    --  113.25-125.00  30.00  134
 34  ω     42.00 104.00   0.50    4.00    --  113.25 -77.00-180.00  124
 35  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00  90.00  128
 36  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00 -90.00  128
 37  ω    106.00 178.00   0.50    4.00    --  113.25  61.00   0.00  144
 38  ω     42.00  73.00   0.50    4.00    --  113.25 -61.00 -90.00   62
 39  ω     42.00  73.00   0.50    4.00    --  113.25 -61.00-150.00   62
 40  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00-180.00  128
 41  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00-180.00  128
 42  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00  60.00  128
 43  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00  30.00  128
 44  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00   0.00  128
 45  ω     42.00 106.00   0.50    4.00    --  113.25 -95.00  30.00  128
 46  ω     44.00  81.00   0.50    4.00    --  113.25-125.00   0.00   74
 47  ω    107.00 169.00   0.50    4.00    --  113.25  30.00-180.00  124
 48  ω     46.00  73.00   0.50    4.00    --  113.25 -61.00  30.00   54
 49  ω    101.00 138.00   0.50    4.00    --  113.25  30.00 120.00   74
 50  ω    148.00 174.00   0.50    4.00    --  113.25  30.00 120.00   52
 51  ω     47.00  73.00   0.50    4.00    --  113.25 -77.00  30.00   52
 52  ω     78.00 103.00   0.50    4.00    --  113.25 -77.00  30.00   50
 53  ω     64.00  90.00   0.50    4.00    --  113.25 -95.00 -60.00   52
 54  ω    102.00 136.00   0.50    4.00    --  113.25  30.00  60.00   68
 55  ω     50.00 103.00   0.50    4.00    --  113.25 -95.00-120.00  106
 56  ω     54.00 104.00   0.50    4.00    --  113.25 -95.00 120.00  100
 57  ω     42.00  72.00   0.50    4.00    --  113.25 -61.00  90.00   60
 58  ω     78.00 104.00   0.50    4.00    --  113.25 -77.00 -90.00   52
 59  ω     71.00 101.00   0.50    4.00    --  113.25 -77.00  90.00   60
 60  ω    149.00 175.00   0.50    4.00    --  113.25  77.00  90.00   52
 61  ω     43.00  73.00   0.50    4.00    --  113.25 -61.00 120.00   60
 62  ω    106.00 178.00   0.50    4.00    --  113.25  61.00-150.00  144
 63  ω    133.00 166.00   0.50    4.00    --  113.25  30.00 -30.00   66
 64  ω    117.00 169.00   0.50    4.00    --  113.25  61.00-120.00  104
 65  ω     73.00  99.00   0.50    4.00    --  113.25 -77.00-180.00   52
 66  ω     74.00 100.00   0.50    4.00    --  113.25 -77.00-120.00   52
 67  ω     59.00  85.00   0.50    4.00    --  113.25 -77.00   0.00   52
 68  ω     62.00 111.00   0.50    4.00    --  113.25-125.00 -60.00   98
 69  ω    102.00 129.00   0.50    4.00    --  113.25  30.00 -30.00   54
 70  ω    136.00 162.00   0.50    4.00    --  113.25  77.00-120.00   52
 71  ω     80.00 106.00   0.50    4.00    --  113.25 -95.00 -90.00   52
 72  ω     79.00 106.00   0.50    4.00    --  113.25 -95.00-150.00   54
 73  ω     45.00  71.00   0.50    4.00    --  113.25 -87.00 105.97   52
 74  ω     92.00 118.00   0.50    4.00    --  113.25 -87.00 105.97   52
 75  ω     64.00 105.00   0.50    4.00    --  113.25 -95.00 150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0619199000
_diffrn_orient_matrix_UB_12      0.0981226000
_diffrn_orient_matrix_UB_13      -0.0121114000
_diffrn_orient_matrix_UB_21      0.1174960000
_diffrn_orient_matrix_UB_22      -0.0710054000
_diffrn_orient_matrix_UB_23      0.0245048000
_diffrn_orient_matrix_UB_31      0.0512665000
_diffrn_orient_matrix_UB_32      -0.0222724000
_diffrn_orient_matrix_UB_33      -0.0559596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                13634
_reflns_number_total             15222
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     952
_refine_ls_number_reflns         15222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.071
_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)+(0.0648P)²+1.3312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C16(H16), C32(H32), C34(H34), C50(H50), C52(H52)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C15(H15A,H15B), C20(H20A,H20B),
 C21(H21A,H21B), C31(H31A,H31B), C33(H33A,H33B), C38(H38A,H38B), C39(H39A,H39B),
  C49(H49A,H49B), C51(H51A,H51B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C24(H24), C27(H27), C28(H28), C42(H42), C45(H45),
 C46(H46), C57(H57), C58(H58), C59(H59), C60(H60), C69(H69), C70(H70), C71(H71),
  C72(H72), C63(H63), C64(H64), C65(H65), C66(H66)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C30(H30A,H30B,H30C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C37(H37A,H37B,H37C), C48(H48A,H48B,H48C), C53(H53A,H53B,H53C),
 C54(H54A,H54B,H54C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.17792(15) 0.35895(12) 0.92484(5) 0.0298(3) Uani 1 1 d . . . . .
H1A H 0.112959 0.419686 0.930835 0.045 Uiso 1 1 calc R U . . .
H1B H 0.257647 0.370364 0.932171 0.045 Uiso 1 1 calc R U . . .
H1C H 0.159356 0.293203 0.949116 0.045 Uiso 1 1 calc R U . . .
C2 C 0.18385(14) 0.34900(11) 0.86640(5) 0.0261(3) Uani 1 1 d . . . . .
H2A H 0.252843 0.290406 0.859846 0.031 Uiso 1 1 calc R U . . .
H2B H 0.106164 0.330512 0.860087 0.031 Uiso 1 1 calc R U . . .
C3 C 0.20253(14) 0.45239(11) 0.82696(5) 0.0251(3) Uani 1 1 d . . . . .
H3A H 0.134086 0.510855 0.834204 0.030 Uiso 1 1 calc R U . . .
H3B H 0.280506 0.470205 0.833402 0.030 Uiso 1 1 calc R U . . .
C4 C 0.20760(12) 0.44685(10) 0.76813(5) 0.0209(2) Uani 1 1 d . . . . .
C5 C 0.20128(12) 0.56821(11) 0.67644(5) 0.0214(3) Uani 1 1 d . . . . .
C6 C 0.19755(13) 0.67421(11) 0.64985(5) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.202527 0.724633 0.670194 0.028 Uiso 1 1 calc R U . . .
C7 C 0.18678(13) 0.70932(11) 0.59437(5) 0.0230(3) Uani 1 1 d . . . . .
C8 C 0.17830(13) 0.63395(11) 0.56474(5) 0.0224(3) Uani 1 1 d . . . . .
C9 C 0.18369(13) 0.52729(11) 0.59109(5) 0.0227(3) Uani 1 1 d . . . . .
H9 H 0.179181 0.476360 0.570978 0.027 Uiso 1 1 calc R U . . .
C10 C 0.19555(12) 0.49427(10) 0.64629(5) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.199761 0.421110 0.663564 0.026 Uiso 1 1 calc R U . . .
C11 C 0.18704(14) 0.82602(11) 0.57139(5) 0.0262(3) Uani 1 1 d . . . . .
C12 C 0.1861(2) 0.87293(13) 0.51203(6) 0.0445(5) Uani 1 1 d . . . . .
H12A H 0.253593 0.831449 0.492624 0.067 Uiso 1 1 calc R U . . .
H12B H 0.197152 0.947178 0.504745 0.067 Uiso 1 1 calc R U . . .
H12C H 0.106996 0.870921 0.499804 0.067 Uiso 1 1 calc R U . . .
C13 C 0.15935(13) 0.59868(11) 0.47832(5) 0.0236(3) Uani 1 1 d . . . . .
H13A H 0.090377 0.560012 0.491352 0.028 Uiso 1 1 calc R U . . .
H13B H 0.237951 0.545882 0.478716 0.028 Uiso 1 1 calc R U . . .
C14 C 0.14177(13) 0.66710(11) 0.42189(5) 0.0220(3) Uani 1 1 d . . . . .
H14 H 0.066667 0.724324 0.424069 0.026 Uiso 1 1 calc R U . . .
C15 C 0.12193(13) 0.60296(11) 0.38278(5) 0.0235(3) Uani 1 1 d . . . . .
H15A H 0.187131 0.537718 0.384937 0.028 Uiso 1 1 calc R U . . .
H15B H 0.040780 0.581021 0.392245 0.028 Uiso 1 1 calc R U . . .
C16 C 0.05455(13) 0.64450(11) 0.28781(5) 0.0229(3) Uani 1 1 d . . . . .
H16 H -0.035040 0.656710 0.300909 0.027 Uiso 1 1 calc R U . . .
C17 C 0.07178(14) 0.72122(12) 0.23382(5) 0.0273(3) Uani 1 1 d . . . . .
H17A H 0.158083 0.706039 0.219142 0.041 Uiso 1 1 calc R U . . .
H17B H 0.050580 0.794838 0.238866 0.041 Uiso 1 1 calc R U . . .
H17C H 0.017798 0.712320 0.208582 0.041 Uiso 1 1 calc R U . . .
C18 C 0.09650(14) 0.52836(11) 0.28389(6) 0.0271(3) Uani 1 1 d . . . . .
H18A H 0.053811 0.514584 0.255901 0.041 Uiso 1 1 calc R U . . .
H18B H 0.076849 0.481865 0.318741 0.041 Uiso 1 1 calc R U . . .
H18C H 0.185910 0.513678 0.274488 0.041 Uiso 1 1 calc R U . . .
N1 N 0.20856(11) 0.54263(9) 0.73304(4) 0.0233(2) Uani 1 1 d . . . . .
H1 H 0.2102(18) 0.5962(16) 0.7457(8) 0.033(5) Uiso 1 1 d . . . . .
N2 N 0.12637(11) 0.67068(9) 0.32697(4) 0.0209(2) Uani 1 1 d . . . . .
H2C H 0.2082(18) 0.6649(14) 0.3134(7) 0.027(4) Uiso 1 1 d . . . . .
H2D H 0.1022(17) 0.7437(16) 0.3285(7) 0.029(4) Uiso 1 1 d . . . . .
O1 O 0.21037(10) 0.36332(7) 0.75432(4) 0.0249(2) Uani 1 1 d . . . . .
O2 O 0.19070(12) 0.88277(8) 0.60213(4) 0.0346(3) Uani 1 1 d . . . . .
O3 O 0.16138(11) 0.67133(8) 0.51101(4) 0.0278(2) Uani 1 1 d . . . . .
O4 O 0.24419(9) 0.71689(8) 0.40275(4) 0.02253(19) Uani 1 1 d . . . . .
H4 H 0.209(2) 0.793(2) 0.3942(10) 0.061(7) Uiso 1 1 d . . . . .
C19 C 0.42436(15) 0.05898(12) 1.24240(5) 0.0296(3) Uani 1 1 d . . . . .
H19A H 0.354713 0.117111 1.247204 0.044 Uiso 1 1 calc R U . . .
H19B H 0.500182 0.075195 1.251220 0.044 Uiso 1 1 calc R U . . .
H19C H 0.408686 -0.008000 1.266400 0.044 Uiso 1 1 calc R U . . .
C20 C 0.43911(14) 0.04751(11) 1.18392(5) 0.0249(3) Uani 1 1 d . . . . .
H20A H 0.511560 -0.009320 1.178874 0.030 Uiso 1 1 calc R U . . .
H20B H 0.365016 0.025560 1.176016 0.030 Uiso 1 1 calc R U . . .
C21 C 0.45623(13) 0.15125(11) 1.14447(5) 0.0230(3) Uani 1 1 d . . . . .
H21A H 0.381793 0.206872 1.148530 0.028 Uiso 1 1 calc R U . . .
H21B H 0.527441 0.175035 1.153946 0.028 Uiso 1 1 calc R U . . .
C22 C 0.47791(12) 0.14185(10) 1.08576(5) 0.0208(2) Uani 1 1 d . . . . .
C23 C 0.49905(13) 0.25674(11) 0.99308(5) 0.0216(3) Uani 1 1 d . . . . .
C24 C 0.50834(13) 0.36029(11) 0.96594(5) 0.0231(3) Uani 1 1 d . . . . .
H24 H 0.508607 0.411623 0.986471 0.028 Uiso 1 1 calc R U . . .
C25 C 0.51730(13) 0.39164(11) 0.90961(5) 0.0226(3) Uani 1 1 d . . . . .
C26 C 0.51610(13) 0.31465(11) 0.87971(5) 0.0221(3) Uani 1 1 d . . . . .
C27 C 0.50907(13) 0.21023(11) 0.90672(5) 0.0228(3) Uani 1 1 d . . . . .
H27 H 0.509812 0.158282 0.886425 0.027 Uiso 1 1 calc R U . . .
C28 C 0.50099(13) 0.18077(11) 0.96288(5) 0.0222(3) Uani 1 1 d . . . . .
H28 H 0.496810 0.109132 0.980661 0.027 Uiso 1 1 calc R U . . .
C29 C 0.52717(14) 0.50617(11) 0.88589(5) 0.0252(3) Uani 1 1 d . . . . .
C30 C 0.55555(17) 0.54702(12) 0.82651(6) 0.0338(3) Uani 1 1 d . . . . .
H30A H 0.625150 0.497469 0.813004 0.051 Uiso 1 1 calc R U . . .
H30B H 0.577163 0.617609 0.820382 0.051 Uiso 1 1 calc R U . . .
H30C H 0.482884 0.552677 0.807343 0.051 Uiso 1 1 calc R U . . .
C31 C 0.51908(14) 0.27406(11) 0.79280(5) 0.0243(3) Uani 1 1 d . . . . .
H31A H 0.444355 0.241910 0.802292 0.029 Uiso 1 1 calc R U . . .
H31B H 0.593171 0.216260 0.797846 0.029 Uiso 1 1 calc R U . . .
C32 C 0.52115(13) 0.33918(11) 0.73500(5) 0.0224(3) Uani 1 1 d . . . . .
H32 H 0.453164 0.403574 0.732904 0.027 Uiso 1 1 calc R U . . .
C33 C 0.50007(14) 0.27446(11) 0.69661(5) 0.0249(3) Uani 1 1 d . . . . .
H33A H 0.558883 0.205113 0.701996 0.030 Uiso 1 1 calc R U . . .
H33B H 0.415079 0.260048 0.703878 0.030 Uiso 1 1 calc R U . . .
C34 C 0.45023(13) 0.30990(11) 0.59960(5) 0.0225(3) Uani 1 1 d . . . . .
H34 H 0.359738 0.324725 0.610870 0.027 Uiso 1 1 calc R U . . .
C35 C 0.47434(14) 0.38460(12) 0.54566(5) 0.0264(3) Uani 1 1 d . . . . .
H35A H 0.561294 0.366206 0.532409 0.040 Uiso 1 1 calc R U . . .
H35B H 0.455727 0.458529 0.550219 0.040 Uiso 1 1 calc R U . . .
H35C H 0.421561 0.377293 0.519513 0.040 Uiso 1 1 calc R U . . .
C36 C 0.48962(14) 0.19280(11) 0.59747(6) 0.0265(3) Uani 1 1 d . . . . .
H36A H 0.451518 0.179267 0.568022 0.040 Uiso 1 1 calc R U . . .
H36B H 0.463009 0.148526 0.631874 0.040 Uiso 1 1 calc R U . . .
H36C H 0.579777 0.174955 0.591142 0.040 Uiso 1 1 calc R U . . .
N3 N 0.48622(11) 0.23569(9) 1.05026(4) 0.0234(2) Uani 1 1 d . . . . .
H3 H 0.4792(18) 0.2907(16) 1.0641(8) 0.032(5) Uiso 1 1 d . . . . .
N4 N 0.51836(11) 0.33574(9) 0.63997(4) 0.0209(2) Uani 1 1 d . . . . .
H4A H 0.5021(19) 0.4076(17) 0.6390(8) 0.037(5) Uiso 1 1 d . . . . .
H4B H 0.6031(19) 0.3212(15) 0.6291(8) 0.032(5) Uiso 1 1 d . . . . .
O5 O 0.48770(9) 0.05645(7) 1.07244(4) 0.0241(2) Uani 1 1 d . . . . .
O6 O 0.51193(13) 0.56745(8) 0.91629(4) 0.0369(3) Uani 1 1 d . . . . .
O7 O 0.51810(10) 0.34850(8) 0.82492(4) 0.0272(2) Uani 1 1 d . . . . .
O8 O 0.63531(9) 0.37377(8) 0.72009(4) 0.02283(19) Uani 1 1 d . . . . .
H8 H 0.617(2) 0.452(2) 0.7101(10) 0.067(7) Uiso 1 1 d . . . . .
C37 C 0.16239(15) 0.26982(13) 0.44512(6) 0.0311(3) Uani 1 1 d . . . . .
H37A H 0.164826 0.339693 0.420874 0.047 Uiso 1 1 calc R U . . .
H37B H 0.082022 0.250979 0.444867 0.047 Uiso 1 1 calc R U . . .
H37C H 0.228133 0.215639 0.432823 0.047 Uiso 1 1 calc R U . . .
C38 C 0.18132(14) 0.27470(11) 0.50229(5) 0.0260(3) Uani 1 1 d . . . . .
H38A H 0.261952 0.294942 0.502255 0.031 Uiso 1 1 calc R U . . .
H38B H 0.115820 0.330632 0.514246 0.031 Uiso 1 1 calc R U . . .
C39 C 0.17812(14) 0.16830(11) 0.54200(5) 0.0242(3) Uani 1 1 d . . . . .
H39A H 0.100565 0.145218 0.539449 0.029 Uiso 1 1 calc R U . . .
H39B H 0.247916 0.113935 0.531522 0.029 Uiso 1 1 calc R U . . .
C40 C 0.18600(12) 0.17263(10) 0.60029(5) 0.0213(2) Uani 1 1 d . . . . .
C41 C 0.22329(12) 0.04981(11) 0.68980(5) 0.0214(3) Uani 1 1 d . . . . .
C42 C 0.22992(13) -0.05656(11) 0.71626(5) 0.0228(3) Uani 1 1 d . . . . .
H42 H 0.231446 -0.108077 0.695607 0.027 Uiso 1 1 calc R U . . .
C43 C 0.23441(13) -0.09031(11) 0.77223(5) 0.0223(3) Uani 1 1 d . . . . .
C44 C 0.23557(12) -0.01345(11) 0.80207(5) 0.0211(2) Uani 1 1 d . . . . .
C45 C 0.23231(13) 0.09289(11) 0.77544(5) 0.0223(3) Uani 1 1 d . . . . .
H45 H 0.234906 0.144284 0.795584 0.027 Uiso 1 1 calc R U . . .
C46 C 0.22530(12) 0.12484(11) 0.71979(5) 0.0218(3) Uani 1 1 d . . . . .
H46 H 0.221892 0.197776 0.702253 0.026 Uiso 1 1 calc R U . . .
C47 C 0.23243(14) -0.20669(11) 0.79559(5) 0.0249(3) Uani 1 1 d . . . . .
C48 C 0.19531(18) -0.24607(12) 0.85439(6) 0.0360(4) Uani 1 1 d . . . . .
H48A H 0.264355 -0.251808 0.875764 0.054 Uiso 1 1 calc R U . . .
H48B H 0.173498 -0.316429 0.859817 0.054 Uiso 1 1 calc R U . . .
H48C H 0.123857 -0.195681 0.865961 0.054 Uiso 1 1 calc R U . . .
C49 C 0.22710(14) 0.02778(11) 0.88929(5) 0.0238(3) Uani 1 1 d . . . . .
H49A H 0.155208 0.085711 0.879130 0.029 Uiso 1 1 calc R U . . .
H49B H 0.301501 0.059569 0.885503 0.029 Uiso 1 1 calc R U . . .
C50 C 0.20487(13) -0.03491(11) 0.94666(5) 0.0229(3) Uani 1 1 d . . . . .
H50 H 0.270275 -0.101143 0.953194 0.027 Uiso 1 1 calc R U . . .
C51 C 0.21066(14) 0.03133(11) 0.98711(5) 0.0252(3) Uani 1 1 d . . . . .
H51A H 0.297228 0.037516 0.988446 0.030 Uiso 1 1 calc R U . . .
H51B H 0.161103 0.104151 0.975960 0.030 Uiso 1 1 calc R U . . .
C52 C 0.20461(13) 0.00621(11) 1.08843(5) 0.0234(3) Uani 1 1 d . . . . .
H52 H 0.296471 -0.016950 1.087825 0.028 Uiso 1 1 calc R U . . .
C53 C 0.14605(16) -0.05657(13) 1.13962(6) 0.0323(3) Uani 1 1 d . . . . .
H53A H 0.179287 -0.046366 1.171209 0.048 Uiso 1 1 calc R U . . .
H53B H 0.164793 -0.132688 1.138923 0.048 Uiso 1 1 calc R U . . .
H53C H 0.056309 -0.031157 1.141729 0.048 Uiso 1 1 calc R U . . .
C54 C 0.17127(15) 0.12608(11) 1.08441(6) 0.0284(3) Uani 1 1 d . . . . .
H54A H 0.082448 0.150821 1.080779 0.043 Uiso 1 1 calc R U . . .
H54B H 0.217534 0.162393 1.052736 0.043 Uiso 1 1 calc R U . . .
H54C H 0.192309 0.142381 1.117114 0.043 Uiso 1 1 calc R U . . .
N5 N 0.21542(11) 0.07509(9) 0.63327(4) 0.0224(2) Uani 1 1 d . . . . .
H5 H 0.2203(18) 0.0191(16) 0.6196(8) 0.032(5) Uiso 1 1 d . . . . .
N6 N 0.16108(11) -0.02169(9) 1.04144(4) 0.0209(2) Uani 1 1 d . . . . .
H6A H 0.076(2) -0.0007(16) 1.0434(8) 0.036(5) Uiso 1 1 d . . . . .
H6B H 0.1761(19) -0.0932(17) 1.0450(8) 0.037(5) Uiso 1 1 d . . . . .
O9 O 0.16696(10) 0.25777(8) 0.61486(4) 0.0251(2) Uani 1 1 d . . . . .
O10 O 0.25788(11) -0.26889(8) 0.76545(4) 0.0319(2) Uani 1 1 d . . . . .
O11 O 0.24421(10) -0.04864(8) 0.85646(4) 0.0249(2) Uani 1 1 d . . . . .
O12 O 0.08799(9) -0.06441(8) 0.95287(4) 0.02303(19) Uani 1 1 d . . . . .
H12 H 0.102(2) -0.140(2) 0.9647(9) 0.055(6) Uiso 1 1 d . . . . .
C55 C 0.84341(14) 0.29251(11) 0.96485(6) 0.0256(3) Uani 1 1 d . . . . .
C56 C 0.84425(14) 0.40772(11) 0.93834(6) 0.0255(3) Uani 1 1 d . . . . .
C57 C 0.85086(19) 0.48149(12) 0.96789(6) 0.0385(4) Uani 1 1 d . . . . .
H57 H 0.847770 0.462078 1.006240 0.046 Uiso 1 1 calc R U . . .
C58 C 0.8621(2) 0.58417(13) 0.94058(7) 0.0456(5) Uani 1 1 d . . . . .
H58 H 0.865935 0.636620 0.959863 0.055 Uiso 1 1 calc R U . . .
C59 C 0.86756(18) 0.60881(12) 0.88484(6) 0.0367(4) Uani 1 1 d . . . . .
H59 H 0.877058 0.678925 0.866407 0.044 Uiso 1 1 calc R U . . .
C60 C 0.84737(15) 0.44137(12) 0.88258(6) 0.0289(3) Uani 1 1 d . . . . .
H60 H 0.839883 0.391494 0.862364 0.035 Uiso 1 1 calc R U . . .
N7 N 0.86024(14) 0.53944(10) 0.85538(5) 0.0338(3) Uani 1 1 d . . . . .
O13 O 0.81927(11) 0.23477(8) 0.93696(4) 0.0322(2) Uani 1 1 d . . . . .
O14 O 0.87094(13) 0.26315(9) 1.01320(4) 0.0390(3) Uani 1 1 d . . . . .
C67 C 0.88620(14) 0.05659(11) 0.66208(5) 0.0254(3) Uani 1 1 d . . . . .
C68 C 0.89655(13) -0.05951(11) 0.68947(5) 0.0242(3) Uani 1 1 d . . . . .
C69 C 0.86581(16) -0.13186(12) 0.66449(6) 0.0310(3) Uani 1 1 d . . . . .
H69 H 0.842583 -0.110250 0.628432 0.037 Uiso 1 1 calc R U . . .
C70 C 0.86961(18) -0.23624(12) 0.69312(6) 0.0361(4) Uani 1 1 d . . . . .
H70 H 0.849598 -0.287706 0.676963 0.043 Uiso 1 1 calc R U . . .
C71 C 0.90301(17) -0.26414(12) 0.74555(6) 0.0350(3) Uani 1 1 d . . . . .
H71 H 0.904400 -0.335746 0.764956 0.042 Uiso 1 1 calc R U . . .
C72 C 0.93066(14) -0.09595(12) 0.74205(6) 0.0276(3) Uani 1 1 d . . . . .
H72 H 0.953414 -0.046666 0.758850 0.033 Uiso 1 1 calc R U . . .
N9 N 0.93353(14) -0.19620(11) 0.77061(5) 0.0349(3) Uani 1 1 d . . . . .
O17 O 0.83474(13) 0.08615(9) 0.61821(4) 0.0405(3) Uani 1 1 d . . . . .
O18 O 0.92499(11) 0.11529(8) 0.68490(4) 0.0336(2) Uani 1 1 d . . . . .
C61 C 0.53401(13) 0.60579(11) 0.64726(5) 0.0243(3) Uani 1 1 d . . . . .
C62 C 0.52297(13) 0.72310(11) 0.62207(5) 0.0232(3) Uani 1 1 d . . . . .
C63 C 0.54453(16) 0.79450(12) 0.65014(6) 0.0312(3) Uani 1 1 d . . . . .
H63 H 0.561210 0.771693 0.687089 0.037 Uiso 1 1 calc R U . . .
C64 C 0.54121(18) 0.89993(12) 0.62309(6) 0.0356(4) Uani 1 1 d . . . . .
H64 H 0.555012 0.950879 0.641286 0.043 Uiso 1 1 calc R U . . .
C65 C 0.51749(16) 0.92984(12) 0.56920(6) 0.0319(3) Uani 1 1 d . . . . .
H65 H 0.516997 1.002003 0.550915 0.038 Uiso 1 1 calc R U . . .
C66 C 0.49670(15) 0.76166(12) 0.56854(6) 0.0275(3) Uani 1 1 d . . . . .
H66 H 0.478567 0.713203 0.549864 0.033 Uiso 1 1 calc R U . . .
N8 N 0.49521(13) 0.86266(10) 0.54145(5) 0.0312(3) Uani 1 1 d . . . . .
O15 O 0.50249(11) 0.54869(8) 0.62109(4) 0.0337(2) Uani 1 1 d . . . . .
O16 O 0.57859(12) 0.57406(8) 0.69259(4) 0.0351(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5231(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5214(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5169(17) . ?
C4 N1 1.3596(17) . ?
C4 O1 1.2246(16) . ?
C5 C6 1.3892(19) . ?
C5 C10 1.3942(18) . ?
C5 N1 1.4142(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3950(18) . ?
C7 C8 1.4090(18) . ?
C7 C11 1.5047(19) . ?
C8 C9 1.3931(19) . ?
C8 O3 1.3665(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3885(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.4951(19) . ?
C11 O2 1.2166(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5171(18) . ?
C13 O3 1.4177(15) . ?
C14 H14 1.0000 . ?
C14 C15 1.5185(18) . ?
C14 O4 1.4113(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 N2 1.4899(16) . ?
C16 H16 1.0000 . ?
C16 C17 1.5178(19) . ?
C16 C18 1.5188(19) . ?
C16 N2 1.5027(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 H1 0.85(2) . ?
N2 H2C 0.925(19) . ?
N2 H2D 0.947(19) . ?
O4 H4 0.97(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C20 1.5230(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5208(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5194(17) . ?
C22 N3 1.3572(17) . ?
C22 O5 1.2281(16) . ?
C23 C24 1.3898(19) . ?
C23 C28 1.3970(18) . ?
C23 N3 1.4151(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.3964(18) . ?
C25 C26 1.4107(18) . ?
C25 C29 1.5032(18) . ?
C26 C27 1.3935(19) . ?
C26 O7 1.3629(15) . ?
C27 H27 0.9500 . ?
C27 C28 1.3908(18) . ?
C28 H28 0.9500 . ?
C29 C30 1.4998(19) . ?
C29 O6 1.2204(17) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.5193(18) . ?
C31 O7 1.4185(15) . ?
C32 H32 1.0000 . ?
C32 C33 1.5141(18) . ?
C32 O8 1.4170(16) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 N4 1.4902(16) . ?
C34 H34 1.0000 . ?
C34 C35 1.5180(19) . ?
C34 C36 1.5172(18) . ?
C34 N4 1.4979(16) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N3 H3 0.86(2) . ?
N4 H4A 0.92(2) . ?
N4 H4B 0.94(2) . ?
O8 H8 0.98(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C37 C38 1.5228(19) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.5217(18) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.5203(17) . ?
C40 N5 1.3526(17) . ?
C40 O9 1.2295(16) . ?
C41 C42 1.3889(19) . ?
C41 C46 1.3926(18) . ?
C41 N5 1.4133(16) . ?
C42 H42 0.9500 . ?
C42 C43 1.3969(18) . ?
C43 C44 1.4081(18) . ?
C43 C47 1.5057(18) . ?
C44 C45 1.3940(19) . ?
C44 O11 1.3655(15) . ?
C45 H45 0.9500 . ?
C45 C46 1.3911(18) . ?
C46 H46 0.9500 . ?
C47 C48 1.5016(19) . ?
C47 O10 1.2196(17) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 C50 1.5178(18) . ?
C49 O11 1.4247(15) . ?
C50 H50 1.0000 . ?
C50 C51 1.5192(18) . ?
C50 O12 1.4156(16) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 N6 1.4902(16) . ?
C52 H52 1.0000 . ?
C52 C53 1.5196(19) . ?
C52 C54 1.5183(19) . ?
C52 N6 1.5022(16) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
N5 H5 0.88(2) . ?
N6 H6A 0.93(2) . ?
N6 H6B 0.90(2) . ?
O12 H12 0.95(3) . ?
C55 C56 1.5039(19) . ?
C55 O13 1.2480(17) . ?
C55 O14 1.2611(18) . ?
C56 C57 1.384(2) . ?
C56 C60 1.3858(19) . ?
C57 H57 0.9500 . ?
C57 C58 1.386(2) . ?
C58 H58 0.9500 . ?
C58 C59 1.380(2) . ?
C59 H59 0.9500 . ?
C59 N7 1.336(2) . ?
C60 H60 0.9500 . ?
C60 N7 1.3370(19) . ?
C67 C68 1.5036(19) . ?
C67 O17 1.2647(18) . ?
C67 O18 1.2455(18) . ?
C68 C69 1.386(2) . ?
C68 C72 1.3880(19) . ?
C69 H69 0.9500 . ?
C69 C70 1.385(2) . ?
C70 H70 0.9500 . ?
C70 C71 1.380(2) . ?
C71 H71 0.9500 . ?
C71 N9 1.338(2) . ?
C72 H72 0.9500 . ?
C72 N9 1.3393(19) . ?
C61 C62 1.5053(19) . ?
C61 O15 1.2463(17) . ?
C61 O16 1.2617(18) . ?
C62 C63 1.3862(19) . ?
C62 C66 1.3868(19) . ?
C63 H63 0.9500 . ?
C63 C64 1.386(2) . ?
C64 H64 0.9500 . ?
C64 C65 1.383(2) . ?
C65 H65 0.9500 . ?
C65 N8 1.3375(19) . ?
C66 H66 0.9500 . ?
C66 N8 1.3386(19) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.53(11) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.51(11) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
N1 C4 C3 113.59(11) . . ?
O1 C4 C3 122.36(12) . . ?
O1 C4 N1 124.05(12) . . ?
C6 C5 C10 118.58(12) . . ?
C6 C5 N1 117.35(11) . . ?
C10 C5 N1 124.06(12) . . ?
C5 C6 H6 118.8 . . ?
C5 C6 C7 122.40(12) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C8 118.25(12) . . ?
C6 C7 C11 116.00(11) . . ?
C8 C7 C11 125.74(12) . . ?
C9 C8 C7 119.55(12) . . ?
O3 C8 C7 117.11(12) . . ?
O3 C8 C9 123.31(12) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.03(12) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.16(12) . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C7 121.83(12) . . ?
O2 C11 C7 118.64(12) . . ?
O2 C11 C12 119.51(13) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
O3 C13 H13A 110.7 . . ?
O3 C13 H13B 110.7 . . ?
O3 C13 C14 105.26(10) . . ?
C13 C14 H14 108.1 . . ?
C13 C14 C15 112.09(11) . . ?
C15 C14 H14 108.1 . . ?
O4 C14 C13 109.94(11) . . ?
O4 C14 H14 108.1 . . ?
O4 C14 C15 110.47(10) . . ?
C14 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
N2 C15 C14 108.70(10) . . ?
N2 C15 H15A 109.9 . . ?
N2 C15 H15B 109.9 . . ?
C17 C16 H16 108.7 . . ?
C17 C16 C18 112.32(11) . . ?
C18 C16 H16 108.7 . . ?
N2 C16 H16 108.7 . . ?
N2 C16 C17 107.45(11) . . ?
N2 C16 C18 110.78(11) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 N1 C5 128.45(11) . . ?
C4 N1 H1 118.3(13) . . ?
C5 N1 H1 113.2(13) . . ?
C15 N2 C16 115.74(10) . . ?
C15 N2 H2C 108.1(11) . . ?
C15 N2 H2D 109.5(11) . . ?
C16 N2 H2C 108.7(11) . . ?
C16 N2 H2D 110.8(11) . . ?
H2C N2 H2D 103.2(15) . . ?
C8 O3 C13 119.81(10) . . ?
C14 O4 H4 105.0(15) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 111.90(11) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 C20 113.64(11) . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
N3 C22 C21 113.73(11) . . ?
O5 C22 C21 122.34(12) . . ?
O5 C22 N3 123.93(12) . . ?
C24 C23 C28 118.78(12) . . ?
C24 C23 N3 117.11(11) . . ?
C28 C23 N3 124.10(12) . . ?
C23 C24 H24 118.8 . . ?
C23 C24 C25 122.40(12) . . ?
C25 C24 H24 118.8 . . ?
C24 C25 C26 118.12(12) . . ?
C24 C25 C29 116.49(11) . . ?
C26 C25 C29 125.39(12) . . ?
C27 C26 C25 119.68(12) . . ?
O7 C26 C25 117.07(11) . . ?
O7 C26 C27 123.22(12) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.12(12) . . ?
C28 C27 H27 119.4 . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.87(12) . . ?
C27 C28 H28 120.1 . . ?
C30 C29 C25 122.29(12) . . ?
O6 C29 C25 118.45(12) . . ?
O6 C29 C30 119.25(12) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H31A C31 H31B 108.9 . . ?
C32 C31 H31A 110.8 . . ?
C32 C31 H31B 110.8 . . ?
O7 C31 H31A 110.8 . . ?
O7 C31 H31B 110.8 . . ?
O7 C31 C32 104.77(10) . . ?
C31 C32 H32 108.5 . . ?
C33 C32 C31 110.71(11) . . ?
C33 C32 H32 108.5 . . ?
O8 C32 C31 109.91(11) . . ?
O8 C32 H32 108.5 . . ?
O8 C32 C33 110.51(10) . . ?
C32 C33 H33A 109.9 . . ?
C32 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
N4 C33 C32 109.03(11) . . ?
N4 C33 H33A 109.9 . . ?
N4 C33 H33B 109.9 . . ?
C35 C34 H34 108.6 . . ?
C36 C34 H34 108.6 . . ?
C36 C34 C35 112.91(11) . . ?
N4 C34 H34 108.6 . . ?
N4 C34 C35 107.27(11) . . ?
N4 C34 C36 110.67(11) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C22 N3 C23 128.53(11) . . ?
C22 N3 H3 116.2(13) . . ?
C23 N3 H3 115.2(13) . . ?
C33 N4 C34 115.32(10) . . ?
C33 N4 H4A 110.1(12) . . ?
C33 N4 H4B 107.6(12) . . ?
C34 N4 H4A 111.6(13) . . ?
C34 N4 H4B 107.9(11) . . ?
H4A N4 H4B 103.5(17) . . ?
C26 O7 C31 119.44(10) . . ?
C32 O8 H8 107.2(16) . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
C37 C38 H38A 109.2 . . ?
C37 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?
C39 C38 C37 111.98(12) . . ?
C39 C38 H38A 109.2 . . ?
C39 C38 H38B 109.2 . . ?
C38 C39 H39A 108.9 . . ?
C38 C39 H39B 108.9 . . ?
H39A C39 H39B 107.7 . . ?
C40 C39 C38 113.45(11) . . ?
C40 C39 H39A 108.9 . . ?
C40 C39 H39B 108.9 . . ?
N5 C40 C39 113.44(11) . . ?
O9 C40 C39 121.95(12) . . ?
O9 C40 N5 124.61(12) . . ?
C42 C41 C46 118.95(12) . . ?
C42 C41 N5 117.22(11) . . ?
C46 C41 N5 123.83(12) . . ?
C41 C42 H42 118.9 . . ?
C41 C42 C43 122.20(12) . . ?
C43 C42 H42 118.9 . . ?
C42 C43 C44 118.19(12) . . ?
C42 C43 C47 116.14(11) . . ?
C44 C43 C47 125.62(12) . . ?
C45 C44 C43 119.73(12) . . ?
O11 C44 C43 117.29(11) . . ?
O11 C44 C45 122.94(11) . . ?
C44 C45 H45 119.5 . . ?
C46 C45 C44 120.95(12) . . ?
C46 C45 H45 119.5 . . ?
C41 C46 H46 120.0 . . ?
C45 C46 C41 119.94(12) . . ?
C45 C46 H46 120.0 . . ?
C48 C47 C43 121.29(12) . . ?
O10 C47 C43 118.74(12) . . ?
O10 C47 C48 119.92(13) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
H49A C49 H49B 108.8 . . ?
C50 C49 H49A 110.8 . . ?
C50 C49 H49B 110.8 . . ?
O11 C49 H49A 110.8 . . ?
O11 C49 H49B 110.8 . . ?
O11 C49 C50 104.90(10) . . ?
C49 C50 H50 108.9 . . ?
C49 C50 C51 110.50(11) . . ?
C51 C50 H50 108.9 . . ?
O12 C50 C49 109.14(11) . . ?
O12 C50 H50 108.9 . . ?
O12 C50 C51 110.39(11) . . ?
C50 C51 H51A 109.9 . . ?
C50 C51 H51B 109.9 . . ?
H51A C51 H51B 108.3 . . ?
N6 C51 C50 108.95(11) . . ?
N6 C51 H51A 109.9 . . ?
N6 C51 H51B 109.9 . . ?
C53 C52 H52 108.9 . . ?
C54 C52 H52 108.9 . . ?
C54 C52 C53 112.63(12) . . ?
N6 C52 H52 108.9 . . ?
N6 C52 C53 107.14(11) . . ?
N6 C52 C54 110.35(11) . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C40 N5 C41 128.26(11) . . ?
C40 N5 H5 117.5(12) . . ?
C41 N5 H5 113.6(12) . . ?
C51 N6 C52 115.15(11) . . ?
C51 N6 H6A 107.6(12) . . ?
C51 N6 H6B 110.6(13) . . ?
C52 N6 H6A 107.1(12) . . ?
C52 N6 H6B 110.3(13) . . ?
H6A N6 H6B 105.6(18) . . ?
C44 O11 C49 119.05(10) . . ?
C50 O12 H12 106.6(15) . . ?
O13 C55 C56 117.65(12) . . ?
O13 C55 O14 126.34(13) . . ?
O14 C55 C56 115.98(12) . . ?
C57 C56 C55 121.70(13) . . ?
C57 C56 C60 117.83(13) . . ?
C60 C56 C55 120.31(12) . . ?
C56 C57 H57 120.6 . . ?
C56 C57 C58 118.85(14) . . ?
C58 C57 H57 120.6 . . ?
C57 C58 H58 120.6 . . ?
C59 C58 C57 118.77(14) . . ?
C59 C58 H58 120.6 . . ?
C58 C59 H59 118.2 . . ?
N7 C59 C58 123.58(14) . . ?
N7 C59 H59 118.2 . . ?
C56 C60 H60 117.9 . . ?
N7 C60 C56 124.28(13) . . ?
N7 C60 H60 117.9 . . ?
C59 N7 C60 116.67(13) . . ?
O17 C67 C68 116.07(12) . . ?
O18 C67 C68 117.97(13) . . ?
O18 C67 O17 125.93(13) . . ?
C69 C68 C67 121.41(12) . . ?
C69 C68 C72 118.02(13) . . ?
C72 C68 C67 120.46(12) . . ?
C68 C69 H69 120.6 . . ?
C70 C69 C68 118.72(13) . . ?
C70 C69 H69 120.6 . . ?
C69 C70 H70 120.6 . . ?
C71 C70 C69 118.80(14) . . ?
C71 C70 H70 120.6 . . ?
C70 C71 H71 118.1 . . ?
N9 C71 C70 123.80(14) . . ?
N9 C71 H71 118.1 . . ?
C68 C72 H72 117.9 . . ?
N9 C72 C68 124.15(13) . . ?
N9 C72 H72 117.9 . . ?
C71 N9 C72 116.51(13) . . ?
O15 C61 C62 117.70(12) . . ?
O15 C61 O16 126.09(13) . . ?
O16 C61 C62 116.17(12) . . ?
C63 C62 C61 121.78(12) . . ?
C63 C62 C66 118.05(13) . . ?
C66 C62 C61 120.09(12) . . ?
C62 C63 H63 120.8 . . ?
C64 C63 C62 118.50(13) . . ?
C64 C63 H63 120.7 . . ?
C63 C64 H64 120.5 . . ?
C65 C64 C63 119.02(14) . . ?
C65 C64 H64 120.5 . . ?
C64 C65 H65 118.2 . . ?
N8 C65 C64 123.54(14) . . ?
N8 C65 H65 118.2 . . ?
C62 C66 H66 117.8 . . ?
N8 C66 C62 124.32(13) . . ?
N8 C66 H66 117.8 . . ?
C65 N8 C66 116.53(12) . . ?

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
C1 C2 C3 C4 -179.35(12) . . . . ?
C2 C3 C4 N1 172.15(12) . . . . ?
C2 C3 C4 O1 -7.8(2) . . . . ?
C3 C4 N1 C5 -173.50(13) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C5 C6 C7 C11 -178.61(13) . . . . ?
C6 C5 C10 C9 -1.4(2) . . . . ?
C6 C5 N1 C4 176.68(13) . . . . ?
C6 C7 C8 C9 -1.4(2) . . . . ?
C6 C7 C8 O3 176.70(12) . . . . ?
C6 C7 C11 C12 175.13(16) . . . . ?
C6 C7 C11 O2 -3.3(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C7 C8 O3 C13 176.33(12) . . . . ?
C8 C7 C11 C12 -4.0(2) . . . . ?
C8 C7 C11 O2 177.55(15) . . . . ?
C8 C9 C10 C5 0.5(2) . . . . ?
C9 C8 O3 C13 -5.6(2) . . . . ?
C10 C5 C6 C7 0.8(2) . . . . ?
C10 C5 N1 C4 -2.2(2) . . . . ?
C11 C7 C8 C9 177.67(13) . . . . ?
C11 C7 C8 O3 -4.2(2) . . . . ?
C13 C14 C15 N2 -170.74(11) . . . . ?
C14 C13 O3 C8 -178.85(12) . . . . ?
C14 C15 N2 C16 -153.07(11) . . . . ?
C17 C16 N2 C15 -179.56(11) . . . . ?
C18 C16 N2 C15 -56.53(15) . . . . ?
N1 C5 C6 C7 -178.11(13) . . . . ?
N1 C5 C10 C9 177.49(13) . . . . ?
O1 C4 N1 C5 6.4(2) . . . . ?
O3 C8 C9 C10 -177.10(13) . . . . ?
O3 C13 C14 C15 -173.07(11) . . . . ?
O3 C13 C14 O4 63.65(14) . . . . ?
O4 C14 C15 N2 -47.76(15) . . . . ?
C19 C20 C21 C22 177.03(12) . . . . ?
C20 C21 C22 N3 176.47(12) . . . . ?
C20 C21 C22 O5 -4.04(19) . . . . ?
C21 C22 N3 C23 -176.13(13) . . . . ?
C23 C24 C25 C26 0.3(2) . . . . ?
C23 C24 C25 C29 -179.82(13) . . . . ?
C24 C23 C28 C27 -1.6(2) . . . . ?
C24 C23 N3 C22 -178.59(14) . . . . ?
C24 C25 C26 C27 -1.5(2) . . . . ?
C24 C25 C26 O7 176.49(12) . . . . ?
C24 C25 C29 C30 171.01(14) . . . . ?
C24 C25 C29 O6 -8.7(2) . . . . ?
C25 C26 C27 C28 1.1(2) . . . . ?
C25 C26 O7 C31 178.97(12) . . . . ?
C26 C25 C29 C30 -9.2(2) . . . . ?
C26 C25 C29 O6 171.14(15) . . . . ?
C26 C27 C28 C23 0.4(2) . . . . ?
C27 C26 O7 C31 -3.1(2) . . . . ?
C28 C23 C24 C25 1.2(2) . . . . ?
C28 C23 N3 C22 2.4(2) . . . . ?
C29 C25 C26 C27 178.67(13) . . . . ?
C29 C25 C26 O7 -3.3(2) . . . . ?
C31 C32 C33 N4 -172.99(11) . . . . ?
C32 C31 O7 C26 179.96(12) . . . . ?
C32 C33 N4 C34 -154.16(11) . . . . ?
C35 C34 N4 C33 176.62(11) . . . . ?
C36 C34 N4 C33 -59.80(15) . . . . ?
N3 C23 C24 C25 -177.88(13) . . . . ?
N3 C23 C28 C27 177.44(13) . . . . ?
O5 C22 N3 C23 4.4(2) . . . . ?
O7 C26 C27 C28 -176.72(13) . . . . ?
O7 C31 C32 C33 -170.19(11) . . . . ?
O7 C31 C32 O8 67.45(13) . . . . ?
O8 C32 C33 N4 -50.97(15) . . . . ?
C37 C38 C39 C40 -175.20(12) . . . . ?
C38 C39 C40 N5 -163.73(12) . . . . ?
C38 C39 C40 O9 16.29(19) . . . . ?
C39 C40 N5 C41 -175.98(13) . . . . ?
C41 C42 C43 C44 -1.8(2) . . . . ?
C41 C42 C43 C47 175.87(13) . . . . ?
C42 C41 C46 C45 -0.8(2) . . . . ?
C42 C41 N5 C40 166.92(13) . . . . ?
C42 C43 C44 C45 0.0(2) . . . . ?
C42 C43 C44 O11 -177.84(12) . . . . ?
C42 C43 C47 C48 -159.66(14) . . . . ?
C42 C43 C47 O10 18.0(2) . . . . ?
C43 C44 C45 C46 1.4(2) . . . . ?
C43 C44 O11 C49 -170.67(12) . . . . ?
C44 C43 C47 C48 17.8(2) . . . . ?
C44 C43 C47 O10 -164.56(14) . . . . ?
C44 C45 C46 C41 -0.9(2) . . . . ?
C45 C44 O11 C49 11.59(19) . . . . ?
C46 C41 C42 C43 2.2(2) . . . . ?
C46 C41 N5 C40 -13.4(2) . . . . ?
C47 C43 C44 C45 -177.40(13) . . . . ?
C47 C43 C44 O11 4.8(2) . . . . ?
C49 C50 C51 N6 167.37(11) . . . . ?
C50 C49 O11 C44 163.77(11) . . . . ?
C50 C51 N6 C52 156.79(11) . . . . ?
C53 C52 N6 C51 -179.12(12) . . . . ?
C54 C52 N6 C51 57.94(16) . . . . ?
N5 C41 C42 C43 -178.13(12) . . . . ?
N5 C41 C46 C45 179.53(13) . . . . ?
O9 C40 N5 C41 4.0(2) . . . . ?
O11 C44 C45 C46 179.04(12) . . . . ?
O11 C49 C50 C51 168.63(11) . . . . ?
O11 C49 C50 O12 -69.80(13) . . . . ?
O12 C50 C51 N6 46.55(15) . . . . ?
C55 C56 C57 C58 174.47(17) . . . . ?
C55 C56 C60 N7 -173.30(15) . . . . ?
C56 C57 C58 C59 -0.7(3) . . . . ?
C56 C60 N7 C59 -1.6(3) . . . . ?
C57 C56 C60 N7 2.2(3) . . . . ?
C57 C58 C59 N7 1.3(3) . . . . ?
C58 C59 N7 C60 -0.2(3) . . . . ?
C60 C56 C57 C58 -1.0(3) . . . . ?
O13 C55 C56 C57 169.79(16) . . . . ?
O13 C55 C56 C60 -14.9(2) . . . . ?
O14 C55 C56 C57 -12.1(2) . . . . ?
O14 C55 C56 C60 163.17(15) . . . . ?
C67 C68 C69 C70 -175.87(15) . . . . ?
C67 C68 C72 N9 175.07(14) . . . . ?
C68 C69 C70 C71 0.4(3) . . . . ?
C68 C72 N9 C71 1.1(2) . . . . ?
C69 C68 C72 N9 -1.3(2) . . . . ?
C69 C70 C71 N9 -0.7(3) . . . . ?
C70 C71 N9 C72 0.0(3) . . . . ?
C72 C68 C69 C70 0.5(2) . . . . ?
O17 C67 C68 C69 7.9(2) . . . . ?
O17 C67 C68 C72 -168.33(14) . . . . ?
O18 C67 C68 C69 -174.14(14) . . . . ?
O18 C67 C68 C72 9.6(2) . . . . ?
C61 C62 C63 C64 175.48(15) . . . . ?
C61 C62 C66 N8 -174.23(14) . . . . ?
C62 C63 C64 C65 -0.5(3) . . . . ?
C62 C66 N8 C65 -1.9(2) . . . . ?
C63 C62 C66 N8 2.6(2) . . . . ?
C63 C64 C65 N8 1.2(3) . . . . ?
C64 C65 N8 C66 0.0(3) . . . . ?
C66 C62 C63 C64 -1.3(2) . . . . ?
O15 C61 C62 C63 173.75(14) . . . . ?
O15 C61 C62 C66 -9.6(2) . . . . ?
O16 C61 C62 C63 -8.5(2) . . . . ?
O16 C61 C62 C66 168.20(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.734
_oxdiff_exptl_absorpt_empirical_full_min 0.628
####################################################################### 
# 
# 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_Ace
_database_code_depnum_ccdc_archive 'CCDC 2371674'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-07-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H28 N2 O4'
_chemical_formula_sum            'C18 H28 N2 O4'
_chemical_formula_weight         336.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.2863(2)
_cell_length_b                   12.5574(5)
_cell_length_c                   14.3948(5)
_cell_angle_alpha                68.479(4)
_cell_angle_beta                 80.815(3)
_cell_angle_gamma                86.522(3)
_cell_volume                     877.54(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6072
_cell_measurement_temperature    100.02(13)
_cell_measurement_theta_max      78.2400
_cell_measurement_theta_min      3.3330
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.119a (Rigaku Oxford Diffraction, 2024)
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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -7 -6 0.0306
-1 7 6 0.0306
0 -3 7 0.0171
0 -7 -6 0.0318
-3 -2 -2 0.0750
3 2 2 0.0451
0 7 7 0.0175
-1 -7 -6 0.0361
0 3 -7 0.0095

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
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
0.9645 -6.9837 -5.8879 -0.4645 -0.1957 -0.8637
-0.9645 6.9837 5.8879 0.4645 0.1957 0.8637
0.1989 -3.0918 6.7279 -0.3837 0.9234 0.0091
0.1753 -7.4484 -6.3643 -0.2685 -0.1086 -0.9572
-3.3982 -1.6192 -1.9427 0.8611 0.3567 -0.3624
3.3854 1.8134 2.1087 -0.8519 -0.3528 0.3870
0.1201 7.4410 6.6078 0.1841 0.0970 0.9781
-1.0230 -7.3711 -6.4261 0.0528 0.0320 -0.9981
-0.1839 3.2271 -6.6090 0.3837 -0.9234 0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13752
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.753
_diffrn_reflns_theta_min         3.337
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00  25.00   0.50    6.00    --  -47.63  94.00 -21.00  206
  2  ω    -78.00  25.00   0.50    6.00    --  -47.63  94.00 -21.00  206
  3  ω    -24.00  78.00   0.50    6.00    --   47.63 -94.00-131.00  204
  4  ω   -177.00 -83.00   0.50   25.00    -- -106.00 -94.00-131.00  188
  5  ω   -177.00 -83.00   0.50   25.00    -- -106.00 -94.00-131.00  188
  6  ω     41.00 106.00   0.50   25.00    --  112.88 -94.00-131.00  130
  7  ω    -27.00  28.00   0.50    6.00    --  -47.63  19.00-120.00  110
  8  ω    -27.00  28.00   0.50    6.00    --  -47.63  19.00 120.00  110
  9  ω    -93.00 -16.00   0.50    6.00    --  -47.63 125.00  90.00  154
 10  ω    -93.00 -16.00   0.50    6.00    --  -47.63 125.00  90.00  154
 11  ω    -27.00  28.00   0.50    6.00    --  -47.63  19.00   0.00  110
 12  ω     36.00 121.00   0.50    6.00    --   47.63  38.00   0.00  170
 13  ω   -177.00 -93.00   0.50   25.00    -- -106.00 -45.00 -90.00  168
 14  ω   -177.00 -93.00   0.50   25.00    -- -106.00 -46.00 -68.15  168
 15  ω   -112.00 -36.00   0.50   25.00    -- -106.00 125.00-180.00  152
 16  ω   -177.00-106.00   0.50   25.00    -- -106.00 -61.00 -30.00  142
 17  ω   -112.00 -36.00   0.50   25.00    -- -106.00 125.00 150.00  152
 18  ω   -120.00 -33.00   0.50   25.00    -- -106.00 136.00 104.95  174
 19  ω    -70.00 -33.00   0.50   25.00    -- -106.00  61.00  90.00   74
 20  ω   -177.00-106.00   0.50   25.00    -- -106.00 -61.00   0.00  142
 21  ω    -70.00 -33.00   0.50   25.00    -- -106.00  61.00   0.00   74
 22  ω   -106.00 -33.00   0.50   25.00    -- -106.00  94.00 -21.00  146
 23  ω   -112.00 -60.00   0.50   25.00    -- -106.00 125.00 -90.00  104
 24  ω   -176.00-114.00   0.50   25.00    -- -106.00 -77.00 -90.00  124
 25  ω     50.00  76.00   0.50   25.00    --  112.88 -77.00-150.00   52
 26  ω     41.00  68.00   0.50   25.00    --  112.88 -61.00  90.00   54
 27  ω     76.00 105.00   0.50   25.00    --  112.88 -95.00 150.00   58
 28  ω     43.00  71.00   0.50   25.00    --  112.88 -95.00 150.00   56
 29  ω     54.00  80.00   0.50   25.00    --  112.88 -77.00  60.00   52
 30  ω     71.00 100.00   0.50   25.00    --  112.88 -77.00  30.00   58
 31  ω     47.00  73.00   0.50   25.00    --  112.88 -61.00 120.00   52
 32  ω     43.00  83.00   0.50   25.00    --  112.88 -95.00 -60.00   80
 33  ω     41.00  73.00   0.50   25.00    --  112.88 -77.00  90.00   64
 34  ω     42.00  73.00   0.50   25.00    --  112.88 -61.00-150.00   62
 35  ω     56.00 105.00   0.50   25.00    --  112.88 -95.00  30.00   98
 36  ω     73.00 103.00   0.50   25.00    --  112.88 -95.00 -30.00   60
 37  ω    112.00 176.00   0.50   25.00    --  112.88  77.00 120.00  128
 38  ω     94.00 154.00   0.50   25.00    --  112.88  94.00 -21.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2634118000
_diffrn_orient_matrix_UB_12      0.0516406000
_diffrn_orient_matrix_UB_13      -0.0255126000
_diffrn_orient_matrix_UB_21      -0.1277696000
_diffrn_orient_matrix_UB_22      -0.0782178000
_diffrn_orient_matrix_UB_23      0.1050827000
_diffrn_orient_matrix_UB_31      0.0379357000
_diffrn_orient_matrix_UB_32      0.0927712000
_diffrn_orient_matrix_UB_33      0.0428657000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3330
_reflns_number_total             3623
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0792
_refine_ls_restrained_S_all      1.185
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0102P)²+1.9369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1760
_refine_special_details          ?
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O4 \\sim O4A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
3. Others
 Sof(H13C)=Sof(H13D)=Sof(N2A)=Sof(H2D)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15C)=
 Sof(H15D)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=
 Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(O4A)=Sof(H4B)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(N2)=Sof(H2C)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15A)=
 Sof(H15B)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(O4)=Sof(H4A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C16(H16), C14A(H14A), C16A(H16A)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C13(H13C,H13D), C15(H15A,H15B),
 C15A(H15C,H15D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.9055(7) 0.0593(3) 0.8322(3) 0.0422(8) Uani 1 1 d . . . . .
H1A H -0.996648 0.130077 0.798985 0.063 Uiso 1 1 calc R U . . .
H1B H -0.832384 0.066190 0.888157 0.063 Uiso 1 1 calc R U . . .
H1C H -1.025391 -0.005130 0.858300 0.063 Uiso 1 1 calc R U . . .
C2 C -0.6914(6) 0.0387(3) 0.7563(2) 0.0343(7) Uani 1 1 d . . . . .
H2A H -0.594509 -0.030834 0.790793 0.041 Uiso 1 1 calc R U . . .
H2B H -0.766674 0.025417 0.702813 0.041 Uiso 1 1 calc R U . . .
C3 C -0.5114(6) 0.1387(3) 0.7091(2) 0.0312(7) Uani 1 1 d . . . . .
H3A H -0.453628 0.156897 0.763703 0.037 Uiso 1 1 calc R U . . .
H3B H -0.607143 0.205922 0.669643 0.037 Uiso 1 1 calc R U . . .
C4 C -0.2767(6) 0.1210(2) 0.6404(2) 0.0287(6) Uani 1 1 d . . . . .
C5 C 0.0804(6) 0.2374(2) 0.5157(2) 0.0280(6) Uani 1 1 d . . . . .
C6 C 0.2008(6) 0.1549(3) 0.4797(2) 0.0300(7) Uani 1 1 d . . . . .
H6 H 0.130844 0.080168 0.503115 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4213(6) 0.1823(3) 0.4103(2) 0.0322(7) Uani 1 1 d . . . . .
H7 H 0.502204 0.125275 0.386896 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5286(6) 0.2911(3) 0.3736(2) 0.0298(6) Uani 1 1 d . . . . .
C9 C 0.4107(6) 0.3751(2) 0.4091(2) 0.0276(6) Uani 1 1 d . . . . .
C10 C 0.1895(6) 0.3454(2) 0.4802(2) 0.0275(6) Uani 1 1 d . . . . .
H10 H 0.110362 0.401313 0.505422 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4979(6) 0.4970(2) 0.3750(2) 0.0300(7) Uani 1 1 d . . . . .
C12 C 0.7568(6) 0.5347(3) 0.3146(3) 0.0350(7) Uani 1 1 d . . . . .
H12A H 0.888738 0.484470 0.349246 0.052 Uiso 1 1 calc R U . . .
H12B H 0.787723 0.613679 0.307404 0.052 Uiso 1 1 calc R U . . .
H12C H 0.762947 0.530526 0.247589 0.052 Uiso 1 1 calc R U . . .
C13 C 0.8377(7) 0.2495(3) 0.2500(3) 0.0416(9) Uani 1 1 d . . . . .
H13A H 0.700154 0.226987 0.221582 0.050 Uiso 0.736(8) 1 calc R U P A 1
H13B H 0.916858 0.179722 0.294273 0.050 Uiso 0.736(8) 1 calc R U P A 1
H13C H 0.692758 0.202295 0.251364 0.050 Uiso 0.264(8) 1 calc R U P A 2
H13D H 0.962556 0.196626 0.288717 0.050 Uiso 0.264(8) 1 calc R U P A 2
N1 N -0.1466(5) 0.2195(2) 0.5854(2) 0.0293(6) Uani 1 1 d . . . . .
H1 H -0.209(7) 0.286(3) 0.599(3) 0.048(11) Uiso 1 1 d . . . . .
O1 O -0.2111(4) 0.02656(18) 0.63788(17) 0.0340(5) Uani 1 1 d . . . . .
O2 O 0.3535(5) 0.56585(17) 0.39842(17) 0.0360(5) Uani 1 1 d . . . . .
O3 O 0.7421(5) 0.32293(19) 0.30318(18) 0.0395(6) Uani 1 1 d . . . . .
N2 N 1.3871(9) 0.3283(5) 0.0328(4) 0.0356(12) Uani 0.736(8) 1 d . . P A 1
H2C H 1.530(11) 0.352(5) 0.051(4) 0.027(14) Uiso 0.736(8) 1 d . . P A 1
C14 C 1.0386(11) 0.3250(4) 0.1660(4) 0.0319(12) Uani 0.736(8) 1 d . . P A 1
H14 H 1.152488 0.360563 0.195737 0.038 Uiso 0.736(8) 1 calc R U P A 1
C15 C 1.1967(9) 0.2554(4) 0.1129(3) 0.0338(12) Uani 0.736(8) 1 d . . P A 1
H15A H 1.284482 0.193089 0.161859 0.041 Uiso 0.736(8) 1 calc R U P A 1
H15B H 1.084092 0.220212 0.083352 0.041 Uiso 0.736(8) 1 calc R U P A 1
C16 C 1.4706(10) 0.2870(5) -0.0500(4) 0.0360(12) Uani 0.736(8) 1 d . . P A 1
H16 H 1.317895 0.286587 -0.082853 0.043 Uiso 0.736(8) 1 calc R U P A 1
C17 C 1.5808(11) 0.1651(5) -0.0149(4) 0.0410(13) Uani 0.736(8) 1 d . . P A 1
H17A H 1.740108 0.164637 0.011925 0.062 Uiso 0.736(8) 1 calc R U P A 1
H17B H 1.616032 0.139257 -0.072218 0.062 Uiso 0.736(8) 1 calc R U P A 1
H17C H 1.456487 0.113535 0.037956 0.062 Uiso 0.736(8) 1 calc R U P A 1
C18 C 1.662(2) 0.3701(8) -0.1272(7) 0.0441(19) Uani 0.736(8) 1 d . . P A 1
H18A H 1.585651 0.446746 -0.149721 0.066 Uiso 0.736(8) 1 calc R U P A 1
H18B H 1.710661 0.345974 -0.185091 0.066 Uiso 0.736(8) 1 calc R U P A 1
H18C H 1.814685 0.371688 -0.096955 0.066 Uiso 0.736(8) 1 calc R U P A 1
O4 O 0.9026(19) 0.4136(12) 0.0959(11) 0.038(2) Uani 0.736(8) 1 d . U P A 1
H4A H 1.015(13) 0.444(5) 0.058(5) 0.056 Uiso 0.736(8) 1 d . U P A 1
N2A N 1.411(3) 0.3782(12) 0.0585(9) 0.034(3) Uani 0.264(8) 1 d . . P A 2
H2D H 1.36(3) 0.450(14) 0.030(11) 0.041 Uiso 0.264(8) 1 d . U P A 2
C14A C 0.966(4) 0.3015(15) 0.1411(12) 0.038(4) Uani 0.264(8) 1 d . . P A 2
H14A H 0.964950 0.246091 0.105895 0.045 Uiso 0.264(8) 1 calc R U P A 2
C15A C 1.241(3) 0.3226(11) 0.1524(9) 0.036(4) Uani 0.264(8) 1 d . . P A 2
H15C H 1.233365 0.370156 0.194453 0.044 Uiso 0.264(8) 1 calc R U P A 2
H15D H 1.317926 0.248026 0.189233 0.044 Uiso 0.264(8) 1 calc R U P A 2
C16A C 1.426(3) 0.3268(12) -0.0203(16) 0.032(3) Uani 0.264(8) 1 d . . P A 2
H16A H 1.254700 0.332581 -0.043166 0.039 Uiso 0.264(8) 1 calc R U P A 2
C17A C 1.512(3) 0.1998(11) 0.0182(11) 0.038(4) Uani 0.264(8) 1 d . . P A 2
H17D H 1.646049 0.190299 0.060578 0.056 Uiso 0.264(8) 1 calc R U P A 2
H17E H 1.580209 0.177634 -0.039599 0.056 Uiso 0.264(8) 1 calc R U P A 2
H17F H 1.365583 0.151258 0.057842 0.056 Uiso 0.264(8) 1 calc R U P A 2
C18A C 1.630(6) 0.402(2) -0.112(2) 0.039(5) Uani 0.264(8) 1 d . . P A 2
H18D H 1.563510 0.479612 -0.140907 0.059 Uiso 0.264(8) 1 calc R U P A 2
H18E H 1.659736 0.367203 -0.163826 0.059 Uiso 0.264(8) 1 calc R U P A 2
H18F H 1.791029 0.404034 -0.087422 0.059 Uiso 0.264(8) 1 calc R U P A 2
O4A O 0.835(6) 0.405(4) 0.091(3) 0.049(7) Uani 0.264(8) 1 d . U P A 2
H4B H 0.68(4) 0.381(17) 0.099(15) 0.073 Uiso 0.264(8) 1 d . U P A 2


_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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.523(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.502(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.517(4) . ?
C4 N1 1.356(4) . ?
C4 O1 1.227(4) . ?
C5 C6 1.397(4) . ?
C5 C10 1.387(4) . ?
C5 N1 1.407(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(4) . ?
C8 C9 1.406(4) . ?
C8 O3 1.361(4) . ?
C9 C10 1.395(4) . ?
C9 C11 1.504(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.500(5) . ?
C11 O2 1.222(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C13 O3 1.425(4) . ?
C13 C14 1.537(6) . ?
C13 C14A 1.518(16) . ?
N1 H1 0.95(4) . ?
N2 H2C 0.93(6) . ?
N2 C15 1.465(6) . ?
N2 C16 1.463(7) . ?
C14 H14 1.0000 . ?
C14 C15 1.499(7) . ?
C14 O4 1.443(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 1.0000 . ?
C16 C17 1.535(8) . ?
C16 C18 1.505(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O4 H4A 0.75(7) . ?
N2A H2D 0.89(16) . ?
N2A C15A 1.453(17) . ?
N2A C16A 1.49(2) . ?
C14A H14A 1.0000 . ?
C14A C15A 1.54(2) . ?
C14A O4A 1.43(4) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16A H16A 1.0000 . ?
C16A C17A 1.551(18) . ?
C16A C18A 1.60(3) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
O4A H4B 0.9(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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.5(3) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C2 C3 C4 115.2(3) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
N1 C4 C3 112.8(3) . . ?
O1 C4 C3 122.7(3) . . ?
O1 C4 N1 124.5(3) . . ?
C6 C5 N1 124.8(3) . . ?
C10 C5 C6 118.3(3) . . ?
C10 C5 N1 116.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.8(3) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 119.1(3) . . ?
O3 C8 C7 123.9(3) . . ?
O3 C8 C9 116.9(3) . . ?
C8 C9 C11 125.7(3) . . ?
C10 C9 C8 118.2(3) . . ?
C10 C9 C11 116.1(3) . . ?
C5 C10 C9 122.6(3) . . ?
C5 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C12 C11 C9 121.4(3) . . ?
O2 C11 C9 118.5(3) . . ?
O2 C11 C12 120.0(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H13A C13 H13B 109.2 . . ?
H13C C13 H13D 107.0 . . ?
O3 C13 H13A 111.3 . . ?
O3 C13 H13B 111.3 . . ?
O3 C13 H13C 107.5 . . ?
O3 C13 H13D 107.5 . . ?
O3 C13 C14 102.5(3) . . ?
O3 C13 C14A 119.3(7) . . ?
C14 C13 H13A 111.3 . . ?
C14 C13 H13B 111.3 . . ?
C14A C13 H13C 107.5 . . ?
C14A C13 H13D 107.5 . . ?
C4 N1 C5 129.5(3) . . ?
C4 N1 H1 116(2) . . ?
C5 N1 H1 114(2) . . ?
C8 O3 C13 118.9(3) . . ?
C15 N2 H2C 118(3) . . ?
C16 N2 H2C 109(4) . . ?
C16 N2 C15 114.3(5) . . ?
C13 C14 H14 109.6 . . ?
C15 C14 C13 110.5(4) . . ?
C15 C14 H14 109.6 . . ?
O4 C14 C13 107.4(6) . . ?
O4 C14 H14 109.6 . . ?
O4 C14 C15 110.1(8) . . ?
N2 C15 C14 110.0(4) . . ?
N2 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 H16 107.8 . . ?
N2 C16 C17 113.3(4) . . ?
N2 C16 C18 108.8(5) . . ?
C17 C16 H16 107.8 . . ?
C18 C16 H16 107.8 . . ?
C18 C16 C17 111.1(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 O4 H4A 99(5) . . ?
C15A N2A H2D 109(9) . . ?
C15A N2A C16A 116.7(14) . . ?
C16A N2A H2D 105(9) . . ?
C13 C14A H14A 110.6 . . ?
C13 C14A C15A 102.7(11) . . ?
C15A C14A H14A 110.6 . . ?
O4A C14A C13 109(2) . . ?
O4A C14A H14A 110.6 . . ?
O4A C14A C15A 113.0(18) . . ?
N2A C15A C14A 115.5(12) . . ?
N2A C15A H15C 108.4 . . ?
N2A C15A H15D 108.4 . . ?
C14A C15A H15C 108.4 . . ?
C14A C15A H15D 108.4 . . ?
H15C C15A H15D 107.5 . . ?
N2A C16A H16A 109.6 . . ?
N2A C16A C17A 112.1(14) . . ?
N2A C16A C18A 105.9(12) . . ?
C17A C16A H16A 109.6 . . ?
C17A C16A C18A 110.1(15) . . ?
C18A C16A H16A 109.6 . . ?
C16A C17A H17D 109.5 . . ?
C16A C17A H17E 109.5 . . ?
C16A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C16A C18A H18D 109.5 . . ?
C16A C18A H18E 109.5 . . ?
C16A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C14A O4A H4B 103(10) . . ?

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
C1 C2 C3 C4 174.0(3) . . . . ?
C2 C3 C4 N1 168.4(3) . . . . ?
C2 C3 C4 O1 -13.3(4) . . . . ?
C3 C4 N1 C5 178.6(3) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C6 C5 C10 C9 1.2(5) . . . . ?
C6 C5 N1 C4 8.7(5) . . . . ?
C6 C7 C8 C9 0.8(5) . . . . ?
C6 C7 C8 O3 -178.3(3) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C7 C8 C9 C11 -178.2(3) . . . . ?
C7 C8 O3 C13 11.7(5) . . . . ?
C8 C9 C10 C5 -1.0(4) . . . . ?
C8 C9 C11 C12 -13.5(5) . . . . ?
C8 C9 C11 O2 167.1(3) . . . . ?
C9 C8 O3 C13 -167.3(3) . . . . ?
C10 C5 C6 C7 -0.4(5) . . . . ?
C10 C5 N1 C4 -171.7(3) . . . . ?
C10 C9 C11 C12 168.2(3) . . . . ?
C10 C9 C11 O2 -11.1(4) . . . . ?
C11 C9 C10 C5 177.4(3) . . . . ?
C13 C14 C15 N2 179.8(4) . . . . ?
C13 C14A C15A N2A -177.1(11) . . . . ?
N1 C5 C6 C7 179.1(3) . . . . ?
N1 C5 C10 C9 -178.4(3) . . . . ?
O1 C4 N1 C5 0.5(5) . . . . ?
O3 C8 C9 C10 179.1(3) . . . . ?
O3 C8 C9 C11 0.9(5) . . . . ?
O3 C13 C14 C15 169.4(4) . . . . ?
O3 C13 C14 O4 -70.5(8) . . . . ?
O3 C13 C14A C15A 82.8(10) . . . . ?
O3 C13 C14A O4A -37(2) . . . . ?
C14 C13 O3 C8 169.2(3) . . . . ?
C15 N2 C16 C17 -56.7(6) . . . . ?
C15 N2 C16 C18 179.2(6) . . . . ?
C16 N2 C15 C14 -154.1(5) . . . . ?
O4 C14 C15 N2 61.4(7) . . . . ?
C14A C13 O3 C8 146.8(9) . . . . ?
C15A N2A C16A C17A -58.0(18) . . . . ?
C15A N2A C16A C18A -178.1(14) . . . . ?
C16A N2A C15A C14A -51.5(17) . . . . ?
O4A C14A C15A N2A -60(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.692
####################################################################### 
# 
# 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_AteINA
_database_code_depnum_ccdc_archive 'CCDC 2371678'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H23 N2 O3, C6 H4 N O2, C2 H3 N'
_chemical_formula_sum            'C22 H30 N4 O5'
_chemical_formula_weight         430.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H Cl O N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.4840(2)
_cell_length_b                   14.6742(2)
_cell_length_c                   8.34950(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.1200(10)
_cell_angle_gamma                90
_cell_volume                     2264.70(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15069
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.4710
_cell_measurement_theta_min      2.3640
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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_special_details   ?
_exptl_crystal_colour            'clear brown'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 9 0 0.0280
0 0 -5 0.0785
-5 -9 0 0.0224
0 0 5 0.0954
3 9 1 0.0341
-4 -9 0 0.0244
2 9 0 0.0243
-1 -9 0 0.0224
0 10 0 0.0206
0 -10 0 0.0224
-1 9 0 0.0187
1 -9 0 0.0262
-3 9 0 0.0168
5 -8 -2 0.0432
5 -8 1 0.0400
8 -7 1 0.0504
-8 6 2 0.0337
-10 5 -1 0.0172
10 -5 0 0.0318
-10 5 -1 0.0114
11 -4 0 0.0318
-11 3 -1 0.0132
12 -2 0 0.0318
10 -1 3 0.0670
12 2 0 0.0337
-1 9 2 0.0460
-11 2 2 0.0368
-10 -3 3 0.0529
11 4 1 0.0444

_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.043
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
4.7429 8.7517 -0.0407 0.7936 -0.6084 0.0092
0.1161 -0.1099 -5.4196 0.0079 -0.0047 -1.0000
-4.7429 -8.7517 0.0407 -0.7936 0.6084 -0.0092
-0.1750 -0.0707 5.4195 -0.0251 0.0142 0.9996
3.4993 8.9903 0.8442 0.8398 -0.5144 0.1735
-3.5465 -9.0779 -0.3684 -0.8497 0.5203 -0.0859
2.3481 9.3415 -0.0530 0.9027 -0.4301 0.0092
-1.1054 -9.4842 0.0575 -0.9427 0.3334 -0.0092
-0.1494 9.5231 -0.0609 0.9724 -0.2330 0.0092
0.1494 -9.5231 0.0609 -0.9724 0.2330 -0.0092
-1.4026 9.4576 -0.0631 0.9915 -0.1301 0.0092
1.3947 -9.4259 0.4490 -0.9896 0.1298 0.0620
-2.6404 9.2886 -0.0640 0.9996 -0.0257 0.0092
4.7886 -8.2768 -1.5840 -0.9341 -0.1733 -0.3120
4.9221 -8.4734 1.0752 -0.9674 -0.1799 0.1780
7.8581 -6.7169 1.4576 -0.8504 -0.4624 0.2511
-8.5000 5.9675 1.7620 0.7745 0.5325 0.3415
-9.5627 5.3320 -1.2118 0.7434 0.6357 -0.2080
9.7936 -5.4953 0.0371 -0.7601 -0.6497 -0.0092
-10.3247 4.5630 -0.9195 0.6796 0.7169 -0.1554
11.0207 -3.7582 0.0200 -0.6084 -0.7936 -0.0091
-11.3442 2.7699 -0.7766 0.5175 0.8454 -0.1324
11.7661 -1.8569 -0.0001 -0.4301 -0.9027 -0.0091
10.3443 -0.6561 2.7116 -0.2895 -0.8197 0.4943
11.7043 2.1023 -0.0456 -0.0257 -0.9996 -0.0090
-1.3009 8.5794 2.2795 0.8907 -0.1165 0.4394
-10.8283 1.7749 2.1118 0.3942 0.8284 0.3980
-9.7321 -2.5163 2.8382 -0.0679 0.8500 0.5223
10.5493 3.9175 1.3009 0.1773 -0.9535 0.2438

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            31464
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.098
_diffrn_reflns_theta_min         2.390
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -69.00   0.50    3.79    --  -47.76-132.00 130.00  102
  2  ω    -91.00 -17.00   0.50    3.79    --  -47.76 132.00-159.00  148
  3  ω   -120.00 -65.00   0.50    3.79    --  -47.76-138.00 -45.00  110
  4  ω     38.00  99.00   0.50    3.79    --   47.76-132.00 130.00  122
  5  ω   -158.00 -65.00   0.50   15.16    --  -91.75-138.00 -45.00  186
  6  ω    -96.00 -20.00   0.50   15.16    --  -91.75 138.00  16.00  152
  7  ω     42.00 121.00   0.50   15.16    --  107.31-138.00 -45.00  158
  8  ω     91.00 178.00   0.50   15.16    --  107.31 132.00-159.00  174
  9  ω     38.00 117.00   0.50   15.16    --  107.31-132.00 130.00  158
 10  ω     87.00 175.00   0.50   15.16    --  107.31 138.00  16.00  176
 11  ω    -25.00  28.00   0.50    3.79    --  -47.76  19.00  90.00  106
 12  ω   -120.00 -73.00   0.50    3.79    --  -47.76-125.00 -90.00   94
 13  ω   -120.00 -73.00   0.50    3.79    --  -47.76-125.00-120.00   94
 14  ω   -120.00 -33.00   0.50    3.79    --  -47.76 -57.00 -60.00  174
 15  ω    -25.00  28.00   0.50    3.79    --  -47.76  19.00 -30.00  106
 16  ω    -41.00  25.00   0.50    3.79    --  -47.76  38.00-150.00  132
 17  ω   -163.00 -77.00   0.50   15.16    --  -91.75 -57.00-120.00  172
 18  ω   -165.00 -78.00   0.50   15.16    --  -91.75 -38.00-180.00  174
 19  ω     35.00 107.00   0.50   15.16    --  107.31 -77.00-180.00  144
 20  ω     94.00 178.00   0.50   15.16    --  107.31  38.00 -60.00  168
 21  ω     35.00 106.00   0.50   15.16    --  107.31 -99.00   0.00  142
 22  ω     35.00 106.00   0.50   15.16    --  107.31 -99.00 -30.00  142
 23  ω     35.00 106.00   0.50   15.16    --  107.31 -99.00 -60.00  142
 24  ω     95.00 178.00   0.50   15.16    --  107.31  19.00-150.00  166
 25  ω     92.00 178.00   0.50   15.16    --  107.31  57.00 120.00  172
 26  ω   -120.00 -25.00   0.50    3.79    --  -47.76 -77.00-150.00  190
 27  ω   -120.00 -76.00   0.50    3.79    --  -47.76 -77.00  30.00   88
 28  ω   -120.00 -33.00   0.50    3.79    --  -47.76 -57.00  60.00  174
;
_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      -0.0204942000
_diffrn_orient_matrix_UB_12      0.1017657000
_diffrn_orient_matrix_UB_13      -0.0039680000
_diffrn_orient_matrix_UB_21      -0.0807849000
_diffrn_orient_matrix_UB_22      -0.0257381000
_diffrn_orient_matrix_UB_23      -0.0003329000
_diffrn_orient_matrix_UB_31      -0.0004336000
_diffrn_orient_matrix_UB_32      0.0021432000
_diffrn_orient_matrix_UB_33      0.1844560000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3937
_reflns_number_total             4594
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4594
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.8202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.68928(7) 0.69335(9) 0.48230(15) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.65187(7) 0.64327(10) 0.34593(15) 0.0246(3) Uani 1 1 d . . . . .
H2A H 0.667561 0.669678 0.242577 0.029 Uiso 1 1 calc R U . . .
H2B H 0.666550 0.578394 0.347613 0.029 Uiso 1 1 calc R U . . .
C3 C 0.57004(7) 0.64951(9) 0.35844(15) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.53358(7) 0.60936(9) 0.48417(16) 0.0246(3) Uani 1 1 d . . . . .
H4 H 0.560524 0.577132 0.562900 0.030 Uiso 1 1 calc R U . . .
C5 C 0.45865(7) 0.61444(9) 0.49964(15) 0.0239(3) Uani 1 1 d . . . . .
H5 H 0.435003 0.586261 0.587580 0.029 Uiso 1 1 calc R U . . .
C6 C 0.41922(7) 0.66108(9) 0.38517(16) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.45451(8) 0.70059(11) 0.25573(17) 0.0313(3) Uani 1 1 d . . . . .
H7 H 0.427374 0.731307 0.175462 0.038 Uiso 1 1 calc R U . . .
C8 C 0.52914(8) 0.69533(10) 0.24339(17) 0.0287(3) Uani 1 1 d . . . . .
H8 H 0.552767 0.723350 0.155265 0.034 Uiso 1 1 calc R U . . .
C9 C 0.30674(7) 0.63672(10) 0.52314(16) 0.0253(3) Uani 1 1 d . . . . .
H9A H 0.331637 0.652936 0.624303 0.030 Uiso 1 1 calc R U . . .
H9B H 0.303112 0.569523 0.516261 0.030 Uiso 1 1 calc R U . . .
C10 C 0.23230(7) 0.67958(9) 0.51691(16) 0.0233(3) Uani 1 1 d . . . . .
H10 H 0.209307 0.665480 0.411259 0.028 Uiso 1 1 calc R U . . .
C11 C 0.23765(7) 0.78239(9) 0.53683(16) 0.0237(3) Uani 1 1 d . . . . .
H11A H 0.261181 0.797011 0.640307 0.028 Uiso 1 1 calc R U . . .
H11B H 0.267463 0.808435 0.449742 0.028 Uiso 1 1 calc R U . . .
C12 C 0.16101(7) 0.92465(9) 0.51302(16) 0.0260(3) Uani 1 1 d . . . . .
H12 H 0.189956 0.941877 0.416607 0.031 Uiso 1 1 calc R U . . .
C13 C 0.19267(9) 0.97284(10) 0.65813(18) 0.0329(3) Uani 1 1 d . . . . .
H13A H 0.163295 0.959087 0.752664 0.049 Uiso 1 1 calc R U . . .
H13B H 0.192799 1.038769 0.639404 0.049 Uiso 1 1 calc R U . . .
H13C H 0.242348 0.951755 0.675935 0.049 Uiso 1 1 calc R U . . .
C14 C 0.08243(8) 0.95103(11) 0.48375(19) 0.0330(3) Uani 1 1 d . . . . .
H14A H 0.064699 0.920452 0.386985 0.049 Uiso 1 1 calc R U . . .
H14B H 0.078958 1.017189 0.469725 0.049 Uiso 1 1 calc R U . . .
H14C H 0.053062 0.932420 0.575692 0.049 Uiso 1 1 calc R U . . .
N1 N 0.71527(6) 0.77603(8) 0.44726(14) 0.0251(2) Uani 1 1 d . . . . .
H1A H 0.7414(10) 0.8065(13) 0.527(2) 0.041(5) Uiso 1 1 d . . . . .
H1B H 0.7150(9) 0.7955(13) 0.344(2) 0.039(5) Uiso 1 1 d . . . . .
N2 N 0.16369(6) 0.82273(8) 0.53201(14) 0.0226(2) Uani 1 1 d . . . . .
H2C H 0.1384(9) 0.8049(12) 0.625(2) 0.032(4) Uiso 1 1 d . . . . .
H2D H 0.1385(10) 0.7938(13) 0.444(2) 0.039(5) Uiso 1 1 d . . . . .
O1 O 0.69314(5) 0.65914(7) 0.61746(11) 0.0295(2) Uani 1 1 d . . . . .
O2 O 0.34548(5) 0.67219(7) 0.38846(11) 0.0281(2) Uani 1 1 d . . . . .
O3 O 0.18995(5) 0.64087(7) 0.64149(11) 0.0265(2) Uani 1 1 d . . . . .
H3 H 0.1413(12) 0.6353(15) 0.598(3) 0.059(6) Uiso 1 1 d . . . . .
C15 C 0.04274(7) 0.66662(9) 0.38618(15) 0.0219(3) Uani 1 1 d . . . . .
C16 C -0.03410(7) 0.66299(9) 0.32175(15) 0.0221(3) Uani 1 1 d . . . . .
C17 C -0.08224(7) 0.59510(9) 0.36899(15) 0.0223(3) Uani 1 1 d . . . . .
H17 H -0.068209 0.550184 0.444877 0.027 Uiso 1 1 calc R U . . .
C18 C -0.15125(7) 0.59456(9) 0.30261(16) 0.0238(3) Uani 1 1 d . . . . .
H18 H -0.183723 0.547913 0.334978 0.029 Uiso 1 1 calc R U . . .
C19 C -0.12778(8) 0.72184(10) 0.15402(17) 0.0298(3) Uani 1 1 d . . . . .
H19 H -0.143494 0.766916 0.080048 0.036 Uiso 1 1 calc R U . . .
C20 C -0.05783(7) 0.72782(10) 0.21277(16) 0.0267(3) Uani 1 1 d . . . . .
H20 H -0.026630 0.775505 0.179009 0.032 Uiso 1 1 calc R U . . .
N3 N -0.17474(6) 0.65609(8) 0.19541(13) 0.0257(2) Uani 1 1 d . . . . .
O4 O 0.05788(5) 0.61900(7) 0.50563(11) 0.0272(2) Uani 1 1 d . . . . .
O5 O 0.08598(5) 0.71939(7) 0.31302(11) 0.0254(2) Uani 1 1 d . . . . .
C21 C 0.39000(9) 0.98764(11) 0.48575(18) 0.0342(3) Uani 1 1 d . . . . .
C22 C 0.41901(10) 1.04083(12) 0.61729(19) 0.0400(4) Uani 1 1 d . . . . .
H22A H 0.444665 1.094025 0.574834 0.060 Uiso 1 1 calc R U . . .
H22B H 0.452649 1.003278 0.679694 0.060 Uiso 1 1 calc R U . . .
H22C H 0.379341 1.061168 0.686289 0.060 Uiso 1 1 calc R U . . .
N4 N 0.36743(9) 0.94514(11) 0.38294(17) 0.0473(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5203(18) . ?
C1 N1 1.3376(18) . ?
C1 O1 1.2370(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5190(18) . ?
C3 C4 1.3808(19) . ?
C3 C8 1.3942(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.3933(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3820(18) . ?
C6 C7 1.390(2) . ?
C6 O2 1.3731(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.3856(19) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5137(18) . ?
C9 O2 1.4323(16) . ?
C10 H10 1.0000 . ?
C10 C11 1.5210(19) . ?
C10 O3 1.4216(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N2 1.4903(16) . ?
C12 H12 1.0000 . ?
C12 C13 1.519(2) . ?
C12 C14 1.5223(19) . ?
C12 N2 1.5049(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 H1A 0.94(2) . ?
N1 H1B 0.91(2) . ?
N2 H2C 0.947(18) . ?
N2 H2D 0.968(19) . ?
O3 H3 0.97(2) . ?
C15 C16 1.5186(18) . ?
C15 O4 1.2491(16) . ?
C15 O5 1.2703(16) . ?
C16 C17 1.3934(19) . ?
C16 C20 1.3870(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3897(18) . ?
C18 H18 0.9500 . ?
C18 N3 1.3429(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3846(19) . ?
C19 N3 1.3437(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.449(2) . ?
C21 N4 1.139(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 115.96(12) . . ?
O1 C1 C2 120.82(12) . . ?
O1 C1 N1 123.20(12) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 111.76(10) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C4 C3 C2 120.95(12) . . ?
C4 C3 C8 117.69(12) . . ?
C8 C3 C2 121.35(12) . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.32(12) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.03(12) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C7 119.77(12) . . ?
O2 C6 C5 124.54(12) . . ?
O2 C6 C7 115.69(12) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.23(13) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 119.5 . . ?
C7 C8 C3 120.94(13) . . ?
C7 C8 H8 119.5 . . ?
H9A C9 H9B 108.7 . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
O2 C9 H9A 110.5 . . ?
O2 C9 H9B 110.5 . . ?
O2 C9 C10 106.13(10) . . ?
C9 C10 H10 109.2 . . ?
C9 C10 C11 110.46(11) . . ?
C11 C10 H10 109.2 . . ?
O3 C10 C9 108.10(10) . . ?
O3 C10 H10 109.2 . . ?
O3 C10 C11 110.61(11) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
N2 C11 C10 109.37(10) . . ?
N2 C11 H11A 109.8 . . ?
N2 C11 H11B 109.8 . . ?
C13 C12 H12 108.6 . . ?
C13 C12 C14 112.06(12) . . ?
C14 C12 H12 108.6 . . ?
N2 C12 H12 108.6 . . ?
N2 C12 C13 111.47(11) . . ?
N2 C12 C14 107.50(11) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 H1A 117.5(11) . . ?
C1 N1 H1B 119.5(12) . . ?
H1A N1 H1B 121.9(16) . . ?
C11 N2 C12 115.32(10) . . ?
C11 N2 H2C 108.8(10) . . ?
C11 N2 H2D 106.6(11) . . ?
C12 N2 H2C 110.2(10) . . ?
C12 N2 H2D 109.8(11) . . ?
H2C N2 H2D 105.6(15) . . ?
C6 O2 C9 118.06(10) . . ?
C10 O3 H3 105.9(13) . . ?
O4 C15 C16 118.10(11) . . ?
O4 C15 O5 125.79(12) . . ?
O5 C15 C16 116.10(11) . . ?
C17 C16 C15 121.48(12) . . ?
C20 C16 C15 120.18(12) . . ?
C20 C16 C17 118.34(12) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.52(12) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 118.1 . . ?
N3 C18 C17 123.87(12) . . ?
N3 C18 H18 118.1 . . ?
C20 C19 H19 118.1 . . ?
N3 C19 H19 118.1 . . ?
N3 C19 C20 123.89(13) . . ?
C16 C20 H20 120.6 . . ?
C19 C20 C16 118.87(13) . . ?
C19 C20 H20 120.6 . . ?
C18 N3 C19 116.49(12) . . ?
N4 C21 C22 179.39(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -65.38(16) . . . . ?
C1 C2 C3 C8 115.00(14) . . . . ?
C2 C3 C4 C5 179.52(12) . . . . ?
C2 C3 C8 C7 179.94(13) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C3 C8 C7 0.3(2) . . . . ?
C4 C5 C6 C7 1.1(2) . . . . ?
C4 C5 C6 O2 -178.85(12) . . . . ?
C5 C6 C7 C8 -1.6(2) . . . . ?
C5 C6 O2 C9 2.95(19) . . . . ?
C6 C7 C8 C3 0.9(2) . . . . ?
C7 C6 O2 C9 -177.01(13) . . . . ?
C8 C3 C4 C5 -0.9(2) . . . . ?
C9 C10 C11 N2 -179.40(10) . . . . ?
C10 C9 O2 C6 165.39(11) . . . . ?
C10 C11 N2 C12 -166.83(11) . . . . ?
C13 C12 N2 C11 -65.78(14) . . . . ?
C14 C12 N2 C11 171.04(11) . . . . ?
N1 C1 C2 C3 -100.78(14) . . . . ?
O1 C1 C2 C3 77.50(16) . . . . ?
O2 C6 C7 C8 178.32(13) . . . . ?
O2 C9 C10 C11 -63.32(14) . . . . ?
O2 C9 C10 O3 175.53(10) . . . . ?
O3 C10 C11 N2 -59.75(13) . . . . ?
C15 C16 C17 C18 -178.55(12) . . . . ?
C15 C16 C20 C19 178.90(13) . . . . ?
C16 C17 C18 N3 -0.3(2) . . . . ?
C17 C16 C20 C19 -0.8(2) . . . . ?
C17 C18 N3 C19 -0.9(2) . . . . ?
C20 C16 C17 C18 1.15(18) . . . . ?
C20 C19 N3 C18 1.3(2) . . . . ?
N3 C19 C20 C16 -0.5(2) . . . . ?
O4 C15 C16 C17 -14.02(18) . . . . ?
O4 C15 C16 C20 166.28(12) . . . . ?
O5 C15 C16 C17 166.63(12) . . . . ?
O5 C15 C16 C20 -13.06(18) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.729
_oxdiff_exptl_absorpt_empirical_full_min 0.572
####################################################################### 
# 
# 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_AceINA
_database_code_depnum_ccdc_archive 'CCDC 2371676'
loop_
_audit_author_name
_audit_author_address
'Delbert Botes'
;University of Missouri
United States of America
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H29 N2 O4, C6 H4 N O2'
_chemical_formula_sum            'C24 H33 N3 O6'
_chemical_formula_weight         459.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.2068(2)
_cell_length_b                   13.1295(2)
_cell_length_c                   25.6226(4)
_cell_angle_alpha                75.5690(10)
_cell_angle_beta                 81.5610(10)
_cell_angle_gamma                75.4320(10)
_cell_volume                     3519.52(10)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    33855
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      78.2480
_cell_measurement_theta_min      3.6150
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.119a (Rigaku Oxford Diffraction, 2024)
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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1476
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0222
1 1 16 0.0309
-7 -1 -1 0.0297
-2 -8 -6 0.1181
4 8 4 0.0438
7 1 5 0.0271
2 0 -15 0.0057
3 -1 -14 0.0038
5 7 -1 0.0254

_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.043
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0005 -0.0001 -0.0008 -0.0412 0.1290 -0.0449
1.0098 0.5743 16.3391 -0.9435 -0.2812 0.1753
-7.2247 -1.2722 -1.1891 -0.2526 0.8537 -0.4553
-1.8994 -8.4825 -5.6851 0.0865 -0.3002 -0.9499
3.9778 8.0781 4.2992 0.0752 0.0194 0.9970
6.9948 0.7381 5.3379 -0.0216 -0.9115 0.4108
1.5439 -0.0964 -15.3660 0.9996 -0.0251 -0.0091
2.8024 -0.5345 -14.2272 0.9726 -0.2324 0.0091
5.2849 6.7090 -0.5458 0.3954 -0.1909 0.8985

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            96708
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.868
_diffrn_reflns_theta_min         3.567
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -59.00   0.50    1.50    --  -47.63-146.00 165.00  122
  2  ω    -93.00 -13.00   0.50    1.50    --  -47.63 125.00  49.00  160
  3  ω    -93.00 -13.00   0.50    1.50    --  -47.63 125.00  49.00  160
  4  ω   -107.00 -24.00   0.50    1.50    --  -47.63 146.00-143.00  166
  5  ω     13.00  93.00   0.50    1.50    --   47.63-125.00 -27.00  160
  6  ω     24.00 108.00   0.50    1.50    --   47.63-146.00 165.00  168
  7  ω     59.00 120.00   0.50    1.50    --   47.63 146.00-143.00  122
  8  ω   -112.00 -36.00   0.50    6.02    -- -106.00 125.00  49.00  152
  9  ω   -127.00 -33.00   0.50    6.02    -- -106.00 146.00-143.00  188
 10  ω   -176.00 -73.00   0.50    6.02    -- -106.00-125.00 -27.00  206
 11  ω     59.00 169.00   0.50    6.02    --  112.88 146.00-143.00  220
 12  ω     41.00 127.00   0.50    6.02    --  112.88-146.00 165.00  172
 13  ω     74.00 178.00   0.50    6.02    --  112.88 125.00  49.00  208
 14  ω     43.00 112.00   0.50    6.02    --  112.88-125.00 -27.00  138
 15  ω    -27.00  28.00   0.50    1.50    --  -47.63  19.00  60.00  110
 16  ω    -27.00  28.00   0.50    1.50    --  -47.63  19.00-180.00  110
 17  ω    -42.00  25.00   0.50    1.50    --  -47.63  38.00 150.00  134
 18  ω    -27.00  28.00   0.50    1.50    --  -47.63  19.00-150.00  110
 19  ω    -24.00  63.00   0.50    1.50    --   47.63 -57.00-150.00  174
 20  ω    -27.00  30.00   0.50    1.50    --   47.63 -19.00 150.00  114
 21  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00 -90.00   74
 22  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00 150.00   74
 23  ω   -177.00 -95.00   0.50    6.02    -- -106.00 -51.00  19.55  164
 24  ω   -177.00-106.00   0.50    6.02    -- -106.00 -61.00  90.00  142
 25  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00  30.00   74
 26  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00  90.00   74
 27  ω   -126.00 -33.00   0.50    6.02    -- -106.00 144.00 -39.64  186
 28  ω   -177.00-110.00   0.50    6.02    -- -106.00 -77.00 -30.00  134
 29  ω   -169.00 -59.00   0.50    6.02    -- -106.00-146.00 165.00  220
 30  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00-180.00   74
 31  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00-150.00   74
 32  ω   -126.00 -33.00   0.50    6.02    -- -106.00 144.00 -39.64  186
 33  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00  60.00   74
 34  ω   -177.00 -92.00   0.50    6.02    -- -106.00 -44.00  44.60  170
 35  ω   -112.00 -36.00   0.50    6.02    -- -106.00 125.00 120.00  152
 36  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00   0.00   74
 37  ω    -70.00 -33.00   0.50    6.02    -- -106.00  61.00-120.00   74
 38  ω     41.00 105.00   0.50    6.02    --  112.88 -95.00-180.00  128
 39  ω     41.00  73.00   0.50    6.02    --  112.88 -61.00-120.00   64
 40  ω     41.00 105.00   0.50    6.02    --  112.88 -95.00   0.00  128
 41  ω    106.00 178.00   0.50    6.02    --  112.88  61.00 120.00  144
 42  ω     43.00 112.00   0.50    6.02    --  112.88-125.00-150.00  138
 43  ω     41.00 105.00   0.50    6.02    --  112.88 -95.00-150.00  128
 44  ω     41.00  73.00   0.50    6.02    --  112.88 -61.00-150.00   64
 45  ω    106.00 178.00   0.50    6.02    --  112.88  61.00-150.00  144
 46  ω    106.00 178.00   0.50    6.02    --  112.88  61.00 120.00  144
 47  ω     41.00 104.00   0.50    6.02    --  112.88 -77.00 -60.00  126
 48  ω    106.00 178.00   0.50    6.02    --  112.88  61.00 -60.00  144
 49  ω    106.00 178.00   0.50    6.02    --  112.88  61.00 -60.00  144
 50  ω     41.00 104.00   0.50    6.02    --  112.88 -77.00 -30.00  126
 51  ω     35.00 120.00   0.50    1.50    --   47.63  47.00-137.79  170
 52  ω     35.00 120.00   0.50    1.50    --   47.63  47.00 -48.31  170
 53  ω     35.00 120.00   0.50    1.50    --   47.63  47.00  47.13  170
 54  ω     35.00 120.00   0.50    1.50    --   47.63  46.00 164.17  170
 55  ω     35.00 120.00   0.50    1.50    --   47.63  46.00 -98.48  170
 56  ω     35.00 119.00   0.50    1.50    --   47.63  45.00   3.19  168
 57  ω     35.00 104.00   0.50    1.50    --   47.63  46.00  69.35  138
 58  ω     35.00 119.00   0.50    1.50    --   47.63  45.00 125.88  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0412247000
_diffrn_orient_matrix_UB_12      0.0214936000
_diffrn_orient_matrix_UB_13      -0.0610485000
_diffrn_orient_matrix_UB_21      -0.1289361000
_diffrn_orient_matrix_UB_22      0.0721556000
_diffrn_orient_matrix_UB_23      -0.0117762000
_diffrn_orient_matrix_UB_31      0.0448656000
_diffrn_orient_matrix_UB_32      0.0989407000
_diffrn_orient_matrix_UB_33      0.0044803000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12962
_reflns_number_total             14782
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     956
_refine_ls_number_reflns         14782
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.086
_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)+(0.0790P)²+3.3880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1734
_refine_special_details          ?
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-C14A \\sim O4-C14
 with sigma of 0.02
 C15-C14 \\sim C15-C14A
 with sigma of 0.02
 C14-C13 \\sim C13-C14A
 with sigma of 0.02
3. Others
 Fixed Sof: H13A(0.9) H13B(0.9) H13C(0.1) H13D(0.1) C14(0.9) H14(0.9)
 C14A(0.1) H14A(0.1) H15A(0.9) H15B(0.9) H15C(0.1) H15D(0.1)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C14A(H14A), C16(H16), C32(H32), C34(H34), C50(H50), C52(H52)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C13(H13C,H13D), C15(H15A,H15B),
 C15(H15C,H15D), C20(H20A,H20B), C21(H21A,H21B), C31(H31A,H31B), C33(H33A,H33B),
  C38(H38A,H38B), C39(H39A,H39B), C49(H49A,H49B), C51(H51A,H51B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C24(H24), C27(H27), C28(H28), C42(H42), C45(H45),
 C46(H46), C55(H55), C56(H56), C58(H58), C59(H59), C61(H61), C62(H62), C64(H64),
  C65(H65), C67(H67), C68(H68), C70(H70), C71(H71)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C30(H30A,H30B,H30C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C37(H37A,H37B,H37C), C48(H48A,H48B,H48C), C53(H53A,H53B,H53C),
 C54(H54A,H54B,H54C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4241(2) 0.05948(18) 1.24188(8) 0.0275(5) Uani 1 1 d . . . . .
H1A H 0.355693 0.120681 1.246706 0.041 Uiso 1 1 calc R U . . .
H1B H 0.501183 0.072319 1.249933 0.041 Uiso 1 1 calc R U . . .
H1C H 0.407220 -0.006599 1.266463 0.041 Uiso 1 1 calc R U . . .
C2 C 0.4368(2) 0.04713(16) 1.18377(8) 0.0230(4) Uani 1 1 d . . . . .
H2A H 0.362318 0.026556 1.176907 0.028 Uiso 1 1 calc R U . . .
H2B H 0.509472 -0.011474 1.178332 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4520(2) 0.15114(16) 1.14366(8) 0.0210(4) Uani 1 1 d . . . . .
H3A H 0.376533 0.208060 1.147743 0.025 Uiso 1 1 calc R U . . .
H3B H 0.522420 0.174378 1.152740 0.025 Uiso 1 1 calc R U . . .
C4 C 0.47434(18) 0.14150(15) 1.08526(8) 0.0178(4) Uani 1 1 d . . . . .
C5 C 0.49327(18) 0.25789(15) 0.99246(8) 0.0188(4) Uani 1 1 d . . . . .
C6 C 0.49769(18) 0.36269(16) 0.96516(8) 0.0199(4) Uani 1 1 d . . . . .
H6 H 0.496245 0.414320 0.985593 0.024 Uiso 1 1 calc R U . . .
C7 C 0.50418(18) 0.39495(15) 0.90883(8) 0.0192(4) Uani 1 1 d . . . . .
C8 C 0.50592(19) 0.31779(15) 0.87896(8) 0.0189(4) Uani 1 1 d . . . . .
C9 C 0.50339(19) 0.21160(15) 0.90624(8) 0.0194(4) Uani 1 1 d . . . . .
H9 H 0.505731 0.159357 0.886058 0.023 Uiso 1 1 calc R U . . .
C10 C 0.49751(19) 0.18148(15) 0.96230(8) 0.0198(4) Uani 1 1 d . . . . .
H10 H 0.496372 0.109014 0.980188 0.024 Uiso 1 1 calc R U . . .
C11 C 0.50905(19) 0.51107(16) 0.88512(8) 0.0216(4) Uani 1 1 d . . . . .
C12 C 0.5254(2) 0.55469(17) 0.82530(9) 0.0284(5) Uani 1 1 d . . . . .
H12A H 0.595101 0.506838 0.809318 0.043 Uiso 1 1 calc R U . . .
H12B H 0.541970 0.626931 0.818265 0.043 Uiso 1 1 calc R U . . .
H12C H 0.449733 0.558838 0.809184 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5137(2) 0.27644(18) 0.79240(8) 0.0267(5) Uani 1 1 d D . . . .
H13A H 0.440536 0.243838 0.801738 0.032 Uiso 0.9 1 calc R U P A 1
H13B H 0.589428 0.218195 0.797865 0.032 Uiso 0.9 1 calc R U P A 1
H13C H 0.427066 0.276849 0.788298 0.032 Uiso 0.1 1 calc R U P B 2
H13D H 0.548903 0.204473 0.814474 0.032 Uiso 0.1 1 calc R U P B 2
C14 C 0.5161(2) 0.34150(17) 0.73432(9) 0.0186(4) Uani 0.9 1 d D . P C 1
H14 H 0.447989 0.407977 0.732072 0.022 Uiso 0.9 1 calc R U P C 1
C14A C 0.5834(18) 0.2822(16) 0.7356(6) 0.034(5) Uiso 0.1 1 d D . P C 2
H14A H 0.653621 0.217400 0.737195 0.041 Uiso 0.1 1 calc R U P C 2
C15 C 0.4958(2) 0.27786(19) 0.69637(9) 0.0281(5) Uani 1 1 d D . . . .
H15A H 0.553711 0.206208 0.702397 0.034 Uiso 0.9 1 calc R U P C 1
H15B H 0.410206 0.266718 0.703406 0.034 Uiso 0.9 1 calc R U P C 1
H15C H 0.502480 0.201244 0.696315 0.034 Uiso 0.1 1 calc R U P C 2
H15D H 0.409988 0.307042 0.710271 0.034 Uiso 0.1 1 calc R U P C 2
C16 C 0.4516(2) 0.30931(16) 0.59969(9) 0.0234(4) Uani 1 1 d . . . . .
H16 H 0.360651 0.325450 0.610630 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4756(2) 0.38218(19) 0.54501(9) 0.0295(5) Uani 1 1 d . . . . .
H17A H 0.563849 0.364524 0.532780 0.044 Uiso 1 1 calc R U . . .
H17B H 0.451239 0.457657 0.548160 0.044 Uiso 1 1 calc R U . . .
H17C H 0.427109 0.371442 0.518754 0.044 Uiso 1 1 calc R U . . .
C18 C 0.4941(2) 0.19020(17) 0.59926(10) 0.0293(5) Uani 1 1 d . . . . .
H18A H 0.454463 0.174656 0.571378 0.044 Uiso 1 1 calc R U . . .
H18B H 0.470928 0.147180 0.634722 0.044 Uiso 1 1 calc R U . . .
H18C H 0.584167 0.171881 0.591421 0.044 Uiso 1 1 calc R U . . .
N1 N 0.48338(17) 0.23557(14) 1.04958(7) 0.0209(4) Uani 1 1 d . . . . .
H1 H 0.480(3) 0.289(2) 1.0618(11) 0.030(7) Uiso 1 1 d . . . . .
N2 N 0.51655(17) 0.33729(14) 0.63961(7) 0.0194(3) Uani 1 1 d . . . . .
H2C H 0.498(3) 0.409(2) 0.6365(11) 0.032(7) Uiso 1 1 d . . . . .
H2D H 0.602(3) 0.321(2) 0.6290(11) 0.033(7) Uiso 1 1 d . . . . .
O1 O 0.48317(14) 0.05607(11) 1.07173(6) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.49915(16) 0.57119(12) 0.91596(6) 0.0299(4) Uani 1 1 d . . . . .
O3 O 0.50756(15) 0.35127(11) 0.82414(6) 0.0253(3) Uani 1 1 d . . . . .
O4 O 0.63169(14) 0.37330(12) 0.71971(6) 0.0224(3) Uani 1 1 d D . . . .
H4 H 0.611(3) 0.443(3) 0.7095(14) 0.058(10) Uiso 1 1 d . . . D 1
C19 C 0.8398(2) 0.63689(19) 0.07327(9) 0.0308(5) Uani 1 1 d . . . . .
H19A H 0.856647 0.702782 0.048506 0.046 Uiso 1 1 calc R U . . .
H19B H 0.760959 0.625488 0.066315 0.046 Uiso 1 1 calc R U . . .
H19C H 0.906508 0.575120 0.067560 0.046 Uiso 1 1 calc R U . . .
C20 C 0.8323(2) 0.64818(17) 0.13135(9) 0.0257(4) Uani 1 1 d . . . . .
H20A H 0.909613 0.665302 0.137447 0.031 Uiso 1 1 calc R U . . .
H20B H 0.762668 0.708742 0.137441 0.031 Uiso 1 1 calc R U . . .
C21 C 0.8138(2) 0.54548(17) 0.17148(8) 0.0252(4) Uani 1 1 d . . . . .
H21A H 0.737278 0.528184 0.164574 0.030 Uiso 1 1 calc R U . . .
H21B H 0.883900 0.485461 0.165129 0.030 Uiso 1 1 calc R U . . .
C22 C 0.80417(19) 0.55204(16) 0.23024(8) 0.0210(4) Uani 1 1 d . . . . .
C23 C 0.80886(19) 0.43044(16) 0.32217(8) 0.0200(4) Uani 1 1 d . . . . .
C24 C 0.8159(2) 0.32320(16) 0.34869(8) 0.0219(4) Uani 1 1 d . . . . .
H24 H 0.813685 0.272558 0.328257 0.026 Uiso 1 1 calc R U . . .
C25 C 0.8261(2) 0.28740(16) 0.40407(8) 0.0218(4) Uani 1 1 d . . . . .
C26 C 0.8303(2) 0.36283(16) 0.43408(8) 0.0210(4) Uani 1 1 d . . . . .
C27 C 0.8216(2) 0.47106(16) 0.40770(8) 0.0215(4) Uani 1 1 d . . . . .
H27 H 0.823084 0.522275 0.427917 0.026 Uiso 1 1 calc R U . . .
C28 C 0.81083(19) 0.50478(15) 0.35244(8) 0.0200(4) Uani 1 1 d . . . . .
H28 H 0.804769 0.578638 0.335181 0.024 Uiso 1 1 calc R U . . .
C29 C 0.8304(2) 0.16933(16) 0.42684(9) 0.0248(4) Uani 1 1 d . . . . .
C30 C 0.8407(3) 0.1200(2) 0.48581(11) 0.0473(8) Uani 1 1 d . . . . .
H30A H 0.918708 0.126998 0.496048 0.071 Uiso 1 1 calc R U . . .
H30B H 0.839094 0.043490 0.492938 0.071 Uiso 1 1 calc R U . . .
H30C H 0.771134 0.157337 0.507053 0.071 Uiso 1 1 calc R U . . .
C31 C 0.8431(2) 0.39821(17) 0.52061(8) 0.0249(4) Uani 1 1 d . . . . .
H31A H 0.763659 0.452534 0.519511 0.030 Uiso 1 1 calc R U . . .
H31B H 0.911614 0.436088 0.508054 0.030 Uiso 1 1 calc R U . . .
C32 C 0.8583(2) 0.32959(17) 0.57736(9) 0.0245(4) Uani 1 1 d . . . . .
H32 H 0.933512 0.269900 0.575640 0.029 Uiso 1 1 calc R U . . .
C33 C 0.8771(2) 0.39288(17) 0.61623(8) 0.0246(4) Uani 1 1 d . . . . .
H33A H 0.958262 0.413042 0.606548 0.029 Uiso 1 1 calc R U . . .
H33B H 0.811584 0.459943 0.613920 0.029 Uiso 1 1 calc R U . . .
C34 C 0.9424(2) 0.35236(16) 0.71108(8) 0.0228(4) Uani 1 1 d . . . . .
H34 H 1.032230 0.339624 0.697828 0.027 Uiso 1 1 calc R U . . .
C35 C 0.8965(2) 0.46983(17) 0.71433(9) 0.0273(5) Uani 1 1 d . . . . .
H35A H 0.807470 0.484158 0.725460 0.041 Uiso 1 1 calc R U . . .
H35B H 0.911809 0.516199 0.678779 0.041 Uiso 1 1 calc R U . . .
H35C H 0.940480 0.484994 0.740869 0.041 Uiso 1 1 calc R U . . .
C36 C 0.9266(2) 0.27568(18) 0.76541(9) 0.0277(5) Uani 1 1 d . . . . .
H36A H 0.979520 0.284802 0.790383 0.041 Uiso 1 1 calc R U . . .
H36B H 0.950250 0.201163 0.760728 0.041 Uiso 1 1 calc R U . . .
H36C H 0.839948 0.291526 0.780210 0.041 Uiso 1 1 calc R U . . .
N3 N 0.80286(17) 0.45627(14) 0.26573(7) 0.0218(4) Uani 1 1 d . . . . .
H3 H 0.801(3) 0.401(2) 0.2537(11) 0.032(7) Uiso 1 1 d . . . . .
N4 N 0.87255(17) 0.32558(14) 0.67224(7) 0.0215(4) Uani 1 1 d . . . . .
H4A H 0.792(3) 0.335(2) 0.6855(11) 0.030(7) Uiso 1 1 d . . . . .
H4B H 0.903(3) 0.250(2) 0.6713(11) 0.033(7) Uiso 1 1 d . . . . .
O5 O 0.79806(15) 0.63684(11) 0.24388(6) 0.0252(3) Uani 1 1 d . . . . .
O6 O 0.82380(17) 0.11323(12) 0.39652(6) 0.0309(4) Uani 1 1 d . . . . .
O7 O 0.84512(17) 0.32538(12) 0.48794(6) 0.0295(4) Uani 1 1 d . . . . .
O8 O 0.75550(14) 0.28267(12) 0.59630(6) 0.0238(3) Uani 1 1 d . . . . .
H8 H 0.785(3) 0.209(3) 0.6058(15) 0.063(11) Uiso 1 1 d . . . . .
C37 C 0.8238(2) -0.2684(2) 0.55382(9) 0.0327(5) Uani 1 1 d . . . . .
H37A H 0.902919 -0.250287 0.554911 0.049 Uiso 1 1 calc R U . . .
H37B H 0.821394 -0.338529 0.578208 0.049 Uiso 1 1 calc R U . . .
H37C H 0.755756 -0.212877 0.565328 0.049 Uiso 1 1 calc R U . . .
C38 C 0.8102(2) -0.27364(18) 0.49641(9) 0.0276(5) Uani 1 1 d . . . . .
H38A H 0.878377 -0.330505 0.485178 0.033 Uiso 1 1 calc R U . . .
H38B H 0.731141 -0.293828 0.495722 0.033 Uiso 1 1 calc R U . . .
C39 C 0.8123(2) -0.16716(17) 0.45649(8) 0.0239(4) Uani 1 1 d . . . . .
H39A H 0.740330 -0.111740 0.466326 0.029 Uiso 1 1 calc R U . . .
H39B H 0.888233 -0.144263 0.459527 0.029 Uiso 1 1 calc R U . . .
C40 C 0.80885(19) -0.17207(16) 0.39830(8) 0.0199(4) Uani 1 1 d . . . . .
C41 C 0.77667(19) -0.04866(16) 0.30783(8) 0.0204(4) Uani 1 1 d . . . . .
C42 C 0.77200(19) 0.05790(16) 0.28073(8) 0.0216(4) Uani 1 1 d . . . . .
H42 H 0.773178 0.109312 0.300876 0.026 Uiso 1 1 calc R U . . .
C43 C 0.76565(19) 0.09182(16) 0.22491(8) 0.0216(4) Uani 1 1 d . . . . .
C44 C 0.76275(19) 0.01474(16) 0.19566(8) 0.0201(4) Uani 1 1 d . . . . .
C45 C 0.76522(19) -0.09182(16) 0.22289(8) 0.0219(4) Uani 1 1 d . . . . .
H45 H 0.761444 -0.143209 0.203187 0.026 Uiso 1 1 calc R U . . .
C46 C 0.77310(19) -0.12383(16) 0.27836(8) 0.0214(4) Uani 1 1 d . . . . .
H46 H 0.776062 -0.196962 0.296272 0.026 Uiso 1 1 calc R U . . .
C47 C 0.7696(2) 0.20797(16) 0.20089(9) 0.0234(4) Uani 1 1 d . . . . .
C48 C 0.7902(3) 0.24984(18) 0.14108(10) 0.0343(5) Uani 1 1 d . . . . .
H48A H 0.860212 0.200638 0.126112 0.052 Uiso 1 1 calc R U . . .
H48B H 0.808201 0.321571 0.133986 0.052 Uiso 1 1 calc R U . . .
H48C H 0.715596 0.254693 0.124024 0.052 Uiso 1 1 calc R U . . .
C49 C 0.7724(2) -0.02692(17) 0.10884(8) 0.0240(4) Uani 1 1 d . . . . .
H49A H 0.698987 -0.058265 0.113103 0.029 Uiso 1 1 calc R U . . .
H49B H 0.845440 -0.085966 0.118874 0.029 Uiso 1 1 calc R U . . .
C50 C 0.79336(19) 0.03549(16) 0.05132(8) 0.0222(4) Uani 1 1 d . . . . .
H50 H 0.726395 0.102684 0.044732 0.027 Uiso 1 1 calc R U . . .
C51 C 0.7905(2) -0.03100(17) 0.01123(8) 0.0238(4) Uani 1 1 d . . . . .
H51A H 0.840818 -0.104995 0.022904 0.029 Uiso 1 1 calc R U . . .
H51B H 0.704378 -0.035990 0.009930 0.029 Uiso 1 1 calc R U . . .
C52 C 0.8008(2) -0.01181(16) -0.08948(8) 0.0219(4) Uani 1 1 d . . . . .
H52 H 0.708856 0.013069 -0.089772 0.026 Uiso 1 1 calc R U . . .
C53 C 0.8614(3) 0.0472(2) -0.14123(9) 0.0324(5) Uani 1 1 d . . . . .
H53A H 0.951245 0.019318 -0.142638 0.049 Uiso 1 1 calc R U . . .
H53B H 0.842123 0.124553 -0.141909 0.049 Uiso 1 1 calc R U . . .
H53C H 0.829792 0.035793 -0.172525 0.049 Uiso 1 1 calc R U . . .
C54 C 0.8358(2) -0.13347(17) -0.08272(10) 0.0278(5) Uani 1 1 d . . . . .
H54A H 0.813759 -0.152578 -0.114098 0.042 Uiso 1 1 calc R U . . .
H54B H 0.791097 -0.167210 -0.049782 0.042 Uiso 1 1 calc R U . . .
H54C H 0.925115 -0.159211 -0.079899 0.042 Uiso 1 1 calc R U . . .
N5 N 0.78445(17) -0.07365(14) 0.36431(7) 0.0210(3) Uani 1 1 d . . . . .
H5 H 0.783(3) -0.018(2) 0.3790(12) 0.038(8) Uiso 1 1 d . . . . .
N6 N 0.84038(16) 0.01962(14) -0.04330(7) 0.0186(3) Uani 1 1 d . . . . .
H6A H 0.927(3) -0.001(2) -0.0450(10) 0.027(6) Uiso 1 1 d . . . . .
H6B H 0.823(2) 0.093(2) -0.0493(11) 0.028(7) Uiso 1 1 d . . . . .
O9 O 0.82783(15) -0.25822(11) 0.38416(6) 0.0256(3) Uani 1 1 d . . . . .
O10 O 0.75862(17) 0.26888(12) 0.23136(6) 0.0315(4) Uani 1 1 d . . . . .
O11 O 0.75335(15) 0.04991(11) 0.14144(6) 0.0249(3) Uani 1 1 d . . . . .
O12 O 0.90947(13) 0.06463(11) 0.04502(6) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.891(3) 0.143(3) 0.0323(14) 0.055(9) Uiso 1 1 d . . . . .
C55 C 0.5197(3) 0.90474(18) 0.62546(10) 0.0351(6) Uani 1 1 d . . . . .
H55 H 0.534015 0.950993 0.645930 0.042 Uiso 1 1 calc R U . . .
C56 C 0.5301(2) 0.79688(17) 0.65005(9) 0.0297(5) Uani 1 1 d . . . . .
H56 H 0.550908 0.770401 0.686359 0.036 Uiso 1 1 calc R U . . .
C57 C 0.50966(19) 0.72792(16) 0.62085(9) 0.0219(4) Uani 1 1 d . . . . .
C58 C 0.4780(2) 0.77177(17) 0.56847(9) 0.0266(4) Uani 1 1 d . . . . .
H58 H 0.461507 0.727545 0.547397 0.032 Uiso 1 1 calc R U . . .
C59 C 0.4706(2) 0.88071(18) 0.54696(9) 0.0292(5) Uani 1 1 d . . . . .
H59 H 0.450223 0.909131 0.510674 0.035 Uiso 1 1 calc R U . . .
C60 C 0.5262(2) 0.60810(16) 0.64469(9) 0.0238(4) Uani 1 1 d . . . . .
N7 N 0.4906(2) 0.94808(15) 0.57452(8) 0.0326(4) Uani 1 1 d . . . . .
O13 O 0.49544(18) 0.55308(12) 0.61805(7) 0.0352(4) Uani 1 1 d . . . . .
O14 O 0.57275(19) 0.57462(13) 0.68927(7) 0.0390(4) Uani 1 1 d . . . . .
C61 C 0.9313(2) -0.21760(18) 0.76288(9) 0.0303(5) Uani 1 1 d . . . . .
H61 H 0.956722 -0.246163 0.798394 0.036 Uiso 1 1 calc R U . . .
C62 C 0.9329(2) -0.11053(17) 0.73912(9) 0.0274(5) Uani 1 1 d . . . . .
H62 H 0.959935 -0.067667 0.757859 0.033 Uiso 1 1 calc R U . . .
C63 C 0.8944(2) -0.06735(16) 0.68767(9) 0.0245(4) Uani 1 1 d . . . . .
C64 C 0.8578(2) -0.13388(18) 0.66193(9) 0.0304(5) Uani 1 1 d . . . . .
H64 H 0.831036 -0.107324 0.626551 0.036 Uiso 1 1 calc R U . . .
C65 C 0.8608(3) -0.24021(19) 0.68878(10) 0.0356(6) Uani 1 1 d . . . . .
H65 H 0.836351 -0.285364 0.670533 0.043 Uiso 1 1 calc R U . . .
C66 C 0.8851(2) 0.05062(17) 0.66162(9) 0.0269(5) Uani 1 1 d . . . . .
N8 N 0.8957(2) -0.28272(15) 0.73841(8) 0.0320(4) Uani 1 1 d . . . . .
O15 O 0.8362(2) 0.08359(13) 0.61727(8) 0.0450(5) Uani 1 1 d . . . . .
O16 O 0.92292(17) 0.10640(12) 0.68568(7) 0.0345(4) Uani 1 1 d . . . . .
C67 C 0.8109(3) 0.59269(19) -0.06002(10) 0.0409(6) Uani 1 1 d . . . . .
H67 H 0.804476 0.642657 -0.037997 0.049 Uiso 1 1 calc R U . . .
C68 C 0.8172(3) 0.48575(18) -0.03454(10) 0.0350(6) Uani 1 1 d . . . . .
H68 H 0.817143 0.463109 0.003682 0.042 Uiso 1 1 calc R U . . .
C69 C 0.8235(2) 0.41229(16) -0.06593(9) 0.0237(4) Uani 1 1 d . . . . .
C70 C 0.8221(2) 0.45029(17) -0.12120(9) 0.0244(4) Uani 1 1 d . . . . .
H70 H 0.823833 0.402791 -0.143994 0.029 Uiso 1 1 calc R U . . .
C71 C 0.8182(2) 0.55894(17) -0.14301(9) 0.0278(5) Uani 1 1 d . . . . .
H71 H 0.819095 0.583739 -0.181179 0.033 Uiso 1 1 calc R U . . .
C72 C 0.8345(2) 0.29354(16) -0.04050(9) 0.0243(4) Uani 1 1 d . . . . .
N9 N 0.8134(2) 0.63037(15) -0.11338(8) 0.0343(5) Uani 1 1 d . . . . .
O17 O 0.8634(2) 0.26395(13) 0.00745(7) 0.0395(4) Uani 1 1 d . . . . .
O18 O 0.81645(16) 0.23533(12) -0.06891(7) 0.0308(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.520(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.522(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.512(3) . ?
C4 N1 1.358(3) . ?
C4 O1 1.231(2) . ?
C5 C6 1.389(3) . ?
C5 C10 1.399(3) . ?
C5 N1 1.412(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C7 C8 1.409(3) . ?
C7 C11 1.506(3) . ?
C8 C9 1.401(3) . ?
C8 O3 1.362(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.498(3) . ?
C11 O2 1.225(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C13 C14 1.520(3) . ?
C13 C14A 1.542(16) . ?
C13 O3 1.407(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.504(3) . ?
C14 O4 1.430(3) . ?
C14A H14A 1.0000 . ?
C14A C15 1.524(16) . ?
C14A O4 1.381(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C15 N2 1.485(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.517(3) . ?
C16 C18 1.518(3) . ?
C16 N2 1.500(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 H1 0.82(3) . ?
N2 H2C 0.90(3) . ?
N2 H2D 0.94(3) . ?
O4 H4 0.87(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C20 1.520(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.519(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.516(3) . ?
C22 N3 1.358(3) . ?
C22 O5 1.231(2) . ?
C23 C24 1.390(3) . ?
C23 C28 1.396(3) . ?
C23 N3 1.408(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(3) . ?
C25 C26 1.410(3) . ?
C25 C29 1.505(3) . ?
C26 C27 1.399(3) . ?
C26 O7 1.364(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.497(3) . ?
C29 O6 1.217(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.516(3) . ?
C31 O7 1.414(2) . ?
C32 H32 1.0000 . ?
C32 C33 1.513(3) . ?
C32 O8 1.410(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 N4 1.487(3) . ?
C34 H34 1.0000 . ?
C34 C35 1.518(3) . ?
C34 C36 1.517(3) . ?
C34 N4 1.506(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N3 H3 0.86(3) . ?
N4 H4A 0.91(3) . ?
N4 H4B 0.97(3) . ?
O8 H8 0.93(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C37 C38 1.521(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.516(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.515(3) . ?
C40 N5 1.354(3) . ?
C40 O9 1.232(2) . ?
C41 C42 1.390(3) . ?
C41 C46 1.395(3) . ?
C41 N5 1.412(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.395(3) . ?
C43 C44 1.410(3) . ?
C43 C47 1.505(3) . ?
C44 C45 1.395(3) . ?
C44 O11 1.361(2) . ?
C45 H45 0.9500 . ?
C45 C46 1.387(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.498(3) . ?
C47 O10 1.224(3) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 C50 1.514(3) . ?
C49 O11 1.421(2) . ?
C50 H50 1.0000 . ?
C50 C51 1.513(3) . ?
C50 O12 1.422(2) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 N6 1.483(3) . ?
C52 H52 1.0000 . ?
C52 C53 1.519(3) . ?
C52 C54 1.517(3) . ?
C52 N6 1.502(3) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
N5 H5 0.90(3) . ?
N6 H6A 0.94(3) . ?
N6 H6B 0.91(3) . ?
O12 H12 0.98(4) . ?
C55 H55 0.9500 . ?
C55 C56 1.382(3) . ?
C55 N7 1.340(3) . ?
C56 H56 0.9500 . ?
C56 C57 1.387(3) . ?
C57 C58 1.382(3) . ?
C57 C60 1.513(3) . ?
C58 H58 0.9500 . ?
C58 C59 1.385(3) . ?
C59 H59 0.9500 . ?
C59 N7 1.337(3) . ?
C60 O13 1.244(3) . ?
C60 O14 1.257(3) . ?
C61 H61 0.9500 . ?
C61 C62 1.389(3) . ?
C61 N8 1.339(3) . ?
C62 H62 0.9500 . ?
C62 C63 1.384(3) . ?
C63 C64 1.383(3) . ?
C63 C66 1.510(3) . ?
C64 H64 0.9500 . ?
C64 C65 1.388(3) . ?
C65 H65 0.9500 . ?
C65 N8 1.328(3) . ?
C66 O15 1.264(3) . ?
C66 O16 1.246(3) . ?
C67 H67 0.9500 . ?
C67 C68 1.382(3) . ?
C67 N9 1.332(3) . ?
C68 H68 0.9500 . ?
C68 C69 1.385(3) . ?
C69 C70 1.380(3) . ?
C69 C72 1.514(3) . ?
C70 H70 0.9500 . ?
C70 C71 1.388(3) . ?
C71 H71 0.9500 . ?
C71 N9 1.333(3) . ?
C72 O17 1.257(3) . ?
C72 O18 1.246(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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 C3 111.58(17) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.01(16) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
N1 C4 C3 113.66(16) . . ?
O1 C4 C3 122.73(17) . . ?
O1 C4 N1 123.61(18) . . ?
C6 C5 C10 118.74(18) . . ?
C6 C5 N1 117.28(17) . . ?
C10 C5 N1 123.98(17) . . ?
C5 C6 H6 118.8 . . ?
C5 C6 C7 122.42(18) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C8 118.30(17) . . ?
C6 C7 C11 116.26(17) . . ?
C8 C7 C11 125.44(18) . . ?
C9 C8 C7 119.50(18) . . ?
O3 C8 C7 117.72(17) . . ?
O3 C8 C9 122.77(17) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.05(18) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 119.97(18) . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C7 121.99(18) . . ?
O2 C11 C7 118.58(18) . . ?
O2 C11 C12 119.43(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H13A C13 H13B 108.8 . . ?
H13C C13 H13D 106.5 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
C14A C13 H13C 106.4 . . ?
C14A C13 H13D 106.4 . . ?
O3 C13 H13A 110.7 . . ?
O3 C13 H13B 110.7 . . ?
O3 C13 H13C 106.4 . . ?
O3 C13 H13D 106.4 . . ?
O3 C13 C14 105.01(17) . . ?
O3 C13 C14A 123.7(6) . . ?
C13 C14 H14 108.5 . . ?
C15 C14 C13 111.06(17) . . ?
C15 C14 H14 108.5 . . ?
O4 C14 C13 109.08(18) . . ?
O4 C14 H14 108.5 . . ?
O4 C14 C15 111.02(17) . . ?
C13 C14A H14A 108.3 . . ?
C15 C14A C13 108.8(10) . . ?
C15 C14A H14A 108.3 . . ?
O4 C14A C13 110.5(11) . . ?
O4 C14A H14A 108.3 . . ?
O4 C14A C15 112.6(12) . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C14A C15 H15C 108.3 . . ?
C14A C15 H15D 108.3 . . ?
H15A C15 H15B 108.2 . . ?
H15C C15 H15D 107.4 . . ?
N2 C15 C14 109.48(17) . . ?
N2 C15 C14A 116.0(6) . . ?
N2 C15 H15A 109.8 . . ?
N2 C15 H15B 109.8 . . ?
N2 C15 H15C 108.3 . . ?
N2 C15 H15D 108.3 . . ?
C17 C16 H16 108.5 . . ?
C17 C16 C18 112.99(19) . . ?
C18 C16 H16 108.5 . . ?
N2 C16 H16 108.5 . . ?
N2 C16 C17 107.39(17) . . ?
N2 C16 C18 110.87(18) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 N1 C5 128.70(17) . . ?
C4 N1 H1 118(2) . . ?
C5 N1 H1 113(2) . . ?
C15 N2 C16 114.44(16) . . ?
C15 N2 H2C 112.1(18) . . ?
C15 N2 H2D 108.4(17) . . ?
C16 N2 H2C 110.0(18) . . ?
C16 N2 H2D 107.5(17) . . ?
H2C N2 H2D 104(2) . . ?
C8 O3 C13 119.84(16) . . ?
C14 O4 H4 104(2) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 C19 111.56(18) . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 C20 114.11(17) . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
N3 C22 C21 113.66(17) . . ?
O5 C22 C21 122.49(18) . . ?
O5 C22 N3 123.85(19) . . ?
C24 C23 C28 118.62(19) . . ?
C24 C23 N3 117.15(18) . . ?
C28 C23 N3 124.22(18) . . ?
C23 C24 H24 118.8 . . ?
C23 C24 C25 122.37(19) . . ?
C25 C24 H24 118.8 . . ?
C24 C25 C26 118.52(18) . . ?
C24 C25 C29 115.91(18) . . ?
C26 C25 C29 125.57(19) . . ?
C27 C26 C25 119.31(18) . . ?
O7 C26 C25 117.63(17) . . ?
O7 C26 C27 123.05(18) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 121.01(18) . . ?
C28 C27 H27 119.5 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.16(18) . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C25 121.58(18) . . ?
O6 C29 C25 118.93(19) . . ?
O6 C29 C30 119.48(19) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H31A C31 H31B 108.8 . . ?
C32 C31 H31A 110.6 . . ?
C32 C31 H31B 110.6 . . ?
O7 C31 H31A 110.6 . . ?
O7 C31 H31B 110.6 . . ?
O7 C31 C32 105.51(17) . . ?
C31 C32 H32 107.9 . . ?
C33 C32 C31 112.32(17) . . ?
C33 C32 H32 107.9 . . ?
O8 C32 C31 110.04(18) . . ?
O8 C32 H32 107.9 . . ?
O8 C32 C33 110.62(17) . . ?
C32 C33 H33A 109.8 . . ?
C32 C33 H33B 109.8 . . ?
H33A C33 H33B 108.3 . . ?
N4 C33 C32 109.24(17) . . ?
N4 C33 H33A 109.8 . . ?
N4 C33 H33B 109.8 . . ?
C35 C34 H34 108.8 . . ?
C36 C34 H34 108.8 . . ?
C36 C34 C35 112.39(18) . . ?
N4 C34 H34 108.8 . . ?
N4 C34 C35 110.62(17) . . ?
N4 C34 C36 107.46(17) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C22 N3 C23 128.72(17) . . ?
C22 N3 H3 119.3(18) . . ?
C23 N3 H3 111.9(18) . . ?
C33 N4 C34 115.45(16) . . ?
C33 N4 H4A 107.3(17) . . ?
C33 N4 H4B 109.6(16) . . ?
C34 N4 H4A 108.0(17) . . ?
C34 N4 H4B 109.0(16) . . ?
H4A N4 H4B 107(2) . . ?
C26 O7 C31 120.06(16) . . ?
C32 O8 H8 107(2) . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
C37 C38 H38A 109.2 . . ?
C37 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?
C39 C38 C37 112.25(19) . . ?
C39 C38 H38A 109.2 . . ?
C39 C38 H38B 109.2 . . ?
C38 C39 H39A 108.9 . . ?
C38 C39 H39B 108.9 . . ?
H39A C39 H39B 107.7 . . ?
C40 C39 C38 113.55(17) . . ?
C40 C39 H39A 108.9 . . ?
C40 C39 H39B 108.9 . . ?
N5 C40 C39 113.45(17) . . ?
O9 C40 C39 122.20(18) . . ?
O9 C40 N5 124.34(19) . . ?
C42 C41 C46 118.93(19) . . ?
C42 C41 N5 117.03(18) . . ?
C46 C41 N5 124.04(18) . . ?
C41 C42 H42 118.9 . . ?
C41 C42 C43 122.15(18) . . ?
C43 C42 H42 118.9 . . ?
C42 C43 C44 118.23(18) . . ?
C42 C43 C47 115.97(18) . . ?
C44 C43 C47 125.71(19) . . ?
C45 C44 C43 119.73(19) . . ?
O11 C44 C43 117.38(17) . . ?
O11 C44 C45 122.85(18) . . ?
C44 C45 H45 119.5 . . ?
C46 C45 C44 120.93(18) . . ?
C46 C45 H45 119.5 . . ?
C41 C46 H46 120.0 . . ?
C45 C46 C41 120.02(18) . . ?
C45 C46 H46 120.0 . . ?
C48 C47 C43 121.83(18) . . ?
O10 C47 C43 118.74(19) . . ?
O10 C47 C48 119.41(19) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
H49A C49 H49B 108.8 . . ?
C50 C49 H49A 110.7 . . ?
C50 C49 H49B 110.7 . . ?
O11 C49 H49A 110.7 . . ?
O11 C49 H49B 110.7 . . ?
O11 C49 C50 105.20(16) . . ?
C49 C50 H50 108.9 . . ?
C51 C50 C49 110.86(17) . . ?
C51 C50 H50 108.9 . . ?
O12 C50 C49 108.60(17) . . ?
O12 C50 H50 108.9 . . ?
O12 C50 C51 110.58(17) . . ?
C50 C51 H51A 109.7 . . ?
C50 C51 H51B 109.7 . . ?
H51A C51 H51B 108.2 . . ?
N6 C51 C50 109.95(17) . . ?
N6 C51 H51A 109.7 . . ?
N6 C51 H51B 109.7 . . ?
C53 C52 H52 108.9 . . ?
C54 C52 H52 108.9 . . ?
C54 C52 C53 112.85(19) . . ?
N6 C52 H52 108.9 . . ?
N6 C52 C53 107.01(16) . . ?
N6 C52 C54 110.32(17) . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C40 N5 C41 128.44(17) . . ?
C40 N5 H5 115.2(19) . . ?
C41 N5 H5 115.8(19) . . ?
C51 N6 C52 114.97(16) . . ?
C51 N6 H6A 107.9(16) . . ?
C51 N6 H6B 112.3(17) . . ?
C52 N6 H6A 107.2(16) . . ?
C52 N6 H6B 108.7(17) . . ?
H6A N6 H6B 105(2) . . ?
C44 O11 C49 119.28(16) . . ?
C50 O12 H12 105(2) . . ?
C56 C55 H55 118.0 . . ?
N7 C55 H55 118.0 . . ?
N7 C55 C56 124.0(2) . . ?
C55 C56 H56 120.5 . . ?
C55 C56 C57 118.9(2) . . ?
C57 C56 H56 120.5 . . ?
C56 C57 C60 121.21(19) . . ?
C58 C57 C56 117.70(19) . . ?
C58 C57 C60 121.05(19) . . ?
C57 C58 H58 120.3 . . ?
C57 C58 C59 119.4(2) . . ?
C59 C58 H58 120.3 . . ?
C58 C59 H59 118.2 . . ?
N7 C59 C58 123.5(2) . . ?
N7 C59 H59 118.2 . . ?
O13 C60 C57 117.41(19) . . ?
O13 C60 O14 126.9(2) . . ?
O14 C60 C57 115.63(19) . . ?
C59 N7 C55 116.37(19) . . ?
C62 C61 H61 118.2 . . ?
N8 C61 H61 118.2 . . ?
N8 C61 C62 123.5(2) . . ?
C61 C62 H62 120.6 . . ?
C63 C62 C61 118.9(2) . . ?
C63 C62 H62 120.6 . . ?
C62 C63 C66 121.1(2) . . ?
C64 C63 C62 118.1(2) . . ?
C64 C63 C66 120.7(2) . . ?
C63 C64 H64 120.6 . . ?
C63 C64 C65 118.7(2) . . ?
C65 C64 H64 120.6 . . ?
C64 C65 H65 118.0 . . ?
N8 C65 C64 124.1(2) . . ?
N8 C65 H65 118.0 . . ?
O15 C66 C63 115.5(2) . . ?
O16 C66 C63 118.2(2) . . ?
O16 C66 O15 126.3(2) . . ?
C65 N8 C61 116.7(2) . . ?
C68 C67 H67 117.8 . . ?
N9 C67 H67 117.8 . . ?
N9 C67 C68 124.4(2) . . ?
C67 C68 H68 120.7 . . ?
C67 C68 C69 118.6(2) . . ?
C69 C68 H68 120.7 . . ?
C68 C69 C72 121.0(2) . . ?
C70 C69 C68 117.98(19) . . ?
C70 C69 C72 121.03(19) . . ?
C69 C70 H70 120.5 . . ?
C69 C70 C71 119.0(2) . . ?
C71 C70 H70 120.5 . . ?
C70 C71 H71 118.2 . . ?
N9 C71 C70 123.6(2) . . ?
N9 C71 H71 118.2 . . ?
O17 C72 C69 115.52(19) . . ?
O18 C72 C69 117.61(19) . . ?
O18 C72 O17 126.86(19) . . ?
C67 N9 C71 116.35(19) . . ?

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
C1 C2 C3 C4 175.82(18) . . . . ?
C2 C3 C4 N1 177.74(18) . . . . ?
C2 C3 C4 O1 -2.2(3) . . . . ?
C3 C4 N1 C5 -174.04(19) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C11 -179.69(19) . . . . ?
C6 C5 C10 C9 -1.3(3) . . . . ?
C6 C5 N1 C4 178.2(2) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 O3 177.58(18) . . . . ?
C6 C7 C11 C12 175.5(2) . . . . ?
C6 C7 C11 O2 -4.6(3) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C7 C8 O3 C13 177.80(19) . . . . ?
C8 C7 C11 C12 -4.4(3) . . . . ?
C8 C7 C11 O2 175.6(2) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C9 C8 O3 C13 -3.5(3) . . . . ?
C10 C5 C6 C7 1.1(3) . . . . ?
C10 C5 N1 C4 -1.2(3) . . . . ?
C11 C7 C8 C9 178.71(19) . . . . ?
C11 C7 C8 O3 -2.6(3) . . . . ?
C13 C14 C15 N2 -171.94(18) . . . . ?
C13 C14A C15 N2 148.8(7) . . . . ?
C14 C13 O3 C8 -179.03(18) . . . . ?
C14 C15 N2 C16 -156.07(18) . . . . ?
C14A C13 O3 C8 -145.5(9) . . . . ?
C14A C15 N2 C16 165.4(9) . . . . ?
C17 C16 N2 C15 176.23(18) . . . . ?
C18 C16 N2 C15 -59.9(2) . . . . ?
N1 C5 C6 C7 -178.29(18) . . . . ?
N1 C5 C10 C9 177.98(19) . . . . ?
O1 C4 N1 C5 5.9(3) . . . . ?
O3 C8 C9 C10 -177.78(19) . . . . ?
O3 C13 C14 C15 -168.11(19) . . . . ?
O3 C13 C14 O4 69.2(2) . . . . ?
O3 C13 C14A C15 -127.5(8) . . . . ?
O3 C13 C14A O4 -3.4(17) . . . . ?
O4 C14 C15 N2 -50.4(2) . . . . ?
O4 C14A C15 N2 25.9(16) . . . . ?
C19 C20 C21 C22 -179.36(19) . . . . ?
C20 C21 C22 N3 -172.36(19) . . . . ?
C20 C21 C22 O5 7.7(3) . . . . ?
C21 C22 N3 C23 172.12(19) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C23 C24 C25 C29 178.92(19) . . . . ?
C24 C23 C28 C27 1.0(3) . . . . ?
C24 C23 N3 C22 -174.9(2) . . . . ?
C24 C25 C26 C27 1.3(3) . . . . ?
C24 C25 C26 O7 -177.53(19) . . . . ?
C24 C25 C29 C30 -179.8(2) . . . . ?
C24 C25 C29 O6 -0.6(3) . . . . ?
C25 C26 C27 C28 -1.0(3) . . . . ?
C25 C26 O7 C31 -176.48(19) . . . . ?
C26 C25 C29 C30 -0.4(4) . . . . ?
C26 C25 C29 O6 178.7(2) . . . . ?
C26 C27 C28 C23 -0.2(3) . . . . ?
C27 C26 O7 C31 4.7(3) . . . . ?
C28 C23 C24 C25 -0.7(3) . . . . ?
C28 C23 N3 C22 3.6(3) . . . . ?
C29 C25 C26 C27 -178.0(2) . . . . ?
C29 C25 C26 O7 3.1(3) . . . . ?
C31 C32 C33 N4 171.64(18) . . . . ?
C32 C31 O7 C26 178.42(18) . . . . ?
C32 C33 N4 C34 154.03(18) . . . . ?
C35 C34 N4 C33 57.0(2) . . . . ?
C36 C34 N4 C33 -179.99(18) . . . . ?
N3 C23 C24 C25 177.98(19) . . . . ?
N3 C23 C28 C27 -177.54(19) . . . . ?
O5 C22 N3 C23 -8.0(4) . . . . ?
O7 C26 C27 C28 177.8(2) . . . . ?
O7 C31 C32 C33 171.53(18) . . . . ?
O7 C31 C32 O8 -64.8(2) . . . . ?
O8 C32 C33 N4 48.2(2) . . . . ?
C37 C38 C39 C40 175.58(19) . . . . ?
C38 C39 C40 N5 166.81(19) . . . . ?
C38 C39 C40 O9 -13.8(3) . . . . ?
C39 C40 N5 C41 178.76(19) . . . . ?
C41 C42 C43 C44 0.6(3) . . . . ?
C41 C42 C43 C47 -176.12(19) . . . . ?
C42 C41 C46 C45 0.1(3) . . . . ?
C42 C41 N5 C40 -169.0(2) . . . . ?
C42 C43 C44 C45 0.5(3) . . . . ?
C42 C43 C44 O11 178.36(18) . . . . ?
C42 C43 C47 C48 167.0(2) . . . . ?
C42 C43 C47 O10 -11.2(3) . . . . ?
C43 C44 C45 C46 -1.4(3) . . . . ?
C43 C44 O11 C49 168.75(18) . . . . ?
C44 C43 C47 C48 -9.4(3) . . . . ?
C44 C43 C47 O10 172.3(2) . . . . ?
C44 C45 C46 C41 1.0(3) . . . . ?
C45 C44 O11 C49 -13.5(3) . . . . ?
C46 C41 C42 C43 -0.9(3) . . . . ?
C46 C41 N5 C40 11.2(3) . . . . ?
C47 C43 C44 C45 176.9(2) . . . . ?
C47 C43 C44 O11 -5.3(3) . . . . ?
C49 C50 C51 N6 -166.48(17) . . . . ?
C50 C49 O11 C44 -163.59(17) . . . . ?
C50 C51 N6 C52 -158.23(17) . . . . ?
C53 C52 N6 C51 -179.67(18) . . . . ?
C54 C52 N6 C51 -56.6(2) . . . . ?
N5 C41 C42 C43 179.26(19) . . . . ?
N5 C41 C46 C45 179.89(19) . . . . ?
O9 C40 N5 C41 -0.6(3) . . . . ?
O11 C44 C45 C46 -179.06(19) . . . . ?
O11 C49 C50 C51 -169.08(17) . . . . ?
O11 C49 C50 O12 69.2(2) . . . . ?
O12 C50 C51 N6 -46.0(2) . . . . ?
C55 C56 C57 C58 -0.9(4) . . . . ?
C55 C56 C57 C60 176.8(2) . . . . ?
C56 C55 N7 C59 0.2(4) . . . . ?
C56 C57 C58 C59 1.4(3) . . . . ?
C56 C57 C60 O13 173.6(2) . . . . ?
C56 C57 C60 O14 -7.9(3) . . . . ?
C57 C58 C59 N7 -1.1(4) . . . . ?
C58 C57 C60 O13 -8.8(3) . . . . ?
C58 C57 C60 O14 169.7(2) . . . . ?
C58 C59 N7 C55 0.3(4) . . . . ?
C60 C57 C58 C59 -176.3(2) . . . . ?
N7 C55 C56 C57 0.1(4) . . . . ?
C61 C62 C63 C64 -1.0(3) . . . . ?
C61 C62 C63 C66 175.4(2) . . . . ?
C62 C61 N8 C65 0.0(4) . . . . ?
C62 C63 C64 C65 0.2(3) . . . . ?
C62 C63 C66 O15 -172.5(2) . . . . ?
C62 C63 C66 O16 6.0(3) . . . . ?
C63 C64 C65 N8 0.7(4) . . . . ?
C64 C63 C66 O15 3.8(3) . . . . ?
C64 C63 C66 O16 -177.8(2) . . . . ?
C64 C65 N8 C61 -0.9(4) . . . . ?
C66 C63 C64 C65 -176.1(2) . . . . ?
N8 C61 C62 C63 0.9(4) . . . . ?
C67 C68 C69 C70 -0.5(4) . . . . ?
C67 C68 C69 C72 178.1(2) . . . . ?
C68 C67 N9 C71 2.2(4) . . . . ?
C68 C69 C70 C71 1.9(3) . . . . ?
C68 C69 C72 O17 -14.4(3) . . . . ?
C68 C69 C72 O18 166.8(2) . . . . ?
C69 C70 C71 N9 -1.3(4) . . . . ?
C70 C69 C72 O17 164.2(2) . . . . ?
C70 C69 C72 O18 -14.6(3) . . . . ?
C70 C71 N9 C67 -0.7(4) . . . . ?
C72 C69 C70 C71 -176.8(2) . . . . ?
N9 C67 C68 C69 -1.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.748
