# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_21dm001
_database_code_depnum_ccdc_archive 'CCDC 2109211'
loop_
_audit_author_name
_audit_author_address
'Bryson Hawkins'
;Sydney School of Pharmacy, Faculty of Medicine and Health, The University of Sydney 
Australia
;
_audit_update_record             
;
2021-09-11 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_audit_creation_date             2021-07-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
bryson.hawkins@sydney.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 N3 O3'
_chemical_formula_sum            'C18 H23 N3 O3'
_chemical_formula_weight         329.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H23 N3 O3 '
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      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                   13.6962(3)
_cell_length_b                   13.6338(2)
_cell_length_c                   9.2710(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.983(3)
_cell_angle_gamma                90
_cell_volume                     1672.32(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12907
_cell_measurement_temperature    150.00(18)
_cell_measurement_theta_max      30.6570
_cell_measurement_theta_min      2.8100
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 4 -12 0.2514
4 12 -10 0.2348
12 14 -4 0.1655
-12 -14 4 0.1491
11 7 7 0.1738
-1 5 12 0.2352
14 -13 -4 0.1541
-11 -8 11 0.2262
17 -9 -2 0.1324
-11 -13 8 0.1931
18 -7 -1 0.1275
-14 12 -1 0.1311
-11 -15 0 0.1082
13 13 0 0.1175
-8 -15 -4 0.1264
11 13 4 0.1350
16 -7 3 0.1410
6 13 8 0.1705
-10 -9 -7 0.1619

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Slow Evaporation from DCM'
_exptl_crystal_size_max          0.563
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.243
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
-1.4892 4.4785 -11.9857 0.8586 0.2544 -0.4450
4.1559 12.4288 -9.9720 0.5542 0.7226 -0.4132
12.3753 14.4362 -4.1799 0.0256 0.9996 -0.0091
-12.3753 -14.4362 4.1799 -0.0256 -0.9996 0.0091
11.4181 6.8371 7.1485 -0.7219 0.5528 0.4163
-0.7254 4.5695 12.3897 -0.9969 0.0254 0.0747
14.1121 -12.8255 -4.2957 0.3958 -0.0111 0.9183
-11.1090 -8.4531 10.6541 -0.6083 -0.7937 0.0055
16.9329 -9.1352 -2.0514 0.1537 0.1988 0.9679
-10.7805 -13.1481 7.8172 -0.3311 -0.9372 0.1098
17.6771 -6.7763 -0.6413 0.0088 0.2997 0.9540
-14.4839 11.7374 -0.6776 -0.0009 0.0091 -1.0000
-11.4667 -15.2083 0.1398 0.2846 -0.9586 -0.0091
13.3767 13.4221 -0.0491 -0.2813 0.9481 0.1485
-8.4176 -15.2811 -3.8661 0.5664 -0.8230 0.0427
10.5501 13.4837 3.9430 -0.5636 0.8192 0.1062
15.6907 -7.3152 2.8321 -0.2323 0.1793 0.9560
6.0141 12.7277 7.5638 -0.7937 0.6083 0.0092
-9.7637 -9.0416 -7.4322 0.7613 -0.5838 -0.2822

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26702
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.721
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4948
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  61.00   1.00   17.66    --   15.22  60.00 -46.80   74
  2  ω    -41.00  44.00   1.00   17.66    --   15.22 -60.00-132.48   85
  3  ω     14.00  88.00   1.00   17.66    --   15.22  59.00-141.87   74
  4  ω     -7.00  69.00   1.00   17.66    --   15.22  57.00 150.00   76
  5  ω    -56.00  42.00   1.00   17.66    --   15.22 -57.00  90.00   98
  6  ω      7.00  84.00   1.00   17.66    --   15.22  57.00  30.00   77
  7  ω    -23.00  43.00   1.00   17.66    --   15.22 -57.00 150.00   66
  8  ω    -53.00  44.00   1.00   17.66    --   15.22 -60.00 -19.21   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0075212000
_diffrn_orient_matrix_UB_12      -0.0137376000
_diffrn_orient_matrix_UB_13      -0.0758344000
_diffrn_orient_matrix_UB_21      0.0315734000
_diffrn_orient_matrix_UB_22      0.0391298000
_diffrn_orient_matrix_UB_23      -0.0105306000
_diffrn_orient_matrix_UB_31      0.0426658000
_diffrn_orient_matrix_UB_32      -0.0313841000
_diffrn_orient_matrix_UB_33      0.0201024000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3427
_reflns_number_total             4155
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0560
_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)+(0.0650P)²+1.0921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1521
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq,
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
2.a Ternary CH refined with riding coordinates:
 C13(H13), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B),
 C16(H16A,H16B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), N2(H2A), N3(H3A)
;
_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 0.44721(12) 0.40703(12) 0.3587(2) 0.0345(4) Uani 1 1 d . . . . .
C2 C 0.48397(13) 0.47609(13) 0.2775(2) 0.0397(4) Uani 1 1 d . . . . .
H2 H 0.544898 0.464344 0.249349 0.048 Uiso 1 1 calc R U . . .
C3 C 0.43152(13) 0.56215(13) 0.2377(2) 0.0357(4) Uani 1 1 d . . . . .
H3 H 0.456329 0.610080 0.181760 0.043 Uiso 1 1 calc R U . . .
C4 C 0.34158(11) 0.57951(11) 0.27925(16) 0.0255(3) Uani 1 1 d . . . . .
C5 C 0.30409(12) 0.50727(12) 0.35753(18) 0.0300(3) Uani 1 1 d . . . . .
H5 H 0.241940 0.517302 0.382961 0.036 Uiso 1 1 calc R U . . .
C6 C 0.35754(13) 0.42115(12) 0.39796(19) 0.0341(4) Uani 1 1 d . . . . .
H6 H 0.332824 0.372141 0.452260 0.041 Uiso 1 1 calc R U . . .
C7 C 0.21705(11) 0.71081(10) 0.28817(16) 0.0233(3) Uani 1 1 d . . . . .
C8 C 0.09956(12) 0.84968(11) 0.24856(19) 0.0298(3) Uani 1 1 d . . . . .
H8A H 0.086893 0.823412 0.341619 0.036 Uiso 1 1 calc R U . . .
H8B H 0.035173 0.846368 0.169787 0.036 Uiso 1 1 calc R U . . .
C9 C 0.13141(11) 0.95696(10) 0.27369(16) 0.0242(3) Uani 1 1 d . . . . .
C10 C 0.14647(12) 1.00375(11) 0.13159(17) 0.0272(3) Uani 1 1 d . U . . .
H10A H 0.083985 0.996177 0.050051 0.033 Uiso 1 1 calc R U . . .
H10B H 0.201874 0.969657 0.101389 0.033 Uiso 1 1 calc R U . . .
C11 C 0.22813(18) 0.96751(13) 0.3968(2) 0.0513(6) Uani 1 1 d . U . . .
H11A H 0.283674 0.932264 0.368675 0.062 Uiso 1 1 calc R U . . .
H11B H 0.219079 0.938152 0.490134 0.062 Uiso 1 1 calc R U . . .
C12 C 0.04493(17) 1.01169(14) 0.3171(3) 0.0479(5) Uani 1 1 d . U . . .
H12A H -0.017780 1.006063 0.235449 0.057 Uiso 1 1 calc R U . . .
H12B H 0.032450 0.981823 0.407979 0.057 Uiso 1 1 calc R U . . .
C13 C 0.17211(13) 1.11262(12) 0.1554(2) 0.0340(4) Uani 1 1 d . U . . .
H13 H 0.180971 1.141978 0.060754 0.041 Uiso 1 1 calc R U . . .
C14 C 0.26957(16) 1.12237(14) 0.2776(3) 0.0643(7) Uani 1 1 d . U . . .
H14A H 0.287789 1.192485 0.294296 0.077 Uiso 1 1 calc R U . . .
H14B H 0.325062 1.088548 0.247255 0.077 Uiso 1 1 calc R U . . .
C15 C 0.2555(2) 1.07669(16) 0.4223(3) 0.0768(9) Uani 1 1 d . U . . .
H15 H 0.319360 1.083490 0.503483 0.092 Uiso 1 1 calc R U . . .
C16 C 0.08835(15) 1.16632(12) 0.2038(2) 0.0402(4) Uani 1 1 d . U . . .
H16A H 0.024749 1.162483 0.123502 0.048 Uiso 1 1 calc R U . . .
H16B H 0.106577 1.236351 0.221719 0.048 Uiso 1 1 calc R U . . .
C17 C 0.0729(2) 1.12025(14) 0.3462(3) 0.0567(6) Uani 1 1 d . U . . .
H17 H 0.017038 1.155118 0.376283 0.068 Uiso 1 1 calc R U . . .
C18 C 0.1686(3) 1.12917(17) 0.4684(3) 0.0863(11) Uani 1 1 d . U . . .
H18A H 0.159019 1.099481 0.561251 0.104 Uiso 1 1 calc R U . . .
H18B H 0.185744 1.199280 0.488210 0.104 Uiso 1 1 calc R U . . .
N1 N 0.50524(12) 0.31800(12) 0.4068(2) 0.0462(4) Uani 1 1 d . . . . .
N2 N 0.29138(10) 0.66711(9) 0.23274(15) 0.0275(3) Uani 1 1 d . . . . .
H2A H 0.308664 0.698358 0.160037 0.033 Uiso 1 1 calc R U . . .
N3 N 0.17324(10) 0.78775(9) 0.20545(14) 0.0270(3) Uani 1 1 d . . . . .
H3A H 0.189970 0.800958 0.122050 0.032 Uiso 1 1 calc R U . . .
O1 O 0.47223(13) 0.25623(11) 0.4777(2) 0.0632(5) Uani 1 1 d . . . . .
O2 O 0.58657(11) 0.30959(12) 0.3751(2) 0.0669(5) Uani 1 1 d . . . . .
O3 O 0.19475(9) 0.68156(8) 0.40087(12) 0.0316(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 1.379(3) . ?
C1 C6 1.382(2) . ?
C1 N1 1.456(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.403(2) . ?
C4 C5 1.398(2) . ?
C4 N2 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C7 N2 1.3877(19) . ?
C7 N3 1.3455(19) . ?
C7 O3 1.2284(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.527(2) . ?
C8 N3 1.4489(19) . ?
C9 C10 1.525(2) . ?
C9 C11 1.515(2) . ?
C9 C12 1.539(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C13 1.528(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C15 1.538(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C17 1.535(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.517(3) . ?
C13 C16 1.523(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.536(4) . ?
C15 H15 1.0000 . ?
C15 C18 1.540(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.526(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.500(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N1 O1 1.224(3) . ?
N1 O2 1.229(2) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?

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 121.57(16) . . ?
C2 C1 N1 119.27(16) . . ?
C6 C1 N1 119.15(17) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.32(15) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.34(16) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.37(15) . . ?
N2 C4 C3 117.31(14) . . ?
N2 C4 C5 123.23(13) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.94(15) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.41(16) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N3 C7 N2 112.67(12) . . ?
O3 C7 N2 122.89(14) . . ?
O3 C7 N3 124.44(14) . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
N3 C8 H8A 108.7 . . ?
N3 C8 H8B 108.7 . . ?
N3 C8 C9 114.10(12) . . ?
C8 C9 C12 107.20(13) . . ?
C10 C9 C8 111.48(12) . . ?
C10 C9 C12 107.94(12) . . ?
C11 C9 C8 111.44(13) . . ?
C11 C9 C10 108.88(15) . . ?
C11 C9 C12 109.83(16) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C13 111.03(13) . . ?
H10A C10 H10B 108.0 . . ?
C13 C10 H10A 109.4 . . ?
C13 C10 H10B 109.4 . . ?
C9 C11 H11A 109.7 . . ?
C9 C11 H11B 109.7 . . ?
C9 C11 C15 109.78(15) . . ?
H11A C11 H11B 108.2 . . ?
C15 C11 H11A 109.7 . . ?
C15 C11 H11B 109.7 . . ?
C9 C12 H12A 109.7 . . ?
C9 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C17 C12 C9 109.85(16) . . ?
C17 C12 H12A 109.7 . . ?
C17 C12 H12B 109.7 . . ?
C10 C13 H13 109.7 . . ?
C14 C13 C10 108.54(14) . . ?
C14 C13 H13 109.7 . . ?
C14 C13 C16 108.81(17) . . ?
C16 C13 C10 110.31(14) . . ?
C16 C13 H13 109.7 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C13 C14 C15 109.38(18) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C11 C15 H15 109.7 . . ?
C11 C15 C18 108.5(3) . . ?
C14 C15 C11 109.8(2) . . ?
C14 C15 H15 109.7 . . ?
C14 C15 C18 109.55(19) . . ?
C18 C15 H15 109.7 . . ?
C13 C16 H16A 109.7 . . ?
C13 C16 H16B 109.7 . . ?
C13 C16 C17 109.90(14) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C12 C17 H17 109.5 . . ?
C16 C17 C12 109.20(17) . . ?
C16 C17 H17 109.5 . . ?
C18 C17 C12 109.92(18) . . ?
C18 C17 C16 109.3(2) . . ?
C18 C17 H17 109.5 . . ?
C15 C18 H18A 109.7 . . ?
C15 C18 H18B 109.7 . . ?
C17 C18 C15 109.84(17) . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O1 N1 C1 119.33(17) . . ?
O1 N1 O2 123.21(17) . . ?
O2 N1 C1 117.45(19) . . ?
C4 N2 H2A 116.4 . . ?
C7 N2 C4 127.26(13) . . ?
C7 N2 H2A 116.4 . . ?
C7 N3 C8 122.47(13) . . ?
C7 N3 H3A 118.8 . . ?
C8 N3 H3A 118.8 . . ?

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 0.0(3) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C2 C1 N1 O1 -179.33(17) . . . . ?
C2 C1 N1 O2 1.6(2) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 N2 -178.73(15) . . . . ?
C3 C4 C5 C6 2.3(2) . . . . ?
C3 C4 N2 C7 -163.14(15) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C5 C4 N2 C7 20.2(2) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
C6 C1 N1 O1 1.9(2) . . . . ?
C6 C1 N1 O2 -177.16(17) . . . . ?
C8 C9 C10 C13 176.59(13) . . . . ?
C8 C9 C11 C15 -178.0(2) . . . . ?
C8 C9 C12 C17 179.20(16) . . . . ?
C9 C8 N3 C7 118.96(16) . . . . ?
C9 C10 C13 C14 60.7(2) . . . . ?
C9 C10 C13 C16 -58.44(19) . . . . ?
C9 C11 C15 C14 -59.4(3) . . . . ?
C9 C11 C15 C18 60.3(3) . . . . ?
C9 C12 C17 C16 61.3(2) . . . . ?
C9 C12 C17 C18 -58.6(2) . . . . ?
C10 C9 C11 C15 58.6(2) . . . . ?
C10 C9 C12 C17 -60.6(2) . . . . ?
C10 C13 C14 C15 -59.8(2) . . . . ?
C10 C13 C16 C17 57.7(2) . . . . ?
C11 C9 C10 C13 -60.06(17) . . . . ?
C11 C9 C12 C17 58.0(2) . . . . ?
C11 C15 C18 C17 -61.0(3) . . . . ?
C12 C9 C10 C13 59.12(18) . . . . ?
C12 C9 C11 C15 -59.4(2) . . . . ?
C12 C17 C18 C15 60.4(3) . . . . ?
C13 C14 C15 C11 60.0(2) . . . . ?
C13 C14 C15 C18 -59.1(2) . . . . ?
C13 C16 C17 C12 -59.2(2) . . . . ?
C13 C16 C17 C18 61.1(2) . . . . ?
C14 C13 C16 C17 -61.2(2) . . . . ?
C14 C15 C18 C17 58.9(3) . . . . ?
C16 C13 C14 C15 60.2(2) . . . . ?
C16 C17 C18 C15 -59.5(2) . . . . ?
N1 C1 C2 C3 -177.11(16) . . . . ?
N1 C1 C6 C5 177.50(15) . . . . ?
N2 C4 C5 C6 178.91(15) . . . . ?
N2 C7 N3 C8 -174.78(13) . . . . ?
N3 C7 N2 C4 -170.97(14) . . . . ?
N3 C8 C9 C10 61.65(17) . . . . ?
N3 C8 C9 C11 -60.23(19) . . . . ?
N3 C8 C9 C12 179.57(14) . . . . ?
O3 C7 N2 C4 9.2(2) . . . . ?
O3 C7 N3 C8 5.1(2) . . . . ?

_olex2_date_sample_submission    2021-07-14
_olex2_exptl_crystal_mounting_method 'Paratone N'
_olex2_submission_original_sample_id 'DM001 DC020'
_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.713
####################################################################### 
# 
# 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_21bh013
_database_code_depnum_ccdc_archive 'CCDC 2109213'
loop_
_audit_author_name
_audit_author_address
'Bryson Hawkins'
;Sydney School of Pharmacy, Faculty of Medicine and Health, The University of Sydney 
Australia
;
_audit_update_record             
;
2021-09-11 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_audit_creation_date             2021-09-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 N3 O3, C16 H36 N, Cl'
_chemical_formula_sum            'C34 H59 Cl N4 O3'
_chemical_formula_weight         607.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 N3 O2 Cl1'
_chemical_oxdiff_usercomment     cd029-tbacl
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   8.1181(2)
_cell_length_b                   13.6649(4)
_cell_length_c                   17.6062(6)
_cell_angle_alpha                108.557(3)
_cell_angle_beta                 100.746(2)
_cell_angle_gamma                95.887(2)
_cell_volume                     1791.40(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11919
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      29.2290
_cell_measurement_theta_min      2.7680
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.97867
_exptl_absorpt_correction_T_min  0.97867
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sphere
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -19 6 0.3397
-5 18 -6 0.2984
-5 15 -17 0.2592
0 -16 19 0.3052
-5 11 -19 0.2297
-5 7 -20 0.1982
-1 -7 25 0.2438
-5 2 -19 0.1801
-1 -1 24 0.2228
-5 -3 -17 0.1914
-1 4 21 0.2332
-4 -8 -13 0.2224
-1 10 15 0.2670
-2 18 1 0.3269
-4 -15 -1 0.2851
-2 19 -6 0.3417
-5 -16 12 0.3192
-2 16 -18 0.3443
-1 7 -24 0.3151
-7 0 21 0.2595
11 -2 -1 0.3395
1 -5 -21 0.3021
-7 5 19 0.2514
0 -14 -9 0.3260
-6 14 8 0.2917

_exptl_crystal_size_max          0.91
_exptl_crystal_size_mid          0.74
_exptl_crystal_size_min          0.53
_exptl_crystal_size_rad          0.328
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
-0.1561 -19.0637 6.4780 0.4774 -0.8778 0.0391
-5.2204 17.9531 -5.7136 -0.4280 0.7882 0.4422
-4.7822 14.8517 -16.5472 -0.7777 0.3710 0.5075
-0.4165 -16.2659 19.2790 0.9013 -0.4293 -0.0575
-4.6553 11.2693 -19.4764 -0.8371 0.1102 0.5359
-4.7518 6.8083 -20.2640 -0.8080 -0.1497 0.5699
-0.7579 -7.2028 24.6189 0.9772 0.1816 -0.1100
-4.7324 2.0050 -19.3993 -0.7153 -0.3883 0.5810
-0.7587 -1.4075 23.7457 0.8715 0.4737 -0.1268
-4.5354 -2.9445 -17.0653 -0.5683 -0.5988 0.5643
-0.5566 4.4811 20.5511 0.6810 0.7183 -0.1426
-4.4040 -7.7144 -13.0389 -0.3628 -0.7606 0.5384
-0.6605 10.0227 15.4602 0.4273 0.8970 -0.1135
-1.5782 17.9134 1.2540 -0.1826 0.9816 0.0561
-4.3463 -15.0041 -1.0304 0.1617 -0.8719 0.4622
-1.9034 19.2014 -6.3831 -0.4728 0.8692 0.1446
-5.0198 -16.1841 12.4149 0.6605 -0.6265 0.4139
-2.1426 16.0288 -18.4915 -0.8664 0.4123 0.2818
-1.4352 7.2494 -23.6064 -0.9383 -0.1748 0.2983
-7.1464 -0.2489 21.3306 0.7791 0.4230 0.4627
11.2790 -1.7136 -0.7866 -0.0223 -0.0109 -0.9997
0.9272 -4.5623 -20.6391 -0.6836 -0.7214 0.1104
-7.0793 5.0516 18.5730 0.6120 0.6449 0.4578
-0.3164 -14.3116 -8.6952 -0.1280 -0.9785 0.1620
-6.3749 14.0167 8.0105 0.1168 0.8872 0.4463

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25252
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.509
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4948
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  82.00   1.00   15.00    --   11.41  57.00  90.00   85
  2  ω     -1.00  80.00   1.00   15.00    --   11.41  57.00 -30.00   81
  3  ω    -59.00  40.00   1.00   15.00    --   11.41 -57.00  60.00   99
  4  ω    -56.00  40.00   1.00   15.00    --   11.41 -57.00 -60.00   96
  5  ω    -58.00  40.00   1.00   15.00    --   11.41 -57.00-180.00   98
  6  ω      0.00  79.00   1.00   15.00    --   11.41  57.00-150.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0014266000
_diffrn_orient_matrix_UB_12      -0.0128311000
_diffrn_orient_matrix_UB_13      0.0358950000
_diffrn_orient_matrix_UB_21      0.0088609000
_diffrn_orient_matrix_UB_22      0.0539367000
_diffrn_orient_matrix_UB_23      0.0234300000
_diffrn_orient_matrix_UB_31      -0.0898597000
_diffrn_orient_matrix_UB_32      -0.0041905000
_diffrn_orient_matrix_UB_33      -0.0084610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5820
_reflns_number_total             7304
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         7304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.034
_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)+(0.0499P)²+0.6651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1145
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C1'(H1'A,H1'B), C2'(H2'A,H2'B), C4'(H4'A,H4'B), C6'(H6'A,H6'B), C7'(H7'A,
 H7'B), C8(H8A,H8B), C8'(H8'A,H8'B), C10'(H10A,H10B), C10(H10C,H10D), C11'(H11A,
 H11B), C11(H11C,H11D), C12'(H12A,H12B), C12(H12C,H12D), C14'(H14A,H14B),
 C15'(H15A,H15B), C15(H15C,H15D), C16'(H16A,H16B), C17(H17D,H17E), C18(H18A,
 H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), N2(H2A), N3(H3A)
2.d Idealised Me refined as rotating group:
 C5'(H5'A,H5'B,H5'C), C9'(H9'A,H9'B,H9'C), C13'(H13A,H13B,H13C), C17'(H17A,
 H17B,H17C)
;
_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 0.10930(19) 0.71604(12) 0.54719(9) 0.0284(3) Uani 1 1 d . . . . .
C1' C 0.43407(18) 0.51189(12) 0.25411(9) 0.0256(3) Uani 1 1 d . . . . .
H1'A H 0.404196 0.444800 0.207147 0.031 Uiso 1 1 calc R U . . .
H1'B H 0.334516 0.547953 0.251629 0.031 Uiso 1 1 calc R U . . .
C2' C 0.4638(2) 0.48740(13) 0.33344(10) 0.0315(4) Uani 1 1 d . . . . .
H2'A H 0.483851 0.553259 0.381163 0.038 Uiso 1 1 calc R U . . .
H2'B H 0.566324 0.454286 0.338407 0.038 Uiso 1 1 calc R U . . .
C2 C 0.11968(19) 0.64296(12) 0.47335(10) 0.0294(3) Uani 1 1 d . . . . .
H2 H 0.133651 0.573610 0.469884 0.035 Uiso 1 1 calc R U . . .
C3 C 0.10936(19) 0.67287(12) 0.40532(9) 0.0270(3) Uani 1 1 d . . . . .
H3 H 0.116359 0.623491 0.354462 0.032 Uiso 1 1 calc R U . . .
C4 C 0.08864(18) 0.77524(12) 0.40968(9) 0.0248(3) Uani 1 1 d . . . . .
C4' C 0.3100(2) 0.41372(13) 0.33410(10) 0.0308(4) Uani 1 1 d . . . . .
H4'A H 0.209563 0.449076 0.332618 0.037 Uiso 1 1 calc R U . . .
H4'B H 0.285326 0.350420 0.283962 0.037 Uiso 1 1 calc R U . . .
C5 C 0.0800(2) 0.84741(12) 0.48521(10) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.067734 0.917256 0.489555 0.037 Uiso 1 1 calc R U . . .
C5' C 0.3383(2) 0.38077(15) 0.40976(11) 0.0419(4) Uani 1 1 d . . . . .
H5'A H 0.442866 0.350832 0.413995 0.063 Uiso 1 1 calc R U . . .
H5'B H 0.241442 0.328195 0.404767 0.063 Uiso 1 1 calc R U . . .
H5'C H 0.348832 0.442075 0.459207 0.063 Uiso 1 1 calc R U . . .
C6 C 0.0892(2) 0.81723(13) 0.55321(10) 0.0321(4) Uani 1 1 d . . . . .
H6 H 0.081822 0.865977 0.604258 0.038 Uiso 1 1 calc R U . . .
C6' C 0.64105(19) 0.68179(12) 0.31511(9) 0.0280(3) Uani 1 1 d . . . . .
H6'A H 0.681707 0.665464 0.365579 0.034 Uiso 1 1 calc R U . . .
H6'B H 0.739394 0.721743 0.305718 0.034 Uiso 1 1 calc R U . . .
C7 C 0.0468(2) 0.88992(12) 0.32444(10) 0.0283(3) Uani 1 1 d . . . . .
C7' C 0.5081(2) 0.75167(13) 0.33054(10) 0.0364(4) Uani 1 1 d . . . . .
H7'A H 0.409407 0.713295 0.340924 0.044 Uiso 1 1 calc R U . . .
H7'B H 0.467661 0.770006 0.281015 0.044 Uiso 1 1 calc R U . . .
C8 C 0.0259(2) 0.97115(12) 0.21801(10) 0.0307(3) Uani 1 1 d . . . . .
H8A H 0.002617 1.030177 0.262301 0.037 Uiso 1 1 calc R U . . .
H8B H -0.068915 0.953921 0.168908 0.037 Uiso 1 1 calc R U . . .
C8' C 0.5823(3) 0.85236(15) 0.40480(11) 0.0486(5) Uani 1 1 d . . . . .
H8'A H 0.693698 0.882441 0.399141 0.058 Uiso 1 1 calc R U . . .
H8'B H 0.505489 0.904028 0.404173 0.058 Uiso 1 1 calc R U . . .
C9 C 0.1911(2) 1.00627(12) 0.19704(9) 0.0260(3) Uani 1 1 d . . . . .
C9' C 0.6062(3) 0.83604(19) 0.48593(12) 0.0618(6) Uani 1 1 d . . . . .
H9'A H 0.496459 0.806428 0.492215 0.093 Uiso 1 1 calc R U . . .
H9'B H 0.651148 0.903375 0.530506 0.093 Uiso 1 1 calc R U . . .
H9'C H 0.686502 0.787636 0.488246 0.093 Uiso 1 1 calc R U . . .
C10' C 0.73626(18) 0.52389(12) 0.23761(9) 0.0261(3) Uani 1 1 d . . . . .
H10A H 0.830591 0.572491 0.233469 0.031 Uiso 1 1 calc R U . . .
H10B H 0.772598 0.510808 0.289875 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3433(2) 1.03342(14) 0.27032(10) 0.0368(4) Uani 1 1 d . . . . .
H10C H 0.356276 0.970883 0.286248 0.044 Uiso 1 1 calc R U . . .
H10D H 0.323288 1.089264 0.317917 0.044 Uiso 1 1 calc R U . . .
C11' C 0.7117(2) 0.42116(14) 0.16719(11) 0.0360(4) Uani 1 1 d . . . . .
H11A H 0.672539 0.431887 0.114166 0.043 Uiso 1 1 calc R U . . .
H11B H 0.623594 0.369448 0.172309 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1737(2) 1.10496(13) 0.17428(10) 0.0332(4) Uani 1 1 d . . . . .
H11C H 0.075960 1.088889 0.126650 0.040 Uiso 1 1 calc R U . . .
H11D H 0.151515 1.160762 0.221254 0.040 Uiso 1 1 calc R U . . .
C12' C 0.8789(2) 0.37950(14) 0.16851(10) 0.0348(4) Uani 1 1 d . . . . .
H12A H 0.968337 0.433929 0.167686 0.042 Uiso 1 1 calc R U . . .
H12B H 0.913696 0.365295 0.220403 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2247(2) 0.92080(13) 0.12312(10) 0.0352(4) Uani 1 1 d . . . . .
H12C H 0.236719 0.856632 0.136826 0.042 Uiso 1 1 calc R U . . .
H12D H 0.127028 0.903242 0.075234 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3365(2) 1.14364(14) 0.15261(12) 0.0416(4) Uani 1 1 d . . . . .
H13 H 0.323324 1.207912 0.138103 0.050 Uiso 1 1 calc R U . . .
C13' C 0.8664(3) 0.28018(17) 0.09627(14) 0.0577(6) Uani 1 1 d . . . . .
H13A H 0.778744 0.225755 0.097015 0.087 Uiso 1 1 calc R U . . .
H13B H 0.976304 0.256181 0.100350 0.087 Uiso 1 1 calc R U . . .
H13C H 0.835912 0.294350 0.044722 0.087 Uiso 1 1 calc R U . . .
C14 C 0.5066(2) 1.07077(16) 0.24809(13) 0.0487(5) Uani 1 1 d . . . . .
H14 H 0.605441 1.087275 0.296194 0.058 Uiso 1 1 calc R U . . .
C14' C 0.51734(18) 0.59992(12) 0.16335(9) 0.0250(3) Uani 1 1 d . . . . .
H14A H 0.483233 0.531837 0.117476 0.030 Uiso 1 1 calc R U . . .
H14B H 0.413904 0.631835 0.168038 0.030 Uiso 1 1 calc R U . . .
C15' C 0.6413(2) 0.67010(13) 0.14109(9) 0.0309(4) Uani 1 1 d . . . . .
H15A H 0.747666 0.641060 0.138039 0.037 Uiso 1 1 calc R U . . .
H15B H 0.669822 0.740723 0.183960 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4870(3) 1.16920(15) 0.22588(14) 0.0497(5) Uani 1 1 d . . . . .
H15C H 0.468087 1.225419 0.273559 0.060 Uiso 1 1 calc R U . . .
H15D H 0.592241 1.194394 0.211971 0.060 Uiso 1 1 calc R U . . .
C16' C 0.5618(2) 0.67786(15) 0.05819(10) 0.0406(4) Uani 1 1 d . . . . .
H16A H 0.525638 0.606369 0.016775 0.049 Uiso 1 1 calc R U . . .
H16B H 0.458912 0.710390 0.062831 0.049 Uiso 1 1 calc R U . . .
C16 C 0.3871(3) 0.95881(15) 0.10104(12) 0.0471(5) Uani 1 1 d . . . . .
H16 H 0.407931 0.902542 0.053074 0.056 Uiso 1 1 calc R U . . .
C17' C 0.6822(3) 0.74146(19) 0.02864(13) 0.0608(6) Uani 1 1 d . . . . .
H17A H 0.720511 0.811894 0.069918 0.091 Uiso 1 1 calc R U . . .
H17B H 0.623421 0.746603 -0.023508 0.091 Uiso 1 1 calc R U . . .
H17C H 0.780910 0.707094 0.020348 0.091 Uiso 1 1 calc R U . . .
C17 C 0.3670(3) 1.05724(15) 0.07862(13) 0.0511(5) Uani 1 1 d . . . . .
H17D H 0.269654 1.040843 0.030749 0.061 Uiso 1 1 calc R U . . .
H17E H 0.471120 1.081546 0.063403 0.061 Uiso 1 1 calc R U . . .
C18 C 0.5368(3) 0.98511(17) 0.17436(15) 0.0571(6) Uani 1 1 d . . . . .
H18A H 0.642224 1.009222 0.160016 0.069 Uiso 1 1 calc R U . . .
H18B H 0.551632 0.921613 0.188673 0.069 Uiso 1 1 calc R U . . .
N1 N 0.11567(17) 0.68492(12) 0.61909(9) 0.0350(3) Uani 1 1 d . . . . .
N1' N 0.58200(15) 0.57894(10) 0.24276(7) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.07595(16) 0.79707(10) 0.33745(8) 0.0275(3) Uani 1 1 d . . . . .
H2A H 0.087712 0.746020 0.294399 0.033 Uiso 1 1 calc R U . . .
N3 N 0.02932(18) 0.88086(10) 0.24451(8) 0.0320(3) Uani 1 1 d . . . . .
H3A H 0.019718 0.818361 0.207402 0.038 Uiso 1 1 calc R U . . .
O1 O 0.09361(18) 0.74809(11) 0.68232(8) 0.0466(3) Uani 1 1 d . . . . .
O2 O 0.14138(18) 0.59570(10) 0.61352(8) 0.0498(3) Uani 1 1 d . . . . .
O3 O 0.03640(17) 0.96890(9) 0.37894(7) 0.0413(3) Uani 1 1 d . . . . .
Cl1* Cl 0.09503(5) 0.64039(3) 0.16552(2) 0.03173(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.388(2) . ?
C1 C6 1.382(2) . ?
C1 N1 1.452(2) . ?
C1' H1'A 0.9900 . ?
C1' H1'B 0.9900 . ?
C1' C2' 1.520(2) . ?
C1' N1' 1.5172(19) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C2' C4' 1.526(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(2) . ?
C4 C5 1.400(2) . ?
C4 N2 1.3841(19) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C4' C5' 1.523(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(2) . ?
C5' H5'A 0.9800 . ?
C5' H5'B 0.9800 . ?
C5' H5'C 0.9800 . ?
C6 H6 0.9500 . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C6' C7' 1.518(2) . ?
C6' N1' 1.5239(19) . ?
C7 N2 1.3945(19) . ?
C7 N3 1.352(2) . ?
C7 O3 1.2177(19) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C7' C8' 1.535(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.527(2) . ?
C8 N3 1.4523(19) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C8' C9' 1.495(3) . ?
C9 C10 1.528(2) . ?
C9 C11 1.537(2) . ?
C9 C12 1.537(2) . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10' H10A 0.9900 . ?
C10' H10B 0.9900 . ?
C10' C11' 1.513(2) . ?
C10' N1' 1.5279(18) . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 C14 1.534(3) . ?
C11' H11A 0.9900 . ?
C11' H11B 0.9900 . ?
C11' C12' 1.524(2) . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 C13 1.532(2) . ?
C12' H12A 0.9900 . ?
C12' H12B 0.9900 . ?
C12' C13' 1.515(3) . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 C16 1.529(2) . ?
C13 H13 1.0000 . ?
C13 C15 1.522(3) . ?
C13 C17 1.534(3) . ?
C13' H13A 0.9800 . ?
C13' H13B 0.9800 . ?
C13' H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.531(3) . ?
C14 C18 1.525(3) . ?
C14' H14A 0.9900 . ?
C14' H14B 0.9900 . ?
C14' C15' 1.508(2) . ?
C14' N1' 1.5246(18) . ?
C15' H15A 0.9900 . ?
C15' H15B 0.9900 . ?
C15' C16' 1.523(2) . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C16' H16A 0.9900 . ?
C16' H16B 0.9900 . ?
C16' C17' 1.512(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.533(3) . ?
C16 C18 1.518(3) . ?
C17' H17A 0.9800 . ?
C17' H17B 0.9800 . ?
C17' H17C 0.9800 . ?
C17 H17D 0.9900 . ?
C17 H17E 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N1 O1 1.2292(18) . ?
N1 O2 1.2343(19) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?

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 N1 119.38(14) . . ?
C6 C1 C2 121.31(14) . . ?
C6 C1 N1 119.30(14) . . ?
H1'A C1' H1'B 107.4 . . ?
C2' C1' H1'A 108.3 . . ?
C2' C1' H1'B 108.3 . . ?
N1' C1' H1'A 108.3 . . ?
N1' C1' H1'B 108.3 . . ?
N1' C1' C2' 115.97(12) . . ?
C1' C2' H2'A 109.6 . . ?
C1' C2' H2'B 109.6 . . ?
C1' C2' C4' 110.37(13) . . ?
H2'A C2' H2'B 108.1 . . ?
C4' C2' H2'A 109.6 . . ?
C4' C2' H2'B 109.6 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.71(14) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.16(14) . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.78(14) . . ?
N2 C4 C3 116.80(13) . . ?
N2 C4 C5 124.42(14) . . ?
C2' C4' H4'A 109.1 . . ?
C2' C4' H4'B 109.1 . . ?
H4'A C4' H4'B 107.9 . . ?
C5' C4' C2' 112.43(13) . . ?
C5' C4' H4'A 109.1 . . ?
C5' C4' H4'B 109.1 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.04(14) . . ?
C6 C5 H5 120.0 . . ?
C4' C5' H5'A 109.5 . . ?
C4' C5' H5'B 109.5 . . ?
C4' C5' H5'C 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.00(15) . . ?
C5 C6 H6 120.0 . . ?
H6'A C6' H6'B 107.4 . . ?
C7' C6' H6'A 108.4 . . ?
C7' C6' H6'B 108.4 . . ?
C7' C6' N1' 115.68(12) . . ?
N1' C6' H6'A 108.4 . . ?
N1' C6' H6'B 108.4 . . ?
N3 C7 N2 111.98(13) . . ?
O3 C7 N2 123.48(14) . . ?
O3 C7 N3 124.53(15) . . ?
C6' C7' H7'A 109.5 . . ?
C6' C7' H7'B 109.5 . . ?
C6' C7' C8' 110.83(15) . . ?
H7'A C7' H7'B 108.1 . . ?
C8' C7' H7'A 109.5 . . ?
C8' C7' H7'B 109.5 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
N3 C8 H8A 108.8 . . ?
N3 C8 H8B 108.8 . . ?
N3 C8 C9 113.64(13) . . ?
C7' C8' H8'A 108.8 . . ?
C7' C8' H8'B 108.8 . . ?
H8'A C8' H8'B 107.7 . . ?
C9' C8' C7' 113.72(17) . . ?
C9' C8' H8'A 108.8 . . ?
C9' C8' H8'B 108.8 . . ?
C8 C9 C10 111.51(13) . . ?
C8 C9 C11 108.30(12) . . ?
C8 C9 C12 110.94(13) . . ?
C10 C9 C11 108.29(13) . . ?
C10 C9 C12 109.16(13) . . ?
C11 C9 C12 108.55(12) . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
H10A C10' H10B 107.3 . . ?
C11' C10' H10A 108.2 . . ?
C11' C10' H10B 108.2 . . ?
C11' C10' N1' 116.52(12) . . ?
N1' C10' H10A 108.2 . . ?
N1' C10' H10B 108.2 . . ?
C9 C10 H10C 109.6 . . ?
C9 C10 H10D 109.6 . . ?
C9 C10 C14 110.34(14) . . ?
H10C C10 H10D 108.1 . . ?
C14 C10 H10C 109.6 . . ?
C14 C10 H10D 109.6 . . ?
C10' C11' H11A 109.7 . . ?
C10' C11' H11B 109.7 . . ?
C10' C11' C12' 109.88(13) . . ?
H11A C11' H11B 108.2 . . ?
C12' C11' H11A 109.7 . . ?
C12' C11' H11B 109.7 . . ?
C9 C11 H11C 109.6 . . ?
C9 C11 H11D 109.6 . . ?
H11C C11 H11D 108.1 . . ?
C13 C11 C9 110.47(13) . . ?
C13 C11 H11C 109.6 . . ?
C13 C11 H11D 109.6 . . ?
C11' C12' H12A 109.1 . . ?
C11' C12' H12B 109.1 . . ?
H12A C12' H12B 107.8 . . ?
C13' C12' C11' 112.66(15) . . ?
C13' C12' H12A 109.1 . . ?
C13' C12' H12B 109.1 . . ?
C9 C12 H12C 109.6 . . ?
C9 C12 H12D 109.6 . . ?
H12C C12 H12D 108.1 . . ?
C16 C12 C9 110.22(14) . . ?
C16 C12 H12C 109.6 . . ?
C16 C12 H12D 109.6 . . ?
C11 C13 H13 109.5 . . ?
C11 C13 C17 108.90(15) . . ?
C15 C13 C11 109.75(15) . . ?
C15 C13 H13 109.5 . . ?
C15 C13 C17 109.66(17) . . ?
C17 C13 H13 109.5 . . ?
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 . . ?
C10 C14 H14 109.6 . . ?
C15 C14 C10 109.14(15) . . ?
C15 C14 H14 109.6 . . ?
C18 C14 C10 109.64(16) . . ?
C18 C14 H14 109.6 . . ?
C18 C14 C15 109.25(18) . . ?
H14A C14' H14B 107.4 . . ?
C15' C14' H14A 108.3 . . ?
C15' C14' H14B 108.3 . . ?
C15' C14' N1' 115.87(12) . . ?
N1' C14' H14A 108.3 . . ?
N1' C14' H14B 108.3 . . ?
C14' C15' H15A 109.8 . . ?
C14' C15' H15B 109.8 . . ?
C14' C15' C16' 109.38(13) . . ?
H15A C15' H15B 108.2 . . ?
C16' C15' H15A 109.8 . . ?
C16' C15' H15B 109.8 . . ?
C13 C15 C14 109.39(16) . . ?
C13 C15 H15C 109.8 . . ?
C13 C15 H15D 109.8 . . ?
C14 C15 H15C 109.8 . . ?
C14 C15 H15D 109.8 . . ?
H15C C15 H15D 108.2 . . ?
C15' C16' H16A 109.0 . . ?
C15' C16' H16B 109.0 . . ?
H16A C16' H16B 107.8 . . ?
C17' C16' C15' 112.79(16) . . ?
C17' C16' H16A 109.0 . . ?
C17' C16' H16B 109.0 . . ?
C12 C16 H16 109.5 . . ?
C12 C16 C17 109.47(16) . . ?
C17 C16 H16 109.5 . . ?
C18 C16 C12 109.54(16) . . ?
C18 C16 H16 109.5 . . ?
C18 C16 C17 109.19(17) . . ?
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 . . ?
C13 C17 H17D 109.8 . . ?
C13 C17 H17E 109.8 . . ?
C16 C17 C13 109.37(15) . . ?
C16 C17 H17D 109.8 . . ?
C16 C17 H17E 109.8 . . ?
H17D C17 H17E 108.2 . . ?
C14 C18 H18A 109.6 . . ?
C14 C18 H18B 109.6 . . ?
C16 C18 C14 110.12(15) . . ?
C16 C18 H18A 109.6 . . ?
C16 C18 H18B 109.6 . . ?
H18A C18 H18B 108.2 . . ?
O1 N1 C1 118.62(14) . . ?
O1 N1 O2 123.07(14) . . ?
O2 N1 C1 118.31(14) . . ?
C1' N1' C6' 111.33(11) . . ?
C1' N1' C10' 111.60(11) . . ?
C1' N1' C14' 106.19(10) . . ?
C6' N1' C10' 106.46(11) . . ?
C6' N1' C14' 110.39(11) . . ?
C14' N1' C10' 110.94(11) . . ?
C4 N2 C7 128.05(13) . . ?
C4 N2 H2A 116.0 . . ?
C7 N2 H2A 116.0 . . ?
C7 N3 C8 121.98(13) . . ?
C7 N3 H3A 119.0 . . ?
C8 N3 H3A 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.0(2) . . . . ?
C1' C2' C4' C5' 176.08(14) . . . . ?
C2' C1' N1' C6' -55.30(17) . . . . ?
C2' C1' N1' C10' 63.50(16) . . . . ?
C2' C1' N1' C14' -175.49(13) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 N1 O1 -174.64(14) . . . . ?
C2 C1 N1 O2 4.7(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 N2 -178.66(14) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C3 C4 N2 C7 176.61(14) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C5 C4 N2 C7 -2.5(2) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C1 N1 O1 3.9(2) . . . . ?
C6 C1 N1 O2 -176.77(15) . . . . ?
C6' C7' C8' C9' -73.9(2) . . . . ?
C7' C6' N1' C1' -59.75(16) . . . . ?
C7' C6' N1' C10' 178.41(13) . . . . ?
C7' C6' N1' C14' 57.93(16) . . . . ?
C8 C9 C10 C14 -178.71(14) . . . . ?
C8 C9 C11 C13 -179.99(13) . . . . ?
C8 C9 C12 C16 177.94(14) . . . . ?
C9 C8 N3 C7 104.36(17) . . . . ?
C9 C10 C14 C15 60.8(2) . . . . ?
C9 C10 C14 C18 -58.8(2) . . . . ?
C9 C11 C13 C15 -59.62(19) . . . . ?
C9 C11 C13 C17 60.42(19) . . . . ?
C9 C12 C16 C17 -60.1(2) . . . . ?
C9 C12 C16 C18 59.59(19) . . . . ?
C10' C11' C12' C13' -176.28(15) . . . . ?
C10 C9 C11 C13 58.94(17) . . . . ?
C10 C9 C12 C16 -58.78(18) . . . . ?
C10 C14 C15 C13 -60.0(2) . . . . ?
C10 C14 C18 C16 59.3(2) . . . . ?
C11' C10' N1' C1' 61.17(16) . . . . ?
C11' C10' N1' C6' -177.16(13) . . . . ?
C11' C10' N1' C14' -57.04(17) . . . . ?
C11 C9 C10 C14 -59.65(18) . . . . ?
C11 C9 C12 C16 59.06(18) . . . . ?
C11 C13 C15 C14 59.6(2) . . . . ?
C11 C13 C17 C16 -60.2(2) . . . . ?
C12 C9 C10 C14 58.36(18) . . . . ?
C12 C9 C11 C13 -59.46(18) . . . . ?
C12 C16 C17 C13 60.4(2) . . . . ?
C12 C16 C18 C14 -59.7(2) . . . . ?
C14' C15' C16' C17' -176.35(16) . . . . ?
C15' C14' N1' C1' 177.28(13) . . . . ?
C15' C14' N1' C6' 56.48(16) . . . . ?
C15' C14' N1' C10' -61.28(16) . . . . ?
C15 C13 C17 C16 59.9(2) . . . . ?
C15 C14 C18 C16 -60.3(2) . . . . ?
C17 C13 C15 C14 -60.0(2) . . . . ?
C17 C16 C18 C14 60.1(2) . . . . ?
C18 C14 C15 C13 59.8(2) . . . . ?
C18 C16 C17 C13 -59.6(2) . . . . ?
N1 C1 C2 C3 178.46(14) . . . . ?
N1 C1 C6 C5 -178.87(14) . . . . ?
N1' C1' C2' C4' -176.17(13) . . . . ?
N1' C6' C7' C8' 179.86(13) . . . . ?
N1' C10' C11' C12' 177.25(13) . . . . ?
N1' C14' C15' C16' 176.60(13) . . . . ?
N2 C4 C5 C6 178.18(15) . . . . ?
N2 C7 N3 C8 -169.76(13) . . . . ?
N3 C7 N2 C4 -175.33(14) . . . . ?
N3 C8 C9 C10 -58.16(18) . . . . ?
N3 C8 C9 C11 -177.22(13) . . . . ?
N3 C8 C9 C12 63.75(17) . . . . ?
O3 C7 N2 C4 3.8(3) . . . . ?
O3 C7 N3 C8 11.2(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 62.6 12.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.511
####################################################################### 
# 
# 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_21bh014
_database_code_depnum_ccdc_archive 'CCDC 2109212'
loop_
_audit_author_name
_audit_author_address
'Bryson Hawkins'
;Sydney School of Pharmacy, Faculty of Medicine and Health, The University of Sydney 
Australia
;
_audit_update_record             
;
2021-09-11 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_audit_creation_date             2021-07-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
bryson.hawkins@sydney.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N3 O4'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H23 N3 O4'
_chemical_oxdiff_usercomment     cd030
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   42.9415(11)
_cell_length_b                   6.2417(2)
_cell_length_c                   13.2277(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.680(2)
_cell_angle_gamma                90
_cell_volume                     3533.57(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18681
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      29.1430
_cell_measurement_theta_min      3.4900
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
30 7 7 0.1115
-48 0 -10 0.1010
47 5 5 0.0894
-57 -2 -4 0.0756
54 4 -1 0.0730
-60 -1 2 0.0822
55 3 -6 0.0870
-52 4 3 0.1108
27 -5 11 0.1410
-43 6 2 0.1298
37 -4 -13 0.1386
24 -5 13 0.1460
-13 8 8 0.1343
6 8 7 0.1277
-27 -3 -15 0.1368
-5 -8 -6 0.1591
-39 -7 -1 0.1155
51 5 -2 0.0738
-49 -5 3 0.1001
52 4 -8 0.0856
39 5 -11 0.1233
1 -5 15 0.1635
45 -1 -13 0.1213
-53 4 5 0.1124
-35 3 14 0.1803

_exptl_crystal_recrystallization_method 'Slow Evaporation fron DCM'
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.168
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
29.5011 6.8025 6.7994 0.3832 -0.9236 -0.0057
-48.1363 -0.1077 -10.0548 -0.4373 0.5103 0.7405
47.0591 4.7211 4.9206 0.6327 -0.7396 -0.2295
-57.2397 -1.5432 -3.6534 -0.7435 0.4544 0.4907
53.9880 3.9653 -0.5273 0.8436 -0.5161 -0.1483
-60.3493 -0.6863 1.6410 -0.8954 0.2140 0.3905
55.3819 2.7828 -6.0826 0.9714 -0.2326 -0.0476
-52.4784 4.2768 3.3076 -0.7288 -0.3031 0.6140
27.2205 -5.4305 11.3258 0.0079 0.0044 -1.0000
-43.2677 6.1196 2.3467 -0.5417 -0.4642 0.7007
37.0500 -3.8276 -13.1955 0.7554 0.6461 -0.1093
23.5768 -4.6189 13.4834 -0.0783 -0.1258 -0.9890
-13.3907 7.8656 7.5593 -0.2135 -0.8938 0.3944
6.3474 8.0446 7.0991 0.0766 -0.9623 0.2609
-26.6235 -2.5544 -15.1228 -0.0643 0.8188 0.5705
-4.8077 -8.2123 -6.3727 -0.0755 0.9475 -0.3107
-38.9842 -6.6587 -1.1486 -0.6464 0.7558 -0.1044
50.8091 4.7717 -2.1420 0.8529 -0.5220 -0.0092
-49.4531 -5.0337 2.7037 -0.8523 0.5215 -0.0399
51.6404 3.5004 -7.6014 0.9689 -0.2319 0.0865
39.3964 4.9124 -10.5823 0.8955 -0.2140 0.3902
1.0725 -5.2814 14.8528 -0.4380 -0.0356 -0.8983
45.1438 -1.1056 -13.2953 0.9235 0.3832 0.0178
-52.9504 3.8290 5.2630 -0.7902 -0.3273 0.5181
-34.5725 3.3044 14.4278 -0.7600 -0.6499 0.0092

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.856
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2474
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  40.00   1.00   20.00    --   11.41 -57.00 150.00   98
  2  ω    -15.00  83.00   1.00   20.00    --   11.41  57.00-180.00   98
  3  ω    -17.00  55.00   1.00   20.00    --   11.41  57.00  90.00   72
  4  ω      3.00  81.00   1.00   20.00    --   11.41  57.00 -60.00   78
  5  ω    -23.00  40.00   1.00   20.00    --   11.41 -57.00-150.00   63
  6  ω    -19.00  40.00   1.00   20.00    --   11.41 -57.00 -90.00   59
  7  ω    -55.00  40.00   1.00   20.00    --   11.41 -57.00  30.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0139745000
_diffrn_orient_matrix_UB_12      0.0193408000
_diffrn_orient_matrix_UB_13      -0.0236186000
_diffrn_orient_matrix_UB_21      -0.0034554000
_diffrn_orient_matrix_UB_22      -0.0875332000
_diffrn_orient_matrix_UB_23      -0.0332753000
_diffrn_orient_matrix_UB_31      -0.0082181000
_diffrn_orient_matrix_UB_32      0.0698420000
_diffrn_orient_matrix_UB_33      -0.0350511000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3157
_reflns_number_total             3615
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.029
_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)+(0.0431P)²+3.6324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C11(H11a,H11b), C13(H13a,H13b), C15(H15a,H15b), C17(H17a,
 H17b), C19(H19a,H19b), C20(H20a,H20b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), N2(H2a), N3(H3a)
;
_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
C21 C 0.54996(3) 0.2949(2) 0.48743(11) 0.0219(3) Uani 1 1 d . . . . .
H21A H 0.549556 0.436486 0.453570 0.026 Uiso 1 1 calc R U . . .
H21B H 0.544072 0.184821 0.435490 0.026 Uiso 1 1 calc R U . . .
C1 C 0.80291(3) 0.3413(2) 0.68868(10) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.78674(3) 0.5158(2) 0.64730(10) 0.0207(3) Uani 1 1 d . . . . .
H2 H 0.796671 0.651562 0.645193 0.025 Uiso 1 1 calc R U . . .
C3 C 0.75602(3) 0.4918(2) 0.60895(10) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.744939 0.610121 0.578497 0.024 Uiso 1 1 calc R U . . .
C4 C 0.74133(3) 0.2933(2) 0.61510(9) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.75840(3) 0.1165(2) 0.65454(10) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.748708 -0.020166 0.656169 0.022 Uiso 1 1 calc R U . . .
C6 C 0.78929(3) 0.1404(2) 0.69106(10) 0.0209(3) Uani 1 1 d . . . . .
H6 H 0.801002 0.020901 0.717389 0.025 Uiso 1 1 calc R U . . .
C7 C 0.68849(3) 0.4122(2) 0.55114(9) 0.0166(3) Uani 1 1 d . . . . .
C8 C 0.68579(3) 0.6463(2) 0.54799(10) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.65356(3) 0.6228(2) 0.49865(10) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.65717(3) 0.3863(2) 0.50887(10) 0.0178(3) Uani 1 1 d . . . . .
C11 C 0.60545(3) 0.2532(2) 0.45140(11) 0.0212(3) Uani 1 1 d . . . . .
H11A H 0.599276 0.138917 0.401864 0.025 Uiso 1 1 calc R U . . .
H11B H 0.603180 0.392215 0.415505 0.025 Uiso 1 1 calc R U . . .
C12 C 0.58313(3) 0.2491(2) 0.53611(10) 0.0185(3) Uani 1 1 d . . . . .
C13 C 0.59190(3) 0.4214(2) 0.61662(10) 0.0202(3) Uani 1 1 d . . . . .
H13A H 0.613081 0.392390 0.648972 0.024 Uiso 1 1 calc R U . . .
H13B H 0.592159 0.563925 0.583807 0.024 Uiso 1 1 calc R U . . .
C14 C 0.56832(3) 0.4221(2) 0.69737(11) 0.0242(3) Uani 1 1 d . . . . .
H14 H 0.574142 0.535829 0.748721 0.029 Uiso 1 1 calc R U . . .
C15 C 0.53553(3) 0.4673(2) 0.64717(12) 0.0280(3) Uani 1 1 d . . . . .
H15A H 0.520256 0.469549 0.699330 0.034 Uiso 1 1 calc R U . . .
H15B H 0.535187 0.609245 0.613690 0.034 Uiso 1 1 calc R U . . .
C16 C 0.52653(3) 0.2930(2) 0.56859(12) 0.0249(3) Uani 1 1 d . . . . .
H16 H 0.505095 0.322380 0.536198 0.030 Uiso 1 1 calc R U . . .
C17 C 0.52695(3) 0.0740(3) 0.62059(12) 0.0287(3) Uani 1 1 d . . . . .
H17A H 0.521042 -0.038822 0.569989 0.034 Uiso 1 1 calc R U . . .
H17B H 0.511616 0.072107 0.672562 0.034 Uiso 1 1 calc R U . . .
C18 C 0.55983(3) 0.0293(2) 0.67067(11) 0.0259(3) Uani 1 1 d . . . . .
H18 H 0.560107 -0.113894 0.704626 0.031 Uiso 1 1 calc R U . . .
C19 C 0.58308(3) 0.0293(2) 0.58874(11) 0.0220(3) Uani 1 1 d . . . . .
H19A H 0.577234 -0.083279 0.537987 0.026 Uiso 1 1 calc R U . . .
H19B H 0.604297 -0.003129 0.619945 0.026 Uiso 1 1 calc R U . . .
C20 C 0.56881(4) 0.2032(3) 0.74970(11) 0.0282(3) Uani 1 1 d . . . . .
H20A H 0.553858 0.202460 0.802842 0.034 Uiso 1 1 calc R U . . .
H20B H 0.589950 0.174130 0.782424 0.034 Uiso 1 1 calc R U . . .
N1 N 0.83482(3) 0.3716(2) 0.73432(9) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.70983(3) 0.26141(17) 0.58230(8) 0.0168(2) Uani 1 1 d . . . . .
H2A H 0.703136 0.128130 0.581905 0.020 Uiso 1 1 calc R U . . .
N3 N 0.63853(3) 0.22309(18) 0.48765(9) 0.0199(3) Uani 1 1 d . . . . .
H3A H 0.645974 0.092199 0.495253 0.024 Uiso 1 1 calc R U . . .
O1 O 0.85056(3) 0.2124(2) 0.75658(9) 0.0371(3) Uani 1 1 d . . . . .
O2 O 0.84404(3) 0.5561(2) 0.74921(10) 0.0468(3) Uani 1 1 d . . . . .
O3 O 0.70166(2) 0.80412(15) 0.57422(7) 0.0221(2) Uani 1 1 d . . . . .
O4 O 0.63367(2) 0.74940(16) 0.46553(8) 0.0257(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
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C12 1.5413(18) . ?
C21 C16 1.530(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.385(2) . ?
C1 N1 1.4638(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3824(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.3958(19) . ?
C4 C5 1.4019(19) . ?
C4 N2 1.4007(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3824(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.4658(19) . ?
C7 C10 1.4230(18) . ?
C7 N2 1.3543(17) . ?
C8 C9 1.4885(19) . ?
C8 O3 1.2315(16) . ?
C9 C10 1.4899(19) . ?
C9 O4 1.2184(17) . ?
C10 N3 1.3114(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.533(2) . ?
C11 N3 1.4740(17) . ?
C12 C13 1.5386(18) . ?
C12 C19 1.5386(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.530(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.533(2) . ?
C14 C20 1.531(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.532(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.530(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.535(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.532(2) . ?
C18 C20 1.534(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N1 O1 1.2243(17) . ?
N1 O2 1.2286(18) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?

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
H21A C21 H21B 108.2 . . ?
C12 C21 H21A 109.6 . . ?
C12 C21 H21B 109.6 . . ?
C16 C21 H21A 109.6 . . ?
C16 C21 H21B 109.6 . . ?
C16 C21 C12 110.09(11) . . ?
C2 C1 C6 121.57(12) . . ?
C2 C1 N1 119.03(13) . . ?
C6 C1 N1 119.36(13) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.62(13) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.81(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.70(12) . . ?
C3 C4 N2 122.54(12) . . ?
N2 C4 C5 117.75(12) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.17(13) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.02(13) . . ?
C5 C6 H6 120.5 . . ?
C10 C7 C8 91.87(11) . . ?
N2 C7 C8 138.71(12) . . ?
N2 C7 C10 129.39(12) . . ?
C7 C8 C9 89.02(10) . . ?
O3 C8 C7 138.47(13) . . ?
O3 C8 C9 132.50(12) . . ?
C8 C9 C10 88.37(10) . . ?
O4 C9 C8 133.90(13) . . ?
O4 C9 C10 137.73(13) . . ?
C7 C10 C9 90.61(11) . . ?
N3 C10 C7 135.51(13) . . ?
N3 C10 C9 133.88(12) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
N3 C11 H11A 108.8 . . ?
N3 C11 H11B 108.8 . . ?
N3 C11 C12 113.80(11) . . ?
C11 C12 C21 107.64(11) . . ?
C11 C12 C13 111.23(11) . . ?
C11 C12 C19 111.69(11) . . ?
C13 C12 C21 108.97(11) . . ?
C13 C12 C19 108.63(11) . . ?
C19 C12 C21 108.61(11) . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 C12 110.27(11) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C13 C14 H14 109.5 . . ?
C13 C14 C15 109.55(12) . . ?
C13 C14 C20 109.13(12) . . ?
C15 C14 H14 109.5 . . ?
C20 C14 H14 109.5 . . ?
C20 C14 C15 109.77(12) . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C14 109.57(12) . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C21 C16 C15 109.06(12) . . ?
C21 C16 H16 109.4 . . ?
C21 C16 C17 109.76(12) . . ?
C15 C16 H16 109.4 . . ?
C17 C16 C15 109.66(12) . . ?
C17 C16 H16 109.4 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
C16 C17 C18 109.44(12) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C17 C18 H18 109.5 . . ?
C19 C18 C17 108.92(12) . . ?
C19 C18 H18 109.5 . . ?
C19 C18 C20 109.86(12) . . ?
C20 C18 C17 109.69(13) . . ?
C20 C18 H18 109.5 . . ?
C12 C19 H19A 109.6 . . ?
C12 C19 H19B 109.6 . . ?
C18 C19 C12 110.18(11) . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C14 C20 C18 109.26(12) . . ?
C14 C20 H20A 109.8 . . ?
C14 C20 H20B 109.8 . . ?
C18 C20 H20A 109.8 . . ?
C18 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
O1 N1 C1 118.31(13) . . ?
O1 N1 O2 123.94(13) . . ?
O2 N1 C1 117.74(13) . . ?
C4 N2 H2A 116.3 . . ?
C7 N2 C4 127.42(11) . . ?
C7 N2 H2A 116.3 . . ?
C10 N3 C11 121.72(11) . . ?
C10 N3 H3A 119.1 . . ?
C11 N3 H3A 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C12 C13 C14 58.55(14) . . . . ?
C21 C12 C19 C18 -59.76(14) . . . . ?
C21 C16 C17 C18 60.09(16) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C1 C6 C5 -2.5(2) . . . . ?
C2 C1 N1 O1 -168.98(13) . . . . ?
C2 C1 N1 O2 12.0(2) . . . . ?
C2 C3 C4 C5 -3.86(19) . . . . ?
C2 C3 C4 N2 176.72(12) . . . . ?
C3 C4 C5 C6 2.67(19) . . . . ?
C3 C4 N2 C7 -7.4(2) . . . . ?
C4 C5 C6 C1 0.47(19) . . . . ?
C5 C4 N2 C7 173.16(12) . . . . ?
C6 C1 C2 C3 1.3(2) . . . . ?
C6 C1 N1 O1 13.19(19) . . . . ?
C6 C1 N1 O2 -165.86(13) . . . . ?
C7 C8 C9 C10 2.69(10) . . . . ?
C7 C8 C9 O4 -177.38(16) . . . . ?
C7 C10 N3 C11 174.31(14) . . . . ?
C8 C7 C10 C9 2.82(10) . . . . ?
C8 C7 C10 N3 -176.68(16) . . . . ?
C8 C7 N2 C4 -9.0(2) . . . . ?
C8 C9 C10 C7 -2.77(10) . . . . ?
C8 C9 C10 N3 176.74(15) . . . . ?
C9 C10 N3 C11 -5.0(2) . . . . ?
C10 C7 C8 C9 -2.82(10) . . . . ?
C10 C7 C8 O3 176.02(17) . . . . ?
C10 C7 N2 C4 173.76(13) . . . . ?
C11 C12 C13 C14 177.06(11) . . . . ?
C11 C12 C19 C18 -178.32(11) . . . . ?
C12 C21 C16 C15 60.49(15) . . . . ?
C12 C21 C16 C17 -59.67(15) . . . . ?
C12 C11 N3 C10 -93.78(15) . . . . ?
C12 C13 C14 C15 -59.31(15) . . . . ?
C12 C13 C14 C20 60.89(14) . . . . ?
C13 C12 C19 C18 58.63(14) . . . . ?
C13 C14 C15 C16 60.08(16) . . . . ?
C13 C14 C20 C18 -60.31(15) . . . . ?
C14 C15 C16 C21 -60.59(15) . . . . ?
C14 C15 C16 C17 59.63(16) . . . . ?
C15 C14 C20 C18 59.76(16) . . . . ?
C15 C16 C17 C18 -59.71(16) . . . . ?
C16 C21 C12 C11 -179.99(11) . . . . ?
C16 C21 C12 C13 -59.25(14) . . . . ?
C16 C21 C12 C19 58.93(14) . . . . ?
C16 C17 C18 C19 -60.34(16) . . . . ?
C16 C17 C18 C20 59.93(16) . . . . ?
C17 C18 C19 C12 60.76(15) . . . . ?
C17 C18 C20 C14 -59.86(16) . . . . ?
C19 C12 C13 C14 -59.61(14) . . . . ?
C19 C18 C20 C14 59.84(15) . . . . ?
C20 C14 C15 C16 -59.74(16) . . . . ?
C20 C18 C19 C12 -59.41(15) . . . . ?
N1 C1 C2 C3 -176.48(12) . . . . ?
N1 C1 C6 C5 175.28(12) . . . . ?
N2 C4 C5 C6 -177.89(12) . . . . ?
N2 C7 C8 C9 179.36(16) . . . . ?
N2 C7 C8 O3 -1.8(3) . . . . ?
N2 C7 C10 C9 -179.04(13) . . . . ?
N2 C7 C10 N3 1.5(3) . . . . ?
N3 C11 C12 C21 176.90(11) . . . . ?
N3 C11 C12 C13 57.60(15) . . . . ?
N3 C11 C12 C19 -63.96(14) . . . . ?
O3 C8 C9 C10 -176.27(15) . . . . ?
O3 C8 C9 O4 3.7(3) . . . . ?
O4 C9 C10 C7 177.30(17) . . . . ?
O4 C9 C10 N3 -3.2(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'Paratone N'
_olex2_submission_original_sample_id DM030
_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.773
