# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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 
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data_cu_TH_LD_18117_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1532870'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H33 N3 O6'
_chemical_formula_sum            'C23 H33 N3 O6'
_chemical_formula_weight         447.52

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.6856(3)
_cell_length_b                   9.6856(3)
_cell_length_c                   51.0690(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4790.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      72.83

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             1920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.740
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'SADABS (BRUKER, 20160)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33857
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_theta_min         4.883
_diffrn_reflns_theta_max         72.857
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4731
_reflns_number_gt                4378
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.995

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+2.0403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1606 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(8)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4731
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48842(18) 0.83869(18) 0.51224(3) 0.0315(4) Uani 1 1 d . . . . .
O2 O 0.72308(17) 0.70273(18) 0.60793(3) 0.0235(4) Uani 1 1 d . . . . .
O3 O 0.55286(17) 0.46638(17) 0.57253(3) 0.0235(4) Uani 1 1 d . . . . .
O4 O 0.40999(18) 0.16031(19) 0.64226(3) 0.0297(4) Uani 1 1 d . . . . .
O5 O 0.21589(18) 0.2102(2) 0.62017(3) 0.0323(4) Uani 1 1 d . . . . .
O6 O 0.42629(17) 0.62485(17) 0.52695(3) 0.0254(4) Uani 1 1 d . . . . .
N1 N 0.6247(2) 0.7099(2) 0.54006(4) 0.0232(4) Uani 1 1 d . . . . .
H1N H 0.6305 0.6285 0.5476 0.028 Uiso 1 1 calc R U . . .
N2 N 0.81576(19) 0.54967(19) 0.57947(3) 0.0187(4) Uani 1 1 d . . . . .
N3 N 0.5597(2) 0.3079(2) 0.60520(4) 0.0221(4) Uani 1 1 d . . . . .
H3N H 0.6028 0.2796 0.6194 0.026 Uiso 1 1 calc R U . . .
C1 C 0.5104(2) 0.7354(3) 0.52491(4) 0.0233(5) Uani 1 1 d . . . . .
C2 C 0.7335(2) 0.8037(2) 0.54443(4) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.8128(2) 0.7905(2) 0.56748(4) 0.0197(5) Uani 1 1 d . . . . .
C4 C 0.9162(2) 0.8853(3) 0.57272(4) 0.0238(5) Uani 1 1 d . . . . .
H4 H 0.9676 0.8777 0.5885 0.029 Uiso 1 1 calc R U . . .
C5 C 0.9461(3) 0.9910(3) 0.55538(5) 0.0269(5) Uani 1 1 d . . . . .
H5 H 1.0174 1.0554 0.5591 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8703(3) 1.0014(3) 0.53248(5) 0.0278(5) Uani 1 1 d . . . . .
H6 H 0.8912 1.0726 0.5203 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7643(3) 0.9097(3) 0.52697(5) 0.0257(5) Uani 1 1 d . . . . .
H7 H 0.7127 0.9191 0.5113 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7813(2) 0.6778(2) 0.58675(4) 0.0197(5) Uani 1 1 d . . . . .
C9 C 0.7710(2) 0.4288(2) 0.59437(4) 0.0191(5) Uani 1 1 d . . . . .
H9 H 0.7920 0.4399 0.6134 0.023 Uiso 1 1 calc R U . . .
C10 C 0.8538(3) 0.3081(3) 0.58243(5) 0.0258(5) Uani 1 1 d . . . . .
H10A H 0.8879 0.2452 0.5963 0.031 Uiso 1 1 calc R U . . .
H10B H 0.7963 0.2547 0.5700 0.031 Uiso 1 1 calc R U . . .
C11 C 0.9736(3) 0.3782(3) 0.56833(5) 0.0282(6) Uani 1 1 d . . . . .
H11B H 1.0511 0.3960 0.5805 0.034 Uiso 1 1 calc R U . . .
H11A H 1.0073 0.3206 0.5536 0.034 Uiso 1 1 calc R U . . .
C12 C 0.9121(2) 0.5128(2) 0.55835(4) 0.0225(5) Uani 1 1 d . . . . .
H12A H 0.9840 0.5844 0.5560 0.027 Uiso 1 1 calc R U . . .
H12B H 0.8630 0.4992 0.5415 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6171(2) 0.4055(2) 0.58988(4) 0.0188(5) Uani 1 1 d . . . . .
C14 C 0.4263(2) 0.2494(2) 0.59825(4) 0.0220(5) Uani 1 1 d . . . . .
H14 H 0.3694 0.3237 0.5900 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4432(3) 0.1306(3) 0.57816(5) 0.0287(6) Uani 1 1 d . . . . .
H15 H 0.5000 0.1680 0.5634 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3065(3) 0.0856(3) 0.56646(6) 0.0444(7) Uani 1 1 d . . . . .
H16B H 0.3235 0.0225 0.5518 0.067 Uiso 1 1 calc R U . . .
H16A H 0.2562 0.1669 0.5601 0.067 Uiso 1 1 calc R U . . .
H16C H 0.2515 0.0385 0.5799 0.067 Uiso 1 1 calc R U . . .
C17 C 0.5225(3) 0.0081(3) 0.58940(6) 0.0384(7) Uani 1 1 d . . . . .
H17B H 0.4710 -0.0309 0.6042 0.058 Uiso 1 1 calc R U . . .
H17C H 0.6134 0.0389 0.5954 0.058 Uiso 1 1 calc R U . . .
H17A H 0.5339 -0.0625 0.5758 0.058 Uiso 1 1 calc R U . . .
C18 C 0.3535(2) 0.2024(2) 0.62290(4) 0.0229(5) Uani 1 1 d . . . . .
C19 C 0.1355(3) 0.1541(3) 0.64166(5) 0.0405(7) Uani 1 1 d . . . . .
H19B H 0.1577 0.0562 0.6439 0.061 Uiso 1 1 calc R U . . .
H19A H 0.0369 0.1640 0.6378 0.061 Uiso 1 1 calc R U . . .
H19C H 0.1574 0.2044 0.6578 0.061 Uiso 1 1 calc R U . . .
C20 C 0.2867(2) 0.6275(3) 0.51534(4) 0.0230(5) Uani 1 1 d . . . . .
C21 C 0.2024(3) 0.7431(3) 0.52744(5) 0.0289(6) Uani 1 1 d . . . . .
H21A H 0.2083 0.7374 0.5466 0.043 Uiso 1 1 calc R U . . .
H21C H 0.1058 0.7342 0.5220 0.043 Uiso 1 1 calc R U . . .
H21B H 0.2387 0.8323 0.5216 0.043 Uiso 1 1 calc R U . . .
C22 C 0.2302(3) 0.4872(3) 0.52353(5) 0.0296(6) Uani 1 1 d . . . . .
H22B H 0.2887 0.4141 0.5163 0.044 Uiso 1 1 calc R U . . .
H22C H 0.1358 0.4766 0.5169 0.044 Uiso 1 1 calc R U . . .
H22A H 0.2297 0.4807 0.5427 0.044 Uiso 1 1 calc R U . . .
C23 C 0.2958(3) 0.6379(3) 0.48568(4) 0.0313(6) Uani 1 1 d . . . . .
H23C H 0.3260 0.7309 0.4808 0.047 Uiso 1 1 calc R U . . .
H23A H 0.2048 0.6195 0.4780 0.047 Uiso 1 1 calc R U . . .
H23B H 0.3623 0.5700 0.4791 0.047 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.211(3) . ?
O2 C8 1.243(3) . ?
O3 C13 1.233(3) . ?
O4 C18 1.201(3) . ?
O5 C18 1.342(3) . ?
O5 C19 1.451(3) . ?
O6 C1 1.349(3) . ?
O6 C20 1.477(3) . ?
N1 C1 1.373(3) . ?
N1 C2 1.409(3) . ?
N1 H1N 0.8800 . ?
N2 C8 1.337(3) . ?
N2 C9 1.462(3) . ?
N2 C12 1.470(3) . ?
N3 C13 1.347(3) . ?
N3 C14 1.455(3) . ?
N3 H3N 0.8800 . ?
C2 C7 1.392(3) . ?
C2 C3 1.411(3) . ?
C3 C4 1.386(3) . ?
C3 C8 1.501(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C13 1.525(3) . ?
C9 C10 1.543(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.525(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.522(3) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C18 1.513(3) . ?
C14 C15 1.550(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.517(4) . ?
C15 C17 1.525(4) . ?
C15 H15 1.0000 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.517(3) . ?
C20 C23 1.520(3) . ?
C20 C22 1.524(3) . ?
C21 H21A 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 H22A 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 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
C18 O5 C19 115.68(19) . . ?
C1 O6 C20 120.55(18) . . ?
C1 N1 C2 125.2(2) . . ?
C1 N1 H1N 117.4 . . ?
C2 N1 H1N 117.4 . . ?
C8 N2 C9 121.62(18) . . ?
C8 N2 C12 125.98(19) . . ?
C9 N2 C12 112.06(17) . . ?
C13 N3 C14 119.88(19) . . ?
C13 N3 H3N 120.1 . . ?
C14 N3 H3N 120.1 . . ?
O1 C1 O6 126.2(2) . . ?
O1 C1 N1 126.3(2) . . ?
O6 C1 N1 107.52(19) . . ?
C7 C2 N1 122.3(2) . . ?
C7 C2 C3 119.0(2) . . ?
N1 C2 C3 118.7(2) . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 C8 120.2(2) . . ?
C2 C3 C8 120.2(2) . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C7 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O2 C8 N2 122.4(2) . . ?
O2 C8 C3 121.4(2) . . ?
N2 C8 C3 116.21(18) . . ?
N2 C9 C13 109.25(18) . . ?
N2 C9 C10 104.32(17) . . ?
C13 C9 C10 109.65(19) . . ?
N2 C9 H9 111.1 . . ?
C13 C9 H9 111.1 . . ?
C10 C9 H9 111.1 . . ?
C11 C10 C9 104.15(19) . . ?
C11 C10 H10A 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C12 C11 C10 104.0(2) . . ?
C12 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
C12 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
H11B C11 H11A 109.0 . . ?
N2 C12 C11 102.16(18) . . ?
N2 C12 H12A 111.3 . . ?
C11 C12 H12A 111.3 . . ?
N2 C12 H12B 111.3 . . ?
C11 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
O3 C13 N3 123.0(2) . . ?
O3 C13 C9 122.1(2) . . ?
N3 C13 C9 114.82(19) . . ?
N3 C14 C18 109.15(18) . . ?
N3 C14 C15 110.86(19) . . ?
C18 C14 C15 112.1(2) . . ?
N3 C14 H14 108.2 . . ?
C18 C14 H14 108.2 . . ?
C15 C14 H14 108.2 . . ?
C16 C15 C17 111.3(2) . . ?
C16 C15 C14 112.4(2) . . ?
C17 C15 C14 112.4(2) . . ?
C16 C15 H15 106.7 . . ?
C17 C15 H15 106.7 . . ?
C14 C15 H15 106.7 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
O4 C18 O5 123.8(2) . . ?
O4 C18 C14 125.1(2) . . ?
O5 C18 C14 111.04(19) . . ?
O5 C19 H19B 109.5 . . ?
O5 C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
O6 C20 C21 110.00(19) . . ?
O6 C20 C23 110.38(19) . . ?
C21 C20 C23 112.8(2) . . ?
O6 C20 C22 101.71(19) . . ?
C21 C20 C22 110.7(2) . . ?
C23 C20 C22 110.7(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
C20 C23 H23C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
H23A C23 H23B 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
C20 O6 C1 O1 -6.5(4) . . . . ?
C20 O6 C1 N1 172.77(18) . . . . ?
C2 N1 C1 O1 3.3(4) . . . . ?
C2 N1 C1 O6 -176.0(2) . . . . ?
C1 N1 C2 C7 -24.5(4) . . . . ?
C1 N1 C2 C3 154.7(2) . . . . ?
C7 C2 C3 C4 2.1(3) . . . . ?
N1 C2 C3 C4 -177.2(2) . . . . ?
C7 C2 C3 C8 179.6(2) . . . . ?
N1 C2 C3 C8 0.3(3) . . . . ?
C2 C3 C4 C5 -1.8(4) . . . . ?
C8 C3 C4 C5 -179.3(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
N1 C2 C7 C6 178.4(2) . . . . ?
C3 C2 C7 C6 -0.9(4) . . . . ?
C9 N2 C8 O2 8.2(3) . . . . ?
C12 N2 C8 O2 -164.5(2) . . . . ?
C9 N2 C8 C3 -169.95(19) . . . . ?
C12 N2 C8 C3 17.4(3) . . . . ?
C4 C3 C8 O2 71.8(3) . . . . ?
C2 C3 C8 O2 -105.7(3) . . . . ?
C4 C3 C8 N2 -110.1(2) . . . . ?
C2 C3 C8 N2 72.5(3) . . . . ?
C8 N2 C9 C13 72.8(3) . . . . ?
C12 N2 C9 C13 -113.6(2) . . . . ?
C8 N2 C9 C10 -170.0(2) . . . . ?
C12 N2 C9 C10 3.6(2) . . . . ?
N2 C9 C10 C11 19.1(2) . . . . ?
C13 C9 C10 C11 136.0(2) . . . . ?
C9 C10 C11 C12 -34.1(2) . . . . ?
C8 N2 C12 C11 148.7(2) . . . . ?
C9 N2 C12 C11 -24.6(2) . . . . ?
C10 C11 C12 N2 35.5(2) . . . . ?
C14 N3 C13 O3 13.0(3) . . . . ?
C14 N3 C13 C9 -163.20(19) . . . . ?
N2 C9 C13 O3 12.0(3) . . . . ?
C10 C9 C13 O3 -101.7(2) . . . . ?
N2 C9 C13 N3 -171.78(18) . . . . ?
C10 C9 C13 N3 74.5(2) . . . . ?
C13 N3 C14 C18 -152.0(2) . . . . ?
C13 N3 C14 C15 84.0(3) . . . . ?
N3 C14 C15 C16 -168.9(2) . . . . ?
C18 C14 C15 C16 68.8(3) . . . . ?
N3 C14 C15 C17 64.5(3) . . . . ?
C18 C14 C15 C17 -57.8(3) . . . . ?
C19 O5 C18 O4 -4.4(4) . . . . ?
C19 O5 C18 C14 173.9(2) . . . . ?
N3 C14 C18 O4 -31.1(3) . . . . ?
C15 C14 C18 O4 92.1(3) . . . . ?
N3 C14 C18 O5 150.6(2) . . . . ?
C15 C14 C18 O5 -86.2(2) . . . . ?
C1 O6 C20 C21 -60.2(3) . . . . ?
C1 O6 C20 C23 65.0(3) . . . . ?
C1 O6 C20 C22 -177.50(19) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate-Pet Ether'
####################################################################### 
# 
# 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_mo_LLTRI_220816_0m
_database_code_depnum_ccdc_archive 'CCDC 1532871'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H33 N3 O6'
_chemical_formula_sum            'C23 H33 N3 O6'
_chemical_formula_weight         447.52

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.3238(5)
_cell_length_b                   7.2153(3)
_cell_length_c                   13.5409(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.1870(10)
_cell_angle_gamma                90
_cell_volume                     1187.48(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      30.44

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS (BRUKER, 20160)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41983
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         30.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7203
_reflns_number_gt                6847
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.2003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7203
_refine_ls_number_parameters     303
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.83405(10) 0.3874(2) 0.19848(11) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.62302(9) 0.34272(17) 0.51034(9) 0.0166(2) Uani 1 1 d . . . . .
O3 O 0.49774(9) 0.46741(17) 0.25586(9) 0.0161(2) Uani 1 1 d . . . . .
O4 O 0.16610(9) 0.77814(16) 0.18116(9) 0.0170(2) Uani 1 1 d . . . . .
O5 O 0.11788(9) 0.56061(17) 0.05075(9) 0.0190(2) Uani 1 1 d . . . . .
O6 O 0.65266(9) 0.46750(17) 0.12121(9) 0.0175(2) Uani 1 1 d . . . . .
N1 N 0.71868(10) 0.34315(19) 0.28413(10) 0.0129(2) Uani 1 1 d . . . . .
H1N H 0.6515(18) 0.381(4) 0.2763(17) 0.023(5) Uiso 1 1 d . . . . .
N2 N 0.66199(9) 0.59919(17) 0.43732(10) 0.0115(2) Uani 1 1 d . . . . .
N3 N 0.36249(9) 0.58859(18) 0.29715(10) 0.0119(2) Uani 1 1 d . . . . .
H3N H 0.3465(17) 0.661(3) 0.3425(17) 0.017(5) Uiso 1 1 d . . . . .
C1 C 0.74419(13) 0.3981(2) 0.20027(12) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.79936(11) 0.2881(2) 0.38583(12) 0.0115(2) Uani 1 1 d . . . . .
C3 C 0.78665(11) 0.3335(2) 0.48089(11) 0.0114(2) Uani 1 1 d . . . . .
C4 C 0.86491(12) 0.2751(2) 0.58123(12) 0.0156(3) Uani 1 1 d . . . . .
H4 H 0.8555 0.3047 0.6453 0.019 Uiso 1 1 calc R U . . .
C5 C 0.95657(12) 0.1738(2) 0.58836(13) 0.0182(3) Uani 1 1 d . . . . .
H5 H 1.0109 0.1378 0.6569 0.022 Uiso 1 1 calc R U . . .
C6 C 0.96756(12) 0.1263(2) 0.49406(14) 0.0171(3) Uani 1 1 d . . . . .
H6 H 1.0291 0.0547 0.4983 0.020 Uiso 1 1 calc R U . . .
C7 C 0.89019(12) 0.1815(2) 0.39375(12) 0.0149(3) Uani 1 1 d . . . . .
H7 H 0.8988 0.1469 0.3300 0.018 Uiso 1 1 calc R U . . .
C8 C 0.68453(11) 0.4265(2) 0.47785(11) 0.0115(3) Uani 1 1 d . . . . .
C9 C 0.55175(11) 0.6765(2) 0.40824(12) 0.0137(3) Uani 1 1 d . . . . .
H9 H 0.5315 0.6781 0.4717 0.016 Uiso 1 1 calc R U . . .
C10 C 0.56291(13) 0.8744(2) 0.37104(16) 0.0234(3) Uani 1 1 d . . . . .
H10B H 0.4920 0.9193 0.3156 0.028 Uiso 1 1 calc R U . . .
H10A H 0.5889 0.9618 0.4328 0.028 Uiso 1 1 calc R U . . .
C11 C 0.64846(13) 0.8513(2) 0.32363(14) 0.0209(3) Uani 1 1 d . . . . .
H11B H 0.6155 0.7952 0.2505 0.025 Uiso 1 1 calc R U . . .
H11A H 0.6823 0.9715 0.3196 0.025 Uiso 1 1 calc R U . . .
C12 C 0.73209(11) 0.7216(2) 0.40452(12) 0.0129(3) Uani 1 1 d . . . . .
H12B H 0.7727 0.6501 0.3702 0.015 Uiso 1 1 calc R U . . .
H12A H 0.7853 0.7910 0.4672 0.015 Uiso 1 1 calc R U . . .
C13 C 0.46903(11) 0.5651(2) 0.31405(11) 0.0120(2) Uani 1 1 d . . . . .
C14 C 0.27690(11) 0.5010(2) 0.20420(11) 0.0114(3) Uani 1 1 d . . . . .
H14 H 0.3101 0.4705 0.1520 0.014 Uiso 1 1 calc R U . . .
C15 C 0.23340(12) 0.3170(2) 0.23074(12) 0.0135(3) Uani 1 1 d . . . . .
H15 H 0.1847 0.2583 0.1605 0.016 Uiso 1 1 calc R U . . .
C16 C 0.16461(14) 0.3481(3) 0.29552(14) 0.0225(3) Uani 1 1 d . . . . .
H16B H 0.1423 0.2281 0.3140 0.034 Uiso 1 1 calc R U . . .
H16A H 0.0990 0.4203 0.2522 0.034 Uiso 1 1 calc R U . . .
H16C H 0.2083 0.4158 0.3621 0.034 Uiso 1 1 calc R U . . .
C17 C 0.32828(13) 0.1844(2) 0.28838(13) 0.0189(3) Uani 1 1 d . . . . .
H17B H 0.3753 0.2349 0.3596 0.028 Uiso 1 1 calc R U . . .
H17C H 0.3715 0.1692 0.2453 0.028 Uiso 1 1 calc R U . . .
H17A H 0.2991 0.0639 0.2973 0.028 Uiso 1 1 calc R U . . .
C18 C 0.18250(11) 0.6332(2) 0.14690(12) 0.0127(3) Uani 1 1 d . . . . .
C19 C 0.02183(14) 0.6668(3) -0.01493(15) 0.0272(4) Uani 1 1 d . . . . .
H19A H -0.0169 0.7063 0.0294 0.041 Uiso 1 1 calc R U . . .
H19B H -0.0272 0.5900 -0.0750 0.041 Uiso 1 1 calc R U . . .
H19C H 0.0444 0.7761 -0.0437 0.041 Uiso 1 1 calc R U . . .
C20 C 0.65865(16) 0.5442(3) 0.02308(15) 0.0269(4) Uani 1 1 d . . . . .
C21 C 0.54222(16) 0.6128(3) -0.04172(15) 0.0294(4) Uani 1 1 d . . . . .
H21C H 0.4909 0.5084 -0.0582 0.044 Uiso 1 1 calc R U . . .
H21A H 0.5375 0.6688 -0.1094 0.044 Uiso 1 1 calc R U . . .
H21B H 0.5231 0.7055 0.0006 0.044 Uiso 1 1 calc R U . . .
C22 C 0.6866(2) 0.3892(5) -0.03807(17) 0.0523(8) Uani 1 1 d . . . . .
H22B H 0.7631 0.3503 0.0027 0.078 Uiso 1 1 calc R U . . .
H22C H 0.6773 0.4341 -0.1096 0.078 Uiso 1 1 calc R U . . .
H22A H 0.6375 0.2836 -0.0465 0.078 Uiso 1 1 calc R U . . .
C23 C 0.7386(2) 0.7044(5) 0.0530(2) 0.0528(7) Uani 1 1 d . . . . .
H23C H 0.7217 0.7903 0.1001 0.079 Uiso 1 1 calc R U . . .
H23A H 0.7322 0.7693 -0.0129 0.079 Uiso 1 1 calc R U . . .
H23B H 0.8138 0.6575 0.0911 0.079 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2098(19) . ?
O2 C8 1.2356(18) . ?
O3 C13 1.2292(18) . ?
O4 C18 1.2000(19) . ?
O5 C18 1.3387(18) . ?
O5 C19 1.4431(19) . ?
O6 C1 1.3470(18) . ?
O6 C20 1.471(2) . ?
N1 C1 1.3706(19) . ?
N1 C2 1.4130(18) . ?
N1 H1N 0.90(2) . ?
N2 C8 1.3446(19) . ?
N2 C9 1.4663(17) . ?
N2 C12 1.4799(18) . ?
N3 C13 1.3527(18) . ?
N3 C14 1.4518(17) . ?
N3 H3N 0.90(2) . ?
C2 C7 1.400(2) . ?
C2 C3 1.404(2) . ?
C3 C4 1.3964(19) . ?
C3 C8 1.5027(19) . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C13 1.529(2) . ?
C9 C10 1.541(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.529(3) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 C12 1.522(2) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C14 C18 1.5145(19) . ?
C14 C15 1.549(2) . ?
C14 H14 1.0000 . ?
C15 C17 1.521(2) . ?
C15 C16 1.523(2) . ?
C15 H15 1.0000 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17A 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C23 1.510(4) . ?
C20 C21 1.518(3) . ?
C20 C22 1.526(3) . ?
C21 H21C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 H22A 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 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
C18 O5 C19 116.51(13) . . ?
C1 O6 C20 119.41(13) . . ?
C1 N1 C2 122.73(12) . . ?
C1 N1 H1N 112.8(14) . . ?
C2 N1 H1N 121.5(14) . . ?
C8 N2 C9 119.60(12) . . ?
C8 N2 C12 127.79(12) . . ?
C9 N2 C12 112.21(12) . . ?
C13 N3 C14 119.29(12) . . ?
C13 N3 H3N 119.0(14) . . ?
C14 N3 H3N 121.7(14) . . ?
O1 C1 O6 126.08(14) . . ?
O1 C1 N1 125.57(15) . . ?
O6 C1 N1 108.35(12) . . ?
C7 C2 C3 118.87(13) . . ?
C7 C2 N1 121.16(13) . . ?
C3 C2 N1 119.91(12) . . ?
C4 C3 C2 119.95(13) . . ?
C4 C3 C8 117.92(12) . . ?
C2 C3 C8 121.80(12) . . ?
C5 C4 C3 120.67(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.12(14) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 120.97(14) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.38(14) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
O2 C8 N2 121.94(13) . . ?
O2 C8 C3 119.79(13) . . ?
N2 C8 C3 118.26(12) . . ?
N2 C9 C13 108.92(12) . . ?
N2 C9 C10 102.72(12) . . ?
C13 C9 C10 110.35(13) . . ?
N2 C9 H9 111.5 . . ?
C13 C9 H9 111.5 . . ?
C10 C9 H9 111.5 . . ?
C11 C10 C9 102.98(13) . . ?
C11 C10 H10B 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10A 111.2 . . ?
H10B C10 H10A 109.1 . . ?
C12 C11 C10 102.52(14) . . ?
C12 C11 H11B 111.3 . . ?
C10 C11 H11B 111.3 . . ?
C12 C11 H11A 111.3 . . ?
C10 C11 H11A 111.3 . . ?
H11B C11 H11A 109.2 . . ?
N2 C12 C11 102.52(11) . . ?
N2 C12 H12B 111.3 . . ?
C11 C12 H12B 111.3 . . ?
N2 C12 H12A 111.3 . . ?
C11 C12 H12A 111.3 . . ?
H12B C12 H12A 109.2 . . ?
O3 C13 N3 122.96(13) . . ?
O3 C13 C9 121.94(13) . . ?
N3 C13 C9 115.03(12) . . ?
N3 C14 C18 111.26(12) . . ?
N3 C14 C15 114.06(11) . . ?
C18 C14 C15 110.33(11) . . ?
N3 C14 H14 106.9 . . ?
C18 C14 H14 106.9 . . ?
C15 C14 H14 106.9 . . ?
C17 C15 C16 111.53(13) . . ?
C17 C15 C14 110.29(12) . . ?
C16 C15 C14 112.22(13) . . ?
C17 C15 H15 107.5 . . ?
C16 C15 H15 107.5 . . ?
C14 C15 H15 107.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
O4 C18 O5 124.79(13) . . ?
O4 C18 C14 126.53(13) . . ?
O5 C18 C14 108.67(12) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C20 C23 109.81(17) . . ?
O6 C20 C21 102.94(14) . . ?
C23 C20 C21 110.30(18) . . ?
O6 C20 C22 109.27(17) . . ?
C23 C20 C22 113.8(2) . . ?
C21 C20 C22 110.14(18) . . ?
C20 C21 H21C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
H21C C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
C20 C23 H23C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
H23A C23 H23B 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
C20 O6 C1 O1 -1.9(3) . . . . ?
C20 O6 C1 N1 177.42(15) . . . . ?
C2 N1 C1 O1 8.4(3) . . . . ?
C2 N1 C1 O6 -170.90(13) . . . . ?
C1 N1 C2 C7 -39.3(2) . . . . ?
C1 N1 C2 C3 143.56(15) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
N1 C2 C3 C4 178.36(14) . . . . ?
C7 C2 C3 C8 -172.23(13) . . . . ?
N1 C2 C3 C8 5.0(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C8 C3 C4 C5 174.38(14) . . . . ?
C3 C4 C5 C6 -2.1(2) . . . . ?
C4 C5 C6 C7 1.5(2) . . . . ?
C5 C6 C7 C2 0.4(2) . . . . ?
C3 C2 C7 C6 -1.7(2) . . . . ?
N1 C2 C7 C6 -178.93(14) . . . . ?
C9 N2 C8 O2 -13.7(2) . . . . ?
C12 N2 C8 O2 174.22(13) . . . . ?
C9 N2 C8 C3 164.99(12) . . . . ?
C12 N2 C8 C3 -7.1(2) . . . . ?
C4 C3 C8 O2 -59.69(19) . . . . ?
C2 C3 C8 O2 113.78(16) . . . . ?
C4 C3 C8 N2 121.60(15) . . . . ?
C2 C3 C8 N2 -64.93(18) . . . . ?
C8 N2 C9 C13 -65.36(17) . . . . ?
C12 N2 C9 C13 107.90(13) . . . . ?
C8 N2 C9 C10 177.62(13) . . . . ?
C12 N2 C9 C10 -9.12(15) . . . . ?
N2 C9 C10 C11 30.96(15) . . . . ?
C13 C9 C10 C11 -85.04(14) . . . . ?
C9 C10 C11 C12 -41.46(15) . . . . ?
C8 N2 C12 C11 156.12(14) . . . . ?
C9 N2 C12 C11 -16.46(15) . . . . ?
C10 C11 C12 N2 35.23(15) . . . . ?
C14 N3 C13 O3 -2.3(2) . . . . ?
C14 N3 C13 C9 174.90(13) . . . . ?
N2 C9 C13 O3 -19.1(2) . . . . ?
C10 C9 C13 O3 92.91(17) . . . . ?
N2 C9 C13 N3 163.59(13) . . . . ?
C10 C9 C13 N3 -84.35(16) . . . . ?
C13 N3 C14 C18 -135.72(14) . . . . ?
C13 N3 C14 C15 98.68(16) . . . . ?
N3 C14 C15 C17 -53.86(16) . . . . ?
C18 C14 C15 C17 -179.94(12) . . . . ?
N3 C14 C15 C16 71.14(16) . . . . ?
C18 C14 C15 C16 -54.94(16) . . . . ?
C19 O5 C18 O4 -0.2(2) . . . . ?
C19 O5 C18 C14 178.94(14) . . . . ?
N3 C14 C18 O4 -13.7(2) . . . . ?
C15 C14 C18 O4 113.96(16) . . . . ?
N3 C14 C18 O5 167.23(12) . . . . ?
C15 C14 C18 O5 -65.13(15) . . . . ?
C1 O6 C20 C23 -60.4(2) . . . . ?
C1 O6 C20 C21 -177.88(15) . . . . ?
C1 O6 C20 C22 65.1(2) . . . . ?

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
N1 H1N O3 0.90(2) 2.05(2) 2.9482(16) 179(2) .
N1 H1N N2 0.90(2) 2.65(2) 3.0934(18) 111.6(17) .
N3 H3N O2 0.90(2) 2.28(2) 3.1276(17) 158.1(19) 2_656
C23 H23B O1 0.98 2.38 2.946(3) 116.1 .
C22 H22B O1 0.98 2.44 2.994(3) 115.5 .
C12 H12B N1 0.99 2.47 3.148(2) 125.4 .
C9 H9 O2 1.00 2.47 3.1905(18) 128.2 2_656

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate-Pet Ether'
