# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1947434'
loop_
_audit_author_name
_audit_author_address
'Weiwei Gao'
;Lanzhou University
China
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2021-02-02 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         ?
_chemical_formula_sum            'C16 H21 N O3'
_chemical_formula_weight         275.34

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1376(12)
_cell_length_b                   14.5412(13)
_cell_length_c                   15.0949(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.733(2)
_cell_angle_gamma                90
_cell_volume                     2812.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2863
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      24.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   0.6734
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            14277
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.968
_diffrn_reflns_theta_max         25.169
_diffrn_reflns_theta_full        25.169
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5025
_reflns_number_gt                3391
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0950P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5025
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
C1 C -0.17273(16) 0.83379(19) 0.11151(16) 0.0727(7) Uani 1 1 d . . . . .
H1A H -0.2419 0.8352 0.1243 0.087 Uiso 1 1 calc R U . . .
H1B H -0.1713 0.7878 0.0653 0.087 Uiso 1 1 calc R U . . .
C2 C -0.14264(18) 0.9264(2) 0.08218(18) 0.0849(8) Uani 1 1 d . . . . .
H2A H -0.1725 0.9751 0.1124 0.102 Uiso 1 1 calc R U . . .
H2B H -0.1660 0.9340 0.0170 0.102 Uiso 1 1 calc R U . . .
C3 C -0.02490(17) 0.92782(15) 0.10994(15) 0.0610(6) Uani 1 1 d . . . . .
H3A H -0.0004 0.9870 0.1358 0.073 Uiso 1 1 calc R U . . .
H3B H 0.0055 0.9162 0.0580 0.073 Uiso 1 1 calc R U . . .
C4 C 0.00448(14) 0.85153(12) 0.18065(12) 0.0426(5) Uani 1 1 d . . . . .
C5 C 0.14689(14) 0.75238(13) 0.20487(14) 0.0457(5) Uani 1 1 d . . . . .
C6 C 0.15200(13) 0.80807(13) 0.28699(13) 0.0434(5) Uani 1 1 d . . . . .
C7 C 0.07649(13) 0.87055(12) 0.27045(12) 0.0392(4) Uani 1 1 d . . . . .
C8 C 0.21753(15) 0.79036(17) 0.37958(14) 0.0606(6) Uani 1 1 d . . . . .
H8A H 0.2766 0.8321 0.3930 0.073 Uiso 1 1 calc R U . . .
H8B H 0.2431 0.7276 0.3849 0.073 Uiso 1 1 calc R U . . .
C9 C 0.14352(17) 0.80740(17) 0.44332(14) 0.0625(6) Uani 1 1 d . . . . .
H9 H 0.1822 0.7964 0.5057 0.075 Uiso 1 1 calc R U . . .
C10 C 0.10716(19) 0.90740(18) 0.43629(14) 0.0715(7) Uani 1 1 d . . . . .
H10A H 0.1644 0.9457 0.4675 0.086 Uiso 1 1 calc R U . . .
H10B H 0.0509 0.9137 0.4680 0.086 Uiso 1 1 calc R U . . .
C11 C 0.06853(16) 0.94500(14) 0.33747(14) 0.0536(5) Uani 1 1 d . . . . .
H11 H 0.1208 0.9908 0.3300 0.064 Uiso 1 1 calc R U . . .
C12 C -0.03411(18) 0.99826(15) 0.32346(17) 0.0699(7) Uani 1 1 d . . . . .
H12A H -0.0481 1.0272 0.2648 0.105 Uiso 1 1 calc R U . . .
H12B H -0.0288 1.0444 0.3698 0.105 Uiso 1 1 calc R U . . .
H12C H -0.0898 0.9567 0.3270 0.105 Uiso 1 1 calc R U . . .
C13 C 0.05640(18) 0.73585(18) 0.42031(15) 0.0631(6) Uani 1 1 d . . . . .
C14 C -0.05708(17) 0.76542(17) 0.39832(16) 0.0685(7) Uani 1 1 d . . . . .
H14A H -0.0603 0.8304 0.3836 0.082 Uiso 1 1 calc R U . . .
H14B H -0.0849 0.7576 0.4523 0.082 Uiso 1 1 calc R U . . .
C15 C -0.12665(17) 0.71374(18) 0.32049(17) 0.0741(7) Uani 1 1 d . . . . .
H15A H -0.1276 0.6493 0.3369 0.089 Uiso 1 1 calc R U . . .
H15B H -0.1973 0.7370 0.3125 0.089 Uiso 1 1 calc R U . . .
C16 C -0.09371(17) 0.72114(14) 0.23100(16) 0.0619(6) Uani 1 1 d . . . . .
H16A H -0.0240 0.6958 0.2387 0.074 Uiso 1 1 calc R U . . .
H16B H -0.1401 0.6833 0.1867 0.074 Uiso 1 1 calc R U . . .
C17 C 0.67046(16) 0.57575(17) 0.93323(15) 0.0633(6) Uani 1 1 d . . . . .
H17A H 0.7418 0.5778 0.9255 0.076 Uiso 1 1 calc R U . . .
H17B H 0.6640 0.5268 0.9753 0.076 Uiso 1 1 calc R U . . .
C18 C 0.63814(17) 0.66706(18) 0.96584(16) 0.0743(7) Uani 1 1 d . . . . .
H18A H 0.6698 0.7176 0.9398 0.089 Uiso 1 1 calc R U . . .
H18B H 0.6579 0.6713 1.0315 0.089 Uiso 1 1 calc R U . . .
C19 C 0.52063(16) 0.66802(16) 0.93301(14) 0.0596(6) Uani 1 1 d . . . . .
H19A H 0.4964 0.7290 0.9122 0.072 Uiso 1 1 calc R U . . .
H19B H 0.4870 0.6498 0.9814 0.072 Uiso 1 1 calc R U . . .
C20 C 0.49655(13) 0.59882(12) 0.85443(12) 0.0406(4) Uani 1 1 d . . . . .
C21 C 0.35295(14) 0.50318(13) 0.80827(13) 0.0452(5) Uani 1 1 d . . . . .
C22 C 0.35753(13) 0.56653(12) 0.73392(13) 0.0411(5) Uani 1 1 d . . . . .
C23 C 0.43373(13) 0.62737(11) 0.76312(12) 0.0372(4) Uani 1 1 d . . . . .
C24 C 0.30196(15) 0.55785(15) 0.63691(14) 0.0548(5) Uani 1 1 d . . . . .
H24A H 0.2431 0.5998 0.6229 0.066 Uiso 1 1 calc R U . . .
H24B H 0.2769 0.4956 0.6235 0.066 Uiso 1 1 calc R U . . .
C25 C 0.38416(15) 0.58281(14) 0.58253(13) 0.0522(5) Uani 1 1 d . . . . .
H25 H 0.3510 0.5786 0.5178 0.063 Uiso 1 1 calc R U . . .
C26 C 0.42031(17) 0.68168(15) 0.60257(14) 0.0582(6) Uani 1 1 d . . . . .
H26A H 0.3652 0.7225 0.5721 0.070 Uiso 1 1 calc R U . . .
H26B H 0.4805 0.6923 0.5765 0.070 Uiso 1 1 calc R U . . .
C27 C 0.45002(15) 0.70829(12) 0.70572(14) 0.0480(5) Uani 1 1 d . . . . .
H27 H 0.3974 0.7535 0.7137 0.058 Uiso 1 1 calc R U . . .
C28 C 0.55482(16) 0.75877(14) 0.73352(17) 0.0614(6) Uani 1 1 d . . . . .
H28A H 0.5592 0.7885 0.7910 0.092 Uiso 1 1 calc R U . . .
H28B H 0.5600 0.8040 0.6884 0.092 Uiso 1 1 calc R U . . .
H28C H 0.6109 0.7154 0.7385 0.092 Uiso 1 1 calc R U . . .
C29 C 0.47084(16) 0.51044(15) 0.60337(13) 0.0487(5) Uani 1 1 d . . . . .
C30 C 0.58283(15) 0.53780(14) 0.64220(13) 0.0497(5) Uani 1 1 d . . . . .
H30A H 0.5834 0.5996 0.6665 0.060 Uiso 1 1 calc R U . . .
H30B H 0.6196 0.5396 0.5931 0.060 Uiso 1 1 calc R U . . .
C31 C 0.64229(16) 0.47525(14) 0.71624(15) 0.0560(6) Uani 1 1 d . . . . .
H31A H 0.6412 0.4132 0.6925 0.067 Uiso 1 1 calc R U . . .
H31B H 0.7145 0.4951 0.7323 0.067 Uiso 1 1 calc R U . . .
C32 C 0.59907(16) 0.47373(13) 0.80116(14) 0.0512(5) Uani 1 1 d . . . . .
H32A H 0.5286 0.4496 0.7856 0.061 Uiso 1 1 calc R U . . .
H32B H 0.6407 0.4316 0.8443 0.061 Uiso 1 1 calc R U . . .
N1 N -0.09341(11) 0.81499(11) 0.19370(11) 0.0479(4) Uani 1 1 d . . . . .
N2 N 0.59670(11) 0.56324(10) 0.84604(10) 0.0431(4) Uani 1 1 d . . . . .
O1 O 0.06339(10) 0.78041(9) 0.14085(9) 0.0490(4) Uani 1 1 d . . . . .
O2 O 0.20512(11) 0.69352(10) 0.18949(11) 0.0660(4) Uani 1 1 d . . . . .
O3 O 0.07872(14) 0.65502(13) 0.41900(13) 0.0866(6) Uani 1 1 d . . . . .
O4 O 0.43052(10) 0.52500(9) 0.88075(9) 0.0493(4) Uani 1 1 d . . . . .
O5 O 0.29179(11) 0.44220(10) 0.81194(11) 0.0642(4) Uani 1 1 d . . . . .
O6 O 0.44877(12) 0.43014(10) 0.58717(10) 0.0663(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.459(3) . ?
C1 C2 1.498(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.529(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.445(2) . ?
C4 O1 1.495(2) . ?
C4 C7 1.498(2) . ?
C5 O2 1.204(2) . ?
C5 O1 1.355(2) . ?
C5 C6 1.470(3) . ?
C6 C7 1.328(2) . ?
C6 C8 1.494(3) . ?
C7 C11 1.501(3) . ?
C8 C9 1.531(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.527(3) . ?
C9 C13 1.529(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.564(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.529(3) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O3 1.213(3) . ?
C13 C14 1.516(3) . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.510(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N1 1.477(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.464(2) . ?
C17 C18 1.509(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.514(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.534(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N2 1.445(2) . ?
C20 O4 1.488(2) . ?
C20 C23 1.501(2) . ?
C21 O5 1.206(2) . ?
C21 O4 1.358(2) . ?
C21 C22 1.463(3) . ?
C22 C23 1.336(2) . ?
C22 C24 1.491(3) . ?
C23 C27 1.504(3) . ?
C24 C25 1.537(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.523(3) . ?
C25 C29 1.532(3) . ?
C25 H25 0.9800 . ?
C26 C27 1.568(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.535(3) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 O6 1.215(2) . ?
C29 C30 1.512(3) . ?
C30 C31 1.517(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.512(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N2 1.471(2) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 103.54(19) . . ?
N1 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.0 . . ?
C1 C2 C3 104.52(18) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 105.64(18) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
N1 C4 O1 110.83(14) . . ?
N1 C4 C7 110.38(15) . . ?
O1 C4 C7 102.23(13) . . ?
N1 C4 C3 105.47(16) . . ?
O1 C4 C3 107.15(15) . . ?
C7 C4 C3 120.65(17) . . ?
O2 C5 O1 121.69(19) . . ?
O2 C5 C6 129.89(19) . . ?
O1 C5 C6 108.36(15) . . ?
C7 C6 C5 108.97(17) . . ?
C7 C6 C8 123.14(18) . . ?
C5 C6 C8 127.16(18) . . ?
C6 C7 C4 109.91(16) . . ?
C6 C7 C11 121.80(18) . . ?
C4 C7 C11 128.26(16) . . ?
C6 C8 C9 104.20(16) . . ?
C6 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
C6 C8 H8B 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C13 115.16(19) . . ?
C10 C9 C8 110.04(19) . . ?
C13 C9 C8 107.12(19) . . ?
C10 C9 H9 108.1 . . ?
C13 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C9 C10 C11 115.45(17) . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C7 C11 C12 117.54(17) . . ?
C7 C11 C10 109.54(17) . . ?
C12 C11 C10 113.57(19) . . ?
C7 C11 H11 105.0 . . ?
C12 C11 H11 105.0 . . ?
C10 C11 H11 105.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 120.1(2) . . ?
O3 C13 C9 119.5(2) . . ?
C14 C13 C9 120.5(2) . . ?
C13 C14 C15 115.1(2) . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 C14 114.47(18) . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
N1 C16 C15 115.61(19) . . ?
N1 C16 H16A 108.4 . . ?
C15 C16 H16A 108.4 . . ?
N1 C16 H16B 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.4 . . ?
N2 C17 C18 102.98(17) . . ?
N2 C17 H17A 111.2 . . ?
C18 C17 H17A 111.2 . . ?
N2 C17 H17B 111.2 . . ?
C18 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C17 C18 C19 103.96(18) . . ?
C17 C18 H18A 111.0 . . ?
C19 C18 H18A 111.0 . . ?
C17 C18 H18B 111.0 . . ?
C19 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C18 C19 C20 105.58(17) . . ?
C18 C19 H19A 110.6 . . ?
C20 C19 H19A 110.6 . . ?
C18 C19 H19B 110.6 . . ?
C20 C19 H19B 110.6 . . ?
H19A C19 H19B 108.8 . . ?
N2 C20 O4 111.14(14) . . ?
N2 C20 C23 110.23(14) . . ?
O4 C20 C23 102.11(13) . . ?
N2 C20 C19 105.43(15) . . ?
O4 C20 C19 107.43(14) . . ?
C23 C20 C19 120.43(16) . . ?
O5 C21 O4 121.60(19) . . ?
O5 C21 C22 129.68(19) . . ?
O4 C21 C22 108.68(15) . . ?
C23 C22 C21 108.56(17) . . ?
C23 C22 C24 123.32(18) . . ?
C21 C22 C24 127.30(17) . . ?
C22 C23 C20 109.89(16) . . ?
C22 C23 C27 121.29(17) . . ?
C20 C23 C27 128.77(16) . . ?
C22 C24 C25 104.78(15) . . ?
C22 C24 H24A 110.8 . . ?
C25 C24 H24A 110.8 . . ?
C22 C24 H24B 110.8 . . ?
C25 C24 H24B 110.8 . . ?
H24A C24 H24B 108.9 . . ?
C26 C25 C29 115.00(17) . . ?
C26 C25 C24 109.99(17) . . ?
C29 C25 C24 107.83(17) . . ?
C26 C25 H25 107.9 . . ?
C29 C25 H25 107.9 . . ?
C24 C25 H25 107.9 . . ?
C25 C26 C27 115.37(16) . . ?
C25 C26 H26A 108.4 . . ?
C27 C26 H26A 108.4 . . ?
C25 C26 H26B 108.4 . . ?
C27 C26 H26B 108.4 . . ?
H26A C26 H26B 107.5 . . ?
C23 C27 C28 116.71(16) . . ?
C23 C27 C26 110.06(15) . . ?
C28 C27 C26 113.67(17) . . ?
C23 C27 H27 105.1 . . ?
C28 C27 H27 105.1 . . ?
C26 C27 H27 105.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O6 C29 C30 119.97(19) . . ?
O6 C29 C25 119.04(19) . . ?
C30 C29 C25 120.98(18) . . ?
C29 C30 C31 115.26(18) . . ?
C29 C30 H30A 108.5 . . ?
C31 C30 H30A 108.5 . . ?
C29 C30 H30B 108.5 . . ?
C31 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C32 C31 C30 113.87(16) . . ?
C32 C31 H31A 108.8 . . ?
C30 C31 H31A 108.8 . . ?
C32 C31 H31B 108.8 . . ?
C30 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
N2 C32 C31 115.31(16) . . ?
N2 C32 H32A 108.4 . . ?
C31 C32 H32A 108.4 . . ?
N2 C32 H32B 108.4 . . ?
C31 C32 H32B 108.4 . . ?
H32A C32 H32B 107.5 . . ?
C4 N1 C1 107.79(16) . . ?
C4 N1 C16 117.98(15) . . ?
C1 N1 C16 115.84(17) . . ?
C20 N2 C17 108.17(15) . . ?
C20 N2 C32 117.99(15) . . ?
C17 N2 C32 116.56(16) . . ?
C5 O1 C4 109.33(14) . . ?
C21 O4 C20 109.36(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 33.2(2) . . . . ?
C1 C2 C3 C4 -18.5(3) . . . . ?
C2 C3 C4 N1 -3.1(2) . . . . ?
C2 C3 C4 O1 115.00(19) . . . . ?
C2 C3 C4 C7 -128.9(2) . . . . ?
O2 C5 C6 C7 174.13(19) . . . . ?
O1 C5 C6 C7 -3.0(2) . . . . ?
O2 C5 C6 C8 -15.5(3) . . . . ?
O1 C5 C6 C8 167.36(17) . . . . ?
C5 C6 C7 C4 9.1(2) . . . . ?
C8 C6 C7 C4 -161.75(17) . . . . ?
C5 C6 C7 C11 -172.87(16) . . . . ?
C8 C6 C7 C11 16.3(3) . . . . ?
N1 C4 C7 C6 106.80(17) . . . . ?
O1 C4 C7 C6 -11.14(18) . . . . ?
C3 C4 C7 C6 -129.77(18) . . . . ?
N1 C4 C7 C11 -71.1(2) . . . . ?
O1 C4 C7 C11 170.97(16) . . . . ?
C3 C4 C7 C11 52.3(3) . . . . ?
C7 C6 C8 C9 33.3(3) . . . . ?
C5 C6 C8 C9 -135.8(2) . . . . ?
C6 C8 C9 C10 -62.5(2) . . . . ?
C6 C8 C9 C13 63.3(2) . . . . ?
C13 C9 C10 C11 -73.6(3) . . . . ?
C8 C9 C10 C11 47.6(3) . . . . ?
C6 C7 C11 C12 -165.25(18) . . . . ?
C4 C7 C11 C12 12.4(3) . . . . ?
C6 C7 C11 C10 -33.7(2) . . . . ?
C4 C7 C11 C10 143.99(19) . . . . ?
C9 C10 C11 C7 0.2(3) . . . . ?
C9 C10 C11 C12 133.8(2) . . . . ?
C10 C9 C13 O3 175.7(2) . . . . ?
C8 C9 C13 O3 53.0(3) . . . . ?
C10 C9 C13 C14 -3.7(3) . . . . ?
C8 C9 C13 C14 -126.4(2) . . . . ?
O3 C13 C14 C15 -40.3(3) . . . . ?
C9 C13 C14 C15 139.1(2) . . . . ?
C13 C14 C15 C16 -59.3(3) . . . . ?
C14 C15 C16 N1 -61.4(3) . . . . ?
N2 C17 C18 C19 35.2(2) . . . . ?
C17 C18 C19 C20 -21.6(2) . . . . ?
C18 C19 C20 N2 -0.2(2) . . . . ?
C18 C19 C20 O4 118.46(18) . . . . ?
C18 C19 C20 C23 -125.5(2) . . . . ?
O5 C21 C22 C23 175.03(19) . . . . ?
O4 C21 C22 C23 -2.57(19) . . . . ?
O5 C21 C22 C24 -15.1(3) . . . . ?
O4 C21 C22 C24 167.28(17) . . . . ?
C21 C22 C23 C20 9.32(19) . . . . ?
C24 C22 C23 C20 -161.03(16) . . . . ?
C21 C22 C23 C27 -172.93(15) . . . . ?
C24 C22 C23 C27 16.7(3) . . . . ?
N2 C20 C23 C22 106.25(16) . . . . ?
O4 C20 C23 C22 -11.93(17) . . . . ?
C19 C20 C23 C22 -130.71(17) . . . . ?
N2 C20 C23 C27 -71.3(2) . . . . ?
O4 C20 C23 C27 170.54(16) . . . . ?
C19 C20 C23 C27 51.8(2) . . . . ?
C23 C22 C24 C25 32.2(2) . . . . ?
C21 C22 C24 C25 -136.30(18) . . . . ?
C22 C24 C25 C26 -62.1(2) . . . . ?
C22 C24 C25 C29 64.1(2) . . . . ?
C29 C25 C26 C27 -73.9(2) . . . . ?
C24 C25 C26 C27 48.0(2) . . . . ?
C22 C23 C27 C28 -164.41(17) . . . . ?
C20 C23 C27 C28 12.9(3) . . . . ?
C22 C23 C27 C26 -32.9(2) . . . . ?
C20 C23 C27 C26 144.35(18) . . . . ?
C25 C26 C27 C23 -0.9(2) . . . . ?
C25 C26 C27 C28 132.14(18) . . . . ?
C26 C25 C29 O6 -178.22(18) . . . . ?
C24 C25 C29 O6 58.7(2) . . . . ?
C26 C25 C29 C30 0.8(3) . . . . ?
C24 C25 C29 C30 -122.26(19) . . . . ?
O6 C29 C30 C31 -42.3(3) . . . . ?
C25 C29 C30 C31 138.69(18) . . . . ?
C29 C30 C31 C32 -64.0(2) . . . . ?
C30 C31 C32 N2 -59.1(2) . . . . ?
O1 C4 N1 C1 -90.98(18) . . . . ?
C7 C4 N1 C1 156.49(16) . . . . ?
C3 C4 N1 C1 24.7(2) . . . . ?
O1 C4 N1 C16 42.6(2) . . . . ?
C7 C4 N1 C16 -70.0(2) . . . . ?
C3 C4 N1 C16 158.20(17) . . . . ?
C2 C1 N1 C4 -36.6(2) . . . . ?
C2 C1 N1 C16 -171.23(18) . . . . ?
C15 C16 N1 C4 118.9(2) . . . . ?
C15 C16 N1 C1 -111.2(2) . . . . ?
O4 C20 N2 C17 -93.01(17) . . . . ?
C23 C20 N2 C17 154.52(16) . . . . ?
C19 C20 N2 C17 23.1(2) . . . . ?
O4 C20 N2 C32 42.0(2) . . . . ?
C23 C20 N2 C32 -70.45(19) . . . . ?
C19 C20 N2 C32 158.12(16) . . . . ?
C18 C17 N2 C20 -36.9(2) . . . . ?
C18 C17 N2 C32 -172.63(17) . . . . ?
C31 C32 N2 C20 119.05(18) . . . . ?
C31 C32 N2 C17 -109.6(2) . . . . ?
O2 C5 O1 C4 178.23(17) . . . . ?
C6 C5 O1 C4 -4.36(19) . . . . ?
N1 C4 O1 C5 -108.48(17) . . . . ?
C7 C4 O1 C5 9.15(17) . . . . ?
C3 C4 O1 C5 136.93(16) . . . . ?
O5 C21 O4 C20 176.86(16) . . . . ?
C22 C21 O4 C20 -5.31(18) . . . . ?
N2 C20 O4 C21 -107.34(16) . . . . ?
C23 C20 O4 C21 10.19(17) . . . . ?
C19 C20 O4 C21 137.81(16) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038

