# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_190322c
_database_code_depnum_ccdc_archive 'CCDC 1905335'
loop_
_audit_author_name
_audit_author_address
'shuzhong he'
;Guizhou University
China
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N2 O6 S'
_chemical_formula_weight         472.54

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.7885(9)
_cell_length_b                   8.7617(9)
_cell_length_c                   28.539(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.8440(10)
_cell_angle_gamma                90.00
_cell_volume                     2189.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3208
_cell_measurement_theta_min      2.433
_cell_measurement_theta_max      26.969

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_T_max  0.9496
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10584
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3868
_reflns_number_gt                2690
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0447P)²+1.3578P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3868
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2884(2) 0.5019(2) 0.36005(8) 0.0350(5) Uani 1 1 d . . .
N2 N 0.0371(3) 0.2713(3) 0.36658(9) 0.0448(6) Uani 1 1 d . . .
O1 O 0.5710(3) 1.1159(2) 0.44560(9) 0.0661(7) Uani 1 1 d . . .
O2 O 0.7958(2) 0.4608(3) 0.50440(8) 0.0623(6) Uani 1 1 d . . .
O3 O 0.3333(2) 0.3216(2) 0.29682(7) 0.0505(5) Uani 1 1 d . . .
O4 O 0.2868(2) 0.5909(2) 0.27756(7) 0.0516(5) Uani 1 1 d . . .
O5 O 0.1248(3) 0.1665(3) 0.36138(9) 0.0636(6) Uani 1 1 d . . .
O6 O 0.0000(3) 0.3134(3) 0.40435(8) 0.0751(7) Uani 1 1 d . . .
S1 S 0.25738(8) 0.46082(8) 0.30548(2) 0.0374(2) Uani 1 1 d . . .
C1 C 0.6426(3) 1.0010(3) 0.43802(10) 0.0434(7) Uani 1 1 d . . .
C2 C 0.5753(3) 0.8692(3) 0.40731(9) 0.0310(6) Uani 1 1 d . . .
C3 C 0.6771(3) 0.7256(3) 0.42001(9) 0.0301(6) Uani 1 1 d . . .
C4 C 0.7109(3) 0.7048(3) 0.47385(9) 0.0350(6) Uani 1 1 d . . .
H4 H 0.6150 0.6813 0.4875 0.042 Uiso 1 1 calc R . .
C5 C 0.7795(4) 0.8510(3) 0.49721(11) 0.0525(8) Uani 1 1 d . . .
H5A H 0.7119 0.8899 0.5196 0.063 Uiso 1 1 calc R . .
H5B H 0.8771 0.8277 0.5141 0.063 Uiso 1 1 calc R . .
C6 C 0.8013(3) 0.9717(3) 0.45972(11) 0.0494(8) Uani 1 1 d . . .
H6 H 0.8461 1.0649 0.4740 0.059 Uiso 1 1 calc R . .
C7 C 0.9040(3) 0.9043(4) 0.42463(12) 0.0576(9) Uani 1 1 d . . .
H7A H 0.9973 0.8668 0.4413 0.069 Uiso 1 1 calc R . .
H7B H 0.9312 0.9834 0.4031 0.069 Uiso 1 1 calc R . .
C8 C 0.8233(3) 0.7721(3) 0.39647(10) 0.0448(7) Uani 1 1 d . . .
H8 H 0.8920 0.6848 0.3942 0.054 Uiso 1 1 calc R . .
C9 C 0.7598(3) 0.8255(4) 0.34801(11) 0.0532(8) Uani 1 1 d . . .
H9A H 0.8324 0.8902 0.3337 0.064 Uiso 1 1 calc R . .
H9B H 0.7342 0.7394 0.3274 0.064 Uiso 1 1 calc R . .
C10 C 0.6186(3) 0.9138(3) 0.35790(10) 0.0408(7) Uani 1 1 d . . .
C11 C 0.5475(4) 1.0176(3) 0.33075(11) 0.0538(8) Uani 1 1 d . . .
H11A H 0.5839 1.0430 0.3021 0.065 Uiso 1 1 calc R . .
H11B H 0.4608 1.0656 0.3402 0.065 Uiso 1 1 calc R . .
C12 C 0.8199(3) 0.5754(4) 0.48417(11) 0.0475(8) Uani 1 1 d . . .
H12 H 0.9166 0.5860 0.4736 0.057 Uiso 1 1 calc R . .
C13 C 0.4011(3) 0.8609(3) 0.41109(9) 0.0348(6) Uani 1 1 d . . .
H13A H 0.3845 0.8024 0.4391 0.042 Uiso 1 1 calc R . .
H13B H 0.3655 0.9638 0.4163 0.042 Uiso 1 1 calc R . .
C14 C 0.2979(3) 0.7925(3) 0.36996(10) 0.0386(7) Uani 1 1 d . . .
H14A H 0.2209 0.8683 0.3605 0.046 Uiso 1 1 calc R . .
H14B H 0.3602 0.7795 0.3438 0.046 Uiso 1 1 calc R . .
C15 C 0.2148(3) 0.6414(3) 0.37643(10) 0.0361(6) Uani 1 1 d . . .
H15A H 0.2016 0.6293 0.4096 0.043 Uiso 1 1 calc R . .
H15B H 0.1138 0.6488 0.3601 0.043 Uiso 1 1 calc R . .
C16 C 0.3785(3) 0.4037(3) 0.39405(10) 0.0403(7) Uani 1 1 d . . .
H16A H 0.4324 0.3275 0.3772 0.048 Uiso 1 1 calc R . .
H16B H 0.3103 0.3509 0.4136 0.048 Uiso 1 1 calc R . .
C17 C 0.4919(3) 0.4960(3) 0.42481(9) 0.0363(6) Uani 1 1 d . . .
H17A H 0.5448 0.4287 0.4478 0.044 Uiso 1 1 calc R . .
H17B H 0.4370 0.5710 0.4418 0.044 Uiso 1 1 calc R . .
C18 C 0.6094(3) 0.5779(3) 0.39765(10) 0.0338(6) Uani 1 1 d . . .
H18A H 0.5622 0.6023 0.3666 0.041 Uiso 1 1 calc R . .
H18B H 0.6927 0.5077 0.3936 0.041 Uiso 1 1 calc R . .
C19 C 0.0555(3) 0.4337(3) 0.29589(9) 0.0361(6) Uani 1 1 d . . .
C20 C -0.0318(3) 0.3490(3) 0.32450(10) 0.0355(6) Uani 1 1 d . . .
C21 C -0.1875(3) 0.3343(3) 0.31603(11) 0.0478(8) Uani 1 1 d . . .
H21 H -0.2430 0.2774 0.3362 0.057 Uiso 1 1 calc R . .
C22 C -0.2599(4) 0.4051(4) 0.27734(12) 0.0574(9) Uani 1 1 d . . .
H22 H -0.3648 0.3943 0.2707 0.069 Uiso 1 1 calc R . .
C23 C -0.1774(4) 0.4911(4) 0.24867(12) 0.0607(9) Uani 1 1 d . . .
H23 H -0.2269 0.5402 0.2228 0.073 Uiso 1 1 calc R . .
C24 C -0.0216(4) 0.5062(3) 0.25767(11) 0.0506(8) Uani 1 1 d . . .
H24 H 0.0326 0.5657 0.2379 0.061 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.476(3) . ?
N1 C15 1.477(3) . ?
N1 S1 1.599(2) . ?
N2 O6 1.210(3) . ?
N2 O5 1.215(3) . ?
N2 C20 1.466(4) . ?
O1 C1 1.217(3) . ?
O2 C12 1.186(3) . ?
O3 S1 1.4223(19) . ?
O4 S1 1.4263(19) . ?
S1 C19 1.788(3) . ?
C1 C6 1.499(4) . ?
C1 C2 1.537(4) . ?
C2 C10 1.542(4) . ?
C2 C13 1.545(3) . ?
C2 C3 1.568(3) . ?
C3 C18 1.540(3) . ?
C3 C4 1.551(4) . ?
C3 C8 1.554(3) . ?
C4 C12 1.497(4) . ?
C4 C5 1.544(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.528(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.523(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.548(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.521(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.509(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.318(4) . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.543(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.530(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.507(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.522(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.383(4) . ?
C19 C24 1.388(4) . ?
C20 C21 1.376(4) . ?
C21 C22 1.375(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C15 119.9(2) . . ?
C16 N1 S1 123.16(18) . . ?
C15 N1 S1 116.81(17) . . ?
O6 N2 O5 124.1(3) . . ?
O6 N2 C20 117.6(3) . . ?
O5 N2 C20 118.2(3) . . ?
O3 S1 O4 118.58(12) . . ?
O3 S1 N1 108.54(12) . . ?
O4 S1 N1 109.90(12) . . ?
O3 S1 C19 109.48(12) . . ?
O4 S1 C19 104.18(13) . . ?
N1 S1 C19 105.33(12) . . ?
O1 C1 C6 123.0(3) . . ?
O1 C1 C2 122.9(3) . . ?
C6 C1 C2 114.0(2) . . ?
C1 C2 C10 102.6(2) . . ?
C1 C2 C13 109.4(2) . . ?
C10 C2 C13 113.5(2) . . ?
C1 C2 C3 106.6(2) . . ?
C10 C2 C3 103.6(2) . . ?
C13 C2 C3 119.7(2) . . ?
C18 C3 C4 110.3(2) . . ?
C18 C3 C8 110.2(2) . . ?
C4 C3 C8 111.3(2) . . ?
C18 C3 C2 112.7(2) . . ?
C4 C3 C2 112.4(2) . . ?
C8 C3 C2 99.6(2) . . ?
C12 C4 C5 108.9(2) . . ?
C12 C4 C3 110.5(2) . . ?
C5 C4 C3 111.4(2) . . ?
C12 C4 H4 108.7 . . ?
C5 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
C6 C5 C4 109.9(2) . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C1 C6 C7 112.1(3) . . ?
C1 C6 C5 103.9(2) . . ?
C7 C6 C5 108.0(3) . . ?
C1 C6 H6 110.9 . . ?
C7 C6 H6 110.9 . . ?
C5 C6 H6 110.9 . . ?
C6 C7 C8 111.1(2) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 111.0(3) . . ?
C9 C8 C3 102.7(2) . . ?
C7 C8 C3 109.3(2) . . ?
C9 C8 H8 111.1 . . ?
C7 C8 H8 111.1 . . ?
C3 C8 H8 111.1 . . ?
C10 C9 C8 103.4(2) . . ?
C10 C9 H9A 111.1 . . ?
C8 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C9 126.9(3) . . ?
C11 C10 C2 124.8(3) . . ?
C9 C10 C2 108.1(2) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
O2 C12 C4 126.8(3) . . ?
O2 C12 H12 116.6 . . ?
C4 C12 H12 116.6 . . ?
C14 C13 C2 119.2(2) . . ?
C14 C13 H13A 107.5 . . ?
C2 C13 H13A 107.5 . . ?
C14 C13 H13B 107.5 . . ?
C2 C13 H13B 107.5 . . ?
H13A C13 H13B 107.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14A 107.3 . . ?
C13 C14 H14A 107.3 . . ?
C15 C14 H14B 107.3 . . ?
C13 C14 H14B 107.3 . . ?
H14A C14 H14B 106.9 . . ?
N1 C15 C14 116.9(2) . . ?
N1 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
N1 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
N1 C16 C17 111.2(2) . . ?
N1 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 113.6(2) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C3 116.1(2) . . ?
C17 C18 H18A 108.3 . . ?
C3 C18 H18A 108.3 . . ?
C17 C18 H18B 108.3 . . ?
C3 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C24 116.8(3) . . ?
C20 C19 S1 125.0(2) . . ?
C24 C19 S1 118.1(2) . . ?
C21 C20 C19 122.7(3) . . ?
C21 C20 N2 115.9(2) . . ?
C19 C20 N2 121.4(2) . . ?
C22 C21 C20 119.0(3) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 120.9(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?

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
C16 N1 S1 O3 -1.6(2) . . . . ?
C15 N1 S1 O3 -178.26(17) . . . . ?
C16 N1 S1 O4 -132.7(2) . . . . ?
C15 N1 S1 O4 50.6(2) . . . . ?
C16 N1 S1 C19 115.6(2) . . . . ?
C15 N1 S1 C19 -61.1(2) . . . . ?
O1 C1 C2 C10 90.4(3) . . . . ?
C6 C1 C2 C10 -92.5(3) . . . . ?
O1 C1 C2 C13 -30.4(4) . . . . ?
C6 C1 C2 C13 146.7(2) . . . . ?
O1 C1 C2 C3 -161.1(3) . . . . ?
C6 C1 C2 C3 16.0(3) . . . . ?
C1 C2 C3 C18 171.1(2) . . . . ?
C10 C2 C3 C18 -81.0(2) . . . . ?
C13 C2 C3 C18 46.5(3) . . . . ?
C1 C2 C3 C4 45.8(3) . . . . ?
C10 C2 C3 C4 153.6(2) . . . . ?
C13 C2 C3 C4 -78.8(3) . . . . ?
C1 C2 C3 C8 -72.1(2) . . . . ?
C10 C2 C3 C8 35.7(2) . . . . ?
C13 C2 C3 C8 163.3(2) . . . . ?
C18 C3 C4 C12 58.6(3) . . . . ?
C8 C3 C4 C12 -64.0(3) . . . . ?
C2 C3 C4 C12 -174.7(2) . . . . ?
C18 C3 C4 C5 179.8(2) . . . . ?
C8 C3 C4 C5 57.1(3) . . . . ?
C2 C3 C4 C5 -53.6(3) . . . . ?
C12 C4 C5 C6 119.4(3) . . . . ?
C3 C4 C5 C6 -2.7(3) . . . . ?
O1 C1 C6 C7 -137.9(3) . . . . ?
C2 C1 C6 C7 45.0(3) . . . . ?
O1 C1 C6 C5 105.7(3) . . . . ?
C2 C1 C6 C5 -71.4(3) . . . . ?
C4 C5 C6 C1 61.6(3) . . . . ?
C4 C5 C6 C7 -57.7(3) . . . . ?
C1 C6 C7 C8 -46.8(4) . . . . ?
C5 C6 C7 C8 67.1(3) . . . . ?
C6 C7 C8 C9 100.4(3) . . . . ?
C6 C7 C8 C3 -12.2(4) . . . . ?
C18 C3 C8 C9 71.3(3) . . . . ?
C4 C3 C8 C9 -166.1(2) . . . . ?
C2 C3 C8 C9 -47.3(3) . . . . ?
C18 C3 C8 C7 -170.7(2) . . . . ?
C4 C3 C8 C7 -48.1(3) . . . . ?
C2 C3 C8 C7 70.7(3) . . . . ?
C7 C8 C9 C10 -76.2(3) . . . . ?
C3 C8 C9 C10 40.6(3) . . . . ?
C8 C9 C10 C11 159.2(3) . . . . ?
C8 C9 C10 C2 -17.4(3) . . . . ?
C1 C2 C10 C11 -78.0(3) . . . . ?
C13 C2 C10 C11 39.9(4) . . . . ?
C3 C2 C10 C11 171.2(3) . . . . ?
C1 C2 C10 C9 98.7(3) . . . . ?
C13 C2 C10 C9 -143.4(2) . . . . ?
C3 C2 C10 C9 -12.1(3) . . . . ?
C5 C4 C12 O2 119.9(3) . . . . ?
C3 C4 C12 O2 -117.4(3) . . . . ?
C1 C2 C13 C14 153.5(2) . . . . ?
C10 C2 C13 C14 39.6(3) . . . . ?
C3 C2 C13 C14 -83.2(3) . . . . ?
C2 C13 C14 C15 112.6(3) . . . . ?
C16 N1 C15 C14 99.2(3) . . . . ?
S1 N1 C15 C14 -84.0(3) . . . . ?
C13 C14 C15 N1 -96.8(3) . . . . ?
C15 N1 C16 C17 -49.6(3) . . . . ?
S1 N1 C16 C17 133.8(2) . . . . ?
N1 C16 C17 C18 -61.7(3) . . . . ?
C16 C17 C18 C3 152.4(2) . . . . ?
C4 C3 C18 C17 41.5(3) . . . . ?
C8 C3 C18 C17 164.7(2) . . . . ?
C2 C3 C18 C17 -85.0(3) . . . . ?
O3 S1 C19 C20 70.5(3) . . . . ?
O4 S1 C19 C20 -161.7(2) . . . . ?
N1 S1 C19 C20 -46.0(3) . . . . ?
O3 S1 C19 C24 -111.4(2) . . . . ?
O4 S1 C19 C24 16.4(3) . . . . ?
N1 S1 C19 C24 132.0(2) . . . . ?
C24 C19 C20 C21 0.6(4) . . . . ?
S1 C19 C20 C21 178.6(2) . . . . ?
C24 C19 C20 N2 -178.2(2) . . . . ?
S1 C19 C20 N2 -0.2(4) . . . . ?
O6 N2 C20 C21 -63.4(3) . . . . ?
O5 N2 C20 C21 114.8(3) . . . . ?
O6 N2 C20 C19 115.5(3) . . . . ?
O5 N2 C20 C19 -66.3(3) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
N2 C20 C21 C22 179.6(3) . . . . ?
C20 C21 C22 C23 -1.5(5) . . . . ?
C21 C22 C23 C24 1.0(5) . . . . ?
C22 C23 C24 C19 0.3(5) . . . . ?
C20 C19 C24 C23 -1.1(4) . . . . ?
S1 C19 C24 C23 -179.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_exp_6289
_database_code_depnum_ccdc_archive 'CCDC 1974776'
loop_
_audit_author_name
_audit_author_address
'Dr. Shuzhong He'
;Guizhou University
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-18
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H15 N O3'
_chemical_formula_sum            'C12 H15 N O3'
_chemical_formula_weight         221.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.0155(6)
_cell_length_b                   11.8959(9)
_cell_length_c                   12.3411(8)
_cell_angle_alpha                77.623(6)
_cell_angle_beta                 81.660(6)
_cell_angle_gamma                71.099(7)
_cell_volume                     1083.77(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4054
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.9350
_cell_measurement_theta_min      4.1070
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14444
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.30
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.8735
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    2.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   57.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000 -150.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   57.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   77.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
  5 omega  -47.00   39.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -77.0000  -60.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   12.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  7 omega   33.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772 -178.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -25.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000  120.0000 83

#__ type_ start__ end____ width___ exp.time_
  9 omega  -25.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000 -150.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0342010000
_diffrn_orient_matrix_UB_12      -0.0251449000
_diffrn_orient_matrix_UB_13      0.0525104000
_diffrn_orient_matrix_UB_21      0.0758042000
_diffrn_orient_matrix_UB_22      -0.0516369000
_diffrn_orient_matrix_UB_23      0.0022729000
_diffrn_orient_matrix_UB_31      0.0435515000
_diffrn_orient_matrix_UB_32      0.0283585000
_diffrn_orient_matrix_UB_33      0.0268833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3504
_reflns_number_total             4254
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0423P)²+0.3524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1009
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.27013(14) 0.43044(9) 0.41530(9) 0.0255(3) Uani 1 1 d . . .
O2 O 0.17640(16) 0.70990(10) 0.56492(9) 0.0324(3) Uani 1 1 d . . .
O3 O 0.16849(16) 0.89650(10) 0.51343(9) 0.0314(3) Uani 1 1 d . . .
N1 N 0.19758(17) 0.79470(12) 0.49436(10) 0.0217(3) Uani 1 1 d . . .
C1 C 0.2605(2) 0.77312(14) 0.37680(12) 0.0200(3) Uani 1 1 d . . .
H1 H 0.2898 0.8447 0.3338 0.024 Uiso 1 1 calc R . .
C2 C 0.4286(2) 0.66499(14) 0.37870(13) 0.0240(3) Uani 1 1 d . . .
H2A H 0.4483 0.6240 0.4548 0.029 Uiso 1 1 calc R . .
H2B H 0.5299 0.6923 0.3474 0.029 Uiso 1 1 calc R . .
C3 C 0.4063(2) 0.57794(14) 0.30997(12) 0.0218(3) Uani 1 1 d . . .
H3 H 0.5148 0.5103 0.3049 0.026 Uiso 1 1 calc R . .
C4 C 0.2542(2) 0.53400(13) 0.36903(11) 0.0190(3) Uani 1 1 d . . .
C5 C 0.07672(19) 0.63274(13) 0.36505(12) 0.0179(3) Uani 1 1 d . . .
H5 H 0.0047 0.6294 0.4363 0.021 Uiso 1 1 calc R . .
C6 C 0.11001(19) 0.75684(13) 0.32327(11) 0.0182(3) Uani 1 1 d . . .
C7 C 0.1733(2) 0.74551(14) 0.19948(12) 0.0210(3) Uani 1 1 d . . .
H7 H 0.1741 0.8238 0.1542 0.025 Uiso 1 1 calc R . .
C8 C 0.0333(2) 0.70005(14) 0.16544(12) 0.0233(3) Uani 1 1 d . . .
H8A H -0.0693 0.7669 0.1417 0.028 Uiso 1 1 calc R . .
H8B H 0.0812 0.6547 0.1055 0.028 Uiso 1 1 calc R . .
C9 C -0.01476(19) 0.61974(13) 0.27006(12) 0.0196(3) Uani 1 1 d . . .
C10 C -0.1165(2) 0.54963(14) 0.27999(14) 0.0259(4) Uani 1 1 d . . .
H10A H -0.1674 0.5461 0.2182 0.031 Uiso 1 1 calc R . .
H10B H -0.1372 0.5038 0.3488 0.031 Uiso 1 1 calc R . .
C11 C 0.3591(2) 0.65128(14) 0.19403(12) 0.0233(3) Uani 1 1 d . . .
H11A H 0.3615 0.5970 0.1449 0.028 Uiso 1 1 calc R . .
H11B H 0.4466 0.6924 0.1634 0.028 Uiso 1 1 calc R . .
C12 C -0.0587(2) 0.86164(14) 0.33280(13) 0.0232(3) Uani 1 1 d . . .
H12A H -0.1493 0.8511 0.2965 0.035 Uiso 1 1 calc R . .
H12B H -0.0359 0.9361 0.2980 0.035 Uiso 1 1 calc R . .
H12C H -0.0971 0.8637 0.4099 0.035 Uiso 1 1 calc R . .
O4 O 0.47379(15) 1.07060(10) 0.80669(10) 0.0335(3) Uani 1 1 d . . .
O5 O 0.29978(14) 0.78828(10) 0.93677(9) 0.0299(3) Uani 1 1 d . . .
O6 O 0.35485(15) 0.60775(10) 0.90408(10) 0.0334(3) Uani 1 1 d . . .
N2 N 0.37955(16) 0.70683(12) 0.88516(10) 0.0225(3) Uani 1 1 d . . .
C13 C 0.51749(19) 0.72952(14) 0.79389(12) 0.0209(3) Uani 1 1 d . . .
H13 H 0.5620 0.6594 0.7564 0.025 Uiso 1 1 calc R . .
C14 C 0.4331(2) 0.84056(16) 0.70863(14) 0.0305(4) Uani 1 1 d . . .
H14A H 0.3153 0.8823 0.7376 0.037 Uiso 1 1 calc R . .
H14B H 0.4231 0.8158 0.6405 0.037 Uiso 1 1 calc R . .
C15 C 0.5485(2) 0.92543(15) 0.68423(13) 0.0264(4) Uani 1 1 d . . .
H15 H 0.5030 0.9940 0.6251 0.032 Uiso 1 1 calc R . .
C16 C 0.5430(2) 0.96756(14) 0.79198(13) 0.0231(3) Uani 1 1 d . . .
C17 C 0.63450(19) 0.86581(13) 0.88201(12) 0.0184(3) Uani 1 1 d . . .
H17 H 0.5682 0.8684 0.9552 0.022 Uiso 1 1 calc R . .
C18 C 0.67299(19) 0.74329(13) 0.84436(12) 0.0179(3) Uani 1 1 d . . .
C19 C 0.81966(19) 0.75440(14) 0.74880(12) 0.0213(3) Uani 1 1 d . . .
H19 H 0.8813 0.6763 0.7260 0.026 Uiso 1 1 calc R . .
C20 C 0.9429(2) 0.79662(15) 0.80390(14) 0.0251(4) Uani 1 1 d . . .
H20A H 1.0276 0.7284 0.8448 0.030 Uiso 1 1 calc R . .
H20B H 1.0067 0.8424 0.7487 0.030 Uiso 1 1 calc R . .
C21 C 0.8197(2) 0.87537(13) 0.88178(12) 0.0205(3) Uani 1 1 d . . .
C22 C 0.8610(2) 0.94129(14) 0.94073(13) 0.0254(4) Uani 1 1 d . . .
H22A H 0.9772 0.9425 0.9368 0.031 Uiso 1 1 calc R . .
H22B H 0.7741 0.9866 0.9862 0.031 Uiso 1 1 calc R . .
C23 C 0.7375(2) 0.85025(15) 0.65001(13) 0.0272(4) Uani 1 1 d . . .
H23A H 0.8104 0.9033 0.6235 0.033 Uiso 1 1 calc R . .
H23B H 0.7343 0.8107 0.5896 0.033 Uiso 1 1 calc R . .
C24 C 0.7409(2) 0.63700(14) 0.93747(13) 0.0235(3) Uani 1 1 d . . .
H24A H 0.8380 0.6471 0.9675 0.035 Uiso 1 1 calc R . .
H24B H 0.7799 0.5633 0.9083 0.035 Uiso 1 1 calc R . .
H24C H 0.6475 0.6338 0.9952 0.035 Uiso 1 1 calc R . .


_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 C4 1.2156(18) . ?
O2 N1 1.2232(16) . ?
O3 N1 1.2246(16) . ?
N1 C1 1.5129(19) . ?
C1 H1 0.9800 . ?
C1 C2 1.531(2) . ?
C1 C6 1.538(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.537(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.511(2) . ?
C3 C11 1.536(2) . ?
C4 C5 1.523(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.551(2) . ?
C5 C9 1.529(2) . ?
C6 C7 1.558(2) . ?
C6 C12 1.524(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.535(2) . ?
C7 C11 1.549(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.514(2) . ?
C9 C10 1.320(2) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O4 C16 1.2120(19) . ?
O5 N2 1.2241(16) . ?
O6 N2 1.2259(16) . ?
N2 C13 1.5053(19) . ?
C13 H13 0.9800 . ?
C13 C14 1.530(2) . ?
C13 C18 1.539(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.536(2) . ?
C15 H15 0.9800 . ?
C15 C16 1.509(2) . ?
C15 C23 1.540(2) . ?
C16 C17 1.524(2) . ?
C17 H17 0.9800 . ?
C17 C18 1.5468(19) . ?
C17 C21 1.524(2) . ?
C18 C19 1.556(2) . ?
C18 C24 1.526(2) . ?
C19 H19 0.9800 . ?
C19 C20 1.534(2) . ?
C19 C23 1.540(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.513(2) . ?
C21 C22 1.318(2) . ?
C22 H22A 0.9300 . ?
C22 H22B 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
O2 N1 O3 123.54(13) . . ?
O2 N1 C1 118.24(12) . . ?
O3 N1 C1 118.21(12) . . ?
N1 C1 H1 108.3 . . ?
N1 C1 C2 109.43(12) . . ?
N1 C1 C6 109.32(11) . . ?
C2 C1 H1 108.3 . . ?
C2 C1 C6 113.14(12) . . ?
C6 C1 H1 108.3 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C1 C2 C3 108.74(12) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C2 C3 H3 111.0 . . ?
C4 C3 C2 106.11(12) . . ?
C4 C3 H3 111.0 . . ?
C4 C3 C11 110.38(12) . . ?
C11 C3 C2 107.16(12) . . ?
C11 C3 H3 111.0 . . ?
O1 C4 C3 123.93(14) . . ?
O1 C4 C5 122.80(13) . . ?
C3 C4 C5 113.27(12) . . ?
C4 C5 H5 112.7 . . ?
C4 C5 C6 108.78(12) . . ?
C4 C5 C9 106.59(11) . . ?
C6 C5 H5 112.7 . . ?
C9 C5 H5 112.7 . . ?
C9 C5 C6 102.87(11) . . ?
C1 C6 C5 114.35(12) . . ?
C1 C6 C7 108.12(12) . . ?
C5 C6 C7 99.27(11) . . ?
C12 C6 C1 110.93(12) . . ?
C12 C6 C5 112.00(12) . . ?
C12 C6 C7 111.57(12) . . ?
C6 C7 H7 111.2 . . ?
C8 C7 C6 102.37(11) . . ?
C8 C7 H7 111.2 . . ?
C8 C7 C11 111.23(12) . . ?
C11 C7 C6 109.20(12) . . ?
C11 C7 H7 111.2 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 C7 104.21(11) . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C8 C9 C5 107.91(12) . . ?
C10 C9 C5 124.86(14) . . ?
C10 C9 C8 127.23(14) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C3 C11 C7 111.21(12) . . ?
C3 C11 H11A 109.4 . . ?
C3 C11 H11B 109.4 . . ?
C7 C11 H11A 109.4 . . ?
C7 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 N2 O6 123.91(13) . . ?
O5 N2 C13 117.90(12) . . ?
O6 N2 C13 118.18(13) . . ?
N2 C13 H13 108.4 . . ?
N2 C13 C14 109.53(13) . . ?
N2 C13 C18 109.70(11) . . ?
C14 C13 H13 108.4 . . ?
C14 C13 C18 112.37(12) . . ?
C18 C13 H13 108.4 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C13 C14 C15 109.26(13) . . ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C14 C15 H15 111.0 . . ?
C14 C15 C23 107.11(14) . . ?
C16 C15 C14 105.94(13) . . ?
C16 C15 H15 111.0 . . ?
C16 C15 C23 110.75(13) . . ?
C23 C15 H15 111.0 . . ?
O4 C16 C15 124.40(15) . . ?
O4 C16 C17 122.99(14) . . ?
C15 C16 C17 112.61(13) . . ?
C16 C17 H17 112.7 . . ?
C16 C17 C18 109.34(12) . . ?
C16 C17 C21 106.48(12) . . ?
C18 C17 H17 112.7 . . ?
C21 C17 H17 112.7 . . ?
C21 C17 C18 102.41(11) . . ?
C13 C18 C17 114.38(12) . . ?
C13 C18 C19 107.93(11) . . ?
C17 C18 C19 99.55(11) . . ?
C24 C18 C13 110.79(12) . . ?
C24 C18 C17 111.77(12) . . ?
C24 C18 C19 111.90(12) . . ?
C18 C19 H19 111.2 . . ?
C20 C19 C18 102.06(12) . . ?
C20 C19 H19 111.2 . . ?
C20 C19 C23 111.20(13) . . ?
C23 C19 C18 109.55(12) . . ?
C23 C19 H19 111.2 . . ?
C19 C20 H20A 110.9 . . ?
C19 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
C21 C20 C19 104.14(12) . . ?
C21 C20 H20A 110.9 . . ?
C21 C20 H20B 110.9 . . ?
C20 C21 C17 108.15(12) . . ?
C22 C21 C17 124.66(14) . . ?
C22 C21 C20 127.19(14) . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?
C15 C23 C19 110.99(12) . . ?
C15 C23 H23A 109.4 . . ?
C15 C23 H23B 109.4 . . ?
C19 C23 H23A 109.4 . . ?
C19 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C4 C5 C6 167.75(13) . . . . ?
O1 C4 C5 C9 -81.96(16) . . . . ?
O2 N1 C1 C2 -52.87(17) . . . . ?
O2 N1 C1 C6 71.55(16) . . . . ?
O3 N1 C1 C2 128.02(14) . . . . ?
O3 N1 C1 C6 -107.56(14) . . . . ?
N1 C1 C2 C3 130.44(13) . . . . ?
N1 C1 C6 C5 -75.11(15) . . . . ?
N1 C1 C6 C7 175.37(11) . . . . ?
N1 C1 C6 C12 52.73(15) . . . . ?
C1 C2 C3 C4 -63.33(15) . . . . ?
C1 C2 C3 C11 54.61(15) . . . . ?
C1 C6 C7 C8 166.97(11) . . . . ?
C1 C6 C7 C11 49.00(15) . . . . ?
C2 C1 C6 C5 47.12(16) . . . . ?
C2 C1 C6 C7 -62.41(15) . . . . ?
C2 C1 C6 C12 174.95(12) . . . . ?
C2 C3 C4 O1 -112.67(16) . . . . ?
C2 C3 C4 C5 67.39(15) . . . . ?
C2 C3 C11 C7 -67.59(15) . . . . ?
C3 C4 C5 C6 -12.31(16) . . . . ?
C3 C4 C5 C9 97.98(14) . . . . ?
C4 C3 C11 C7 47.53(16) . . . . ?
C4 C5 C6 C1 -44.43(16) . . . . ?
C4 C5 C6 C7 70.39(13) . . . . ?
C4 C5 C6 C12 -171.72(11) . . . . ?
C4 C5 C9 C8 -91.92(13) . . . . ?
C4 C5 C9 C10 87.83(17) . . . . ?
C5 C6 C7 C8 47.43(13) . . . . ?
C5 C6 C7 C11 -70.54(13) . . . . ?
C6 C1 C2 C3 8.28(17) . . . . ?
C6 C5 C9 C8 22.45(15) . . . . ?
C6 C5 C9 C10 -157.80(15) . . . . ?
C6 C7 C8 C9 -34.23(14) . . . . ?
C6 C7 C11 C3 12.77(17) . . . . ?
C7 C8 C9 C5 7.36(15) . . . . ?
C7 C8 C9 C10 -172.38(15) . . . . ?
C8 C7 C11 C3 -99.48(14) . . . . ?
C9 C5 C6 C1 -157.21(12) . . . . ?
C9 C5 C6 C7 -42.39(13) . . . . ?
C9 C5 C6 C12 75.50(14) . . . . ?
C11 C3 C4 O1 131.54(15) . . . . ?
C11 C3 C4 C5 -48.39(16) . . . . ?
C11 C7 C8 C9 82.28(14) . . . . ?
C12 C6 C7 C8 -70.79(14) . . . . ?
C12 C6 C7 C11 171.25(12) . . . . ?
O4 C16 C17 C18 168.26(14) . . . . ?
O4 C16 C17 C21 -81.78(18) . . . . ?
O5 N2 C13 C14 -57.15(17) . . . . ?
O5 N2 C13 C18 66.62(17) . . . . ?
O6 N2 C13 C14 123.49(14) . . . . ?
O6 N2 C13 C18 -112.74(14) . . . . ?
N2 C13 C14 C15 131.43(14) . . . . ?
N2 C13 C18 C17 -75.50(15) . . . . ?
N2 C13 C18 C19 174.75(12) . . . . ?
N2 C13 C18 C24 51.91(16) . . . . ?
C13 C14 C15 C16 -64.39(17) . . . . ?
C13 C14 C15 C23 53.87(17) . . . . ?
C13 C18 C19 C20 167.32(12) . . . . ?
C13 C18 C19 C23 49.39(15) . . . . ?
C14 C13 C18 C17 46.60(17) . . . . ?
C14 C13 C18 C19 -63.16(16) . . . . ?
C14 C13 C18 C24 174.01(13) . . . . ?
C14 C15 C16 O4 -112.92(17) . . . . ?
C14 C15 C16 C17 66.96(16) . . . . ?
C14 C15 C23 C19 -67.37(16) . . . . ?
C15 C16 C17 C18 -11.62(17) . . . . ?
C15 C16 C17 C21 98.33(14) . . . . ?
C16 C15 C23 C19 47.72(17) . . . . ?
C16 C17 C18 C13 -45.10(16) . . . . ?
C16 C17 C18 C19 69.66(14) . . . . ?
C16 C17 C18 C24 -172.01(12) . . . . ?
C16 C17 C21 C20 -91.64(14) . . . . ?
C16 C17 C21 C22 88.67(18) . . . . ?
C17 C18 C19 C20 47.70(14) . . . . ?
C17 C18 C19 C23 -70.23(14) . . . . ?
C18 C13 C14 C15 9.24(18) . . . . ?
C18 C17 C21 C20 23.12(15) . . . . ?
C18 C17 C21 C22 -156.57(15) . . . . ?
C18 C19 C20 C21 -33.87(15) . . . . ?
C18 C19 C23 C15 12.91(17) . . . . ?
C19 C20 C21 C17 6.77(16) . . . . ?
C19 C20 C21 C22 -173.54(15) . . . . ?
C20 C19 C23 C15 -99.16(15) . . . . ?
C21 C17 C18 C13 -157.75(12) . . . . ?
C21 C17 C18 C19 -42.99(13) . . . . ?
C21 C17 C18 C24 75.34(14) . . . . ?
C23 C15 C16 O4 131.26(16) . . . . ?
C23 C15 C16 C17 -48.85(17) . . . . ?
C23 C19 C20 C21 82.87(15) . . . . ?
C24 C18 C19 C20 -70.52(15) . . . . ?
C24 C18 C19 C23 171.55(12) . . . . ?
