# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_R20180905D1
_database_code_depnum_ccdc_archive 'CCDC 1947437'
loop_
_audit_author_name
_audit_author_address
'Jiayong Zhang'
;nankai university
China
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 O5'
_chemical_formula_weight         318.35

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   31.452(6)
_cell_length_b                   5.5892(11)
_cell_length_c                   19.232(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.16(3)
_cell_angle_gamma                90
_cell_volume                     3380.8(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3260
_cell_measurement_theta_min      2.1179
_cell_measurement_theta_max      27.8306

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7288
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19193
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.590
_diffrn_reflns_theta_max         27.837
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4017
_reflns_number_gt                2862
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+0.7523P] 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_number_reflns         4017
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.05532(5) 1.2238(2) 0.15258(7) 0.0321(4) Uani 1 1 d . . . . .
O2 O 0.01624(5) 0.7810(2) 0.36429(7) 0.0315(4) Uani 1 1 d . . . . .
O3 O 0.05071(5) 1.0884(3) 0.41546(7) 0.0363(4) Uani 1 1 d . . . . .
O4 O 0.12885(5) 0.8203(2) 0.35522(7) 0.0315(4) Uani 1 1 d . . . . .
O5 O 0.15115(5) 1.2013(3) 0.36219(9) 0.0453(4) Uani 1 1 d . . . . .
C1 C 0.09063(6) 1.0759(3) 0.14752(10) 0.0270(4) Uani 1 1 d . . . . .
C2 C 0.10149(7) 0.9890(4) 0.08230(10) 0.0335(5) Uani 1 1 d . . . . .
H2 H 0.085012 1.031273 0.042685 0.040 Uiso 1 1 calc R U . . .
C3 C 0.13653(7) 0.8401(4) 0.07527(10) 0.0313(5) Uani 1 1 d . . . . .
H3 H 0.143323 0.778273 0.030654 0.038 Uiso 1 1 calc R U . . .
C4 C 0.16215(6) 0.7785(3) 0.13227(10) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.14969(6) 0.8634(3) 0.19727(10) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.166160 0.821568 0.236932 0.029 Uiso 1 1 calc R U . . .
C6 C 0.11386(6) 1.0076(3) 0.20613(10) 0.0237(4) Uani 1 1 d . . . . .
C7 C 0.09868(6) 1.0874(3) 0.27630(10) 0.0236(4) Uani 1 1 d . . . . .
C8 C 0.05107(6) 1.0469(3) 0.29132(10) 0.0241(4) Uani 1 1 d . . . . .
H8 H 0.033928 0.970786 0.253459 0.029 Uiso 1 1 calc R U . . .
C9 C 0.06845(6) 1.2934(3) 0.27672(11) 0.0284(5) Uani 1 1 d . . . . .
H9 H 0.070390 1.406080 0.316998 0.034 Uiso 1 1 calc R U . . .
C10 C 0.05904(7) 1.4018(4) 0.20642(11) 0.0341(5) Uani 1 1 d . . . . .
H10A H 0.032175 1.493707 0.209056 0.041 Uiso 1 1 calc R U . . .
H10B H 0.082070 1.514826 0.194167 0.041 Uiso 1 1 calc R U . . .
C11 C 0.20356(6) 0.6356(3) 0.12411(10) 0.0263(4) Uani 1 1 d . . . . .
C12 C 0.20108(9) 0.4612(5) 0.06311(13) 0.0540(7) Uani 1 1 d . . . . .
H12A H 0.197510 0.550829 0.019702 0.081 Uiso 1 1 calc R U . . .
H12B H 0.176805 0.353570 0.069518 0.081 Uiso 1 1 calc R U . . .
H12C H 0.227348 0.367130 0.060986 0.081 Uiso 1 1 calc R U . . .
C13 C 0.23959(8) 0.8126(4) 0.11109(17) 0.0567(8) Uani 1 1 d . . . . .
H13A H 0.233717 0.903063 0.068484 0.085 Uiso 1 1 calc R U . . .
H13B H 0.266413 0.725173 0.105952 0.085 Uiso 1 1 calc R U . . .
H13C H 0.241803 0.923220 0.150465 0.085 Uiso 1 1 calc R U . . .
C14 C 0.21425(9) 0.4901(5) 0.18922(13) 0.0554(8) Uani 1 1 d . . . . .
H14A H 0.239381 0.391145 0.180373 0.083 Uiso 1 1 calc R U . . .
H14B H 0.190125 0.386889 0.200976 0.083 Uiso 1 1 calc R U . . .
H14C H 0.220083 0.598996 0.228025 0.083 Uiso 1 1 calc R U . . .
C15 C 0.12904(6) 1.0505(3) 0.33633(10) 0.0263(4) Uani 1 1 d . . . . .
C16 C 0.15723(8) 0.7548(4) 0.41163(12) 0.0454(7) Uani 1 1 d . . . . .
H16A H 0.186530 0.795054 0.398970 0.068 Uiso 1 1 calc R U . . .
H16B H 0.155087 0.582441 0.420321 0.068 Uiso 1 1 calc R U . . .
H16C H 0.149260 0.842564 0.453738 0.068 Uiso 1 1 calc R U . . .
C17 C 0.03960(6) 0.9823(3) 0.36379(10) 0.0258(4) Uani 1 1 d . . . . .
C18 C 0.00570(8) 0.6876(4) 0.43271(11) 0.0420(6) Uani 1 1 d . . . . .
H18A H 0.031909 0.646241 0.457624 0.063 Uiso 1 1 calc R U . . .
H18B H -0.012004 0.544330 0.427590 0.063 Uiso 1 1 calc R U . . .
H18C H -0.009914 0.809227 0.458999 0.063 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 1.388(2) . ?
O1 C10 1.441(3) . ?
O2 C17 1.344(2) . ?
O2 C18 1.455(2) . ?
O3 C17 1.208(2) . ?
O4 C15 1.337(2) . ?
O4 C16 1.450(2) . ?
O5 C15 1.200(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.395(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 C11 1.536(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.501(3) . ?
C7 C9 1.493(3) . ?
C7 C15 1.510(3) . ?
C7 C8 1.542(3) . ?
C8 C17 1.485(3) . ?
C8 C9 1.509(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.510(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C13 1.525(3) . ?
C11 C12 1.527(3) . ?
C11 C14 1.530(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C1 O1 C10 113.47(16) . . ?
C17 O2 C18 115.67(16) . . ?
C15 O4 C16 116.31(17) . . ?
O1 C1 C2 118.06(18) . . ?
O1 C1 C6 121.59(18) . . ?
C2 C1 C6 120.30(19) . . ?
C3 C2 C1 119.67(19) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.74(19) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 117.07(19) . . ?
C5 C4 C11 120.60(17) . . ?
C3 C4 C11 122.25(17) . . ?
C4 C5 C6 122.33(18) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C5 118.72(18) . . ?
C1 C6 C7 118.56(18) . . ?
C5 C6 C7 122.71(17) . . ?
C9 C7 C6 116.00(17) . . ?
C9 C7 C15 120.16(17) . . ?
C6 C7 C15 116.40(16) . . ?
C9 C7 C8 59.58(13) . . ?
C6 C7 C8 115.87(16) . . ?
C15 C7 C8 116.67(16) . . ?
C17 C8 C9 119.07(17) . . ?
C17 C8 C7 116.75(16) . . ?
C9 C8 C7 58.59(12) . . ?
C17 C8 H8 116.6 . . ?
C9 C8 H8 116.6 . . ?
C7 C8 H8 116.6 . . ?
C7 C9 C8 61.83(13) . . ?
C7 C9 C10 115.33(17) . . ?
C8 C9 C10 117.58(17) . . ?
C7 C9 H9 116.9 . . ?
C8 C9 H9 116.9 . . ?
C10 C9 H9 116.9 . . ?
O1 C10 C9 112.43(16) . . ?
O1 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
O1 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C13 C11 C12 108.9(2) . . ?
C13 C11 C14 108.5(2) . . ?
C12 C11 C14 107.45(19) . . ?
C13 C11 C4 108.07(16) . . ?
C12 C11 C4 111.65(18) . . ?
C14 C11 C4 112.16(17) . . ?
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 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 O4 124.50(19) . . ?
O5 C15 C7 125.84(18) . . ?
O4 C15 C7 109.63(16) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 124.20(18) . . ?
O3 C17 C8 125.57(19) . . ?
O2 C17 C8 110.17(16) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C10 O1 C1 C2 -147.65(18) . . . . ?
C10 O1 C1 C6 34.8(2) . . . . ?
O1 C1 C2 C3 -179.81(18) . . . . ?
C6 C1 C2 C3 -2.2(3) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C2 C3 C4 C5 3.2(3) . . . . ?
C2 C3 C4 C11 -173.52(19) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C11 C4 C5 C6 175.52(17) . . . . ?
O1 C1 C6 C5 -178.43(16) . . . . ?
C2 C1 C6 C5 4.1(3) . . . . ?
O1 C1 C6 C7 3.0(3) . . . . ?
C2 C1 C6 C7 -174.46(18) . . . . ?
C4 C5 C6 C1 -2.3(3) . . . . ?
C4 C5 C6 C7 176.16(17) . . . . ?
C1 C6 C7 C9 -18.6(3) . . . . ?
C5 C6 C7 C9 162.95(17) . . . . ?
C1 C6 C7 C15 -168.59(17) . . . . ?
C5 C6 C7 C15 12.9(3) . . . . ?
C1 C6 C7 C8 48.5(2) . . . . ?
C5 C6 C7 C8 -129.98(19) . . . . ?
C9 C7 C8 C17 -109.26(19) . . . . ?
C6 C7 C8 C17 144.47(17) . . . . ?
C15 C7 C8 C17 1.7(2) . . . . ?
C6 C7 C8 C9 -106.27(19) . . . . ?
C15 C7 C8 C9 110.93(19) . . . . ?
C6 C7 C9 C8 106.06(18) . . . . ?
C15 C7 C9 C8 -105.11(19) . . . . ?
C6 C7 C9 C10 -3.1(3) . . . . ?
C15 C7 C9 C10 145.77(19) . . . . ?
C8 C7 C9 C10 -109.1(2) . . . . ?
C17 C8 C9 C7 105.30(19) . . . . ?
C17 C8 C9 C10 -149.17(18) . . . . ?
C7 C8 C9 C10 105.5(2) . . . . ?
C1 O1 C10 C9 -55.3(2) . . . . ?
C7 C9 C10 O1 39.0(2) . . . . ?
C8 C9 C10 O1 -31.0(3) . . . . ?
C5 C4 C11 C13 -88.6(2) . . . . ?
C3 C4 C11 C13 88.1(2) . . . . ?
C5 C4 C11 C12 151.7(2) . . . . ?
C3 C4 C11 C12 -31.7(3) . . . . ?
C5 C4 C11 C14 31.0(3) . . . . ?
C3 C4 C11 C14 -152.4(2) . . . . ?
C16 O4 C15 O5 0.9(3) . . . . ?
C16 O4 C15 C7 178.74(17) . . . . ?
C9 C7 C15 O5 -47.9(3) . . . . ?
C6 C7 C15 O5 100.8(2) . . . . ?
C8 C7 C15 O5 -116.6(2) . . . . ?
C9 C7 C15 O4 134.26(18) . . . . ?
C6 C7 C15 O4 -77.0(2) . . . . ?
C8 C7 C15 O4 65.6(2) . . . . ?
C18 O2 C17 O3 -2.2(3) . . . . ?
C18 O2 C17 C8 175.35(17) . . . . ?
C9 C8 C17 O3 -16.3(3) . . . . ?
C7 C8 C17 O3 50.9(3) . . . . ?
C9 C8 C17 O2 166.16(16) . . . . ?
C7 C8 C17 O2 -126.64(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16B O5 0.98 2.41 3.242(3) 142.5 1_545 yes
C10 H10A O2 0.99 2.62 3.454(3) 141.7 2_565 yes

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1947438'
loop_
_audit_author_name
_audit_author_address
'jiayong Zhang'
;nankai university
China
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N O9'
_chemical_formula_weight         455.41

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'

_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'

_cell_length_a                   9.4995(19)
_cell_length_b                   9.5604(19)
_cell_length_c                   12.684(3)
_cell_angle_alpha                97.84(3)
_cell_angle_beta                 105.01(3)
_cell_angle_gamma                103.90(3)
_cell_volume                     1055.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3099
_cell_measurement_theta_min      1.7008
_cell_measurement_theta_max      27.8824

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7642
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12755
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.701
_diffrn_reflns_theta_max         27.882
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5013
_reflns_number_gt                3276
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²] 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_number_reflns         5013
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.002
_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 1.03273(12) 1.13281(13) 0.89441(10) 0.0289(3) Uani 1 1 d . . . . .
O2 O 0.97236(13) 1.24434(14) 0.74491(10) 0.0349(3) Uani 1 1 d . . . . .
O3 O 0.45496(13) 0.93118(13) 0.60508(9) 0.0281(3) Uani 1 1 d . . . . .
O4 O 0.64726(13) 0.66641(14) 0.91396(10) 0.0297(3) Uani 1 1 d . . . . .
O5 O 0.46887(14) 0.75985(14) 0.95558(9) 0.0306(3) Uani 1 1 d . . . . .
O6 O 0.35433(16) 0.41394(14) 0.58405(11) 0.0395(4) Uani 1 1 d . . . . .
O7 O 0.34923(14) 0.45934(14) 0.76215(10) 0.0329(3) Uani 1 1 d . . . . .
O8 O -0.16306(14) 0.38146(14) 0.55217(10) 0.0342(3) Uani 1 1 d . . . . .
O9 O -0.30314(14) 0.42611(16) 0.65510(12) 0.0435(4) Uani 1 1 d . . . . .
N1 N -0.18181(16) 0.45169(16) 0.63346(12) 0.0276(3) Uani 1 1 d . . . . .
C1 C 1.0772(2) 1.2626(3) 0.85263(18) 0.0527(6) Uani 1 1 d . . . . .
H1A H 1.075943 1.350057 0.903697 0.063 Uiso 1 1 calc R U . . .
H1B H 1.181663 1.277278 0.847162 0.063 Uiso 1 1 calc R U . . .
C2 C 0.88156(17) 1.06741(19) 0.83169(13) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.77725(17) 0.95399(18) 0.84981(13) 0.0205(3) Uani 1 1 d . . . . .
H3 H 0.803110 0.910030 0.912181 0.025 Uiso 1 1 calc R U . . .
C4 C 0.63003(17) 0.90513(18) 0.77224(13) 0.0200(3) Uani 1 1 d . . . . .
C5 C 0.59784(18) 0.97539(19) 0.68319(13) 0.0233(4) Uani 1 1 d . . . . .
C6 C 0.70512(19) 1.09000(19) 0.66540(14) 0.0274(4) Uani 1 1 d . . . . .
H6 H 0.681207 1.135211 0.603485 0.033 Uiso 1 1 calc R U . . .
C7 C 0.84678(18) 1.13387(19) 0.74196(14) 0.0258(4) Uani 1 1 d . . . . .
C8 C 0.33371(18) 0.88905(19) 0.65160(14) 0.0255(4) Uani 1 1 d . . . . .
H8A H 0.236004 0.856235 0.590623 0.031 Uiso 1 1 calc R U . . .
H8B H 0.332375 0.976306 0.702859 0.031 Uiso 1 1 calc R U . . .
C9 C 0.50673(17) 0.77701(17) 0.78096(13) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.54767(18) 0.72489(18) 0.88913(13) 0.0214(3) Uani 1 1 d . . . . .
C11 C 0.4963(2) 0.7114(2) 1.06175(15) 0.0384(5) Uani 1 1 d . . . . .
H11A H 0.581211 0.786658 1.119904 0.046 Uiso 1 1 calc R U . . .
H11B H 0.523851 0.617871 1.053410 0.046 Uiso 1 1 calc R U . . .
C12 C 0.3546(3) 0.6899(3) 1.09424(19) 0.0496(6) Uani 1 1 d . . . . .
H12A H 0.327346 0.782605 1.100910 0.074 Uiso 1 1 calc R U . . .
H12B H 0.370825 0.659537 1.166117 0.074 Uiso 1 1 calc R U . . .
H12C H 0.272006 0.613425 1.037133 0.074 Uiso 1 1 calc R U . . .
C13 C 0.34576(17) 0.76644(17) 0.71507(13) 0.0200(3) Uani 1 1 d . . . . .
C14 C 0.42326(17) 0.65824(17) 0.67305(13) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.457201 0.675761 0.606420 0.024 Uiso 1 1 calc R U . . .
C15 C 0.37195(18) 0.50145(19) 0.68105(14) 0.0244(4) Uani 1 1 d . . . . .
C16 C 0.3118(3) 0.2552(2) 0.5778(2) 0.0553(6) Uani 1 1 d . . . . .
H16A H 0.383939 0.212398 0.550067 0.066 Uiso 1 1 calc R U . . .
H16B H 0.317984 0.235783 0.653281 0.066 Uiso 1 1 calc R U . . .
C17 C 0.1600(3) 0.1865(3) 0.5044(3) 0.0960(12) Uani 1 1 d . . . . .
H17A H 0.087364 0.218720 0.537190 0.144 Uiso 1 1 calc R U . . .
H17B H 0.138031 0.079165 0.493719 0.144 Uiso 1 1 calc R U . . .
H17C H 0.151027 0.214891 0.432042 0.144 Uiso 1 1 calc R U . . .
C18 C 0.20533(18) 0.71951(18) 0.75007(13) 0.0220(4) Uani 1 1 d . . . . .
C19 C 0.18593(19) 0.8056(2) 0.84051(14) 0.0276(4) Uani 1 1 d . . . . .
H19 H 0.266930 0.888545 0.885504 0.033 Uiso 1 1 calc R U . . .
C20 C 0.0494(2) 0.7708(2) 0.86503(15) 0.0324(4) Uani 1 1 d . . . . .
H20 H 0.038979 0.828643 0.928136 0.039 Uiso 1 1 calc R U . . .
C21 C -0.0719(2) 0.6534(2) 0.79917(15) 0.0309(4) Uani 1 1 d . . . . .
H21 H -0.165556 0.629331 0.815885 0.037 Uiso 1 1 calc R U . . .
C22 C -0.05211(18) 0.57240(18) 0.70832(13) 0.0234(4) Uani 1 1 d . . . . .
C23 C 0.08357(18) 0.60233(18) 0.68230(13) 0.0223(4) Uani 1 1 d . . . . .
H23 H 0.093179 0.543749 0.619213 0.027 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 C2 1.3882(19) . ?
O1 C1 1.429(2) . ?
O2 C7 1.379(2) . ?
O2 C1 1.427(2) . ?
O3 C5 1.3842(19) . ?
O3 C8 1.425(2) . ?
O4 C10 1.2061(19) . ?
O5 C10 1.3239(19) . ?
O5 C11 1.464(2) . ?
O6 C15 1.337(2) . ?
O6 C16 1.459(2) . ?
O7 C15 1.205(2) . ?
O8 N1 1.2286(19) . ?
O9 N1 1.2289(17) . ?
N1 C22 1.471(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.371(2) . ?
C2 C7 1.383(2) . ?
C3 C4 1.411(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C9 1.516(2) . ?
C5 C6 1.393(2) . ?
C6 C7 1.368(2) . ?
C6 H6 0.9500 . ?
C8 C13 1.520(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.512(2) . ?
C9 C13 1.512(2) . ?
C9 C14 1.540(2) . ?
C11 C12 1.484(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.501(2) . ?
C13 C14 1.521(2) . ?
C14 C15 1.487(2) . ?
C14 H14 1.0000 . ?
C16 C17 1.436(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.390(2) . ?
C18 C19 1.397(2) . ?
C19 C20 1.386(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(2) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 104.31(13) . . ?
C7 O2 C1 104.47(13) . . ?
C5 O3 C8 113.68(12) . . ?
C10 O5 C11 116.91(13) . . ?
C15 O6 C16 117.39(15) . . ?
O8 N1 O9 123.31(16) . . ?
O8 N1 C22 118.08(14) . . ?
O9 N1 C22 118.61(15) . . ?
O2 C1 O1 108.07(15) . . ?
O2 C1 H1A 110.1 . . ?
O1 C1 H1A 110.1 . . ?
O2 C1 H1B 110.1 . . ?
O1 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
C3 C2 C7 122.50(15) . . ?
C3 C2 O1 128.25(15) . . ?
C7 C2 O1 109.25(14) . . ?
C2 C3 C4 117.41(15) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 118.78(14) . . ?
C5 C4 C9 118.92(14) . . ?
C3 C4 C9 122.29(14) . . ?
O3 C5 C6 115.99(14) . . ?
O3 C5 C4 120.77(14) . . ?
C6 C5 C4 123.23(15) . . ?
C7 C6 C5 116.33(15) . . ?
C7 C6 H6 121.8 . . ?
C5 C6 H6 121.8 . . ?
C6 C7 O2 128.27(15) . . ?
C6 C7 C2 121.74(15) . . ?
O2 C7 C2 109.99(14) . . ?
O3 C8 C13 113.49(13) . . ?
O3 C8 H8A 108.9 . . ?
C13 C8 H8A 108.9 . . ?
O3 C8 H8B 108.9 . . ?
C13 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C13 123.89(13) . . ?
C10 C9 C4 113.74(13) . . ?
C13 C9 C4 115.75(14) . . ?
C10 C9 C14 117.36(13) . . ?
C13 C9 C14 59.78(11) . . ?
C4 C9 C14 115.65(13) . . ?
O4 C10 O5 124.38(14) . . ?
O4 C10 C9 123.35(14) . . ?
O5 C10 C9 112.13(13) . . ?
O5 C11 C12 107.90(16) . . ?
O5 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O5 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
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 . . ?
C18 C13 C9 126.79(13) . . ?
C18 C13 C8 109.27(13) . . ?
C9 C13 C8 114.03(13) . . ?
C18 C13 C14 123.07(14) . . ?
C9 C13 C14 61.02(10) . . ?
C8 C13 C14 115.46(14) . . ?
C15 C14 C13 119.10(14) . . ?
C15 C14 C9 119.13(13) . . ?
C13 C14 C9 59.20(10) . . ?
C15 C14 H14 115.9 . . ?
C13 C14 H14 115.9 . . ?
C9 C14 H14 115.9 . . ?
O7 C15 O6 125.11(16) . . ?
O7 C15 C14 125.46(16) . . ?
O6 C15 C14 109.44(14) . . ?
C17 C16 O6 110.6(2) . . ?
C17 C16 H16A 109.5 . . ?
O6 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 119.00(15) . . ?
C23 C18 C13 119.64(15) . . ?
C19 C18 C13 120.62(15) . . ?
C20 C19 C18 120.46(17) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 121.05(17) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 117.64(16) . . ?
C22 C21 H21 121.2 . . ?
C20 C21 H21 121.2 . . ?
C21 C22 C23 122.91(16) . . ?
C21 C22 N1 118.76(15) . . ?
C23 C22 N1 118.29(15) . . ?
C22 C23 C18 118.87(16) . . ?
C22 C23 H23 120.6 . . ?
C18 C23 H23 120.6 . . ?

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
C7 O2 C1 O1 19.0(2) . . . . ?
C2 O1 C1 O2 -19.5(2) . . . . ?
C1 O1 C2 C3 -168.11(19) . . . . ?
C1 O1 C2 C7 12.5(2) . . . . ?
C7 C2 C3 C4 0.3(3) . . . . ?
O1 C2 C3 C4 -178.95(15) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C2 C3 C4 C9 177.71(14) . . . . ?
C8 O3 C5 C6 -143.93(16) . . . . ?
C8 O3 C5 C4 37.4(2) . . . . ?
C3 C4 C5 O3 -179.98(14) . . . . ?
C9 C4 C5 O3 1.3(2) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C9 C4 C5 C6 -177.33(16) . . . . ?
O3 C5 C6 C7 -179.72(15) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C5 C6 C7 O2 -179.35(16) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C1 O2 C7 C6 168.5(2) . . . . ?
C1 O2 C7 C2 -11.2(2) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
O1 C2 C7 C6 179.40(16) . . . . ?
C3 C2 C7 O2 179.74(16) . . . . ?
O1 C2 C7 O2 -0.9(2) . . . . ?
C5 O3 C8 C13 -56.92(19) . . . . ?
C5 C4 C9 C10 -171.61(14) . . . . ?
C3 C4 C9 C10 9.7(2) . . . . ?
C5 C4 C9 C13 -18.9(2) . . . . ?
C3 C4 C9 C13 162.34(14) . . . . ?
C5 C4 C9 C14 48.2(2) . . . . ?
C3 C4 C9 C14 -130.51(16) . . . . ?
C11 O5 C10 O4 -5.8(3) . . . . ?
C11 O5 C10 C9 178.46(14) . . . . ?
C13 C9 C10 O4 142.72(17) . . . . ?
C4 C9 C10 O4 -67.2(2) . . . . ?
C14 C9 C10 O4 72.3(2) . . . . ?
C13 C9 C10 O5 -41.5(2) . . . . ?
C4 C9 C10 O5 108.60(16) . . . . ?
C14 C9 C10 O5 -111.93(16) . . . . ?
C10 O5 C11 C12 -151.35(17) . . . . ?
C10 C9 C13 C18 6.9(2) . . . . ?
C4 C9 C13 C18 -142.63(16) . . . . ?
C14 C9 C13 C18 111.39(18) . . . . ?
C10 C9 C13 C8 148.63(15) . . . . ?
C4 C9 C13 C8 -0.9(2) . . . . ?
C14 C9 C13 C8 -106.93(15) . . . . ?
C10 C9 C13 C14 -104.45(17) . . . . ?
C4 C9 C13 C14 105.98(15) . . . . ?
O3 C8 C13 C18 -174.08(13) . . . . ?
O3 C8 C13 C9 37.65(19) . . . . ?
O3 C8 C13 C14 -30.31(19) . . . . ?
C18 C13 C14 C15 -8.7(2) . . . . ?
C9 C13 C14 C15 108.47(16) . . . . ?
C8 C13 C14 C15 -146.94(15) . . . . ?
C18 C13 C14 C9 -117.14(16) . . . . ?
C8 C13 C14 C9 104.59(15) . . . . ?
C10 C9 C14 C15 6.7(2) . . . . ?
C13 C9 C14 C15 -108.42(16) . . . . ?
C4 C9 C14 C15 145.45(15) . . . . ?
C10 C9 C14 C13 115.16(15) . . . . ?
C4 C9 C14 C13 -106.14(16) . . . . ?
C16 O6 C15 O7 -3.3(3) . . . . ?
C16 O6 C15 C14 176.87(16) . . . . ?
C13 C14 C15 O7 -46.4(2) . . . . ?
C9 C14 C15 O7 22.5(2) . . . . ?
C13 C14 C15 O6 133.44(15) . . . . ?
C9 C14 C15 O6 -157.71(14) . . . . ?
C15 O6 C16 C17 111.8(3) . . . . ?
C9 C13 C18 C23 -123.51(18) . . . . ?
C8 C13 C18 C23 93.35(18) . . . . ?
C14 C13 C18 C23 -47.1(2) . . . . ?
C9 C13 C18 C19 66.4(2) . . . . ?
C8 C13 C18 C19 -76.72(18) . . . . ?
C14 C13 C18 C19 142.83(16) . . . . ?
C23 C18 C19 C20 2.7(2) . . . . ?
C13 C18 C19 C20 172.85(16) . . . . ?
C18 C19 C20 C21 -1.9(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 1.2(3) . . . . ?
C20 C21 C22 N1 -176.83(16) . . . . ?
O8 N1 C22 C21 179.23(15) . . . . ?
O9 N1 C22 C21 -0.7(2) . . . . ?
O8 N1 C22 C23 1.1(2) . . . . ?
O9 N1 C22 C23 -178.87(14) . . . . ?
C21 C22 C23 C18 -0.4(3) . . . . ?
N1 C22 C23 C18 177.68(14) . . . . ?
C19 C18 C23 C22 -1.6(2) . . . . ?
C13 C18 C23 C22 -171.83(14) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_p20181113b2_tw
_database_code_depnum_ccdc_archive 'CCDC 1947441'
loop_
_audit_author_name
_audit_author_address
'Jiayong Zhang'
;nankai university
China
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_audit_creation_date             2018-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N O6 S'
_chemical_formula_sum            'C23 H25 N O6 S'
_chemical_formula_weight         443.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7393(2)
_cell_length_b                   9.8405(3)
_cell_length_c                   28.4880(6)
_cell_angle_alpha                80.848(2)
_cell_angle_beta                 87.645(2)
_cell_angle_gamma                69.047(2)
_cell_volume                     2258.48(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15318
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.8670
_cell_measurement_theta_min      4.8750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8595
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.331
_diffrn_reflns_theta_min         3.143
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -14.00   0.50    1.00    --  -39.10  68.00-167.32   96
  2  ω    -42.00  24.00   0.50    1.00    --  -39.10  56.00  12.56  132
  3  ω    -40.00  37.00   0.50    1.00    --  -39.10  72.00  30.00  154
  4  ω    -51.00 -10.00   0.50    1.00    --  -39.10  72.00 -90.00   82
  5  ω      0.00  30.00   0.50    1.00    --  -39.10  72.00 -90.00   60
  6  ω    -56.00  43.00   0.50    1.00    --  -39.10  38.00-180.00  198
  7  ω    -62.00  46.00   0.50    1.00    --  -39.10  22.00 -53.57  216
  8  ω   -126.00 -85.00   0.50    4.00    -- -110.00  37.00  72.64   82
  9  ω   -132.00 -88.00   0.50    4.00    -- -110.00  66.00-123.27   88
 10  ω    -56.00 -22.00   0.50    4.00    -- -110.00  64.00  21.51   68
 11  ω   -135.00-109.00   0.50    4.00    -- -110.00 -30.00 122.22   52
 12  ω   -118.00 -82.00   0.50    4.00    -- -110.00  42.00 -84.06   72
 13  ω    -56.00 -30.00   0.50    4.00    -- -110.00  42.00 -84.06   52
 14  ω   -194.00-167.00   0.50    4.00    -- -110.00 -29.00 -45.56   54
 15  ω   -179.00-153.00   0.50    4.00    -- -110.00 -30.00 122.22   52
 16  ω   -127.00 -89.00   0.50    4.00    -- -110.00 -31.00 -62.62   76
 17  ω   -112.00 -86.00   0.50    4.00    -- -110.00  63.00   7.43   52
 18  ω   -188.00-151.00   0.50    4.00    -- -110.00 -19.00  30.00   74
 19  ω   -133.00-107.00   0.50    4.00    -- -110.00 -19.00  30.00   52
 20  ω    -56.00 -22.00   0.50    4.00    -- -110.00  19.00-150.00   68
 21  ω   -133.00 -24.00   0.50    4.00    -- -110.00  72.00  90.00  218
 22  ω   -132.00 -24.00   0.50    4.00    -- -110.00  57.00 -90.00  216
 23  ω   -127.00 -22.00   0.50    4.00    -- -110.00  72.00   0.00  210
 24  ω   -118.00 -92.00   0.50    4.00    -- -110.00  57.00 150.00   52
 25  ω    -57.00 -31.00   0.50    4.00    -- -110.00  38.00 -30.00   52
 26  ω   -127.00 -43.00   0.50    4.00    -- -110.00  72.00-150.00  168
 27  ω   -124.00 -28.00   0.50    4.00    -- -110.00  72.00  60.00  192
 28  ω   -160.00-124.00   0.50    4.00    -- -110.00 -22.00 163.72   72
 29  ω   -132.00 -72.00   0.50    4.00    -- -110.00  72.00-120.00  120
 30  ω    -85.00 -33.00   0.50    4.00    -- -110.00  72.00 -60.00  104
 31  ω   -133.00-106.00   0.50    4.00    -- -110.00  38.00-180.00   54
 32  ω   -199.00-172.00   0.50    4.00    -- -110.00 -31.00 -62.62   54
 33  ω    -49.00 -22.00   0.50    4.00    -- -110.00  72.00  30.00   54
 34  ω   -106.00 -62.00   0.50    4.00    -- -110.00  72.00  30.00   88
 35  ω   -115.00 -90.00   0.50    4.00    -- -110.00  72.00 150.00   50
 36  ω    -96.00 -71.00   0.50    4.00    -- -110.00  38.00-180.00   50
 37  ω    -97.00 -46.00   0.50    4.00    -- -110.00  72.00 120.00  102
 38  ω   -123.00 -97.00   0.50    4.00    -- -110.00  38.00  30.00   52
 39  ω    -82.00 -57.00   0.50    4.00    -- -110.00  38.00  30.00   50
 40  ω   -130.00-105.00   0.50    4.00    -- -110.00  19.00-150.00   50
 41  ω   -118.00 -93.00   0.50    4.00    -- -110.00 -29.00 -45.56   50
 42  ω   -167.00-142.00   0.50    4.00    -- -110.00 -19.00-180.00   50
 43  ω   -132.00 -96.00   0.50    4.00    -- -110.00 -19.00-180.00   72
 44  ω    -48.00 -23.00   0.50    4.00    -- -110.00  72.00-180.00   50
 45  ω   -185.00-156.00   0.50    4.00    -- -110.00 -19.00 120.00   58
 46  ω    -94.00 -55.00   0.50    4.00    -- -110.00  27.00 -84.85   78
 47  ω   -109.00 -83.00   0.50    4.00    -- -110.00  57.00  30.00   52
 48  ω   -116.00 -91.00   0.50    4.00    -- -110.00  57.00 120.00   50
 49  ω    -64.00 -27.00   0.50    4.00    -- -110.00  57.00 120.00   74
 50  ω   -119.00 -82.00   0.50    4.00    -- -110.00  38.00 -30.00   74
 51  ω   -108.00 -66.00   0.50    4.00    -- -110.00  72.00-180.00   84
 52  ω   -174.00-148.00   0.50    4.00    -- -110.00 -72.00  60.00   52
 53  ω   -126.00-100.00   0.50    4.00    -- -110.00 -72.00  60.00   52
 54  ω   -128.00-103.00   0.50    4.00    -- -110.00  13.00  14.28   50
 55  ω    -96.00 -23.00   0.50    4.00    -- -110.00  13.00  14.28  146
 56  ω   -100.00 -21.00   0.50    4.00    -- -110.00  72.00 -90.00  158
 57  ω   -109.00 -71.00   0.50    4.00    -- -110.00  72.00 -30.00   76
 58  ω   -133.00 -85.00   0.50    4.00    -- -110.00  38.00-120.00   96
 59  ω    -47.00 -22.00   0.50    4.00    -- -110.00  38.00-120.00   50
 60  ω    -86.00 -56.00   0.50    4.00    -- -110.00  38.00  90.00   60
 61  ω   -195.00-122.00   0.50    4.00    -- -110.00 -19.00-150.00  146
 62  ω   -188.00-140.00   0.50    4.00    -- -110.00 -19.00  60.00   96
 63  ω   -147.00-121.00   0.50    4.00    -- -110.00 -29.00 -45.56   52
 64  ω    -78.00 -37.00   0.50    4.00    -- -110.00  37.00  72.64   82
 65  ω   -134.00-109.00   0.50    4.00    -- -110.00 -19.00 120.00   50
 66  ω   -186.00-155.00   0.50    4.00    -- -110.00 -72.00-120.00   62
 67  ω   -133.00 -48.00   0.50    4.00    -- -110.00   8.00-145.29  170
 68  ω   -125.00-100.00   0.50    4.00    -- -110.00  23.00-138.89   50
 69  ω    -79.00 -54.00   0.50    4.00    -- -110.00  23.00-138.89   50
 70  ω    -91.00 -65.00   0.50    4.00    -- -110.00  71.00 -75.70   52
 71  ω   -113.00 -88.00   0.50    4.00    -- -110.00  64.00  21.51   50
 72  ω    -93.00 -67.00   0.50    4.00    -- -110.00  57.00  90.00   52
 73  ω   -104.00 -79.00   0.50    4.00    -- -110.00  19.00  30.00   50
 74  ω   -117.00 -90.00   0.50    4.00    -- -110.00 -19.00  90.00   54
 75  ω   -173.00-147.00   0.50    4.00    -- -110.00 -38.00-120.00   52
 76  ω   -197.00-113.00   0.50    4.00    -- -110.00 -72.00-180.00  168
 77  ω    -79.00 -53.00   0.50    4.00    -- -110.00  46.00-133.76   52
 78  ω    -93.00 -40.00   0.50    4.00    -- -110.00  72.00 152.47  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7774
_reflns_number_total             8595
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     606
_refine_ls_number_reflns         8595
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0984P)²+2.1291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2291
_refine_ls_wR_factor_ref         0.2315
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.894(3)
 0.106(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C12-C13 = C12A-C13A = C35-C36 = C35A-C36A
 1.54 with sigma of 0.01
 O2-C12 \\sim O2-C12A \\sim O8-C35 \\sim O8-C35A
 with sigma of 0.01
 O2-C13 \\sim O2-C13A \\sim O8-C36 \\sim O8-C36A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13A)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C35A) \\sim Ueq,
Uanis(C36A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
 Sof(C35A)=Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(2)
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C25(H25), C26(H26)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C15(H15A,H15B), C24(H24A,H24B), C35(H35A,H35B),
 C38(H38A,H38B), C12A(H12C,H12D), C35A(H35C,H35D)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C21(H21), C22(H22),
 C30(H30), C31(H31), C32(H32), C33(H33), C41(H41), C42(H42), C44(H44), C45(H45)
6.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C36(H36A,H36B,
 H36C), C39(H39A,H39B,H39C), C46(H46A,H46B,H46C), C13A(H13D,H13E,H13F),
 C36A(H36D,H36E,H36F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.62684(12) 0.83320(11) 0.19775(4) 0.0684(3) Uani 1 1 d . . . . .
O1 O 1.2517(4) 0.3914(4) 0.12992(15) 0.0986(11) Uani 1 1 d . . . . .
O2 O 1.0281(4) 0.3325(3) 0.13354(14) 0.0889(10) Uani 1 1 d D . . . .
O3 O 1.2828(4) 0.6998(4) 0.07330(11) 0.0815(9) Uani 1 1 d . . . . .
O4 O 1.1468(3) 0.5927(4) 0.03589(10) 0.0766(8) Uani 1 1 d . . . . .
O5 O 0.6710(5) 0.8486(4) 0.24350(11) 0.0915(10) Uani 1 1 d . . . . .
O6 O 0.4735(4) 0.9277(3) 0.17692(14) 0.0974(12) Uani 1 1 d . . . . .
N1 N 0.7711(4) 0.8569(3) 0.16177(11) 0.0594(7) Uani 1 1 d . . . . .
C1 C 0.9391(5) 0.7938(5) 0.18071(14) 0.0662(9) Uani 1 1 d . . . . .
H1A H 0.938285 0.748512 0.213509 0.079 Uiso 1 1 calc R . . . .
H1B H 0.982223 0.872078 0.180311 0.079 Uiso 1 1 calc R . . . .
C2 C 1.0497(4) 0.6805(4) 0.15274(13) 0.0596(8) Uani 1 1 d . . . . .
H2 H 1.165480 0.640583 0.162561 0.072 Uiso 1 1 calc R . . . .
C3 C 0.9886(4) 0.5760(4) 0.13297(13) 0.0583(8) Uani 1 1 d . . . . .
H3 H 0.873996 0.586749 0.139160 0.070 Uiso 1 1 calc R . . . .
C4 C 1.0181(4) 0.7050(4) 0.10053(12) 0.0564(8) Uani 1 1 d . . . . .
C5 C 0.8715(4) 0.8344(4) 0.08121(13) 0.0576(8) Uani 1 1 d . . . . .
C6 C 0.7499(4) 0.9062(4) 0.11198(13) 0.0572(8) Uani 1 1 d . . . . .
C7 C 0.6191(5) 1.0310(5) 0.09364(17) 0.0752(11) Uani 1 1 d . . . . .
H7 H 0.540538 1.080768 0.113989 0.090 Uiso 1 1 calc R . . . .
C8 C 0.6051(6) 1.0815(5) 0.04538(19) 0.0906(15) Uani 1 1 d . . . . .
H8 H 0.514139 1.162090 0.033247 0.109 Uiso 1 1 calc R . . . .
C9 C 0.7236(7) 1.0144(6) 0.01538(17) 0.0919(15) Uani 1 1 d . . . . .
H9 H 0.715642 1.051045 -0.016954 0.110 Uiso 1 1 calc R . . . .
C10 C 0.8550(5) 0.8921(5) 0.03319(15) 0.0751(11) Uani 1 1 d . . . . .
H10 H 0.935108 0.846709 0.012460 0.090 Uiso 1 1 calc R . . . .
C11 C 1.1051(5) 0.4248(4) 0.13185(15) 0.0668(10) Uani 1 1 d . . . . .
C12 C 1.1478(12) 0.1863(10) 0.1225(7) 0.087(4) Uani 0.48(2) 1 d D U P A 1
H12A H 1.208266 0.199774 0.093914 0.104 Uiso 0.48(2) 1 calc R . P A 1
H12B H 1.224582 0.135346 0.148734 0.104 Uiso 0.48(2) 1 calc R . P A 1
C13 C 1.036(2) 0.1040(14) 0.1156(9) 0.129(7) Uani 0.48(2) 1 d D U P A 1
H13A H 0.975222 0.146597 0.086224 0.193 Uiso 0.48(2) 1 calc GR . P A 1
H13B H 0.961251 0.110555 0.141497 0.193 Uiso 0.48(2) 1 calc GR . P A 1
H13C H 1.100314 0.002423 0.114535 0.193 Uiso 0.48(2) 1 calc GR . P A 1
C14 C 1.1653(5) 0.6659(5) 0.06940(14) 0.0653(9) Uani 1 1 d . . . . .
C15 C 1.2862(6) 0.5409(7) 0.00566(19) 0.0939(16) Uani 1 1 d . . . . .
H15A H 1.309319 0.624098 -0.011885 0.113 Uiso 1 1 calc R . . . .
H15B H 1.382068 0.479211 0.024985 0.113 Uiso 1 1 calc R . . . .
C16 C 1.2514(7) 0.4583(8) -0.0268(2) 0.116(2) Uani 1 1 d . . . . .
H16A H 1.343375 0.425125 -0.047123 0.174 Uiso 1 1 calc GR . . . .
H16B H 1.156335 0.519702 -0.045795 0.174 Uiso 1 1 calc GR . . . .
H16C H 1.231153 0.374847 -0.009313 0.174 Uiso 1 1 calc GR . . . .
C17 C 0.6359(4) 0.6520(4) 0.19991(12) 0.0564(8) Uani 1 1 d . . . . .
C18 C 0.7224(5) 0.5434(4) 0.23629(14) 0.0669(9) Uani 1 1 d . . . . .
H18 H 0.775455 0.567079 0.259681 0.080 Uiso 1 1 calc R . . . .
C19 C 0.7299(6) 0.4015(5) 0.23784(17) 0.0783(12) Uani 1 1 d . . . . .
H19 H 0.788535 0.329547 0.262380 0.094 Uiso 1 1 calc R . . . .
C20 C 0.6521(5) 0.3629(5) 0.2037(2) 0.0810(12) Uani 1 1 d . . . . .
C21 C 0.5666(6) 0.4727(6) 0.16698(18) 0.0805(12) Uani 1 1 d . . . . .
H21 H 0.514660 0.448787 0.143383 0.097 Uiso 1 1 calc R . . . .
C22 C 0.5579(5) 0.6153(5) 0.16518(15) 0.0679(10) Uani 1 1 d . . . . .
H22 H 0.499615 0.687367 0.140630 0.082 Uiso 1 1 calc R . . . .
C23 C 0.6577(9) 0.2090(7) 0.2056(3) 0.128(2) Uani 1 1 d . . . . .
H23A H 0.725993 0.146888 0.231875 0.191 Uiso 1 1 calc GR . . . .
H23B H 0.701663 0.173991 0.176505 0.191 Uiso 1 1 calc GR . . . .
H23C H 0.548871 0.206845 0.209533 0.191 Uiso 1 1 calc GR . . . .
S2 S 0.09343(12) 1.01269(11) 0.30294(4) 0.0697(3) Uani 1 1 d . . . . .
O7 O 0.7346(3) 0.5145(4) 0.36877(13) 0.0837(9) Uani 1 1 d . . . . .
O8 O 0.5128(4) 0.4522(3) 0.37222(15) 0.0909(10) Uani 1 1 d D . . . .
O9 O 0.7702(4) 0.7730(4) 0.42516(11) 0.0785(8) Uani 1 1 d . . . . .
O10 O 0.6427(3) 0.6266(3) 0.46326(10) 0.0725(7) Uani 1 1 d . . . . .
O11 O 0.1206(4) 1.0787(4) 0.25731(11) 0.0904(10) Uani 1 1 d . . . . .
O12 O -0.0563(4) 1.0763(4) 0.32622(13) 0.0935(11) Uani 1 1 d . . . . .
N2 N 0.2438(4) 1.0069(3) 0.33752(11) 0.0610(7) Uani 1 1 d . . . . .
C24 C 0.4091(5) 0.9633(4) 0.31797(14) 0.0629(9) Uani 1 1 d . . . . .
H24A H 0.451112 1.042251 0.317786 0.075 Uiso 1 1 calc R . . . .
H24B H 0.403898 0.948078 0.285349 0.075 Uiso 1 1 calc R . . . .
C25 C 0.5255(4) 0.8237(4) 0.34643(12) 0.0572(8) Uani 1 1 d . . . . .
H25 H 0.639712 0.793518 0.336203 0.069 Uiso 1 1 calc R . . . .
C26 C 0.4684(4) 0.6994(4) 0.36733(12) 0.0541(8) Uani 1 1 d . . . . .
H26 H 0.353285 0.714228 0.361746 0.065 Uiso 1 1 calc R . . . .
C27 C 0.5025(4) 0.7998(4) 0.39873(12) 0.0549(8) Uani 1 1 d . . . . .
C28 C 0.3584(4) 0.9117(4) 0.41782(13) 0.0587(8) Uani 1 1 d . . . . .
C29 C 0.2319(4) 1.0096(4) 0.38743(13) 0.0593(8) Uani 1 1 d . . . . .
C30 C 0.1032(5) 1.1187(5) 0.40556(17) 0.0765(11) Uani 1 1 d . . . . .
H30 H 0.021801 1.187110 0.385127 0.092 Uiso 1 1 calc R . . . .
C31 C 0.0962(6) 1.1255(6) 0.45317(19) 0.0898(15) Uani 1 1 d . . . . .
H31 H 0.006555 1.194751 0.465147 0.108 Uiso 1 1 calc R . . . .
C32 C 0.2192(7) 1.0318(7) 0.48331(18) 0.0925(15) Uani 1 1 d . . . . .
H32 H 0.215277 1.039553 0.515484 0.111 Uiso 1 1 calc R . . . .
C33 C 0.3500(6) 0.9252(5) 0.46589(15) 0.0751(11) Uani 1 1 d . . . . .
H33 H 0.433667 0.861559 0.486594 0.090 Uiso 1 1 calc R . . . .
C34 C 0.5878(4) 0.5473(4) 0.36932(14) 0.0604(9) Uani 1 1 d . . . . .
C35 C 0.6016(16) 0.3017(9) 0.3594(5) 0.079(4) Uani 0.45(2) 1 d D U P B 1
H35A H 0.715762 0.286335 0.352629 0.095 Uiso 0.45(2) 1 calc R . P B 1
H35B H 0.550332 0.286199 0.332151 0.095 Uiso 0.45(2) 1 calc R . P B 1
C36 C 0.584(3) 0.2017(11) 0.4043(6) 0.125(7) Uani 0.45(2) 1 d D U P B 1
H36A H 0.472485 0.207618 0.407289 0.188 Uiso 0.45(2) 1 calc GR . P B 1
H36B H 0.616343 0.232372 0.431460 0.188 Uiso 0.45(2) 1 calc GR . P B 1
H36C H 0.653611 0.101927 0.402373 0.188 Uiso 0.45(2) 1 calc GR . P B 1
C37 C 0.6548(5) 0.7352(5) 0.42942(13) 0.0617(9) Uani 1 1 d . . . . .
C38 C 0.7877(6) 0.5479(7) 0.49302(19) 0.0914(15) Uani 1 1 d . . . . .
H38A H 0.880693 0.504756 0.473524 0.110 Uiso 1 1 calc R . . . .
H38B H 0.812655 0.615092 0.510239 0.110 Uiso 1 1 calc R . . . .
C39 C 0.7565(7) 0.4337(7) 0.5261(2) 0.113(2) Uani 1 1 d . . . . .
H39A H 0.712377 0.378704 0.509122 0.170 Uiso 1 1 calc GR . . . .
H39B H 0.679335 0.477463 0.549214 0.170 Uiso 1 1 calc GR . . . .
H39C H 0.857113 0.368848 0.541824 0.170 Uiso 1 1 calc GR . . . .
C40 C 0.1180(4) 0.8290(4) 0.29929(13) 0.0605(9) Uani 1 1 d . . . . .
C41 C 0.0325(5) 0.7581(5) 0.32935(16) 0.0735(11) Uani 1 1 d . . . . .
H41 H -0.038407 0.806440 0.351594 0.088 Uiso 1 1 calc R . . . .
C42 C 0.0540(6) 0.6149(6) 0.32579(19) 0.0881(14) Uani 1 1 d . . . . .
H42 H -0.006505 0.568140 0.345146 0.106 Uiso 1 1 calc R . . . .
C43 C 0.1622(5) 0.5386(5) 0.29453(18) 0.0766(12) Uani 1 1 d . . . . .
C44 C 0.2496(5) 0.6115(5) 0.26504(15) 0.0707(10) Uani 1 1 d . . . . .
H44 H 0.324269 0.561601 0.243832 0.085 Uiso 1 1 calc R . . . .
C45 C 0.2267(5) 0.7554(4) 0.26702(13) 0.0620(9) Uani 1 1 d . . . . .
H45 H 0.283712 0.803642 0.246783 0.074 Uiso 1 1 calc R . . . .
C46 C 0.1806(9) 0.3838(7) 0.2894(3) 0.128(2) Uani 1 1 d . . . . .
H46A H 0.157299 0.334389 0.319189 0.193 Uiso 1 1 calc GR . . . .
H46B H 0.290741 0.331979 0.280510 0.193 Uiso 1 1 calc GR . . . .
H46C H 0.105491 0.386251 0.265386 0.193 Uiso 1 1 calc GR . . . .
C12A C 1.1138(16) 0.1690(8) 0.1444(4) 0.078(3) Uani 0.52(2) 1 d D U P A 2
H12C H 1.057145 0.125088 0.168679 0.094 Uiso 0.52(2) 1 calc R . P A 2
H12D H 1.226105 0.144076 0.154835 0.094 Uiso 0.52(2) 1 calc R . P A 2
C13A C 1.107(3) 0.1188(12) 0.0974(4) 0.117(6) Uani 0.52(2) 1 d D U P A 2
H13D H 1.170036 0.158755 0.074507 0.175 Uiso 0.52(2) 1 calc GR . P A 2
H13E H 0.995700 0.152558 0.086424 0.175 Uiso 0.52(2) 1 calc GR . P A 2
H13F H 1.152528 0.013203 0.101324 0.175 Uiso 0.52(2) 1 calc GR . P A 2
C35A C 0.6319(10) 0.2967(7) 0.3855(5) 0.078(3) Uani 0.55(2) 1 d D U P B 2
H35C H 0.710222 0.268379 0.360454 0.093 Uiso 0.55(2) 1 calc R . P B 2
H35D H 0.690802 0.285742 0.414800 0.093 Uiso 0.55(2) 1 calc R . P B 2
C36A C 0.5229(16) 0.2067(10) 0.3916(7) 0.118(6) Uani 0.55(2) 1 d D U P B 2
H36D H 0.447868 0.236408 0.365018 0.176 Uiso 0.55(2) 1 calc GR . P B 2
H36E H 0.462484 0.221920 0.420397 0.176 Uiso 0.55(2) 1 calc GR . P B 2
H36F H 0.588733 0.104230 0.393250 0.176 Uiso 0.55(2) 1 calc GR . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.420(3) . ?
S1 O6 1.418(3) . ?
S1 N1 1.650(3) . ?
S1 C17 1.747(4) . ?
O1 C11 1.205(5) . ?
O2 C11 1.304(5) . ?
O2 C12 1.517(7) . ?
O2 C12A 1.498(7) . ?
O3 C14 1.202(5) . ?
O4 C14 1.330(5) . ?
O4 C15 1.448(5) . ?
N1 C1 1.462(5) . ?
N1 C6 1.421(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.504(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.504(5) . ?
C2 C4 1.490(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.540(5) . ?
C3 C11 1.477(5) . ?
C4 C5 1.495(5) . ?
C4 C14 1.500(5) . ?
C5 C6 1.407(5) . ?
C5 C10 1.387(5) . ?
C6 C7 1.388(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.363(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(6) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.512(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.431(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.386(5) . ?
C17 C22 1.386(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(7) . ?
C20 C21 1.396(7) . ?
C20 C23 1.491(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(7) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
S2 O11 1.409(3) . ?
S2 O12 1.421(3) . ?
S2 N2 1.654(3) . ?
S2 C40 1.762(4) . ?
O7 C34 1.205(4) . ?
O8 C34 1.312(5) . ?
O8 C35 1.503(7) . ?
O8 C35A 1.509(7) . ?
O9 C37 1.190(5) . ?
O10 C37 1.351(5) . ?
O10 C38 1.450(5) . ?
N2 C24 1.466(5) . ?
N2 C29 1.425(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.514(5) . ?
C25 H25 0.9800 . ?
C25 C26 1.510(5) . ?
C25 C27 1.488(5) . ?
C26 H26 0.9800 . ?
C26 C27 1.542(5) . ?
C26 C34 1.481(5) . ?
C27 C28 1.496(5) . ?
C27 C37 1.501(5) . ?
C28 C29 1.397(5) . ?
C28 C33 1.393(5) . ?
C29 C30 1.396(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.366(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.363(8) . ?
C32 H32 0.9300 . ?
C32 C33 1.384(6) . ?
C33 H33 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.522(9) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.444(7) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.382(6) . ?
C40 C45 1.386(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.373(7) . ?
C42 H42 0.9300 . ?
C42 C43 1.373(7) . ?
C43 C44 1.397(7) . ?
C43 C46 1.504(7) . ?
C44 H44 0.9300 . ?
C44 C45 1.367(6) . ?
C45 H45 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A C13A 1.508(9) . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C35A H35C 0.9700 . ?
C35A H35D 0.9700 . ?
C35A C36A 1.505(9) . ?
C36A H36D 0.9600 . ?
C36A H36E 0.9600 . ?
C36A H36F 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
O5 S1 N1 105.8(2) . . ?
O5 S1 C17 107.93(19) . . ?
O6 S1 O5 119.7(2) . . ?
O6 S1 N1 107.52(18) . . ?
O6 S1 C17 107.6(2) . . ?
N1 S1 C17 107.85(16) . . ?
C11 O2 C12 108.9(5) . . ?
C11 O2 C12A 122.6(6) . . ?
C14 O4 C15 115.9(3) . . ?
C1 N1 S1 116.6(3) . . ?
C6 N1 S1 124.8(3) . . ?
C6 N1 C1 117.2(3) . . ?
N1 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
N1 C1 C2 112.4(3) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C1 C2 H2 115.4 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 115.4 . . ?
C4 C2 C1 117.3(3) . . ?
C4 C2 H2 115.4 . . ?
C4 C2 C3 61.9(2) . . ?
C2 C3 H3 116.4 . . ?
C2 C3 C4 58.6(2) . . ?
C4 C3 H3 116.4 . . ?
C11 C3 C2 117.6(3) . . ?
C11 C3 H3 116.4 . . ?
C11 C3 C4 118.9(3) . . ?
C2 C4 C3 59.5(2) . . ?
C2 C4 C5 116.8(3) . . ?
C2 C4 C14 116.8(3) . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 C14 117.0(3) . . ?
C14 C4 C3 116.5(3) . . ?
C6 C5 C4 120.4(3) . . ?
C10 C5 C4 121.5(3) . . ?
C10 C5 C6 118.0(3) . . ?
C5 C6 N1 119.0(3) . . ?
C7 C6 N1 121.2(3) . . ?
C7 C6 C5 119.5(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 H10 119.1 . . ?
C9 C10 C5 121.9(4) . . ?
C9 C10 H10 119.1 . . ?
O1 C11 O2 124.7(4) . . ?
O1 C11 C3 124.4(4) . . ?
O2 C11 C3 110.9(3) . . ?
O2 C12 H12A 111.3 . . ?
O2 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
C13 C12 O2 102.5(7) . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O4 124.3(4) . . ?
O3 C14 C4 124.5(4) . . ?
O4 C14 C4 111.2(3) . . ?
O4 C15 H15A 109.8 . . ?
O4 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 O4 109.5(4) . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S1 120.2(3) . . ?
C22 C17 S1 120.4(3) . . ?
C22 C17 C18 119.4(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.3(4) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 118.1(5) . . ?
C19 C20 C23 121.6(5) . . ?
C21 C20 C23 120.2(5) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.0(4) . . ?
C21 C22 H22 120.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O11 S2 O12 120.0(2) . . ?
O11 S2 N2 106.2(2) . . ?
O11 S2 C40 107.4(2) . . ?
O12 S2 N2 107.48(18) . . ?
O12 S2 C40 108.1(2) . . ?
N2 S2 C40 106.95(16) . . ?
C34 O8 C35 119.9(6) . . ?
C34 O8 C35A 111.0(4) . . ?
C37 O10 C38 115.4(3) . . ?
C24 N2 S2 117.3(3) . . ?
C29 N2 S2 124.7(3) . . ?
C29 N2 C24 116.6(3) . . ?
N2 C24 H24A 109.2 . . ?
N2 C24 H24B 109.2 . . ?
N2 C24 C25 112.1(3) . . ?
H24A C24 H24B 107.9 . . ?
C25 C24 H24A 109.2 . . ?
C25 C24 H24B 109.2 . . ?
C24 C25 H25 115.3 . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 115.3 . . ?
C27 C25 C24 117.5(3) . . ?
C27 C25 H25 115.3 . . ?
C27 C25 C26 61.9(2) . . ?
C25 C26 H26 116.8 . . ?
C25 C26 C27 58.4(2) . . ?
C27 C26 H26 116.8 . . ?
C34 C26 C25 117.3(3) . . ?
C34 C26 H26 116.8 . . ?
C34 C26 C27 118.0(3) . . ?
C25 C27 C26 59.7(2) . . ?
C25 C27 C28 116.4(3) . . ?
C25 C27 C37 116.8(3) . . ?
C28 C27 C26 117.8(3) . . ?
C28 C27 C37 116.7(3) . . ?
C37 C27 C26 117.2(3) . . ?
C29 C28 C27 120.6(3) . . ?
C33 C28 C27 121.0(4) . . ?
C33 C28 C29 118.3(4) . . ?
C28 C29 N2 119.6(3) . . ?
C30 C29 N2 120.4(4) . . ?
C30 C29 C28 119.7(4) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.3(4) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 119.6 . . ?
C32 C31 C30 120.7(4) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 120.1 . . ?
C31 C32 C33 119.8(4) . . ?
C33 C32 H32 120.1 . . ?
C28 C33 H33 119.5 . . ?
C32 C33 C28 121.0(4) . . ?
C32 C33 H33 119.5 . . ?
O7 C34 O8 124.2(3) . . ?
O7 C34 C26 124.7(4) . . ?
O8 C34 C26 111.0(3) . . ?
O8 C35 H35A 111.3 . . ?
O8 C35 H35B 111.3 . . ?
O8 C35 C36 102.1(7) . . ?
H35A C35 H35B 109.2 . . ?
C36 C35 H35A 111.3 . . ?
C36 C35 H35B 111.3 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O9 C37 O10 124.1(4) . . ?
O9 C37 C27 125.7(4) . . ?
O10 C37 C27 110.2(3) . . ?
O10 C38 H38A 110.0 . . ?
O10 C38 H38B 110.0 . . ?
H38A C38 H38B 108.4 . . ?
C39 C38 O10 108.5(4) . . ?
C39 C38 H38A 110.0 . . ?
C39 C38 H38B 110.0 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 S2 120.0(3) . . ?
C41 C40 C45 120.4(4) . . ?
C45 C40 S2 119.5(3) . . ?
C40 C41 H41 120.6 . . ?
C42 C41 C40 118.8(4) . . ?
C42 C41 H41 120.6 . . ?
C41 C42 H42 119.0 . . ?
C41 C42 C43 122.0(4) . . ?
C43 C42 H42 119.0 . . ?
C42 C43 C44 118.2(4) . . ?
C42 C43 C46 121.8(5) . . ?
C44 C43 C46 119.9(5) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 C43 120.7(4) . . ?
C45 C44 H44 119.6 . . ?
C40 C45 H45 120.1 . . ?
C44 C45 C40 119.7(4) . . ?
C44 C45 H45 120.1 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O2 C12A H12C 111.1 . . ?
O2 C12A H12D 111.1 . . ?
O2 C12A C13A 103.2(6) . . ?
H12C C12A H12D 109.1 . . ?
C13A C12A H12C 111.1 . . ?
C13A C12A H12D 111.1 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O8 C35A H35C 111.1 . . ?
O8 C35A H35D 111.1 . . ?
H35C C35A H35D 109.1 . . ?
C36A C35A O8 103.2(6) . . ?
C36A C35A H35C 111.1 . . ?
C36A C35A H35D 111.1 . . ?
C35A C36A H36D 109.5 . . ?
C35A C36A H36E 109.5 . . ?
C35A C36A H36F 109.5 . . ?
H36D C36A H36E 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 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
S1 N1 C1 C2 119.2(3) . . . . ?
S1 N1 C6 C5 -135.7(3) . . . . ?
S1 N1 C6 C7 49.9(5) . . . . ?
S1 C17 C18 C19 -179.8(3) . . . . ?
S1 C17 C22 C21 179.6(3) . . . . ?
O5 S1 N1 C1 38.6(3) . . . . ?
O5 S1 N1 C6 -154.8(3) . . . . ?
O5 S1 C17 C18 -18.1(4) . . . . ?
O5 S1 C17 C22 162.4(3) . . . . ?
O6 S1 N1 C1 167.6(3) . . . . ?
O6 S1 N1 C6 -25.8(4) . . . . ?
O6 S1 C17 C18 -148.5(3) . . . . ?
O6 S1 C17 C22 32.0(3) . . . . ?
N1 S1 C17 C18 95.8(3) . . . . ?
N1 S1 C17 C22 -83.7(3) . . . . ?
N1 C1 C2 C3 -37.7(5) . . . . ?
N1 C1 C2 C4 34.3(5) . . . . ?
N1 C6 C7 C8 176.7(4) . . . . ?
C1 N1 C6 C5 30.9(5) . . . . ?
C1 N1 C6 C7 -143.6(4) . . . . ?
C1 C2 C3 C4 106.6(4) . . . . ?
C1 C2 C3 C11 -144.8(4) . . . . ?
C1 C2 C4 C3 -112.3(4) . . . . ?
C1 C2 C4 C5 -4.3(5) . . . . ?
C1 C2 C4 C14 141.3(4) . . . . ?
C2 C3 C4 C5 -106.4(4) . . . . ?
C2 C3 C4 C14 106.9(4) . . . . ?
C2 C3 C11 O1 -26.3(6) . . . . ?
C2 C3 C11 O2 153.3(4) . . . . ?
C2 C4 C5 C6 -14.9(5) . . . . ?
C2 C4 C5 C10 161.7(4) . . . . ?
C2 C4 C14 O3 -46.3(6) . . . . ?
C2 C4 C14 O4 135.6(4) . . . . ?
C3 C2 C4 C5 108.0(4) . . . . ?
C3 C2 C4 C14 -106.4(4) . . . . ?
C3 C4 C5 C6 53.0(5) . . . . ?
C3 C4 C5 C10 -130.4(4) . . . . ?
C3 C4 C14 O3 -113.8(5) . . . . ?
C3 C4 C14 O4 68.2(4) . . . . ?
C4 C2 C3 C11 108.6(4) . . . . ?
C4 C3 C11 O1 41.2(6) . . . . ?
C4 C3 C11 O2 -139.2(4) . . . . ?
C4 C5 C6 N1 2.0(5) . . . . ?
C4 C5 C6 C7 176.6(4) . . . . ?
C4 C5 C10 C9 -177.5(5) . . . . ?
C5 C4 C14 O3 99.2(5) . . . . ?
C5 C4 C14 O4 -78.8(5) . . . . ?
C5 C6 C7 C8 2.2(7) . . . . ?
C6 N1 C1 C2 -48.5(5) . . . . ?
C6 C5 C10 C9 -0.9(7) . . . . ?
C6 C7 C8 C9 -3.4(8) . . . . ?
C7 C8 C9 C10 2.4(9) . . . . ?
C8 C9 C10 C5 -0.2(9) . . . . ?
C10 C5 C6 N1 -174.7(4) . . . . ?
C10 C5 C6 C7 -0.1(6) . . . . ?
C11 O2 C12 C13 -168.5(15) . . . . ?
C11 O2 C12A C13A -109.7(13) . . . . ?
C11 C3 C4 C2 -106.5(4) . . . . ?
C11 C3 C4 C5 147.2(4) . . . . ?
C11 C3 C4 C14 0.5(5) . . . . ?
C12 O2 C11 O1 -11.5(10) . . . . ?
C12 O2 C11 C3 168.9(9) . . . . ?
C14 O4 C15 C16 177.1(5) . . . . ?
C14 C4 C5 C6 -160.4(4) . . . . ?
C14 C4 C5 C10 16.1(6) . . . . ?
C15 O4 C14 O3 5.9(7) . . . . ?
C15 O4 C14 C4 -176.1(4) . . . . ?
C17 S1 N1 C1 -76.7(3) . . . . ?
C17 S1 N1 C6 89.9(3) . . . . ?
C17 C18 C19 C20 -0.2(7) . . . . ?
C18 C17 C22 C21 0.0(6) . . . . ?
C18 C19 C20 C21 0.7(7) . . . . ?
C18 C19 C20 C23 -179.1(5) . . . . ?
C19 C20 C21 C22 -0.9(7) . . . . ?
C20 C21 C22 C17 0.5(6) . . . . ?
C22 C17 C18 C19 -0.2(6) . . . . ?
C23 C20 C21 C22 178.9(5) . . . . ?
S2 N2 C24 C25 -118.3(3) . . . . ?
S2 N2 C29 C28 135.0(3) . . . . ?
S2 N2 C29 C30 -51.4(5) . . . . ?
S2 C40 C41 C42 -179.9(3) . . . . ?
S2 C40 C45 C44 178.1(3) . . . . ?
O11 S2 N2 C24 -42.4(3) . . . . ?
O11 S2 N2 C29 151.8(3) . . . . ?
O11 S2 C40 C41 -150.9(3) . . . . ?
O11 S2 C40 C45 30.8(4) . . . . ?
O12 S2 N2 C24 -172.1(3) . . . . ?
O12 S2 N2 C29 22.1(4) . . . . ?
O12 S2 C40 C41 -20.0(4) . . . . ?
O12 S2 C40 C45 161.7(3) . . . . ?
N2 S2 C40 C41 95.4(3) . . . . ?
N2 S2 C40 C45 -82.9(3) . . . . ?
N2 C24 C25 C26 37.5(5) . . . . ?
N2 C24 C25 C27 -34.6(5) . . . . ?
N2 C29 C30 C31 -176.8(4) . . . . ?
C24 N2 C29 C28 -30.8(5) . . . . ?
C24 N2 C29 C30 142.7(4) . . . . ?
C24 C25 C26 C27 -106.8(4) . . . . ?
C24 C25 C26 C34 145.5(3) . . . . ?
C24 C25 C27 C26 112.3(4) . . . . ?
C24 C25 C27 C28 4.1(5) . . . . ?
C24 C25 C27 C37 -140.3(4) . . . . ?
C25 C26 C27 C28 106.0(4) . . . . ?
C25 C26 C27 C37 -106.7(3) . . . . ?
C25 C26 C34 O7 22.4(6) . . . . ?
C25 C26 C34 O8 -158.2(3) . . . . ?
C25 C27 C28 C29 15.7(5) . . . . ?
C25 C27 C28 C33 -161.6(4) . . . . ?
C25 C27 C37 O9 45.8(6) . . . . ?
C25 C27 C37 O10 -134.4(3) . . . . ?
C26 C25 C27 C28 -108.2(3) . . . . ?
C26 C25 C27 C37 107.4(4) . . . . ?
C26 C27 C28 C29 -52.3(5) . . . . ?
C26 C27 C28 C33 130.4(4) . . . . ?
C26 C27 C37 O9 113.8(5) . . . . ?
C26 C27 C37 O10 -66.4(4) . . . . ?
C27 C25 C26 C34 -107.6(4) . . . . ?
C27 C26 C34 O7 -44.4(5) . . . . ?
C27 C26 C34 O8 135.0(4) . . . . ?
C27 C28 C29 N2 -2.7(6) . . . . ?
C27 C28 C29 C30 -176.3(4) . . . . ?
C27 C28 C33 C32 177.9(4) . . . . ?
C28 C27 C37 O9 -98.5(5) . . . . ?
C28 C27 C37 O10 81.3(4) . . . . ?
C28 C29 C30 C31 -3.3(7) . . . . ?
C29 N2 C24 C25 48.6(5) . . . . ?
C29 C28 C33 C32 0.6(7) . . . . ?
C29 C30 C31 C32 3.9(8) . . . . ?
C30 C31 C32 C33 -2.3(9) . . . . ?
C31 C32 C33 C28 0.0(8) . . . . ?
C33 C28 C29 N2 174.6(4) . . . . ?
C33 C28 C29 C30 1.0(6) . . . . ?
C34 O8 C35 C36 124.5(13) . . . . ?
C34 O8 C35A C36A 174.8(12) . . . . ?
C34 C26 C27 C25 106.4(3) . . . . ?
C34 C26 C27 C28 -147.6(3) . . . . ?
C34 C26 C27 C37 -0.3(5) . . . . ?
C35 O8 C34 O7 -19.8(9) . . . . ?
C35 O8 C34 C26 160.8(7) . . . . ?
C37 O10 C38 C39 -178.3(5) . . . . ?
C37 C27 C28 C29 160.2(4) . . . . ?
C37 C27 C28 C33 -17.1(5) . . . . ?
C38 O10 C37 O9 -4.7(6) . . . . ?
C38 O10 C37 C27 175.5(4) . . . . ?
C40 S2 N2 C24 72.0(3) . . . . ?
C40 S2 N2 C29 -93.7(3) . . . . ?
C40 C41 C42 C43 2.4(7) . . . . ?
C41 C40 C45 C44 -0.2(6) . . . . ?
C41 C42 C43 C44 -1.3(7) . . . . ?
C41 C42 C43 C46 -177.6(5) . . . . ?
C42 C43 C44 C45 -0.6(6) . . . . ?
C43 C44 C45 C40 1.3(6) . . . . ?
C45 C40 C41 C42 -1.6(6) . . . . ?
C46 C43 C44 C45 175.8(4) . . . . ?
C12A O2 C11 O1 14.3(8) . . . . ?
C12A O2 C11 C3 -165.3(6) . . . . ?
C35A O8 C34 O7 12.4(8) . . . . ?
C35A O8 C34 C26 -167.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.919
_oxdiff_exptl_absorpt_empirical_full_min 0.507
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.894(3)
2 0.106(3)

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1947443'
loop_
_audit_author_name
_audit_author_address
'Jiayong Zhang'
;nankai university
China
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H N5 O S'
_chemical_formula_weight         371.33

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.0259(12)
_cell_length_b                   12.569(3)
_cell_length_c                   12.930(3)
_cell_angle_alpha                115.34(3)
_cell_angle_beta                 93.96(3)
_cell_angle_gamma                100.21(3)
_cell_volume                     859.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2334
_cell_measurement_theta_min      1.7664
_cell_measurement_theta_max      27.8904

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4708
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10454
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         27.900
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4067
_reflns_number_gt                2143
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0687P)²] 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_number_reflns         4067
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.005
_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
S1 S 0.39841(12) 1.06140(6) 0.86614(5) 0.0222(2) Uani 1 1 d . . . . .
O1 O 0.3000(4) 1.12211(16) 0.96699(15) 0.0312(5) Uani 1 1 d . . . . .
O2 O 0.6412(3) 1.07310(17) 0.87811(16) 0.0312(5) Uani 1 1 d . . . . .
O3 O 0.4834(3) 0.86053(17) 0.67040(15) 0.0263(5) Uani 1 1 d . . . . .
O4 O 0.4895(4) 0.55809(16) 0.83356(18) 0.0347(5) Uani 1 1 d . . . . .
O5 O 0.1820(4) 0.45025(18) 0.6983(2) 0.0511(7) Uani 1 1 d . . . . .
N1 N 0.2684(4) 0.91511(18) 0.81484(17) 0.0183(5) Uani 1 1 d . . . . .
C1 C 0.3107(4) 1.1034(2) 0.7600(2) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.1100(5) 1.1432(2) 0.7627(2) 0.0242(6) Uani 1 1 d . . . . .
H2 H 0.022456 1.150578 0.822772 0.029 Uiso 1 1 calc R U . . .
C3 C 0.0400(5) 1.1721(2) 0.6748(2) 0.0246(6) Uani 1 1 d . . . . .
H3 H -0.095327 1.201355 0.676587 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1620(4) 1.1593(2) 0.5848(2) 0.0202(6) Uani 1 1 d . . . . .
C5 C 0.3649(5) 1.1218(2) 0.5864(2) 0.0239(6) Uani 1 1 d . . . . .
H5 H 0.453336 1.115226 0.526756 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4411(5) 1.0936(2) 0.6733(2) 0.0207(6) Uani 1 1 d . . . . .
H6 H 0.580270 1.068001 0.673432 0.025 Uiso 1 1 calc R U . . .
C7 C 0.0809(5) 1.1874(3) 0.4899(2) 0.0318(7) Uani 1 1 d . . . . .
H7A H 0.095012 1.274763 0.520567 0.048 Uiso 1 1 calc R U . . .
H7B H -0.079527 1.145146 0.458427 0.048 Uiso 1 1 calc R U . . .
H7C H 0.173734 1.160640 0.428250 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3444(4) 0.8292(2) 0.7222(2) 0.0203(6) Uani 1 1 d . . . . .
C9 C 0.2503(5) 0.6992(2) 0.6893(2) 0.0214(6) Uani 1 1 d . . . . .
C10 C 0.2504(5) 0.6656(2) 0.7912(2) 0.0231(6) Uani 1 1 d . . . . .
H10 H 0.309371 0.732848 0.870847 0.028 Uiso 1 1 calc R U . . .
C11 C 0.0307(5) 0.6671(2) 0.7295(2) 0.0229(6) Uani 1 1 d . . . . .
H11 H -0.069705 0.585862 0.677072 0.027 Uiso 1 1 calc R U . . .
C12 C -0.0914(4) 0.7658(2) 0.7863(2) 0.0224(6) Uani 1 1 d . . . . .
H12A H -0.201700 0.741010 0.829604 0.027 Uiso 1 1 calc R U . . .
H12B H -0.179178 0.776952 0.725494 0.027 Uiso 1 1 calc R U . . .
C13 C 0.0679(4) 0.8847(2) 0.8683(2) 0.0207(6) Uani 1 1 d . . . . .
H13A H -0.016907 0.949724 0.890021 0.025 Uiso 1 1 calc R U . . .
H13B H 0.124140 0.880458 0.939916 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3042(5) 0.6143(3) 0.5739(2) 0.0319(7) Uani 1 1 d . . . . .
H14A H 0.246611 0.634172 0.513136 0.048 Uiso 1 1 calc R U . . .
H14B H 0.230923 0.530706 0.555064 0.048 Uiso 1 1 calc R U . . .
H14C H 0.470045 0.623173 0.578786 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2973(5) 0.5457(3) 0.7672(2) 0.0295(7) Uani 1 1 d . . . . .
C16 C 0.5620(6) 0.4470(3) 0.8124(3) 0.0485(9) Uani 1 1 d . . . . .
H16A H 0.436047 0.388074 0.817663 0.058 Uiso 1 1 calc R U . . .
H16B H 0.602403 0.410664 0.733710 0.058 Uiso 1 1 calc R U . . .
C17 C 0.7574(7) 0.4753(3) 0.8980(3) 0.0613(11) Uani 1 1 d . . . . .
H17A H 0.876175 0.539029 0.897091 0.092 Uiso 1 1 calc R U . . .
H17B H 0.816954 0.402774 0.880247 0.092 Uiso 1 1 calc R U . . .
H17C H 0.712097 0.503291 0.974989 0.092 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
S1 O1 1.432(2) . ?
S1 O2 1.435(2) . ?
S1 N1 1.676(2) . ?
S1 C1 1.750(2) . ?
O3 C8 1.222(3) . ?
O4 C15 1.337(3) . ?
O4 C16 1.456(3) . ?
O5 C15 1.192(3) . ?
N1 C8 1.398(3) . ?
N1 C13 1.503(3) . ?
C1 C2 1.385(4) . ?
C1 C6 1.389(4) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 C7 1.489(3) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.488(4) . ?
C9 C11 1.507(4) . ?
C9 C14 1.516(4) . ?
C9 C10 1.546(4) . ?
C10 C15 1.486(4) . ?
C10 C11 1.505(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.496(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.508(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.440(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O1 S1 O2 118.93(13) . . ?
O1 S1 N1 104.59(12) . . ?
O2 S1 N1 109.01(12) . . ?
O1 S1 C1 108.65(12) . . ?
O2 S1 C1 109.45(12) . . ?
N1 S1 C1 105.31(11) . . ?
C15 O4 C16 116.1(2) . . ?
C8 N1 C13 123.7(2) . . ?
C8 N1 S1 118.78(18) . . ?
C13 N1 S1 117.46(17) . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 S1 119.4(2) . . ?
C6 C1 S1 119.2(2) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 C7 121.1(3) . . ?
C5 C4 C7 120.6(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 N1 120.7(2) . . ?
O3 C8 C9 121.5(2) . . ?
N1 C8 C9 117.8(2) . . ?
C8 C9 C11 117.5(2) . . ?
C8 C9 C14 113.3(2) . . ?
C11 C9 C14 120.8(2) . . ?
C8 C9 C10 115.3(2) . . ?
C11 C9 C10 59.05(17) . . ?
C14 C9 C10 120.4(2) . . ?
C15 C10 C11 117.6(2) . . ?
C15 C10 C9 116.3(2) . . ?
C11 C10 C9 59.17(17) . . ?
C15 C10 H10 117.1 . . ?
C11 C10 H10 117.1 . . ?
C9 C10 H10 117.1 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 C9 117.4(2) . . ?
C10 C11 C9 61.78(18) . . ?
C12 C11 H11 115.4 . . ?
C10 C11 H11 115.4 . . ?
C9 C11 H11 115.4 . . ?
C11 C12 C13 113.0(2) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N1 C13 C12 111.7(2) . . ?
N1 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 O4 123.4(3) . . ?
O5 C15 C10 125.6(3) . . ?
O4 C15 C10 111.0(2) . . ?
C17 C16 O4 108.7(3) . . ?
C17 C16 H16A 110.0 . . ?
O4 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
O4 C16 H16B 110.0 . . ?
H16A C16 H16B 108.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 S1 N1 C8 -173.39(18) . . . . ?
O2 S1 N1 C8 -45.2(2) . . . . ?
C1 S1 N1 C8 72.2(2) . . . . ?
O1 S1 N1 C13 9.4(2) . . . . ?
O2 S1 N1 C13 137.60(18) . . . . ?
C1 S1 N1 C13 -105.05(19) . . . . ?
O1 S1 C1 C2 -24.4(2) . . . . ?
O2 S1 C1 C2 -155.8(2) . . . . ?
N1 S1 C1 C2 87.2(2) . . . . ?
O1 S1 C1 C6 157.0(2) . . . . ?
O2 S1 C1 C6 25.6(2) . . . . ?
N1 S1 C1 C6 -91.4(2) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
S1 C1 C2 C3 -177.81(19) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C2 C3 C4 C5 -2.9(4) . . . . ?
C2 C3 C4 C7 178.2(2) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
C7 C4 C5 C6 -179.0(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
S1 C1 C6 C5 177.05(19) . . . . ?
C13 N1 C8 O3 168.2(2) . . . . ?
S1 N1 C8 O3 -8.8(3) . . . . ?
C13 N1 C8 C9 -11.7(3) . . . . ?
S1 N1 C8 C9 171.24(17) . . . . ?
O3 C8 C9 C11 -160.8(2) . . . . ?
N1 C8 C9 C11 19.2(3) . . . . ?
O3 C8 C9 C14 -12.1(3) . . . . ?
N1 C8 C9 C14 167.9(2) . . . . ?
O3 C8 C9 C10 132.5(3) . . . . ?
N1 C8 C9 C10 -47.5(3) . . . . ?
C8 C9 C10 C15 -143.9(3) . . . . ?
C11 C9 C10 C15 107.8(3) . . . . ?
C14 C9 C10 C15 -2.1(4) . . . . ?
C8 C9 C10 C11 108.2(3) . . . . ?
C14 C9 C10 C11 -109.9(3) . . . . ?
C15 C10 C11 C12 147.5(3) . . . . ?
C9 C10 C11 C12 -106.7(3) . . . . ?
C15 C10 C11 C9 -105.7(3) . . . . ?
C8 C9 C11 C12 7.6(3) . . . . ?
C14 C9 C11 C12 -138.7(2) . . . . ?
C10 C9 C11 C12 112.1(3) . . . . ?
C8 C9 C11 C10 -104.5(2) . . . . ?
C14 C9 C11 C10 109.3(3) . . . . ?
C10 C11 C12 C13 30.7(3) . . . . ?
C9 C11 C12 C13 -41.1(3) . . . . ?
C8 N1 C13 C12 -21.8(3) . . . . ?
S1 N1 C13 C12 155.24(17) . . . . ?
C11 C12 C13 N1 47.0(3) . . . . ?
C16 O4 C15 O5 3.8(5) . . . . ?
C16 O4 C15 C10 -176.0(3) . . . . ?
C11 C10 C15 O5 4.5(5) . . . . ?
C9 C10 C15 O5 -62.8(4) . . . . ?
C11 C10 C15 O4 -175.7(2) . . . . ?
C9 C10 C15 O4 117.0(3) . . . . ?
C15 O4 C16 C17 -174.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13B O2 0.99 2.44 3.390(3) 160.9 2_677 yes
C12 H12B O3 0.99 2.64 3.508(3) 147.1 1_455 yes
C12 H12A O1 0.99 2.63 3.328(3) 127.4 2_577 yes
C2 H2 O2 0.95 2.60 3.436(3) 146.8 1_455 yes

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.117

