# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
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data_22019573_0m
_database_code_depnum_ccdc_archive 'CCDC 2027384'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-05-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        colchicine
_chemical_formula_moiety         'C6 H5 O3 S, C22 H26 N O6'
_chemical_formula_sum            'C28 H31 N O9 S'
_chemical_formula_weight         557.60
_chemical_absolute_configuration .
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.7125(6)
_cell_length_b                   8.0135(3)
_cell_length_c                   12.9098(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.920(2)
_cell_angle_gamma                90
_cell_volume                     1314.40(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6178
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1109 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14806
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.405
_diffrn_reflns_theta_min         2.287
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                4273
_reflns_number_total             4842
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1529 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.080
_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)+(0.0349P)²+0.4639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C6(H6a,H6b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4a), C11(H11), C12(H12), C24(H24), C8(H8), C23(H23), C20(H20),
 C22(H22), C21(H21)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C13(H13a,H13b,H13c), C17(H17a,H17b,
 H17c), C18(H18a,H18b,H18c)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.76938(7) 0.11138(12) 0.64412(7) 0.0252(2) Uani 1 1 d . . . . .
O2 O 0.04893(18) 0.5814(3) 0.96168(18) 0.0224(6) Uani 1 1 d . . . . .
O1 O 0.12322(18) 0.3421(3) 0.82098(18) 0.0216(5) Uani 1 1 d . . . . .
O3 O 0.16132(18) 0.8556(3) 1.00183(19) 0.0223(5) Uani 1 1 d . . . . .
O5 O 0.32565(19) 0.1065(4) 0.41003(17) 0.0262(6) Uani 1 1 d . . . . .
O6 O 0.45596(19) 0.0802(3) 0.93183(19) 0.0263(6) Uani 1 1 d . . . . .
O4 O 0.4974(2) 0.0610(3) 0.5045(2) 0.0284(6) Uani 1 1 d . . . . .
H4 H 0.5534 0.0500 0.5402 0.043 Uiso 1 1 calc GR . . . .
O9 O 0.8545(2) 0.0041(4) 0.6796(2) 0.0296(6) Uani 1 1 d . . . . .
O8 O 0.7469(2) 0.2467(4) 0.71537(19) 0.0299(6) Uani 1 1 d . . . . .
O7 O 0.6737(2) 0.0171(4) 0.6147(2) 0.0287(6) Uani 1 1 d . . . . .
N1 N 0.5623(2) 0.2521(4) 0.8443(2) 0.0195(6) Uani 1 1 d . . . . .
H1 H 0.6267 0.2741 0.8255 0.023 Uiso 1 1 calc R . . . .
C12B C 0.2746(3) 0.5078(5) 0.7947(2) 0.0178(7) Uani 1 1 d . . . . .
C3 C 0.2025(3) 0.7476(5) 0.9328(3) 0.0203(7) Uani 1 1 d . . . . .
C16 C 0.5427(3) 0.1089(5) 0.8952(2) 0.0208(7) Uani 1 1 d . . . . .
C7 C 0.4789(3) 0.3701(5) 0.8202(2) 0.0186(7) Uani 1 1 d . . . . .
H7 H 0.4311 0.3712 0.8802 0.022 Uiso 1 1 calc R . . . .
C1 C 0.1771(3) 0.4869(4) 0.8420(3) 0.0186(7) Uani 1 1 d . . . . .
C7A C 0.4119(3) 0.3220(4) 0.7232(3) 0.0185(7) Uani 1 1 d . . . . .
C10 C 0.3312(3) 0.1809(5) 0.5026(3) 0.0236(8) Uani 1 1 d . . . . .
C4 C 0.2992(3) 0.7687(5) 0.8866(3) 0.0190(7) Uani 1 1 d . . . . .
H4A H 0.3403 0.8653 0.9016 0.023 Uiso 1 1 calc R . . . .
C11 C 0.2476(3) 0.2691(5) 0.5410(3) 0.0214(8) Uani 1 1 d . . . . .
H11 H 0.1858 0.2678 0.4976 0.026 Uiso 1 1 calc R . . . .
C12 C 0.2385(3) 0.3594(5) 0.6320(2) 0.0201(7) Uani 1 1 d . . . . .
H12 H 0.1717 0.4106 0.6395 0.024 Uiso 1 1 calc R . . . .
C2 C 0.1422(2) 0.6049(5) 0.9126(2) 0.0187(7) Uani 1 1 d . . . . .
C12A C 0.3103(3) 0.3885(5) 0.7150(3) 0.0193(7) Uani 1 1 d . . . . .
C9 C 0.4303(3) 0.1562(5) 0.5556(3) 0.0230(8) Uani 1 1 d . . . . .
C5 C 0.4405(3) 0.6713(5) 0.7685(3) 0.0206(8) Uani 1 1 d . . . . .
H5A H 0.4665 0.7860 0.7819 0.025 Uiso 1 1 calc R . . . .
H5B H 0.4306 0.6577 0.6925 0.025 Uiso 1 1 calc R . . . .
C24 C 0.7383(3) 0.2865(5) 0.4633(3) 0.0270(9) Uani 1 1 d . . . . .
H24 H 0.6661 0.2889 0.4801 0.032 Uiso 1 1 calc R . . . .
C8 C 0.4606(3) 0.2205(5) 0.6518(3) 0.0213(8) Uani 1 1 d . . . . .
H8 H 0.5298 0.1883 0.6736 0.026 Uiso 1 1 calc R . . . .
C4A C 0.3358(3) 0.6489(5) 0.8188(3) 0.0186(7) Uani 1 1 d . . . . .
C6 C 0.5230(3) 0.5459(5) 0.8090(3) 0.0213(8) Uani 1 1 d . . . . .
H6A H 0.5820 0.5429 0.7608 0.026 Uiso 1 1 calc R . . . .
H6B H 0.5514 0.5842 0.8772 0.026 Uiso 1 1 calc R . . . .
C14 C 0.0649(3) 0.5046(6) 1.0618(3) 0.0284(9) Uani 1 1 d . . . . .
H14A H 0.0870 0.3884 1.0530 0.043 Uiso 1 1 calc GR . . . .
H14B H -0.0010 0.5075 1.0991 0.043 Uiso 1 1 calc GR . . . .
H14C H 0.1195 0.5655 1.1016 0.043 Uiso 1 1 calc GR . . . .
C15 C 0.2137(3) 1.0128(5) 1.0164(3) 0.0271(8) Uani 1 1 d . . . . .
H15A H 0.2193 1.0688 0.9493 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.2843 0.9940 1.0470 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.1733 1.0829 1.0629 0.041 Uiso 1 1 calc GR . . . .
C23 C 0.7711(3) 0.3633(5) 0.3734(3) 0.0275(8) Uani 1 1 d . . . . .
H23 H 0.7213 0.4174 0.3283 0.033 Uiso 1 1 calc R . . . .
C20 C 0.9169(3) 0.2033(5) 0.5038(3) 0.0290(9) Uani 1 1 d . . . . .
H20 H 0.9670 0.1484 0.5482 0.035 Uiso 1 1 calc R . . . .
C13 C 0.0129(3) 0.3579(6) 0.7911(3) 0.0290(9) Uani 1 1 d . . . . .
H13A H -0.0093 0.2607 0.7498 0.043 Uiso 1 1 calc GR . . . .
H13B H 0.0022 0.4596 0.7498 0.043 Uiso 1 1 calc GR . . . .
H13C H -0.0290 0.3644 0.8533 0.043 Uiso 1 1 calc GR . . . .
C17 C 0.6322(3) -0.0133(5) 0.9050(3) 0.0276(9) Uani 1 1 d . . . . .
H17A H 0.6861 0.0303 0.9539 0.041 Uiso 1 1 calc GR . . . .
H17B H 0.6628 -0.0295 0.8371 0.041 Uiso 1 1 calc GR . . . .
H17C H 0.6060 -0.1202 0.9305 0.041 Uiso 1 1 calc GR . . . .
C19 C 0.8115(3) 0.2061(5) 0.5286(3) 0.0249(8) Uani 1 1 d . . . . .
C22 C 0.8761(3) 0.3609(6) 0.3496(3) 0.0304(9) Uani 1 1 d . . . . .
H22 H 0.8984 0.4147 0.2885 0.037 Uiso 1 1 calc R . . . .
C18 C 0.2249(3) 0.1136(6) 0.3476(3) 0.0313(9) Uani 1 1 d . . . . .
H18A H 0.2313 0.0466 0.2846 0.047 Uiso 1 1 calc GR . . . .
H18B H 0.2094 0.2296 0.3286 0.047 Uiso 1 1 calc GR . . . .
H18C H 0.1677 0.0692 0.3886 0.047 Uiso 1 1 calc GR . . . .
C21 C 0.9489(3) 0.2809(6) 0.4139(3) 0.0317(10) Uani 1 1 d . . . . .
H21 H 1.0210 0.2789 0.3967 0.038 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
S1 O9 1.445(3) . ?
S1 O8 1.456(3) . ?
S1 O7 1.470(3) . ?
S1 C19 1.772(4) . ?
O2 C2 1.376(4) . ?
O2 C14 1.440(4) . ?
O1 C1 1.370(4) . ?
O1 C13 1.448(4) . ?
O3 C3 1.360(4) . ?
O3 C15 1.435(5) . ?
O5 C10 1.335(4) . ?
O5 C18 1.492(4) . ?
O6 C16 1.236(4) . ?
O4 H4 0.8400 . ?
O4 C9 1.335(4) . ?
N1 H1 0.8800 . ?
N1 C16 1.350(5) . ?
N1 C7 1.447(4) . ?
C12B C1 1.409(5) . ?
C12B C12A 1.487(5) . ?
C12B C4A 1.402(5) . ?
C3 C4 1.394(5) . ?
C3 C2 1.396(5) . ?
C16 C17 1.503(5) . ?
C7 H7 1.0000 . ?
C7 C7A 1.540(5) . ?
C7 C6 1.526(5) . ?
C1 C2 1.396(5) . ?
C7A C12A 1.399(5) . ?
C7A C8 1.390(5) . ?
C10 C11 1.382(5) . ?
C10 C9 1.427(5) . ?
C4 H4A 0.9500 . ?
C4 C4A 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(5) . ?
C12 H12 0.9500 . ?
C12 C12A 1.403(5) . ?
C9 C8 1.387(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4A 1.511(5) . ?
C5 C6 1.532(5) . ?
C24 H24 0.9500 . ?
C24 C23 1.390(6) . ?
C24 C19 1.394(5) . ?
C8 H8 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C22 1.380(5) . ?
C20 H20 0.9500 . ?
C20 C19 1.388(5) . ?
C20 C21 1.389(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C21 1.381(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 H21 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
O9 S1 O8 113.80(17) . . ?
O9 S1 O7 112.35(17) . . ?
O9 S1 C19 106.09(17) . . ?
O8 S1 O7 111.56(16) . . ?
O8 S1 C19 106.48(18) . . ?
O7 S1 C19 105.89(16) . . ?
C2 O2 C14 112.0(3) . . ?
C1 O1 C13 116.9(3) . . ?
C3 O3 C15 117.2(3) . . ?
C10 O5 C18 119.0(3) . . ?
C9 O4 H4 109.5 . . ?
C16 N1 H1 119.5 . . ?
C16 N1 C7 120.9(3) . . ?
C7 N1 H1 119.5 . . ?
C1 C12B C12A 121.1(3) . . ?
C4A C12B C1 119.3(3) . . ?
C4A C12B C12A 119.5(3) . . ?
O3 C3 C4 124.6(3) . . ?
O3 C3 C2 115.0(3) . . ?
C4 C3 C2 120.4(3) . . ?
O6 C16 N1 121.8(3) . . ?
O6 C16 C17 121.9(3) . . ?
N1 C16 C17 116.3(3) . . ?
N1 C7 H7 107.4 . . ?
N1 C7 C7A 113.1(3) . . ?
N1 C7 C6 110.8(3) . . ?
C7A C7 H7 107.4 . . ?
C6 C7 H7 107.4 . . ?
C6 C7 C7A 110.4(3) . . ?
O1 C1 C12B 117.1(3) . . ?
O1 C1 C2 122.4(3) . . ?
C2 C1 C12B 120.4(3) . . ?
C12A C7A C7 116.7(3) . . ?
C8 C7A C7 116.1(3) . . ?
C8 C7A C12A 127.2(3) . . ?
O5 C10 C11 122.1(3) . . ?
O5 C10 C9 112.7(3) . . ?
C11 C10 C9 125.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C4A C4 C3 120.3(3) . . ?
C4A C4 H4A 119.9 . . ?
C10 C11 H11 114.5 . . ?
C10 C11 C12 131.1(4) . . ?
C12 C11 H11 114.5 . . ?
C11 C12 H12 114.3 . . ?
C11 C12 C12A 131.4(3) . . ?
C12A C12 H12 114.3 . . ?
O2 C2 C3 120.2(3) . . ?
O2 C2 C1 120.4(3) . . ?
C1 C2 C3 119.5(3) . . ?
C7A C12A C12B 119.7(3) . . ?
C7A C12A C12 124.8(3) . . ?
C12 C12A C12B 115.4(3) . . ?
O4 C9 C10 114.3(3) . . ?
O4 C9 C8 119.4(3) . . ?
C8 C9 C10 126.3(3) . . ?
H5A C5 H5B 107.9 . . ?
C4A C5 H5A 109.2 . . ?
C4A C5 H5B 109.2 . . ?
C4A C5 C6 112.2(3) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C19 119.8(3) . . ?
C19 C24 H24 120.1 . . ?
C7A C8 H8 113.0 . . ?
C9 C8 C7A 134.0(3) . . ?
C9 C8 H8 113.0 . . ?
C12B C4A C5 119.4(3) . . ?
C4 C4A C12B 120.1(3) . . ?
C4 C4A C5 120.5(3) . . ?
C7 C6 C5 112.9(3) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 C24 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C24 C19 S1 119.5(3) . . ?
C20 C19 S1 120.6(3) . . ?
C20 C19 C24 119.9(3) . . ?
C23 C22 H22 119.8 . . ?
C23 C22 C21 120.5(4) . . ?
C21 C22 H22 119.8 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22019951_0m
_database_code_depnum_ccdc_archive 'CCDC 2027391'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 O3 S, C10 H13 O2, H2 O'
_chemical_formula_sum            'C20 H22 O6 S'
_chemical_formula_weight         390.43
_chemical_absolute_configuration ?
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   9.2402(4)
_cell_length_b                   31.6946(17)
_cell_length_c                   6.4645(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.052(2)
_cell_angle_gamma                90
_cell_volume                     1858.11(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4540
_cell_measurement_temperature    180
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0875 before and 0.0497 after correction. The Ratio of minimum to maximum transmission is 0.9392. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11234
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.336
_diffrn_ambient_temperature      180.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.729
_reflns_number_gt                3381
_reflns_number_total             3687
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.174
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.066
_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)+(0.0296P)²+0.4961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0713
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C8(H8)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C13(H13), C5(H5), C6(H6), C11(H11), C7(H7), C19(H19), C17(H17),
 C14(H14), C18(H18), C16(H16)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.67103(8) 0.39780(2) 0.54346(11) 0.02859(17) Uani 1 1 d . . . . .
O1 O 0.2757(2) 0.43422(6) 0.3840(3) 0.0249(4) Uani 1 1 d . . . . .
H1 H 0.3681 0.4323 0.4047 0.037 Uiso 1 1 calc GR . . . .
O2 O 0.48357(19) 0.48843(6) 0.4623(3) 0.0249(4) Uani 1 1 d . . . . .
H2 H 0.5466 0.5073 0.5024 0.037 Uiso 1 1 calc GR . . . .
O5 O 0.7589(2) 0.42981(6) 0.4654(3) 0.0362(5) Uani 1 1 d . . . . .
O6 O 0.6999(2) 0.53691(6) 0.5676(3) 0.0313(5) Uani 1 1 d . . . . .
H6A H 0.7126 0.5493 0.6897 0.047 Uiso 1 1 d G . . . .
H6B H 0.7021 0.5556 0.4697 0.047 Uiso 1 1 d G . . . .
O3 O 0.5253(2) 0.39341(6) 0.4107(4) 0.0392(5) Uani 1 1 d . . . . .
O4 O 0.6673(3) 0.40225(7) 0.7655(4) 0.0517(7) Uani 1 1 d . . . . .
C1 C 0.2368(3) 0.47462(8) 0.3727(4) 0.0206(6) Uani 1 1 d . . . . .
C2 C 0.3508(3) 0.50572(8) 0.4162(4) 0.0201(5) Uani 1 1 d . . . . .
C3 C 0.3340(3) 0.54950(8) 0.4187(4) 0.0206(5) Uani 1 1 d . . . . .
H3 H 0.4239 0.5647 0.4546 0.025 Uiso 1 1 calc R . . . .
C13 C 0.8256(3) 0.34286(9) 0.3407(5) 0.0310(6) Uani 1 1 d . . . . .
H13 H 0.8197 0.3643 0.2367 0.037 Uiso 1 1 calc R . . . .
C5 C 0.0642(3) 0.56074(9) 0.3136(4) 0.0261(6) Uani 1 1 d . . . . .
H5 H -0.0083 0.5823 0.2844 0.031 Uiso 1 1 calc R . . . .
C6 C 0.0111(3) 0.51995(9) 0.2860(4) 0.0265(6) Uani 1 1 d . . . . .
H6 H -0.0924 0.5175 0.2387 0.032 Uiso 1 1 calc R . . . .
C11 C 0.7702(3) 0.31897(9) 0.6716(5) 0.0267(6) Uani 1 1 d . . . . .
H11 H 0.7278 0.3240 0.7920 0.032 Uiso 1 1 calc R . . . .
C12 C 0.7624(3) 0.34924(8) 0.5200(4) 0.0248(6) Uani 1 1 d . . . . .
C7 C 0.0871(3) 0.48195(9) 0.3175(4) 0.0236(6) Uani 1 1 d . . . . .
H7 H 0.0271 0.4574 0.2982 0.028 Uiso 1 1 calc R . . . .
C20 C 0.8413(3) 0.27995(9) 0.6504(5) 0.0282(6) Uani 1 1 d . . . . .
C9 C 0.1283(3) 0.64282(10) 0.5287(5) 0.0364(7) Uani 1 1 d . . . . .
H9A H 0.0271 0.6397 0.4501 0.055 Uiso 1 1 calc GR . . . .
H9B H 0.1523 0.6729 0.5483 0.055 Uiso 1 1 calc GR . . . .
H9C H 0.1372 0.6292 0.6667 0.055 Uiso 1 1 calc GR . . . .
C8 C 0.2341(3) 0.62220(8) 0.4068(5) 0.0271(6) Uani 1 1 d . . . . .
H8 H 0.3365 0.6264 0.4887 0.032 Uiso 1 1 calc R . . . .
C4 C 0.2083(3) 0.57484(8) 0.3778(4) 0.0232(6) Uani 1 1 d . . . . .
C15 C 0.9047(3) 0.27347(9) 0.4699(5) 0.0292(6) Uani 1 1 d . . . . .
C19 C 0.8531(3) 0.24759(10) 0.8034(5) 0.0386(8) Uani 1 1 d . . . . .
H19 H 0.8097 0.2514 0.9239 0.046 Uiso 1 1 calc R . . . .
C17 C 0.9885(4) 0.20472(10) 0.6016(6) 0.0439(9) Uani 1 1 d . . . . .
H17 H 1.0390 0.1791 0.5871 0.053 Uiso 1 1 calc R . . . .
C14 C 0.8950(3) 0.30580(10) 0.3174(5) 0.0344(7) Uani 1 1 d . . . . .
H14 H 0.9377 0.3016 0.1965 0.041 Uiso 1 1 calc R . . . .
C18 C 0.9257(4) 0.21110(10) 0.7805(6) 0.0455(9) Uani 1 1 d . . . . .
H18 H 0.9340 0.1899 0.8858 0.055 Uiso 1 1 calc R . . . .
C10 C 0.2243(4) 0.64378(10) 0.1927(5) 0.0454(9) Uani 1 1 d . . . . .
H10A H 0.1264 0.6389 0.1062 0.068 Uiso 1 1 calc GR . . . .
H10B H 0.2998 0.6321 0.1213 0.068 Uiso 1 1 calc GR . . . .
H10C H 0.2403 0.6742 0.2137 0.068 Uiso 1 1 calc GR . . . .
C16 C 0.9782(3) 0.23461(10) 0.4493(6) 0.0403(8) Uani 1 1 d . . . . .
H16 H 1.0201 0.2296 0.3284 0.048 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
S1 O5 1.450(2) . ?
S1 O3 1.458(2) . ?
S1 O4 1.449(2) . ?
S1 C12 1.776(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.328(3) . ?
O2 H2 0.8400 . ?
O2 C2 1.325(3) . ?
O6 H6A 0.8701 . ?
O6 H6B 0.8701 . ?
C1 C2 1.430(4) . ?
C1 C7 1.381(4) . ?
C2 C3 1.397(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.409(4) . ?
C13 C14 1.360(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C5 C4 1.390(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.363(4) . ?
C11 C20 1.419(4) . ?
C7 H7 0.9500 . ?
C20 C15 1.418(4) . ?
C20 C19 1.414(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C8 1.517(4) . ?
C8 H8 1.0000 . ?
C8 C4 1.526(4) . ?
C8 C10 1.530(4) . ?
C15 C14 1.413(4) . ?
C15 C16 1.425(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.359(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(5) . ?
C17 C16 1.356(5) . ?
C14 H14 0.9500 . ?
C18 H18 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 H16 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
O5 S1 O3 112.20(13) . . ?
O5 S1 C12 105.64(13) . . ?
O3 S1 C12 105.52(12) . . ?
O4 S1 O5 113.45(14) . . ?
O4 S1 O3 113.42(15) . . ?
O4 S1 C12 105.73(14) . . ?
C1 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?
H6A O6 H6B 109.5 . . ?
O1 C1 C2 118.2(2) . . ?
O1 C1 C7 115.1(2) . . ?
C7 C1 C2 126.8(2) . . ?
O2 C2 C1 112.0(2) . . ?
O2 C2 C3 120.6(2) . . ?
C3 C2 C1 127.4(2) . . ?
C2 C3 H3 114.3 . . ?
C4 C3 C2 131.3(2) . . ?
C4 C3 H3 114.3 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C6 C5 H5 115.3 . . ?
C6 C5 C4 129.4(3) . . ?
C4 C5 H5 115.3 . . ?
C5 C6 H6 115.3 . . ?
C5 C6 C7 129.4(3) . . ?
C7 C6 H6 115.3 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C20 120.4(3) . . ?
C20 C11 H11 119.8 . . ?
C13 C12 S1 118.3(2) . . ?
C11 C12 S1 120.6(2) . . ?
C11 C12 C13 121.2(3) . . ?
C1 C7 C6 129.6(3) . . ?
C1 C7 H7 115.2 . . ?
C6 C7 H7 115.2 . . ?
C15 C20 C11 118.5(3) . . ?
C19 C20 C11 122.7(3) . . ?
C19 C20 C15 118.8(3) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
C9 C8 H8 107.8 . . ?
C9 C8 C4 112.8(2) . . ?
C9 C8 C10 110.2(2) . . ?
C4 C8 H8 107.8 . . ?
C4 C8 C10 110.4(2) . . ?
C10 C8 H8 107.8 . . ?
C3 C4 C8 116.0(2) . . ?
C5 C4 C3 125.9(3) . . ?
C5 C4 C8 118.1(2) . . ?
C20 C15 C16 118.8(3) . . ?
C14 C15 C20 119.2(3) . . ?
C14 C15 C16 122.0(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(3) . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_col-ao5-2
_database_code_depnum_ccdc_archive 'CCDC 2027386'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        colchicine
_chemical_formula_moiety         'C10 H7 O3 S, C22 H26 N O6'
_chemical_formula_sum            'C32 H33 N O9 S'
_chemical_formula_weight         607.65
_chemical_absolute_configuration .
_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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.825(2)
_cell_length_b                   16.685(5)
_cell_length_c                   21.993(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2871.5(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1363
_cell_measurement_temperature    220
_cell_measurement_theta_max      18.855
_cell_measurement_theta_min      2.442
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_preparation       tol
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21566
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.532
_diffrn_ambient_temperature      220
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3191
_reflns_number_total             5049
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.220
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5049
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.015
_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)+(0.0417P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C6(H6a,H6b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C8(H8), C11(H11), C4(H4a), C21(H21), C19(H19), C22(H22),
 C26(H26), C23(H23), C24(H24), C25(H25)
2.d Tetrahedral OH refined with riding coordinates:
 O4(H4)
2.e Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C18(H18a,H18b,H18c), C17(H17a,H17b,H17c), C15(H15a,H15b,
 H15c), C14(H14a,H14b,H14c)
;
_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 0.3647(2) 0.43586(9) 0.68183(7) 0.0372(4) Uani 1 1 d . . . . .
O1 O 0.2301(5) 0.8826(2) 0.47633(17) 0.0329(10) Uani 1 1 d . . . . .
O5 O 0.4090(5) 0.5304(2) 0.41723(17) 0.0382(11) Uani 1 1 d . . . . .
O4 O 0.3165(5) 0.4839(2) 0.51897(17) 0.0398(11) Uani 1 1 d . . . . .
H4 H 0.3254 0.4696 0.5550 0.060 Uiso 1 1 calc R . . . .
O3 O 0.4298(6) 1.0721(2) 0.61900(18) 0.0423(11) Uani 1 1 d . . . . .
O2 O 0.2557(5) 1.0396(2) 0.51747(18) 0.0422(11) Uani 1 1 d . . . . .
O7 O 0.2669(5) 0.4259(2) 0.62541(17) 0.0433(12) Uani 1 1 d . . . . .
O6 O -0.0556(5) 0.7201(3) 0.6720(2) 0.0554(14) Uani 1 1 d . . . . .
O8 O 0.4184(5) 0.5183(2) 0.69062(19) 0.0458(12) Uani 1 1 d . . . . .
O9 O 0.2788(5) 0.4024(3) 0.73407(18) 0.0512(13) Uani 1 1 d . . . . .
N1 N 0.1959(6) 0.6569(3) 0.6790(2) 0.0299(11) Uani 1 1 d . . . . .
H1 H 0.2491 0.6148 0.6927 0.036 Uiso 1 1 calc R . . . .
C12A C 0.3789(7) 0.7516(3) 0.5379(2) 0.0239(13) Uani 1 1 d . . . . .
C12 C 0.4154(7) 0.7374(3) 0.4772(3) 0.0261(14) Uani 1 1 d . . . . .
H12 H 0.4442 0.7841 0.4557 0.031 Uiso 1 1 calc R . . . .
C7A C 0.3290(7) 0.6909(3) 0.5789(2) 0.0252(13) Uani 1 1 d . . . . .
C1 C 0.3251(7) 0.9003(3) 0.5269(2) 0.0263(14) Uani 1 1 d . . . . .
C9 C 0.3383(7) 0.5627(3) 0.5152(3) 0.0284(13) Uani 1 1 d . . . . .
C12B C 0.3953(7) 0.8357(3) 0.5593(2) 0.0245(13) Uani 1 1 d . . . . .
C4A C 0.4900(7) 0.8532(3) 0.6122(3) 0.0266(14) Uani 1 1 d . . . . .
C8 C 0.3105(7) 0.6097(3) 0.5663(2) 0.0278(14) Uani 1 1 d . . . . .
H8 H 0.2704 0.5801 0.5997 0.033 Uiso 1 1 calc R . . . .
C10 C 0.3892(7) 0.5903(3) 0.4570(3) 0.0275(14) Uani 1 1 d . . . . .
C5 C 0.5797(7) 0.7862(3) 0.6450(3) 0.0304(15) Uani 1 1 d . . . . .
H5A H 0.6634 0.8091 0.6732 0.036 Uiso 1 1 calc R . . . .
H5B H 0.6419 0.7534 0.6154 0.036 Uiso 1 1 calc R . . . .
C11 C 0.4186(7) 0.6694(3) 0.4415(3) 0.0273(14) Uani 1 1 d . . . . .
H11 H 0.4449 0.6782 0.4003 0.033 Uiso 1 1 calc R . . . .
C16 C 0.0296(8) 0.6641(4) 0.6906(3) 0.0352(16) Uani 1 1 d . . . . .
C3 C 0.4292(8) 0.9943(3) 0.6012(3) 0.0325(16) Uani 1 1 d . . . . .
C7 C 0.2926(7) 0.7155(3) 0.6449(2) 0.0265(14) Uani 1 1 d . . . . .
H7 H 0.2249 0.7656 0.6438 0.032 Uiso 1 1 calc R . . . .
C4 C 0.5064(7) 0.9325(3) 0.6325(3) 0.0314(14) Uani 1 1 d . . . . .
H4A H 0.5704 0.9436 0.6677 0.038 Uiso 1 1 calc R . . . .
C2 C 0.3418(7) 0.9785(3) 0.5475(3) 0.0310(14) Uani 1 1 d . . . . .
C22A C 0.8642(9) 0.2969(3) 0.6617(3) 0.0417(17) Uani 1 1 d . . . . .
C20 C 0.5553(8) 0.3803(3) 0.6722(3) 0.0331(15) Uani 1 1 d . . . . .
C26A C 0.7237(9) 0.2766(3) 0.6244(3) 0.0416(17) Uani 1 1 d . . . . .
C6 C 0.4581(7) 0.7331(3) 0.6802(3) 0.0302(14) Uani 1 1 d . . . . .
H6A H 0.4292 0.7592 0.7187 0.036 Uiso 1 1 calc R . . . .
H6B H 0.5153 0.6823 0.6896 0.036 Uiso 1 1 calc R . . . .
C13 C 0.2586(8) 0.9275(4) 0.4216(3) 0.0413(16) Uani 1 1 d . . . . .
H13A H 0.2294 0.8947 0.3867 0.062 Uiso 1 1 calc GR . . . .
H13B H 0.3780 0.9428 0.4192 0.062 Uiso 1 1 calc GR . . . .
H13C H 0.1879 0.9752 0.4219 0.062 Uiso 1 1 calc GR . . . .
C21 C 0.6969(8) 0.3998(4) 0.7097(3) 0.0418(16) Uani 1 1 d . . . . .
H21 H 0.6870 0.4413 0.7384 0.050 Uiso 1 1 calc R . . . .
C18 C 0.4768(9) 0.5466(4) 0.3576(3) 0.0475(19) Uani 1 1 d . . . . .
H18A H 0.4964 0.4964 0.3365 0.071 Uiso 1 1 calc GR . . . .
H18B H 0.5838 0.5755 0.3614 0.071 Uiso 1 1 calc GR . . . .
H18C H 0.3958 0.5788 0.3348 0.071 Uiso 1 1 calc GR . . . .
C19 C 0.5684(9) 0.3207(4) 0.6311(3) 0.0439(17) Uani 1 1 d . . . . .
H19 H 0.4741 0.3081 0.6064 0.053 Uiso 1 1 calc R . . . .
C17 C -0.0461(8) 0.5976(4) 0.7287(3) 0.0477(18) Uani 1 1 d . . . . .
H17A H -0.0459 0.6134 0.7712 0.072 Uiso 1 1 calc GR . . . .
H17B H 0.0216 0.5493 0.7238 0.072 Uiso 1 1 calc GR . . . .
H17C H -0.1625 0.5873 0.7157 0.072 Uiso 1 1 calc GR . . . .
C22 C 0.8463(9) 0.3591(4) 0.7048(3) 0.0469(18) Uani 1 1 d . . . . .
H22 H 0.9386 0.3724 0.7303 0.056 Uiso 1 1 calc R . . . .
C15 C 0.5138(10) 1.0909(4) 0.6744(3) 0.056(2) Uani 1 1 d . . . . .
H15A H 0.6349 1.0797 0.6705 0.085 Uiso 1 1 calc GR . . . .
H15B H 0.4662 1.0587 0.7070 0.085 Uiso 1 1 calc GR . . . .
H15C H 0.4977 1.1473 0.6836 0.085 Uiso 1 1 calc GR . . . .
C26 C 0.7465(11) 0.2158(4) 0.5808(3) 0.058(2) Uani 1 1 d . . . . .
H26 H 0.6560 0.2026 0.5545 0.069 Uiso 1 1 calc R . . . .
C23 C 1.0210(10) 0.2552(4) 0.6548(4) 0.057(2) Uani 1 1 d . . . . .
H23 H 1.1150 0.2687 0.6793 0.069 Uiso 1 1 calc R . . . .
C24 C 1.0357(11) 0.1959(4) 0.6128(4) 0.065(2) Uani 1 1 d . . . . .
H24 H 1.1398 0.1683 0.6087 0.077 Uiso 1 1 calc R . . . .
C14 C 0.3636(10) 1.1003(4) 0.4913(3) 0.065(2) Uani 1 1 d . . . . .
H14A H 0.3669 1.0937 0.4475 0.098 Uiso 1 1 calc GR . . . .
H14B H 0.4782 1.0953 0.5076 0.098 Uiso 1 1 calc GR . . . .
H14C H 0.3183 1.1529 0.5011 0.098 Uiso 1 1 calc GR . . . .
C25 C 0.8986(12) 0.1757(4) 0.5759(4) 0.070(3) Uani 1 1 d . . . . .
H25 H 0.9101 0.1342 0.5474 0.084 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
S1 O7 1.467(4) . ?
S1 O8 1.452(4) . ?
S1 O9 1.443(4) . ?
S1 C20 1.768(6) . ?
O1 C1 1.371(6) . ?
O1 C13 1.435(6) . ?
O5 C10 1.337(6) . ?
O5 C18 1.440(7) . ?
O4 H4 0.8300 . ?
O4 C9 1.329(6) . ?
O3 C3 1.355(6) . ?
O3 C15 1.420(7) . ?
O2 C2 1.389(6) . ?
O2 C14 1.439(7) . ?
O6 C16 1.219(7) . ?
N1 H1 0.8700 . ?
N1 C16 1.331(7) . ?
N1 C7 1.446(7) . ?
C12A C12 1.385(7) . ?
C12A C7A 1.412(7) . ?
C12A C12B 1.486(7) . ?
C12 H12 0.9400 . ?
C12 C11 1.380(7) . ?
C7A C8 1.389(7) . ?
C7A C7 1.535(7) . ?
C1 C12B 1.403(7) . ?
C1 C2 1.387(7) . ?
C9 C8 1.388(7) . ?
C9 C10 1.417(7) . ?
C12B C4A 1.409(7) . ?
C4A C5 1.505(7) . ?
C4A C4 1.404(8) . ?
C8 H8 0.9400 . ?
C10 C11 1.381(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 C6 1.512(7) . ?
C11 H11 0.9400 . ?
C16 C17 1.512(8) . ?
C3 C4 1.379(8) . ?
C3 C2 1.390(8) . ?
C7 H7 0.9900 . ?
C7 C6 1.538(8) . ?
C4 H4A 0.9400 . ?
C22A C26A 1.413(9) . ?
C22A C22 1.413(8) . ?
C22A C23 1.418(9) . ?
C20 C21 1.419(8) . ?
C20 C19 1.348(8) . ?
C26A C19 1.428(9) . ?
C26A C26 1.407(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C21 H21 0.9400 . ?
C21 C22 1.356(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19 0.9400 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C22 H22 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C26 H26 0.9400 . ?
C26 C25 1.370(10) . ?
C23 H23 0.9400 . ?
C23 C24 1.359(10) . ?
C24 H24 0.9400 . ?
C24 C25 1.387(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C25 H25 0.9400 . ?

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
O7 S1 C20 106.2(3) . . ?
O8 S1 O7 111.8(2) . . ?
O8 S1 C20 105.6(3) . . ?
O9 S1 O7 112.7(3) . . ?
O9 S1 O8 113.3(3) . . ?
O9 S1 C20 106.6(3) . . ?
C1 O1 C13 118.9(4) . . ?
C10 O5 C18 119.9(5) . . ?
C9 O4 H4 109.5 . . ?
C3 O3 C15 117.5(5) . . ?
C2 O2 C14 115.0(5) . . ?
C16 N1 H1 118.3 . . ?
C16 N1 C7 123.4(5) . . ?
C7 N1 H1 118.3 . . ?
C12 C12A C7A 123.3(5) . . ?
C12 C12A C12B 116.7(5) . . ?
C7A C12A C12B 120.0(5) . . ?
C12A C12 H12 113.1 . . ?
C11 C12 C12A 133.8(5) . . ?
C11 C12 H12 113.1 . . ?
C12A C7A C7 117.6(5) . . ?
C8 C7A C12A 126.9(5) . . ?
C8 C7A C7 115.5(5) . . ?
O1 C1 C12B 117.3(5) . . ?
O1 C1 C2 121.2(5) . . ?
C2 C1 C12B 121.3(5) . . ?
O4 C9 C8 119.2(5) . . ?
O4 C9 C10 114.5(5) . . ?
C8 C9 C10 126.3(5) . . ?
C1 C12B C12A 122.0(5) . . ?
C1 C12B C4A 117.8(5) . . ?
C4A C12B C12A 120.1(5) . . ?
C12B C4A C5 119.2(5) . . ?
C4 C4A C12B 120.4(5) . . ?
C4 C4A C5 120.3(5) . . ?
C7A C8 H8 112.9 . . ?
C9 C8 C7A 134.1(5) . . ?
C9 C8 H8 112.9 . . ?
O5 C10 C9 112.3(5) . . ?
O5 C10 C11 122.3(5) . . ?
C11 C10 C9 125.4(5) . . ?
C4A C5 H5A 109.0 . . ?
C4A C5 H5B 109.0 . . ?
C4A C5 C6 112.8(5) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C12 C11 C10 130.0(5) . . ?
C12 C11 H11 115.0 . . ?
C10 C11 H11 115.0 . . ?
O6 C16 N1 122.6(6) . . ?
O6 C16 C17 122.3(6) . . ?
N1 C16 C17 115.1(5) . . ?
O3 C3 C4 124.7(6) . . ?
O3 C3 C2 115.4(5) . . ?
C4 C3 C2 119.8(5) . . ?
N1 C7 C7A 114.0(4) . . ?
N1 C7 H7 107.6 . . ?
N1 C7 C6 107.9(4) . . ?
C7A C7 H7 107.6 . . ?
C7A C7 C6 111.9(5) . . ?
C6 C7 H7 107.6 . . ?
C4A C4 H4A 119.8 . . ?
C3 C4 C4A 120.4(5) . . ?
C3 C4 H4A 119.8 . . ?
O2 C2 C3 120.2(5) . . ?
C1 C2 O2 119.4(5) . . ?
C1 C2 C3 120.1(5) . . ?
C26A C22A C22 119.3(6) . . ?
C26A C22A C23 119.5(6) . . ?
C22 C22A C23 121.2(7) . . ?
C21 C20 S1 118.0(4) . . ?
C19 C20 S1 122.1(5) . . ?
C19 C20 C21 119.9(6) . . ?
C22A C26A C19 118.6(6) . . ?
C26 C26A C22A 118.0(7) . . ?
C26 C26A C19 123.3(7) . . ?
C5 C6 C7 112.5(4) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(6) . . ?
C22 C21 H21 119.6 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C26A 120.9(7) . . ?
C20 C19 H19 119.5 . . ?
C26A C19 H19 119.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22A C22 H22 119.8 . . ?
C21 C22 C22A 120.4(7) . . ?
C21 C22 H22 119.8 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C26A C26 H26 119.5 . . ?
C25 C26 C26A 121.0(8) . . ?
C25 C26 H26 119.5 . . ?
C22A C23 H23 119.9 . . ?
C24 C23 C22A 120.3(8) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(8) . . ?
C25 C24 H24 119.7 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C26 C25 C24 120.6(7) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?

_olex2_submission_original_sample_id colchicine
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_colchicine-aii2

_database_code_depnum_ccdc_archive 'CCDC 2027385'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            colchicine
_chemical_name_systematic        Colchicine-AII2
_chemical_formula_moiety         'C7 H7 O3 S, C22 H26 N O6'
_chemical_formula_sum            'C29 H33 N O9 S'
_chemical_formula_weight         571.62
_chemical_absolute_configuration .
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.858(3)
_cell_length_b                   8.1256(19)
_cell_length_c                   13.356(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.313(7)
_cell_angle_gamma                90
_cell_volume                     1395.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1349
_cell_measurement_temperature    220
_cell_measurement_theta_max      20.48
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2012
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             604
_exptl_crystal_preparation       'MEK evaporation'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12708
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.525
_diffrn_ambient_temperature      220
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3621
_reflns_number_total             6298
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.250
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6298
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      0.936
_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)+(0.0368P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-H4
 0.83 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C6(H6a,H6b)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C24(H24), C23(H23), C11(H11), C4(H4a), C20(H20), C12(H12),
 C21(H21)
3.d Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C17(H17a,H17b,H17c), C15(H15a,H15b,H15c), C18(H18a,H18b,
 H18c), C13(H13a,H13b,H13c), C14(H14a,H14b,H14c)
;
_atom_sites_solution_hydrogens   mixed
_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 0.24300(9) 0.10585(18) 0.35349(10) 0.0315(3) Uani 1 1 d . . . . .
O5 O 0.6779(2) 0.1092(5) 0.5772(3) 0.0333(8) Uani 1 1 d . . . . .
O1 O 0.8808(2) 0.3633(5) 0.1852(3) 0.0358(9) Uani 1 1 d . . . . .
O3 O 0.8298(3) 0.8526(5) -0.0014(3) 0.0389(10) Uani 1 1 d . . . . .
O7 O 0.3375(3) 0.0134(5) 0.3824(3) 0.0381(10) Uani 1 1 d . . . . .
O2 O 0.9462(2) 0.5914(5) 0.0418(3) 0.0361(9) Uani 1 1 d . . . . .
O9 O 0.1605(3) -0.0005(5) 0.3189(3) 0.0424(10) Uani 1 1 d . . . . .
O4 O 0.5101(3) 0.0637(5) 0.4868(3) 0.0413(11) Uani 1 1 d D . . . .
O8 O 0.2664(3) 0.2392(5) 0.2850(3) 0.0439(11) Uani 1 1 d . . . . .
O6 O 0.5485(3) 0.0955(6) 0.0656(3) 0.0503(11) Uani 1 1 d . . . . .
N1 N 0.4463(3) 0.2528(6) 0.1595(3) 0.0311(11) Uani 1 1 d . . . . .
H1 H 0.3842 0.2688 0.1821 0.037 Uiso 1 1 calc R . . . .
C12B C 0.7257(3) 0.5169(7) 0.2075(4) 0.0253(12) Uani 1 1 d . . . . .
C3 C 0.7903(4) 0.7477(7) 0.0672(4) 0.0276(12) Uani 1 1 d . . . . .
C7 C 0.5264(3) 0.3720(7) 0.1826(4) 0.0286(12) Uani 1 1 d . . . . .
H7 H 0.5739 0.3754 0.1254 0.034 Uiso 1 1 calc R . . . .
C12A C 0.6912(4) 0.4003(6) 0.2858(4) 0.0272(12) Uani 1 1 d . . . . .
C1 C 0.8220(4) 0.4991(7) 0.1614(4) 0.0267(12) Uani 1 1 d . . . . .
C16 C 0.4642(4) 0.1177(8) 0.1043(4) 0.0327(12) Uani 1 1 d . . . . .
C10 C 0.6718(4) 0.1872(6) 0.4900(4) 0.0282(12) Uani 1 1 d . . . . .
C9 C 0.5757(4) 0.1611(6) 0.4381(4) 0.0276(12) Uani 1 1 d . . . . .
C7A C 0.5918(4) 0.3278(6) 0.2774(4) 0.0265(12) Uani 1 1 d . . . . .
C8 C 0.5450(4) 0.2247(7) 0.3458(4) 0.0283(12) Uani 1 1 d . . . . .
H8 H 0.4781 0.1905 0.3251 0.034 Uiso 1 1 calc R . . . .
C24 C 0.2710(4) 0.2754(7) 0.5298(4) 0.0319(13) Uani 1 1 d . . . . .
H24 H 0.3425 0.2716 0.5169 0.038 Uiso 1 1 calc R . . . .
C22 C 0.1311(4) 0.3633(7) 0.6355(4) 0.0349(13) Uani 1 1 d . . . . .
C5 C 0.5584(4) 0.6715(7) 0.2318(4) 0.0318(13) Uani 1 1 d . . . . .
H5A H 0.5310 0.7821 0.2186 0.038 Uiso 1 1 calc R . . . .
H5B H 0.5687 0.6595 0.3043 0.038 Uiso 1 1 calc R . . . .
C23 C 0.2364(4) 0.3550(7) 0.6141(4) 0.0329(13) Uani 1 1 d . . . . .
H23 H 0.2851 0.4047 0.6580 0.039 Uiso 1 1 calc R . . . .
C11 C 0.7527(4) 0.2829(7) 0.4542(4) 0.0318(13) Uani 1 1 d . . . . .
H11 H 0.8120 0.2865 0.4966 0.038 Uiso 1 1 calc R . . . .
C2 C 0.8525(3) 0.6134(7) 0.0895(4) 0.0275(11) Uani 1 1 d . . . . .
C19 C 0.2001(4) 0.2010(6) 0.4641(4) 0.0264(12) Uani 1 1 d . . . . .
C4 C 0.6954(4) 0.7678(7) 0.1124(4) 0.0294(13) Uani 1 1 d . . . . .
H4A H 0.6536 0.8596 0.0969 0.035 Uiso 1 1 calc R . . . .
C20 C 0.0948(4) 0.2075(8) 0.4845(4) 0.0359(14) Uani 1 1 d . . . . .
H20 H 0.0464 0.1565 0.4408 0.043 Uiso 1 1 calc R . . . .
C6 C 0.4796(4) 0.5434(6) 0.1940(4) 0.0319(13) Uani 1 1 d . . . . .
H6A H 0.4222 0.5376 0.2409 0.038 Uiso 1 1 calc R . . . .
H6B H 0.4507 0.5792 0.1290 0.038 Uiso 1 1 calc R . . . .
C4A C 0.6626(4) 0.6520(6) 0.1808(4) 0.0283(13) Uani 1 1 d . . . . .
C12 C 0.7609(4) 0.3736(7) 0.3671(4) 0.0311(13) Uani 1 1 d . . . . .
H12 H 0.8251 0.4276 0.3610 0.037 Uiso 1 1 calc R . . . .
C25 C 0.0940(5) 0.4533(8) 0.7260(4) 0.0504(18) Uani 1 1 d . . . . .
H25A H 0.1036 0.3843 0.7848 0.076 Uiso 1 1 calc GR . . . .
H25B H 0.0209 0.4798 0.7170 0.076 Uiso 1 1 calc GR . . . .
H25C H 0.1337 0.5541 0.7348 0.076 Uiso 1 1 calc GR . . . .
C17 C 0.3759(4) -0.0035(8) 0.0943(4) 0.0435(15) Uani 1 1 d . . . . .
H17A H 0.3167 0.0493 0.0613 0.065 Uiso 1 1 calc GR . . . .
H17B H 0.3563 -0.0406 0.1602 0.065 Uiso 1 1 calc GR . . . .
H17C H 0.3977 -0.0970 0.0549 0.065 Uiso 1 1 calc GR . . . .
C15 C 0.7764(5) 1.0039(8) -0.0205(5) 0.0539(18) Uani 1 1 d . . . . .
H15A H 0.8141 1.0676 -0.0693 0.081 Uiso 1 1 calc GR . . . .
H15B H 0.7720 1.0660 0.0412 0.081 Uiso 1 1 calc GR . . . .
H15C H 0.7069 0.9809 -0.0466 0.081 Uiso 1 1 calc GR . . . .
C21 C 0.0607(4) 0.2888(8) 0.5688(4) 0.0403(16) Uani 1 1 d . . . . .
H21 H -0.0109 0.2937 0.5812 0.048 Uiso 1 1 calc R . . . .
C18 C 0.7751(4) 0.1106(8) 0.6352(4) 0.0410(14) Uani 1 1 d . . . . .
H18A H 0.8314 0.0756 0.5931 0.061 Uiso 1 1 calc GR . . . .
H18B H 0.7697 0.0360 0.6916 0.061 Uiso 1 1 calc GR . . . .
H18C H 0.7888 0.2211 0.6596 0.061 Uiso 1 1 calc GR . . . .
C13 C 0.9887(4) 0.3909(8) 0.2121(5) 0.0536(19) Uani 1 1 d . . . . .
H13A H 1.0284 0.4051 0.1519 0.080 Uiso 1 1 calc GR . . . .
H13B H 1.0154 0.2970 0.2495 0.080 Uiso 1 1 calc GR . . . .
H13C H 0.9948 0.4890 0.2531 0.080 Uiso 1 1 calc GR . . . .
C14 C 0.9351(5) 0.5155(11) -0.0533(4) 0.064(2) Uani 1 1 d . . . . .
H14A H 0.8864 0.5782 -0.0947 0.097 Uiso 1 1 calc GR . . . .
H14B H 0.9090 0.4043 -0.0451 0.097 Uiso 1 1 calc GR . . . .
H14C H 1.0021 0.5118 -0.0851 0.097 Uiso 1 1 calc GR . . . .
H4 H 0.459(3) 0.035(5) 0.449(2) 0.038(17) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O7 1.472(4) . ?
S1 O9 1.436(4) . ?
S1 O8 1.454(4) . ?
S1 C19 1.767(5) . ?
O5 C10 1.326(6) . ?
O5 C18 1.454(5) . ?
O1 C1 1.371(6) . ?
O1 C13 1.443(6) . ?
O3 C3 1.358(6) . ?
O3 C15 1.428(7) . ?
O2 C2 1.387(5) . ?
O2 C14 1.416(7) . ?
O4 C9 1.336(6) . ?
O4 H4 0.85(2) . ?
O6 C16 1.226(6) . ?
N1 H1 0.8700 . ?
N1 C7 1.442(6) . ?
N1 C16 1.345(7) . ?
C12B C12A 1.486(7) . ?
C12B C1 1.403(6) . ?
C12B C4A 1.406(7) . ?
C3 C2 1.382(7) . ?
C3 C4 1.384(7) . ?
C7 H7 0.9900 . ?
C7 C7A 1.547(7) . ?
C7 C6 1.526(7) . ?
C12A C7A 1.409(6) . ?
C12A C12 1.409(7) . ?
C1 C2 1.399(7) . ?
C16 C17 1.506(7) . ?
C10 C9 1.419(7) . ?
C10 C11 1.393(7) . ?
C9 C8 1.385(7) . ?
C7A C8 1.387(7) . ?
C8 H8 0.9400 . ?
C24 H24 0.9400 . ?
C24 C23 1.380(7) . ?
C24 C19 1.389(7) . ?
C22 C23 1.391(7) . ?
C22 C25 1.501(8) . ?
C22 C21 1.394(8) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 C6 1.531(7) . ?
C5 C4A 1.525(7) . ?
C23 H23 0.9400 . ?
C11 H11 0.9400 . ?
C11 C12 1.383(7) . ?
C19 C20 1.388(6) . ?
C4 H4A 0.9400 . ?
C4 C4A 1.384(7) . ?
C20 H20 0.9400 . ?
C20 C21 1.385(8) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C12 H12 0.9400 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C21 H21 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 S1 C19 106.0(2) . . ?
O9 S1 O7 112.1(2) . . ?
O9 S1 O8 114.1(2) . . ?
O9 S1 C19 106.8(2) . . ?
O8 S1 O7 111.4(2) . . ?
O8 S1 C19 105.8(2) . . ?
C10 O5 C18 119.8(4) . . ?
C1 O1 C13 117.1(4) . . ?
C3 O3 C15 118.4(4) . . ?
C2 O2 C14 113.4(4) . . ?
C9 O4 H4 111.1(19) . . ?
C7 N1 H1 118.8 . . ?
C16 N1 H1 118.8 . . ?
C16 N1 C7 122.4(4) . . ?
C1 C12B C12A 121.6(5) . . ?
C1 C12B C4A 118.6(5) . . ?
C4A C12B C12A 119.8(4) . . ?
O3 C3 C2 114.7(4) . . ?
O3 C3 C4 124.6(5) . . ?
C2 C3 C4 120.7(5) . . ?
N1 C7 H7 107.7 . . ?
N1 C7 C7A 113.0(4) . . ?
N1 C7 C6 110.7(4) . . ?
C7A C7 H7 107.7 . . ?
C6 C7 H7 107.7 . . ?
C6 C7 C7A 109.8(4) . . ?
C7A C12A C12B 119.7(4) . . ?
C12 C12A C12B 116.4(4) . . ?
C12 C12A C7A 123.8(5) . . ?
O1 C1 C12B 118.0(5) . . ?
O1 C1 C2 122.1(4) . . ?
C2 C1 C12B 119.8(5) . . ?
O6 C16 N1 121.0(5) . . ?
O6 C16 C17 122.6(6) . . ?
N1 C16 C17 116.4(5) . . ?
O5 C10 C9 113.1(4) . . ?
O5 C10 C11 122.6(5) . . ?
C11 C10 C9 124.4(5) . . ?
O4 C9 C10 113.8(4) . . ?
O4 C9 C8 118.9(4) . . ?
C8 C9 C10 127.3(5) . . ?
C12A C7A C7 116.3(4) . . ?
C8 C7A C7 116.4(4) . . ?
C8 C7A C12A 127.3(5) . . ?
C9 C8 C7A 133.9(5) . . ?
C9 C8 H8 113.1 . . ?
C7A C8 H8 113.1 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C19 120.0(5) . . ?
C19 C24 H24 120.0 . . ?
C23 C22 C25 121.2(5) . . ?
C23 C22 C21 117.9(5) . . ?
C21 C22 C25 120.9(5) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4A C5 H5A 109.4 . . ?
C4A C5 H5B 109.4 . . ?
C4A C5 C6 111.3(4) . . ?
C24 C23 C22 121.6(5) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C10 C11 H11 114.4 . . ?
C12 C11 C10 131.2(5) . . ?
C12 C11 H11 114.4 . . ?
O2 C2 C1 119.4(5) . . ?
C3 C2 O2 120.5(5) . . ?
C3 C2 C1 120.2(4) . . ?
C24 C19 S1 120.4(4) . . ?
C20 C19 S1 120.3(4) . . ?
C20 C19 C24 119.2(5) . . ?
C3 C4 H4A 120.2 . . ?
C3 C4 C4A 119.5(5) . . ?
C4A C4 H4A 120.2 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C7 C6 C5 113.2(4) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
C12B C4A C5 118.4(5) . . ?
C4 C4A C12B 121.1(4) . . ?
C4 C4A C5 120.5(4) . . ?
C12A C12 H12 113.9 . . ?
C11 C12 C12A 132.1(5) . . ?
C11 C12 H12 113.9 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.9(5) . . ?
C20 C21 H21 119.6 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
_olex2_exptl_crystal_mounting_method ' '
_olex2_submission_original_sample_id Colchicne-AII2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22019967_0m
_database_code_depnum_ccdc_archive 'CCDC 2027395'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 O3 S, C10 H13 O2'
_chemical_formula_sum            'C17 H20 O5 S'
_chemical_formula_weight         336.39
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6868(2)
_cell_length_b                   31.6978(11)
_cell_length_c                   7.7242(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.6550(10)
_cell_angle_gamma                90
_cell_volume                     1633.87(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6048
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1650 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.8889.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.570
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2864
_reflns_number_total             3758
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.336
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+1.2226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C3(H3), C7(H7), C13(H13), C15(H15), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.79906(7) 0.36853(2) 0.58208(7) 0.02447(14) Uani 1 1 d . . . . .
O4 O 0.8721(2) 0.35134(4) 0.4236(2) 0.0314(4) Uani 1 1 d . . . . .
O3 O 0.5846(2) 0.37881(4) 0.5621(2) 0.0321(4) Uani 1 1 d . . . . .
O2 O 0.0225(2) 0.27391(5) 0.4174(2) 0.0340(4) Uani 1 1 d . . . . .
H2 H 0.0265 0.2998 0.4403 0.051 Uiso 1 1 calc GR . . . .
O1 O 0.3067(2) 0.32311(4) 0.5272(2) 0.0304(3) Uani 1 1 d . . . . .
H1 H 0.4094 0.3375 0.5541 0.046 Uiso 1 1 calc GR . . . .
O5 O 0.8466(2) 0.34209(5) 0.7320(2) 0.0348(4) Uani 1 1 d . . . . .
C11 C 0.9244(3) 0.41694(6) 0.6228(3) 0.0234(4) Uani 1 1 d . . . . .
C4 C 0.3357(3) 0.18178(6) 0.5226(3) 0.0239(4) Uani 1 1 d . . . . .
C16 C 0.8386(3) 0.44835(6) 0.7185(3) 0.0277(5) Uani 1 1 d . . . . .
H16 H 0.7058 0.4452 0.7536 0.033 Uiso 1 1 calc R . . . .
C12 C 1.1181(3) 0.42182(6) 0.5708(3) 0.0273(4) Uani 1 1 d . . . . .
H12 H 1.1768 0.4005 0.5043 0.033 Uiso 1 1 calc R . . . .
C2 C 0.1906(3) 0.25557(6) 0.4815(3) 0.0231(4) Uani 1 1 d . . . . .
C3 C 0.1931(3) 0.21208(6) 0.4676(3) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.0758 0.2006 0.4099 0.029 Uiso 1 1 calc R . . . .
C14 C 1.1441(3) 0.48945(6) 0.7142(3) 0.0287(5) Uani 1 1 d . . . . .
C1 C 0.3493(3) 0.28257(6) 0.5473(3) 0.0232(4) Uani 1 1 d . . . . .
C7 C 0.5292(3) 0.26938(7) 0.6289(3) 0.0282(5) Uani 1 1 d . . . . .
H7 H 0.6165 0.2914 0.6699 0.034 Uiso 1 1 calc R . . . .
C13 C 1.2251(3) 0.45791(7) 0.6164(3) 0.0287(5) Uani 1 1 d . . . . .
H13 H 1.3571 0.4611 0.5797 0.034 Uiso 1 1 calc R . . . .
C15 C 0.9485(3) 0.48448(7) 0.7628(3) 0.0304(5) Uani 1 1 d . . . . .
H15 H 0.8890 0.5061 0.8272 0.036 Uiso 1 1 calc R . . . .
C5 C 0.5184(3) 0.19027(7) 0.6137(3) 0.0300(5) Uani 1 1 d . . . . .
H5 H 0.5964 0.1663 0.6486 0.036 Uiso 1 1 calc R . . . .
C8 C 0.2786(3) 0.13636(6) 0.4786(3) 0.0263(4) Uani 1 1 d . . . . .
H8 H 0.2307 0.1357 0.3534 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6001(3) 0.22897(7) 0.6594(3) 0.0322(5) Uani 1 1 d . . . . .
H6 H 0.7266 0.2276 0.7225 0.039 Uiso 1 1 calc R . . . .
C17 C 1.2655(4) 0.52791(7) 0.7682(3) 0.0386(6) Uani 1 1 d . . . . .
H17A H 1.3309 0.5233 0.8838 0.058 Uiso 1 1 calc GR . . . .
H17B H 1.1769 0.5525 0.7709 0.058 Uiso 1 1 calc GR . . . .
H17C H 1.3675 0.5329 0.6849 0.058 Uiso 1 1 calc GR . . . .
C9 C 0.1034(4) 0.12250(7) 0.5831(3) 0.0394(6) Uani 1 1 d . . . . .
H9A H 0.1451 0.1228 0.7071 0.059 Uiso 1 1 calc GR . . . .
H9B H 0.0622 0.0939 0.5484 0.059 Uiso 1 1 calc GR . . . .
H9C H -0.0093 0.1419 0.5608 0.059 Uiso 1 1 calc GR . . . .
C10 C 0.4494(4) 0.10487(7) 0.5025(3) 0.0402(6) Uani 1 1 d . . . . .
H10A H 0.5634 0.1147 0.4399 0.060 Uiso 1 1 calc GR . . . .
H10B H 0.4050 0.0774 0.4567 0.060 Uiso 1 1 calc GR . . . .
H10C H 0.4898 0.1022 0.6262 0.060 Uiso 1 1 calc GR . . . .


_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 O4 1.4526(16) . ?
S1 O3 1.4691(15) . ?
S1 O5 1.4486(15) . ?
S1 C11 1.7669(19) . ?
O2 H2 0.8400 . ?
O2 C2 1.333(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.323(2) . ?
C11 C16 1.386(3) . ?
C11 C12 1.389(3) . ?
C4 C3 1.400(3) . ?
C4 C5 1.396(3) . ?
C4 C8 1.522(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.392(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C2 C3 1.383(3) . ?
C2 C1 1.431(3) . ?
C3 H3 0.9500 . ?
C14 C13 1.384(3) . ?
C14 C15 1.393(3) . ?
C14 C17 1.509(3) . ?
C1 C7 1.387(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.381(3) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.379(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.529(3) . ?
C8 C10 1.519(3) . ?
C6 H6 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
O4 S1 O3 111.93(9) . . ?
O4 S1 C11 107.12(9) . . ?
O3 S1 C11 105.96(9) . . ?
O5 S1 O4 112.83(9) . . ?
O5 S1 O3 112.04(10) . . ?
O5 S1 C11 106.42(9) . . ?
C2 O2 H2 109.5 . . ?
C1 O1 H1 109.5 . . ?
C16 C11 S1 120.70(16) . . ?
C16 C11 C12 119.97(18) . . ?
C12 C11 S1 119.09(15) . . ?
C3 C4 C8 115.12(17) . . ?
C5 C4 C3 125.28(19) . . ?
C5 C4 C8 119.59(18) . . ?
C11 C16 H16 120.3 . . ?
C11 C16 C15 119.5(2) . . ?
C15 C16 H16 120.3 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
O2 C2 C3 114.83(17) . . ?
O2 C2 C1 117.39(17) . . ?
C3 C2 C1 127.70(18) . . ?
C4 C3 H3 113.9 . . ?
C2 C3 C4 132.18(18) . . ?
C2 C3 H3 113.9 . . ?
C13 C14 C15 118.18(19) . . ?
C13 C14 C17 120.8(2) . . ?
C15 C14 C17 121.0(2) . . ?
O1 C1 C2 112.93(17) . . ?
O1 C1 C7 121.36(18) . . ?
C7 C1 C2 125.69(18) . . ?
C1 C7 H7 115.3 . . ?
C6 C7 C1 129.47(19) . . ?
C6 C7 H7 115.3 . . ?
C12 C13 C14 121.5(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C4 C5 H5 115.8 . . ?
C6 C5 C4 128.3(2) . . ?
C6 C5 H5 115.8 . . ?
C4 C8 H8 107.2 . . ?
C4 C8 C9 110.12(17) . . ?
C9 C8 H8 107.2 . . ?
C10 C8 C4 114.73(18) . . ?
C10 C8 H8 107.2 . . ?
C10 C8 C9 110.04(19) . . ?
C7 C6 H6 114.5 . . ?
C5 C6 C7 130.9(2) . . ?
C5 C6 H6 114.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22019968_0m
_database_code_depnum_ccdc_archive 'CCDC 2027390'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        hinokitiol
_chemical_formula_moiety         'C10 H6 O6 S2, 2(C10 H13 O2)'
_chemical_formula_sum            'C30 H32 O10 S2'
_chemical_formula_weight         616.67
_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'
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'

_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                   6.8451(3)
_cell_length_b                   9.0199(4)
_cell_length_c                   12.2623(6)
_cell_angle_alpha                81.489(2)
_cell_angle_beta                 78.810(2)
_cell_angle_gamma                70.4640(10)
_cell_volume                     697.12(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4026
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.465
_cell_measurement_theta_min      2.405
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0730 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.9094.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9256
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.573
_diffrn_reflns_theta_min         2.406
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2680
_reflns_number_total             3738
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.608
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.9330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1358
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C17(H17), C5(H5), C6(H6), C18(H18), C19(H19), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C9(H9a,H9b,H9c)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.45479(10) 0.48266(7) 0.72784(5) 0.02404(16) Uani 1 1 d . . . . .
O5 O 0.3263(3) 0.3787(2) 0.75412(14) 0.0316(4) Uani 1 1 d . . . . .
O3 O 0.6316(3) 0.42840(19) 0.63820(13) 0.0278(4) Uani 1 1 d . . . . .
O2 O 0.7611(3) 0.6178(2) 0.48472(14) 0.0299(4) Uani 1 1 d . . . . .
H2 H 0.7179 0.5642 0.5403 0.045 Uiso 1 1 calc GR . . . .
O4 O 0.3377(3) 0.6472(2) 0.70813(15) 0.0327(4) Uani 1 1 d . . . . .
O1 O 0.7812(3) 0.8295(2) 0.32278(14) 0.0287(4) Uani 1 1 d . . . . .
H1 H 0.7535 0.7446 0.3270 0.043 Uiso 1 1 calc GR . . . .
C7 C 0.7559(4) 1.0227(3) 0.4310(2) 0.0238(5) Uani 1 1 d . . . . .
H7 H 0.7619 1.0842 0.3612 0.029 Uiso 1 1 calc R . . . .
C20 C 0.5525(4) 0.4896(2) 1.04704(18) 0.0197(4) Uani 1 1 d . . . . .
C16 C 0.5737(4) 0.4617(3) 0.84883(18) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.7693(3) 0.8680(3) 0.42510(19) 0.0228(5) Uani 1 1 d . . . . .
C17 C 0.7865(4) 0.3971(3) 0.8393(2) 0.0249(5) Uani 1 1 d . . . . .
H17 H 0.8670 0.3653 0.7696 0.030 Uiso 1 1 calc R . . . .
C5 C 0.7342(4) 1.0451(3) 0.6352(2) 0.0249(5) Uani 1 1 d . . . . .
H5 H 0.7164 1.1211 0.6854 0.030 Uiso 1 1 calc R . . . .
C6 C 0.7350(4) 1.1021(3) 0.5237(2) 0.0241(5) Uani 1 1 d . . . . .
H6 H 0.7188 1.2116 0.5084 0.029 Uiso 1 1 calc R . . . .
C2 C 0.7656(4) 0.7509(3) 0.5167(2) 0.0240(5) Uani 1 1 d . . . . .
C4 C 0.7560(4) 0.8919(3) 0.68389(19) 0.0235(5) Uani 1 1 d . . . . .
C18 C 0.8872(4) 0.3775(3) 0.9330(2) 0.0268(5) Uani 1 1 d . . . . .
H18 H 1.0354 0.3329 0.9259 0.032 Uiso 1 1 calc R . . . .
C19 C 0.7733(4) 0.4221(3) 1.03356(19) 0.0242(5) Uani 1 1 d . . . . .
H19 H 0.8435 0.4077 1.0958 0.029 Uiso 1 1 calc R . . . .
C3 C 0.7697(4) 0.7640(3) 0.6276(2) 0.0249(5) Uani 1 1 d . . . . .
H3 H 0.7847 0.6679 0.6740 0.030 Uiso 1 1 calc R . . . .
C8 C 0.7496(4) 0.8598(3) 0.8097(2) 0.0284(5) Uani 1 1 d . . . . .
H8 H 0.8225 0.7446 0.8261 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5206(5) 0.8942(4) 0.8659(2) 0.0375(6) Uani 1 1 d . . . . .
H10A H 0.4460 1.0073 0.8537 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.5156 0.8632 0.9461 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.4537 0.8340 0.8336 0.056 Uiso 1 1 calc GR . . . .
C9 C 0.8595(5) 0.9505(3) 0.8589(2) 0.0367(6) Uani 1 1 d . . . . .
H9A H 1.0041 0.9296 0.8201 0.055 Uiso 1 1 calc GR . . . .
H9B H 0.8606 0.9162 0.9385 0.055 Uiso 1 1 calc GR . . . .
H9C H 0.7844 1.0640 0.8496 0.055 Uiso 1 1 calc GR . . . .


_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 1.4517(18) . ?
S1 O3 1.4693(18) . ?
S1 O4 1.4409(18) . ?
S1 C16 1.784(2) . ?
O2 H2 0.8400 . ?
O2 C2 1.328(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.331(3) . ?
C7 H7 0.9500 . ?
C7 C1 1.379(3) . ?
C7 C6 1.391(3) . ?
C20 C20 1.432(4) 2_667 ?
C20 C16 1.433(3) 2_667 ?
C20 C19 1.414(3) . ?
C16 C20 1.433(3) 2_667 ?
C16 C17 1.364(3) . ?
C1 C2 1.426(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.411(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C5 C4 1.393(3) . ?
C6 H6 0.9500 . ?
C2 C3 1.388(3) . ?
C4 C3 1.398(3) . ?
C4 C8 1.522(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.362(3) . ?
C19 H19 0.9500 . ?
C3 H3 0.9500 . ?
C8 H8 1.0000 . ?
C8 C10 1.532(4) . ?
C8 C9 1.527(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
O5 S1 O3 112.09(10) . . ?
O5 S1 C16 105.16(10) . . ?
O3 S1 C16 104.70(11) . . ?
O4 S1 O5 114.09(12) . . ?
O4 S1 O3 112.45(11) . . ?
O4 S1 C16 107.50(10) . . ?
C2 O2 H2 109.5 . . ?
C1 O1 H1 109.5 . . ?
C1 C7 H7 115.1 . . ?
C1 C7 C6 129.7(2) . . ?
C6 C7 H7 115.1 . . ?
C20 C20 C16 117.7(3) 2_667 2_667 ?
C19 C20 C20 119.1(3) . 2_667 ?
C19 C20 C16 123.2(2) . 2_667 ?
C20 C16 S1 120.46(17) 2_667 . ?
C17 C16 S1 118.16(17) . . ?
C17 C16 C20 121.4(2) . 2_667 ?
O1 C1 C7 114.9(2) . . ?
O1 C1 C2 118.6(2) . . ?
C7 C1 C2 126.5(2) . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C6 C5 H5 115.5 . . ?
C6 C5 C4 129.0(2) . . ?
C4 C5 H5 115.5 . . ?
C7 C6 H6 115.2 . . ?
C5 C6 C7 129.5(2) . . ?
C5 C6 H6 115.2 . . ?
O2 C2 C1 111.9(2) . . ?
O2 C2 C3 120.9(2) . . ?
C3 C2 C1 127.2(2) . . ?
C5 C4 C3 125.3(2) . . ?
C5 C4 C8 118.7(2) . . ?
C3 C4 C8 115.8(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.4 . . ?
C2 C3 C4 132.1(2) . . ?
C2 C3 H3 113.9 . . ?
C4 C3 H3 113.9 . . ?
C4 C8 H8 107.5 . . ?
C4 C8 C10 108.9(2) . . ?
C4 C8 C9 114.3(2) . . ?
C10 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C9 C8 C10 110.9(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22019953_0ma
_database_code_depnum_ccdc_archive 'CCDC 2027396'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        tropolone
_chemical_formula_moiety         'C7 H7 O3 S, C7 H7 O2'
_chemical_formula_sum            'C14 H14 O5 S'
_chemical_formula_weight         294.31
_chemical_absolute_configuration ?
_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'
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'

_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   6.9880(2)
_cell_length_b                   30.2686(8)
_cell_length_c                   6.2510(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1322.19(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7239
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1424 before and 0.0982 after correction.
The Ratio of minimum to maximum transmission is 0.6510.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13788
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.692
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                2762
_reflns_number_total             2946
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.306
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1111 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.041
_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)+(0.0373P)²+0.5242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0975
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C9(H9), C10(H10), C3(H3), C6(H6), C4(H4), C12(H12), C5(H5)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.23765(10) 0.37613(2) 0.63914(16) 0.02364(19) Uani 1 1 d . . . . .
O1 O 0.2587(3) 0.30711(7) 0.1783(4) 0.0277(5) Uani 1 1 d . . . . .
H1 H 0.2874 0.3176 0.2984 0.042 Uiso 1 1 calc GR . . . .
O4 O 0.1084(3) 0.35489(8) 0.7902(4) 0.0307(5) Uani 1 1 d . . . . .
O2 O 0.1318(3) 0.26946(7) -0.1598(4) 0.0285(5) Uani 1 1 d . . . . .
H2 H 0.1431 0.2960 -0.1224 0.043 Uiso 1 1 calc GR . . . .
O3 O 0.3587(4) 0.34326(8) 0.5288(4) 0.0334(6) Uani 1 1 d . . . . .
O5 O 0.1414(4) 0.40551(8) 0.4940(4) 0.0340(6) Uani 1 1 d . . . . .
C8 C 0.4020(5) 0.40751(9) 0.7928(5) 0.0221(6) Uani 1 1 d . . . . .
C13 C 0.5749(5) 0.42014(11) 0.7016(5) 0.0276(7) Uani 1 1 d . . . . .
H13 H 0.6048 0.4119 0.5589 0.033 Uiso 1 1 calc R . . . .
C1 C 0.2618(4) 0.26318(10) 0.1883(5) 0.0228(7) Uani 1 1 d . . . . .
C7 C 0.3266(5) 0.24165(11) 0.3704(5) 0.0260(7) Uani 1 1 d . . . . .
H7 H 0.3603 0.2605 0.4859 0.031 Uiso 1 1 calc R . . . .
C9 C 0.3567(5) 0.41963(10) 1.0000(5) 0.0266(7) Uani 1 1 d . . . . .
H9 H 0.2386 0.4108 1.0618 0.032 Uiso 1 1 calc R . . . .
C10 C 0.4858(5) 0.44488(9) 1.1170(6) 0.0305(7) Uani 1 1 d . . . . .
H10 H 0.4538 0.4537 1.2584 0.037 Uiso 1 1 calc R . . . .
C2 C 0.1921(4) 0.24347(10) -0.0037(5) 0.0225(6) Uani 1 1 d . . . . .
C3 C 0.1756(5) 0.19834(11) -0.0442(5) 0.0260(7) Uani 1 1 d . . . . .
H3 H 0.1163 0.1911 -0.1764 0.031 Uiso 1 1 calc R . . . .
C6 C 0.3499(5) 0.19695(11) 0.4097(6) 0.0295(7) Uani 1 1 d . . . . .
H6 H 0.3999 0.1898 0.5467 0.035 Uiso 1 1 calc R . . . .
C11 C 0.6608(5) 0.45739(10) 1.0307(6) 0.0311(8) Uani 1 1 d . . . . .
C4 C 0.2316(5) 0.16240(11) 0.0774(6) 0.0294(8) Uani 1 1 d . . . . .
H4 H 0.2125 0.1344 0.0122 0.035 Uiso 1 1 calc R . . . .
C12 C 0.7030(5) 0.44488(11) 0.8205(6) 0.0323(8) Uani 1 1 d . . . . .
H12 H 0.8214 0.4535 0.7585 0.039 Uiso 1 1 calc R . . . .
C5 C 0.3111(5) 0.16120(11) 0.2792(6) 0.0303(7) Uani 1 1 d . . . . .
H5 H 0.3425 0.1329 0.3343 0.036 Uiso 1 1 calc R . . . .
C14 C 0.8055(6) 0.48267(12) 1.1624(8) 0.0456(10) Uani 1 1 d . . . . .
H14A H 0.7449 0.4932 1.2944 0.068 Uiso 1 1 calc GR . . . .
H14B H 0.8523 0.5080 1.0800 0.068 Uiso 1 1 calc GR . . . .
H14C H 0.9130 0.4632 1.1982 0.068 Uiso 1 1 calc GR . . . .


_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 O4 1.457(3) . ?
S1 O3 1.477(2) . ?
S1 O5 1.437(2) . ?
S1 C8 1.773(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.332(4) . ?
O2 H2 0.8400 . ?
O2 C2 1.322(4) . ?
C8 C13 1.389(5) . ?
C8 C9 1.383(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.384(5) . ?
C1 C7 1.388(4) . ?
C1 C2 1.426(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.385(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(5) . ?
C2 C3 1.394(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.382(5) . ?
C11 C12 1.399(5) . ?
C11 C14 1.511(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(5) . ?
C12 H12 0.9500 . ?
C5 H5 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
O4 S1 O3 111.15(15) . . ?
O4 S1 C8 106.67(16) . . ?
O3 S1 C8 104.06(14) . . ?
O5 S1 O4 113.10(15) . . ?
O5 S1 O3 112.94(16) . . ?
O5 S1 C8 108.27(13) . . ?
C1 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?
C13 C8 S1 119.2(3) . . ?
C9 C8 S1 120.1(3) . . ?
C9 C8 C13 120.7(3) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 C8 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
O1 C1 C7 120.8(3) . . ?
O1 C1 C2 111.9(3) . . ?
C7 C1 C2 127.3(3) . . ?
C1 C7 H7 115.0 . . ?
C6 C7 C1 130.0(3) . . ?
C6 C7 H7 115.0 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
O2 C2 C1 118.7(3) . . ?
O2 C2 C3 115.0(3) . . ?
C3 C2 C1 126.2(3) . . ?
C2 C3 H3 114.8 . . ?
C4 C3 C2 130.3(3) . . ?
C4 C3 H3 114.8 . . ?
C7 C6 H6 115.2 . . ?
C5 C6 C7 129.6(3) . . ?
C5 C6 H6 115.2 . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 C14 121.0(4) . . ?
C12 C11 C14 120.5(4) . . ?
C3 C4 H4 115.2 . . ?
C5 C4 C3 129.6(3) . . ?
C5 C4 H4 115.2 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C6 C5 H5 116.6 . . ?
C4 C5 C6 126.7(3) . . ?
C4 C5 H5 116.6 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22019971_0m
_database_code_depnum_ccdc_archive 'CCDC 2027393'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        tropolone
_chemical_formula_moiety         'C10 H6 O6 S2, 2(C7 H7 O2)'
_chemical_formula_sum            'C24 H20 O10 S2'
_chemical_formula_weight         532.52
_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'
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'

_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                   7.0583(2)
_cell_length_b                   8.1581(3)
_cell_length_c                   10.0680(3)
_cell_angle_alpha                102.6500(10)
_cell_angle_beta                 104.1720(10)
_cell_angle_gamma                90.5980(10)
_cell_volume                     547.19(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4663
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.505
_cell_measurement_theta_min      2.943
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1249 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.9360. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6645
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.943
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'D8 ADVENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2233
_reflns_number_total             2440
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.351
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.081
_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)+(0.0291P)²+0.3747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C3(H3), C7(H7), C5(H5), C4(H4), C6(H6)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.18646(5) 0.65238(5) 0.76277(4) 0.01908(12) Uani 1 1 d . . . . .
O1 O 0.58782(15) 0.67764(13) 0.57964(11) 0.0212(2) Uani 1 1 d . . . . .
H1 H 0.4981 0.6513 0.6142 0.032 Uiso 1 1 calc GR . . . .
O2 O 0.84442(16) 0.80836(15) 0.48402(13) 0.0256(3) Uani 1 1 d . . . . .
H2 H 0.8531 0.7385 0.5350 0.038 Uiso 1 1 calc GR . . . .
O5 O 0.00204(16) 0.62079(16) 0.65549(12) 0.0274(3) Uani 1 1 d . . . . .
O3 O 0.34908(16) 0.58319(16) 0.70667(12) 0.0282(3) Uani 1 1 d . . . . .
O4 O 0.22660(19) 0.82543(15) 0.83997(13) 0.0317(3) Uani 1 1 d . . . . .
C12 C 0.0067(2) 0.55239(17) 0.95285(14) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.1625(2) 0.52969(17) 0.88406(14) 0.0155(3) Uani 1 1 d . . . . .
C9 C 0.2946(2) 0.41138(18) 0.90774(15) 0.0181(3) Uani 1 1 d . . . . .
H9 H 0.3974 0.3987 0.8613 0.022 Uiso 1 1 calc R . . . .
C2 C 0.6588(2) 0.82040(18) 0.42365(16) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.5117(2) 0.74227(17) 0.47029(15) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.2794(2) 0.30807(19) 1.00048(16) 0.0203(3) Uani 1 1 d . . . . .
H10 H 0.3714 0.2257 1.0157 0.024 Uiso 1 1 calc R . . . .
C11 C 0.1332(2) 0.32554(18) 1.06860(15) 0.0189(3) Uani 1 1 d . . . . .
H11 H 0.1248 0.2554 1.1311 0.023 Uiso 1 1 calc R . . . .
C3 C 0.6256(2) 0.91552(19) 0.32168(16) 0.0220(3) Uani 1 1 d . . . . .
H3 H 0.7406 0.9659 0.3100 0.026 Uiso 1 1 calc R . . . .
C7 C 0.3103(2) 0.72975(19) 0.41218(16) 0.0215(3) Uani 1 1 d . . . . .
H7 H 0.2364 0.6660 0.4528 0.026 Uiso 1 1 calc R . . . .
C5 C 0.2621(3) 0.8946(2) 0.22427(17) 0.0270(4) Uani 1 1 d . . . . .
H5 H 0.1627 0.9287 0.1552 0.032 Uiso 1 1 calc R . . . .
C4 C 0.4525(2) 0.94860(19) 0.23460(16) 0.0248(3) Uani 1 1 d . . . . .
H4 H 0.4668 1.0185 0.1731 0.030 Uiso 1 1 calc R . . . .
C6 C 0.2005(2) 0.7959(2) 0.30392(17) 0.0253(3) Uani 1 1 d . . . . .
H6 H 0.0632 0.7698 0.2812 0.030 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
S1 O5 1.4526(12) . ?
S1 O3 1.4651(12) . ?
S1 O4 1.4424(13) . ?
S1 C8 1.7763(14) . ?
O1 H1 0.8400 . ?
O1 C1 1.3226(17) . ?
O2 H2 0.8400 . ?
O2 C2 1.3173(18) . ?
C12 C12 1.428(3) 2_567 ?
C12 C8 1.4298(19) . ?
C12 C11 1.423(2) 2_567 ?
C8 C9 1.367(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.4092(19) . ?
C2 C1 1.4355(19) . ?
C2 C3 1.395(2) . ?
C1 C7 1.391(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.364(2) . ?
C11 C12 1.423(2) 2_567 ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.383(2) . ?
C5 C6 1.388(2) . ?
C4 H4 0.9500 . ?
C6 H6 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
O5 S1 O3 111.65(7) . . ?
O5 S1 C8 105.23(6) . . ?
O3 S1 C8 104.41(7) . . ?
O4 S1 O5 113.99(8) . . ?
O4 S1 O3 113.26(7) . . ?
O4 S1 C8 107.39(7) . . ?
C1 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?
C12 C12 C8 117.91(16) 2_567 . ?
C11 C12 C12 119.32(16) 2_567 2_567 ?
C11 C12 C8 122.77(12) 2_567 . ?
C12 C8 S1 120.67(10) . . ?
C9 C8 S1 118.23(11) . . ?
C9 C8 C12 121.10(12) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.48(13) . . ?
C10 C9 H9 119.8 . . ?
O2 C2 C1 118.63(13) . . ?
O2 C2 C3 115.09(13) . . ?
C3 C2 C1 126.24(14) . . ?
O1 C1 C2 112.25(13) . . ?
O1 C1 C7 120.87(13) . . ?
C7 C1 C2 126.88(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.43(13) . . ?
C11 C10 H10 119.8 . . ?
C12 C11 H11 119.6 2_567 . ?
C10 C11 C12 120.77(13) . 2_567 ?
C10 C11 H11 119.6 . . ?
C2 C3 H3 114.7 . . ?
C4 C3 C2 130.64(14) . . ?
C4 C3 H3 114.7 . . ?
C1 C7 H7 115.0 . . ?
C6 C7 C1 130.09(14) . . ?
C6 C7 H7 115.0 . . ?
C4 C5 H5 116.5 . . ?
C4 C5 C6 126.97(15) . . ?
C6 C5 H5 116.5 . . ?
C3 C4 H4 115.3 . . ?
C5 C4 C3 129.34(15) . . ?
C5 C4 H4 115.3 . . ?
C7 C6 H6 115.3 . . ?
C5 C6 C7 129.48(15) . . ?
C5 C6 H6 115.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mm
_database_code_depnum_ccdc_archive 'CCDC 2027398'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 O3 S, C7 H7 O'
_chemical_formula_sum            'C14 H14 O4 S'
_chemical_formula_weight         278.31
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5417(4)
_cell_length_b                   10.8327(3)
_cell_length_c                   12.7884(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.4270(10)
_cell_angle_gamma                90
_cell_volume                     1295.64(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4081
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.366
_cell_measurement_theta_min      2.485
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0786 before and 0.0413 after correction. The Ratio of minimum to maximum transmission is 0.9068. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10367
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.446
_diffrn_reflns_theta_min         2.485
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2138
_reflns_number_total             2632
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.255
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.4920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C9(H9), C10(H10), C2(H2), C7(H7), C6(H6), C5(H5), C4(H4),
 C3(H3)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.58742(5) 0.68010(4) 0.70362(4) 0.03165(15) Uani 1 1 d . . . . .
O1 O 0.30772(14) 0.45527(12) 0.64743(11) 0.0435(3) Uani 1 1 d . . . . .
H1 H 0.3776 0.4987 0.6391 0.065 Uiso 1 1 calc GR . . . .
O3 O 0.61934(14) 0.61181(13) 0.80222(10) 0.0447(4) Uani 1 1 d . . . . .
O2 O 0.49629(15) 0.60771(15) 0.61934(10) 0.0504(4) Uani 1 1 d . . . . .
O4 O 0.53166(17) 0.80168(13) 0.71281(15) 0.0611(5) Uani 1 1 d . . . . .
C13 C 0.80353(18) 0.81364(16) 0.64365(13) 0.0303(4) Uani 1 1 d . . . . .
H13 H 0.7532 0.8854 0.6578 0.036 Uiso 1 1 calc R . . . .
C8 C 0.75011(18) 0.69729(15) 0.65827(13) 0.0277(4) Uani 1 1 d . . . . .
C12 C 0.93129(19) 0.82424(17) 0.60811(13) 0.0340(4) Uani 1 1 d . . . . .
H12 H 0.9674 0.9040 0.5976 0.041 Uiso 1 1 calc R . . . .
C1 C 0.33693(18) 0.33871(17) 0.63566(13) 0.0313(4) Uani 1 1 d . . . . .
C11 C 1.00759(19) 0.72076(18) 0.58748(13) 0.0350(4) Uani 1 1 d . . . . .
C9 C 0.82550(19) 0.59261(16) 0.63976(13) 0.0337(4) Uani 1 1 d . . . . .
H9 H 0.7895 0.5129 0.6506 0.040 Uiso 1 1 calc R . . . .
C10 C 0.95331(19) 0.60514(18) 0.60547(14) 0.0368(4) Uani 1 1 d . . . . .
H10 H 1.0053 0.5333 0.5939 0.044 Uiso 1 1 calc R . . . .
C2 C 0.4680(2) 0.30529(19) 0.60818(14) 0.0373(4) Uani 1 1 d . . . . .
H2 H 0.5259 0.3718 0.5934 0.045 Uiso 1 1 calc R . . . .
C7 C 0.22784(19) 0.25745(17) 0.65195(13) 0.0337(4) Uani 1 1 d . . . . .
H7 H 0.1431 0.2957 0.6645 0.040 Uiso 1 1 calc R . . . .
C14 C 1.1440(2) 0.7327(2) 0.54642(16) 0.0484(5) Uani 1 1 d . . . . .
H14A H 1.1364 0.8027 0.4971 0.073 Uiso 1 1 calc GR . . . .
H14B H 1.1607 0.6568 0.5090 0.073 Uiso 1 1 calc GR . . . .
H14C H 1.2240 0.7465 0.6064 0.073 Uiso 1 1 calc GR . . . .
C6 C 0.2270(2) 0.13137(18) 0.65218(14) 0.0405(4) Uani 1 1 d . . . . .
H6 H 0.1406 0.0946 0.6629 0.049 Uiso 1 1 calc R . . . .
C5 C 0.3347(2) 0.04824(19) 0.63902(15) 0.0465(5) Uani 1 1 d . . . . .
H5 H 0.3143 -0.0367 0.6470 0.056 Uiso 1 1 calc R . . . .
C4 C 0.4650(2) 0.0743(2) 0.61614(15) 0.0464(5) Uani 1 1 d . . . . .
H4 H 0.5242 0.0052 0.6104 0.056 Uiso 1 1 calc R . . . .
C3 C 0.5227(2) 0.1896(2) 0.60006(15) 0.0440(5) Uani 1 1 d . . . . .
H3 H 0.6136 0.1874 0.5805 0.053 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
S1 O3 1.4414(13) . ?
S1 O2 1.4701(14) . ?
S1 O4 1.4340(14) . ?
S1 C8 1.7714(18) . ?
O1 C1 1.308(2) . ?
C13 C8 1.386(2) . ?
C13 C12 1.388(3) . ?
C8 C9 1.388(2) . ?
C12 C11 1.390(3) . ?
C1 C2 1.412(3) . ?
C1 C7 1.410(3) . ?
C11 C10 1.392(3) . ?
C11 C14 1.503(3) . ?
C9 C10 1.382(3) . ?
C2 C3 1.370(3) . ?
C7 C6 1.366(3) . ?
C6 C5 1.401(3) . ?
C5 C4 1.362(3) . ?
C4 C3 1.396(3) . ?

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
O3 S1 O2 111.06(9) . . ?
O3 S1 C8 107.06(8) . . ?
O2 S1 C8 104.21(8) . . ?
O4 S1 O3 114.66(10) . . ?
O4 S1 O2 112.02(10) . . ?
O4 S1 C8 107.08(8) . . ?
C8 C13 C12 119.33(16) . . ?
C13 C8 S1 120.62(13) . . ?
C13 C8 C9 120.20(16) . . ?
C9 C8 S1 119.16(13) . . ?
C13 C12 C11 121.51(17) . . ?
O1 C1 C2 119.71(16) . . ?
O1 C1 C7 113.91(16) . . ?
C7 C1 C2 126.38(17) . . ?
C12 C11 C10 117.92(17) . . ?
C12 C11 C14 121.28(18) . . ?
C10 C11 C14 120.80(18) . . ?
C10 C9 C8 119.58(17) . . ?
C9 C10 C11 121.43(17) . . ?
C3 C2 C1 128.54(19) . . ?
C6 C7 C1 129.01(18) . . ?
C7 C6 C5 129.63(19) . . ?
C4 C5 C6 127.9(2) . . ?
C5 C4 C3 128.36(19) . . ?
C2 C3 C4 129.80(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20180153_0m
_database_code_depnum_ccdc_archive 'CCDC 2036740'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H25 N O6), 3(H2 O)'
_chemical_formula_sum            'C44 H56 N2 O15'
_chemical_formula_weight         852.90
_chemical_absolute_configuration .
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.829(4)
_cell_length_b                   10.484(4)
_cell_length_c                   15.998(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.885(6)
_cell_angle_gamma                90
_cell_volume                     2167.1(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1482
_cell_measurement_temperature    205
_cell_measurement_theta_max      19.966
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0896 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.7393. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_preparation       H2O
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_av_unetI/netI     0.1614
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19131
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.694
_diffrn_reflns_theta_min         1.576
_diffrn_ambient_temperature      205
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                4603
_reflns_number_total             9854
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.328
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         9854
_refine_ls_number_restraints     451
_refine_ls_R_factor_all          0.1701
_refine_ls_R_factor_gt           0.0760
_refine_ls_restrained_S_all      0.941
_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)+(0.0840P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.2126
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Free rotating group:
 O7(H7A,H7B), O8(H8A,H8B), O9(H9A,H9B)
3.b Ternary CH refined with riding coordinates:
 C25(H25), C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C24(H24A,H24B), C23(H23A,H23B), C5(H5A,H5B)
3.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C11(H11), C22(H22), C8(H8), C29(H29), C12(H12), C30(H30),
 C26(H26), C4(H4)
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C18(H18A,H18B,
 H18C), C35(H35A,H35B,H35C), C32(H32A,H32B,H32C), C13(H13A,H13B,H13C), C15(H15A,
 H15B,H15C), C17(H17A,H17B,H17C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.5885(4) 0.2680(5) 0.4808(3) 0.0420(13) Uani 1 1 d . U . . .
O5 O 0.6159(4) 0.8393(5) 0.3577(3) 0.0445(13) Uani 1 1 d . U . . .
O10 O 0.4432(4) 0.4165(5) -0.0761(4) 0.0462(13) Uani 1 1 d . U . . .
O14 O 0.0085(4) 0.6144(5) -0.0909(4) 0.0481(14) Uani 1 1 d . U . . .
O2 O 0.6171(4) 0.0622(5) 0.5903(4) 0.0467(13) Uani 1 1 d . U . . .
O11 O 0.5898(4) 0.2924(5) -0.1220(4) 0.0481(13) Uani 1 1 d . U . . .
O12 O 0.5451(4) 0.0710(5) -0.2120(4) 0.0504(14) Uani 1 1 d . U . . .
O4 O 0.8040(4) 0.8123(5) 0.3747(4) 0.0570(16) Uani 1 1 d . U . . .
O3 O 0.7755(4) 0.0546(5) 0.7490(4) 0.0556(15) Uani 1 1 d . U . . .
O15 O 0.3459(5) 0.1747(6) 0.1353(4) 0.0626(17) Uani 1 1 d . U . . .
O13 O -0.0329(4) 0.4046(6) -0.0328(4) 0.0580(16) Uani 1 1 d . U . . .
O6 O 0.8943(4) 0.2874(6) 0.3708(4) 0.0602(16) Uani 1 1 d . U . . .
N2 N 0.2101(5) 0.0688(6) 0.0430(4) 0.0415(14) Uani 1 1 d . U . . .
H2 H 0.1571 0.0204 0.0375 0.050 Uiso 1 1 calc R . . . .
N1 N 0.9829(5) 0.4272(6) 0.4746(4) 0.0409(15) Uani 1 1 d . U . . .
H1 H 1.0356 0.4788 0.4924 0.049 Uiso 1 1 calc R . . . .
O7 O 0.8250(5) 1.0640(7) 0.4434(4) 0.0651(17) Uani 1 1 d . U . . .
H7A H 0.8364 1.1132 0.4049 0.098 Uiso 1 1 d G . . . .
H7B H 0.7883 1.0028 0.4120 0.098 Uiso 1 1 d G . . . .
C19 C 0.4185(5) 0.3010(7) -0.1195(5) 0.0327(15) Uani 1 1 d . U . . .
C22A C 0.2969(5) 0.1334(7) -0.1834(5) 0.0369(16) Uani 1 1 d . U . . .
C20 C 0.4924(5) 0.2376(7) -0.1434(5) 0.0372(16) Uani 1 1 d . U . . .
C34 C 0.2752(6) 0.1006(8) 0.1241(5) 0.0453(19) Uani 1 1 d . U . . .
C25A C 0.1865(5) 0.2503(7) -0.0637(5) 0.0357(16) Uani 1 1 d . U . . .
C30B C 0.3194(5) 0.2500(7) -0.1389(4) 0.0337(15) Uani 1 1 d . U . . .
C4A C 0.8308(6) 0.3579(7) 0.6589(5) 0.0388(17) Uani 1 1 d . U . . .
C6 C 0.9793(6) 0.4511(9) 0.6245(5) 0.0465(19) Uani 1 1 d . U . . .
H6A H 1.0301 0.3829 0.6488 0.056 Uiso 1 1 calc R . . . .
H6B H 1.0172 0.5311 0.6280 0.056 Uiso 1 1 calc R . . . .
C11 C 0.6099(6) 0.6541(7) 0.4414(5) 0.0400(17) Uani 1 1 d . U . . .
H11 H 0.5409 0.6766 0.4316 0.048 Uiso 1 1 calc R . . . .
C7A C 0.8227(5) 0.5109(7) 0.4924(5) 0.0342(15) Uani 1 1 d . U . . .
C22 C 0.3696(6) 0.0724(7) -0.2095(5) 0.0385(16) Uani 1 1 d . U . . .
H22 H 0.3524 -0.0047 -0.2413 0.046 Uiso 1 1 calc R . . . .
C21 C 0.4673(6) 0.1225(7) -0.1897(5) 0.0389(16) Uani 1 1 d . U . . .
C1 C 0.6770(5) 0.2605(7) 0.5566(5) 0.0354(16) Uani 1 1 d . U . . .
C10 C 0.6597(6) 0.7347(7) 0.4039(5) 0.0393(16) Uani 1 1 d . U . . .
C25 C 0.2270(5) 0.1143(7) -0.0363(5) 0.0383(16) Uani 1 1 d . U . . .
H25 H 0.3028 0.1167 -0.0218 0.046 Uiso 1 1 calc R . . . .
C28 C 0.0733(6) 0.5177(7) -0.0915(5) 0.0354(16) Uani 1 1 d . U . . .
C3 C 0.7717(6) 0.1561(7) 0.6942(5) 0.0398(17) Uani 1 1 d . U . . .
C24 C 0.1828(6) 0.0237(7) -0.1143(5) 0.0414(18) Uani 1 1 d . U . . .
H24A H 0.2190 -0.0582 -0.0990 0.050 Uiso 1 1 calc R . . . .
H24B H 0.1096 0.0086 -0.1241 0.050 Uiso 1 1 calc R . . . .
O8 O 0.7364(6) 0.2568(7) 0.1978(5) 0.077(2) Uani 1 1 d . U . . .
H8A H 0.6794 0.2168 0.1891 0.115 Uiso 1 1 d G . . . .
H8B H 0.7797 0.2231 0.2454 0.115 Uiso 1 1 d G . . . .
C16 C 0.9692(6) 0.3592(8) 0.4032(6) 0.0480(19) Uani 1 1 d . U . . .
C8 C 0.8314(6) 0.6155(7) 0.4455(5) 0.0431(18) Uani 1 1 d . U . . .
H8 H 0.8946 0.6170 0.4358 0.052 Uiso 1 1 calc R . . . .
C9 C 0.7680(6) 0.7244(7) 0.4068(5) 0.0399(17) Uani 1 1 d . U . . .
C29 C 0.1491(5) 0.5318(7) -0.1259(5) 0.0411(17) Uani 1 1 d . U . . .
H29 H 0.1567 0.6153 -0.1440 0.049 Uiso 1 1 calc R . . . .
C12 C 0.6439(5) 0.5426(7) 0.4924(5) 0.0406(18) Uani 1 1 d . U . . .
H12 H 0.5939 0.5058 0.5121 0.049 Uiso 1 1 calc R . . . .
C12B C 0.7477(5) 0.3634(7) 0.5783(5) 0.0346(15) Uani 1 1 d . U . . .
C12A C 0.7354(6) 0.4770(7) 0.5189(5) 0.0363(16) Uani 1 1 d . U . . .
C14 C 0.6549(6) -0.0604(8) 0.5778(6) 0.050(2) Uani 1 1 d . U . . .
H14A H 0.7021 -0.0919 0.6347 0.075 Uiso 1 1 calc GR . . . .
H14B H 0.6909 -0.0535 0.5360 0.075 Uiso 1 1 calc GR . . . .
H14C H 0.5972 -0.1190 0.5544 0.075 Uiso 1 1 calc GR . . . .
C27 C 0.0441(6) 0.4029(7) -0.0554(5) 0.0380(17) Uani 1 1 d . U . . .
C7 C 0.9150(5) 0.4220(7) 0.5262(5) 0.0401(17) Uani 1 1 d . U . . .
H7 H 0.8885 0.3337 0.5230 0.048 Uiso 1 1 calc R . . . .
C30 C 0.2176(6) 0.4436(7) -0.1390(5) 0.0399(17) Uani 1 1 d . U . . .
H30 H 0.2571 0.4754 -0.1715 0.048 Uiso 1 1 calc R . . . .
C26 C 0.1037(6) 0.2869(7) -0.0420(5) 0.0400(17) Uani 1 1 d . U . . .
H26 H 0.0807 0.2232 -0.0121 0.048 Uiso 1 1 calc R . . . .
C30A C 0.2382(5) 0.3180(7) -0.1129(5) 0.0351(16) Uani 1 1 d . U . . .
C2 C 0.6901(5) 0.1574(7) 0.6143(5) 0.0367(16) Uani 1 1 d . U . . .
C33 C 0.5271(7) -0.0530(7) -0.2530(6) 0.051(2) Uani 1 1 d . U . . .
H33A H 0.5122 -0.1133 -0.2132 0.077 Uiso 1 1 calc GR . . . .
H33B H 0.5883 -0.0805 -0.2643 0.077 Uiso 1 1 calc GR . . . .
H33C H 0.4688 -0.0490 -0.3090 0.077 Uiso 1 1 calc GR . . . .
C4 C 0.8426(6) 0.2546(8) 0.7169(5) 0.0451(18) Uani 1 1 d . U . . .
H4 H 0.8989 0.2522 0.7715 0.054 Uiso 1 1 calc R . . . .
C23 C 0.1916(6) 0.0721(8) -0.1998(5) 0.0445(18) Uani 1 1 d . U . . .
H23A H 0.1369 0.1349 -0.2270 0.053 Uiso 1 1 calc R . . . .
H23B H 0.1816 0.0010 -0.2419 0.053 Uiso 1 1 calc R . . . .
C5 C 0.9111(6) 0.4625(8) 0.6807(5) 0.047(2) Uani 1 1 d . U . . .
H5A H 0.9543 0.4579 0.7442 0.057 Uiso 1 1 calc R . . . .
H5B H 0.8763 0.5456 0.6697 0.057 Uiso 1 1 calc R . . . .
O9 O 0.5561(6) 0.1262(8) 0.1891(7) 0.096(3) Uani 1 1 d . U . . .
H9A H 0.4957 0.1422 0.1905 0.144 Uiso 1 1 d G . . . .
H9B H 0.5466 0.0626 0.1531 0.144 Uiso 1 1 d G . . . .
C36 C 0.0128(8) 0.7303(8) -0.1345(7) 0.065(3) Uani 1 1 d . U . . .
H36A H 0.0788 0.7716 -0.1040 0.098 Uiso 1 1 calc GR . . . .
H36B H -0.0428 0.7858 -0.1334 0.098 Uiso 1 1 calc GR . . . .
H36C H 0.0054 0.7131 -0.1961 0.098 Uiso 1 1 calc GR . . . .
C18 C 0.5074(6) 0.8597(8) 0.3353(5) 0.049(2) Uani 1 1 d . U . . .
H18A H 0.4929 0.8751 0.3895 0.074 Uiso 1 1 calc GR . . . .
H18B H 0.4697 0.7849 0.3052 0.074 Uiso 1 1 calc GR . . . .
H18C H 0.4859 0.9331 0.2960 0.074 Uiso 1 1 calc GR . . . .
C35 C 0.2551(7) 0.0415(11) 0.2001(6) 0.071(3) Uani 1 1 d . U . . .
H35A H 0.2695 0.1027 0.2485 0.106 Uiso 1 1 calc GR . . . .
H35B H 0.2995 -0.0325 0.2207 0.106 Uiso 1 1 calc GR . . . .
H35C H 0.1832 0.0153 0.1811 0.106 Uiso 1 1 calc GR . . . .
C32 C 0.6719(7) 0.2278(10) -0.0563(7) 0.073(3) Uani 1 1 d . U . . .
H32A H 0.6571 0.2209 -0.0016 0.110 Uiso 1 1 calc GR . . . .
H32B H 0.7357 0.2751 -0.0446 0.110 Uiso 1 1 calc GR . . . .
H32C H 0.6792 0.1431 -0.0778 0.110 Uiso 1 1 calc GR . . . .
C13 C 0.5939(7) 0.2000(10) 0.4078(5) 0.062(3) Uani 1 1 d . U . . .
H13A H 0.6205 0.1151 0.4269 0.093 Uiso 1 1 calc GR . . . .
H13B H 0.6396 0.2438 0.3834 0.093 Uiso 1 1 calc GR . . . .
H13C H 0.5253 0.1937 0.3623 0.093 Uiso 1 1 calc GR . . . .
C15 C 0.8488(8) 0.0583(10) 0.8375(6) 0.075(3) Uani 1 1 d . U . . .
H15A H 0.8325 -0.0075 0.8731 0.113 Uiso 1 1 calc GR . . . .
H15B H 0.8465 0.1412 0.8637 0.113 Uiso 1 1 calc GR . . . .
H15C H 0.9176 0.0436 0.8364 0.113 Uiso 1 1 calc GR . . . .
C17 C 1.0507(8) 0.3736(11) 0.3627(7) 0.069(3) Uani 1 1 d . U . . .
H17A H 1.0182 0.3901 0.2991 0.103 Uiso 1 1 calc GR . . . .
H17B H 1.0911 0.2958 0.3717 0.103 Uiso 1 1 calc GR . . . .
H17C H 1.0958 0.4443 0.3909 0.103 Uiso 1 1 calc GR . . . .
C31 C 0.4817(10) 0.4116(11) 0.0166(6) 0.089(4) Uani 1 1 d . U . . .
H31A H 0.4952 0.4975 0.0405 0.134 Uiso 1 1 calc GR . . . .
H31B H 0.5454 0.3628 0.0369 0.134 Uiso 1 1 calc GR . . . .
H31C H 0.4313 0.3711 0.0374 0.134 Uiso 1 1 calc GR . . . .


_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 1.384(8) . ?
O1 C13 1.393(10) . ?
O5 C10 1.339(9) . ?
O5 C18 1.430(9) . ?
O10 C19 1.377(9) . ?
O10 C31 1.386(10) . ?
O14 C28 1.356(8) . ?
O14 C36 1.412(10) . ?
O2 C14 1.428(10) . ?
O2 C2 1.373(9) . ?
O11 C20 1.391(8) . ?
O11 C32 1.415(10) . ?
O12 C21 1.360(9) . ?
O12 C33 1.437(9) . ?
O4 C9 1.243(9) . ?
O3 C3 1.368(9) . ?
O3 C15 1.419(10) . ?
O15 C34 1.211(9) . ?
O13 C27 1.241(9) . ?
O6 C16 1.236(9) . ?
N2 H2 0.8700 . ?
N2 C34 1.332(10) . ?
N2 C25 1.449(9) . ?
N1 H1 0.8700 . ?
N1 C16 1.301(10) . ?
N1 C7 1.456(9) . ?
O7 H7A 0.8603 . ?
O7 H7B 0.8600 . ?
C19 C20 1.382(10) . ?
C19 C30B 1.400(10) . ?
C22A C30B 1.393(10) . ?
C22A C22 1.377(10) . ?
C22A C23 1.526(10) . ?
C20 C21 1.394(10) . ?
C34 C35 1.477(12) . ?
C25A C25 1.537(10) . ?
C25A C26 1.366(10) . ?
C25A C30A 1.426(10) . ?
C30B C30A 1.508(10) . ?
C4A C12B 1.389(10) . ?
C4A C4 1.398(11) . ?
C4A C5 1.510(10) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 C7 1.537(10) . ?
C6 C5 1.522(11) . ?
C11 H11 0.9400 . ?
C11 C10 1.357(10) . ?
C11 C12 1.408(10) . ?
C7A C8 1.358(10) . ?
C7A C12A 1.460(10) . ?
C7A C7 1.515(10) . ?
C22 H22 0.9400 . ?
C22 C21 1.377(10) . ?
C1 C12B 1.413(10) . ?
C1 C2 1.391(10) . ?
C10 C9 1.485(10) . ?
C25 H25 0.9900 . ?
C25 C24 1.514(10) . ?
C28 C29 1.355(10) . ?
C28 C27 1.453(11) . ?
C3 C2 1.370(10) . ?
C3 C4 1.381(11) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 C23 1.504(11) . ?
O8 H8A 0.8599 . ?
O8 H8B 0.8598 . ?
C16 C17 1.495(12) . ?
C8 H8 0.9400 . ?
C8 C9 1.439(11) . ?
C29 H29 0.9400 . ?
C29 C30 1.392(10) . ?
C12 H12 0.9400 . ?
C12 C12A 1.367(10) . ?
C12B C12A 1.495(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C27 C26 1.441(10) . ?
C7 H7 0.9900 . ?
C30 H30 0.9400 . ?
C30 C30A 1.380(10) . ?
C26 H26 0.9400 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?
C4 H4 0.9400 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
O9 H9A 0.8599 . ?
O9 H9B 0.8602 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 H36C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 H35C 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C13 114.2(6) . . ?
C10 O5 C18 119.3(6) . . ?
C19 O10 C31 116.0(7) . . ?
C28 O14 C36 119.7(6) . . ?
C2 O2 C14 115.1(6) . . ?
C20 O11 C32 115.8(6) . . ?
C21 O12 C33 117.0(6) . . ?
C3 O3 C15 118.0(7) . . ?
C34 N2 H2 119.8 . . ?
C34 N2 C25 120.4(6) . . ?
C25 N2 H2 119.8 . . ?
C16 N1 H1 118.1 . . ?
C16 N1 C7 123.8(7) . . ?
C7 N1 H1 118.1 . . ?
H7A O7 H7B 104.5 . . ?
O10 C19 C20 119.3(6) . . ?
O10 C19 C30B 119.6(6) . . ?
C20 C19 C30B 121.1(6) . . ?
C30B C22A C23 118.9(7) . . ?
C22 C22A C30B 120.6(7) . . ?
C22 C22A C23 120.5(6) . . ?
O11 C20 C21 121.6(7) . . ?
C19 C20 O11 118.6(6) . . ?
C19 C20 C21 119.7(7) . . ?
O15 C34 N2 122.3(7) . . ?
O15 C34 C35 121.8(8) . . ?
N2 C34 C35 115.9(7) . . ?
C26 C25A C25 116.1(6) . . ?
C26 C25A C30A 129.2(7) . . ?
C30A C25A C25 114.6(6) . . ?
C19 C30B C30A 121.7(6) . . ?
C22A C30B C19 118.1(7) . . ?
C22A C30B C30A 120.2(6) . . ?
C12B C4A C4 120.7(7) . . ?
C12B C4A C5 118.8(7) . . ?
C4 C4A C5 120.4(7) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.4(6) . . ?
C10 C11 H11 114.5 . . ?
C10 C11 C12 131.0(7) . . ?
C12 C11 H11 114.5 . . ?
C8 C7A C12A 127.1(7) . . ?
C8 C7A C7 117.7(6) . . ?
C12A C7A C7 115.2(6) . . ?
C22A C22 H22 119.5 . . ?
C22A C22 C21 121.1(7) . . ?
C21 C22 H22 119.5 . . ?
O12 C21 C20 114.4(6) . . ?
O12 C21 C22 126.3(7) . . ?
C22 C21 C20 119.3(7) . . ?
O1 C1 C12B 119.4(6) . . ?
O1 C1 C2 119.3(6) . . ?
C2 C1 C12B 121.0(6) . . ?
O5 C10 C11 123.5(7) . . ?
O5 C10 C9 109.2(6) . . ?
C11 C10 C9 127.2(7) . . ?
N2 C25 C25A 113.5(6) . . ?
N2 C25 H25 106.9 . . ?
N2 C25 C24 111.8(6) . . ?
C25A C25 H25 106.9 . . ?
C24 C25 C25A 110.3(6) . . ?
C24 C25 H25 106.9 . . ?
O14 C28 C27 109.8(6) . . ?
C29 C28 O14 122.0(7) . . ?
C29 C28 C27 128.1(7) . . ?
O3 C3 C2 115.9(7) . . ?
O3 C3 C4 123.5(7) . . ?
C2 C3 C4 120.6(7) . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C23 C24 C25 113.5(6) . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H8A O8 H8B 104.5 . . ?
O6 C16 N1 122.7(8) . . ?
O6 C16 C17 121.9(8) . . ?
N1 C16 C17 115.4(8) . . ?
C7A C8 H8 112.1 . . ?
C7A C8 C9 135.9(7) . . ?
C9 C8 H8 112.1 . . ?
O4 C9 C10 118.8(7) . . ?
O4 C9 C8 119.6(7) . . ?
C8 C9 C10 121.7(7) . . ?
C28 C29 H29 114.5 . . ?
C28 C29 C30 130.9(7) . . ?
C30 C29 H29 114.5 . . ?
C11 C12 H12 113.6 . . ?
C12A C12 C11 132.8(7) . . ?
C12A C12 H12 113.6 . . ?
C4A C12B C1 117.9(7) . . ?
C4A C12B C12A 119.5(6) . . ?
C1 C12B C12A 122.7(6) . . ?
C7A C12A C12B 117.4(6) . . ?
C12 C12A C7A 123.8(7) . . ?
C12 C12A C12B 118.7(7) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O13 C27 C28 119.5(7) . . ?
O13 C27 C26 118.2(7) . . ?
C26 C27 C28 122.2(7) . . ?
N1 C7 C6 108.6(6) . . ?
N1 C7 C7A 113.9(6) . . ?
N1 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
C7A C7 C6 110.5(6) . . ?
C7A C7 H7 107.9 . . ?
C29 C30 H30 114.1 . . ?
C30A C30 C29 131.8(7) . . ?
C30A C30 H30 114.1 . . ?
C25A C26 C27 133.3(7) . . ?
C25A C26 H26 113.4 . . ?
C27 C26 H26 113.4 . . ?
C25A C30A C30B 119.1(6) . . ?
C30 C30A C25A 123.4(7) . . ?
C30 C30A C30B 117.5(7) . . ?
O2 C2 C1 118.1(6) . . ?
C3 C2 O2 122.1(7) . . ?
C3 C2 C1 119.7(7) . . ?
O12 C33 H33A 109.5 . . ?
O12 C33 H33B 109.5 . . ?
O12 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C4A C4 H4 120.0 . . ?
C3 C4 C4A 120.0(7) . . ?
C3 C4 H4 120.0 . . ?
C22A C23 H23A 109.3 . . ?
C22A C23 H23B 109.3 . . ?
C24 C23 C22A 111.6(6) . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C4A C5 C6 111.5(6) . . ?
C4A C5 H5A 109.3 . . ?
C4A C5 H5B 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
H9A O9 H9B 104.5 . . ?
O14 C36 H36A 109.5 . . ?
O14 C36 H36B 109.5 . . ?
O14 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O11 C32 H32A 109.5 . . ?
O11 C32 H32B 109.5 . . ?
O11 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O10 C31 H31A 109.5 . . ?
O10 C31 H31B 109.5 . . ?
O10 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22019996_0ma
_database_code_depnum_ccdc_archive 'CCDC 2027394'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        tropone
_chemical_formula_moiety         '2(C5 H3 O3 S), 2(H2 O), 2(C7 H7 O)'
_chemical_formula_sum            'C24 H24 O10 S2'
_chemical_formula_weight         536.55
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4803(5)
_cell_length_b                   12.7831(4)
_cell_length_c                   12.1312(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.7390(10)
_cell_angle_gamma                90
_cell_volume                     2399.49(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6858
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.9589.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22183
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         2.315
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'D8 ADVENTURE'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3817
_reflns_number_total             4785
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.625
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+2.3667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O10(H10a,H10b), O5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C21(H21), C11(H11), C9(H9), C19(H19), C22(H22), C10(H10), C7(H7),
 C18(H18), C14(H14), C6(H6a), C5(H5), C17(H17), C2(H2), C15(H15), C16(H16),
 C4(H4), C3(H3)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6), O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
S2 S 0.31711(3) 0.35282(4) 0.53991(5) 0.02597(15) Uani 1 1 d . . . . .
S1 S 0.17446(4) 0.84478(5) 0.44080(5) 0.02962(15) Uani 1 1 d . . . . .
O9 O 0.22856(10) 0.38399(13) 0.51684(14) 0.0342(4) Uani 1 1 d . . . . .
O8 O 0.34361(10) 0.26563(12) 0.47063(13) 0.0325(4) Uani 1 1 d . . . . .
O7 O 0.33586(11) 0.33219(14) 0.65615(13) 0.0382(4) Uani 1 1 d . . . . .
O10 O 0.22976(11) 0.24417(15) 0.79642(15) 0.0416(5) Uani 1 1 d . . . . .
H10A H 0.2630 0.2464 0.8555 0.062 Uiso 1 1 d G . . . .
H10B H 0.2614 0.2697 0.7448 0.062 Uiso 1 1 d G . . . .
O4 O 0.14270(11) 0.81203(14) 0.33215(14) 0.0386(4) Uani 1 1 d . . . . .
O3 O 0.26454(10) 0.87635(14) 0.44141(15) 0.0397(4) Uani 1 1 d . . . . .
O2 O 0.15594(11) 0.76877(14) 0.52555(15) 0.0416(4) Uani 1 1 d . . . . .
O6 O 0.19100(11) 0.05768(15) 0.76147(15) 0.0440(5) Uani 1 1 d . . . . .
H6 H 0.1978 0.1216 0.7755 0.066 Uiso 1 1 calc GR . . . .
O1 O 0.42471(12) 0.68406(14) 0.70688(15) 0.0434(5) Uani 1 1 d . . . . .
H1 H 0.3711 0.6751 0.6996 0.065 Uiso 1 1 calc GR . . . .
O5 O 0.26480(14) 0.6823(2) 0.67662(18) 0.0794(9) Uani 1 1 d . . . . .
H5A H 0.2327 0.6878 0.7339 0.119 Uiso 1 1 d G . . . .
H5B H 0.2410 0.7164 0.6216 0.119 Uiso 1 1 d G . . . .
C24 C 0.47548(13) 0.45609(16) 0.51760(17) 0.0229(4) Uani 1 1 d . . . . .
C23 C 0.48033(14) 0.63186(17) 0.43599(18) 0.0271(5) Uani 1 1 d . . . . .
H23 H 0.5126 0.6903 0.4118 0.032 Uiso 1 1 calc R . . . .
C20 C 0.38333(13) 0.46075(17) 0.50380(17) 0.0240(5) Uani 1 1 d . . . . .
C21 C 0.34348(14) 0.54734(18) 0.45967(18) 0.0284(5) Uani 1 1 d . . . . .
H21 H 0.2822 0.5493 0.4519 0.034 Uiso 1 1 calc R . . . .
C1 C 0.45910(15) 0.60487(18) 0.76037(18) 0.0286(5) Uani 1 1 d . . . . .
C13 C 0.11329(14) 0.02906(19) 0.78810(18) 0.0297(5) Uani 1 1 d . . . . .
C11 C 0.02546(15) 1.14108(19) 0.53042(19) 0.0315(5) Uani 1 1 d . . . . .
H11 H -0.0036 1.2032 0.5510 0.038 Uiso 1 1 calc R . . . .
C9 C 0.15699(15) 1.05150(18) 0.4879(2) 0.0330(5) Uani 1 1 d . . . . .
H9 H 0.2177 1.0541 0.4787 0.040 Uiso 1 1 calc R . . . .
C12 C 0.02267(14) 0.95380(17) 0.48552(18) 0.0271(5) Uani 1 1 d . . . . .
C8 C 0.11385(14) 0.95876(18) 0.47341(18) 0.0283(5) Uani 1 1 d . . . . .
C19 C 0.05996(15) 0.10241(18) 0.8401(2) 0.0316(5) Uani 1 1 d . . . . .
H19 H 0.0860 0.1680 0.8567 0.038 Uiso 1 1 calc R . . . .
C22 C 0.39252(15) 0.63349(18) 0.42573(19) 0.0316(5) Uani 1 1 d . . . . .
H22 H 0.3642 0.6933 0.3954 0.038 Uiso 1 1 calc R . . . .
C10 C 0.11221(15) 1.14326(19) 0.5164(2) 0.0325(5) Uani 1 1 d . . . . .
H10 H 0.1430 1.2071 0.5259 0.039 Uiso 1 1 calc R . . . .
C7 C 0.40622(15) 0.52436(19) 0.79853(19) 0.0315(5) Uani 1 1 d . . . . .
H7 H 0.3462 0.5319 0.7815 0.038 Uiso 1 1 calc R . . . .
C18 C -0.02424(15) 0.0920(2) 0.8698(2) 0.0370(6) Uani 1 1 d . . . . .
H18 H -0.0480 0.1515 0.9046 0.044 Uiso 1 1 calc R . . . .
C14 C 0.09131(17) -0.0745(2) 0.7609(2) 0.0387(6) Uani 1 1 d . . . . .
H14 H 0.1362 -0.1151 0.7308 0.046 Uiso 1 1 calc R . . . .
C6 C 0.42893(18) 0.43682(19) 0.8566(2) 0.0389(6) Uani 1 1 d . . . . .
H6A H 0.3820 0.3929 0.8751 0.047 Uiso 1 1 calc R . . . .
C5 C 0.5097(2) 0.4017(2) 0.8930(2) 0.0478(7) Uani 1 1 d . . . . .
H5 H 0.5104 0.3374 0.9323 0.057 Uiso 1 1 calc R . . . .
C17 C -0.08045(16) 0.0071(2) 0.8568(2) 0.0443(7) Uani 1 1 d . . . . .
H17 H -0.1375 0.0175 0.8813 0.053 Uiso 1 1 calc R . . . .
C2 C 0.54959(17) 0.6108(2) 0.7746(2) 0.0433(6) Uani 1 1 d . . . . .
H2 H 0.5759 0.6707 0.7439 0.052 Uiso 1 1 calc R . . . .
C15 C 0.01441(19) -0.1249(2) 0.7719(2) 0.0473(7) Uani 1 1 d . . . . .
H15 H 0.0137 -0.1955 0.7475 0.057 Uiso 1 1 calc R . . . .
C16 C -0.06362(19) -0.0889(2) 0.8133(3) 0.0505(7) Uani 1 1 d . . . . .
H16 H -0.1104 -0.1371 0.8108 0.061 Uiso 1 1 calc R . . . .
C4 C 0.5874(2) 0.4472(3) 0.8796(2) 0.0576(9) Uani 1 1 d . . . . .
H4 H 0.6361 0.4106 0.9097 0.069 Uiso 1 1 calc R . . . .
C3 C 0.60460(18) 0.5421(3) 0.8266(3) 0.0576(9) Uani 1 1 d . . . . .
H3 H 0.6638 0.5616 0.8270 0.069 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
S2 O9 1.4467(17) . ?
S2 O8 1.4621(16) . ?
S2 O7 1.4551(17) . ?
S2 C20 1.781(2) . ?
S1 O4 1.4543(17) . ?
S1 O3 1.4514(17) . ?
S1 O2 1.4495(18) . ?
S1 C8 1.784(2) . ?
O10 H10A 0.8701 . ?
O10 H10B 0.8701 . ?
O6 H6 0.8400 . ?
O6 C13 1.307(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.307(3) . ?
O5 H5A 0.8695 . ?
O5 H5B 0.8703 . ?
C24 C24 1.428(4) 3_666 ?
C24 C23 1.423(3) 3_666 ?
C24 C20 1.433(3) . ?
C23 C24 1.423(3) 3_666 ?
C23 H23 0.9500 . ?
C23 C22 1.362(3) . ?
C20 C21 1.368(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.406(3) . ?
C1 C7 1.402(3) . ?
C1 C2 1.408(3) . ?
C13 C19 1.411(3) . ?
C13 C14 1.403(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.433(3) 3_576 ?
C11 C10 1.359(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.369(3) . ?
C9 C10 1.411(3) . ?
C12 C11 1.433(3) 3_576 ?
C12 C12 1.423(4) 3_576 ?
C12 C8 1.425(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.369(3) . ?
C22 H22 0.9500 . ?
C10 H10 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.363(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.397(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.364(4) . ?
C6 H6A 0.9500 . ?
C6 C5 1.387(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.351(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.364(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.364(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.400(4) . ?
C16 H16 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.403(5) . ?
C3 H3 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
O9 S2 O8 112.30(9) . . ?
O9 S2 O7 113.41(10) . . ?
O9 S2 C20 106.74(10) . . ?
O8 S2 C20 105.99(10) . . ?
O7 S2 O8 111.58(10) . . ?
O7 S2 C20 106.22(10) . . ?
O4 S1 C8 105.69(10) . . ?
O3 S1 O4 112.52(10) . . ?
O3 S1 C8 106.47(11) . . ?
O2 S1 O4 112.40(11) . . ?
O2 S1 O3 113.17(10) . . ?
O2 S1 C8 105.87(11) . . ?
H10A O10 H10B 104.5 . . ?
C13 O6 H6 109.5 . . ?
C1 O1 H1 109.5 . . ?
H5A O5 H5B 109.5 . . ?
C24 C24 C20 118.0(2) 3_666 . ?
C23 C24 C24 119.1(2) 3_666 3_666 ?
C23 C24 C20 122.95(19) 3_666 . ?
C24 C23 H23 119.5 3_666 . ?
C22 C23 C24 121.0(2) . 3_666 ?
C22 C23 H23 119.5 . . ?
C24 C20 S2 121.17(16) . . ?
C21 C20 S2 117.83(17) . . ?
C21 C20 C24 121.0(2) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(2) . . ?
C22 C21 H21 119.8 . . ?
O1 C1 C7 119.9(2) . . ?
O1 C1 C2 114.1(2) . . ?
C7 C1 C2 125.9(2) . . ?
O6 C13 C19 118.7(2) . . ?
O6 C13 C14 115.1(2) . . ?
C14 C13 C19 126.2(2) . . ?
C12 C11 H11 119.6 3_576 . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(2) . 3_576 ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C12 C12 C11 118.5(2) 3_576 3_576 ?
C12 C12 C8 119.1(2) 3_576 . ?
C8 C12 C11 122.4(2) . 3_576 ?
C9 C8 S1 118.54(18) . . ?
C9 C8 C12 120.4(2) . . ?
C12 C8 S1 121.06(17) . . ?
C13 C19 H19 115.6 . . ?
C18 C19 C13 128.9(2) . . ?
C18 C19 H19 115.6 . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C1 C7 H7 115.5 . . ?
C6 C7 C1 129.0(2) . . ?
C6 C7 H7 115.5 . . ?
C19 C18 H18 115.1 . . ?
C19 C18 C17 129.8(2) . . ?
C17 C18 H18 115.1 . . ?
C13 C14 H14 115.5 . . ?
C15 C14 C13 129.0(3) . . ?
C15 C14 H14 115.5 . . ?
C7 C6 H6A 114.9 . . ?
C7 C6 C5 130.2(3) . . ?
C5 C6 H6A 114.9 . . ?
C6 C5 H5 115.9 . . ?
C4 C5 C6 128.3(3) . . ?
C4 C5 H5 115.9 . . ?
C18 C17 H17 116.0 . . ?
C16 C17 C18 128.1(3) . . ?
C16 C17 H17 116.0 . . ?
C1 C2 H2 115.6 . . ?
C3 C2 C1 128.8(3) . . ?
C3 C2 H2 115.6 . . ?
C14 C15 H15 114.9 . . ?
C14 C15 C16 130.2(3) . . ?
C16 C15 H15 114.9 . . ?
C17 C16 C15 127.7(3) . . ?
C17 C16 H16 116.2 . . ?
C15 C16 H16 116.2 . . ?
C5 C4 H4 116.2 . . ?
C5 C4 C3 127.6(3) . . ?
C3 C4 H4 116.2 . . ?
C2 C3 C4 130.1(3) . . ?
C2 C3 H3 115.0 . . ?
C4 C3 H3 115.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_22020146_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2027392'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        tropone
_chemical_formula_moiety         'C10 H7 O3 S, C7 H7 O, H2 O'
_chemical_formula_sum            'C17 H16 O5 S'
_chemical_formula_weight         332.36
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.7177(11)
_cell_length_b                   16.233(3)
_cell_length_c                   14.530(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.666(5)
_cell_angle_gamma                90
_cell_volume                     1566.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.494
_cell_measurement_theta_min      2.510
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 18039 reflections, Rint = 0.0730
 (7203 with I > 3sig(I), Rint = 0.0566)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.1049
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6222
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_min         1.893
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2025
_reflns_number_total             3216
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    ?
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3216
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+1.9247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1490
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4A) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(O4A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Others
 Fixed Sof: O3(0.88) O4(0.88) O2(0.88) O4A(0.12) O2A(0.12) O3A(0.12)
4.a Free rotating group:
 O5(H5A,H5B)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C2(H2), C13(H13), C14(H14), C16(H16), C15(H15),
 C3(H3), C7(H7), C4(H4), C6(H6), C5(H5)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.75679(13) 0.45847(5) 0.81071(6) 0.0311(2) Uani 1 1 d . . . . .
O1 O 0.2426(4) 0.70044(16) 0.70862(15) 0.0414(6) Uani 1 1 d . . . . .
H1 H 0.2281 0.6494 0.7143 0.062 Uiso 1 1 calc GR . . . .
O5 O 0.2312(4) 0.54837(18) 0.73730(19) 0.0512(7) Uani 1 1 d . . . . .
H5A H 0.3441 0.5302 0.7659 0.077 Uiso 1 1 d G . . . .
H5B H 0.1346 0.5307 0.7647 0.077 Uiso 1 1 d G . . . .
O3 O 0.9313(5) 0.51222(19) 0.8355(2) 0.0472(8) Uani 0.88 1 d . . P A 1
O4 O 0.7312(5) 0.42727(18) 0.71869(17) 0.0454(8) Uani 0.88 1 d . . P A 1
O2 O 0.5750(5) 0.49853(19) 0.8366(2) 0.0502(8) Uani 0.88 1 d . . P A 1
C8 C 0.7749(4) 0.2956(2) 0.8538(2) 0.0280(7) Uani 1 1 d . . . . .
H8 H 0.7429 0.2869 0.7886 0.034 Uiso 1 1 calc R . . . .
C9 C 0.7961(4) 0.3732(2) 0.8874(2) 0.0264(7) Uani 1 1 d . . . . .
C10 C 0.8454(5) 0.3883(2) 0.9844(2) 0.0288(7) Uani 1 1 d . . . . .
H10 H 0.8603 0.4433 1.0069 0.035 Uiso 1 1 calc R . . . .
C11 C 0.8713(5) 0.3238(2) 1.0452(2) 0.0305(8) Uani 1 1 d . . . . .
H11 H 0.9052 0.3340 1.1101 0.037 Uiso 1 1 calc R . . . .
C17 C 0.8002(4) 0.2258(2) 0.9157(2) 0.0269(7) Uani 1 1 d . . . . .
C12 C 0.8480(4) 0.2418(2) 1.0123(2) 0.0270(7) Uani 1 1 d . . . . .
C2 C 0.1798(5) 0.6579(2) 0.5521(2) 0.0306(8) Uani 1 1 d . . . . .
H2 H 0.1947 0.6031 0.5750 0.037 Uiso 1 1 calc R . . . .
C13 C 0.8725(5) 0.1733(2) 1.0753(2) 0.0340(8) Uani 1 1 d . . . . .
H13 H 0.9044 0.1827 1.1404 0.041 Uiso 1 1 calc R . . . .
C1 C 0.2068(5) 0.7204(2) 0.6203(2) 0.0299(8) Uani 1 1 d . . . . .
C14 C 0.8501(5) 0.0944(2) 1.0419(3) 0.0371(9) Uani 1 1 d . . . . .
H14 H 0.8648 0.0492 1.0840 0.045 Uiso 1 1 calc R . . . .
C16 C 0.7815(5) 0.1444(2) 0.8836(2) 0.0336(8) Uani 1 1 d . . . . .
H16 H 0.7522 0.1338 0.8187 0.040 Uiso 1 1 calc R . . . .
C15 C 0.8051(5) 0.0799(2) 0.9451(3) 0.0369(8) Uani 1 1 d . . . . .
H15 H 0.7911 0.0250 0.9224 0.044 Uiso 1 1 calc R . . . .
C3 C 0.1349(5) 0.6657(2) 0.4573(2) 0.0366(8) Uani 1 1 d . . . . .
H3 H 0.1242 0.6151 0.4240 0.044 Uiso 1 1 calc R . . . .
C7 C 0.2008(5) 0.8068(2) 0.6035(3) 0.0365(9) Uani 1 1 d . . . . .
H7 H 0.2278 0.8408 0.6572 0.044 Uiso 1 1 calc R . . . .
C4 C 0.1026(5) 0.7359(3) 0.4020(3) 0.0434(10) Uani 1 1 d . . . . .
H4 H 0.0667 0.7266 0.3370 0.052 Uiso 1 1 calc R . . . .
C6 C 0.1612(5) 0.8474(2) 0.5204(3) 0.0466(10) Uani 1 1 d . . . . .
H6 H 0.1648 0.9057 0.5247 0.056 Uiso 1 1 calc R . . . .
C5 C 0.1158(5) 0.8158(3) 0.4291(3) 0.0474(11) Uani 1 1 d . . . . .
H5 H 0.0915 0.8556 0.3807 0.057 Uiso 1 1 calc R . . . .
O4A O 0.914(3) 0.4425(11) 0.7366(11) 0.025(4) Uani 0.12 1 d . U P A 2
O2A O 0.561(3) 0.4505(12) 0.7510(13) 0.030(4) Uani 0.12 1 d . U P A 2
O3A O 0.802(4) 0.5245(14) 0.8602(17) 0.051(6) Uani 0.12 1 d . U P A 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 O3 1.462(3) . ?
S1 O4 1.416(3) . ?
S1 O2 1.481(3) . ?
S1 C9 1.772(3) . ?
S1 O4A 1.639(17) . ?
S1 O2A 1.468(17) . ?
S1 O3A 1.30(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.310(4) . ?
O5 H5A 0.8600 . ?
O5 H5B 0.8603 . ?
C8 H8 0.9500 . ?
C8 C9 1.351(4) . ?
C8 C17 1.441(4) . ?
C9 C10 1.420(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.364(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.415(5) . ?
C17 C12 1.416(4) . ?
C17 C16 1.401(5) . ?
C12 C13 1.434(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.410(4) . ?
C2 C3 1.372(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.371(5) . ?
C1 C7 1.424(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.414(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.369(5) . ?
C15 H15 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.393(5) . ?
C7 H7 0.9500 . ?
C7 C6 1.366(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.355(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.411(6) . ?
C5 H5 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
O3 S1 O2 109.65(19) . . ?
O3 S1 C9 105.87(16) . . ?
O4 S1 O3 115.15(19) . . ?
O4 S1 O2 114.18(19) . . ?
O4 S1 C9 107.46(16) . . ?
O2 S1 C9 103.50(16) . . ?
O4A S1 C9 103.9(6) . . ?
O2A S1 C9 109.8(7) . . ?
O2A S1 O4A 102.0(10) . . ?
O3A S1 C9 107.2(11) . . ?
O3A S1 O4A 111.9(14) . . ?
O3A S1 O2A 120.8(14) . . ?
C1 O1 H1 109.5 . . ?
H5A O5 H5B 109.5 . . ?
C9 C8 H8 119.6 . . ?
C9 C8 C17 120.8(3) . . ?
C17 C8 H8 119.6 . . ?
C8 C9 S1 120.3(2) . . ?
C8 C9 C10 121.0(3) . . ?
C10 C9 S1 118.7(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C12 C17 C8 117.5(3) . . ?
C16 C17 C8 122.5(3) . . ?
C16 C17 C12 120.0(3) . . ?
C11 C12 C17 120.4(3) . . ?
C11 C12 C13 121.2(3) . . ?
C17 C12 C13 118.5(3) . . ?
C1 C2 H2 115.6 . . ?
C3 C2 H2 115.6 . . ?
C3 C2 C1 128.7(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
O1 C1 C2 119.7(3) . . ?
O1 C1 C7 114.0(3) . . ?
C2 C1 C7 126.2(3) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C2 C3 H3 114.9 . . ?
C2 C3 C4 130.3(4) . . ?
C4 C3 H3 114.9 . . ?
C1 C7 H7 115.7 . . ?
C6 C7 C1 128.5(4) . . ?
C6 C7 H7 115.7 . . ?
C3 C4 H4 115.9 . . ?
C5 C4 C3 128.2(4) . . ?
C5 C4 H4 115.9 . . ?
C7 C6 H6 115.0 . . ?
C7 C6 C5 130.0(4) . . ?
C5 C6 H6 115.0 . . ?
C4 C5 C6 128.0(4) . . ?
C4 C5 H5 116.0 . . ?
C6 C5 H5 116.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_220191031_0m
_database_code_depnum_ccdc_archive 'CCDC 2027397'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2020-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        tropolone
_chemical_formula_moiety         'C10 H7 O3 S, C7 H7 O2, 3(H2 O)'
_chemical_formula_sum            'C17 H20 O8 S'
_chemical_formula_weight         384.39
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7888(4)
_cell_length_b                   20.0960(12)
_cell_length_c                   13.5491(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.749(2)
_cell_angle_gamma                90
_cell_volume                     1802.90(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.354
_cell_measurement_theta_min      2.546
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0633 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.9112. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.378
_diffrn_reflns_theta_min         2.546
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2765
_reflns_number_total             3683
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.348
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     509
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+2.9544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1493
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 S1-C19 \\sim S1-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Fixed Sof: C9(0.65) C8(0.65) H8A(0.65) C13(0.65) H13(0.65) C12(0.65)
 C10(0.65) H10(0.65) C16(0.65) H16(0.65) C15(0.65) H15(0.65) C11(0.65)
 H11(0.65) C27(0.35) C22(0.35) C23(0.35) H23(0.35) C24(0.35) H24(0.35)
 C25(0.35) H25(0.35) C26(0.35) H26(0.35) C18(0.35) H18(0.35) C19(0.35)
 C20(0.35) H20(0.35) C21(0.35) H21(0.35) C14(0.65) H14(0.65) C17(0.65)
6.a Free rotating group:
 O6(H6a,H6b), O7(H7a,H7b)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C5(H5), C4(H4), C8(H8A), C13(H13), C10(H10), C16(H16),
  C15(H15), C11(H11), C23(H23), C24(H24), C25(H25), C26(H26), C18(H18),
 C20(H20), C21(H21), C14(H14)
6.c Fitted hexagon refined as free rotating group:
 C27(C22,C23,C24,C25,C26)
6.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.44242(12) 0.14426(4) 0.75007(7) 0.0332(2) Uani 1 1 d D U . . .
O5 O 0.2433(4) 0.13525(13) 0.68481(19) 0.0446(6) Uani 1 1 d . U . . .
O2 O 0.9819(4) 0.43931(12) 0.69251(18) 0.0395(6) Uani 1 1 d . U . . .
H2 H 1.0135 0.4747 0.7250 0.059 Uiso 1 1 calc GR . . . .
O6 O 0.8148(4) 0.42399(14) 0.4787(2) 0.0454(7) Uani 1 1 d . U . . .
H6A H 0.8028 0.4651 0.4966 0.068 Uiso 1 1 d G . . . .
H6B H 0.7039 0.4115 0.4374 0.068 Uiso 1 1 d G . . . .
O3 O 0.6030(4) 0.12690(12) 0.7006(2) 0.0465(7) Uani 1 1 d . U . . .
O1 O 0.8969(4) 0.32642(13) 0.60576(19) 0.0453(7) Uani 1 1 d . U . . .
H1 H 0.8865 0.3658 0.5846 0.068 Uiso 1 1 calc GR . . . .
O8 O 0.2280(5) 0.44530(16) 0.4754(2) 0.0500(8) Uani 1 1 d . U . . .
O7 O 0.9480(4) 0.44761(14) 0.2236(3) 0.0574(8) Uani 1 1 d . U . . .
H7A H 1.0347 0.4178 0.2139 0.086 Uiso 1 1 d G . . . .
H7B H 0.8395 0.4280 0.2331 0.086 Uiso 1 1 d G . . . .
O4 O 0.4600(4) 0.11211(16) 0.8468(2) 0.0591(8) Uani 1 1 d . U . . .
C2 C 0.9991(5) 0.38857(18) 0.7565(3) 0.0334(8) Uani 1 1 d . U . . .
C1 C 0.9508(5) 0.32636(19) 0.7059(3) 0.0358(8) Uani 1 1 d . U . . .
C6 C 1.0012(6) 0.2468(2) 0.8515(4) 0.0525(11) Uani 1 1 d . U . . .
H6 H 0.9934 0.2005 0.8645 0.063 Uiso 1 1 calc R . . . .
C7 C 0.9562(5) 0.2645(2) 0.7502(3) 0.0449(9) Uani 1 1 d . U . . .
H7 H 0.9242 0.2284 0.7041 0.054 Uiso 1 1 calc R . . . .
C3 C 1.0580(5) 0.3994(2) 0.8596(3) 0.0419(9) Uani 1 1 d . U . . .
H3 H 1.0853 0.4444 0.8793 0.050 Uiso 1 1 calc R . . . .
C5 C 1.0550(6) 0.2858(3) 0.9352(3) 0.0548(11) Uani 1 1 d . U . . .
H5 H 1.0756 0.2638 0.9987 0.066 Uiso 1 1 calc R . . . .
C4 C 1.0829(5) 0.3539(3) 0.9382(3) 0.0526(11) Uani 1 1 d . U . . .
H4 H 1.1256 0.3724 1.0041 0.063 Uiso 1 1 calc R . . . .
C9 C 0.4645(9) 0.2327(3) 0.7607(5) 0.0231(12) Uani 0.65 1 d D U P A 1
C8 C 0.5188(7) 0.2616(3) 0.8546(4) 0.0228(10) Uani 0.65 1 d . U P A 1
H8A H 0.5395 0.2344 0.9134 0.027 Uiso 0.65 1 calc R . P A 1
C13 C 0.5383(14) 0.4405(3) 0.7870(6) 0.0368(16) Uani 0.65 1 d . U P A 1
H13 H 0.5147 0.4680 0.7286 0.044 Uiso 0.65 1 calc R . P A 1
C12 C 0.5110(9) 0.3708(3) 0.7753(5) 0.0267(12) Uani 0.65 1 d . U P A 1
C10 C 0.4312(7) 0.2732(3) 0.6719(4) 0.0264(11) Uani 0.65 1 d . U P A 1
H10 H 0.3940 0.2530 0.6070 0.032 Uiso 0.65 1 calc R . P A 1
C16 C 0.6020(8) 0.3616(3) 0.9600(4) 0.0311(11) Uani 0.65 1 d . U P A 1
H16 H 0.6224 0.3352 1.0196 0.037 Uiso 0.65 1 calc R . P A 1
C15 C 0.6292(13) 0.4295(3) 0.9674(6) 0.0397(15) Uani 0.65 1 d . U P A 1
H15 H 0.6697 0.4494 1.0323 0.048 Uiso 0.65 1 calc R . P A 1
C11 C 0.4519(7) 0.3394(3) 0.6795(4) 0.0293(11) Uani 0.65 1 d . U P A 1
H11 H 0.4266 0.3657 0.6198 0.035 Uiso 0.65 1 calc R . P A 1
C27 C 0.4998(17) 0.3392(4) 0.7845(8) 0.039(3) Uani 0.35 1 d . U P A 2
C22 C 0.558(2) 0.3493(5) 0.8883(8) 0.038(3) Uani 0.35 1 d G U P A 2
C23 C 0.594(2) 0.4135(6) 0.9265(7) 0.049(3) Uani 0.35 1 d G U P A 2
H23 H 0.6345 0.4204 0.9975 0.059 Uiso 0.35 1 calc R . P A 2
C24 C 0.572(3) 0.4674(4) 0.8608(9) 0.053(5) Uani 0.35 1 d G U P A 2
H24 H 0.5968 0.5113 0.8869 0.064 Uiso 0.35 1 calc R . P A 2
C25 C 0.514(2) 0.4573(4) 0.7570(9) 0.046(4) Uani 0.35 1 d G U P A 2
H25 H 0.4982 0.4942 0.7121 0.055 Uiso 0.35 1 calc R . P A 2
C26 C 0.4774(14) 0.3932(5) 0.7188(7) 0.045(2) Uani 0.35 1 d G U P A 2
H26 H 0.4374 0.3863 0.6478 0.054 Uiso 0.35 1 calc R . P A 2
C18 C 0.4609(15) 0.2729(7) 0.7410(11) 0.034(2) Uani 0.35 1 d . U P A 2
H18 H 0.4217 0.2654 0.6701 0.041 Uiso 0.35 1 calc R . P A 2
C19 C 0.485(2) 0.2232(6) 0.8086(10) 0.033(2) Uani 0.35 1 d D U P A 2
C20 C 0.5436(15) 0.2302(5) 0.9136(8) 0.035(2) Uani 0.35 1 d . U P A 2
H20 H 0.5588 0.1925 0.9570 0.042 Uiso 0.35 1 calc R . P A 2
C21 C 0.5782(15) 0.2924(6) 0.9514(9) 0.042(2) Uani 0.35 1 d . U P A 2
H21 H 0.6171 0.2982 1.0227 0.050 Uiso 0.35 1 calc R . P A 2
C14 C 0.5984(18) 0.4692(4) 0.8815(7) 0.044(2) Uani 0.65 1 d . U P A 1
H14 H 0.6187 0.5159 0.8877 0.053 Uiso 0.65 1 calc R . P A 1
C17 C 0.5445(12) 0.3315(3) 0.8653(5) 0.0228(13) Uani 0.65 1 d . U P A 1
H8B H 0.118(7) 0.433(2) 0.470(3) 0.057(15) Uiso 1 1 d . . . . .
H8C H 0.279(8) 0.428(3) 0.426(4) 0.087(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.454(2) . ?
S1 O3 1.443(2) . ?
S1 O4 1.443(3) . ?
S1 C9 1.786(6) . ?
S1 C19 1.769(12) . ?
O2 H2 0.8400 . ?
O2 C2 1.327(4) . ?
O6 H6A 0.8701 . ?
O6 H6B 0.8700 . ?
O1 H1 0.8400 . ?
O1 C1 1.325(4) . ?
O8 H8B 0.77(5) . ?
O8 H8C 0.89(6) . ?
O7 H7A 0.8697 . ?
O7 H7B 0.8700 . ?
C2 C1 1.429(5) . ?
C2 C3 1.382(5) . ?
C1 C7 1.378(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(6) . ?
C6 C5 1.361(6) . ?
C7 H7 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.385(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(6) . ?
C4 H4 0.9500 . ?
C9 C8 1.373(8) . ?
C9 C10 1.429(8) . ?
C8 H8A 0.9500 . ?
C8 C17 1.418(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.417(9) . ?
C13 C14 1.382(10) . ?
C12 C11 1.419(8) . ?
C12 C17 1.428(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.340(7) . ?
C16 H16 0.9500 . ?
C16 C15 1.377(8) . ?
C16 C17 1.395(8) . ?
C15 H15 0.9500 . ?
C15 C14 1.389(10) . ?
C11 H11 0.9500 . ?
C27 C22 1.3900 . ?
C27 C26 1.3900 . ?
C27 C18 1.457(14) . ?
C22 C23 1.3900 . ?
C22 C21 1.417(14) . ?
C23 H23 0.9500 . ?
C23 C24 1.3900 . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C26 H26 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.341(17) . ?
C19 C20 1.397(16) . ?
C20 H20 0.9500 . ?
C20 C21 1.352(15) . ?
C21 H21 0.9500 . ?
C14 H14 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
O5 S1 C9 102.9(2) . . ?
O5 S1 C19 114.9(5) . . ?
O3 S1 O5 112.55(16) . . ?
O3 S1 C9 102.7(2) . . ?
O3 S1 C19 111.2(5) . . ?
O4 S1 O5 112.10(16) . . ?
O4 S1 O3 113.25(17) . . ?
O4 S1 C9 112.5(3) . . ?
O4 S1 C19 91.2(5) . . ?
C2 O2 H2 109.5 . . ?
H6A O6 H6B 109.5 . . ?
C1 O1 H1 109.5 . . ?
H8B O8 H8C 110(5) . . ?
H7A O7 H7B 109.5 . . ?
O2 C2 C1 112.4(3) . . ?
O2 C2 C3 120.2(3) . . ?
C3 C2 C1 127.4(4) . . ?
O1 C1 C2 118.2(3) . . ?
O1 C1 C7 114.9(3) . . ?
C7 C1 C2 126.8(4) . . ?
C7 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C5 C6 C7 129.7(4) . . ?
C1 C7 C6 129.9(4) . . ?
C1 C7 H7 115.0 . . ?
C6 C7 H7 115.0 . . ?
C2 C3 H3 115.4 . . ?
C2 C3 C4 129.2(4) . . ?
C4 C3 H3 115.4 . . ?
C6 C5 H5 116.4 . . ?
C6 C5 C4 127.3(4) . . ?
C4 C5 H5 116.4 . . ?
C3 C4 H4 115.2 . . ?
C5 C4 C3 129.6(4) . . ?
C5 C4 H4 115.2 . . ?
C8 C9 S1 119.8(5) . . ?
C8 C9 C10 120.0(6) . . ?
C10 C9 S1 120.2(4) . . ?
C9 C8 H8A 119.5 . . ?
C9 C8 C17 121.0(5) . . ?
C17 C8 H8A 119.5 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C14 C13 C12 121.5(6) . . ?
C13 C12 C11 123.1(6) . . ?
C13 C12 C17 117.3(6) . . ?
C11 C12 C17 119.6(6) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 H10 119.8 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(6) . . ?
C17 C16 H16 119.9 . . ?
C16 C15 H15 119.5 . . ?
C16 C15 C14 121.1(7) . . ?
C14 C15 H15 119.5 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.0(5) . . ?
C10 C11 H11 119.5 . . ?
C22 C27 C26 120.0 . . ?
C22 C27 C18 121.9(9) . . ?
C26 C27 C18 118.1(9) . . ?
C27 C22 C21 117.4(9) . . ?
C23 C22 C27 120.0 . . ?
C23 C22 C21 122.6(9) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C18 H18 122.6 . . ?
C19 C18 C27 114.9(12) . . ?
C19 C18 H18 122.6 . . ?
C18 C19 S1 112.2(10) . . ?
C18 C19 C20 125.8(11) . . ?
C20 C19 S1 121.9(10) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 C19 117.8(11) . . ?
C21 C20 H20 121.1 . . ?
C22 C21 H21 118.9 . . ?
C20 C21 C22 122.2(11) . . ?
C20 C21 H21 118.9 . . ?
C13 C14 C15 119.7(7) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C8 C17 C12 117.9(6) . . ?
C16 C17 C8 121.7(5) . . ?
C16 C17 C12 120.4(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
