# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20180911dy-655-430
_database_code_depnum_ccdc_archive 'CCDC 1874184'
loop_
_audit_author_name
_audit_author_address
'Yi Dong'
;Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College
China
;
_audit_update_record             
;
2018-10-19 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;
_audit_creation_date             2018-09-11
_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        
'dimethyl 2-(5-(N-acetylsulfamoyl)-2-(thiazol-2-yl)-4-(trifluoromethoxy)phenyl)malonate'
_chemical_formula_moiety         'C17 H15 F3 N2 O8 S2'
_chemical_formula_sum            'C17 H15 F3 N2 O8 S2'
_chemical_formula_weight         496.43
_chemical_melting_point          443
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0043(3)
_cell_length_b                   10.7993(4)
_cell_length_c                   12.4643(5)
_cell_angle_alpha                95.266(3)
_cell_angle_beta                 100.867(3)
_cell_angle_gamma                92.113(3)
_cell_volume                     1052.02(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4368
_cell_measurement_temperature    296.00(18)
_cell_measurement_theta_max      71.1810
_cell_measurement_theta_min      4.0970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light pink'
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6999
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.316
_diffrn_reflns_theta_min         3.629
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  13.00   1.00    1.00    --  -40.81  57.00 150.00   81
  2  ω   -110.00 -21.00   1.00    1.00    --  -40.81 -57.00-150.00   89
  3  ω    -69.00  30.00   1.00    1.00    --  -40.81  57.00   0.00   99
  4  ω      1.00  27.00   1.00    1.00    --   40.81 -99.00  90.00   26
  5  ω     95.00 120.00   1.00    1.00    --  100.91 125.00  30.00   25
  6  ω     94.00 159.00   1.00    1.00    --  100.91 125.00 150.00   65
  7  ω     29.00  55.00   1.00    1.00    --  100.91 -45.00  60.00   26
  8  ω     82.00 170.00   1.00    1.00    --  100.91  30.00 150.00   88
  9  ω     84.00 171.00   1.00    1.00    --  100.91  61.00-150.00   87
 10  ω     42.00 110.00   1.00    1.00    --  100.91 -95.00  90.00   68
 11  ω    113.00 169.00   1.00    1.00    --  100.91 125.00  90.00   56
 12  ω     60.00 127.00   1.00    1.00    --  100.91 -45.00  60.00   67
 13  ω     52.00 113.00   1.00    1.00    --  100.91-125.00  60.00   61
 14  ω     91.00 118.00   1.00    1.00    --  100.91-125.00 -60.00   27
 15  ω     45.00 130.00   1.00    1.00    --  100.91 -77.00-180.00   85
 16  ω     43.00 119.00   1.00    1.00    --  100.91 -30.00-180.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0376374000
_diffrn_orient_matrix_UB_12      0.1048457000
_diffrn_orient_matrix_UB_13      0.0951650000
_diffrn_orient_matrix_UB_21      -0.1887318000
_diffrn_orient_matrix_UB_22      -0.0073366000
_diffrn_orient_matrix_UB_23      0.0105169000
_diffrn_orient_matrix_UB_31      0.0386078000
_diffrn_orient_matrix_UB_32      -0.0976721000
_diffrn_orient_matrix_UB_33      0.0826706000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3554
_reflns_number_total             3965
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.058
_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)+(0.0684P)²+0.4167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1269
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), N6(H6), C14(H14), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.02623(7) 0.14071(4) 0.63125(4) 0.04358(17) Uani 1 1 d . . . . .
S2 S 0.33572(9) 0.51841(6) 1.12185(5) 0.0603(2) Uani 1 1 d . . . . .
O1 O -0.0473(2) 0.65852(14) 0.73040(15) 0.0521(4) Uani 1 1 d . . . . .
O2 O 0.1527(2) 0.80843(13) 0.73465(14) 0.0535(4) Uani 1 1 d . . . . .
C3 C 0.1924(2) 0.45977(17) 0.90229(16) 0.0354(4) Uani 1 1 d . . . . .
O4 O 0.0809(3) 0.12178(14) 0.87593(14) 0.0583(4) Uani 1 1 d . . . . .
C5 C 0.1344(3) 0.37945(17) 0.71170(16) 0.0365(4) Uani 1 1 d . . . . .
H5 H 0.1246 0.3924 0.6381 0.044 Uiso 1 1 calc R . . . .
N6 N 0.1759(2) 0.04143(15) 0.64239(15) 0.0419(4) Uani 1 1 d . . . . .
H6 H 0.1515 -0.0319 0.6586 0.050 Uiso 1 1 calc R . . . .
C7 C 0.1106(3) 0.70203(17) 0.74056(16) 0.0380(4) Uani 1 1 d . . . . .
C8 C 0.0986(3) 0.26100(17) 0.73879(17) 0.0376(4) Uani 1 1 d . . . . .
C9 C 0.1845(2) 0.47945(17) 0.79123(15) 0.0333(4) Uani 1 1 d . . . . .
C10 C 0.2415(2) 0.60413(17) 0.75802(15) 0.0344(4) Uani 1 1 d . . . . .
H10 H 0.3323 0.6401 0.8181 0.041 Uiso 1 1 calc R . . . .
O11 O 0.2157(2) 0.60060(19) 0.56617(13) 0.0631(5) Uani 1 1 d . . . . .
O12 O 0.0147(3) 0.19552(15) 0.53099(13) 0.0614(5) Uani 1 1 d . . . . .
O13 O -0.1190(2) 0.07580(16) 0.65382(17) 0.0627(5) Uani 1 1 d . . . . .
C14 C 0.1548(3) 0.34031(19) 0.92863(17) 0.0422(5) Uani 1 1 d . . . . .
H14 H 0.1570 0.3271 1.0016 0.051 Uiso 1 1 calc R . . . .
C15 C 0.3225(2) 0.58484(18) 0.65673(16) 0.0368(4) Uani 1 1 d . . . . .
C16 C 0.2452(3) 0.55786(19) 0.99384(16) 0.0384(4) Uani 1 1 d . . . . .
O17 O 0.3847(3) 0.17118(16) 0.60981(17) 0.0661(5) Uani 1 1 d . . . . .
F18 F 0.1538(4) -0.04651(15) 0.94479(17) 0.1092(8) Uani 1 1 d . . . . .
N19 N 0.2301(3) 0.67674(17) 0.98826(16) 0.0539(5) Uani 1 1 d . . . . .
C20 C 0.1147(3) 0.24218(18) 0.84863(18) 0.0422(5) Uani 1 1 d . . . . .
O21 O 0.4636(2) 0.5549(2) 0.65996(15) 0.0760(6) Uani 1 1 d . . . . .
C22 C 0.3399(3) 0.0682(2) 0.6273(2) 0.0496(5) Uani 1 1 d . . . . .
F23 F 0.2501(4) 0.12213(18) 1.03902(16) 0.1279(10) Uani 1 1 d . . . . .
F24 F 0.3440(3) 0.0646(2) 0.8950(2) 0.1098(7) Uani 1 1 d . . . . .
C25 C 0.3549(4) 0.6714(3) 1.1703(2) 0.0590(6) Uani 1 1 d . . . . .
H25 H 0.4014 0.7027 1.2422 0.071 Uiso 1 1 calc R . . . .
C26 C 0.2928(4) 0.7399(2) 1.0893(2) 0.0611(7) Uani 1 1 d . . . . .
H26 H 0.2923 0.8262 1.1009 0.073 Uiso 1 1 calc R . . . .
C27 C 0.2066(5) 0.0682(2) 0.9386(2) 0.0747(9) Uani 1 1 d . . . . .
C28 C -0.1765(4) 0.7493(3) 0.7061(3) 0.0705(8) Uani 1 1 d . . . . .
H28A H -0.1778 0.7739 0.6339 0.106 Uiso 1 1 calc GR . . . .
H28B H -0.1502 0.8211 0.7590 0.106 Uiso 1 1 calc GR . . . .
H28C H -0.2862 0.7127 0.7094 0.106 Uiso 1 1 calc GR . . . .
C29 C 0.2846(4) 0.5872(4) 0.4664(2) 0.0865(11) Uani 1 1 d . . . . .
H29A H 0.1979 0.6018 0.4050 0.130 Uiso 1 1 calc GR . . . .
H29B H 0.3223 0.5044 0.4556 0.130 Uiso 1 1 calc GR . . . .
H29C H 0.3791 0.6464 0.4725 0.130 Uiso 1 1 calc GR . . . .
C1 C 0.4527(4) -0.0401(3) 0.6360(3) 0.0774(9) Uani 1 1 d . . . . .
H1A H 0.4503 -0.0752 0.7037 0.116 Uiso 1 1 calc GR . . . .
H1B H 0.5673 -0.0121 0.6343 0.116 Uiso 1 1 calc GR . . . .
H1C H 0.4124 -0.1022 0.5755 0.116 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 N6 1.6320(18) . ?
S1 C8 1.775(2) . ?
S1 O12 1.4201(17) . ?
S1 O13 1.4218(18) . ?
S2 C16 1.722(2) . ?
S2 C25 1.697(3) . ?
O1 C7 1.312(3) . ?
O1 C28 1.460(3) . ?
O2 C7 1.198(2) . ?
C3 C9 1.410(3) . ?
C3 C14 1.396(3) . ?
C3 C16 1.472(3) . ?
O4 C20 1.403(2) . ?
O4 C27 1.337(4) . ?
C5 C8 1.386(3) . ?
C5 C9 1.390(3) . ?
N6 C22 1.385(3) . ?
C7 C10 1.517(3) . ?
C8 C20 1.385(3) . ?
C9 C10 1.523(2) . ?
C10 C15 1.526(3) . ?
O11 C15 1.310(3) . ?
O11 C29 1.450(3) . ?
C14 C20 1.371(3) . ?
C15 O21 1.180(3) . ?
C16 N19 1.301(3) . ?
O17 C22 1.207(3) . ?
F18 C27 1.308(3) . ?
N19 C26 1.372(3) . ?
C22 C1 1.503(4) . ?
F23 C27 1.309(4) . ?
F24 C27 1.315(4) . ?
C25 C26 1.338(4) . ?

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
N6 S1 C8 105.00(9) . . ?
O12 S1 N6 110.03(11) . . ?
O12 S1 C8 106.88(9) . . ?
O12 S1 O13 119.73(12) . . ?
O13 S1 N6 105.33(10) . . ?
O13 S1 C8 108.97(11) . . ?
C25 S2 C16 89.66(11) . . ?
C7 O1 C28 115.13(18) . . ?
C9 C3 C16 123.52(17) . . ?
C14 C3 C9 119.04(18) . . ?
C14 C3 C16 117.40(17) . . ?
C27 O4 C20 117.8(2) . . ?
C8 C5 C9 121.99(18) . . ?
C22 N6 S1 123.92(15) . . ?
O1 C7 C10 114.10(16) . . ?
O2 C7 O1 124.8(2) . . ?
O2 C7 C10 121.12(19) . . ?
C5 C8 S1 118.69(15) . . ?
C20 C8 S1 122.57(15) . . ?
C20 C8 C5 118.70(18) . . ?
C3 C9 C10 121.54(17) . . ?
C5 C9 C3 118.48(17) . . ?
C5 C9 C10 119.83(17) . . ?
C7 C10 C9 117.72(16) . . ?
C7 C10 C15 109.24(15) . . ?
C9 C10 C15 110.56(15) . . ?
C15 O11 C29 115.60(19) . . ?
C20 C14 C3 121.01(19) . . ?
O11 C15 C10 112.25(17) . . ?
O21 C15 C10 123.44(19) . . ?
O21 C15 O11 124.27(19) . . ?
C3 C16 S2 119.83(14) . . ?
N19 C16 S2 114.44(16) . . ?
N19 C16 C3 125.73(18) . . ?
C16 N19 C26 109.6(2) . . ?
C8 C20 O4 118.60(19) . . ?
C14 C20 O4 120.72(19) . . ?
C14 C20 C8 120.60(18) . . ?
N6 C22 C1 114.2(2) . . ?
O17 C22 N6 121.3(2) . . ?
O17 C22 C1 124.5(2) . . ?
C26 C25 S2 109.58(18) . . ?
C25 C26 N19 116.7(2) . . ?
F18 C27 O4 107.6(3) . . ?
F18 C27 F23 107.5(2) . . ?
F18 C27 F24 108.0(3) . . ?
F23 C27 O4 114.0(3) . . ?
F23 C27 F24 108.0(3) . . ?
F24 C27 O4 111.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.768
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, hexane'
####################################################################### 
# 
# 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_20181015dongyi
_database_code_depnum_ccdc_archive 'CCDC 1874186'
loop_
_audit_author_name
_audit_author_address
'Yi Dong'
;Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College
China
;
_audit_update_record             
;
2018-10-19 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;
_audit_creation_date             2018-10-18
_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         'C17 H16 F3 N2 O8 S2, H2 O'
_chemical_formula_sum            'C17 H18 F3 N2 O9 S2'
_chemical_formula_weight         515.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3787(4)
_cell_length_b                   10.6208(5)
_cell_length_c                   11.4671(6)
_cell_angle_alpha                85.869(4)
_cell_angle_beta                 72.343(4)
_cell_angle_gamma                71.018(4)
_cell_volume                     1028.77(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3388
_cell_measurement_temperature    109.5(5)
_cell_measurement_theta_max      70.8420
_cell_measurement_theta_min      4.0350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6843
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.269
_diffrn_reflns_theta_min         4.047
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.5(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -33.00   1.00    1.00    --  -40.81 -38.00  90.00   81
  2  ω   -107.00  -8.00   1.00    1.00    --  -40.81 -77.00-150.00   99
  3  ω    -87.00  -2.00   1.00    1.00    --  -40.81 125.00 -30.00   85
  4  ω      2.00  50.00   1.00    1.00    --   40.81 -99.00 -30.00   48
  5  ω    136.00 174.00   1.00    1.00    --  100.91  45.00   0.00   38
  6  ω     29.00 117.00   1.00    1.00    --  100.91-125.00 150.00   88
  7  ω    122.00 154.00   1.00    1.00    --  100.91  45.00 -90.00   32
  8  ω    110.00 137.00   1.00    1.00    --  100.91 125.00-180.00   27
  9  ω     77.00 120.00   1.00    1.00    --  100.91  45.00   0.00   43
 10  ω     79.00 108.00   1.00    1.00    --  100.91 -95.00-180.00   29
 11  ω     74.00 163.00   1.00    1.00    --  100.91  77.00 120.00   89
 12  ω     73.00 177.00   1.00    1.00    --  100.91  30.00  60.00  104
 13  ω     87.00 113.00   1.00    1.00    --  100.91-125.00 -30.00   26
 14  ω     30.00  97.00   1.00    1.00    --  100.91 -61.00-150.00   67
 15  ω    100.00 169.00   1.00    1.00    --  100.91 125.00 -60.00   69
 16  ω     25.00 133.00   1.00    1.00    --  100.91 -77.00 -60.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062742000
_diffrn_orient_matrix_UB_12      -0.1194132000
_diffrn_orient_matrix_UB_13      0.0837650000
_diffrn_orient_matrix_UB_21      -0.1800110000
_diffrn_orient_matrix_UB_22      0.0638583000
_diffrn_orient_matrix_UB_23      0.0535019000
_diffrn_orient_matrix_UB_31      -0.0254036000
_diffrn_orient_matrix_UB_32      -0.0721993000
_diffrn_orient_matrix_UB_33      -0.1000800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3346
_reflns_number_total             3854
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.075
_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     304
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.027
_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)+(0.0626P)²+1.2049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H1B-H13
 2.45 with sigma of 0.01
3.a Free rotating group:
 O1(H1A,H1B)
3.b Ternary CH refined with riding coordinates:
 C25(H25)
3.c Aromatic/amide H refined with riding coordinates:
 N11(H11), N13(H13), C14(H14), C15(H15), C23(H23), C29(H29)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.05887(7) 0.53450(6) 0.68370(6) 0.02160(17) Uani 1 1 d . . . . .
S2 S -0.01830(8) 0.90168(7) 1.20508(6) 0.02501(18) Uani 1 1 d . . . . .
F1 F -0.39715(19) 0.62231(18) 0.96646(16) 0.0346(4) Uani 1 1 d . . . . .
O2 O -0.1890(2) 0.6799(2) 0.88818(17) 0.0273(4) Uani 1 1 d . . . . .
O3 O 0.6146(2) 0.62662(18) 0.68125(18) 0.0247(4) Uani 1 1 d . . . . .
O4 O 0.5268(2) 0.45234(18) 0.73672(19) 0.0263(4) Uani 1 1 d . . . . .
O5 O 0.4554(2) 0.71714(19) 0.46683(17) 0.0261(4) Uani 1 1 d . . . . .
O6 O 0.3301(2) 0.86916(19) 0.62139(17) 0.0270(4) Uani 1 1 d . . . . .
O7 O -0.0106(2) 0.44240(19) 0.7557(2) 0.0324(5) Uani 1 1 d . . . . .
O8 O 0.2025(2) 0.4827(2) 0.5878(2) 0.0355(5) Uani 1 1 d . . . . .
O9 O 0.0637(2) 0.7714(2) 0.53696(18) 0.0297(5) Uani 1 1 d . . . . .
F10 F -0.3744(2) 0.7815(2) 1.0529(2) 0.0596(7) Uani 1 1 d . . . . .
N11 N -0.0760(2) 0.6328(2) 0.62511(19) 0.0191(4) Uani 1 1 d . . . . .
H11 H -0.1621 0.6147 0.6363 0.023 Uiso 1 1 calc R . . . .
C12 C 0.1057(3) 0.7883(2) 0.9683(2) 0.0166(5) Uani 1 1 d . . . . .
N13 N 0.2419(3) 0.9081(2) 1.05011(19) 0.0204(5) Uani 1 1 d . . . . .
H13 H 0.3205 0.8975 0.9848 0.024 Uiso 1 1 calc DR . . . .
C14 C 0.2236(3) 0.9732(2) 1.1551(2) 0.0226(5) Uani 1 1 d . . . . .
H14 H 0.2978 1.0103 1.1626 0.027 Uiso 1 1 calc R . . . .
C15 C 0.2323(3) 0.7406(2) 0.8646(2) 0.0174(5) Uani 1 1 d . . . . .
H15 H 0.3266 0.7563 0.8572 0.021 Uiso 1 1 calc R . . . .
C16 C 0.1216(3) 0.8640(2) 1.0636(2) 0.0169(5) Uani 1 1 d . . . . .
C17 C 0.2225(3) 0.6700(2) 0.7713(2) 0.0168(5) Uani 1 1 d . . . . .
C18 C 0.5172(3) 0.5719(2) 0.6927(2) 0.0168(5) Uani 1 1 d . . . . .
C19 C 0.3785(3) 0.7561(3) 0.5828(2) 0.0204(5) Uani 1 1 d . . . . .
C20 C 0.0826(3) 0.6416(2) 0.7844(2) 0.0170(5) Uani 1 1 d . . . . .
C21 C -0.0464(3) 0.6946(2) 0.8883(2) 0.0183(5) Uani 1 1 d . . . . .
C22 C -0.0576(3) 0.7436(3) 0.5584(2) 0.0218(5) Uani 1 1 d . . . . .
C23 C -0.0365(3) 0.7669(2) 0.9794(2) 0.0191(5) Uani 1 1 d . . . . .
H23 H -0.1237 0.8009 1.0471 0.023 Uiso 1 1 calc R . . . .
F24 F -0.2296(3) 0.5858(3) 1.0675(2) 0.0690(8) Uani 1 1 d . . . . .
C25 C 0.3653(3) 0.6342(2) 0.6581(2) 0.0185(5) Uani 1 1 d . . . . .
H25 H 0.3542 0.5696 0.6073 0.022 Uiso 1 1 calc R . . . .
C26 C 0.6740(3) 0.3779(3) 0.7602(3) 0.0268(6) Uani 1 1 d . . . . .
H26A H 0.7573 0.3572 0.6841 0.040 Uiso 1 1 calc GR . . . .
H26B H 0.6651 0.2968 0.7996 0.040 Uiso 1 1 calc GR . . . .
H26C H 0.6974 0.4303 0.8123 0.040 Uiso 1 1 calc GR . . . .
C27 C 0.4825(4) 0.8201(3) 0.3826(3) 0.0330(7) Uani 1 1 d . . . . .
H27A H 0.5601 0.7803 0.3075 0.050 Uiso 1 1 calc GR . . . .
H27B H 0.5197 0.8778 0.4178 0.050 Uiso 1 1 calc GR . . . .
H27C H 0.3856 0.8708 0.3662 0.050 Uiso 1 1 calc GR . . . .
C28 C -0.2944(3) 0.6669(3) 0.9932(3) 0.0246(6) Uani 1 1 d . . . . .
C29 C 0.0908(3) 0.9803(3) 1.2474(2) 0.0251(6) Uani 1 1 d . . . . .
H29 H 0.0630 1.0222 1.3232 0.030 Uiso 1 1 calc R . . . .
C30 C -0.1989(4) 0.8220(3) 0.5197(3) 0.0298(6) Uani 1 1 d . . . . .
H30A H -0.1847 0.9036 0.4846 0.045 Uiso 1 1 calc GR . . . .
H30B H -0.2912 0.8420 0.5897 0.045 Uiso 1 1 calc GR . . . .
H30C H -0.2115 0.7709 0.4601 0.045 Uiso 1 1 calc GR . . . .
O1 O 0.4452(4) 0.9656(3) 0.8084(3) 0.0596(8) Uani 1 1 d . . . . .
H1A H 0.4046 0.9298 0.7686 0.089 Uiso 1 1 d G . . . .
H1B H 0.3865 1.0465 0.8191 0.089 Uiso 1 1 d DG . . . .


_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 1.427(2) . ?
S1 O8 1.426(2) . ?
S1 N11 1.642(2) . ?
S1 C20 1.785(2) . ?
S2 C16 1.724(3) . ?
S2 C29 1.701(3) . ?
F1 C28 1.321(3) . ?
O2 C21 1.396(3) . ?
O2 C28 1.338(3) . ?
O3 C18 1.205(3) . ?
O4 C18 1.317(3) . ?
O4 C26 1.445(3) . ?
O5 C19 1.328(3) . ?
O5 C27 1.440(4) . ?
O6 C19 1.201(3) . ?
O9 C22 1.216(3) . ?
F10 C28 1.314(3) . ?
N11 C22 1.387(3) . ?
C12 C15 1.386(3) . ?
C12 C16 1.472(3) . ?
C12 C23 1.391(3) . ?
N13 C14 1.369(3) . ?
N13 C16 1.321(3) . ?
C14 C29 1.352(4) . ?
C15 C17 1.391(3) . ?
C17 C20 1.403(3) . ?
C17 C25 1.519(3) . ?
C18 C25 1.522(3) . ?
C19 C25 1.521(4) . ?
C20 C21 1.407(3) . ?
C21 C23 1.382(4) . ?
C22 C30 1.494(4) . ?
F24 C28 1.306(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
O7 S1 N11 105.99(11) . . ?
O7 S1 C20 108.34(12) . . ?
O8 S1 O7 118.20(13) . . ?
O8 S1 N11 109.02(13) . . ?
O8 S1 C20 110.13(11) . . ?
N11 S1 C20 104.19(11) . . ?
C29 S2 C16 89.56(13) . . ?
C28 O2 C21 120.6(2) . . ?
C18 O4 C26 116.1(2) . . ?
C19 O5 C27 116.3(2) . . ?
C22 N11 S1 123.06(18) . . ?
C15 C12 C16 119.8(2) . . ?
C15 C12 C23 119.4(2) . . ?
C23 C12 C16 120.8(2) . . ?
C16 N13 C14 110.2(2) . . ?
C29 C14 N13 115.8(2) . . ?
C12 C15 C17 121.9(2) . . ?
C12 C16 S2 121.84(19) . . ?
N13 C16 S2 114.10(18) . . ?
N13 C16 C12 124.0(2) . . ?
C15 C17 C20 119.2(2) . . ?
C15 C17 C25 116.3(2) . . ?
C20 C17 C25 124.4(2) . . ?
O3 C18 O4 125.1(2) . . ?
O3 C18 C25 123.5(2) . . ?
O4 C18 C25 111.4(2) . . ?
O5 C19 C25 108.8(2) . . ?
O6 C19 O5 125.1(3) . . ?
O6 C19 C25 126.1(2) . . ?
C17 C20 S1 124.86(19) . . ?
C17 C20 C21 118.0(2) . . ?
C21 C20 S1 117.03(18) . . ?
O2 C21 C20 115.6(2) . . ?
C23 C21 O2 121.9(2) . . ?
C23 C21 C20 122.2(2) . . ?
O9 C22 N11 121.1(3) . . ?
O9 C22 C30 125.3(3) . . ?
N11 C22 C30 113.6(2) . . ?
C21 C23 C12 119.1(2) . . ?
C17 C25 C18 111.1(2) . . ?
C17 C25 C19 111.5(2) . . ?
C19 C25 C18 108.4(2) . . ?
F1 C28 O2 108.0(2) . . ?
F10 C28 F1 107.1(2) . . ?
F10 C28 O2 112.1(2) . . ?
F24 C28 F1 109.6(2) . . ?
F24 C28 O2 112.8(2) . . ?
F24 C28 F10 107.2(3) . . ?
C14 C29 S2 110.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.761
