# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_I
_audit_block_doi                 10.5517/ccdc.csd.cc2b8rhw
_database_code_depnum_ccdc_archive 'CCDC 2153368'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1107/S2414314622001997 2022
#Added by publCIF



_audit_update_record             
;
2022-02-19 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_iucr_compatibility_tag          ACTA95
_publcif_datablock.id            {29721a57-5e2d-4f3f-a1af-48c4ccae498a}


# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N O5'
_chemical_formula_sum            'C23 H19 N O5'
_chemical_formula_weight         389.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.7089(8)
_cell_length_b                   14.3510(12)
_cell_length_c                   14.2749(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.946(10)
_cell_angle_gamma                90
_cell_volume                     1902.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2883
_cell_measurement_theta_min      2.9845
_cell_measurement_theta_max      29.1084

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysalisPro (Agilent, 2014)'
#;
#CrysAlisPro, Agilent Technologies,
#Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
#Empirical absorption correction using spherical harmonics,
# implemented in SCALE3 ABSPACK scaling algorithm.
#;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_reflns_number            10689
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.991
_diffrn_reflns_theta_max         29.173
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4413
_reflns_number_gt                3119
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlis PRO (Agilent, 2014)
;
_computing_cell_refinement       
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction        
;
CrysAlis PRO (Agilent, 2014)
;
_computing_structure_solution    
;
SHELXT (Sheldrick, 2015)
;
_computing_structure_refinement  
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020) and
Mercury
(Macrae et al.,  2020)
;
_computing_publication_material  
;
ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020) and
Mercury
(Macrae et al.,  2020)
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

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 0.53859(10) 0.16733(8) 0.92065(7) 0.0410(3) Uani 1 1 d . . . . .
O2 O 0.63028(12) 0.27465(8) 0.84841(8) 0.0509(3) Uani 1 1 d . . . . .
C14 C 0.44382(14) 0.18379(10) 0.74486(11) 0.0347(3) Uani 1 1 d . . . . .
O5 O 0.27716(13) -0.06937(8) 0.61784(10) 0.0595(4) Uani 1 1 d . . . . .
C15 C 0.36436(14) 0.09212(10) 0.73953(10) 0.0332(3) Uani 1 1 d . . . . .
H15 H 0.431514 0.042889 0.734017 0.040 Uiso 1 1 calc R U . . .
O3 O 0.50815(13) 0.31695(9) 0.66833(9) 0.0588(4) Uani 1 1 d . . . . .
H3 H 0.561932 0.325224 0.723781 0.088 Uiso 1 1 calc R U . . .
C9 C 0.42029(14) 0.11197(10) 0.92053(11) 0.0337(3) Uani 1 1 d . . . . .
C10 C 0.32907(15) 0.07558(10) 0.83485(11) 0.0347(3) Uani 1 1 d . . . . .
C7 C 0.29134(15) 0.04148(11) 1.02203(11) 0.0366(4) Uani 1 1 d . . . . .
C4 C 0.27309(15) 0.02080(11) 1.11980(11) 0.0382(4) Uani 1 1 d . . . . .
C19 C 0.28311(17) 0.11903(13) 0.55664(11) 0.0447(4) Uani 1 1 d . . . . .
H19A H 0.360887 0.079214 0.550748 0.054 Uiso 1 1 calc R U . . .
H19B H 0.203779 0.112652 0.497179 0.054 Uiso 1 1 calc R U . . .
C16 C 0.11816(17) 0.14945(12) 0.65498(12) 0.0450(4) Uani 1 1 d . . . . .
C13 C 0.54193(15) 0.21194(11) 0.83729(11) 0.0375(4) Uani 1 1 d . . . . .
C20 C 0.23367(15) 0.08697(11) 0.64512(11) 0.0377(4) Uani 1 1 d . . . . .
C8 C 0.40422(15) 0.09584(10) 1.01183(11) 0.0366(4) Uani 1 1 d . . . . .
H8 H 0.469369 0.121527 1.066950 0.044 Uiso 1 1 calc R U . . .
C21 C 0.17320(17) -0.01170(12) 0.62229(11) 0.0437(4) Uani 1 1 d . . . . .
O4 O 0.05006(13) -0.03278(10) 0.60776(10) 0.0649(4) Uani 1 1 d . . . . .
C12 C 0.19570(17) 0.00624(12) 0.93635(12) 0.0443(4) Uani 1 1 d . . . . .
H12 H 0.117331 -0.029036 0.940506 0.053 Uiso 1 1 calc R U . . .
C18 C 0.33369(17) 0.21905(12) 0.56740(12) 0.0467(4) Uani 1 1 d . . . . .
H18A H 0.381800 0.232559 0.518170 0.056 Uiso 1 1 calc R U . . .
H18B H 0.250752 0.259856 0.555766 0.056 Uiso 1 1 calc R U . . .
C17 C 0.43402(16) 0.23902(11) 0.66616(12) 0.0410(4) Uani 1 1 d . . . . .
C11 C 0.21487(17) 0.02259(12) 0.84563(12) 0.0443(4) Uani 1 1 d . . . . .
H11 H 0.149569 -0.002549 0.790253 0.053 Uiso 1 1 calc R U . . .
C6 C 0.20395(18) -0.05906(13) 1.13558(13) 0.0507(4) Uani 1 1 d . . . . .
H6 H 0.166517 -0.099657 1.083600 0.061 Uiso 1 1 calc R U . . .
C3 C 0.32765(18) 0.08032(12) 1.19927(12) 0.0466(4) Uani 1 1 d . . . . .
H3A H 0.375026 0.134713 1.191218 0.056 Uiso 1 1 calc R U . . .
C2 C 0.2424(2) -0.02057(16) 1.30377(15) 0.0627(5) Uani 1 1 d . . . . .
H2 H 0.231601 -0.034154 1.364935 0.075 Uiso 1 1 calc R U . . .
C1 C 0.1887(2) -0.08045(15) 1.22642(15) 0.0637(5) Uani 1 1 d . . . . .
H1 H 0.142442 -0.135050 1.235243 0.076 Uiso 1 1 calc R U . . .
C5 C 0.3116(2) 0.05875(15) 1.29030(14) 0.0579(5) Uani 1 1 d . . . . .
H5 H 0.348412 0.098916 1.342756 0.070 Uiso 1 1 calc R U . . .
C22 C 0.2376(2) -0.16616(14) 0.59282(18) 0.0714(6) Uani 1 1 d . . . . .
H22A H 0.150569 -0.169084 0.538150 0.086 Uiso 1 1 calc R U . . .
H22B H 0.220030 -0.197877 0.648226 0.086 Uiso 1 1 calc R U . . .
C23 C 0.3565(3) -0.21069(18) 0.5666(2) 0.1099(10) Uani 1 1 d . . . . .
H23A H 0.372605 -0.179133 0.511451 0.165 Uiso 1 1 calc R U . . .
H23B H 0.333040 -0.274743 0.550071 0.165 Uiso 1 1 calc R U . . .
H23C H 0.442123 -0.207456 0.621170 0.165 Uiso 1 1 calc R U . . .
N1 N 0.03398(17) 0.20167(13) 0.66178(13) 0.0658(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.3599(18) . ?
O1 C9 1.3961(17) . ?
O2 C13 1.2212(18) . ?
C14 C17 1.355(2) . ?
C14 C13 1.442(2) . ?
C14 C15 1.516(2) . ?
O5 C21 1.321(2) . ?
O5 C22 1.457(2) . ?
C15 C10 1.516(2) . ?
C15 C20 1.5604(19) . ?
O3 C17 1.3255(19) . ?
C9 C8 1.377(2) . ?
C9 C10 1.386(2) . ?
C10 C11 1.390(2) . ?
C7 C8 1.387(2) . ?
C7 C12 1.397(2) . ?
C7 C4 1.487(2) . ?
C4 C6 1.379(2) . ?
C4 C3 1.395(2) . ?
C19 C18 1.510(2) . ?
C19 C20 1.546(2) . ?
C16 N1 1.134(2) . ?
C16 C20 1.474(2) . ?
C20 C21 1.531(2) . ?
C21 O4 1.1913(18) . ?
C12 C11 1.381(2) . ?
C18 C17 1.489(2) . ?
C6 C1 1.382(2) . ?
C3 C5 1.388(2) . ?
C2 C5 1.363(3) . ?
C2 C1 1.376(3) . ?
C22 C23 1.460(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
C13 O1 C9 119.76(11) . . ?
C17 C14 C13 117.57(14) . . ?
C17 C14 C15 123.65(13) . . ?
C13 C14 C15 118.68(13) . . ?
C21 O5 C22 117.30(14) . . ?
C14 C15 C10 109.62(12) . . ?
C14 C15 C20 111.00(12) . . ?
C10 C15 C20 115.36(12) . . ?
C8 C9 C10 123.53(14) . . ?
C8 C9 O1 114.50(12) . . ?
C10 C9 O1 121.96(13) . . ?
C9 C10 C11 115.70(14) . . ?
C9 C10 C15 118.66(13) . . ?
C11 C10 C15 125.57(13) . . ?
C8 C7 C12 117.11(14) . . ?
C8 C7 C4 121.65(13) . . ?
C12 C7 C4 121.25(14) . . ?
C6 C4 C3 117.61(15) . . ?
C6 C4 C7 121.05(15) . . ?
C3 C4 C7 121.33(15) . . ?
C18 C19 C20 111.65(14) . . ?
N1 C16 C20 176.08(18) . . ?
O2 C13 O1 115.36(13) . . ?
O2 C13 C14 125.24(14) . . ?
O1 C13 C14 119.40(13) . . ?
C16 C20 C21 109.13(13) . . ?
C16 C20 C19 108.83(12) . . ?
C21 C20 C19 107.00(13) . . ?
C16 C20 C15 109.78(13) . . ?
C21 C20 C15 113.11(12) . . ?
C19 C20 C15 108.88(12) . . ?
C9 C8 C7 120.33(13) . . ?
O4 C21 O5 125.08(16) . . ?
O4 C21 C20 125.09(16) . . ?
O5 C21 C20 109.79(13) . . ?
C11 C12 C7 121.50(15) . . ?
C17 C18 C19 112.50(13) . . ?
O3 C17 C14 124.59(14) . . ?
O3 C17 C18 112.66(13) . . ?
C14 C17 C18 122.73(14) . . ?
C12 C11 C10 121.79(14) . . ?
C4 C6 C1 121.87(18) . . ?
C5 C3 C4 120.32(17) . . ?
C5 C2 C1 119.68(18) . . ?
C2 C1 C6 119.68(19) . . ?
C2 C5 C3 120.84(18) . . ?
O5 C22 C23 107.97(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O2 0.82 1.86 2.5702(16) 145 . yes
C11 H11 O4 0.93 2.54 3.399(2) 154 . yes
C18 H18B O1 0.97 2.60 3.4289(19) 144 4_565 yes
C19 H19B O2 0.97 2.60 3.285(2) 128 4_565 yes
C15 H15 Cg2 0.98 2.95 3.7685(17) 142 3_657 yes
C23 H23B Cg3 0.96 2.82 3.686(3) 151 2_546 yes

# Cg2 is the centroid of C1--C6
# Cg3 is the centroid of C7--C12

# [  3657] = 1-X,-Y,2-Z
# [  2546] = 1/2-X,-1/2+Y,3/2-Z


_refine_diff_density_max         0.191
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.037



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;

####################################################################### 
# 
# 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_17i
_database_code_depnum_ccdc_archive 'CCDC 2174559'
loop_
_audit_author_name
_audit_author_address
'sumair ahmad rather'
;pondicherry university
India
;
_audit_update_record             
;
2022-05-24 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-18
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H6 F3 N O6 S'
_chemical_formula_sum            'C15 H6 F3 N O6 S'
_chemical_formula_weight         385.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H6 F3 N O6 S'
_chemical_oxdiff_usercomment     'COLOURLESS PLATE , 298K,0.62 0.38 0.08'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.6654(4)
_cell_length_b                   9.6240(5)
_cell_length_c                   12.5534(7)
_cell_angle_alpha                102.129(4)
_cell_angle_beta                 104.972(5)
_cell_angle_gamma                94.329(5)
_cell_volume                     753.35(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4814
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2809
_cell_measurement_theta_min      3.1694
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16636
_diffrn_reflns_theta_full        29.35
_diffrn_reflns_theta_max         29.35
_diffrn_reflns_theta_min         3.18
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9838
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   18.00   52.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   57.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   90.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   77.0000 -180.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   25.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   81.0000  -69.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -53.00   39.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -37.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   62.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -99.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega  -86.00    4.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -57.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   25.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega  -38.00   52.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  9 omega   32.00   96.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397 -178.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
 10 omega  -50.00   50.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 11 omega  -25.00   62.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -99.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
 12 omega   35.00   96.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  178.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
 13 omega   -6.00   92.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
 14 omega   -2.00   71.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   57.0000  150.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0511624000
_diffrn_orient_matrix_UB_12      0.0500809000
_diffrn_orient_matrix_UB_13      0.0297573000
_diffrn_orient_matrix_UB_21      -0.0982558000
_diffrn_orient_matrix_UB_22      -0.0332682000
_diffrn_orient_matrix_UB_23      -0.0382272000
_diffrn_orient_matrix_UB_31      -0.0097780000
_diffrn_orient_matrix_UB_32      -0.0466612000
_diffrn_orient_matrix_UB_33      0.0357790000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2850
_reflns_number_total             3703
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0690P)²+0.3181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1408
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.05506(9) 0.07097(5) 0.85647(4) 0.04419(18) Uani 1 1 d . . .
O1 O 0.3280(2) -0.16672(15) 0.44933(12) 0.0425(3) Uani 1 1 d . . .
C2 C 0.0035(3) -0.28629(18) 0.46278(15) 0.0316(4) Uani 1 1 d . . .
O3 O 0.0371(3) 0.06871(15) 0.72890(12) 0.0496(4) Uani 1 1 d . . .
O4 O 0.4681(2) -0.24373(17) 0.31313(14) 0.0540(4) Uani 1 1 d . . .
C5 C -0.0075(3) -0.39614(18) 0.35975(15) 0.0309(4) Uani 1 1 d . . .
C6 C 0.1503(3) -0.37913(19) 0.30507(16) 0.0349(4) Uani 1 1 d . . .
C7 C 0.1707(3) -0.17456(19) 0.50161(15) 0.0342(4) Uani 1 1 d . . .
O8 O 0.2925(3) -0.46126(19) 0.14802(15) 0.0614(5) Uani 1 1 d . . .
H8 H 0.3763 -0.3889 0.1821 0.092 Uiso 1 1 calc R . .
C9 C 0.1897(3) -0.0604(2) 0.59365(16) 0.0397(4) Uani 1 1 d . . .
H9 H 0.3034 0.0121 0.6183 0.048 Uiso 1 1 calc R . .
C10 C 0.3234(3) -0.2628(2) 0.35305(17) 0.0387(4) Uani 1 1 d . . .
C11 C -0.3307(3) -0.5546(2) 0.35513(18) 0.0421(5) Uani 1 1 d . . .
C12 C -0.1449(3) -0.2798(2) 0.52425(16) 0.0387(4) Uani 1 1 d . . .
H12 H -0.2556 -0.3541 0.5031 0.046 Uiso 1 1 calc R . .
C13 C -0.1326(3) -0.1672(2) 0.61492(17) 0.0426(5) Uani 1 1 d . . .
H13 H -0.2340 -0.1642 0.6539 0.051 Uiso 1 1 calc R . .
C14 C 0.1462(3) -0.4746(2) 0.20197(18) 0.0439(5) Uani 1 1 d . . .
C15 C -0.1660(3) -0.51438(19) 0.30862(16) 0.0362(4) Uani 1 1 d . . .
C16 C 0.0339(4) -0.0593(2) 0.64638(16) 0.0396(4) Uani 1 1 d . . .
N17 N -0.4648(3) -0.5986(2) 0.38490(19) 0.0603(6) Uani 1 1 d . . .
C18 C -0.1656(4) -0.6070(2) 0.20638(19) 0.0485(5) Uani 1 1 d . . .
H18 H -0.2719 -0.6843 0.1738 0.058 Uiso 1 1 calc R . .
O19 O -0.0747(3) 0.1690(2) 0.89090(16) 0.0749(6) Uani 1 1 d . . .
O20 O 0.0484(4) -0.06695(18) 0.87525(15) 0.0846(7) Uani 1 1 d . . .
C21 C 0.3191(5) 0.1640(5) 0.9208(3) 0.0856(10) Uani 1 1 d . . .
F22 F 0.3614(4) 0.1770(3) 1.03172(17) 0.1391(11) Uani 1 1 d . . .
C23 C -0.0157(4) -0.5881(2) 0.1530(2) 0.0546(6) Uani 1 1 d . . .
H23 H -0.0213 -0.6505 0.0845 0.066 Uiso 1 1 calc R . .
F24 F 0.3352(4) 0.2898(3) 0.8978(2) 0.1320(10) Uani 1 1 d . . .
F25 F 0.4494(4) 0.0885(4) 0.8807(3) 0.1583(13) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.5701(15) . ?
S1 O19 1.404(2) . ?
S1 O20 1.3955(18) . ?
S1 C21 1.810(3) . ?
O1 C7 1.378(2) . ?
O1 C10 1.351(2) . ?
C2 C5 1.470(2) . ?
C2 C7 1.398(2) . ?
C2 C12 1.401(3) . ?
O3 C16 1.428(2) . ?
O4 C10 1.215(2) . ?
C5 C6 1.413(3) . ?
C5 C15 1.409(2) . ?
C6 C10 1.453(3) . ?
C6 C14 1.414(3) . ?
C7 C9 1.388(3) . ?
O8 H8 0.8200 . ?
O8 C14 1.336(3) . ?
C9 H9 0.9300 . ?
C9 C16 1.368(3) . ?
C11 C15 1.434(3) . ?
C11 N17 1.140(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C16 1.376(3) . ?
C14 C23 1.390(3) . ?
C15 C18 1.401(3) . ?
C18 H18 0.9300 . ?
C18 C23 1.360(3) . ?
C21 F22 1.324(4) . ?
C21 F24 1.305(4) . ?
C21 F25 1.305(4) . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 C21 99.19(13) . . ?
O19 S1 O3 106.53(11) . . ?
O19 S1 C21 104.88(17) . . ?
O20 S1 O3 111.76(9) . . ?
O20 S1 O19 122.92(14) . . ?
O20 S1 C21 108.81(18) . . ?
C10 O1 C7 121.73(14) . . ?
C7 C2 C5 118.24(16) . . ?
C7 C2 C12 116.13(16) . . ?
C12 C2 C5 125.57(16) . . ?
C16 O3 S1 122.87(12) . . ?
C6 C5 C2 117.30(15) . . ?
C15 C5 C2 125.52(17) . . ?
C15 C5 C6 117.13(16) . . ?
C5 C6 C10 121.14(16) . . ?
C5 C6 C14 121.42(16) . . ?
C14 C6 C10 117.44(17) . . ?
O1 C7 C2 122.50(16) . . ?
O1 C7 C9 114.31(15) . . ?
C9 C7 C2 123.16(17) . . ?
C14 O8 H8 109.5 . . ?
C7 C9 H9 121.5 . . ?
C16 C9 C7 117.04(17) . . ?
C16 C9 H9 121.5 . . ?
O1 C10 C6 118.91(17) . . ?
O4 C10 O1 116.06(17) . . ?
O4 C10 C6 125.03(18) . . ?
N17 C11 C15 173.6(2) . . ?
C2 C12 H12 118.9 . . ?
C13 C12 C2 122.23(18) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 H13 120.9 . . ?
C16 C13 C12 118.22(19) . . ?
C16 C13 H13 120.9 . . ?
O8 C14 C6 122.88(18) . . ?
O8 C14 C23 117.51(19) . . ?
C23 C14 C6 119.61(19) . . ?
C5 C15 C11 125.21(17) . . ?
C18 C15 C5 120.04(18) . . ?
C18 C15 C11 114.70(16) . . ?
C9 C16 O3 116.58(17) . . ?
C9 C16 C13 123.14(18) . . ?
C13 C16 O3 119.90(19) . . ?
C15 C18 H18 118.8 . . ?
C23 C18 C15 122.44(18) . . ?
C23 C18 H18 118.8 . . ?
F22 C21 S1 107.5(2) . . ?
F24 C21 S1 110.6(3) . . ?
F24 C21 F22 110.7(3) . . ?
F24 C21 F25 108.9(3) . . ?
F25 C21 S1 109.1(3) . . ?
F25 C21 F22 110.0(3) . . ?
C14 C23 H23 120.3 . . ?
C18 C23 C14 119.33(19) . . ?
C18 C23 H23 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 O3 C16 C9 -120.51(18) . . . . ?
S1 O3 C16 C13 66.4(3) . . . . ?
O1 C7 C9 C16 177.56(17) . . . . ?
C2 C5 C6 C10 3.9(3) . . . . ?
C2 C5 C6 C14 -176.31(18) . . . . ?
C2 C5 C15 C11 -6.6(3) . . . . ?
C2 C5 C15 C18 176.10(19) . . . . ?
C2 C7 C9 C16 -0.7(3) . . . . ?
C2 C12 C13 C16 -1.1(3) . . . . ?
O3 S1 C21 F22 179.4(3) . . . . ?
O3 S1 C21 F24 58.5(3) . . . . ?
O3 S1 C21 F25 -61.3(3) . . . . ?
C5 C2 C7 O1 -2.3(3) . . . . ?
C5 C2 C7 C9 175.84(18) . . . . ?
C5 C2 C12 C13 -174.73(19) . . . . ?
C5 C6 C10 O1 -2.5(3) . . . . ?
C5 C6 C10 O4 177.6(2) . . . . ?
C5 C6 C14 O8 179.8(2) . . . . ?
C5 C6 C14 C23 -0.2(3) . . . . ?
C5 C15 C18 C23 0.2(4) . . . . ?
C6 C5 C15 C11 175.71(18) . . . . ?
C6 C5 C15 C18 -1.6(3) . . . . ?
C6 C14 C23 C18 -1.2(4) . . . . ?
C7 O1 C10 O4 178.53(18) . . . . ?
C7 O1 C10 C6 -1.4(3) . . . . ?
C7 C2 C5 C6 -1.5(3) . . . . ?
C7 C2 C5 C15 -179.20(18) . . . . ?
C7 C2 C12 C13 2.6(3) . . . . ?
C7 C9 C16 O3 -170.46(17) . . . . ?
C7 C9 C16 C13 2.4(3) . . . . ?
O8 C14 C23 C18 178.8(2) . . . . ?
C10 O1 C7 C2 3.9(3) . . . . ?
C10 O1 C7 C9 -174.43(18) . . . . ?
C10 C6 C14 O8 -0.4(3) . . . . ?
C10 C6 C14 C23 179.6(2) . . . . ?
C11 C15 C18 C23 -177.3(2) . . . . ?
C12 C2 C5 C6 175.74(18) . . . . ?
C12 C2 C5 C15 -1.9(3) . . . . ?
C12 C2 C7 O1 -179.82(17) . . . . ?
C12 C2 C7 C9 -1.7(3) . . . . ?
C12 C13 C16 O3 171.08(18) . . . . ?
C12 C13 C16 C9 -1.6(3) . . . . ?
C14 C6 C10 O1 177.66(18) . . . . ?
C14 C6 C10 O4 -2.3(3) . . . . ?
C15 C5 C6 C10 -178.25(17) . . . . ?
C15 C5 C6 C14 1.6(3) . . . . ?
C15 C18 C23 C14 1.2(4) . . . . ?
N17 C11 C15 C5 -165(2) . . . . ?
N17 C11 C15 C18 12(2) . . . . ?
O19 S1 O3 C16 -142.07(18) . . . . ?
O19 S1 C21 F22 69.5(3) . . . . ?
O19 S1 C21 F24 -51.5(3) . . . . ?
O19 S1 C21 F25 -171.3(2) . . . . ?
O20 S1 O3 C16 -5.3(2) . . . . ?
O20 S1 C21 F22 -63.7(3) . . . . ?
O20 S1 C21 F24 175.3(2) . . . . ?
O20 S1 C21 F25 55.5(3) . . . . ?
C21 S1 O3 C16 109.3(2) . . . . ?
