# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1585656'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'Triethylammonium 3-[(4-hydroxy-2,2-dioxido-1,2-benzoxathiin-3-yl)methylphenyl]-1,2-benzoxathiin-4-olate 2,2-dioxide'
_chemical_name_common            ?
_chemical_melting_point          468-471
_chemical_formula_moiety         'C23 H15 O8 S2, C6 H16 N'
_chemical_formula_sum            'C29 H31 N O8 S2'
_chemical_formula_weight         585.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   9.7287(3)
_cell_length_b                   16.2803(5)
_cell_length_c                   18.0736(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.594(3)
_cell_angle_gamma                90
_cell_volume                     2837.50(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    15108
_cell_measurement_theta_min      2.7260
_cell_measurement_theta_max      30.8310

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.80677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3991
_diffrn_reflns_number            37305
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         31.197
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8392
_reflns_number_gt                7204
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
;
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+1.6195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8392
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.12138(11) 0.58118(7) 0.46940(6) 0.0280(2) Uani 1 1 d . . . . .
S2A S 0.18593(4) 0.63257(2) 0.54148(2) 0.02449(9) Uani 1 1 d . . . . .
C3A C 0.32790(13) 0.67959(8) 0.51161(7) 0.0173(2) Uani 1 1 d . . . . .
C4A C 0.40179(13) 0.63255(8) 0.46885(7) 0.0170(2) Uani 1 1 d . . . . .
C5A C 0.35177(14) 0.55205(8) 0.43965(7) 0.0187(2) Uani 1 1 d . . . . .
C6A C 0.43748(16) 0.49926(8) 0.40515(7) 0.0226(3) Uani 1 1 d . . . . .
H6A H 0.5327 0.5125 0.4055 0.027 Uiso 1 1 calc R U . . .
C7A C 0.38471(19) 0.42804(9) 0.37058(8) 0.0298(3) Uani 1 1 d . . . . .
H7A H 0.4438 0.3922 0.3479 0.036 Uiso 1 1 calc R U . . .
C8A C 0.2455(2) 0.40902(9) 0.36911(9) 0.0347(4) Uani 1 1 d . . . . .
H8A H 0.2096 0.3605 0.3445 0.042 Uiso 1 1 calc R U . . .
C9A C 0.15791(19) 0.45969(10) 0.40296(9) 0.0330(3) Uani 1 1 d . . . . .
H9A H 0.0625 0.4467 0.4019 0.040 Uiso 1 1 calc R U . . .
C10A C 0.21341(15) 0.52989(8) 0.43848(7) 0.0231(3) Uani 1 1 d . . . . .
O11A O 0.08157(12) 0.69151(8) 0.55137(8) 0.0401(3) Uani 1 1 d . . . . .
O12A O 0.22533(14) 0.57502(8) 0.59981(6) 0.0376(3) Uani 1 1 d . . . . .
O13A O 0.51769(10) 0.65615(6) 0.44445(5) 0.0222(2) Uani 1 1 d . . . . .
H13A H 0.554(3) 0.7048(15) 0.4660(14) 0.057(7) Uiso 1 1 d . . . . .
O1B O 0.56101(10) 0.87134(6) 0.70817(5) 0.0218(2) Uani 1 1 d . . . . .
S2B S 0.44583(3) 0.80487(2) 0.67781(2) 0.01886(8) Uani 1 1 d . . . . .
C3B C 0.47616(13) 0.78912(8) 0.58729(6) 0.0163(2) Uani 1 1 d . . . . .
C4B C 0.61024(13) 0.79193(8) 0.57220(7) 0.0170(2) Uani 1 1 d . . . . .
C5B C 0.72393(13) 0.81603(8) 0.63082(7) 0.0181(2) Uani 1 1 d . . . . .
C6B C 0.86256(14) 0.80385(9) 0.62131(8) 0.0247(3) Uani 1 1 d . . . . .
H6B H 0.8844 0.7778 0.5773 0.030 Uiso 1 1 calc R U . . .
C7B C 0.96890(15) 0.82935(10) 0.67534(9) 0.0314(3) Uani 1 1 d . . . . .
H7B H 1.0628 0.8208 0.6682 0.038 Uiso 1 1 calc R U . . .
C8B C 0.93762(16) 0.86742(10) 0.73981(9) 0.0310(3) Uani 1 1 d . . . . .
H8B H 1.0105 0.8854 0.7764 0.037 Uiso 1 1 calc R U . . .
C9B C 0.80142(15) 0.87936(9) 0.75109(8) 0.0250(3) Uani 1 1 d . . . . .
H9B H 0.7799 0.9050 0.7954 0.030 Uiso 1 1 calc R U . . .
C10B C 0.69703(14) 0.85336(8) 0.69681(7) 0.0192(2) Uani 1 1 d . . . . .
O11B O 0.31712(11) 0.84637(7) 0.68047(6) 0.0288(2) Uani 1 1 d . . . . .
O12B O 0.47239(12) 0.73298(7) 0.72300(5) 0.0283(2) Uani 1 1 d . . . . .
O13B O 0.64318(10) 0.77507(6) 0.50655(5) 0.0226(2) Uani 1 1 d . . . . .
C14 C 0.34871(13) 0.76979(8) 0.53160(7) 0.0166(2) Uani 1 1 d . . . . .
H14 H 0.2680 0.7846 0.5579 0.020 Uiso 1 1 calc R U . . .
C15 C 0.33605(14) 0.82577(8) 0.46280(7) 0.0196(2) Uani 1 1 d . . . . .
C16 C 0.28432(16) 0.79757(9) 0.39191(8) 0.0252(3) Uani 1 1 d . . . . .
H16 H 0.2627 0.7410 0.3846 0.030 Uiso 1 1 calc R U . . .
C17 C 0.26381(19) 0.85122(10) 0.33149(8) 0.0340(4) Uani 1 1 d . . . . .
H17 H 0.2286 0.8310 0.2834 0.041 Uiso 1 1 calc R U . . .
C18 C 0.2943(2) 0.93340(11) 0.34102(10) 0.0391(4) Uani 1 1 d . . . . .
H18 H 0.2815 0.9698 0.2996 0.047 Uiso 1 1 calc R U . . .
C19 C 0.34386(19) 0.96273(10) 0.41172(10) 0.0369(4) Uani 1 1 d . . . . .
H19 H 0.3636 1.0195 0.4189 0.044 Uiso 1 1 calc R U . . .
C20 C 0.36460(16) 0.90917(9) 0.47186(8) 0.0277(3) Uani 1 1 d . . . . .
H20 H 0.3988 0.9298 0.5200 0.033 Uiso 1 1 calc R U . . .
N21 N 0.76781(14) 0.82101(9) 0.38768(7) 0.0311(3) Uani 1 1 d . . . . .
H21 H 0.744(2) 0.8111(13) 0.4349(13) 0.044(6) Uiso 1 1 d . . . . .
C22 C 0.73645(17) 0.74302(11) 0.34471(8) 0.0335(3) Uani 1 1 d . . . . .
H22A H 0.7575 0.7510 0.2931 0.040 Uiso 1 1 calc R U . . .
H22B H 0.6361 0.7311 0.3420 0.040 Uiso 1 1 calc R U . . .
C23 C 0.8170(2) 0.67040(13) 0.37834(11) 0.0445(4) Uani 1 1 d . . . . .
H23A H 0.7811 0.6201 0.3529 0.067 Uiso 1 1 calc R U . . .
H23B H 0.8072 0.6666 0.4315 0.067 Uiso 1 1 calc R U . . .
H23C H 0.9151 0.6770 0.3726 0.067 Uiso 1 1 calc R U . . .
C24 C 0.6695(2) 0.88787(14) 0.35873(11) 0.0487(5) Uani 1 1 d . . . . .
H24A H 0.6835 0.9353 0.3932 0.058 Uiso 1 1 calc R U . . .
H24B H 0.5735 0.8680 0.3591 0.058 Uiso 1 1 calc R U . . .
C25 C 0.6851(4) 0.9170(2) 0.28056(16) 0.0952(12) Uani 1 1 d . . . . .
H25A H 0.6653 0.8715 0.2453 0.143 Uiso 1 1 calc R U . . .
H25B H 0.7801 0.9364 0.2793 0.143 Uiso 1 1 calc R U . . .
H25C H 0.6199 0.9620 0.2666 0.143 Uiso 1 1 calc R U . . .
C26 C 0.9186(2) 0.84287(15) 0.39387(11) 0.0479(5) Uani 1 1 d . . . . .
H26A H 0.9444 0.8506 0.3432 0.057 Uiso 1 1 calc R U . . .
H26B H 0.9743 0.7968 0.4176 0.057 Uiso 1 1 calc R U . . .
C27 C 0.9534(3) 0.92019(17) 0.43898(15) 0.0672(7) Uani 1 1 d . . . . .
H27A H 0.9059 0.9672 0.4130 0.101 Uiso 1 1 calc R U . . .
H27B H 1.0538 0.9293 0.4448 0.101 Uiso 1 1 calc R U . . .
H27C H 0.9230 0.9142 0.4883 0.101 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C10A 1.3941(18) . ?
O1A S2A 1.6048(11) . ?
S2A O12A 1.4246(13) . ?
S2A O11A 1.4252(12) . ?
S2A C3A 1.7269(13) . ?
C3A C4A 1.3591(17) . ?
C3A C14 1.5194(17) . ?
C4A O13A 1.3209(16) . ?
C4A C5A 1.4714(17) . ?
C5A C10A 1.391(2) . ?
C5A C6A 1.4001(18) . ?
C6A C7A 1.383(2) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.387(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.385(2) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.385(2) . ?
C9A H9A 0.9500 . ?
O13A H13A 0.93(3) . ?
O1B C10B 1.3967(16) . ?
O1B S2B 1.6017(10) . ?
S2B O11B 1.4293(11) . ?
S2B O12B 1.4312(11) . ?
S2B C3B 1.7195(12) . ?
C3B C4B 1.3682(18) . ?
C3B C14 1.5230(16) . ?
C4B O13B 1.2986(15) . ?
C4B C5B 1.4799(17) . ?
C5B C10B 1.3937(17) . ?
C5B C6B 1.3961(19) . ?
C6B C7B 1.3889(19) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.389(2) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.381(2) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.3819(17) . ?
C9B H9B 0.9500 . ?
C14 C15 1.5336(17) . ?
C14 H14 1.0000 . ?
C15 C20 1.3912(19) . ?
C15 C16 1.3912(18) . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N21 C24 1.497(3) . ?
N21 C22 1.498(2) . ?
N21 C26 1.499(2) . ?
N21 H21 0.93(2) . ?
C22 C23 1.502(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.517(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.514(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C10A O1A S2A 115.76(9) . . ?
O12A S2A O11A 118.45(8) . . ?
O12A S2A O1A 107.21(7) . . ?
O11A S2A O1A 104.12(7) . . ?
O12A S2A C3A 112.02(7) . . ?
O11A S2A C3A 110.69(7) . . ?
O1A S2A C3A 102.75(6) . . ?
C4A C3A C14 128.02(12) . . ?
C4A C3A S2A 115.66(10) . . ?
C14 C3A S2A 116.17(9) . . ?
O13A C4A C3A 124.39(12) . . ?
O13A C4A C5A 113.31(11) . . ?
C3A C4A C5A 122.08(12) . . ?
C10A C5A C6A 117.78(12) . . ?
C10A C5A C4A 120.66(12) . . ?
C6A C5A C4A 121.22(12) . . ?
C7A C6A C5A 120.56(14) . . ?
C7A C6A H6A 119.7 . . ?
C5A C6A H6A 119.7 . . ?
C6A C7A C8A 119.94(14) . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C9A C8A C7A 121.00(14) . . ?
C9A C8A H8A 119.5 . . ?
C7A C8A H8A 119.5 . . ?
C8A C9A C10A 118.12(15) . . ?
C8A C9A H9A 120.9 . . ?
C10A C9A H9A 120.9 . . ?
C9A C10A C5A 122.56(14) . . ?
C9A C10A O1A 116.64(14) . . ?
C5A C10A O1A 120.66(12) . . ?
C4A O13A H13A 113.5(15) . . ?
C10B O1B S2B 116.20(8) . . ?
O11B S2B O12B 117.40(7) . . ?
O11B S2B O1B 104.21(6) . . ?
O12B S2B O1B 106.96(6) . . ?
O11B S2B C3B 111.34(6) . . ?
O12B S2B C3B 112.35(6) . . ?
O1B S2B C3B 103.09(6) . . ?
C4B C3B C14 126.12(11) . . ?
C4B C3B S2B 118.20(9) . . ?
C14 C3B S2B 115.63(9) . . ?
O13B C4B C3B 122.13(11) . . ?
O13B C4B C5B 117.32(11) . . ?
C3B C4B C5B 120.54(11) . . ?
C10B C5B C6B 117.45(12) . . ?
C10B C5B C4B 121.41(12) . . ?
C6B C5B C4B 121.13(12) . . ?
C7B C6B C5B 120.86(13) . . ?
C7B C6B H6B 119.6 . . ?
C5B C6B H6B 119.6 . . ?
C8B C7B C6B 119.86(14) . . ?
C8B C7B H7B 120.1 . . ?
C6B C7B H7B 120.1 . . ?
C9B C8B C7B 120.52(13) . . ?
C9B C8B H8B 119.7 . . ?
C7B C8B H8B 119.7 . . ?
C8B C9B C10B 118.78(13) . . ?
C8B C9B H9B 120.6 . . ?
C10B C9B H9B 120.6 . . ?
C9B C10B C5B 122.52(13) . . ?
C9B C10B O1B 116.94(12) . . ?
C5B C10B O1B 120.39(11) . . ?
C3A C14 C3B 115.35(10) . . ?
C3A C14 C15 112.81(10) . . ?
C3B C14 C15 112.60(10) . . ?
C3A C14 H14 105.0 . . ?
C3B C14 H14 105.0 . . ?
C15 C14 H14 105.0 . . ?
C20 C15 C16 118.23(12) . . ?
C20 C15 C14 119.41(11) . . ?
C16 C15 C14 122.08(12) . . ?
C15 C16 C17 120.81(13) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.38(14) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.48(15) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 120.09(14) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 121.00(13) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C24 N21 C22 110.98(14) . . ?
C24 N21 C26 115.27(17) . . ?
C22 N21 C26 111.72(13) . . ?
C24 N21 H21 102.8(14) . . ?
C22 N21 H21 105.7(14) . . ?
C26 N21 H21 109.5(14) . . ?
N21 C22 C23 113.44(14) . . ?
N21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
N21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N21 C24 C25 114.5(2) . . ?
N21 C24 H24A 108.6 . . ?
C25 C24 H24A 108.6 . . ?
N21 C24 H24B 108.6 . . ?
C25 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N21 C26 C27 112.63(17) . . ?
N21 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
N21 C26 H26B 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10A O1A S2A O12A -65.99(11) . . . . ?
C10A O1A S2A O11A 167.70(10) . . . . ?
C10A O1A S2A C3A 52.20(11) . . . . ?
O12A S2A C3A C4A 74.52(12) . . . . ?
O11A S2A C3A C4A -150.89(11) . . . . ?
O1A S2A C3A C4A -40.23(11) . . . . ?
O12A S2A C3A C14 -109.66(10) . . . . ?
O11A S2A C3A C14 24.92(12) . . . . ?
O1A S2A C3A C14 135.58(9) . . . . ?
C14 C3A C4A O13A 8.8(2) . . . . ?
S2A C3A C4A O13A -175.98(10) . . . . ?
C14 C3A C4A C5A -165.54(11) . . . . ?
S2A C3A C4A C5A 9.69(16) . . . . ?
O13A C4A C5A C10A -158.60(12) . . . . ?
C3A C4A C5A C10A 16.31(18) . . . . ?
O13A C4A C5A C6A 14.56(16) . . . . ?
C3A C4A C5A C6A -170.53(12) . . . . ?
C10A C5A C6A C7A 0.65(18) . . . . ?
C4A C5A C6A C7A -172.71(12) . . . . ?
C5A C6A C7A C8A 0.8(2) . . . . ?
C6A C7A C8A C9A -1.1(2) . . . . ?
C7A C8A C9A C10A -0.1(2) . . . . ?
C8A C9A C10A C5A 1.7(2) . . . . ?
C8A C9A C10A O1A 177.54(14) . . . . ?
C6A C5A C10A C9A -1.9(2) . . . . ?
C4A C5A C10A C9A 171.48(13) . . . . ?
C6A C5A C10A O1A -177.64(12) . . . . ?
C4A C5A C10A O1A -4.25(19) . . . . ?
S2A O1A C10A C9A 150.18(11) . . . . ?
S2A O1A C10A C5A -33.86(16) . . . . ?
C10B O1B S2B O11B -166.85(9) . . . . ?
C10B O1B S2B O12B 68.15(10) . . . . ?
C10B O1B S2B C3B -50.47(10) . . . . ?
O11B S2B C3B C4B 146.13(11) . . . . ?
O12B S2B C3B C4B -79.86(12) . . . . ?
O1B S2B C3B C4B 34.94(12) . . . . ?
O11B S2B C3B C14 -36.19(12) . . . . ?
O12B S2B C3B C14 97.83(10) . . . . ?
O1B S2B C3B C14 -147.38(9) . . . . ?
C14 C3B C4B O13B -2.3(2) . . . . ?
S2B C3B C4B O13B 175.08(10) . . . . ?
C14 C3B C4B C5B 176.63(12) . . . . ?
S2B C3B C4B C5B -5.96(17) . . . . ?
O13B C4B C5B C10B 164.79(12) . . . . ?
C3B C4B C5B C10B -14.22(19) . . . . ?
O13B C4B C5B C6B -13.75(19) . . . . ?
C3B C4B C5B C6B 167.24(13) . . . . ?
C10B C5B C6B C7B -1.0(2) . . . . ?
C4B C5B C6B C7B 177.61(14) . . . . ?
C5B C6B C7B C8B 0.0(2) . . . . ?
C6B C7B C8B C9B 0.7(3) . . . . ?
C7B C8B C9B C10B -0.5(2) . . . . ?
C8B C9B C10B C5B -0.4(2) . . . . ?
C8B C9B C10B O1B -175.97(13) . . . . ?
C6B C5B C10B C9B 1.2(2) . . . . ?
C4B C5B C10B C9B -177.39(13) . . . . ?
C6B C5B C10B O1B 176.57(12) . . . . ?
C4B C5B C10B O1B -2.02(19) . . . . ?
S2B O1B C10B C9B -146.29(11) . . . . ?
S2B O1B C10B C5B 38.09(15) . . . . ?
C4A C3A C14 C3B -72.24(17) . . . . ?
S2A C3A C14 C3B 112.55(11) . . . . ?
C4A C3A C14 C15 59.09(17) . . . . ?
S2A C3A C14 C15 -116.12(11) . . . . ?
C4B C3B C14 C3A 76.79(16) . . . . ?
S2B C3B C14 C3A -100.68(11) . . . . ?
C4B C3B C14 C15 -54.65(17) . . . . ?
S2B C3B C14 C15 127.88(10) . . . . ?
C3A C14 C15 C20 -174.38(13) . . . . ?
C3B C14 C15 C20 -41.68(17) . . . . ?
C3A C14 C15 C16 11.78(18) . . . . ?
C3B C14 C15 C16 144.47(13) . . . . ?
C20 C15 C16 C17 1.0(2) . . . . ?
C14 C15 C16 C17 174.92(14) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C16 C15 C20 C19 -0.8(2) . . . . ?
C14 C15 C20 C19 -174.92(15) . . . . ?
C24 N21 C22 C23 -171.17(15) . . . . ?
C26 N21 C22 C23 58.66(19) . . . . ?
C22 N21 C24 C25 -67.3(3) . . . . ?
C26 N21 C24 C25 61.0(3) . . . . ?
C24 N21 C26 C27 53.7(2) . . . . ?
C22 N21 C26 C27 -178.36(19) . . . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1585657'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'2-Amino-4-(2-methoxyphenyl)-4H-pyrano[3,2-c][1,2]benzoxathiine-3-carbonitrile 5,5-dioxide'
_chemical_name_common            ?
_chemical_melting_point          503-506
_chemical_formula_moiety         'C19 H14 N2 O5 S'
_chemical_formula_sum            'C19 H14 N2 O5 S'
_chemical_formula_weight         382.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.4151(3)
_cell_length_b                   11.8166(5)
_cell_length_c                   17.6708(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.635(5)
_cell_angle_gamma                90
_cell_volume                     1707.63(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    13282
_cell_measurement_theta_min      2.9580
_cell_measurement_theta_max      30.9160

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.65032
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3991
_diffrn_reflns_number            24036
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         31.233
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5049
_reflns_number_gt                4491
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
;
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.8311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5049
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32253(11) 0.64704(7) 0.37333(6) 0.02044(19) Uani 1 1 d . . . . .
C2 C 0.28209(15) 0.75958(10) 0.37287(7) 0.0182(2) Uani 1 1 d . . . . .
C3 C 0.39448(15) 0.84185(10) 0.39706(7) 0.0181(2) Uani 1 1 d . . . . .
C4 C 0.57648(15) 0.82050(10) 0.42614(7) 0.0168(2) Uani 1 1 d . . . . .
H4 H 0.6087 0.8441 0.4820 0.020 Uiso 1 1 calc R U . . .
C5 C 0.60174(15) 0.69464(10) 0.42288(7) 0.0166(2) Uani 1 1 d . . . . .
S6 S 0.80100(4) 0.64383(3) 0.44850(2) 0.01764(9) Uani 1 1 d . . . . .
O7 O 0.77615(11) 0.52435(8) 0.48629(5) 0.02178(19) Uani 1 1 d . . . . .
C8 C 0.65957(15) 0.45205(11) 0.44058(7) 0.0189(2) Uani 1 1 d . . . . .
C9 C 0.69407(17) 0.33756(11) 0.44367(8) 0.0230(3) Uani 1 1 d . . . . .
H9 H 0.7949 0.3097 0.4741 0.028 Uiso 1 1 calc R U . . .
C10 C 0.57777(18) 0.26448(11) 0.40119(9) 0.0262(3) Uani 1 1 d . . . . .
H10 H 0.5986 0.1854 0.4028 0.031 Uiso 1 1 calc R U . . .
C11 C 0.43104(18) 0.30578(11) 0.35628(9) 0.0267(3) Uani 1 1 d . . . . .
H11 H 0.3530 0.2549 0.3268 0.032 Uiso 1 1 calc R U . . .
C12 C 0.39791(17) 0.42088(11) 0.35428(8) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.2972 0.4485 0.3236 0.028 Uiso 1 1 calc R U . . .
C13 C 0.51226(15) 0.49625(10) 0.39729(7) 0.0185(2) Uani 1 1 d . . . . .
C14 C 0.48399(15) 0.61798(10) 0.39874(7) 0.0172(2) Uani 1 1 d . . . . .
N15 N 0.12059(14) 0.77252(10) 0.34397(8) 0.0254(2) Uani 1 1 d . . . . .
H15A H 0.056(3) 0.7128(18) 0.3443(12) 0.038(5) Uiso 1 1 d . . . . .
H15B H 0.074(3) 0.838(2) 0.3416(13) 0.050(6) Uiso 1 1 d . . . . .
C16 C 0.33945(16) 0.95572(11) 0.38979(8) 0.0213(2) Uani 1 1 d . . . . .
N17 N 0.29427(16) 1.04784(10) 0.38301(9) 0.0314(3) Uani 1 1 d . . . . .
C18 C 0.67937(15) 0.88794(10) 0.38200(7) 0.0166(2) Uani 1 1 d . . . . .
C19 C 0.65929(15) 0.87684(10) 0.30112(7) 0.0174(2) Uani 1 1 d . . . . .
C20 C 0.75478(16) 0.94081(11) 0.26265(7) 0.0215(2) Uani 1 1 d . . . . .
H20 H 0.7419 0.9328 0.2080 0.026 Uiso 1 1 calc R U . . .
C21 C 0.86886(17) 1.01639(11) 0.30421(8) 0.0232(3) Uani 1 1 d . . . . .
H21 H 0.9332 1.0603 0.2776 0.028 Uiso 1 1 calc R U . . .
C22 C 0.89012(16) 1.02857(11) 0.38376(8) 0.0222(2) Uani 1 1 d . . . . .
H22 H 0.9687 1.0802 0.4120 0.027 Uiso 1 1 calc R U . . .
C23 C 0.79468(16) 0.96395(10) 0.42190(7) 0.0195(2) Uani 1 1 d . . . . .
H23 H 0.8089 0.9721 0.4766 0.023 Uiso 1 1 calc R U . . .
O24 O 0.54287(12) 0.80191(8) 0.26472(5) 0.0218(2) Uani 1 1 d . . . . .
C25 C 0.51196(17) 0.79687(11) 0.18189(7) 0.0229(3) Uani 1 1 d . . . . .
H25A H 0.4803 0.8720 0.1600 0.034 Uiso 1 1 calc R U . . .
H25B H 0.4232 0.7431 0.1621 0.034 Uiso 1 1 calc R U . . .
H25C H 0.6111 0.7720 0.1667 0.034 Uiso 1 1 calc R U . . .
O26 O 0.86119(12) 0.62332(8) 0.38078(6) 0.0230(2) Uani 1 1 d . . . . .
O27 O 0.89636(12) 0.70952(8) 0.51002(6) 0.0252(2) 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 C14 1.3704(15) . ?
O1 C2 1.3722(15) . ?
C2 N15 1.3431(17) . ?
C2 C3 1.3534(17) . ?
C3 C16 1.4190(17) . ?
C3 C4 1.5173(17) . ?
C4 C5 1.5053(16) . ?
C4 C18 1.5203(16) . ?
C4 H4 1.0000 . ?
C5 C14 1.3361(17) . ?
C5 S6 1.7376(13) . ?
S6 O27 1.4202(10) . ?
S6 O26 1.4259(10) . ?
S6 O7 1.5964(10) . ?
O7 C8 1.4040(15) . ?
C8 C9 1.3821(17) . ?
C8 C13 1.3955(17) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3872(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3971(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.4592(16) . ?
N15 H15A 0.89(2) . ?
N15 H15B 0.86(2) . ?
C16 N17 1.1499(18) . ?
C18 C23 1.3867(17) . ?
C18 C19 1.4052(16) . ?
C19 O24 1.3639(15) . ?
C19 C20 1.3917(17) . ?
C20 C21 1.3879(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.3820(19) . ?
C21 H21 0.9500 . ?
C22 C23 1.3919(17) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
O24 C25 1.4263(15) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C14 O1 C2 118.04(10) . . ?
N15 C2 C3 127.40(12) . . ?
N15 C2 O1 109.87(11) . . ?
C3 C2 O1 122.71(11) . . ?
C2 C3 C16 117.63(12) . . ?
C2 C3 C4 124.19(11) . . ?
C16 C3 C4 118.04(11) . . ?
C5 C4 C3 106.96(10) . . ?
C5 C4 C18 113.30(10) . . ?
C3 C4 C18 112.99(10) . . ?
C5 C4 H4 107.8 . . ?
C3 C4 H4 107.8 . . ?
C18 C4 H4 107.8 . . ?
C14 C5 C4 125.54(11) . . ?
C14 C5 S6 116.51(9) . . ?
C4 C5 S6 117.89(9) . . ?
O27 S6 O26 119.14(6) . . ?
O27 S6 O7 105.62(6) . . ?
O26 S6 O7 107.95(5) . . ?
O27 S6 C5 110.30(6) . . ?
O26 S6 C5 110.61(6) . . ?
O7 S6 C5 101.60(5) . . ?
C8 O7 S6 116.12(8) . . ?
C9 C8 C13 122.63(12) . . ?
C9 C8 O7 117.46(12) . . ?
C13 C8 O7 119.84(11) . . ?
C8 C9 C10 118.27(13) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C9 C10 C11 120.63(12) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.34(13) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.18(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 117.94(12) . . ?
C8 C13 C14 119.12(11) . . ?
C12 C13 C14 122.94(12) . . ?
C5 C14 O1 122.55(11) . . ?
C5 C14 C13 124.21(11) . . ?
O1 C14 C13 113.23(10) . . ?
C2 N15 H15A 118.3(13) . . ?
C2 N15 H15B 121.9(16) . . ?
H15A N15 H15B 116(2) . . ?
N17 C16 C3 179.24(16) . . ?
C23 C18 C19 118.65(11) . . ?
C23 C18 C4 119.58(10) . . ?
C19 C18 C4 121.76(11) . . ?
O24 C19 C20 123.74(11) . . ?
O24 C19 C18 116.17(10) . . ?
C20 C19 C18 120.09(11) . . ?
C21 C20 C19 119.87(12) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 120.85(12) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 118.96(12) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C18 C23 C22 121.58(12) . . ?
C18 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C19 O24 C25 116.61(10) . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O1 C2 N15 177.96(11) . . . . ?
C14 O1 C2 C3 -0.65(17) . . . . ?
N15 C2 C3 C16 -1.8(2) . . . . ?
O1 C2 C3 C16 176.51(11) . . . . ?
N15 C2 C3 C4 -177.46(12) . . . . ?
O1 C2 C3 C4 0.89(19) . . . . ?
C2 C3 C4 C5 -0.51(16) . . . . ?
C16 C3 C4 C5 -176.11(10) . . . . ?
C2 C3 C4 C18 124.85(13) . . . . ?
C16 C3 C4 C18 -50.75(15) . . . . ?
C3 C4 C5 C14 -0.04(16) . . . . ?
C18 C4 C5 C14 -125.20(13) . . . . ?
C3 C4 C5 S6 177.01(8) . . . . ?
C18 C4 C5 S6 51.84(13) . . . . ?
C14 C5 S6 O27 -146.87(10) . . . . ?
C4 C5 S6 O27 35.82(11) . . . . ?
C14 C5 S6 O26 79.20(10) . . . . ?
C4 C5 S6 O26 -98.11(9) . . . . ?
C14 C5 S6 O7 -35.21(10) . . . . ?
C4 C5 S6 O7 147.48(9) . . . . ?
O27 S6 O7 C8 168.22(9) . . . . ?
O26 S6 O7 C8 -63.31(10) . . . . ?
C5 S6 O7 C8 53.06(9) . . . . ?
S6 O7 C8 C9 142.52(10) . . . . ?
S6 O7 C8 C13 -40.50(14) . . . . ?
C13 C8 C9 C10 0.76(19) . . . . ?
O7 C8 C9 C10 177.65(11) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C9 C8 C13 C12 -1.48(18) . . . . ?
O7 C8 C13 C12 -178.30(11) . . . . ?
C9 C8 C13 C14 178.48(11) . . . . ?
O7 C8 C13 C14 1.66(17) . . . . ?
C11 C12 C13 C8 0.97(19) . . . . ?
C11 C12 C13 C14 -178.99(12) . . . . ?
C4 C5 C14 O1 0.23(19) . . . . ?
S6 C5 C14 O1 -176.85(9) . . . . ?
C4 C5 C14 C13 -179.12(11) . . . . ?
S6 C5 C14 C13 3.80(16) . . . . ?
C2 O1 C14 C5 0.10(17) . . . . ?
C2 O1 C14 C13 179.52(10) . . . . ?
C8 C13 C14 C5 16.95(18) . . . . ?
C12 C13 C14 C5 -163.09(12) . . . . ?
C8 C13 C14 O1 -162.46(11) . . . . ?
C12 C13 C14 O1 17.50(17) . . . . ?
C5 C4 C18 C23 -118.08(12) . . . . ?
C3 C4 C18 C23 120.07(12) . . . . ?
C5 C4 C18 C19 62.95(15) . . . . ?
C3 C4 C18 C19 -58.91(15) . . . . ?
C23 C18 C19 O24 -179.23(11) . . . . ?
C4 C18 C19 O24 -0.25(17) . . . . ?
C23 C18 C19 C20 0.42(18) . . . . ?
C4 C18 C19 C20 179.41(12) . . . . ?
O24 C19 C20 C21 179.03(12) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C19 C18 C23 C22 -0.15(19) . . . . ?
C4 C18 C23 C22 -179.16(12) . . . . ?
C21 C22 C23 C18 0.0(2) . . . . ?
C20 C19 O24 C25 -4.71(18) . . . . ?
C18 C19 O24 C25 174.93(11) . . . . ?

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.086

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
