# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_Compound_A
_database_code_depnum_ccdc_archive 'CCDC 1917626'
loop_
_audit_author_name
_audit_author_address
'Christopher Hamaker'
;Illinois State University
United States of America
;
_audit_update_record             
;
2019-05-21 deposited with the CCDC.	2021-02-10 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            'JK77C - Naphthyl-SO2-NH-C6H3(2-Me)(4-COOH)'
_chemical_formula_moiety         'C18 H15 N O4 S'
_chemical_formula_sum            'C18 H15 N O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         341.37

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.6257(9)
_cell_length_b                   14.7988(10)
_cell_length_c                   15.0858(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.281(4)
_cell_angle_gamma                90
_cell_volume                     3202.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.2451
_cell_measurement_theta_max      26.2794
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424

_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            45692
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3264
_reflns_number_gt                2863
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0833
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         3264
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+3.3812P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.394
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S11 0.80269(2) 0.15933(2) 0.39094(2) 0.01481(10) Uani d . . . 1 . .
C C1 0.92182(9) 0.12944(9) 0.42183(9) 0.0168(3) Uani d . . . 1 . .
C C10 0.97963(10) 0.16555(9) 0.50144(9) 0.0178(3) Uani d . . . 1 . .
C C2 0.95463(11) 0.06831(10) 0.36747(10) 0.0227(3) Uani d . . . 1 . .
H H2 0.914291 0.045361 0.315226 0.027 Uiso calc U . R 1 . .
C C7 1.10393(12) 0.23047(14) 0.65445(12) 0.0372(4) Uani d . . . 1 . .
H H7 1.145408 0.252994 0.706162 0.045 Uiso calc U . R 1 . .
C C9 0.94993(10) 0.22824(10) 0.56069(9) 0.0202(3) Uani d . . . 1 . .
H H9 0.887093 0.248525 0.548861 0.024 Uiso calc U . R 1 . .
C C6 1.13461(11) 0.16956(13) 0.59919(12) 0.0340(4) Uani d . . . 1 . .
H H6 1.197489 0.149514 0.613183 0.041 Uiso calc U . R 1 . .
C C5 1.07450(10) 0.13564(11) 0.52134(10) 0.0238(3) Uani d . . . 1 . .
C C3 1.04847(11) 0.03931(11) 0.38900(11) 0.0281(4) Uani d . . . 1 . .
H H3 1.0712 -0.003179 0.351349 0.034 Uiso calc U . R 1 . .
C C8 1.01056(11) 0.26002(12) 0.63479(10) 0.0283(4) Uani d . . . 1 . .
H H8 0.989482 0.302542 0.673499 0.034 Uiso calc U . R 1 . .
C C4 1.10605(11) 0.07233(11) 0.46363(11) 0.0284(4) Uani d . . . 1 . .
H H4 1.169007 0.052487 0.477456 0.034 Uiso calc U . R 1 . .
O O12 0.75960(7) 0.15118(7) 0.46844(6) 0.0187(2) Uani d . . . 1 . .
O O13 0.76411(7) 0.11062(7) 0.31065(7) 0.0227(2) Uani d . . . 1 . .
N N14 0.79864(8) 0.26705(8) 0.36745(8) 0.0146(2) Uani d . . . 1 . .
C C16 0.83750(9) 0.40382(9) 0.29583(9) 0.0148(3) Uani d . . . 1 . .
C C17 0.87377(9) 0.44578(9) 0.22785(9) 0.0160(3) Uani d . . . 1 . .
H H17 0.87718 0.509866 0.226641 0.019 Uiso calc U . R 1 . .
C C18 0.90528(9) 0.39585(9) 0.16139(9) 0.0156(3) Uani d . . . 1 . .
C C15 0.83470(9) 0.30901(9) 0.29699(8) 0.0135(3) Uani d . . . 1 . .
C C19 0.89999(9) 0.30235(10) 0.16245(9) 0.0166(3) Uani d . . . 1 . .
H H19 0.920498 0.26812 0.116761 0.02 Uiso calc U . R 1 . .
C C20 0.86491(9) 0.25856(10) 0.22990(9) 0.0164(3) Uani d . . . 1 . .
H H20 0.861426 0.194469 0.230493 0.02 Uiso calc U . R 1 . .
C C21 0.80142(10) 0.45927(10) 0.36543(10) 0.0207(3) Uani d . . . 1 . .
H H21A 0.807438 0.523654 0.352498 0.031 Uiso calc U . R 1 . .
H H21B 0.837689 0.445506 0.425684 0.031 Uiso calc U . R 1 . .
H H21C 0.735676 0.444702 0.363376 0.031 Uiso calc U . R 1 . .
C C22 0.94566(9) 0.44253(10) 0.09122(9) 0.0177(3) Uani d . . . 1 . .
O O23 0.95683(7) 0.52703(7) 0.09512(7) 0.0250(2) Uani d . . . 1 . .
O O24 0.96781(8) 0.39306(8) 0.02914(7) 0.0271(3) Uani d . . D 1 . .
H H14 0.7898(12) 0.2991(13) 0.4118(13) 0.028(5) Uiso d . . . 1 . .
H H24 0.991(3) 0.422(3) -0.012(2) 0.149(15) Uiso d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S11 O13 . 1.4276(10) ?
S11 O12 . 1.4376(10) ?
S11 N14 . 1.6316(12) ?
S11 C1 . 1.7694(14) ?
C1 C2 . 1.369(2) ?
C1 C10 . 1.430(2) ?
C10 C9 . 1.414(2) ?
C10 C5 . 1.431(2) ?
C2 C3 . 1.414(2) ?
C2 H2 . 0.95 ?
C7 C6 . 1.362(3) ?
C7 C8 . 1.409(2) ?
C7 H7 . 0.95 ?
C9 C8 . 1.367(2) ?
C9 H9 . 0.95 ?
C6 C5 . 1.414(2) ?
C6 H6 . 0.95 ?
C5 C4 . 1.416(2) ?
C3 C4 . 1.358(2) ?
C3 H3 . 0.95 ?
C8 H8 . 0.95 ?
C4 H4 . 0.95 ?
N14 C15 . 1.4188(16) ?
N14 H14 . 0.851(19) ?
C16 C17 . 1.3898(18) ?
C16 C15 . 1.4040(19) ?
C16 C21 . 1.5070(18) ?
C17 C18 . 1.3945(19) ?
C17 H17 . 0.95 ?
C18 C19 . 1.386(2) ?
C18 C22 . 1.4804(18) ?
C15 C20 . 1.3970(19) ?
C19 C20 . 1.3868(18) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 O23 . 1.2610(18) ?
C22 O24 . 1.2793(17) ?
O24 H24 . 0.880(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O13 S11 O12 . . 118.96(6) ?
O13 S11 N14 . . 108.51(6) ?
O12 S11 N14 . . 104.81(6) ?
O13 S11 C1 . . 107.62(7) ?
O12 S11 C1 . . 109.31(6) ?
N14 S11 C1 . . 107.07(6) ?
C2 C1 C10 . . 122.06(13) ?
C2 C1 S11 . . 116.73(11) ?
C10 C1 S11 . . 121.18(10) ?
C9 C10 C1 . . 124.86(13) ?
C9 C10 C5 . . 118.37(13) ?
C1 C10 C5 . . 116.76(13) ?
C1 C2 C3 . . 120.07(15) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C6 C7 C8 . . 119.88(16) ?
C6 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C8 C9 C10 . . 120.81(14) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C7 C6 C5 . . 121.16(15) ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C5 C4 . . 121.39(14) ?
C6 C5 C10 . . 118.95(14) ?
C4 C5 C10 . . 119.65(14) ?
C4 C3 C2 . . 119.86(14) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C9 C8 C7 . . 120.81(15) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C3 C4 C5 . . 121.59(14) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C15 N14 S11 . . 125.97(10) ?
C15 N14 H14 . . 118.8(13) ?
S11 N14 H14 . . 112.2(13) ?
C17 C16 C15 . . 118.16(12) ?
C17 C16 C21 . . 120.47(12) ?
C15 C16 C21 . . 121.36(12) ?
C16 C17 C18 . . 121.42(13) ?
C16 C17 H17 . . 119.3 ?
C18 C17 H17 . . 119.3 ?
C19 C18 C17 . . 119.59(12) ?
C19 C18 C22 . . 120.33(12) ?
C17 C18 C22 . . 120.07(13) ?
C20 C15 C16 . . 120.73(12) ?
C20 C15 N14 . . 121.70(12) ?
C16 C15 N14 . . 117.56(12) ?
C18 C19 C20 . . 120.29(13) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C19 C20 C15 . . 119.78(13) ?
C19 C20 H20 . . 120.1 ?
C15 C20 H20 . . 120.1 ?
C16 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C16 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O23 C22 O24 . . 123.54(13) ?
O23 C22 C18 . . 119.71(12) ?
O24 C22 C18 . . 116.74(13) ?
C22 O24 H24 . . 116.(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O13 S11 C1 C2 . . . . -0.34(13) ?
O12 S11 C1 C2 . . . . 130.16(11) ?
N14 S11 C1 C2 . . . . -116.83(11) ?
O13 S11 C1 C10 . . . . -178.40(11) ?
O12 S11 C1 C10 . . . . -47.89(13) ?
N14 S11 C1 C10 . . . . 65.11(12) ?
C2 C1 C10 C9 . . . . -179.52(13) ?
S11 C1 C10 C9 . . . . -1.57(19) ?
C2 C1 C10 C5 . . . . 0.8(2) ?
S11 C1 C10 C5 . . . . 178.76(10) ?
C10 C1 C2 C3 . . . . -0.4(2) ?
S11 C1 C2 C3 . . . . -178.39(11) ?
C1 C10 C9 C8 . . . . -179.17(14) ?
C5 C10 C9 C8 . . . . 0.5(2) ?
C8 C7 C6 C5 . . . . 0.6(3) ?
C7 C6 C5 C4 . . . . 179.97(17) ?
C7 C6 C5 C10 . . . . -0.7(3) ?
C9 C10 C5 C6 . . . . 0.1(2) ?
C1 C10 C5 C6 . . . . 179.82(14) ?
C9 C10 C5 C4 . . . . 179.50(14) ?
C1 C10 C5 C4 . . . . -0.8(2) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C10 C9 C8 C7 . . . . -0.6(2) ?
C6 C7 C8 C9 . . . . 0.0(3) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
C6 C5 C4 C3 . . . . 179.74(15) ?
C10 C5 C4 C3 . . . . 0.4(2) ?
O13 S11 N14 C15 . . . . -53.37(12) ?
O12 S11 N14 C15 . . . . 178.56(11) ?
C1 S11 N14 C15 . . . . 62.53(12) ?
C15 C16 C17 C18 . . . . 1.06(19) ?
C21 C16 C17 C18 . . . . -178.30(13) ?
C16 C17 C18 C19 . . . . 0.4(2) ?
C16 C17 C18 C22 . . . . -178.51(12) ?
C17 C16 C15 C20 . . . . -1.97(19) ?
C21 C16 C15 C20 . . . . 177.39(12) ?
C17 C16 C15 N14 . . . . 179.19(11) ?
C21 C16 C15 N14 . . . . -1.46(19) ?
S11 N14 C15 C20 . . . . 10.75(18) ?
S11 N14 C15 C16 . . . . -170.42(10) ?
C17 C18 C19 C20 . . . . -1.0(2) ?
C22 C18 C19 C20 . . . . 177.93(12) ?
C18 C19 C20 C15 . . . . 0.1(2) ?
C16 C15 C20 C19 . . . . 1.4(2) ?
N14 C15 C20 C19 . . . . -179.77(12) ?
C19 C18 C22 O23 . . . . -174.43(13) ?
C17 C18 C22 O23 . . . . 4.5(2) ?
C19 C18 C22 O24 . . . . 5.32(19) ?
C17 C18 C22 O24 . . . . -175.80(13) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C20 H20 O13 . 0.95 2.39 3.0255(17) 124.2 ?
N14 H14 O12 7_656 0.851(19) 2.20(2) 3.0240(15) 163.3(17) ?
O24 H24 O23 5_765 0.880(19) 1.755(19) 2.6335(14) 176.(4) ?


####################################################################### 
# 
# 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_Compound_B
_database_code_depnum_ccdc_archive 'CCDC 1917627'
loop_
_audit_author_name
_audit_author_address
'Christopher Hamaker'
;Illinois State University
United States of America
;
_audit_update_record             
;
2019-05-21 deposited with the CCDC.	2021-02-10 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H12 Cl N O2 S'
_chemical_formula_sum            'C16 H12 Cl N O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         317.78

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.923(2)
_cell_length_b                   9.1409(8)
_cell_length_c                   17.8901(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.508(10)
_cell_angle_gamma                90
_cell_volume                     1446.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7.23
_cell_measurement_theta_max      13.14
_cell_measurement_wavelength     0.71073

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.45
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656

_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   3
        Theta correction was applied.
        Averaged transmission function was used.
        No Fourier smoothing was applied.
;
_exptl_absorpt_correction_T_min  0.8136
_exptl_absorpt_correction_T_max  0.8311

_exptl_special_details           
;
;

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.04957
_diffrn_orient_matrix_ub_12      -0.088154
_diffrn_orient_matrix_ub_13      -0.018992
_diffrn_orient_matrix_ub_21      -0.057232
_diffrn_orient_matrix_ub_22      0.015781
_diffrn_orient_matrix_ub_23      -0.05126
_diffrn_orient_matrix_ub_31      0.083937
_diffrn_orient_matrix_ub_32      0.062839
_diffrn_orient_matrix_ub_33      -0.013806
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        -3
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 2 -4
-3 4 1
0 3 -7


_diffrn_reflns_number            3522
_diffrn_reflns_av_R_equivalents  0.0095
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             3317
_reflns_number_gt                2683
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1034
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_number_reflns         3317
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.3885P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.21897(18) 0.04499(19) 0.38612(9) 0.0457(4) Uani d . . . 1 . .
C C2 0.1261(2) -0.0717(2) 0.39446(13) 0.0587(5) Uani d . . . 1 . .
H H2 0.069044 -0.11277 0.35246 0.07 Uiso calc U . R 1 . .
C C3 0.1173(3) -0.1293(2) 0.46686(15) 0.0739(6) Uani d . . . 1 . .
H H3 0.054781 -0.208876 0.472532 0.089 Uiso calc U . R 1 . .
C C4 0.1989(3) -0.0697(3) 0.52760(14) 0.0780(7) Uani d . . . 1 . .
H H4 0.191246 -0.108915 0.574935 0.094 Uiso calc U . R 1 . .
C C5 0.2960(3) 0.0508(2) 0.52186(11) 0.0642(6) Uani d . . . 1 . .
C C6 0.3848(4) 0.1130(4) 0.58601(12) 0.0884(9) Uani d . . . 1 . .
H H6 0.377586 0.074318 0.63348 0.106 Uiso calc U . R 1 . .
C C7 0.4785(3) 0.2259(4) 0.57984(13) 0.0891(9) Uani d . . . 1 . .
H H7 0.535108 0.264493 0.622643 0.107 Uiso calc U . R 1 . .
C C8 0.4907(3) 0.2854(3) 0.50903(13) 0.0762(7) Uani d . . . 1 . .
H H8 0.55598 0.363545 0.505041 0.091 Uiso calc U . R 1 . .
C C9 0.4081(2) 0.2303(2) 0.44536(11) 0.0586(5) Uani d . . . 1 . .
H H9 0.417573 0.271757 0.398731 0.07 Uiso calc U . R 1 . .
C C10 0.3086(2) 0.1114(2) 0.44966(9) 0.0495(4) Uani d . . . 1 . .
C C16 -0.0230(2) 0.4138(2) 0.35849(10) 0.0512(4) Uani d . . . 1 . .
C C17 -0.1683(3) 0.4526(3) 0.37118(13) 0.0697(6) Uani d . . . 1 . .
H H17 -0.182574 0.527298 0.40483 0.084 Uiso calc U . R 1 . .
C C18 -0.2904(2) 0.3802(3) 0.33386(15) 0.0757(7) Uani d . . . 1 . .
H H18 -0.38768 0.406428 0.341871 0.091 Uiso calc U . R 1 . .
C C19 -0.2692(2) 0.2686(3) 0.28452(14) 0.0689(6) Uani d . . . 1 . .
H H19 -0.352196 0.217985 0.260445 0.083 Uiso calc U . R 1 . .
C C20 -0.12493(19) 0.2315(2) 0.27059(11) 0.0527(4) Uani d . . . 1 . .
H H20 -0.111754 0.157203 0.236543 0.063 Uiso calc U . R 1 . .
C C15 0.00030(17) 0.30458(17) 0.30716(8) 0.0407(3) Uani d . . . 1 . .
Cl Cl21 0.13048(7) 0.50473(7) 0.40704(3) 0.0786(2) Uani d . . . 1 . .
N N14 0.14805(15) 0.27456(16) 0.29002(8) 0.0427(3) Uani d . . . 1 . .
O O12 0.37706(13) 0.13394(16) 0.28022(7) 0.0579(3) Uani d . . . 1 . .
O O13 0.13053(14) 0.01777(14) 0.24303(7) 0.0564(3) Uani d . . . 1 . .
S S11 0.22443(4) 0.11132(5) 0.29367(2) 0.04242(12) Uani d . . . 1 . .
H H14 0.210(2) 0.336(2) 0.2973(12) 0.059(6) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.371(3) ?
C1 C10 . 1.436(2) ?
C1 S11 . 1.7682(17) ?
C2 C3 . 1.410(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.342(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.414(4) ?
C4 H4 . 0.93 ?
C5 C10 . 1.423(3) ?
C5 C6 . 1.425(3) ?
C6 C7 . 1.342(4) ?
C6 H6 . 0.93 ?
C7 C8 . 1.396(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.370(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.412(3) ?
C9 H9 . 0.93 ?
C16 C17 . 1.391(3) ?
C16 C15 . 1.391(2) ?
C16 Cl21 . 1.735(2) ?
C17 C18 . 1.371(4) ?
C17 H17 . 0.93 ?
C18 C19 . 1.378(4) ?
C18 H18 . 0.93 ?
C19 C20 . 1.385(3) ?
C19 H19 . 0.93 ?
C20 C15 . 1.390(2) ?
C20 H20 . 0.93 ?
C15 N14 . 1.419(2) ?
N14 S11 . 1.6382(15) ?
N14 H14 . 0.78(2) ?
O12 S11 . 1.4287(13) ?
O13 S11 . 1.4337(12) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 121.64(17) ?
C2 C1 S11 . . 117.37(14) ?
C10 C1 S11 . . 120.99(14) ?
C1 C2 C3 . . 119.9(2) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 122.0(2) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C4 C5 C10 . . 119.4(2) ?
C4 C5 C6 . . 122.3(2) ?
C10 C5 C6 . . 118.3(2) ?
C7 C6 C5 . . 121.8(2) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C6 C7 C8 . . 119.9(2) ?
C6 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C9 C8 C7 . . 120.9(3) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 120.8(2) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C9 C10 C5 . . 118.28(18) ?
C9 C10 C1 . . 124.83(17) ?
C5 C10 C1 . . 116.88(19) ?
C17 C16 C15 . . 120.93(19) ?
C17 C16 Cl21 . . 119.20(17) ?
C15 C16 Cl21 . . 119.86(14) ?
C18 C17 C16 . . 119.7(2) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C17 C18 C19 . . 120.18(19) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C18 C19 C20 . . 120.3(2) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C15 . . 120.4(2) ?
C19 C20 H20 . . 119.8 ?
C15 C20 H20 . . 119.8 ?
C20 C15 C16 . . 118.39(16) ?
C20 C15 N14 . . 121.19(16) ?
C16 C15 N14 . . 120.35(15) ?
C15 N14 S11 . . 124.13(12) ?
C15 N14 H14 . . 118.5(16) ?
S11 N14 H14 . . 111.5(16) ?
O12 S11 O13 . . 118.11(8) ?
O12 S11 N14 . . 105.21(8) ?
O13 S11 N14 . . 108.20(7) ?
O12 S11 C1 . . 110.52(8) ?
O13 S11 C1 . . 107.53(9) ?
N14 S11 C1 . . 106.71(7) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . -0.1(3) ?
S11 C1 C2 C3 . . . . 179.93(15) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
C3 C4 C5 C10 . . . . -0.1(3) ?
C3 C4 C5 C6 . . . . -178.9(2) ?
C4 C5 C6 C7 . . . . 178.9(2) ?
C10 C5 C6 C7 . . . . 0.1(3) ?
C5 C6 C7 C8 . . . . 0.0(4) ?
C6 C7 C8 C9 . . . . 0.1(4) ?
C7 C8 C9 C10 . . . . -0.3(3) ?
C8 C9 C10 C5 . . . . 0.3(3) ?
C8 C9 C10 C1 . . . . -179.13(17) ?
C4 C5 C10 C9 . . . . -179.08(17) ?
C6 C5 C10 C9 . . . . -0.2(3) ?
C4 C5 C10 C1 . . . . 0.4(2) ?
C6 C5 C10 C1 . . . . 179.27(16) ?
C2 C1 C10 C9 . . . . 179.13(17) ?
S11 C1 C10 C9 . . . . -0.9(2) ?
C2 C1 C10 C5 . . . . -0.3(2) ?
S11 C1 C10 C5 . . . . 179.68(12) ?
C15 C16 C17 C18 . . . . 1.4(3) ?
Cl21 C16 C17 C18 . . . . -179.15(16) ?
C16 C17 C18 C19 . . . . 0.6(3) ?
C17 C18 C19 C20 . . . . -1.8(3) ?
C18 C19 C20 C15 . . . . 1.1(3) ?
C19 C20 C15 C16 . . . . 0.8(2) ?
C19 C20 C15 N14 . . . . -175.89(16) ?
C17 C16 C15 C20 . . . . -2.1(3) ?
Cl21 C16 C15 C20 . . . . 178.46(12) ?
C17 C16 C15 N14 . . . . 174.65(16) ?
Cl21 C16 C15 N14 . . . . -4.8(2) ?
C20 C15 N14 S11 . . . . -55.13(19) ?
C16 C15 N14 S11 . . . . 128.19(15) ?
C15 N14 S11 O12 . . . . -173.98(13) ?
C15 N14 S11 O13 . . . . 58.91(15) ?
C15 N14 S11 C1 . . . . -56.54(14) ?
C2 C1 S11 O12 . . . . -133.54(14) ?
C10 C1 S11 O12 . . . . 46.48(15) ?
C2 C1 S11 O13 . . . . -3.31(16) ?
C10 C1 S11 O13 . . . . 176.70(12) ?
C2 C1 S11 N14 . . . . 112.59(14) ?
C10 C1 S11 N14 . . . . -67.40(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N14 H14 O13 2 0.78(2) 2.36(2) 3.0824(19) 153.(2) ?
C19 H19 O12 1_455 0.93 2.6 3.380(2) 141.4 ?


####################################################################### 
# 
# 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_Compound_C
_database_code_depnum_ccdc_archive 'CCDC 1917628'
loop_
_audit_author_name
_audit_author_address
'Christopher Hamaker'
;Illinois State University
United States of America
;
_audit_update_record             
;
2019-05-21 deposited with the CCDC.	2021-02-10 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            
'CGH7-05A  1-naphthyl-SO3-C6H3(2-Me)(4-COOH) CH7-04 from Acetone/Hexanes'
_chemical_formula_moiety         'C18 H14 O5 S'
_chemical_formula_sum            'C18 H14 O5 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         342.35

_chemical_melting_point          ?

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

_cell_length_a                   7.9204(5)
_cell_length_b                   8.7629(6)
_cell_length_c                   11.5108(7)
_cell_angle_alpha                93.616(4)
_cell_angle_beta                 92.555(4)
_cell_angle_gamma                103.286(4)
_cell_volume                     774.55(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4899
_cell_measurement_theta_min      2.3950
_cell_measurement_theta_max      27.8887
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'cut block'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.089
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356

_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            15929
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             3695
_reflns_number_gt                3110
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1028
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         3695
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.4570P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.382
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker Instrument Service v2016.11.0.2'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S11 0.04999(5) 0.82474(5) 0.25079(4) 0.01969(12) Uani d . . . 1 . .
C C1 0.1452(2) 0.77814(18) 0.12171(14) 0.0189(3) Uani d . . . 1 . .
C C10 0.1809(2) 0.62660(18) 0.09554(14) 0.0184(3) Uani d . . . 1 . .
C C5 0.2597(2) 0.60577(19) -0.01160(14) 0.0206(3) Uani d . . . 1 . .
C C6 0.2967(2) 0.4586(2) -0.04357(16) 0.0247(4) Uani d . . . 1 . .
H H6 0.347509 0.44363 -0.11537 0.03 Uiso calc U . R 1 . .
C C7 0.2602(2) 0.3385(2) 0.02769(17) 0.0284(4) Uani d . . . 1 . .
H H7 0.286164 0.240574 0.005464 0.034 Uiso calc U . R 1 . .
C C2 0.1861(2) 0.89730(19) 0.04832(15) 0.0236(4) Uani d . . . 1 . .
H H2 0.160199 0.995958 0.068132 0.028 Uiso calc U . R 1 . .
C C3 0.2662(2) 0.8742(2) -0.05603(16) 0.0278(4) Uani d . . . 1 . .
H H3 0.295228 0.957134 -0.106166 0.033 Uiso calc U . R 1 . .
C C9 0.1448(2) 0.49864(19) 0.16810(15) 0.0233(3) Uani d . . . 1 . .
H H9 0.093383 0.510314 0.240153 0.028 Uiso calc U . R 1 . .
C C4 0.3020(2) 0.7317(2) -0.08479(15) 0.0255(4) Uani d . . . 1 . .
H H4 0.356248 0.716657 -0.1552 0.031 Uiso calc U . R 1 . .
C C8 0.1840(2) 0.3586(2) 0.13417(17) 0.0275(4) Uani d . . . 1 . .
H H8 0.159512 0.273987 0.18317 0.033 Uiso calc U . R 1 . .
O O13 0.00181(15) 0.97098(14) 0.24035(11) 0.0262(3) Uani d . . . 1 . .
O O12 -0.07333(15) 0.69300(14) 0.28636(11) 0.0268(3) Uani d . . . 1 . .
O O14 0.20592(14) 0.84890(13) 0.34873(10) 0.0188(2) Uani d . . . 1 . .
C C15 0.3475(2) 0.98248(18) 0.35527(13) 0.0173(3) Uani d . . . 1 . .
C C18 0.6335(2) 1.22795(18) 0.40186(13) 0.0187(3) Uani d . . . 1 . .
C C20 0.3230(2) 1.12768(19) 0.39655(15) 0.0226(3) Uani d . . . 1 . .
H H20 0.209631 1.141953 0.408974 0.027 Uiso calc U . R 1 . .
C C17 0.6528(2) 1.08196(19) 0.35666(14) 0.0205(3) Uani d . . . 1 . .
H H17 0.7658 1.068153 0.342553 0.025 Uiso calc U . R 1 . .
C C22 0.7938(2) 1.35158(19) 0.43838(14) 0.0207(3) Uani d . . . 1 . .
C C16 0.5097(2) 0.95583(19) 0.33173(14) 0.0193(3) Uani d . . . 1 . .
C C19 0.4683(2) 1.25191(19) 0.41934(15) 0.0224(3) Uani d . . . 1 . .
H H19 0.454788 1.352722 0.446727 0.027 Uiso calc U . R 1 . .
C C21 0.5320(2) 0.7965(2) 0.28763(17) 0.0280(4) Uani d . . . 1 . .
H H21A 0.513134 0.784209 0.202496 0.042 Uiso calc U . R 1 . .
H H21B 0.447368 0.714456 0.322008 0.042 Uiso calc U . R 1 . .
H H21C 0.649906 0.787116 0.309699 0.042 Uiso calc U . R 1 . .
O O23 0.93972(15) 1.33341(14) 0.41597(11) 0.0264(3) Uani d . . . 1 . .
O O24 0.76741(17) 1.47516(14) 0.49785(12) 0.0265(3) Uani d . . . 1 . .
H H24 0.867(4) 1.539(4) 0.520(3) 0.069(9) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S11 O12 . 1.4253(13) ?
S11 O13 . 1.4291(12) ?
S11 O14 . 1.6021(12) ?
S11 C1 . 1.7629(17) ?
C1 C2 . 1.374(2) ?
C1 C10 . 1.437(2) ?
C10 C9 . 1.424(2) ?
C10 C5 . 1.427(2) ?
C5 C6 . 1.417(2) ?
C5 C4 . 1.418(2) ?
C6 C7 . 1.362(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.409(3) ?
C7 H7 . 0.95 ?
C2 C3 . 1.408(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.367(2) ?
C3 H3 . 0.95 ?
C9 C8 . 1.371(2) ?
C9 H9 . 0.95 ?
C4 H4 . 0.95 ?
C8 H8 . 0.95 ?
O14 C15 . 1.4181(18) ?
C15 C20 . 1.389(2) ?
C15 C16 . 1.393(2) ?
C18 C19 . 1.393(2) ?
C18 C17 . 1.394(2) ?
C18 C22 . 1.492(2) ?
C20 C19 . 1.393(2) ?
C20 H20 . 0.95 ?
C17 C16 . 1.394(2) ?
C17 H17 . 0.95 ?
C22 O23 . 1.238(2) ?
C22 O24 . 1.307(2) ?
C16 C21 . 1.507(2) ?
C19 H19 . 0.95 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
O24 H24 . 0.87(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O12 S11 O13 . . 119.71(8) ?
O12 S11 O14 . . 102.92(7) ?
O13 S11 O14 . . 108.97(7) ?
O12 S11 C1 . . 112.00(8) ?
O13 S11 C1 . . 108.38(8) ?
O14 S11 C1 . . 103.48(7) ?
C2 C1 C10 . . 121.96(15) ?
C2 C1 S11 . . 115.65(13) ?
C10 C1 S11 . . 122.38(12) ?
C9 C10 C5 . . 118.56(15) ?
C9 C10 C1 . . 125.09(15) ?
C5 C10 C1 . . 116.35(14) ?
C6 C5 C4 . . 120.37(16) ?
C6 C5 C10 . . 119.36(15) ?
C4 C5 C10 . . 120.27(15) ?
C7 C6 C5 . . 120.61(17) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 120.37(16) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C1 C2 C3 . . 120.46(16) ?
C1 C2 H2 . . 119.8 ?
C3 C2 H2 . . 119.8 ?
C4 C3 C2 . . 119.63(16) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C8 C9 C10 . . 120.13(16) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C3 C4 C5 . . 121.31(16) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C9 C8 C7 . . 120.96(16) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C15 O14 S11 . . 121.47(10) ?
C20 C15 C16 . . 123.33(15) ?
C20 C15 O14 . . 119.42(14) ?
C16 C15 O14 . . 116.84(13) ?
C19 C18 C17 . . 120.10(15) ?
C19 C18 C22 . . 121.67(14) ?
C17 C18 C22 . . 118.08(15) ?
C15 C20 C19 . . 118.48(15) ?
C15 C20 H20 . . 120.8 ?
C19 C20 H20 . . 120.8 ?
C16 C17 C18 . . 121.37(15) ?
C16 C17 H17 . . 119.3 ?
C18 C17 H17 . . 119.3 ?
O23 C22 O24 . . 123.73(15) ?
O23 C22 C18 . . 121.32(15) ?
O24 C22 C18 . . 114.91(14) ?
C15 C16 C17 . . 116.78(14) ?
C15 C16 C21 . . 121.99(15) ?
C17 C16 C21 . . 121.14(15) ?
C20 C19 C18 . . 119.83(15) ?
C20 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C16 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C16 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C22 O24 H24 . . 109.8(19) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O12 S11 C1 C2 . . . . 146.24(13) ?
O13 S11 C1 C2 . . . . 12.00(15) ?
O14 S11 C1 C2 . . . . -103.59(13) ?
O12 S11 C1 C10 . . . . -34.89(15) ?
O13 S11 C1 C10 . . . . -169.12(12) ?
O14 S11 C1 C10 . . . . 75.29(14) ?
C2 C1 C10 C9 . . . . 178.95(16) ?
S11 C1 C10 C9 . . . . 0.1(2) ?
C2 C1 C10 C5 . . . . -0.6(2) ?
S11 C1 C10 C5 . . . . -179.45(11) ?
C9 C10 C5 C6 . . . . 1.1(2) ?
C1 C10 C5 C6 . . . . -179.28(14) ?
C9 C10 C5 C4 . . . . -178.31(15) ?
C1 C10 C5 C4 . . . . 1.3(2) ?
C4 C5 C6 C7 . . . . 178.44(16) ?
C10 C5 C6 C7 . . . . -1.0(2) ?
C5 C6 C7 C8 . . . . 0.3(3) ?
C10 C1 C2 C3 . . . . -0.3(3) ?
S11 C1 C2 C3 . . . . 178.60(13) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
C5 C10 C9 C8 . . . . -0.6(2) ?
C1 C10 C9 C8 . . . . 179.81(15) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
C6 C5 C4 C3 . . . . 179.50(16) ?
C10 C5 C4 C3 . . . . -1.1(3) ?
C10 C9 C8 C7 . . . . 0.0(3) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
O12 S11 O14 C15 . . . . -171.38(11) ?
O13 S11 O14 C15 . . . . -43.31(13) ?
C1 S11 O14 C15 . . . . 71.86(12) ?
S11 O14 C15 C20 . . . . 73.47(17) ?
S11 O14 C15 C16 . . . . -113.61(14) ?
C16 C15 C20 C19 . . . . -2.2(3) ?
O14 C15 C20 C19 . . . . 170.22(15) ?
C19 C18 C17 C16 . . . . -2.2(2) ?
C22 C18 C17 C16 . . . . 173.42(15) ?
C19 C18 C22 O23 . . . . -175.36(16) ?
C17 C18 C22 O23 . . . . 9.1(2) ?
C19 C18 C22 O24 . . . . 6.7(2) ?
C17 C18 C22 O24 . . . . -168.82(15) ?
C20 C15 C16 C17 . . . . 2.9(2) ?
O14 C15 C16 C17 . . . . -169.73(14) ?
C20 C15 C16 C21 . . . . 179.64(16) ?
O14 C15 C16 C21 . . . . 7.0(2) ?
C18 C17 C16 C15 . . . . -0.6(2) ?
C18 C17 C16 C21 . . . . -177.41(16) ?
C15 C20 C19 C18 . . . . -0.8(3) ?
C17 C18 C19 C20 . . . . 2.9(2) ?
C22 C18 C19 C20 . . . . -172.55(15) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O24 H24 O23 2_786 0.87(3) 1.77(3) 2.6411(17) 173.(3) ?



#===END
