# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_hb12_a
_database_code_depnum_ccdc_archive 'CCDC 1414605'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 O2 S'
_chemical_formula_weight         320.39

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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.4670(13)
_cell_length_b                   13.272(2)
_cell_length_c                   16.898(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1674.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8749
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.03

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.7295
_exptl_transmission_factor_max   0.7460
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2012/1)'
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83941
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         30.036
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4886
_reflns_number_gt                4491
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0505P)²+0.1496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1854 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.004(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4886
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
S1 S 0.62789(5) 0.54671(3) 0.40548(2) 0.04098(11) Uani 1 1 d . . . . .
C2 C 0.5657(3) 0.44060(13) 0.45737(11) 0.0481(4) Uani 1 1 d . . . . .
C3 C 0.3965(3) 0.41000(14) 0.43777(14) 0.0588(5) Uani 1 1 d . . . . .
H3 H 0.3406 0.3542 0.4600 0.071 Uiso 1 1 calc R U . . .
C4 C 0.3161(2) 0.47208(14) 0.38034(14) 0.0539(5) Uani 1 1 d . . . . .
C5 C 0.1327(3) 0.46034(19) 0.34499(19) 0.0780(7) Uani 1 1 d . . . . .
H5A H 0.0473 0.5013 0.3740 0.094 Uiso 1 1 calc R U . . .
H5B H 0.0949 0.3905 0.3483 0.094 Uiso 1 1 calc R U . . .
C6 C 0.1388(3) 0.4934(2) 0.25905(19) 0.0804(8) Uani 1 1 d . . . . .
H6A H 0.2072 0.4447 0.2288 0.096 Uiso 1 1 calc R U . . .
H6B H 0.0179 0.4944 0.2380 0.096 Uiso 1 1 calc R U . . .
C7 C 0.2216(3) 0.59616(18) 0.24897(12) 0.0559(5) Uani 1 1 d . . . . .
C8 C 0.1602(3) 0.6620(2) 0.19137(12) 0.0697(7) Uani 1 1 d . . . . .
H8 H 0.0652 0.6427 0.1592 0.084 Uiso 1 1 calc R U . . .
C9 C 0.2364(3) 0.7548(2) 0.18087(13) 0.0728(7) Uani 1 1 d . . . . .
H9 H 0.1929 0.7980 0.1420 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3785(3) 0.78433(19) 0.22819(11) 0.0599(5) Uani 1 1 d . . . . .
H10 H 0.4293 0.8477 0.2211 0.072 Uiso 1 1 calc R U . . .
C11 C 0.4463(2) 0.72018(14) 0.28635(10) 0.0430(3) Uani 1 1 d . . . . .
C12 C 0.3681(2) 0.62472(12) 0.29717(9) 0.0418(3) Uani 1 1 d . . . . .
C13 C 0.4244(2) 0.55055(13) 0.35687(10) 0.0405(3) Uani 1 1 d . . . . .
C14 C 0.6001(2) 0.75558(12) 0.33502(10) 0.0422(3) Uani 1 1 d . . . . .
C15 C 0.5716(4) 0.80765(17) 0.40513(13) 0.0647(5) Uani 1 1 d . . . . .
H15 H 0.4556 0.8206 0.4224 0.078 Uiso 1 1 calc R U . . .
C16 C 0.7171(5) 0.8402(2) 0.44936(15) 0.0832(8) Uani 1 1 d . . . . .
H16 H 0.6981 0.8755 0.4962 0.100 Uiso 1 1 calc R U . . .
C17 C 0.8886(4) 0.82094(19) 0.42469(15) 0.0744(7) Uani 1 1 d . . . . .
H17 H 0.9850 0.8427 0.4551 0.089 Uiso 1 1 calc R U . . .
C18 C 0.9185(3) 0.77014(17) 0.35596(14) 0.0627(5) Uani 1 1 d . . . . .
H18 H 1.0350 0.7573 0.3394 0.075 Uiso 1 1 calc R U . . .
C19 C 0.7747(3) 0.73755(15) 0.31074(12) 0.0498(4) Uani 1 1 d . . . . .
H19 H 0.7956 0.7032 0.2636 0.060 Uiso 1 1 calc R U . . .
C20 C 0.6865(3) 0.39151(16) 0.51358(12) 0.0563(5) Uani 1 1 d . . . . .
O21 O 0.6534(3) 0.31424(13) 0.54754(12) 0.0798(5) Uani 1 1 d . . . . .
O22 O 0.8383(2) 0.44303(14) 0.52307(11) 0.0753(5) Uani 1 1 d . . . . .
C23 C 0.9713(5) 0.3999(3) 0.57611(19) 0.1008(11) Uani 1 1 d . . . . .
H23A H 0.9186 0.3889 0.6272 0.151 Uiso 1 1 calc R U . . .
H23B H 1.0706 0.4454 0.5811 0.151 Uiso 1 1 calc R U . . .
H23C H 1.0125 0.3368 0.5550 0.151 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
S1 C2 1.7228(18) . ?
S1 C13 1.7278(17) . ?
C2 C3 1.368(3) . ?
C2 C20 1.463(3) . ?
C3 C4 1.407(3) . ?
C3 H3 0.9300 . ?
C4 C13 1.377(3) . ?
C4 C5 1.503(3) . ?
C5 C6 1.518(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.507(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.386(3) . ?
C7 C12 1.415(2) . ?
C8 C9 1.368(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.407(3) . ?
C11 C14 1.489(2) . ?
C12 C13 1.471(2) . ?
C14 C19 1.388(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.388(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O21 1.201(3) . ?
C20 O22 1.334(3) . ?
O22 C23 1.455(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C2 S1 C13 91.67(9) . . ?
C3 C2 C20 126.46(18) . . ?
C3 C2 S1 111.62(15) . . ?
C20 C2 S1 121.91(16) . . ?
C2 C3 C4 112.78(17) . . ?
C2 C3 H3 123.6 . . ?
C4 C3 H3 123.6 . . ?
C13 C4 C3 113.00(18) . . ?
C13 C4 C5 120.0(2) . . ?
C3 C4 C5 127.04(19) . . ?
C4 C5 C6 108.8(2) . . ?
C4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C7 C6 C5 112.5(2) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C12 119.4(2) . . ?
C8 C7 C6 120.9(2) . . ?
C12 C7 C6 119.6(2) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 119.35(18) . . ?
C10 C11 C14 118.47(18) . . ?
C12 C11 C14 122.19(15) . . ?
C11 C12 C7 119.16(17) . . ?
C11 C12 C13 124.95(15) . . ?
C7 C12 C13 115.88(17) . . ?
C4 C13 C12 122.39(16) . . ?
C4 C13 S1 110.93(14) . . ?
C12 C13 S1 126.68(13) . . ?
C19 C14 C15 118.85(19) . . ?
C19 C14 C11 120.46(16) . . ?
C15 C14 C11 120.68(18) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
O21 C20 O22 123.7(2) . . ?
O21 C20 C2 124.3(2) . . ?
O22 C20 C2 111.94(17) . . ?
C20 O22 C23 116.9(2) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_hg28_a
_database_code_depnum_ccdc_archive 'CCDC 1414606'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 O4 S'
_chemical_formula_weight         378.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8536(2)
_cell_length_b                   23.1341(5)
_cell_length_c                   8.1728(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.5990(11)
_cell_angle_gamma                90
_cell_volume                     1862.30(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.09

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.7125
_exptl_transmission_factor_max   0.7460
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2012/1)'
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41217
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5448
_reflns_number_gt                3819
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0500P)²+0.4066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5448
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_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
S1 S 0.06044(4) 0.13695(2) 0.79775(5) 0.04618(12) Uani 1 1 d . . . . .
C1 C 0.32506(16) 0.12676(6) 0.66958(17) 0.0416(3) Uani 1 1 d . . . . .
C2 C 0.36496(15) 0.07776(6) 0.76015(17) 0.0412(3) Uani 1 1 d . . . . .
C3 C 0.48333(18) 0.04904(8) 0.7214(2) 0.0564(4) Uani 1 1 d . . . . .
H3 H 0.5097 0.0166 0.7813 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5626(2) 0.06776(10) 0.5957(2) 0.0693(5) Uani 1 1 d . . . . .
H4 H 0.6408 0.0476 0.5699 0.083 Uiso 1 1 calc R U . . .
C5 C 0.5258(2) 0.11634(9) 0.5087(2) 0.0657(5) Uani 1 1 d . . . . .
H5 H 0.5808 0.1293 0.4257 0.079 Uiso 1 1 calc R U . . .
C6 C 0.40823(18) 0.14632(7) 0.54252(18) 0.0505(4) Uani 1 1 d . . . . .
C7 C 0.3639(2) 0.19715(8) 0.4386(2) 0.0628(5) Uani 1 1 d . . . . .
H7A H 0.4431 0.2145 0.3905 0.075 Uiso 1 1 calc R U . . .
H7B H 0.3046 0.1836 0.3499 0.075 Uiso 1 1 calc R U . . .
C8 C 0.2904(2) 0.24244(7) 0.5349(2) 0.0642(5) Uani 1 1 d . . . . .
H8A H 0.3539 0.2617 0.6097 0.077 Uiso 1 1 calc R U . . .
H8B H 0.2518 0.2712 0.4610 0.077 Uiso 1 1 calc R U . . .
C9 C 0.17954(19) 0.21452(7) 0.62955(18) 0.0515(4) Uani 1 1 d . . . . .
C10 C 0.19989(16) 0.15964(6) 0.69315(17) 0.0423(3) Uani 1 1 d . . . . .
C11 C -0.02522(19) 0.20041(7) 0.7562(2) 0.0529(4) Uani 1 1 d . . . . .
C12 C 0.0516(2) 0.23715(7) 0.6664(2) 0.0594(5) Uani 1 1 d . . . . .
H12 H 0.0221 0.2736 0.6329 0.071 Uiso 1 1 calc R U . . .
C13 C -0.1633(2) 0.21029(8) 0.8135(2) 0.0635(5) Uani 1 1 d . . . . .
O14 O -0.22740(18) 0.25384(7) 0.7896(2) 0.0961(5) Uani 1 1 d . . . . .
O15 O -0.20778(14) 0.16532(6) 0.89783(19) 0.0728(4) Uani 1 1 d . . . . .
C16 C -0.3423(2) 0.16950(11) 0.9616(3) 0.0886(7) Uani 1 1 d . . . . .
H16A H -0.3460 0.2015 1.0361 0.133 Uiso 1 1 calc R U . . .
H16B H -0.3636 0.1344 1.0182 0.133 Uiso 1 1 calc R U . . .
H16C H -0.4068 0.1753 0.8730 0.133 Uiso 1 1 calc R U . . .
C17 C 0.28971(14) 0.05516(6) 0.90340(16) 0.0372(3) Uani 1 1 d . . . . .
C18 C 0.30903(17) 0.08112(7) 1.05602(18) 0.0472(4) Uani 1 1 d . . . . .
H18 H 0.3621 0.1143 1.0651 0.057 Uiso 1 1 calc R U . . .
C19 C 0.25089(18) 0.05861(8) 1.19442(18) 0.0522(4) Uani 1 1 d . . . . .
H19 H 0.2630 0.0773 1.2945 0.063 Uiso 1 1 calc R U . . .
C20 C 0.17541(17) 0.00875(7) 1.18444(18) 0.0504(4) Uani 1 1 d . . . . .
H20 H 0.1375 -0.0067 1.2778 0.061 Uiso 1 1 calc R U . . .
C21 C 0.15621(16) -0.01831(7) 1.03541(18) 0.0457(3) Uani 1 1 d . . . . .
H21 H 0.1062 -0.0524 1.0290 0.055 Uiso 1 1 calc R U . . .
C22 C 0.21081(14) 0.00477(6) 0.89439(16) 0.0375(3) Uani 1 1 d . . . . .
C23 C 0.17409(15) -0.02192(7) 0.73247(18) 0.0422(3) Uani 1 1 d . . . . .
O24 O 0.16731(13) 0.00374(5) 0.60529(13) 0.0581(3) Uani 1 1 d . . . . .
O25 O 0.14515(15) -0.07790(5) 0.74714(14) 0.0649(3) Uani 1 1 d . . . . .
C26 C 0.0900(2) -0.10624(9) 0.6017(2) 0.0750(6) Uani 1 1 d . . . . .
H26A H 0.0099 -0.0862 0.5635 0.113 Uiso 1 1 calc R U . . .
H26B H 0.0672 -0.1455 0.6273 0.113 Uiso 1 1 calc R U . . .
H26C H 0.1563 -0.1058 0.5178 0.113 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
S1 C10 1.7205(16) . ?
S1 C11 1.7225(16) . ?
C1 C2 1.404(2) . ?
C1 C6 1.415(2) . ?
C1 C10 1.466(2) . ?
C2 C3 1.387(2) . ?
C2 C17 1.4975(19) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(2) . ?
C7 C8 1.508(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.502(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.384(2) . ?
C9 C12 1.405(3) . ?
C11 C12 1.366(3) . ?
C11 C13 1.469(3) . ?
C12 H12 0.9300 . ?
C13 O14 1.202(2) . ?
C13 O15 1.329(2) . ?
O15 C16 1.441(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.393(2) . ?
C17 C22 1.402(2) . ?
C18 C19 1.384(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.3919(19) . ?
C21 H21 0.9300 . ?
C22 C23 1.4955(19) . ?
C23 O24 1.1972(18) . ?
C23 O25 1.3323(19) . ?
O25 C26 1.450(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C10 S1 C11 92.05(8) . . ?
C2 C1 C6 119.06(15) . . ?
C2 C1 C10 125.01(13) . . ?
C6 C1 C10 115.92(14) . . ?
C3 C2 C1 119.43(14) . . ?
C3 C2 C17 116.70(13) . . ?
C1 C2 C17 123.83(13) . . ?
C4 C3 C2 121.19(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.76(18) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.11(16) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.43(16) . . ?
C5 C6 C7 120.58(15) . . ?
C1 C6 C7 119.88(16) . . ?
C8 C7 C6 112.53(13) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 109.69(14) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C12 112.49(15) . . ?
C10 C9 C8 119.19(16) . . ?
C12 C9 C8 128.31(15) . . ?
C9 C10 C1 122.68(14) . . ?
C9 C10 S1 110.92(13) . . ?
C1 C10 S1 126.40(11) . . ?
C12 C11 C13 127.35(16) . . ?
C12 C11 S1 111.13(14) . . ?
C13 C11 S1 121.53(14) . . ?
C11 C12 C9 113.41(15) . . ?
C11 C12 H12 123.3 . . ?
C9 C12 H12 123.3 . . ?
O14 C13 O15 124.1(2) . . ?
O14 C13 C11 124.5(2) . . ?
O15 C13 C11 111.44(15) . . ?
C13 O15 C16 117.09(16) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 117.87(13) . . ?
C18 C17 C2 119.42(13) . . ?
C22 C17 C2 122.36(12) . . ?
C19 C18 C17 121.36(15) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 120.22(14) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.65(14) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.74(15) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C17 120.14(13) . . ?
C21 C22 C23 119.00(13) . . ?
C17 C22 C23 120.65(12) . . ?
O24 C23 O25 123.58(14) . . ?
O24 C23 C22 124.74(14) . . ?
O25 C23 C22 111.65(12) . . ?
C23 O25 C26 116.24(14) . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C3 C2 C17 C22 -76.04(19) . . . . ?
C3 C2 C17 C18 97.07(18) . . . . ?
C1 C2 C17 C18 -80.43(19) . . . . ?
C1 C2 C17 C22 106.46(17) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_hb83_a
_database_code_depnum_ccdc_archive 'CCDC 1414607'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 O3 S'
_chemical_formula_weight         336.39

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'
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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1983(6)
_cell_length_b                   7.2853(3)
_cell_length_c                   14.9398(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.879(2)
_cell_angle_gamma                90
_cell_volume                     1634.37(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      29.82

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7263
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2014/2)'
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68540
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.713
_diffrn_reflns_theta_max         30.080
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4790
_reflns_number_gt                3977
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0548P)²+0.3429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4790
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_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
S1 S 0.68093(2) 0.37090(4) 0.49037(2) 0.03451(9) Uani 1 1 d . . . . .
C2 C 0.59490(7) 0.47190(17) 0.41867(7) 0.0374(2) Uani 1 1 d . . . . .
C3 C 0.61394(8) 0.64994(18) 0.39931(8) 0.0413(3) Uani 1 1 d . . . . .
H3 H 0.5749 0.7261 0.3623 0.050 Uiso 1 1 calc R U . . .
C4 C 0.69893(8) 0.70508(16) 0.44142(7) 0.0377(2) Uani 1 1 d . . . . .
C5 C 0.74385(7) 0.56780(15) 0.49384(7) 0.0317(2) Uani 1 1 d . . . . .
C6 C 0.83594(7) 0.59085(15) 0.53945(7) 0.0321(2) Uani 1 1 d . . . . .
C7 C 0.87678(7) 0.48551(15) 0.61340(7) 0.0334(2) Uani 1 1 d . . . . .
C8 C 0.96601(8) 0.51656(19) 0.64845(9) 0.0444(3) Uani 1 1 d . . . . .
H8 H 0.9930 0.4473 0.6974 0.053 Uiso 1 1 calc R U . . .
C9 C 1.01499(9) 0.6488(2) 0.61149(11) 0.0520(3) Uani 1 1 d . . . . .
H9 H 1.0746 0.6674 0.6350 0.062 Uiso 1 1 calc R U . . .
C10 C 0.97472(9) 0.75274(19) 0.53955(10) 0.0491(3) Uani 1 1 d . . . . .
H10 H 1.0079 0.8411 0.5147 0.059 Uiso 1 1 calc R U . . .
C11 C 0.88565(9) 0.72850(16) 0.50337(8) 0.0402(3) Uani 1 1 d . . . . .
C12 C 0.84169(11) 0.8438(2) 0.42468(9) 0.0543(4) Uani 1 1 d . . . . .
H12A H 0.8738 0.9585 0.4233 0.065 Uiso 1 1 calc R U . . .
H12B H 0.8445 0.7793 0.3684 0.065 Uiso 1 1 calc R U . . .
C13 C 0.74541(11) 0.88389(18) 0.43227(10) 0.0526(4) Uani 1 1 d . . . . .
H13A H 0.7421 0.9605 0.4848 0.063 Uiso 1 1 calc R U . . .
H13B H 0.7171 0.9486 0.3787 0.063 Uiso 1 1 calc R U . . .
C14 C 0.82932(7) 0.33803(15) 0.65565(7) 0.0326(2) Uani 1 1 d . . . . .
C15 C 0.75641(7) 0.37702(16) 0.69915(7) 0.0349(2) Uani 1 1 d . . . . .
C16 C 0.71563(8) 0.2371(2) 0.74102(8) 0.0443(3) Uani 1 1 d . . . . .
H16 H 0.6674 0.2635 0.7703 0.053 Uiso 1 1 calc R U . . .
C17 C 0.74673(9) 0.0587(2) 0.73929(9) 0.0490(3) Uani 1 1 d . . . . .
H17 H 0.7194 -0.0339 0.7678 0.059 Uiso 1 1 calc R U . . .
C18 C 0.81800(9) 0.01692(18) 0.69561(9) 0.0478(3) Uani 1 1 d . . . . .
H18 H 0.8380 -0.1034 0.6935 0.057 Uiso 1 1 calc R U . . .
C19 C 0.85919(8) 0.15710(17) 0.65500(8) 0.0406(3) Uani 1 1 d . . . . .
H19 H 0.9079 0.1299 0.6266 0.049 Uiso 1 1 calc R U . . .
O20 O 0.72849(6) 0.55531(13) 0.69995(6) 0.0448(2) Uani 1 1 d . . . . .
H20 H 0.6746 0.5579 0.7002 0.067 Uiso 1 1 calc R U . . .
C21 C 0.51466(8) 0.37061(19) 0.38170(8) 0.0424(3) Uani 1 1 d . . . . .
O22 O 0.45735(6) 0.42924(18) 0.32309(7) 0.0606(3) Uani 1 1 d . . . . .
O23 O 0.51287(7) 0.20389(16) 0.41798(7) 0.0565(3) Uani 1 1 d . . . . .
C24 C 0.43752(11) 0.0891(3) 0.38350(13) 0.0677(5) Uani 1 1 d . . . . .
H24A H 0.3835 0.1490 0.3930 0.102 Uiso 1 1 calc R U . . .
H24B H 0.4426 -0.0264 0.4148 0.102 Uiso 1 1 calc R U . . .
H24C H 0.4365 0.0687 0.3199 0.102 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
S1 C5 1.7204(11) . ?
S1 C2 1.7223(11) . ?
C2 C3 1.3695(18) . ?
C2 C21 1.4590(17) . ?
C3 C4 1.4053(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3838(15) . ?
C4 C13 1.4981(17) . ?
C5 C6 1.4686(15) . ?
C6 C7 1.4082(15) . ?
C6 C11 1.4116(15) . ?
C7 C8 1.3947(16) . ?
C7 C14 1.4878(15) . ?
C8 C9 1.3835(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.3893(19) . ?
C10 H10 0.9300 . ?
C11 C12 1.5137(18) . ?
C12 C13 1.514(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.3946(17) . ?
C14 C15 1.3977(16) . ?
C15 O20 1.3671(15) . ?
C15 C16 1.3905(16) . ?
C16 C17 1.385(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.3856(17) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O20 H20 0.8200 . ?
C21 O22 1.2134(16) . ?
C21 O23 1.3321(18) . ?
O23 C24 1.4469(17) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C5 S1 C2 91.58(6) . . ?
C3 C2 C21 126.20(11) . . ?
C3 C2 S1 111.78(9) . . ?
C21 C2 S1 121.96(10) . . ?
C2 C3 C4 112.70(11) . . ?
C2 C3 H3 123.7 . . ?
C4 C3 H3 123.7 . . ?
C5 C4 C3 112.70(11) . . ?
C5 C4 C13 118.80(11) . . ?
C3 C4 C13 128.43(11) . . ?
C4 C5 C6 122.11(10) . . ?
C4 C5 S1 111.23(8) . . ?
C6 C5 S1 126.50(8) . . ?
C7 C6 C11 119.32(10) . . ?
C7 C6 C5 125.09(9) . . ?
C11 C6 C5 115.59(10) . . ?
C8 C7 C6 119.44(10) . . ?
C8 C7 C14 117.70(10) . . ?
C6 C7 C14 122.85(9) . . ?
C9 C8 C7 121.00(12) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 119.49(12) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 121.48(11) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 119.25(11) . . ?
C10 C11 C12 121.22(11) . . ?
C6 C11 C12 119.52(11) . . ?
C13 C12 C11 111.40(11) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C4 C13 C12 108.29(11) . . ?
C4 C13 H13A 110.0 . . ?
C12 C13 H13A 110.0 . . ?
C4 C13 H13B 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C19 C14 C15 118.53(10) . . ?
C19 C14 C7 120.00(10) . . ?
C15 C14 C7 121.44(10) . . ?
O20 C15 C16 122.14(11) . . ?
O20 C15 C14 117.81(10) . . ?
C16 C15 C14 120.04(11) . . ?
C17 C16 C15 120.16(12) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.68(12) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 118.96(13) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 121.61(12) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C15 O20 H20 109.5 . . ?
O22 C21 O23 123.85(12) . . ?
O22 C21 C2 124.06(13) . . ?
O23 C21 C2 112.06(11) . . ?
C21 O23 C24 116.54(12) . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_af48
_database_code_depnum_ccdc_archive 'CCDC 1414608'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 Cl N O2 S'
_chemical_formula_weight         431.91

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   16.8761(6)
_cell_length_b                   16.8184(6)
_cell_length_c                   7.2259(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2050.92(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    304(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      24.62

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   0.7111
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.311
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2008/1)'
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_diffrn_ambient_temperature      304(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40845
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.211
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_full        25.042
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3582
_reflns_number_gt                3240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.967

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0415P)²+0.3529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1327 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.017(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3582
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
S1 S 0.03412(4) 0.72041(4) 0.36168(11) 0.04566(19) Uani 1 1 d . . . . .
Cl1 Cl -0.20718(6) 0.91569(5) 0.16319(15) 0.0723(3) Uani 1 1 d . . . . .
C1 C -0.14589(16) 0.76768(18) 0.2289(4) 0.0433(7) Uani 1 1 d . . . . .
C2 C -0.19430(18) 0.7104(2) 0.3099(5) 0.0565(8) Uani 1 1 d . . . . .
H2 H -0.2268 0.7243 0.4086 0.068 Uiso 1 1 calc R U . . .
C3 C -0.1945(2) 0.6334(2) 0.2456(6) 0.0670(10) Uani 1 1 d . . . . .
H3 H -0.2263 0.5953 0.3021 0.080 Uiso 1 1 calc R U . . .
C4 C -0.1475(2) 0.6130(2) 0.0969(5) 0.0632(9) Uani 1 1 d . . . . .
H4 H -0.1480 0.5612 0.0518 0.076 Uiso 1 1 calc R U . . .
C5 C -0.09972(18) 0.66923(18) 0.0154(5) 0.0524(8) Uani 1 1 d . . . . .
H5 H -0.0687 0.6551 -0.0858 0.063 Uiso 1 1 calc R U . . .
C6 C -0.09699(15) 0.74641(17) 0.0813(4) 0.0412(6) Uani 1 1 d . . . . .
C7 C -0.04514(16) 0.80712(18) -0.0110(4) 0.0434(7) Uani 1 1 d . . . . .
C8 C -0.06820(19) 0.8358(2) -0.1833(4) 0.0565(8) Uani 1 1 d . . . . .
H8 H -0.1135 0.8155 -0.2394 0.068 Uiso 1 1 calc R U . . .
C9 C -0.0248(2) 0.8939(2) -0.2722(5) 0.0622(9) Uani 1 1 d . . . . .
H9 H -0.0414 0.9128 -0.3868 0.075 Uiso 1 1 calc R U . . .
C10 C 0.04264(19) 0.9238(2) -0.1925(4) 0.0559(8) Uani 1 1 d . . . . .
H10 H 0.0711 0.9636 -0.2524 0.067 Uiso 1 1 calc R U . . .
C11 C 0.06891(17) 0.89506(17) -0.0223(4) 0.0468(7) Uani 1 1 d . . . . .
C12 C 0.02580(15) 0.83495(16) 0.0697(4) 0.0402(6) Uani 1 1 d . . . . .
C13 C 0.05925(16) 0.80665(17) 0.2440(4) 0.0419(6) Uani 1 1 d . . . . .
C14 C 0.11938(16) 0.84555(17) 0.3349(5) 0.0486(7) Uani 1 1 d . . . . .
C15 C 0.1496(2) 0.9229(2) 0.2619(6) 0.0760(12) Uani 1 1 d . . . . .
H15A H 0.1183 0.9661 0.3125 0.091 Uiso 1 1 calc R U . . .
H15B H 0.2041 0.9303 0.3008 0.091 Uiso 1 1 calc R U . . .
C16 C 0.14516(19) 0.9246(2) 0.0578(5) 0.0596(9) Uani 1 1 d . . . . .
H16A H 0.1881 0.8927 0.0086 0.072 Uiso 1 1 calc R U . . .
H16B H 0.1534 0.9789 0.0166 0.072 Uiso 1 1 calc R U . . .
C17 C 0.14381(17) 0.80615(18) 0.4966(5) 0.0506(7) Uani 1 1 d . . . . .
H17 H 0.1834 0.8258 0.5738 0.061 Uiso 1 1 calc R U . . .
C18 C 0.10483(15) 0.73697(16) 0.5310(4) 0.0420(6) Uani 1 1 d . . . . .
C19 C 0.11428(15) 0.68338(16) 0.6875(4) 0.0417(6) Uani 1 1 d . . . . .
C20 C 0.07585(19) 0.6100(2) 0.6957(5) 0.0566(8) Uani 1 1 d . . . . .
H20 H 0.0445 0.5938 0.5968 0.068 Uiso 1 1 calc R U . . .
C21 C 0.08353(19) 0.5610(2) 0.8480(6) 0.0614(8) Uani 1 1 d . . . . .
H21 H 0.0564 0.5129 0.8537 0.074 Uiso 1 1 calc R U . . .
C22 C 0.13167(18) 0.58419(19) 0.9903(4) 0.0509(7) Uani 1 1 d . . . . .
C23 C 0.17176(19) 0.6550(2) 0.9874(5) 0.0594(8) Uani 1 1 d . . . . .
H23 H 0.2046 0.6697 1.0850 0.071 Uiso 1 1 calc R U . . .
C24 C 0.16220(19) 0.70379(19) 0.8366(5) 0.0563(8) Uani 1 1 d . . . . .
H24 H 0.1887 0.7522 0.8342 0.068 Uiso 1 1 calc R U . . .
C28 C -0.14742(17) 0.85029(18) 0.3033(4) 0.0511(8) Uani 1 1 d . . . . .
H28A H -0.0937 0.8707 0.3086 0.061 Uiso 1 1 calc R U . . .
H28B H -0.1683 0.8494 0.4283 0.061 Uiso 1 1 calc R U . . .
N25 N 0.13961(18) 0.53301(19) 1.1526(5) 0.0694(8) Uani 1 1 d . . . . .
O26 O 0.0993(2) 0.4739(2) 1.1613(6) 0.1266(14) Uani 1 1 d . . . . .
O27 O 0.1869(2) 0.5506(2) 1.2719(4) 0.1036(11) 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 C18 1.731(3) . ?
S1 C13 1.734(3) . ?
Cl1 C28 1.803(3) . ?
C1 C2 1.392(4) . ?
C1 C6 1.395(4) . ?
C1 C28 1.490(4) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(4) . ?
C7 C8 1.391(4) . ?
C7 C12 1.412(4) . ?
C8 C9 1.379(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.412(4) . ?
C11 C16 1.496(4) . ?
C12 C13 1.460(4) . ?
C13 C14 1.374(4) . ?
C14 C17 1.405(5) . ?
C14 C15 1.493(5) . ?
C15 C16 1.477(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.360(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.455(4) . ?
C19 C24 1.390(4) . ?
C19 C20 1.396(4) . ?
C20 C21 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(5) . ?
C22 N25 1.461(4) . ?
C23 C24 1.374(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
N25 O26 1.206(4) . ?
N25 O27 1.211(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 S1 C13 92.48(14) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 C28 118.9(3) . . ?
C6 C1 C28 121.7(3) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 120.7(3) . . ?
C8 C7 C12 119.5(3) . . ?
C8 C7 C6 118.1(3) . . ?
C12 C7 C6 122.4(3) . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 C16 120.0(3) . . ?
C12 C11 C16 119.9(3) . . ?
C7 C12 C11 118.7(3) . . ?
C7 C12 C13 125.2(3) . . ?
C11 C12 C13 116.1(3) . . ?
C14 C13 C12 122.9(3) . . ?
C14 C13 S1 110.2(2) . . ?
C12 C13 S1 127.0(2) . . ?
C13 C14 C17 112.9(3) . . ?
C13 C14 C15 119.9(3) . . ?
C17 C14 C15 127.2(3) . . ?
C16 C15 C14 110.6(3) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C11 115.0(3) . . ?
C15 C16 H16A 108.5 . . ?
C11 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C11 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C14 114.4(3) . . ?
C18 C17 H17 122.8 . . ?
C14 C17 H17 122.8 . . ?
C17 C18 C19 128.2(3) . . ?
C17 C18 S1 110.0(2) . . ?
C19 C18 S1 121.7(2) . . ?
C24 C19 C20 117.1(3) . . ?
C24 C19 C18 120.9(3) . . ?
C20 C19 C18 122.0(3) . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 119.0(3) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 122.0(3) . . ?
C21 C22 N25 119.4(3) . . ?
C23 C22 N25 118.6(3) . . ?
C22 C23 C24 118.3(3) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C23 C24 C19 122.4(3) . . ?
C23 C24 H24 118.8 . . ?
C19 C24 H24 118.8 . . ?
C1 C28 Cl1 112.1(2) . . ?
C1 C28 H28A 109.2 . . ?
Cl1 C28 H28A 109.2 . . ?
C1 C28 H28B 109.2 . . ?
Cl1 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
O26 N25 O27 122.4(4) . . ?
O26 N25 C22 118.4(3) . . ?
O27 N25 C22 119.2(3) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_af49
_database_code_depnum_ccdc_archive 'CCDC 1414609'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 Cl N O2 S'
_chemical_formula_weight         429.90

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.864(3)
_cell_length_b                   7.2505(13)
_cell_length_c                   32.735(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4002.5(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2132
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      18.63

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   0.5697
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.318
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2008/1)'
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36215
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_av_R_equivalents  0.1607
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.244
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_full        25.096
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3539
_reflns_number_gt                2168
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1459P)²+86.1269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3539
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2009
_refine_ls_R_factor_gt           0.1412
_refine_ls_wR_factor_ref         0.4273
_refine_ls_wR_factor_gt          0.3957
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.000
_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
S1 S 0.47279(18) 0.9824(4) 0.36259(9) 0.0320(8) Uani 1 1 d . . . . .
Cl1 Cl 0.7099(2) 0.7641(4) 0.45964(10) 0.0437(9) Uani 1 1 d . . . . .
C1 C 0.6477(7) 0.8379(16) 0.3847(4) 0.033(3) Uani 1 1 d . . . . .
C2 C 0.6957(7) 0.9258(18) 0.3560(4) 0.041(3) Uani 1 1 d . . . . .
H2 H 0.7276 1.0273 0.3642 0.050 Uiso 1 1 calc R U . . .
C3 C 0.6976(9) 0.867(2) 0.3156(5) 0.054(4) Uani 1 1 d . . . . .
H3 H 0.7312 0.9267 0.2964 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6510(8) 0.7232(18) 0.3038(4) 0.042(3) Uani 1 1 d . . . . .
H4 H 0.6517 0.6853 0.2760 0.051 Uiso 1 1 calc R U . . .
C5 C 0.6029(8) 0.6310(18) 0.3311(4) 0.039(3) Uani 1 1 d . . . . .
H5 H 0.5728 0.5273 0.3225 0.047 Uiso 1 1 calc R U . . .
C6 C 0.5988(7) 0.6926(16) 0.3718(4) 0.031(3) Uani 1 1 d . . . . .
C7 C 0.5456(7) 0.5951(15) 0.4018(4) 0.032(3) Uani 1 1 d . . . . .
C8 C 0.5690(8) 0.4207(16) 0.4151(4) 0.043(3) Uani 1 1 d . . . . .
H8 H 0.6156 0.3663 0.4041 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5252(8) 0.3244(17) 0.4445(4) 0.043(3) Uani 1 1 d . . . . .
H9 H 0.5416 0.2052 0.4531 0.052 Uiso 1 1 calc R U . . .
C10 C 0.4591(8) 0.4022(17) 0.4606(4) 0.042(3) Uani 1 1 d . . . . .
H10 H 0.4306 0.3372 0.4811 0.050 Uiso 1 1 calc R U . . .
C11 C 0.4311(7) 0.5793(16) 0.4478(4) 0.034(3) Uani 1 1 d . . . . .
C12 C 0.4745(7) 0.6724(15) 0.4164(3) 0.029(3) Uani 1 1 d . . . . .
C13 C 0.4410(7) 0.8442(16) 0.4031(4) 0.032(3) Uani 1 1 d . . . . .
C14 C 0.3724(7) 0.9158(17) 0.4200(4) 0.033(3) Uani 1 1 d . . . . .
C15 C 0.3341(8) 0.8201(17) 0.4530(4) 0.038(3) Uani 1 1 d . . . . .
H15 H 0.2898 0.8741 0.4664 0.045 Uiso 1 1 calc R U . . .
C16 C 0.3609(7) 0.6552(15) 0.4649(4) 0.035(3) Uani 1 1 d . . . . .
H16 H 0.3325 0.5877 0.4850 0.042 Uiso 1 1 calc R U . . .
C17 C 0.3477(7) 1.0832(17) 0.4010(4) 0.035(3) Uani 1 1 d . . . . .
H17 H 0.3025 1.1515 0.4095 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3950(7) 1.1353(16) 0.3697(3) 0.031(3) Uani 1 1 d . . . . .
C19 C 0.3865(7) 1.2973(16) 0.3434(4) 0.029(3) Uani 1 1 d . . . . .
C20 C 0.4245(8) 1.3122(19) 0.3062(4) 0.044(3) Uani 1 1 d . . . . .
H20 H 0.4558 1.2118 0.2969 0.053 Uiso 1 1 calc R U . . .
C21 C 0.4186(8) 1.471(2) 0.2818(4) 0.048(4) Uani 1 1 d . . . . .
H21 H 0.4473 1.4814 0.2569 0.057 Uiso 1 1 calc R U . . .
C22 C 0.3695(7) 1.6097(16) 0.2954(4) 0.038(3) Uani 1 1 d . . . . .
C23 C 0.3296(7) 1.6042(17) 0.3321(4) 0.037(3) Uani 1 1 d . . . . .
H23 H 0.2974 1.7042 0.3409 0.044 Uiso 1 1 calc R U . . .
C24 C 0.3383(7) 1.4481(18) 0.3556(4) 0.040(3) Uani 1 1 d . . . . .
H24 H 0.3110 1.4410 0.3810 0.048 Uiso 1 1 calc R U . . .
N25 N 0.3613(7) 1.7737(14) 0.2697(4) 0.041(3) Uani 1 1 d . . . . .
O26 O 0.4031(8) 1.7906(16) 0.2403(4) 0.088(4) Uani 1 1 d . . . . .
O27 O 0.3131(7) 1.8920(14) 0.2788(3) 0.067(3) Uani 1 1 d . . . . .
C28 C 0.6472(7) 0.9045(16) 0.4278(4) 0.039(3) Uani 1 1 d . . . . .
H28A H 0.5923 0.9015 0.4384 0.047 Uiso 1 1 calc R U . . .
H28B H 0.6659 1.0339 0.4286 0.047 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
S1 C18 1.733(12) . ?
S1 C13 1.746(12) . ?
Cl1 C28 1.801(12) . ?
C1 C2 1.394(17) . ?
C1 C6 1.403(17) . ?
C1 C28 1.489(17) . ?
C2 C3 1.390(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.505(17) . ?
C7 C8 1.395(17) . ?
C7 C12 1.408(17) . ?
C8 C9 1.399(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.356(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.430(17) . ?
C10 H10 0.9500 . ?
C11 C16 1.420(17) . ?
C11 C12 1.432(16) . ?
C12 C13 1.436(16) . ?
C13 C14 1.384(16) . ?
C14 C17 1.426(17) . ?
C14 C15 1.436(16) . ?
C15 C16 1.336(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.353(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.463(17) . ?
C19 C20 1.380(17) . ?
C19 C24 1.420(16) . ?
C20 C21 1.403(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(18) . ?
C22 N25 1.462(15) . ?
C23 C24 1.377(18) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N25 O26 1.200(15) . ?
N25 O27 1.218(14) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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
C18 S1 C13 91.9(6) . . ?
C2 C1 C6 118.8(11) . . ?
C2 C1 C28 119.5(11) . . ?
C6 C1 C28 121.7(11) . . ?
C3 C2 C1 121.0(13) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 119.4(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.8(12) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 119.2(12) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.7(12) . . ?
C1 C6 C7 120.4(10) . . ?
C5 C6 C7 119.8(11) . . ?
C8 C7 C12 119.7(11) . . ?
C8 C7 C6 117.5(11) . . ?
C12 C7 C6 122.9(10) . . ?
C7 C8 C9 121.2(13) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.6(12) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 122.0(12) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C16 C11 C10 120.6(11) . . ?
C16 C11 C12 121.7(11) . . ?
C10 C11 C12 117.7(11) . . ?
C7 C12 C11 119.5(10) . . ?
C7 C12 C13 125.2(11) . . ?
C11 C12 C13 115.3(10) . . ?
C14 C13 C12 122.2(11) . . ?
C14 C13 S1 110.3(9) . . ?
C12 C13 S1 127.4(9) . . ?
C13 C14 C17 112.9(11) . . ?
C13 C14 C15 119.7(11) . . ?
C17 C14 C15 127.4(11) . . ?
C16 C15 C14 119.9(12) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.0(11) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C18 C17 C14 113.3(11) . . ?
C18 C17 H17 123.4 . . ?
C14 C17 H17 123.4 . . ?
C17 C18 C19 127.7(11) . . ?
C17 C18 S1 111.7(9) . . ?
C19 C18 S1 120.6(8) . . ?
C20 C19 C24 117.0(12) . . ?
C20 C19 C18 122.4(11) . . ?
C24 C19 C18 120.6(11) . . ?
C19 C20 C21 122.3(12) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C22 C21 C20 117.2(12) . . ?
C22 C21 H21 121.4 . . ?
C20 C21 H21 121.4 . . ?
C21 C22 C23 123.6(12) . . ?
C21 C22 N25 117.9(12) . . ?
C23 C22 N25 118.5(11) . . ?
C24 C23 C22 117.4(11) . . ?
C24 C23 H23 121.3 . . ?
C22 C23 H23 121.3 . . ?
C23 C24 C19 122.4(12) . . ?
C23 C24 H24 118.8 . . ?
C19 C24 H24 118.8 . . ?
O26 N25 O27 121.0(11) . . ?
O26 N25 C22 119.2(11) . . ?
O27 N25 C22 119.8(11) . . ?
C1 C28 Cl1 111.2(8) . . ?
C1 C28 H28A 109.4 . . ?
Cl1 C28 H28A 109.4 . . ?
C1 C28 H28B 109.4 . . ?
Cl1 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?

_refine_diff_density_max         2.140
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.162

