# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1532200'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H24 N2 O4 S'
_chemical_formula_iupac          'C15 H24 N2 O4 S'
_chemical_formula_weight         328.42

_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                   5.718(4)
_cell_length_b                   7.307(4)
_cell_length_c                   21.178(13)
_cell_angle_alpha                92.355(17)
_cell_angle_beta                 91.732(16)
_cell_angle_gamma                93.192(16)
_cell_volume                     882.3(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1879
_cell_measurement_theta_min      2.8853
_cell_measurement_theta_max      22.7842
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       PLATE
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.058
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352

_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Bruker X2S'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            8654
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         26.61
_diffrn_reflns_theta_full        26.61
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             3550
_reflns_number_gt                2108
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_gt          0.1841
_refine_ls_wR_factor_ref         0.2091
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     201
_refine_ls_number_restraints     12
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1054P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.400
_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       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
O O1 0.5617(4) 0.7705(3) 0.42397(13) 0.0562(7) Uani d . . . 1 . .
C C2 0.4660(5) 0.6152(5) 0.40788(16) 0.0421(8) Uani d . . . 1 . .
O O3 0.2692(4) 0.5589(3) 0.42528(12) 0.0566(7) Uani d . . . 1 . .
C C4 0.5930(5) 0.4892(4) 0.36446(15) 0.0378(7) Uani d . . . 1 . .
C C5 0.7831(6) 0.5519(5) 0.33161(16) 0.0462(8) Uani d . . . 1 . .
H H5 0.8345 0.6749 0.336 0.055 Uiso calc U . R 1 . .
C C6 0.8988(6) 0.4347(5) 0.29217(16) 0.0495(9) Uani d . . . 1 . .
H H6 1.0255 0.4788 0.2696 0.059 Uiso calc U . R 1 . .
C C7 0.8248(5) 0.2511(5) 0.28649(15) 0.0419(8) Uani d . . . 1 . .
C C8 0.6343(6) 0.1857(5) 0.31946(17) 0.0513(9) Uani d . . . 1 . .
H H8 0.5849 0.0622 0.3161 0.062 Uiso calc U . R 1 . .
C C9 0.5192(6) 0.3068(5) 0.35732(17) 0.0495(9) Uani d . . . 1 . .
H H9 0.3884 0.2643 0.3786 0.059 Uiso calc U . R 1 . .
S S10 0.97263(16) 0.09889(14) 0.23667(4) 0.0499(3) Uani d . . . 1 . .
O O11 1.1606(4) 0.2029(4) 0.20965(12) 0.0634(8) Uani d . . . 1 . .
O O12 1.0241(5) -0.0582(4) 0.27308(12) 0.0636(8) Uani d . . . 1 . .
N N13 0.7918(5) 0.0288(5) 0.17887(14) 0.0562(8) Uani d . . . 1 . .
C C14 0.6056(8) -0.1160(6) 0.1912(2) 0.0783(14) Uani d . . . 1 . .
H H14A 0.6488 -0.1763 0.2295 0.094 Uiso calc U . R 1 . .
H H14B 0.4599 -0.0578 0.1986 0.094 Uiso calc U . R 1 . .
C C15 0.5667(10) -0.2539(7) 0.1401(3) 0.1003(18) Uani d . . . 1 . .
H H15A 0.7092 -0.3178 0.1341 0.12 Uiso calc U . R 1 . .
H H15B 0.5298 -0.1943 0.1012 0.12 Uiso calc U . R 1 . .
C C16 0.3684(11) -0.3915(9) 0.1538(3) 0.125(2) Uani d . . . 1 . .
H H16A 0.3948 -0.4391 0.1948 0.188 Uiso calc U . R 1 . .
H H16B 0.362 -0.4903 0.1223 0.188 Uiso calc U . R 1 . .
H H16C 0.2227 -0.3322 0.1528 0.188 Uiso calc U . R 1 . .
C C17 0.7313(9) 0.1673(7) 0.1344(2) 0.0821(14) Uani d . . . 1 . .
H H17A 0.7751 0.288 0.1534 0.099 Uiso calc U . R 1 . .
H H17B 0.5629 0.1598 0.1267 0.099 Uiso calc U . R 1 . .
C C18 0.8512(13) 0.1456(10) 0.0717(3) 0.125(2) Uani d U . . 1 . .
H H18A 1.0195 0.1511 0.0796 0.15 Uiso calc U . R 1 . .
H H18B 0.8055 0.0255 0.0526 0.15 Uiso calc U . R 1 . .
C C19 0.7935(17) 0.2875(13) 0.0267(4) 0.187(4) Uani d U . . 1 . .
H H19A 0.6303 0.3108 0.0289 0.281 Uiso calc U . R 1 . .
H H19B 0.8264 0.245 -0.0154 0.281 Uiso calc U . R 1 . .
H H19C 0.8865 0.3985 0.0374 0.281 Uiso calc U . R 1 . .
N N21 0.0159(4) 0.8274(4) 0.46636(13) 0.0429(7) Uani d . . . 1 . .
H H21A -0.1326 0.8012 0.4538 0.051 Uiso calc U . R 1 . .
H H21B 0.1006 0.7366 0.4523 0.051 Uiso calc U . R 1 . .
C C22 0.0325(6) 0.8407(5) 0.53642(16) 0.0468(9) Uani d . . . 1 . .
H H22A 0.1956 0.8583 0.5504 0.056 Uiso calc U . R 1 . .
H H22B -0.0308 0.7273 0.5532 0.056 Uiso calc U . R 1 . .
C C23 0.1012(6) 1.0016(5) 0.43879(16) 0.0454(8) Uani d . . . 1 . .
H H23A 0.0822 0.9907 0.3931 0.054 Uiso calc U . R 1 . .
H H23B 0.2667 1.0249 0.4494 0.054 Uiso calc U . R 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
O1 C2 . 1.261(4) ?
C2 O3 . 1.248(4) ?
C2 C4 . 1.505(4) ?
C4 C5 . 1.376(4) ?
C4 C9 . 1.376(5) ?
C5 C6 . 1.381(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.383(5) ?
C6 H6 . 0.93 ?
C7 C8 . 1.385(5) ?
C7 S10 . 1.768(3) ?
C8 C9 . 1.377(4) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
S10 O11 . 1.429(3) ?
S10 O12 . 1.448(3) ?
S10 N13 . 1.626(3) ?
N13 C17 . 1.458(6) ?
N13 C14 . 1.496(5) ?
C14 C15 . 1.452(6) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.516(7) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 C18 . 1.519(7) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.481(9) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
N21 C22 . 1.483(4) ?
N21 C23 . 1.486(4) ?
N21 H21A . 0.89 ?
N21 H21B . 0.89 ?
C22 C23 2_576 1.503(5) ?
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?
C23 C22 2_576 1.503(5) ?
C23 H23A . 0.97 ?
C23 H23B . 0.97 ?

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
O3 C2 O1 . . 123.9(3) ?
O3 C2 C4 . . 117.2(3) ?
O1 C2 C4 . . 118.8(3) ?
C5 C4 C9 . . 118.8(3) ?
C5 C4 C2 . . 121.5(3) ?
C9 C4 C2 . . 119.7(3) ?
C4 C5 C6 . . 120.9(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C7 . . 119.5(3) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C6 C7 C8 . . 120.3(3) ?
C6 C7 S10 . . 120.0(2) ?
C8 C7 S10 . . 119.7(3) ?
C9 C8 C7 . . 118.8(3) ?
C9 C8 H8 . . 120.6 ?
C7 C8 H8 . . 120.6 ?
C4 C9 C8 . . 121.6(3) ?
C4 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
O11 S10 O12 . . 119.29(17) ?
O11 S10 N13 . . 106.95(17) ?
O12 S10 N13 . . 107.92(18) ?
O11 S10 C7 . . 107.35(17) ?
O12 S10 C7 . . 107.26(16) ?
N13 S10 C7 . . 107.57(16) ?
C17 N13 C14 . . 117.0(4) ?
C17 N13 S10 . . 115.7(3) ?
C14 N13 S10 . . 118.3(3) ?
C15 C14 N13 . . 113.8(4) ?
C15 C14 H14A . . 108.8 ?
N13 C14 H14A . . 108.8 ?
C15 C14 H14B . . 108.8 ?
N13 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.7 ?
C14 C15 C16 . . 111.5(5) ?
C14 C15 H15A . . 109.3 ?
C16 C15 H15A . . 109.3 ?
C14 C15 H15B . . 109.3 ?
C16 C15 H15B . . 109.3 ?
H15A C15 H15B . . 108.0 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N13 C17 C18 . . 113.0(5) ?
N13 C17 H17A . . 109.0 ?
C18 C17 H17A . . 109.0 ?
N13 C17 H17B . . 109.0 ?
C18 C17 H17B . . 109.0 ?
H17A C17 H17B . . 107.8 ?
C19 C18 C17 . . 113.3(6) ?
C19 C18 H18A . . 108.9 ?
C17 C18 H18A . . 108.9 ?
C19 C18 H18B . . 108.9 ?
C17 C18 H18B . . 108.9 ?
H18A C18 H18B . . 107.7 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C22 N21 C23 . . 111.3(2) ?
C22 N21 H21A . . 109.4 ?
C23 N21 H21A . . 109.4 ?
C22 N21 H21B . . 109.4 ?
C23 N21 H21B . . 109.4 ?
H21A N21 H21B . . 108.0 ?
N21 C22 C23 . 2_576 110.4(3) ?
N21 C22 H22A . . 109.6 ?
C23 C22 H22A 2_576 . 109.6 ?
N21 C22 H22B . . 109.6 ?
C23 C22 H22B 2_576 . 109.6 ?
H22A C22 H22B . . 108.1 ?
N21 C23 C22 . 2_576 110.7(3) ?
N21 C23 H23A . . 109.5 ?
C22 C23 H23A 2_576 . 109.5 ?
N21 C23 H23B . . 109.5 ?
C22 C23 H23B 2_576 . 109.5 ?
H23A C23 H23B . . 108.1 ?

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
O3 C2 C4 C5 . . . . 165.3(3) ?
O1 C2 C4 C5 . . . . -14.0(5) ?
O3 C2 C4 C9 . . . . -15.0(5) ?
O1 C2 C4 C9 . . . . 165.7(3) ?
C9 C4 C5 C6 . . . . -0.1(5) ?
C2 C4 C5 C6 . . . . 179.7(3) ?
C4 C5 C6 C7 . . . . -1.1(6) ?
C5 C6 C7 C8 . . . . 0.8(6) ?
C5 C6 C7 S10 . . . . -179.5(3) ?
C6 C7 C8 C9 . . . . 0.6(6) ?
S10 C7 C8 C9 . . . . -179.1(3) ?
C5 C4 C9 C8 . . . . 1.6(5) ?
C2 C4 C9 C8 . . . . -178.2(3) ?
C7 C8 C9 C4 . . . . -1.9(6) ?
C6 C7 S10 O11 . . . . 0.8(4) ?
C8 C7 S10 O11 . . . . -179.5(3) ?
C6 C7 S10 O12 . . . . 130.2(3) ?
C8 C7 S10 O12 . . . . -50.1(3) ?
C6 C7 S10 N13 . . . . -114.0(3) ?
C8 C7 S10 N13 . . . . 65.8(3) ?
O11 S10 N13 C17 . . . . -46.7(3) ?
O12 S10 N13 C17 . . . . -176.3(3) ?
C7 S10 N13 C17 . . . . 68.3(3) ?
O11 S10 N13 C14 . . . . 167.1(3) ?
O12 S10 N13 C14 . . . . 37.6(3) ?
C7 S10 N13 C14 . . . . -77.8(3) ?
C17 N13 C14 C15 . . . . 75.1(6) ?
S10 N13 C14 C15 . . . . -139.2(4) ?
N13 C14 C15 C16 . . . . -177.2(5) ?
C14 N13 C17 C18 . . . . -108.2(5) ?
S10 N13 C17 C18 . . . . 105.3(4) ?
N13 C17 C18 C19 . . . . -179.1(6) ?
C23 N21 C22 C23 . . . 2_576 56.7(4) ?
C22 N21 C23 C22 . . . 2_576 -56.8(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_I
_database_code_depnum_ccdc_archive 'CCDC 1532201'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Probenecid_4,4'-dipyridyl
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H23 N2 O4 S'
_chemical_formula_iupac          'C18 H23 N2 O4 S'
_chemical_formula_weight         363.44

_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                   5.3240(11)
_cell_length_b                   7.8906(14)
_cell_length_c                   23.599(5)
_cell_angle_alpha                85.158(9)
_cell_angle_beta                 83.687(7)
_cell_angle_gamma                70.746(6)
_cell_volume                     929.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2806
_cell_measurement_theta_min      2.6048
_cell_measurement_theta_max      23.2131
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       PLATE
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.396
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             386

_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Bruker X2S'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            10179
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29

_refine_special_details          
;
;

_reflns_number_total             3717
_reflns_number_gt                2644
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1615
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         3717
_refine_ls_number_parameters     275
_refine_ls_number_restraints     12
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+0.6973P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.477
_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       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
O O1 1.5797(5) 0.3121(4) 0.33747(14) 0.0990(10) Uani d . . . 1.0 . .
C C2 1.4402(8) 0.4579(7) 0.35326(18) 0.0858(13) Uani d . . . 1.0 . .
O O3 1.4805(5) 0.5347(4) 0.39633(12) 0.1037(10) Uani d . . . 1.0 . .
H H3 1.6132 0.4687 0.4111 0.156 Uiso calc U . R 1.0 . .
C C4 1.1982(5) 0.5715(4) 0.32347(12) 0.0525(7) Uani d . . . 1.0 . .
C C5 1.1030(6) 0.4904(4) 0.28535(13) 0.0550(7) Uani d . . . 1.0 . .
H H5 1.1826 0.3683 0.2799 0.066 Uiso calc U . R 1.0 . .
C C6 0.8902(5) 0.5890(4) 0.25521(12) 0.0486(7) Uani d . . . 1.0 . .
H H6 0.8245 0.5332 0.2299 0.058 Uiso calc U . R 1.0 . .
C C7 0.7741(5) 0.7719(3) 0.26271(10) 0.0402(6) Uani d . . . 1.0 . .
C C8 0.8645(5) 0.8549(4) 0.30166(11) 0.0487(7) Uani d . . . 1.0 . .
H H8 0.7847 0.9769 0.3073 0.058 Uiso calc U . R 1.0 . .
C C9 1.0757(6) 0.7530(4) 0.33197(12) 0.0560(8) Uani d . . . 1.0 . .
H H9 1.137 0.8071 0.3586 0.067 Uiso calc U . R 1.0 . .
S S10 0.52116(13) 0.90208(10) 0.21944(3) 0.0488(2) Uani d . . . 1.0 . .
O O11 0.3443(4) 1.0448(3) 0.25226(9) 0.0624(6) Uani d . . . 1.0 . .
O O12 0.4185(4) 0.7816(3) 0.19502(9) 0.0651(6) Uani d . . . 1.0 . .
N N13 0.6670(5) 0.9935(3) 0.16748(10) 0.0554(6) Uani d . . . 1.0 . .
C C14 0.8389(7) 0.8712(5) 0.12475(13) 0.0696(9) Uani d . . . 1.0 . .
H H14A 0.8888 0.7491 0.1412 0.084 Uiso calc U . R 1.0 . .
H H14B 1.0011 0.9017 0.1151 0.084 Uiso calc U . R 1.0 . .
C C15 0.7044(9) 0.8797(6) 0.07081(16) 0.0977(14) Uani d . . . 1.0 . .
H H15A 0.5416 0.8499 0.0804 0.117 Uiso calc U . R 1.0 . .
H H15B 0.6559 1.0015 0.0541 0.117 Uiso calc U . R 1.0 . .
C C16 0.8795(12) 0.7545(8) 0.02818(19) 0.139(2) Uani d . . . 1.0 . .
H H16A 1.0445 0.7797 0.0199 0.208 Uiso calc U . R 1.0 . .
H H16B 0.7916 0.77 -0.0062 0.208 Uiso calc U . R 1.0 . .
H H16C 0.9152 0.6329 0.0433 0.208 Uiso calc U . R 1.0 . .
C C17 0.7509(7) 1.1477(4) 0.17966(15) 0.0682(9) Uani d . . . 1.0 . .
H H17A 0.9384 1.1037 0.1866 0.082 Uiso calc U . R 1.0 . .
H H17B 0.6503 1.2007 0.2142 0.082 Uiso calc U . R 1.0 . .
C C18 0.7102(9) 1.2908(5) 0.13197(17) 0.0865(11) Uani d . . . 1.0 . .
H H18A 0.7856 1.3805 0.1411 0.104 Uiso calc U . R 1.0 . .
H H18B 0.8079 1.2367 0.0973 0.104 Uiso calc U . R 1.0 . .
C C19 0.4296(10) 1.3808(6) 0.1210(2) 0.1180(17) Uani d . . . 1.0 . .
H H19A 0.356 1.2945 0.1095 0.177 Uiso calc U . R 1.0 . .
H H19B 0.4191 1.4728 0.0912 0.177 Uiso calc U . R 1.0 . .
H H19C 0.3303 1.4339 0.1551 0.177 Uiso calc U . R 1.0 . .
C C20 0.3815(5) 0.0568(3) 0.48578(11) 0.0437(6) Uani d . . . 1.0 . .
C C21A 0.392(4) 0.026(2) 0.4252(9) 0.047(3) Uani d . P . 0.41(2) A 1
H H21A 0.5435 -0.054 0.4072 0.056 Uiso calc U P R 0.41(2) A 1
C C22A 0.178(4) 0.114(2) 0.3955(6) 0.056(4) Uani d . P . 0.41(2) A 1
H H22A 0.1884 0.0939 0.357 0.068 Uiso calc U P R 0.41(2) A 1
N N23A -0.044(2) 0.228(3) 0.4188(9) 0.061(5) Uani d . P . 0.41(2) A 1
C C24A -0.056(2) 0.252(2) 0.4735(10) 0.071(5) Uani d . P . 0.41(2) A 1
H H24A -0.2126 0.3313 0.49 0.086 Uiso calc U P R 0.41(2) A 1
C C25A 0.147(3) 0.169(2) 0.5081(8) 0.058(4) Uani d . P . 0.41(2) A 1
H H25A 0.123 0.1908 0.5468 0.07 Uiso calc U P R 0.41(2) A 1
C C21B 0.311(3) 0.0448(19) 0.4345(7) 0.071(4) Uani d . P . 0.59(2) A 2
H H21B 0.4168 -0.0486 0.4122 0.086 Uiso calc U P R 0.59(2) A 2
C C22B 0.085(2) 0.1664(15) 0.4132(6) 0.066(3) Uani d . P . 0.59(2) A 2
H H22B 0.0489 0.153 0.3765 0.079 Uiso calc U P R 0.59(2) A 2
N N23B -0.0818(17) 0.2997(13) 0.4418(4) 0.0517(18) Uani d . P . 0.59(2) A 2
C C24B -0.020(2) 0.3168(15) 0.4924(4) 0.076(3) Uani d . P . 0.59(2) A 2
H H24B -0.1344 0.4093 0.5139 0.091 Uiso calc U P R 0.59(2) A 2
C C25B 0.210(3) 0.2041(18) 0.5160(5) 0.068(3) Uani d U P . 0.59(2) A 2
H H25B 0.2493 0.226 0.5515 0.082 Uiso calc U P R 0.59(2) A 2


_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
O1 C2 . 1.209(5) ?
C2 O3 . 1.298(5) ?
C2 C4 . 1.513(4) ?
O3 H3 . 0.82 ?
C4 C5 . 1.373(4) ?
C4 C9 . 1.386(4) ?
C5 C6 . 1.377(4) ?
C5 H5 . 0.93 ?
C6 C7 . 1.388(4) ?
C6 H6 . 0.93 ?
C7 C8 . 1.383(4) ?
C7 S10 . 1.767(3) ?
C8 C9 . 1.381(4) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
S10 O12 . 1.428(2) ?
S10 O11 . 1.429(2) ?
S10 N13 . 1.624(3) ?
N13 C14 . 1.471(4) ?
N13 C17 . 1.486(4) ?
C14 C15 . 1.514(5) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.487(6) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 C18 . 1.505(5) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.469(6) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 C21B . 1.325(19) ?
C20 C25A . 1.351(18) ?
C20 C25B . 1.411(14) ?
C20 C21A . 1.46(2) ?
C20 C20 2_656 1.478(5) ?
C21A C22A . 1.36(3) ?
C21A H21A . 0.93 ?
C22A N23A . 1.319(15) ?
C22A H22A . 0.93 ?
N23A C24A . 1.312(19) ?
C24A C25A . 1.38(2) ?
C24A H24A . 0.93 ?
C25A H25A . 0.93 ?
C21B C22B . 1.383(18) ?
C21B H21B . 0.93 ?
C22B N23B . 1.312(12) ?
C22B H22B . 0.93 ?
N23B C24B . 1.301(10) ?
C24B C25B . 1.393(14) ?
C24B H24B . 0.93 ?
C25B H25B . 0.93 ?

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
O1 C2 O3 . . 124.7(3) ?
O1 C2 C4 . . 122.5(4) ?
O3 C2 C4 . . 112.8(4) ?
C2 O3 H3 . . 109.5 ?
C5 C4 C9 . . 119.4(3) ?
C5 C4 C2 . . 117.9(3) ?
C9 C4 C2 . . 122.7(3) ?
C4 C5 C6 . . 120.4(3) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C7 . . 119.8(3) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C8 C7 C6 . . 120.5(2) ?
C8 C7 S10 . . 119.6(2) ?
C6 C7 S10 . . 119.8(2) ?
C9 C8 C7 . . 118.7(3) ?
C9 C8 H8 . . 120.7 ?
C7 C8 H8 . . 120.7 ?
C8 C9 C4 . . 121.2(3) ?
C8 C9 H9 . . 119.4 ?
C4 C9 H9 . . 119.4 ?
O12 S10 O11 . . 119.80(13) ?
O12 S10 N13 . . 107.29(14) ?
O11 S10 N13 . . 107.05(13) ?
O12 S10 C7 . . 107.60(13) ?
O11 S10 C7 . . 107.88(12) ?
N13 S10 C7 . . 106.52(12) ?
C14 N13 C17 . . 116.6(3) ?
C14 N13 S10 . . 116.1(2) ?
C17 N13 S10 . . 118.3(2) ?
N13 C14 C15 . . 112.8(3) ?
N13 C14 H14A . . 109.0 ?
C15 C14 H14A . . 109.0 ?
N13 C14 H14B . . 109.0 ?
C15 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
C16 C15 C14 . . 112.2(4) ?
C16 C15 H15A . . 109.2 ?
C14 C15 H15A . . 109.2 ?
C16 C15 H15B . . 109.2 ?
C14 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N13 C17 C18 . . 113.2(3) ?
N13 C17 H17A . . 108.9 ?
C18 C17 H17A . . 108.9 ?
N13 C17 H17B . . 108.9 ?
C18 C17 H17B . . 108.9 ?
H17A C17 H17B . . 107.7 ?
C19 C18 C17 . . 114.3(4) ?
C19 C18 H18A . . 108.7 ?
C17 C18 H18A . . 108.7 ?
C19 C18 H18B . . 108.7 ?
C17 C18 H18B . . 108.7 ?
H18A C18 H18B . . 107.6 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C21B C20 C25B . . 114.5(7) ?
C25A C20 C21A . . 115.2(9) ?
C21B C20 C20 . 2_656 129.2(7) ?
C25A C20 C20 . 2_656 130.1(8) ?
C25B C20 C20 . 2_656 116.2(5) ?
C21A C20 C20 . 2_656 114.3(8) ?
C22A C21A C20 . . 119.5(12) ?
C22A C21A H21A . . 120.2 ?
C20 C21A H21A . . 120.2 ?
N23A C22A C21A . . 123.1(13) ?
N23A C22A H22A . . 118.5 ?
C21A C22A H22A . . 118.5 ?
C24A N23A C22A . . 117.5(11) ?
N23A C24A C25A . . 124.7(12) ?
N23A C24A H24A . . 117.7 ?
C25A C24A H24A . . 117.7 ?
C20 C25A C24A . . 119.9(13) ?
C20 C25A H25A . . 120.0 ?
C24A C25A H25A . . 120.0 ?
C20 C21B C22B . . 122.1(11) ?
C20 C21B H21B . . 118.9 ?
C22B C21B H21B . . 118.9 ?
N23B C22B C21B . . 123.8(10) ?
N23B C22B H22B . . 118.1 ?
C21B C22B H22B . . 118.1 ?
C24B N23B C22B . . 116.1(7) ?
N23B C24B C25B . . 123.6(8) ?
N23B C24B H24B . . 118.2 ?
C25B C24B H24B . . 118.2 ?
C24B C25B C20 . . 119.8(8) ?
C24B C25B H25B . . 120.1 ?
C20 C25B H25B . . 120.1 ?

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
O1 C2 C4 C5 . . . . 14.0(5) ?
O3 C2 C4 C5 . . . . -166.6(3) ?
O1 C2 C4 C9 . . . . -164.1(3) ?
O3 C2 C4 C9 . . . . 15.3(4) ?
C9 C4 C5 C6 . . . . 0.9(4) ?
C2 C4 C5 C6 . . . . -177.2(3) ?
C4 C5 C6 C7 . . . . 1.0(4) ?
C5 C6 C7 C8 . . . . -2.2(4) ?
C5 C6 C7 S10 . . . . 174.3(2) ?
C6 C7 C8 C9 . . . . 1.3(4) ?
S10 C7 C8 C9 . . . . -175.2(2) ?
C7 C8 C9 C4 . . . . 0.7(4) ?
C5 C4 C9 C8 . . . . -1.8(4) ?
C2 C4 C9 C8 . . . . 176.3(3) ?
C8 C7 S10 O12 . . . . -165.0(2) ?
C6 C7 S10 O12 . . . . 18.4(3) ?
C8 C7 S10 O11 . . . . -34.5(3) ?
C6 C7 S10 O11 . . . . 149.0(2) ?
C8 C7 S10 N13 . . . . 80.2(2) ?
C6 C7 S10 N13 . . . . -96.4(2) ?
O12 S10 N13 C14 . . . . -44.2(2) ?
O11 S10 N13 C14 . . . . -174.0(2) ?
C7 S10 N13 C14 . . . . 70.8(2) ?
O12 S10 N13 C17 . . . . 169.7(2) ?
O11 S10 N13 C17 . . . . 39.9(2) ?
C7 S10 N13 C17 . . . . -75.3(2) ?
C17 N13 C14 C15 . . . . -112.4(4) ?
S10 N13 C14 C15 . . . . 100.9(3) ?
N13 C14 C15 C16 . . . . -179.6(4) ?
C14 N13 C17 C18 . . . . 72.3(4) ?
S10 N13 C17 C18 . . . . -141.8(3) ?
N13 C17 C18 C19 . . . . 64.2(5) ?
C25A C20 C21A C22A . . . . 2.8(14) ?
C20 C20 C21A C22A 2_656 . . . 175.9(8) ?
C20 C21A C22A N23A . . . . -0.7(16) ?
C21A C22A N23A C24A . . . . -1.0(17) ?
C22A N23A C24A C25A . . . . 0.6(17) ?
C21A C20 C25A C24A . . . . -3.2(14) ?
C20 C20 C25A C24A 2_656 . . . -175.0(8) ?
N23A C24A C25A C20 . . . . 1.7(17) ?
C25B C20 C21B C22B . . . . -0.7(13) ?
C20 C20 C21B C22B 2_656 . . . -177.9(7) ?
C20 C21B C22B N23B . . . . -2.0(15) ?
C21B C22B N23B C24B . . . . 2.0(14) ?
C22B N23B C24B C25B . . . . 0.6(13) ?
N23B C24B C25B C20 . . . . -3.2(14) ?
C21B C20 C25B C24B . . . . 3.1(12) ?
C20 C20 C25B C24B 2_656 . . . -179.4(7) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1532202'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 N2 O4 S'
_chemical_formula_iupac          'C26 H28 N2 O4 S'
_chemical_formula_weight         464.56

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.4752(7)
_cell_length_b                   31.526(3)
_cell_length_c                   10.6100(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.799(3)
_cell_angle_gamma                90
_cell_volume                     2487.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6829
_cell_measurement_theta_min      2.5806
_cell_measurement_theta_max      24.4314
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'fluorescent yellow'
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.189
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984

_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Bruker X2S'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            27198
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             5107
_reflns_number_gt                3788
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1166
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_number_reflns         5107
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.6338P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_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         0.161
_refine_diff_density_min         -0.348
_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       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
O O1 0.3079(2) 0.43688(5) 0.76380(16) 0.0814(5) Uani d . . . 1 . .
C C2 0.2430(3) 0.40895(6) 0.69630(18) 0.0495(5) Uani d . . . 1 . .
O O3 0.07378(19) 0.39822(5) 0.68682(15) 0.0681(4) Uani d . . . 1 . .
H H3 0.0185 0.4146 0.7288 0.102 Uiso calc U . R 1 . .
C C4 0.3551(2) 0.38344(5) 0.61431(16) 0.0421(4) Uani d . . . 1 . .
C C5 0.5397(2) 0.38748(6) 0.63181(17) 0.0481(4) Uani d . . . 1 . .
H H5 0.5917 0.4056 0.6943 0.058 Uiso calc U . R 1 . .
C C6 0.6484(2) 0.36500(6) 0.55788(17) 0.0458(4) Uani d . . . 1 . .
H H6 0.7728 0.3677 0.5706 0.055 Uiso calc U . R 1 . .
C C7 0.5694(2) 0.33826(5) 0.46446(15) 0.0380(4) Uani d . . . 1 . .
C C8 0.3836(2) 0.33419(6) 0.44518(17) 0.0449(4) Uani d . . . 1 . .
H H8 0.3314 0.3164 0.3818 0.054 Uiso calc U . R 1 . .
C C9 0.2767(2) 0.35669(6) 0.52062(17) 0.0464(4) Uani d . . . 1 . .
H H9 0.1523 0.3539 0.5086 0.056 Uiso calc U . R 1 . .
S S10 0.70525(6) 0.30710(2) 0.37324(4) 0.04000(13) Uani d . . . 1 . .
O O11 0.87658(17) 0.32733(4) 0.37504(13) 0.0555(3) Uani d . . . 1 . .
O O12 0.60189(18) 0.29866(4) 0.25530(11) 0.0547(4) Uani d . . . 1 . .
N N13 0.73826(19) 0.26230(4) 0.44684(13) 0.0428(3) Uani d . . . 1 . .
C C14 0.8604(3) 0.26321(7) 0.56618(18) 0.0525(5) Uani d . . . 1 . .
H H14A 0.804 0.2481 0.6313 0.063 Uiso calc U . R 1 . .
H H14B 0.8773 0.2924 0.5936 0.063 Uiso calc U . R 1 . .
C C15 1.0408(3) 0.24379(9) 0.5535(2) 0.0736(7) Uani d . . . 1 . .
H H15A 1.099 0.2589 0.4892 0.088 Uiso calc U . R 1 . .
H H15B 1.0254 0.2145 0.5267 0.088 Uiso calc U . R 1 . .
C C16 1.1586(3) 0.24563(11) 0.6784(2) 0.1007(10) Uani d . . . 1 . .
H H16A 1.1775 0.2747 0.7033 0.151 Uiso calc U . R 1 . .
H H16B 1.2723 0.2325 0.6688 0.151 Uiso calc U . R 1 . .
H H16C 1.1005 0.2309 0.7421 0.151 Uiso calc U . R 1 . .
C C17 0.5819(3) 0.23334(6) 0.4481(2) 0.0543(5) Uani d . . . 1 . .
H H17A 0.4932 0.2407 0.3785 0.065 Uiso calc U . R 1 . .
H H17B 0.5273 0.2375 0.5263 0.065 Uiso calc U . R 1 . .
C C18 0.6308(4) 0.18769(7) 0.4370(3) 0.0806(7) Uani d . . . 1 . .
H H18A 0.7256 0.1807 0.503 0.097 Uiso calc U . R 1 . .
H H18B 0.6765 0.1829 0.3559 0.097 Uiso calc U . R 1 . .
C C19 0.4711(5) 0.15901(8) 0.4485(3) 0.1026(10) Uani d . . . 1 . .
H H19A 0.4302 0.1624 0.5308 0.154 Uiso calc U . R 1 . .
H H19B 0.5058 0.13 0.4372 0.154 Uiso calc U . R 1 . .
H H19C 0.3759 0.1664 0.3847 0.154 Uiso calc U . R 1 . .
N N21 0.8883(2) 0.44465(5) 0.82908(15) 0.0467(4) Uani d . . . 1 . .
C C22 0.8954(2) 0.43735(6) 0.95489(18) 0.0453(4) Uani d . . . 1 . .
C C23 0.9831(3) 0.40030(6) 1.0072(2) 0.0619(5) Uani d . . . 1 . .
H H23 1.0359 0.3814 0.9546 0.074 Uiso calc U . R 1 . .
C C24 0.9899(3) 0.39240(7) 1.1325(2) 0.0751(7) Uani d . . . 1 . .
H H24 1.046 0.3679 1.1651 0.09 Uiso calc U . R 1 . .
C C25 0.9137(3) 0.42066(8) 1.2151(2) 0.0733(7) Uani d . . . 1 . .
H H25 0.9201 0.4146 1.3012 0.088 Uiso calc U . R 1 . .
C C26 0.8318(3) 0.45627(7) 1.1701(2) 0.0615(5) Uani d . . . 1 . .
H H26 0.7839 0.475 1.2256 0.074 Uiso calc U . R 1 . .
C C27 0.8176(2) 0.46572(6) 1.03811(17) 0.0460(4) Uani d . . . 1 . .
C C28 0.7308(2) 0.50150(6) 0.9854(2) 0.0504(5) Uani d . . . 1 . .
H H28 0.6801 0.5208 1.0378 0.06 Uiso calc U . R 1 . .
C C29 0.7187(2) 0.50885(6) 0.85613(19) 0.0477(4) Uani d . . . 1 . .
C C30 0.6268(3) 0.54426(7) 0.7962(3) 0.0659(6) Uani d . . . 1 . .
H H30 0.5726 0.5641 0.845 0.079 Uiso calc U . R 1 . .
C C31 0.6176(3) 0.54932(8) 0.6694(3) 0.0791(7) Uani d . . . 1 . .
H H31 0.5555 0.5723 0.6315 0.095 Uiso calc U . R 1 . .
C C32 0.7010(4) 0.52017(8) 0.5944(2) 0.0777(7) Uani d . . . 1 . .
H H32 0.6935 0.5242 0.5072 0.093 Uiso calc U . R 1 . .
C C33 0.7922(3) 0.48630(7) 0.6464(2) 0.0629(5) Uani d . . . 1 . .
H H33 0.8484 0.4676 0.5951 0.075 Uiso calc U . R 1 . .
C C34 0.8022(2) 0.47924(6) 0.77908(18) 0.0463(4) Uani 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
O1 C2 . 1.205(2) ?
C2 O3 . 1.304(2) ?
C2 C4 . 1.501(2) ?
O3 H3 . 0.82 ?
C4 C5 . 1.380(2) ?
C4 C9 . 1.387(2) ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.387(2) ?
C6 H6 . 0.93 ?
C7 C8 . 1.389(2) ?
C7 S10 . 1.7697(16) ?
C8 C9 . 1.383(2) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
S10 O12 . 1.4276(13) ?
S10 O11 . 1.4291(13) ?
S10 N13 . 1.6206(15) ?
N13 C14 . 1.485(2) ?
N13 C17 . 1.484(2) ?
C14 C15 . 1.499(3) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.516(3) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 C18 . 1.492(3) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.512(4) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
N21 C34 . 1.348(2) ?
N21 C22 . 1.350(2) ?
C22 C27 . 1.422(2) ?
C22 C23 . 1.424(3) ?
C23 C24 . 1.349(3) ?
C23 H23 . 0.93 ?
C24 C25 . 1.410(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.343(3) ?
C25 H25 . 0.93 ?
C26 C27 . 1.425(3) ?
C26 H26 . 0.93 ?
C27 C28 . 1.390(3) ?
C28 C29 . 1.385(3) ?
C28 H28 . 0.93 ?
C29 C34 . 1.425(3) ?
C29 C30 . 1.427(3) ?
C30 C31 . 1.349(3) ?
C30 H30 . 0.93 ?
C31 C32 . 1.403(4) ?
C31 H31 . 0.93 ?
C32 C33 . 1.354(3) ?
C32 H32 . 0.93 ?
C33 C34 . 1.420(3) ?
C33 H33 . 0.93 ?

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
O1 C2 O3 . . 124.37(17) ?
O1 C2 C4 . . 121.41(18) ?
O3 C2 C4 . . 114.23(15) ?
C2 O3 H3 . . 109.5 ?
C5 C4 C9 . . 119.78(16) ?
C5 C4 C2 . . 118.81(15) ?
C9 C4 C2 . . 121.41(16) ?
C4 C5 C6 . . 120.95(16) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C5 C6 C7 . . 119.03(16) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
C6 C7 C8 . . 120.58(16) ?
C6 C7 S10 . . 120.12(13) ?
C8 C7 S10 . . 119.24(13) ?
C9 C8 C7 . . 119.68(16) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C8 C9 C4 . . 119.98(16) ?
C8 C9 H9 . . 120.0 ?
C4 C9 H9 . . 120.0 ?
O12 S10 O11 . . 119.99(8) ?
O12 S10 N13 . . 107.60(8) ?
O11 S10 N13 . . 106.84(8) ?
O12 S10 C7 . . 107.06(8) ?
O11 S10 C7 . . 107.93(8) ?
N13 S10 C7 . . 106.75(8) ?
C14 N13 C17 . . 114.91(14) ?
C14 N13 S10 . . 116.41(12) ?
C17 N13 S10 . . 117.31(12) ?
N13 C14 C15 . . 113.38(16) ?
N13 C14 H14A . . 108.9 ?
C15 C14 H14A . . 108.9 ?
N13 C14 H14B . . 108.9 ?
C15 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
C14 C15 C16 . . 110.7(2) ?
C14 C15 H15A . . 109.5 ?
C16 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C16 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N13 C17 C18 . . 113.17(18) ?
N13 C17 H17A . . 108.9 ?
C18 C17 H17A . . 108.9 ?
N13 C17 H17B . . 108.9 ?
C18 C17 H17B . . 108.9 ?
H17A C17 H17B . . 107.8 ?
C17 C18 C19 . . 111.6(2) ?
C17 C18 H18A . . 109.3 ?
C19 C18 H18A . . 109.3 ?
C17 C18 H18B . . 109.3 ?
C19 C18 H18B . . 109.3 ?
H18A C18 H18B . . 108.0 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C34 N21 C22 . . 119.78(15) ?
N21 C22 C27 . . 121.93(17) ?
N21 C22 C23 . . 119.70(17) ?
C27 C22 C23 . . 118.37(18) ?
C24 C23 C22 . . 120.3(2) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C23 C24 C25 . . 121.3(2) ?
C23 C24 H24 . . 119.4 ?
C25 C24 H24 . . 119.4 ?
C26 C25 C24 . . 120.4(2) ?
C26 C25 H25 . . 119.8 ?
C24 C25 H25 . . 119.8 ?
C25 C26 C27 . . 120.7(2) ?
C25 C26 H26 . . 119.7 ?
C27 C26 H26 . . 119.7 ?
C28 C27 C22 . . 117.67(17) ?
C28 C27 C26 . . 123.36(18) ?
C22 C27 C26 . . 118.97(19) ?
C29 C28 C27 . . 120.98(17) ?
C29 C28 H28 . . 119.5 ?
C27 C28 H28 . . 119.5 ?
C28 C29 C34 . . 118.05(17) ?
C28 C29 C30 . . 123.55(19) ?
C34 C29 C30 . . 118.40(19) ?
C31 C30 C29 . . 120.7(2) ?
C31 C30 H30 . . 119.6 ?
C29 C30 H30 . . 119.6 ?
C30 C31 C32 . . 120.5(2) ?
C30 C31 H31 . . 119.7 ?
C32 C31 H31 . . 119.7 ?
C33 C32 C31 . . 121.3(2) ?
C33 C32 H32 . . 119.3 ?
C31 C32 H32 . . 119.3 ?
C32 C33 C34 . . 120.1(2) ?
C32 C33 H33 . . 120.0 ?
C34 C33 H33 . . 120.0 ?
N21 C34 C33 . . 119.48(18) ?
N21 C34 C29 . . 121.56(17) ?
C33 C34 C29 . . 118.96(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
O1 C2 C4 C5 . . . . 10.5(3) ?
O3 C2 C4 C5 . . . . -169.77(18) ?
O1 C2 C4 C9 . . . . -168.4(2) ?
O3 C2 C4 C9 . . . . 11.4(3) ?
C9 C4 C5 C6 . . . . -0.5(3) ?
C2 C4 C5 C6 . . . . -179.35(17) ?
C4 C5 C6 C7 . . . . 0.4(3) ?
C5 C6 C7 C8 . . . . 0.1(3) ?
C5 C6 C7 S10 . . . . -176.96(14) ?
C6 C7 C8 C9 . . . . -0.6(3) ?
S10 C7 C8 C9 . . . . 176.52(14) ?
C7 C8 C9 C4 . . . . 0.5(3) ?
C5 C4 C9 C8 . . . . 0.0(3) ?
C2 C4 C9 C8 . . . . 178.85(17) ?
C6 C7 S10 O12 . . . . -154.48(14) ?
C8 C7 S10 O12 . . . . 28.37(16) ?
C6 C7 S10 O11 . . . . -24.03(17) ?
C8 C7 S10 O11 . . . . 158.83(14) ?
C6 C7 S10 N13 . . . . 90.52(15) ?
C8 C7 S10 N13 . . . . -86.63(15) ?
O12 S10 N13 C14 . . . . 173.56(12) ?
O11 S10 N13 C14 . . . . 43.47(14) ?
C7 S10 N13 C14 . . . . -71.81(13) ?
O12 S10 N13 C17 . . . . -44.66(15) ?
O11 S10 N13 C17 . . . . -174.75(13) ?
C7 S10 N13 C17 . . . . 69.97(14) ?
C17 N13 C14 C15 . . . . 111.03(19) ?
S10 N13 C14 C15 . . . . -106.28(18) ?
N13 C14 C15 C16 . . . . -179.9(2) ?
C14 N13 C17 C18 . . . . -75.1(2) ?
S10 N13 C17 C18 . . . . 142.56(17) ?
N13 C17 C18 C19 . . . . 175.7(2) ?
C34 N21 C22 C27 . . . . -1.4(2) ?
C34 N21 C22 C23 . . . . 178.63(16) ?
N21 C22 C23 C24 . . . . -179.41(19) ?
C27 C22 C23 C24 . . . . 0.6(3) ?
C22 C23 C24 C25 . . . . -1.0(4) ?
C23 C24 C25 C26 . . . . 0.1(4) ?
C24 C25 C26 C27 . . . . 1.2(3) ?
N21 C22 C27 C28 . . . . 0.7(3) ?
C23 C22 C27 C28 . . . . -179.30(16) ?
N21 C22 C27 C26 . . . . -179.35(16) ?
C23 C22 C27 C26 . . . . 0.6(3) ?
C25 C26 C27 C28 . . . . 178.39(19) ?
C25 C26 C27 C22 . . . . -1.5(3) ?
C22 C27 C28 C29 . . . . 0.9(3) ?
C26 C27 C28 C29 . . . . -179.08(17) ?
C27 C28 C29 C34 . . . . -1.7(3) ?
C27 C28 C29 C30 . . . . 178.03(17) ?
C28 C29 C30 C31 . . . . -179.0(2) ?
C34 C29 C30 C31 . . . . 0.7(3) ?
C29 C30 C31 C32 . . . . -1.1(4) ?
C30 C31 C32 C33 . . . . 0.1(4) ?
C31 C32 C33 C34 . . . . 1.2(4) ?
C22 N21 C34 C33 . . . . -178.80(16) ?
C22 N21 C34 C29 . . . . 0.5(3) ?
C32 C33 C34 N21 . . . . 177.82(19) ?
C32 C33 C34 C29 . . . . -1.5(3) ?
C28 C29 C34 N21 . . . . 1.0(3) ?
C30 C29 C34 N21 . . . . -178.71(16) ?
C28 C29 C34 C33 . . . . -179.68(17) ?
C30 C29 C34 C33 . . . . 0.6(3) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1532203'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            PROBENECID_PYRIDINE
_chemical_formula_moiety         'C18 H24 N2 O4 S'
_chemical_formula_sum            'C18 H24 N2 O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         364.45

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.4241(8)
_cell_length_b                   6.9988(8)
_cell_length_c                   37.621(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.210(4)
_cell_angle_gamma                90
_cell_volume                     1949.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4946
_cell_measurement_theta_min      2.9565
_cell_measurement_theta_max      23.0814
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.179
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776

_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Bruker X2S'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            16375
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       46

_refine_special_details          
;
;

_reflns_number_total             3895
_reflns_number_gt                2773
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0876
_refine_ls_wR_factor_gt          0.2346
_refine_ls_wR_factor_ref         0.2566
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_number_reflns         3895
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1276P)²+1.2427P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.459
_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       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
O O1 0.4925(4) 0.7305(5) 0.52107(9) 0.0999(10) Uani d . . D 1 . .
H H1 0.5645 0.7423 0.5064 0.12 Uiso d U . DR 1 . .
C C2 0.5704(6) 0.6787(7) 0.55158(12) 0.0848(11) Uani d . . . 1 . .
O O3 0.7300(4) 0.6667(8) 0.55747(10) 0.1466(18) Uani d . . . 1 . .
C C4 0.4419(5) 0.6347(5) 0.57904(10) 0.0670(9) Uani d . . . 1 . .
C C5 0.2557(5) 0.6597(5) 0.57291(10) 0.0681(9) Uani d . . . 1 . .
H H5 0.2076 0.7018 0.5508 0.082 Uiso calc U . R 1 . .
C C6 0.1429(4) 0.6223(5) 0.59960(10) 0.0665(9) Uani d . . . 1 . .
H H6 0.0187 0.6379 0.5954 0.08 Uiso calc U . R 1 . .
C C7 0.2154(4) 0.5613(4) 0.63267(9) 0.0600(8) Uani d . . . 1 . .
C C8 0.4003(5) 0.5333(5) 0.63864(11) 0.0714(10) Uani d . . . 1 . .
H H8 0.4488 0.4908 0.6607 0.086 Uiso calc U . R 1 . .
C C9 0.5104(5) 0.5688(6) 0.61181(11) 0.0770(11) Uani d . . . 1 . .
H H9 0.634 0.548 0.6158 0.092 Uiso calc U . R 1 . .
S S10 0.07270(12) 0.52204(13) 0.66748(3) 0.0695(4) Uani d . . . 1 . .
O O11 -0.0957(4) 0.4550(4) 0.65168(8) 0.0899(9) Uani d . . . 1 . .
O O12 0.1697(4) 0.4099(5) 0.69374(8) 0.0990(10) Uani d . . . 1 . .
N N13 0.0368(4) 0.7276(5) 0.68491(9) 0.0780(9) Uani d . . . 1 . .
C C14 -0.0844(6) 0.8647(7) 0.66403(14) 0.0998(14) Uani d . . . 1 . .
H H14A -0.0154 0.9782 0.6591 0.12 Uiso calc U . R 1 . .
H H14B -0.1228 0.8066 0.6413 0.12 Uiso calc U . R 1 . .
C C15 -0.2435(7) 0.9219(9) 0.68158(16) 0.1112(16) Uani d . . . 1 . .
H H15A -0.2066 0.9879 0.7036 0.133 Uiso calc U . R 1 . .
H H15B -0.3108 0.809 0.6875 0.133 Uiso calc U . R 1 . .
C C16 -0.3645(6) 1.0521(7) 0.65803(17) 0.1154(18) Uani d . . . 1 . .
H H16A -0.4683 1.0873 0.6704 0.173 Uiso calc U . R 1 . .
H H16B -0.2988 1.165 0.6524 0.173 Uiso calc U . R 1 . .
H H16C -0.403 0.9863 0.6364 0.173 Uiso calc U . R 1 . .
C C17 0.2025(8) 0.8272(11) 0.70460(15) 0.133(2) Uani d . . . 1 . .
H H17A 0.3096 0.7497 0.7026 0.16 Uiso calc U . R 1 . .
H H17B 0.2225 0.9503 0.6937 0.16 Uiso calc U . R 1 . .
C C18 0.1724(9) 0.8517(14) 0.73952(17) 0.153(3) Uani d . . . 1 . .
H H18A 0.1564 0.7286 0.7507 0.184 Uiso calc U . R 1 . .
H H18B 0.0635 0.9263 0.7415 0.184 Uiso calc U . R 1 . .
C C19 0.3419(9) 0.9603(10) 0.75902(16) 0.141(2) Uani d . . . 1 . .
H H19A 0.3219 0.9783 0.7837 0.212 Uiso calc U . R 1 . .
H H19B 0.4491 0.8854 0.7571 0.212 Uiso calc U . R 1 . .
H H19C 0.3564 1.0824 0.7479 0.212 Uiso calc U . R 1 . .
N N21 0.7383(6) 0.7902(6) 0.47481(11) 0.0949(11) Uani d . . . 1 . .
C C22 0.7004(8) 0.8411(7) 0.44142(16) 0.1058(15) Uani d . . . 1 . .
H H22 0.5806 0.8637 0.4336 0.127 Uiso calc U . R 1 . .
C C23 0.8323(11) 0.8623(7) 0.41760(15) 0.1155(19) Uani d . . . 1 . .
H H23 0.8003 0.8969 0.3941 0.139 Uiso calc U . R 1 . .
C C24 1.0077(10) 0.8326(8) 0.42848(19) 0.1190(19) Uani d . . . 1 . .
H H24 1.0979 0.847 0.4128 0.143 Uiso calc U . R 1 . .
C C25 1.0491(8) 0.7804(11) 0.4633(2) 0.136(2) Uani d . . . 1 . .
H H25 1.1682 0.7605 0.472 0.163 Uiso calc U . R 1 . .
C C26 0.9062(7) 0.7582(10) 0.48552(14) 0.1147(18) Uani d . . . 1 . .
H H26 0.9329 0.7187 0.5089 0.138 Uiso calc U . R 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
O1 C2 . 1.299(5) ?
O1 H1 . 0.8005 ?
C2 O3 . 1.192(5) ?
C2 C4 . 1.489(6) ?
C4 C9 . 1.378(5) ?
C4 C5 . 1.395(5) ?
C5 C6 . 1.379(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.387(5) ?
C6 H6 . 0.93 ?
C7 C8 . 1.388(5) ?
C7 S10 . 1.765(4) ?
C8 C9 . 1.367(6) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
S10 O12 . 1.417(3) ?
S10 O11 . 1.424(3) ?
S10 N13 . 1.611(3) ?
N13 C14 . 1.498(5) ?
N13 C17 . 1.554(7) ?
C14 C15 . 1.451(7) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.518(7) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 C18 . 1.360(8) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.601(9) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
N21 C26 . 1.301(6) ?
N21 C22 . 1.316(7) ?
C22 C23 . 1.382(7) ?
C22 H22 . 0.93 ?
C23 C24 . 1.352(8) ?
C23 H23 . 0.93 ?
C24 C25 . 1.375(8) ?
C24 H24 . 0.93 ?
C25 C26 . 1.406(8) ?
C25 H25 . 0.93 ?
C26 H26 . 0.93 ?

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 O1 H1 . . 111.2 ?
O3 C2 O1 . . 123.8(4) ?
O3 C2 C4 . . 122.3(4) ?
O1 C2 C4 . . 113.9(3) ?
C9 C4 C5 . . 119.1(4) ?
C9 C4 C2 . . 118.5(3) ?
C5 C4 C2 . . 122.5(4) ?
C6 C5 C4 . . 120.2(3) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 119.7(3) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C6 C7 C8 . . 120.2(4) ?
C6 C7 S10 . . 119.9(3) ?
C8 C7 S10 . . 119.9(3) ?
C9 C8 C7 . . 119.5(3) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C8 C9 C4 . . 121.3(3) ?
C8 C9 H9 . . 119.3 ?
C4 C9 H9 . . 119.3 ?
O12 S10 O11 . . 119.6(2) ?
O12 S10 N13 . . 107.6(2) ?
O11 S10 N13 . . 107.31(18) ?
O12 S10 C7 . . 107.54(18) ?
O11 S10 C7 . . 107.34(17) ?
N13 S10 C7 . . 106.83(17) ?
C14 N13 C17 . . 112.7(4) ?
C14 N13 S10 . . 118.0(3) ?
C17 N13 S10 . . 116.5(3) ?
C15 C14 N13 . . 114.6(4) ?
C15 C14 H14A . . 108.6 ?
N13 C14 H14A . . 108.6 ?
C15 C14 H14B . . 108.6 ?
N13 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
C14 C15 C16 . . 111.5(5) ?
C14 C15 H15A . . 109.3 ?
C16 C15 H15A . . 109.3 ?
C14 C15 H15B . . 109.3 ?
C16 C15 H15B . . 109.3 ?
H15A C15 H15B . . 108.0 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 N13 . . 109.7(6) ?
C18 C17 H17A . . 109.7 ?
N13 C17 H17A . . 109.7 ?
C18 C17 H17B . . 109.7 ?
N13 C17 H17B . . 109.7 ?
H17A C17 H17B . . 108.2 ?
C17 C18 C19 . . 108.9(6) ?
C17 C18 H18A . . 109.9 ?
C19 C18 H18A . . 109.9 ?
C17 C18 H18B . . 109.9 ?
C19 C18 H18B . . 109.9 ?
H18A C18 H18B . . 108.3 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C26 N21 C22 . . 118.4(5) ?
N21 C22 C23 . . 122.4(6) ?
N21 C22 H22 . . 118.8 ?
C23 C22 H22 . . 118.8 ?
C24 C23 C22 . . 120.0(6) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C23 C24 C25 . . 118.2(6) ?
C23 C24 H24 . . 120.9 ?
C25 C24 H24 . . 120.9 ?
C24 C25 C26 . . 118.0(6) ?
C24 C25 H25 . . 121.0 ?
C26 C25 H25 . . 121.0 ?
N21 C26 C25 . . 123.0(5) ?
N21 C26 H26 . . 118.5 ?
C25 C26 H26 . . 118.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 C2 C4 C9 . . . . -3.2(7) ?
O1 C2 C4 C9 . . . . 176.7(4) ?
O3 C2 C4 C5 . . . . 176.0(5) ?
O1 C2 C4 C5 . . . . -4.0(6) ?
C9 C4 C5 C6 . . . . 1.2(5) ?
C2 C4 C5 C6 . . . . -178.0(3) ?
C4 C5 C6 C7 . . . . 0.6(5) ?
C5 C6 C7 C8 . . . . -1.6(5) ?
C5 C6 C7 S10 . . . . 177.5(3) ?
C6 C7 C8 C9 . . . . 0.8(5) ?
S10 C7 C8 C9 . . . . -178.3(3) ?
C7 C8 C9 C4 . . . . 1.0(6) ?
C5 C4 C9 C8 . . . . -2.0(6) ?
C2 C4 C9 C8 . . . . 177.3(4) ?
C6 C7 S10 O12 . . . . 163.0(3) ?
C8 C7 S10 O12 . . . . -17.8(3) ?
C6 C7 S10 O11 . . . . 33.1(3) ?
C8 C7 S10 O11 . . . . -147.8(3) ?
C6 C7 S10 N13 . . . . -81.8(3) ?
C8 C7 S10 N13 . . . . 97.4(3) ?
O12 S10 N13 C14 . . . . -172.3(3) ?
O11 S10 N13 C14 . . . . -42.4(4) ?
C7 S10 N13 C14 . . . . 72.5(3) ?
O12 S10 N13 C17 . . . . 48.8(4) ?
O11 S10 N13 C17 . . . . 178.7(3) ?
C7 S10 N13 C17 . . . . -66.4(4) ?
C17 N13 C14 C15 . . . . -99.7(5) ?
S10 N13 C14 C15 . . . . 119.9(4) ?
N13 C14 C15 C16 . . . . -176.9(4) ?
C14 N13 C17 C18 . . . . 100.7(7) ?
S10 N13 C17 C18 . . . . -118.3(6) ?
N13 C17 C18 C19 . . . . -178.3(5) ?
C26 N21 C22 C23 . . . . -0.3(8) ?
N21 C22 C23 C24 . . . . -0.8(8) ?
C22 C23 C24 C25 . . . . 0.4(9) ?
C23 C24 C25 C26 . . . . 1.0(10) ?
C22 N21 C26 C25 . . . . 1.8(9) ?
C24 C25 C26 N21 . . . . -2.1(10) ?

