# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1573540'
_audit_update_record             
;
2017-09-09 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N2 O6 S'
_chemical_formula_weight         396.45

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

_space_group_crystal_system      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                   10.9782(13)
_cell_length_b                   11.2330(14)
_cell_length_c                   16.728(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2062.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5906
_cell_measurement_theta_min      2.1839
_cell_measurement_theta_max      26.9900

_exptl_crystal_description       bolck
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11642
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         25.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3684
_reflns_number_gt                3349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.987

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0517P)²+0.2589P] 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 1350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3684
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.89977(6) 0.16660(7) 0.16824(4) 0.0475(2) Uani 1 1 d . . . . .
O1 O 0.8452(3) 0.4701(2) 0.44347(19) 0.0915(10) Uani 1 1 d . . . . .
O2 O 0.9790(3) 0.4543(3) 0.5348(2) 0.1143(13) Uani 1 1 d . . . . .
O3 O 0.39842(17) -0.19393(19) 0.19218(13) 0.0548(5) Uani 1 1 d . . . . .
O4 O 0.56689(17) -0.28496(18) 0.22886(14) 0.0532(5) Uani 1 1 d . . . . .
O5 O 0.71721(17) -0.18530(16) 0.30356(13) 0.0492(5) Uani 1 1 d . . . . .
O6 O 0.9697(2) 0.2754(3) 0.18825(16) 0.0834(8) Uani 1 1 d . . . . .
N1 N 0.9212(3) 0.4127(3) 0.47943(17) 0.0597(7) Uani 1 1 d . . . . .
N2 N 0.79365(19) 0.1374(2) 0.23631(12) 0.0380(5) Uani 1 1 d . . . . .
H2 H 0.7208 0.1646 0.2314 0.046 Uiso 1 1 calc R U . . .
C1 C 0.8281(2) 0.0639(2) 0.30494(15) 0.0354(5) Uani 1 1 d . . . . .
H1 H 0.8758 -0.0037 0.2852 0.043 Uiso 1 1 calc R U . . .
C2 C 0.9015(2) 0.1256(2) 0.36978(15) 0.0351(5) Uani 1 1 d . . . . .
C3 C 0.8808(2) 0.2437(2) 0.39142(15) 0.0384(6) Uani 1 1 d . . . . .
H3 H 0.8261 0.2908 0.3631 0.046 Uiso 1 1 calc R U . . .
C4 C 0.9439(2) 0.2890(3) 0.45626(17) 0.0436(7) Uani 1 1 d . . . . .
C5 C 1.0260(3) 0.2235(3) 0.50011(18) 0.0526(8) Uani 1 1 d . . . . .
H5 H 1.0665 0.2567 0.5435 0.063 Uiso 1 1 calc R U . . .
C6 C 1.0464(3) 0.1067(3) 0.47764(19) 0.0582(8) Uani 1 1 d . . . . .
H6 H 1.1011 0.0599 0.5063 0.070 Uiso 1 1 calc R U . . .
C7 C 0.9857(3) 0.0595(3) 0.41264(18) 0.0490(7) Uani 1 1 d . . . . .
H7 H 1.0016 -0.0185 0.3973 0.059 Uiso 1 1 calc R U . . .
C8 C 0.7097(2) 0.0147(2) 0.34278(16) 0.0416(6) Uani 1 1 d . . . . .
H8A H 0.7277 -0.0142 0.3961 0.050 Uiso 1 1 calc R U . . .
H8B H 0.6513 0.0790 0.3478 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6542(2) -0.0829(2) 0.29578(15) 0.0380(6) Uani 1 1 d . . . . .
C10 C 0.5525(2) -0.0775(2) 0.25229(17) 0.0414(6) Uani 1 1 d . . . . .
H10 H 0.5156 -0.0043 0.2426 0.050 Uiso 1 1 calc R U . . .
C11 C 0.4997(2) -0.1845(2) 0.22041(15) 0.0412(6) Uani 1 1 d . . . . .
C12 C 0.6972(3) -0.2730(3) 0.2429(2) 0.0540(8) Uani 1 1 d . . . . .
C13 C 0.7607(3) -0.2365(4) 0.1676(3) 0.0798(12) Uani 1 1 d . . . . .
H13A H 0.7471 -0.2955 0.1270 0.120 Uiso 1 1 calc R U . . .
H13B H 0.7293 -0.1613 0.1498 0.120 Uiso 1 1 calc R U . . .
H13C H 0.8465 -0.2294 0.1775 0.120 Uiso 1 1 calc R U . . .
C14 C 0.7395(4) -0.3904(3) 0.2773(3) 0.0932(16) Uani 1 1 d . . . . .
H14A H 0.7278 -0.4523 0.2385 0.140 Uiso 1 1 calc R U . . .
H14B H 0.8243 -0.3851 0.2908 0.140 Uiso 1 1 calc R U . . .
H14C H 0.6932 -0.4083 0.3245 0.140 Uiso 1 1 calc R U . . .
C15 C 0.7976(3) 0.2098(3) 0.08536(16) 0.0500(7) Uani 1 1 d . . . . .
C16 C 0.7242(4) 0.3182(4) 0.1084(2) 0.0815(12) Uani 1 1 d . . . . .
H16A H 0.7783 0.3827 0.1208 0.122 Uiso 1 1 calc R U . . .
H16B H 0.6723 0.3406 0.0647 0.122 Uiso 1 1 calc R U . . .
H16C H 0.6752 0.3001 0.1544 0.122 Uiso 1 1 calc R U . . .
C17 C 0.8850(4) 0.2382(4) 0.01608(19) 0.0712(10) Uani 1 1 d . . . . .
H17A H 0.9306 0.1681 0.0025 0.107 Uiso 1 1 calc R U . . .
H17B H 0.8390 0.2639 -0.0296 0.107 Uiso 1 1 calc R U . . .
H17C H 0.9400 0.3002 0.0320 0.107 Uiso 1 1 calc R U . . .
C18 C 0.7191(4) 0.1023(4) 0.0646(2) 0.0826(13) Uani 1 1 d . . . . .
H18A H 0.7705 0.0365 0.0505 0.124 Uiso 1 1 calc R U . . .
H18B H 0.6700 0.0811 0.1099 0.124 Uiso 1 1 calc R U . . .
H18C H 0.6671 0.1216 0.0203 0.124 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 O6 1.481(3) . ?
S1 N2 1.662(2) . ?
S1 C15 1.848(3) . ?
O1 N1 1.214(4) . ?
O2 N1 1.216(4) . ?
O3 C11 1.213(3) . ?
O4 C11 1.355(3) . ?
O4 C12 1.456(3) . ?
O5 C9 1.349(3) . ?
O5 C12 1.431(4) . ?
N1 C4 1.463(4) . ?
N2 C1 1.463(3) . ?
C1 C2 1.519(3) . ?
C1 C8 1.547(4) . ?
C2 C7 1.386(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.383(5) . ?
C6 C7 1.381(4) . ?
C8 C9 1.480(4) . ?
C9 C10 1.334(4) . ?
C10 C11 1.437(4) . ?
C12 C13 1.497(5) . ?
C12 C14 1.512(5) . ?
C15 C16 1.510(5) . ?
C15 C18 1.524(5) . ?
C15 C17 1.538(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
O6 S1 N2 111.81(14) . . ?
O6 S1 C15 105.51(15) . . ?
N2 S1 C15 98.08(12) . . ?
C11 O4 C12 118.3(2) . . ?
C9 O5 C12 116.1(2) . . ?
O1 N1 O2 122.1(3) . . ?
O1 N1 C4 119.3(3) . . ?
O2 N1 C4 118.6(3) . . ?
C1 N2 S1 117.91(16) . . ?
N2 C1 C2 116.1(2) . . ?
N2 C1 C8 107.8(2) . . ?
C2 C1 C8 108.4(2) . . ?
C7 C2 C3 119.0(3) . . ?
C7 C2 C1 118.6(2) . . ?
C3 C2 C1 122.3(2) . . ?
C4 C3 C2 118.2(3) . . ?
C5 C4 C3 123.3(3) . . ?
C5 C4 N1 118.6(3) . . ?
C3 C4 N1 118.1(3) . . ?
C4 C5 C6 118.0(3) . . ?
C7 C6 C5 120.0(3) . . ?
C6 C7 C2 121.6(3) . . ?
C9 C8 C1 113.1(2) . . ?
C10 C9 O5 121.4(2) . . ?
C10 C9 C8 126.9(3) . . ?
O5 C9 C8 111.7(2) . . ?
C9 C10 C11 120.1(3) . . ?
O3 C11 O4 117.8(3) . . ?
O3 C11 C10 125.9(3) . . ?
O4 C11 C10 116.0(2) . . ?
O5 C12 O4 109.2(2) . . ?
O5 C12 C13 109.7(3) . . ?
O4 C12 C13 110.3(3) . . ?
O5 C12 C14 106.4(3) . . ?
O4 C12 C14 106.4(3) . . ?
C13 C12 C14 114.6(3) . . ?
C16 C15 C18 113.3(3) . . ?
C16 C15 C17 111.0(3) . . ?
C18 C15 C17 110.2(3) . . ?
C16 C15 S1 110.1(2) . . ?
C18 C15 S1 107.8(2) . . ?
C17 C15 S1 104.0(2) . . ?

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
O6 S1 N2 C1 -88.6(2) . . . . ?
C15 S1 N2 C1 161.04(19) . . . . ?
S1 N2 C1 C2 77.0(2) . . . . ?
S1 N2 C1 C8 -161.19(18) . . . . ?
N2 C1 C2 C7 -148.1(2) . . . . ?
C8 C1 C2 C7 90.4(3) . . . . ?
N2 C1 C2 C3 36.6(3) . . . . ?
C8 C1 C2 C3 -84.9(3) . . . . ?
C7 C2 C3 C4 -1.4(4) . . . . ?
C1 C2 C3 C4 173.8(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 N1 -179.4(3) . . . . ?
O1 N1 C4 C5 -176.9(3) . . . . ?
O2 N1 C4 C5 2.6(5) . . . . ?
O1 N1 C4 C3 2.8(4) . . . . ?
O2 N1 C4 C3 -177.8(3) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
N1 C4 C5 C6 179.9(3) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C5 C6 C7 C2 -1.6(5) . . . . ?
C3 C2 C7 C6 2.1(4) . . . . ?
C1 C2 C7 C6 -173.3(3) . . . . ?
N2 C1 C8 C9 75.1(3) . . . . ?
C2 C1 C8 C9 -158.5(2) . . . . ?
C12 O5 C9 C10 21.6(4) . . . . ?
C12 O5 C9 C8 -160.5(2) . . . . ?
C1 C8 C9 C10 -108.0(3) . . . . ?
C1 C8 C9 O5 74.3(3) . . . . ?
O5 C9 C10 C11 7.4(4) . . . . ?
C8 C9 C10 C11 -170.1(3) . . . . ?
C12 O4 C11 O3 164.5(3) . . . . ?
C12 O4 C11 C10 -20.5(4) . . . . ?
C9 C10 C11 O3 166.6(3) . . . . ?
C9 C10 C11 O4 -7.9(4) . . . . ?
C9 O5 C12 O4 -46.4(3) . . . . ?
C9 O5 C12 C13 74.6(3) . . . . ?
C9 O5 C12 C14 -160.9(3) . . . . ?
C11 O4 C12 O5 46.6(4) . . . . ?
C11 O4 C12 C13 -74.1(3) . . . . ?
C11 O4 C12 C14 161.1(3) . . . . ?
O6 S1 C15 C16 -53.5(3) . . . . ?
N2 S1 C15 C16 61.9(3) . . . . ?
O6 S1 C15 C18 -177.6(3) . . . . ?
N2 S1 C15 C18 -62.2(3) . . . . ?
O6 S1 C15 C17 65.5(3) . . . . ?
N2 S1 C15 C17 -179.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.86 2.42 3.077(3) 133.2 3_655
C3 H3 O3 0.93 2.64 3.441(3) 145.0 3_655
C5 H5 O3 0.93 2.61 3.335(4) 134.9 2_655

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1573542'
_audit_update_record             
;
2017-09-09 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H29 Br N2 O5 S'
_chemical_formula_weight         561.48

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0662(14)
_cell_length_b                   15.170(2)
_cell_length_c                   17.178(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2623.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3340
_cell_measurement_theta_min      2.3451
_cell_measurement_theta_max      21.0663

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    1.685
_shelx_estimated_absorpt_T_min   0.552
_shelx_estimated_absorpt_T_max   0.641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_T_max  0.641
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14738
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.791
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4588
_reflns_number_gt                3552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.999
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0113P)²] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.018(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4588
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
Br1 Br 1.00658(5) 0.10776(3) 0.96178(3) 0.05948(17) Uani 1 1 d . . . . .
S1 S 0.76076(11) 0.07912(7) 0.76224(7) 0.0437(3) Uani 1 1 d . . . . .
O1 O 0.8242(3) 0.42701(19) 0.88630(18) 0.0457(8) Uani 1 1 d . . . . .
O2 O 1.0214(3) 0.49752(18) 0.92782(17) 0.0467(7) Uani 1 1 d . . . . .
O3 O 1.1669(3) 0.4280(2) 1.0016(2) 0.0658(10) Uani 1 1 d . . . . .
O4 O 0.6610(3) 0.3064(2) 0.74928(19) 0.0533(9) Uani 1 1 d . . . . .
O5 O 0.8595(3) 0.0112(2) 0.7841(2) 0.0647(11) Uani 1 1 d . . . . .
N1 N 0.8876(3) 0.3115(2) 0.7340(2) 0.0383(9) Uani 1 1 d . . . . .
N2 N 0.7312(3) 0.1455(2) 0.8385(2) 0.0383(9) Uani 1 1 d . . . . .
H2 H 0.6746 0.1324 0.8742 0.046 Uiso 1 1 calc R U . . .
C1 C 0.8089(4) 0.2278(3) 0.8400(3) 0.0345(10) Uani 1 1 d . . . . .
C2 C 0.9584(4) 0.2198(2) 0.8320(2) 0.0324(10) Uani 1 1 d . . . . .
C3 C 0.9982(4) 0.2731(2) 0.7700(2) 0.0342(9) Uani 1 1 d . . . . .
C4 C 0.7720(4) 0.2851(3) 0.7688(3) 0.0384(11) Uani 1 1 d . . . . .
C5 C 1.0550(4) 0.1777(3) 0.8744(3) 0.0400(11) Uani 1 1 d . . . . .
C6 C 1.1876(5) 0.1875(3) 0.8558(3) 0.0513(14) Uani 1 1 d . . . . .
H6 H 1.2521 0.1576 0.8841 0.062 Uiso 1 1 calc R U . . .
C7 C 1.2241(5) 0.2415(3) 0.7953(3) 0.0542(14) Uani 1 1 d . . . . .
H7 H 1.3138 0.2488 0.7841 0.065 Uiso 1 1 calc R U . . .
C8 C 1.1315(4) 0.2853(3) 0.7507(3) 0.0466(13) Uani 1 1 d . . . . .
H8 H 1.1567 0.3214 0.7095 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8952(5) 0.3739(3) 0.6696(3) 0.0457(11) Uani 1 1 d . . . . .
H9A H 0.9573 0.4204 0.6830 0.055 Uiso 1 1 calc R U . . .
H9B H 0.8086 0.4007 0.6621 0.055 Uiso 1 1 calc R U . . .
C10 C 0.9386(5) 0.3320(3) 0.5943(3) 0.0435(11) Uani 1 1 d . . . . .
C11 C 1.0350(5) 0.3715(3) 0.5494(3) 0.0573(13) Uani 1 1 d . . . . .
H11 H 1.0797 0.4208 0.5680 0.069 Uiso 1 1 calc R U . . .
C12 C 1.0661(6) 0.3377(4) 0.4758(3) 0.0734(17) Uani 1 1 d . . . . .
H12 H 1.1293 0.3657 0.4449 0.088 Uiso 1 1 calc R U . . .
C13 C 1.0035(7) 0.2635(4) 0.4493(3) 0.0821(17) Uani 1 1 d . . . . .
H13 H 1.0242 0.2410 0.4004 0.099 Uiso 1 1 calc R U . . .
C14 C 0.9102(6) 0.2223(4) 0.4948(4) 0.0802(18) Uani 1 1 d . . . . .
H14 H 0.8690 0.1712 0.4773 0.096 Uiso 1 1 calc R U . . .
C15 C 0.8779(5) 0.2568(3) 0.5664(3) 0.0592(14) Uani 1 1 d . . . . .
H15 H 0.8138 0.2289 0.5966 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7682(4) 0.2777(3) 0.9154(2) 0.0428(11) Uani 1 1 d . . . . .
H16A H 0.6766 0.2969 0.9108 0.051 Uiso 1 1 calc R U . . .
H16B H 0.7738 0.2377 0.9593 0.051 Uiso 1 1 calc R U . . .
C17 C 0.8551(4) 0.3566(3) 0.9306(3) 0.0397(11) Uani 1 1 d . . . . .
C18 C 0.9596(5) 0.3581(3) 0.9783(3) 0.0463(12) Uani 1 1 d . . . . .
H18 H 0.9705 0.3133 1.0148 0.056 Uiso 1 1 calc R U . . .
C19 C 1.0558(5) 0.4282(3) 0.9739(3) 0.0463(11) Uani 1 1 d . . . . .
C20 C 0.8831(4) 0.5104(3) 0.9096(3) 0.0480(13) Uani 1 1 d . . . . .
C21 C 0.8792(5) 0.5704(3) 0.8403(4) 0.0728(17) Uani 1 1 d . . . . .
H21A H 0.9227 0.6249 0.8529 0.109 Uiso 1 1 calc R U . . .
H21B H 0.7885 0.5819 0.8264 0.109 Uiso 1 1 calc R U . . .
H21C H 0.9240 0.5429 0.7974 0.109 Uiso 1 1 calc R U . . .
C22 C 0.8106(5) 0.5451(3) 0.9805(3) 0.0704(17) Uani 1 1 d . . . . .
H22A H 0.8172 0.5030 1.0220 0.106 Uiso 1 1 calc R U . . .
H22B H 0.7188 0.5545 0.9678 0.106 Uiso 1 1 calc R U . . .
H22C H 0.8499 0.5998 0.9965 0.106 Uiso 1 1 calc R U . . .
C23 C 0.6008(4) 0.0195(3) 0.7576(3) 0.0479(12) Uani 1 1 d . . . . .
C24 C 0.6114(6) -0.0356(4) 0.6836(3) 0.0752(17) Uani 1 1 d . . . . .
H24A H 0.6173 0.0027 0.6392 0.113 Uiso 1 1 calc R U . . .
H24B H 0.5341 -0.0723 0.6787 0.113 Uiso 1 1 calc R U . . .
H24C H 0.6893 -0.0720 0.6862 0.113 Uiso 1 1 calc R U . . .
C25 C 0.5863(5) -0.0397(4) 0.8275(3) 0.0727(16) Uani 1 1 d . . . . .
H25A H 0.6671 -0.0721 0.8352 0.109 Uiso 1 1 calc R U . . .
H25B H 0.5144 -0.0802 0.8190 0.109 Uiso 1 1 calc R U . . .
H25C H 0.5681 -0.0047 0.8728 0.109 Uiso 1 1 calc R U . . .
C26 C 0.4906(5) 0.0872(4) 0.7515(4) 0.098(2) Uani 1 1 d . . . . .
H26A H 0.4853 0.1200 0.7992 0.147 Uiso 1 1 calc R U . . .
H26B H 0.4076 0.0578 0.7422 0.147 Uiso 1 1 calc R U . . .
H26C H 0.5091 0.1267 0.7092 0.147 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
Br1 C5 1.902(4) . ?
S1 O5 1.480(3) . ?
S1 N2 1.679(3) . ?
S1 C23 1.849(5) . ?
O1 C17 1.348(5) . ?
O1 C20 1.453(5) . ?
O2 C19 1.361(5) . ?
O2 C20 1.441(5) . ?
O3 C19 1.215(5) . ?
O4 C4 1.210(5) . ?
N1 C4 1.368(5) . ?
N1 C3 1.400(5) . ?
N1 C9 1.459(5) . ?
N2 C1 1.474(5) . ?
C1 C2 1.516(5) . ?
C1 C4 1.546(6) . ?
C1 C16 1.555(6) . ?
C2 C5 1.373(5) . ?
C2 C3 1.395(5) . ?
C3 C8 1.395(6) . ?
C5 C6 1.380(6) . ?
C6 C7 1.374(7) . ?
C7 C8 1.377(6) . ?
C9 C10 1.505(6) . ?
C10 C11 1.377(6) . ?
C10 C15 1.380(6) . ?
C11 C12 1.399(7) . ?
C12 C13 1.368(8) . ?
C13 C14 1.373(8) . ?
C14 C15 1.375(7) . ?
C16 C17 1.506(6) . ?
C17 C18 1.333(6) . ?
C18 C19 1.441(6) . ?
C20 C21 1.498(7) . ?
C20 C22 1.514(7) . ?
C23 C25 1.506(7) . ?
C23 C26 1.515(6) . ?
C23 C24 1.526(7) . ?

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
O5 S1 N2 109.79(19) . . ?
O5 S1 C23 104.8(2) . . ?
N2 S1 C23 99.91(19) . . ?
C17 O1 C20 116.1(3) . . ?
C19 O2 C20 118.5(3) . . ?
C4 N1 C3 111.2(3) . . ?
C4 N1 C9 124.5(4) . . ?
C3 N1 C9 124.3(3) . . ?
C1 N2 S1 115.3(3) . . ?
N2 C1 C2 117.3(3) . . ?
N2 C1 C4 109.6(3) . . ?
C2 C1 C4 102.2(4) . . ?
N2 C1 C16 106.7(3) . . ?
C2 C1 C16 112.1(3) . . ?
C4 C1 C16 108.8(3) . . ?
C5 C2 C3 118.1(4) . . ?
C5 C2 C1 133.8(4) . . ?
C3 C2 C1 107.9(4) . . ?
C8 C3 C2 122.3(4) . . ?
C8 C3 N1 127.2(4) . . ?
C2 C3 N1 110.5(4) . . ?
O4 C4 N1 125.9(4) . . ?
O4 C4 C1 126.2(4) . . ?
N1 C4 C1 107.8(4) . . ?
C2 C5 C6 120.8(4) . . ?
C2 C5 Br1 119.8(3) . . ?
C6 C5 Br1 119.4(4) . . ?
C7 C6 C5 119.9(5) . . ?
C6 C7 C8 121.8(5) . . ?
C7 C8 C3 117.0(4) . . ?
N1 C9 C10 113.1(3) . . ?
C11 C10 C15 118.5(5) . . ?
C11 C10 C9 120.1(4) . . ?
C15 C10 C9 121.3(4) . . ?
C10 C11 C12 120.3(5) . . ?
C13 C12 C11 119.9(5) . . ?
C12 C13 C14 120.0(5) . . ?
C13 C14 C15 119.9(6) . . ?
C14 C15 C10 121.3(5) . . ?
C17 C16 C1 112.2(3) . . ?
C18 C17 O1 121.0(4) . . ?
C18 C17 C16 125.3(4) . . ?
O1 C17 C16 113.4(4) . . ?
C17 C18 C19 120.7(4) . . ?
O3 C19 O2 117.7(4) . . ?
O3 C19 C18 126.6(4) . . ?
O2 C19 C18 115.5(4) . . ?
O2 C20 O1 109.7(3) . . ?
O2 C20 C21 106.3(4) . . ?
O1 C20 C21 107.5(4) . . ?
O2 C20 C22 109.7(4) . . ?
O1 C20 C22 109.1(4) . . ?
C21 C20 C22 114.5(4) . . ?
C25 C23 C26 112.9(5) . . ?
C25 C23 C24 110.1(4) . . ?
C26 C23 C24 111.4(4) . . ?
C25 C23 S1 110.0(3) . . ?
C26 C23 S1 108.0(3) . . ?
C24 C23 S1 104.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 S1 N2 C1 95.6(3) . . . . ?
C23 S1 N2 C1 -154.5(3) . . . . ?
S1 N2 C1 C2 -52.4(5) . . . . ?
S1 N2 C1 C4 63.5(4) . . . . ?
S1 N2 C1 C16 -179.0(3) . . . . ?
N2 C1 C2 C5 -59.4(6) . . . . ?
C4 C1 C2 C5 -179.2(4) . . . . ?
C16 C1 C2 C5 64.4(6) . . . . ?
N2 C1 C2 C3 125.3(4) . . . . ?
C4 C1 C2 C3 5.5(4) . . . . ?
C16 C1 C2 C3 -110.9(4) . . . . ?
C5 C2 C3 C8 -0.7(6) . . . . ?
C1 C2 C3 C8 175.4(4) . . . . ?
C5 C2 C3 N1 -179.3(3) . . . . ?
C1 C2 C3 N1 -3.2(4) . . . . ?
C4 N1 C3 C8 -179.4(4) . . . . ?
C9 N1 C3 C8 -1.4(6) . . . . ?
C4 N1 C3 C2 -1.0(4) . . . . ?
C9 N1 C3 C2 177.1(4) . . . . ?
C3 N1 C4 O4 -178.5(4) . . . . ?
C9 N1 C4 O4 3.4(7) . . . . ?
C3 N1 C4 C1 4.6(4) . . . . ?
C9 N1 C4 C1 -173.5(4) . . . . ?
N2 C1 C4 O4 52.0(6) . . . . ?
C2 C1 C4 O4 177.1(4) . . . . ?
C16 C1 C4 O4 -64.2(5) . . . . ?
N2 C1 C4 N1 -131.1(3) . . . . ?
C2 C1 C4 N1 -6.0(4) . . . . ?
C16 C1 C4 N1 112.7(4) . . . . ?
C3 C2 C5 C6 -0.3(6) . . . . ?
C1 C2 C5 C6 -175.2(4) . . . . ?
C3 C2 C5 Br1 177.7(3) . . . . ?
C1 C2 C5 Br1 2.8(6) . . . . ?
C2 C5 C6 C7 1.4(7) . . . . ?
Br1 C5 C6 C7 -176.6(3) . . . . ?
C5 C6 C7 C8 -1.6(7) . . . . ?
C6 C7 C8 C3 0.6(7) . . . . ?
C2 C3 C8 C7 0.6(6) . . . . ?
N1 C3 C8 C7 178.9(4) . . . . ?
C4 N1 C9 C10 -111.3(5) . . . . ?
C3 N1 C9 C10 70.9(5) . . . . ?
N1 C9 C10 C11 -133.5(4) . . . . ?
N1 C9 C10 C15 50.5(6) . . . . ?
C15 C10 C11 C12 2.6(7) . . . . ?
C9 C10 C11 C12 -173.5(4) . . . . ?
C10 C11 C12 C13 -2.1(8) . . . . ?
C11 C12 C13 C14 0.1(8) . . . . ?
C12 C13 C14 C15 1.3(9) . . . . ?
C13 C14 C15 C10 -0.8(8) . . . . ?
C11 C10 C15 C14 -1.2(7) . . . . ?
C9 C10 C15 C14 174.9(5) . . . . ?
N2 C1 C16 C17 171.3(3) . . . . ?
C2 C1 C16 C17 41.7(5) . . . . ?
C4 C1 C16 C17 -70.6(4) . . . . ?
C20 O1 C17 C18 -17.8(6) . . . . ?
C20 O1 C17 C16 166.8(4) . . . . ?
C1 C16 C17 C18 -97.0(5) . . . . ?
C1 C16 C17 O1 78.1(5) . . . . ?
O1 C17 C18 C19 -11.1(6) . . . . ?
C16 C17 C18 C19 163.8(4) . . . . ?
C20 O2 C19 O3 -165.5(4) . . . . ?
C20 O2 C19 C18 20.4(5) . . . . ?
C17 C18 C19 O3 -163.5(4) . . . . ?
C17 C18 C19 O2 9.9(6) . . . . ?
C19 O2 C20 O1 -46.6(5) . . . . ?
C19 O2 C20 C21 -162.4(4) . . . . ?
C19 O2 C20 C22 73.3(5) . . . . ?
C17 O1 C20 O2 44.7(5) . . . . ?
C17 O1 C20 C21 159.8(4) . . . . ?
C17 O1 C20 C22 -75.5(5) . . . . ?
O5 S1 C23 C25 45.2(4) . . . . ?
N2 S1 C23 C25 -68.5(4) . . . . ?
O5 S1 C23 C26 168.8(4) . . . . ?
N2 S1 C23 C26 55.1(4) . . . . ?
O5 S1 C23 C24 -72.7(4) . . . . ?
N2 S1 C23 C24 173.6(3) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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. 
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#######################################################################

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1573541'
_audit_update_record             
;
2017-09-09 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H25 N O4 S'
_chemical_formula_weight         351.45

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

_space_group_crystal_system      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                   10.551(7)
_cell_length_b                   11.366(8)
_cell_length_c                   16.422(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1969(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    928
_cell_measurement_theta_min      2.4805
_cell_measurement_theta_max      15.8903

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11219
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3469
_reflns_number_gt                1814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.974

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0484P)²] 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 541 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3469
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_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 0.54631(16) 0.65646(14) 0.91770(8) 0.0760(5) Uani 1 1 d . . . . .
O1 O 0.9302(4) 0.1663(3) 0.9604(3) 0.0840(12) Uani 1 1 d . . . . .
O2 O 1.0224(3) 0.3348(3) 0.9890(2) 0.0705(10) Uani 1 1 d . . . . .
O3 O 0.9123(3) 0.4857(3) 1.0570(2) 0.0691(11) Uani 1 1 d . . . . .
O4 O 0.4228(5) 0.7133(4) 0.9336(3) 0.1274(19) Uani 1 1 d . . . . .
N1 N 0.5784(3) 0.5531(3) 0.9850(2) 0.0518(11) Uani 1 1 d . . . . .
H1 H 0.5577 0.4810 0.9763 0.062 Uiso 1 1 calc R U . . .
C1 C 0.5599(5) 0.6465(5) 1.1239(3) 0.0538(13) Uani 1 1 d . . . . .
C2 C 0.4341(6) 0.6220(6) 1.1315(4) 0.084(2) Uani 1 1 d . . . . .
H2 H 0.3945 0.5739 1.0934 0.101 Uiso 1 1 calc R U . . .
C3 C 0.3652(7) 0.6675(8) 1.1950(5) 0.118(3) Uani 1 1 d . . . . .
H3 H 0.2794 0.6499 1.1993 0.142 Uiso 1 1 calc R U . . .
C4 C 0.4189(11) 0.7362(8) 1.2504(5) 0.119(3) Uani 1 1 d . . . . .
H4 H 0.3713 0.7631 1.2942 0.143 Uiso 1 1 calc R U . . .
C5 C 0.5416(12) 0.7675(7) 1.2438(4) 0.108(3) Uani 1 1 d . . . . .
H5 H 0.5778 0.8192 1.2810 0.130 Uiso 1 1 calc R U . . .
C6 C 0.6145(6) 0.7203(6) 1.1792(4) 0.082(2) Uani 1 1 d . . . . .
H6 H 0.6998 0.7397 1.1745 0.099 Uiso 1 1 calc R U . . .
C7 C 0.6431(4) 0.5876(4) 1.0601(3) 0.0480(13) Uani 1 1 d . . . . .
H7 H 0.7125 0.6412 1.0461 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7000(4) 0.4753(4) 1.0988(3) 0.0569(14) Uani 1 1 d . . . . .
H8A H 0.7307 0.4947 1.1528 0.068 Uiso 1 1 calc R U . . .
H8B H 0.6329 0.4177 1.1050 0.068 Uiso 1 1 calc R U . . .
C9 C 0.8047(5) 0.4209(5) 1.0523(3) 0.0551(14) Uani 1 1 d . . . . .
C10 C 0.8029(5) 0.3191(5) 1.0133(3) 0.0592(14) Uani 1 1 d . . . . .
H10 H 0.7261 0.2806 1.0053 0.071 Uiso 1 1 calc R U . . .
C11 C 0.9175(5) 0.2672(6) 0.9833(3) 0.0631(15) Uani 1 1 d . . . . .
C12 C 1.0080(5) 0.4608(5) 0.9965(4) 0.0686(16) Uani 1 1 d . . . . .
C13 C 1.1311(5) 0.5070(6) 1.0306(5) 0.108(2) Uani 1 1 d . . . . .
H13A H 1.1525 0.4641 1.0791 0.161 Uiso 1 1 calc R U . . .
H13B H 1.1220 0.5889 1.0435 0.161 Uiso 1 1 calc R U . . .
H13C H 1.1972 0.4973 0.9910 0.161 Uiso 1 1 calc R U . . .
C14 C 0.9695(6) 0.5123(5) 0.9167(4) 0.097(2) Uani 1 1 d . . . . .
H14A H 1.0340 0.4968 0.8769 0.145 Uiso 1 1 calc R U . . .
H14B H 0.9586 0.5958 0.9225 0.145 Uiso 1 1 calc R U . . .
H14C H 0.8911 0.4776 0.8994 0.145 Uiso 1 1 calc R U . . .
C15 C 0.5175(6) 0.5619(5) 0.8294(3) 0.0694(17) Uani 1 1 d . . . . .
C16 C 0.4011(6) 0.4891(7) 0.8430(4) 0.109(2) Uani 1 1 d . . . . .
H16A H 0.4178 0.4312 0.8842 0.164 Uiso 1 1 calc R U . . .
H16B H 0.3782 0.4504 0.7931 0.164 Uiso 1 1 calc R U . . .
H16C H 0.3328 0.5389 0.8603 0.164 Uiso 1 1 calc R U . . .
C17 C 0.4956(8) 0.6481(7) 0.7590(4) 0.116(2) Uani 1 1 d . . . . .
H17A H 0.4261 0.6993 0.7720 0.174 Uiso 1 1 calc R U . . .
H17B H 0.4762 0.6049 0.7103 0.174 Uiso 1 1 calc R U . . .
H17C H 0.5707 0.6941 0.7505 0.174 Uiso 1 1 calc R U . . .
C18 C 0.6339(6) 0.4860(7) 0.8135(4) 0.109(3) Uani 1 1 d . . . . .
H18A H 0.7081 0.5349 0.8124 0.163 Uiso 1 1 calc R U . . .
H18B H 0.6248 0.4466 0.7622 0.163 Uiso 1 1 calc R U . . .
H18C H 0.6422 0.4287 0.8561 0.163 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 O4 1.478(5) . ?
S1 N1 1.649(4) . ?
S1 C15 1.831(6) . ?
O1 C11 1.214(6) . ?
O2 C11 1.350(6) . ?
O2 C12 1.446(6) . ?
O3 C9 1.355(6) . ?
O3 C12 1.445(6) . ?
N1 C7 1.463(5) . ?
N1 H1 0.8600 . ?
C1 C2 1.362(7) . ?
C1 C6 1.365(7) . ?
C1 C7 1.521(6) . ?
C2 C3 1.372(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.325(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.347(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.547(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.479(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.323(7) . ?
C10 C11 1.433(7) . ?
C10 H10 0.9300 . ?
C12 C14 1.491(7) . ?
C12 C13 1.509(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.497(8) . ?
C15 C18 1.524(8) . ?
C15 C17 1.533(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O4 S1 N1 112.0(3) . . ?
O4 S1 C15 104.5(3) . . ?
N1 S1 C15 98.5(2) . . ?
C11 O2 C12 118.9(4) . . ?
C9 O3 C12 116.1(4) . . ?
C7 N1 S1 118.0(3) . . ?
C7 N1 H1 121.0 . . ?
S1 N1 H1 121.0 . . ?
C2 C1 C6 118.4(5) . . ?
C2 C1 C7 122.4(5) . . ?
C6 C1 C7 119.0(5) . . ?
C1 C2 C3 120.6(6) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.1(8) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.8(8) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.8(8) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 120.2(7) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C1 115.4(4) . . ?
N1 C7 C8 107.8(4) . . ?
C1 C7 C8 107.7(4) . . ?
N1 C7 H7 108.6 . . ?
C1 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
C9 C8 C7 115.0(4) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 O3 121.0(5) . . ?
C10 C9 C8 127.2(5) . . ?
O3 C9 C8 111.7(5) . . ?
C9 C10 C11 121.0(5) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
O1 C11 O2 117.9(5) . . ?
O1 C11 C10 126.0(5) . . ?
O2 C11 C10 115.7(5) . . ?
O3 C12 O2 109.0(4) . . ?
O3 C12 C14 109.7(4) . . ?
O2 C12 C14 110.1(5) . . ?
O3 C12 C13 106.1(5) . . ?
O2 C12 C13 106.6(5) . . ?
C14 C12 C13 115.1(6) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C18 111.9(6) . . ?
C16 C15 C17 110.0(6) . . ?
C18 C15 C17 110.8(5) . . ?
C16 C15 S1 110.1(4) . . ?
C18 C15 S1 109.5(4) . . ?
C17 C15 S1 104.3(4) . . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O4 S1 N1 C7 -87.8(4) . . . . ?
C15 S1 N1 C7 162.7(3) . . . . ?
C6 C1 C2 C3 -2.1(10) . . . . ?
C7 C1 C2 C3 173.2(6) . . . . ?
C1 C2 C3 C4 0.0(12) . . . . ?
C2 C3 C4 C5 3.0(14) . . . . ?
C3 C4 C5 C6 -3.6(13) . . . . ?
C2 C1 C6 C5 1.4(9) . . . . ?
C7 C1 C6 C5 -174.0(5) . . . . ?
C4 C5 C6 C1 1.4(11) . . . . ?
S1 N1 C7 C1 77.6(5) . . . . ?
S1 N1 C7 C8 -162.1(3) . . . . ?
C2 C1 C7 N1 29.8(7) . . . . ?
C6 C1 C7 N1 -154.9(5) . . . . ?
C2 C1 C7 C8 -90.6(6) . . . . ?
C6 C1 C7 C8 84.7(6) . . . . ?
N1 C7 C8 C9 67.7(5) . . . . ?
C1 C7 C8 C9 -167.2(4) . . . . ?
C12 O3 C9 C10 20.5(7) . . . . ?
C12 O3 C9 C8 -162.8(4) . . . . ?
C7 C8 C9 C10 -111.3(6) . . . . ?
C7 C8 C9 O3 72.3(5) . . . . ?
O3 C9 C10 C11 7.6(8) . . . . ?
C8 C9 C10 C11 -168.6(5) . . . . ?
C12 O2 C11 O1 165.0(5) . . . . ?
C12 O2 C11 C10 -21.3(7) . . . . ?
C9 C10 C11 O1 165.7(6) . . . . ?
C9 C10 C11 O2 -7.4(8) . . . . ?
C9 O3 C12 O2 -45.1(6) . . . . ?
C9 O3 C12 C14 75.5(6) . . . . ?
C9 O3 C12 C13 -159.6(5) . . . . ?
C11 O2 C12 O3 46.4(6) . . . . ?
C11 O2 C12 C14 -73.9(6) . . . . ?
C11 O2 C12 C13 160.6(5) . . . . ?
O4 S1 C15 C16 -49.3(5) . . . . ?
N1 S1 C15 C16 66.1(5) . . . . ?
O4 S1 C15 C18 -172.7(5) . . . . ?
N1 S1 C15 C18 -57.3(5) . . . . ?
O4 S1 C15 C17 68.7(5) . . . . ?
N1 S1 C15 C17 -175.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.39 3.077(6) 137.6 4_457
C8 H8B O1 0.97 2.58 3.412(6) 144.3 4_457
C10 H10 O2 0.93 2.52 3.438(6) 169.3 4_457

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036

_shelxl_version_number           2014-3

