# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_2_6_CL_0m
_database_code_depnum_ccdc_archive 'CCDC 1565464'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 Cl2 N O2 S'
_chemical_formula_sum            'C10 H9 Cl2 N O2 S'
_chemical_formula_weight         278.14

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'
Cl Cl 0.1484 0.1585 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.9790(7)
_cell_length_b                   8.4645(9)
_cell_length_c                   19.895(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1175.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7162
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      33.54

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.712
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_details   sadabs,(bruker,2016)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7473
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2058
_reflns_number_gt                2017
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.1885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2058
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Cl1 Cl 0.18231(15) 1.32834(8) 0.11659(4) 0.0675(3) Uani 1 1 d . . . . .
Cl2 Cl 0.20724(11) 0.71622(8) 0.03034(3) 0.0495(2) Uani 1 1 d . . . . .
S1 S -0.04009(9) 0.86037(8) 0.16429(3) 0.0432(2) Uani 1 1 d . . . . .
O1 O 0.5614(4) 0.6270(3) 0.20685(11) 0.0666(7) Uani 1 1 d . . . . .
O2 O 0.4058(3) 0.6133(2) 0.30457(8) 0.0401(4) Uani 1 1 d . . . . .
H2 H 0.4742 0.5358 0.3107 0.060 Uiso 1 1 calc R U . . .
N1 N 0.3468(3) 0.8825(2) 0.16663(9) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.1816(3) 0.9732(3) 0.14341(11) 0.0316(5) Uani 1 1 d . . . . .
H1 H 0.1782 1.0701 0.1703 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2872(4) 0.7924(3) 0.22574(10) 0.0327(5) Uani 1 1 d . . . . .
H2A H 0.2711 0.8651 0.2637 0.039 Uiso 1 1 calc R U . . .
C3 C 0.0932(4) 0.7142(3) 0.21023(14) 0.0448(6) Uani 1 1 d . . . . .
H3A H 0.0273 0.6860 0.2514 0.054 Uiso 1 1 calc R U . . .
H3B H 0.1109 0.6196 0.1834 0.054 Uiso 1 1 calc R U . . .
C4 C 0.4353(4) 0.6691(3) 0.24421(11) 0.0355(5) Uani 1 1 d . . . . .
C5 C 0.1902(4) 1.0239(3) 0.07091(11) 0.0331(5) Uani 1 1 d . . . . .
C6 C 0.1853(4) 1.1842(3) 0.05407(13) 0.0427(6) Uani 1 1 d . . . . .
C7 C 0.1844(5) 1.2364(4) -0.01208(16) 0.0592(8) Uani 1 1 d . . . . .
H7 H 0.1804 1.3438 -0.0217 0.071 Uiso 1 1 calc R U . . .
C8 C 0.1895(5) 1.1280(4) -0.06285(15) 0.0639(9) Uani 1 1 d . . . . .
H8 H 0.1878 1.1624 -0.1072 0.077 Uiso 1 1 calc R U . . .
C9 C 0.1970(5) 0.9693(4) -0.04943(13) 0.0530(7) Uani 1 1 d . . . . .
H9 H 0.2013 0.8962 -0.0843 0.064 Uiso 1 1 calc R U . . .
C10 C 0.1982(4) 0.9196(3) 0.01666(11) 0.0368(5) Uani 1 1 d . . . . .
H1N H 0.378(4) 0.818(3) 0.1377(14) 0.029(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.742(3) . ?
Cl2 C10 1.744(3) . ?
S1 C3 1.798(3) . ?
S1 C1 1.865(3) . ?
O1 C4 1.206(3) . ?
O2 C4 1.307(3) . ?
O2 H2 0.8200 . ?
N1 C1 1.460(3) . ?
N1 C2 1.462(3) . ?
N1 H1N 0.82(3) . ?
C1 C5 1.506(3) . ?
C1 H1 0.9800 . ?
C2 C4 1.514(3) . ?
C2 C3 1.538(4) . ?
C2 H2A 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C10 1.395(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.388(4) . ?
C7 C8 1.365(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?

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
C3 S1 C1 92.08(11) . . ?
C4 O2 H2 109.5 . . ?
C1 N1 C2 107.70(18) . . ?
C1 N1 H1N 109.5(18) . . ?
C2 N1 H1N 107.0(18) . . ?
N1 C1 C5 114.9(2) . . ?
N1 C1 S1 108.37(15) . . ?
C5 C1 S1 113.08(17) . . ?
N1 C1 H1 106.6 . . ?
C5 C1 H1 106.6 . . ?
S1 C1 H1 106.6 . . ?
N1 C2 C4 111.11(19) . . ?
N1 C2 C3 108.28(19) . . ?
C4 C2 C3 110.7(2) . . ?
N1 C2 H2A 108.9 . . ?
C4 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C2 C3 S1 105.14(17) . . ?
C2 C3 H3A 110.7 . . ?
S1 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
S1 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
O1 C4 O2 125.1(2) . . ?
O1 C4 C2 123.5(2) . . ?
O2 C4 C2 111.4(2) . . ?
C10 C5 C6 115.4(2) . . ?
C10 C5 C1 124.2(2) . . ?
C6 C5 C1 120.3(2) . . ?
C7 C6 C5 122.4(3) . . ?
C7 C6 Cl1 117.0(2) . . ?
C5 C6 Cl1 120.6(2) . . ?
C8 C7 C6 119.2(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C5 123.0(2) . . ?
C9 C10 Cl2 116.7(2) . . ?
C5 C10 Cl2 120.35(18) . . ?

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
C2 N1 C1 C5 -158.19(19) . . . . ?
C2 N1 C1 S1 -30.6(2) . . . . ?
C3 S1 C1 N1 6.19(17) . . . . ?
C3 S1 C1 C5 134.84(18) . . . . ?
C1 N1 C2 C4 167.83(19) . . . . ?
C1 N1 C2 C3 46.1(2) . . . . ?
N1 C2 C3 S1 -40.0(2) . . . . ?
C4 C2 C3 S1 -161.97(16) . . . . ?
C1 S1 C3 C2 18.42(17) . . . . ?
N1 C2 C4 O1 -15.7(3) . . . . ?
C3 C2 C4 O1 104.6(3) . . . . ?
N1 C2 C4 O2 165.6(2) . . . . ?
C3 C2 C4 O2 -74.1(3) . . . . ?
N1 C1 C5 C10 61.6(3) . . . . ?
S1 C1 C5 C10 -63.6(3) . . . . ?
N1 C1 C5 C6 -120.1(3) . . . . ?
S1 C1 C5 C6 114.7(2) . . . . ?
C10 C5 C6 C7 1.3(4) . . . . ?
C1 C5 C6 C7 -177.1(3) . . . . ?
C10 C5 C6 Cl1 -178.1(2) . . . . ?
C1 C5 C6 Cl1 3.5(4) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
Cl1 C6 C7 C8 179.1(3) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C5 0.6(5) . . . . ?
C8 C9 C10 Cl2 179.8(3) . . . . ?
C6 C5 C10 C9 -1.4(4) . . . . ?
C1 C5 C10 C9 176.9(3) . . . . ?
C6 C5 C10 Cl2 179.4(2) . . . . ?
C1 C5 C10 Cl2 -2.3(4) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_BJ20BOC_BSC_0m
_database_code_depnum_ccdc_archive 'CCDC 1565479'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N O5 S'
_chemical_formula_sum            'C16 H21 N O5 S'
_chemical_formula_weight         339.40

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   31.2006(17)
_cell_length_b                   10.1101(5)
_cell_length_c                   5.9607(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.505(4)
_cell_angle_gamma                90
_cell_volume                     1876.73(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5554
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      24.92

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   SADABS,(BRUKER,2016)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13496
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.118
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3287
_reflns_number_gt                3023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+0.8506P] 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 1254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_chemical_absolute_configuration SYN
_refine_ls_number_reflns         3287
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.007
_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 0.62412(4) 0.69597(11) 0.0381(2) 0.0568(4) Uani 1 1 d . . . . .
O1 O 0.53343(9) 0.9461(5) -0.2410(5) 0.0619(10) Uani 1 1 d . . . . .
H1 H 0.5084 0.9402 -0.2071 0.093 Uiso 1 1 calc R U . . .
O2 O 0.54706(9) 0.9332(4) 0.1279(5) 0.0530(8) Uani 1 1 d . . . . .
O3 O 0.64612(10) 1.0627(3) 0.4191(5) 0.0493(8) Uani 1 1 d . . . . .
O4 O 0.60917(8) 1.1566(3) 0.1185(5) 0.0413(7) Uani 1 1 d . . . . .
O5 O 0.70009(11) 0.6696(3) 0.4545(6) 0.0642(10) Uani 1 1 d . . . . .
N1 N 0.63395(9) 0.9528(3) 0.0903(5) 0.0346(7) Uani 1 1 d . . . . .
C1 C 0.65286(13) 0.8319(4) 0.1841(7) 0.0399(9) Uani 1 1 d . . . . .
H1A H 0.6474 0.8276 0.3441 0.048 Uiso 1 1 calc R U . . .
C2 C 0.60566(12) 0.9351(4) -0.1140(6) 0.0376(9) Uani 1 1 d . . . . .
H2 H 0.6114 1.0041 -0.2237 0.045 Uiso 1 1 calc R U . . .
C3 C 0.61709(15) 0.8003(5) -0.2062(8) 0.0514(11) Uani 1 1 d . . . . .
H3A H 0.6433 0.8050 -0.2851 0.062 Uiso 1 1 calc R U . . .
H3B H 0.5942 0.7673 -0.3085 0.062 Uiso 1 1 calc R U . . .
C4 C 0.55879(13) 0.9389(4) -0.0606(7) 0.0408(9) Uani 1 1 d . . . . .
C5 C 0.63044(12) 1.0584(4) 0.2280(7) 0.0369(9) Uani 1 1 d . . . . .
C6 C 0.59310(14) 1.2736(4) 0.2380(8) 0.0472(11) Uani 1 1 d . . . . .
C7 C 0.5700(2) 1.3483(6) 0.0506(10) 0.0771(17) Uani 1 1 d . . . . .
H7A H 0.5900 1.3733 -0.0580 0.116 Uiso 1 1 calc R U . . .
H7B H 0.5572 1.4262 0.1095 0.116 Uiso 1 1 calc R U . . .
H7C H 0.5480 1.2932 -0.0201 0.116 Uiso 1 1 calc R U . . .
C8 C 0.62954(19) 1.3556(6) 0.3446(11) 0.0754(17) Uani 1 1 d . . . . .
H8A H 0.6488 1.3799 0.2320 0.113 Uiso 1 1 calc R U . . .
H8B H 0.6448 1.3047 0.4598 0.113 Uiso 1 1 calc R U . . .
H8C H 0.6181 1.4340 0.4094 0.113 Uiso 1 1 calc R U . . .
C9 C 0.56249(19) 1.2278(6) 0.4097(10) 0.0796(18) Uani 1 1 d . . . . .
H9A H 0.5441 1.2997 0.4462 0.119 Uiso 1 1 calc R U . . .
H9B H 0.5786 1.1989 0.5431 0.119 Uiso 1 1 calc R U . . .
H9C H 0.5454 1.1559 0.3486 0.119 Uiso 1 1 calc R U . . .
C10 C 0.70057(12) 0.8194(4) 0.1594(6) 0.0373(9) Uani 1 1 d . . . . .
C11 C 0.72361(14) 0.7315(4) 0.3011(8) 0.0466(10) Uani 1 1 d . . . . .
C12 C 0.76714(14) 0.7120(5) 0.2774(9) 0.0562(13) Uani 1 1 d . . . . .
H12 H 0.7826 0.6544 0.3733 0.067 Uiso 1 1 calc R U . . .
C13 C 0.78719(15) 0.7777(6) 0.1128(10) 0.0610(14) Uani 1 1 d . . . . .
H13 H 0.8162 0.7628 0.0955 0.073 Uiso 1 1 calc R U . . .
C14 C 0.76490(14) 0.8660(5) -0.0285(9) 0.0554(12) Uani 1 1 d . . . . .
H14 H 0.7789 0.9108 -0.1391 0.067 Uiso 1 1 calc R U . . .
C15 C 0.72162(13) 0.8870(4) -0.0037(8) 0.0435(10) Uani 1 1 d . . . . .
H15 H 0.7065 0.9468 -0.0971 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7215(2) 0.5868(6) 0.6182(9) 0.0770(17) Uani 1 1 d . . . . .
H16A H 0.7347 0.5143 0.5447 0.115 Uiso 1 1 calc R U . . .
H16B H 0.7012 0.5533 0.7183 0.115 Uiso 1 1 calc R U . . .
H16C H 0.7432 0.6370 0.7022 0.115 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 C3 1.801(5) . ?
S1 C1 1.831(5) . ?
O1 C4 1.298(5) . ?
O1 H1 0.8200 . ?
O2 C4 1.204(5) . ?
O3 C5 1.213(5) . ?
O4 C5 1.341(5) . ?
O4 C6 1.484(5) . ?
O5 C11 1.360(6) . ?
O5 C16 1.421(6) . ?
N1 C5 1.355(5) . ?
N1 C1 1.454(5) . ?
N1 C2 1.471(5) . ?
C1 C10 1.510(5) . ?
C1 H1A 0.9800 . ?
C2 C4 1.516(5) . ?
C2 C3 1.520(6) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C7 1.496(7) . ?
C6 C8 1.515(7) . ?
C6 C9 1.514(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.386(6) . ?
C10 C11 1.395(6) . ?
C11 C12 1.388(6) . ?
C12 C13 1.367(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C3 S1 C1 88.7(2) . . ?
C4 O1 H1 109.5 . . ?
C5 O4 C6 121.9(3) . . ?
C11 O5 C16 118.8(4) . . ?
C5 N1 C1 118.4(3) . . ?
C5 N1 C2 122.0(3) . . ?
C1 N1 C2 115.2(3) . . ?
N1 C1 C10 114.3(3) . . ?
N1 C1 S1 105.8(3) . . ?
C10 C1 S1 110.4(3) . . ?
N1 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
S1 C1 H1A 108.7 . . ?
N1 C2 C4 111.1(3) . . ?
N1 C2 C3 105.4(3) . . ?
C4 C2 C3 110.4(4) . . ?
N1 C2 H2 109.9 . . ?
C4 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C2 C3 S1 104.6(3) . . ?
C2 C3 H3A 110.8 . . ?
S1 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
S1 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
O2 C4 O1 124.8(4) . . ?
O2 C4 C2 123.2(3) . . ?
O1 C4 C2 112.0(3) . . ?
O3 C5 N1 123.7(4) . . ?
O3 C5 O4 126.1(4) . . ?
N1 C5 O4 110.1(3) . . ?
C7 C6 O4 101.8(4) . . ?
C7 C6 C8 110.6(5) . . ?
O4 C6 C8 111.7(4) . . ?
C7 C6 C9 111.4(5) . . ?
O4 C6 C9 109.0(4) . . ?
C8 C6 C9 111.8(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.3(4) . . ?
C15 C10 C1 122.7(4) . . ?
C11 C10 C1 117.9(4) . . ?
O5 C11 C12 125.1(4) . . ?
O5 C11 C10 114.9(4) . . ?
C12 C11 C10 120.0(4) . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.4(5) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 120.5(4) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C5 N1 C1 C10 -93.3(4) . . . . ?
C2 N1 C1 C10 109.8(4) . . . . ?
C5 N1 C1 S1 145.1(3) . . . . ?
C2 N1 C1 S1 -11.9(4) . . . . ?
C3 S1 C1 N1 31.1(3) . . . . ?
C3 S1 C1 C10 -93.1(3) . . . . ?
C5 N1 C2 C4 -55.0(5) . . . . ?
C1 N1 C2 C4 101.0(4) . . . . ?
C5 N1 C2 C3 -174.7(3) . . . . ?
C1 N1 C2 C3 -18.7(4) . . . . ?
N1 C2 C3 S1 41.1(4) . . . . ?
C4 C2 C3 S1 -79.1(3) . . . . ?
C1 S1 C3 C2 -41.9(3) . . . . ?
N1 C2 C4 O2 -12.3(6) . . . . ?
C3 C2 C4 O2 104.4(5) . . . . ?
N1 C2 C4 O1 169.0(4) . . . . ?
C3 C2 C4 O1 -74.3(5) . . . . ?
C1 N1 C5 O3 7.9(5) . . . . ?
C2 N1 C5 O3 163.2(4) . . . . ?
C1 N1 C5 O4 -174.8(3) . . . . ?
C2 N1 C5 O4 -19.6(5) . . . . ?
C6 O4 C5 O3 -15.1(6) . . . . ?
C6 O4 C5 N1 167.8(3) . . . . ?
C5 O4 C6 C7 -176.8(4) . . . . ?
C5 O4 C6 C8 65.1(5) . . . . ?
C5 O4 C6 C9 -59.0(5) . . . . ?
N1 C1 C10 C15 -22.7(6) . . . . ?
S1 C1 C10 C15 96.4(4) . . . . ?
N1 C1 C10 C11 160.2(4) . . . . ?
S1 C1 C10 C11 -80.7(4) . . . . ?
C16 O5 C11 C12 5.9(7) . . . . ?
C16 O5 C11 C10 -174.7(4) . . . . ?
C15 C10 C11 O5 -179.6(4) . . . . ?
C1 C10 C11 O5 -2.5(5) . . . . ?
C15 C10 C11 C12 -0.3(6) . . . . ?
C1 C10 C11 C12 176.9(4) . . . . ?
O5 C11 C12 C13 178.4(4) . . . . ?
C10 C11 C12 C13 -1.0(7) . . . . ?
C11 C12 C13 C14 1.4(7) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C11 C10 C15 C14 1.1(6) . . . . ?
C1 C10 C15 C14 -176.0(4) . . . . ?
C13 C14 C15 C10 -0.6(7) . . . . ?

_refine_diff_density_max         0.663
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_mo_BJ16B_0m
_database_code_depnum_ccdc_archive 'CCDC 1565476'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O6 S'
_chemical_formula_sum            'C15 H18 N2 O6 S'
_chemical_formula_weight         354.37

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.0776(4)
_cell_length_b                   6.3731(3)
_cell_length_c                   13.2240(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.4180(10)
_cell_angle_gamma                90
_cell_volume                     849.30(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      39.99

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   SADABS,(BRUKER,2016)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34554
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         6.073
_diffrn_reflns_theta_max         40.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.874
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_point_group_measured_fraction_full 0.869
_reflns_number_total             9531
_reflns_number_gt                9415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_max     0.868
_reflns_Friedel_fraction_full    0.862

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.0869P] 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 4224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(6)
_chemical_absolute_configuration SYN
_refine_ls_number_reflns         9531
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71759(2) 0.62337(4) 0.12998(2) 0.02062(5) Uani 1 1 d . . . . .
O1 O 0.41181(6) 0.14438(9) 0.25327(4) 0.01692(9) Uani 1 1 d . . . . .
H1 H 0.3870 0.0208 0.2646 0.025 Uiso 1 1 calc R U . . .
O2 O 0.44744(8) 0.01629(10) 0.09834(5) 0.02338(12) Uani 1 1 d . . . . .
O3 O 0.33932(5) 0.75069(8) 0.28455(4) 0.01373(8) Uani 1 1 d . . . . .
O4 O 0.27390(5) 0.51247(9) 0.16579(4) 0.01429(8) Uani 1 1 d . . . . .
O5 O 0.77361(9) 0.98206(14) 0.26237(9) 0.0395(2) Uani 1 1 d . . . . .
O6 O 0.92787(10) 0.97576(18) 0.37447(8) 0.0409(2) Uani 1 1 d . . . . .
N1 N 0.48665(5) 0.53679(9) 0.20469(4) 0.01161(8) Uani 1 1 d . . . . .
N2 N 0.82589(7) 0.90541(11) 0.33744(6) 0.01979(11) Uani 1 1 d . . . . .
C1 C 0.60165(6) 0.66403(10) 0.23375(5) 0.01395(10) Uani 1 1 d . . . . .
H1A H 0.5747 0.8150 0.2348 0.017 Uiso 1 1 calc R U . . .
C2 C 0.50754(6) 0.37327(10) 0.12876(5) 0.01291(9) Uani 1 1 d . . . . .
H2 H 0.4658 0.4189 0.0635 0.015 Uiso 1 1 calc R U . . .
C3 C 0.65804(7) 0.35748(14) 0.11446(6) 0.01942(12) Uani 1 1 d . . . . .
H3A H 0.6792 0.3034 0.0463 0.023 Uiso 1 1 calc R U . . .
H3B H 0.6983 0.2634 0.1658 0.023 Uiso 1 1 calc R U . . .
C4 C 0.45119(7) 0.16043(10) 0.15799(5) 0.01363(9) Uani 1 1 d . . . . .
C5 C 0.36310(5) 0.61172(10) 0.22262(4) 0.01092(8) Uani 1 1 d . . . . .
C6 C 0.12979(6) 0.54749(12) 0.17689(6) 0.01578(10) Uani 1 1 d . . . . .
C7 C 0.09592(8) 0.77701(13) 0.15700(7) 0.02067(13) Uani 1 1 d . . . . .
H7A H 0.1279 0.8631 0.2136 0.031 Uiso 1 1 calc R U . . .
H7B H -0.0005 0.7926 0.1502 0.031 Uiso 1 1 calc R U . . .
H7C H 0.1386 0.8230 0.0944 0.031 Uiso 1 1 calc R U . . .
C8 C 0.08616(9) 0.47218(15) 0.28018(7) 0.02363(14) Uani 1 1 d . . . . .
H8A H 0.1213 0.3310 0.2925 0.035 Uiso 1 1 calc R U . . .
H8B H -0.0110 0.4687 0.2826 0.035 Uiso 1 1 calc R U . . .
H8C H 0.1200 0.5681 0.3322 0.035 Uiso 1 1 calc R U . . .
C9 C 0.07404(9) 0.40815(19) 0.09339(9) 0.0297(2) Uani 1 1 d . . . . .
H9A H 0.1079 0.4552 0.0279 0.045 Uiso 1 1 calc R U . . .
H9B H -0.0231 0.4169 0.0931 0.045 Uiso 1 1 calc R U . . .
H9C H 0.1013 0.2626 0.1054 0.045 Uiso 1 1 calc R U . . .
C10 C 0.66167(6) 0.60723(11) 0.33608(5) 0.01378(9) Uani 1 1 d . . . . .
C11 C 0.76701(7) 0.71638(12) 0.38284(6) 0.01549(10) Uani 1 1 d . . . . .
C12 C 0.82299(8) 0.65411(15) 0.47455(6) 0.02123(13) Uani 1 1 d . . . . .
H12 H 0.8951 0.7304 0.5030 0.025 Uiso 1 1 calc R U . . .
C13 C 0.77276(10) 0.48006(18) 0.52406(7) 0.02601(16) Uani 1 1 d . . . . .
H13 H 0.8103 0.4356 0.5866 0.031 Uiso 1 1 calc R U . . .
C14 C 0.66691(10) 0.37125(16) 0.48132(7) 0.02484(16) Uani 1 1 d . . . . .
H14 H 0.6309 0.2533 0.5155 0.030 Uiso 1 1 calc R U . . .
C15 C 0.61310(8) 0.43365(12) 0.38883(6) 0.01870(12) Uani 1 1 d . . . . .
H15 H 0.5413 0.3560 0.3607 0.022 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 C3 1.8089(10) . ?
S1 C1 1.8272(7) . ?
O1 C4 1.3278(8) . ?
O1 H1 0.8400 . ?
O2 C4 1.2112(9) . ?
O3 C5 1.2311(8) . ?
O4 C5 1.3277(8) . ?
O4 C6 1.4777(8) . ?
O5 N2 1.2224(11) . ?
O6 N2 1.2205(10) . ?
N1 C5 1.3561(8) . ?
N1 C2 1.4634(9) . ?
N1 C1 1.4635(8) . ?
N2 C11 1.4728(10) . ?
C1 C10 1.5220(9) . ?
C1 H1A 1.0000 . ?
C2 C4 1.5215(10) . ?
C2 C3 1.5331(10) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C8 1.5160(12) . ?
C6 C9 1.5213(11) . ?
C6 C7 1.5245(11) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.3981(10) . ?
C10 C11 1.4084(9) . ?
C11 C12 1.3916(11) . ?
C12 C13 1.3858(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.3890(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.3923(11) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C3 S1 C1 90.26(3) . . ?
C4 O1 H1 109.5 . . ?
C5 O4 C6 122.25(5) . . ?
C5 N1 C2 120.50(5) . . ?
C5 N1 C1 119.03(5) . . ?
C2 N1 C1 117.20(5) . . ?
O6 N2 O5 122.39(8) . . ?
O6 N2 C11 118.52(7) . . ?
O5 N2 C11 119.04(7) . . ?
N1 C1 C10 114.24(5) . . ?
N1 C1 S1 103.51(5) . . ?
C10 C1 S1 112.45(4) . . ?
N1 C1 H1A 108.8 . . ?
C10 C1 H1A 108.8 . . ?
S1 C1 H1A 108.8 . . ?
N1 C2 C4 113.88(5) . . ?
N1 C2 C3 106.19(6) . . ?
C4 C2 C3 110.13(6) . . ?
N1 C2 H2 108.8 . . ?
C4 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C2 C3 S1 104.61(5) . . ?
C2 C3 H3A 110.8 . . ?
S1 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
S1 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
O2 C4 O1 123.47(7) . . ?
O2 C4 C2 121.37(6) . . ?
O1 C4 C2 115.12(6) . . ?
O3 C5 O4 125.80(5) . . ?
O3 C5 N1 123.58(6) . . ?
O4 C5 N1 110.61(5) . . ?
O4 C6 C8 109.47(6) . . ?
O4 C6 C9 101.41(6) . . ?
C8 C6 C9 111.17(8) . . ?
O4 C6 C7 110.29(6) . . ?
C8 C6 C7 113.15(7) . . ?
C9 C6 C7 110.72(8) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 115.93(6) . . ?
C15 C10 C1 119.57(6) . . ?
C11 C10 C1 124.49(6) . . ?
C12 C11 C10 122.77(7) . . ?
C12 C11 N2 115.25(6) . . ?
C10 C11 N2 121.98(6) . . ?
C13 C12 C11 119.53(7) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.31(7) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.52(8) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 121.92(7) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?

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
C5 N1 C1 C10 96.38(7) . . . . ?
C2 N1 C1 C10 -103.90(7) . . . . ?
C5 N1 C1 S1 -141.01(5) . . . . ?
C2 N1 C1 S1 18.71(6) . . . . ?
C3 S1 C1 N1 -33.44(5) . . . . ?
C3 S1 C1 C10 90.35(5) . . . . ?
C5 N1 C2 C4 -69.12(7) . . . . ?
C1 N1 C2 C4 131.47(6) . . . . ?
C5 N1 C2 C3 169.51(6) . . . . ?
C1 N1 C2 C3 10.10(7) . . . . ?
N1 C2 C3 S1 -34.48(6) . . . . ?
C4 C2 C3 S1 -158.22(5) . . . . ?
C1 S1 C3 C2 39.96(5) . . . . ?
N1 C2 C4 O2 171.54(7) . . . . ?
C3 C2 C4 O2 -69.32(9) . . . . ?
N1 C2 C4 O1 -10.72(8) . . . . ?
C3 C2 C4 O1 108.43(7) . . . . ?
C6 O4 C5 O3 -5.16(10) . . . . ?
C6 O4 C5 N1 173.85(6) . . . . ?
C2 N1 C5 O3 -179.12(6) . . . . ?
C1 N1 C5 O3 -20.08(9) . . . . ?
C2 N1 C5 O4 1.85(8) . . . . ?
C1 N1 C5 O4 160.89(6) . . . . ?
C5 O4 C6 C8 -64.96(9) . . . . ?
C5 O4 C6 C9 177.51(8) . . . . ?
C5 O4 C6 C7 60.16(9) . . . . ?
N1 C1 C10 C15 5.53(9) . . . . ?
S1 C1 C10 C15 -112.07(7) . . . . ?
N1 C1 C10 C11 -175.64(6) . . . . ?
S1 C1 C10 C11 66.76(8) . . . . ?
C15 C10 C11 C12 1.73(11) . . . . ?
C1 C10 C11 C12 -177.15(7) . . . . ?
C15 C10 C11 N2 -178.39(7) . . . . ?
C1 C10 C11 N2 2.74(11) . . . . ?
O6 N2 C11 C12 9.67(13) . . . . ?
O5 N2 C11 C12 -172.68(10) . . . . ?
O6 N2 C11 C10 -170.22(10) . . . . ?
O5 N2 C11 C10 7.43(13) . . . . ?
C10 C11 C12 C13 -1.24(13) . . . . ?
N2 C11 C12 C13 178.87(9) . . . . ?
C11 C12 C13 C14 -0.24(15) . . . . ?
C12 C13 C14 C15 1.14(17) . . . . ?
C13 C14 C15 C10 -0.61(16) . . . . ?
C11 C10 C15 C14 -0.79(12) . . . . ?
C1 C10 C15 C14 178.14(8) . . . . ?

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
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455
O1 H1 O3 0.84 1.81 2.6466(7) 177.2 1_545
C1 H1A O2 1.00 2.55 3.2590(9) 127.5 1_565
C2 H2 O2 1.00 2.40 3.1742(9) 133.7 2_655
C3 H3B O5 0.99 2.33 3.2975(11) 166.8 1_545
C7 H7A O3 0.98 2.43 2.9713(10) 114.4 .
C8 H8C O3 0.98 2.58 3.1081(10) 113.8 .
C9 H9B S1 0.98 2.97 3.8787(10) 154.7 1_455

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_BJ_18_BOC_0m
_database_code_depnum_ccdc_archive 'CCDC 1565478'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 Cl2 N O4 S'
_chemical_formula_sum            'C15 H17 Cl2 N O4 S'
_chemical_formula_weight         378.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4352(11)
_cell_length_b                   10.4526(12)
_cell_length_c                   18.336(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1808.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9121
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.61

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.491
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_process_details   sadabs,(bruker,2016)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18873
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         24.986
_diffrn_reflns_theta_full        24.986
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3186
_reflns_number_gt                3072
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.5592P] 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 1233 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(16)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3186
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
Cl1 Cl 1.04747(13) 1.08512(11) 0.85695(6) 0.0719(3) Uani 1 1 d . . . . .
Cl2 Cl 0.77492(19) 0.70985(12) 1.00835(10) 0.1107(6) Uani 1 1 d . . . . .
S1 S 0.96133(10) 1.05750(9) 1.04529(4) 0.0512(2) Uani 1 1 d . . . . .
O1 O 0.9880(3) 1.3690(3) 0.9677(2) 0.0756(9) Uani 1 1 d . . . . .
O2 O 0.8439(4) 1.3467(3) 0.87425(18) 0.0718(8) Uani 1 1 d . . . . .
H2 H 0.7762 1.3013 0.8634 0.108 Uiso 1 1 calc R U . . .
O3 O 0.6307(3) 1.1850(2) 0.85707(14) 0.0529(6) Uani 1 1 d . . . . .
O4 O 0.6441(3) 0.9709(2) 0.87766(13) 0.0509(6) Uani 1 1 d . . . . .
N1 N 0.7748(3) 1.1021(2) 0.94340(13) 0.0376(6) Uani 1 1 d . . . . .
C1 C 0.8370(3) 0.9902(3) 0.97980(17) 0.0393(7) Uani 1 1 d . . . . .
H1 H 0.7619 0.9459 1.0067 0.047 Uiso 1 1 calc R U . . .
C2 C 0.7904(4) 1.2253(3) 0.98210(19) 0.0451(8) Uani 1 1 d . . . . .
H2A H 0.6963 1.2643 0.9867 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8434(4) 1.1924(4) 1.0578(2) 0.0547(9) Uani 1 1 d . . . . .
H3A H 0.7650 1.1697 1.0895 0.066 Uiso 1 1 calc R U . . .
H3B H 0.8937 1.2643 1.0790 0.066 Uiso 1 1 calc R U . . .
C4 C 0.8866(4) 1.3186(3) 0.9413(2) 0.0544(9) Uani 1 1 d . . . . .
C5 C 0.6783(3) 1.0908(3) 0.88978(16) 0.0399(7) Uani 1 1 d . . . . .
C6 C 0.5702(5) 0.9310(5) 0.8097(2) 0.0721(12) Uani 1 1 d . . . . .
C7 C 0.5671(9) 0.7879(6) 0.8189(5) 0.134(3) Uani 1 1 d . . . . .
H7A H 0.5305 0.7671 0.8663 0.200 Uiso 1 1 calc R U . . .
H7B H 0.6614 0.7545 0.8141 0.200 Uiso 1 1 calc R U . . .
H7C H 0.5074 0.7509 0.7821 0.200 Uiso 1 1 calc R U . . .
C8 C 0.4227(5) 0.9854(6) 0.8085(3) 0.0895(16) Uani 1 1 d . . . . .
H8A H 0.3704 0.9484 0.7688 0.134 Uiso 1 1 calc R U . . .
H8B H 0.4274 1.0765 0.8022 0.134 Uiso 1 1 calc R U . . .
H8C H 0.3759 0.9661 0.8537 0.134 Uiso 1 1 calc R U . . .
C9 C 0.6589(6) 0.9732(7) 0.7451(3) 0.111(2) Uani 1 1 d . . . . .
H9A H 0.7535 0.9407 0.7502 0.167 Uiso 1 1 calc R U . . .
H9B H 0.6615 1.0650 0.7432 0.167 Uiso 1 1 calc R U . . .
H9C H 0.6178 0.9407 0.7009 0.167 Uiso 1 1 calc R U . . .
C10 C 0.9089(4) 0.8952(3) 0.93034(19) 0.0447(7) Uani 1 1 d . . . . .
C11 C 0.8847(5) 0.7635(4) 0.9393(3) 0.0665(11) Uani 1 1 d . . . . .
C12 C 0.9444(7) 0.6735(4) 0.8940(4) 0.0953(18) Uani 1 1 d . . . . .
H12 H 0.9276 0.5870 0.9019 0.114 Uiso 1 1 calc R U . . .
C13 C 1.0288(7) 0.7118(6) 0.8373(4) 0.0998(19) Uani 1 1 d . . . . .
H13 H 1.0669 0.6510 0.8059 0.120 Uiso 1 1 calc R U . . .
C14 C 1.0572(5) 0.8370(5) 0.8266(3) 0.0778(13) Uani 1 1 d . . . . .
H14 H 1.1148 0.8626 0.7881 0.093 Uiso 1 1 calc R U . . .
C15 C 0.9997(4) 0.9271(4) 0.8736(2) 0.0516(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C15 1.739(4) . ?
Cl2 C11 1.730(5) . ?
S1 C3 1.811(4) . ?
S1 C1 1.820(3) . ?
O1 C4 1.195(5) . ?
O2 C4 1.327(5) . ?
O2 H2 0.8200 . ?
O3 C5 1.237(4) . ?
O4 C5 1.313(4) . ?
O4 C6 1.488(4) . ?
N1 C5 1.345(4) . ?
N1 C1 1.469(4) . ?
N1 C2 1.477(4) . ?
C1 C10 1.507(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.515(5) . ?
C2 C4 1.528(5) . ?
C2 H2A 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C8 1.504(7) . ?
C6 C7 1.506(8) . ?
C6 C9 1.516(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.389(5) . ?
C10 C11 1.405(5) . ?
C11 C12 1.375(7) . ?
C12 C13 1.369(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.350(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(6) . ?
C14 H14 0.9300 . ?

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
C3 S1 C1 89.34(16) . . ?
C4 O2 H2 109.5 . . ?
C5 O4 C6 121.6(3) . . ?
C5 N1 C1 122.1(3) . . ?
C5 N1 C2 119.7(3) . . ?
C1 N1 C2 115.9(2) . . ?
N1 C1 C10 115.6(3) . . ?
N1 C1 S1 104.4(2) . . ?
C10 C1 S1 111.2(2) . . ?
N1 C1 H1 108.5 . . ?
C10 C1 H1 108.5 . . ?
S1 C1 H1 108.5 . . ?
N1 C2 C3 106.0(3) . . ?
N1 C2 C4 112.4(3) . . ?
C3 C2 C4 113.4(3) . . ?
N1 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
C4 C2 H2A 108.3 . . ?
C2 C3 S1 105.2(2) . . ?
C2 C3 H3A 110.7 . . ?
S1 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
S1 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
O1 C4 O2 121.4(4) . . ?
O1 C4 C2 124.0(4) . . ?
O2 C4 C2 114.5(3) . . ?
O3 C5 O4 126.0(3) . . ?
O3 C5 N1 122.0(3) . . ?
O4 C5 N1 112.0(3) . . ?
O4 C6 C8 109.9(4) . . ?
O4 C6 C7 101.2(4) . . ?
C8 C6 C7 111.1(5) . . ?
O4 C6 C9 108.3(4) . . ?
C8 C6 C9 113.0(5) . . ?
C7 C6 C9 112.8(6) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 115.0(4) . . ?
C15 C10 C1 124.8(3) . . ?
C11 C10 C1 120.2(3) . . ?
C12 C11 C10 122.2(5) . . ?
C12 C11 Cl2 117.8(4) . . ?
C10 C11 Cl2 120.0(3) . . ?
C13 C12 C11 119.8(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.6(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.4(5) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 122.9(4) . . ?
C10 C15 Cl1 121.3(3) . . ?
C14 C15 Cl1 115.8(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
C5 N1 C1 C10 56.4(4) . . . . ?
C2 N1 C1 C10 -141.0(3) . . . . ?
C5 N1 C1 S1 178.9(2) . . . . ?
C2 N1 C1 S1 -18.5(3) . . . . ?
C3 S1 C1 N1 33.8(2) . . . . ?
C3 S1 C1 C10 159.1(3) . . . . ?
C5 N1 C2 C3 151.9(3) . . . . ?
C1 N1 C2 C3 -11.2(4) . . . . ?
C5 N1 C2 C4 -83.7(4) . . . . ?
C1 N1 C2 C4 113.2(3) . . . . ?
N1 C2 C3 S1 35.9(3) . . . . ?
C4 C2 C3 S1 -87.8(3) . . . . ?
C1 S1 C3 C2 -41.1(3) . . . . ?
N1 C2 C4 O1 -125.5(4) . . . . ?
C3 C2 C4 O1 -5.4(5) . . . . ?
N1 C2 C4 O2 58.5(4) . . . . ?
C3 C2 C4 O2 178.6(3) . . . . ?
C6 O4 C5 O3 16.0(5) . . . . ?
C6 O4 C5 N1 -163.7(3) . . . . ?
C1 N1 C5 O3 -176.8(3) . . . . ?
C2 N1 C5 O3 21.2(4) . . . . ?
C1 N1 C5 O4 3.0(4) . . . . ?
C2 N1 C5 O4 -159.0(3) . . . . ?
C5 O4 C6 C8 -67.3(5) . . . . ?
C5 O4 C6 C7 175.3(5) . . . . ?
C5 O4 C6 C9 56.5(5) . . . . ?
N1 C1 C10 C15 44.1(5) . . . . ?
S1 C1 C10 C15 -74.7(4) . . . . ?
N1 C1 C10 C11 -135.0(4) . . . . ?
S1 C1 C10 C11 106.2(4) . . . . ?
C15 C10 C11 C12 -1.3(6) . . . . ?
C1 C10 C11 C12 177.9(4) . . . . ?
C15 C10 C11 Cl2 179.5(3) . . . . ?
C1 C10 C11 Cl2 -1.3(5) . . . . ?
C10 C11 C12 C13 -1.1(8) . . . . ?
Cl2 C11 C12 C13 178.1(5) . . . . ?
C11 C12 C13 C14 1.9(10) . . . . ?
C12 C13 C14 C15 -0.2(9) . . . . ?
C11 C10 C15 C14 3.1(6) . . . . ?
C1 C10 C15 C14 -176.1(4) . . . . ?
C11 C10 C15 Cl1 -177.3(3) . . . . ?
C1 C10 C15 Cl1 3.5(5) . . . . ?
C13 C14 C15 C10 -2.4(7) . . . . ?
C13 C14 C15 Cl1 178.0(5) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_BJ4_BOC_B_ACN
_database_code_depnum_ccdc_archive 'CCDC 1565470'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N O5 S'
_chemical_formula_sum            'C15 H19 N O5 S'
_chemical_formula_weight         325.37

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           79
_space_group_name_H-M_alt        'I 4'
_space_group_name_Hall           'I 4'

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

_cell_length_a                   22.5029(5)
_cell_length_b                   22.5029(5)
_cell_length_c                   6.4423(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3262.26(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      34.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   sadabs,(bruker,2016)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27810
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.622
_diffrn_reflns_theta_max         34.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measured_fraction_theta_full 0.735
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_Laue_measured_fraction_full 0.735
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.729
_reflns_number_total             5796
_reflns_number_gt                5115
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.834
_reflns_Friedel_fraction_full    0.722

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0921P)²+0.2969P] 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 1988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5796
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1567
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61610(4) 0.50332(4) 0.3548(2) 0.0476(3) Uani 1 1 d . . . . .
O1 O 0.71121(17) 0.58815(14) 0.9420(4) 0.0477(8) Uani 1 1 d . . . . .
O2 O 0.76774(9) 0.51247(8) 0.8409(3) 0.0195(3) Uani 1 1 d . . . . .
H2 H 0.7809 0.5157 0.9624 0.029 Uiso 1 1 calc R U . . .
O3 O 0.80747(10) 0.51130(9) 0.2213(3) 0.0244(4) Uani 1 1 d . . . . .
O4 O 0.80382(8) 0.58050(8) 0.4786(3) 0.0178(3) Uani 1 1 d . . . . .
O5 O 0.65612(13) 0.38908(13) 0.0546(3) 0.0373(6) Uani 1 1 d . . . . .
H5 H 0.6514 0.3602 -0.0265 0.056 Uiso 1 1 calc R U . . .
N1 N 0.72790(10) 0.51902(9) 0.4396(3) 0.0189(4) Uani 1 1 d . . . . .
C1 C 0.69207(14) 0.47729(12) 0.3179(4) 0.0260(5) Uani 1 1 d . . . . .
H1 H 0.7027 0.4820 0.1681 0.031 Uiso 1 1 calc R U . . .
C2 C 0.69755(11) 0.55323(11) 0.5992(4) 0.0201(4) Uani 1 1 d . . . . .
H2A H 0.6934 0.5953 0.5508 0.024 Uiso 1 1 calc R U . . .
C3 C 0.63528(14) 0.52468(14) 0.6116(7) 0.0368(8) Uani 1 1 d . . . . .
H3A H 0.6060 0.5535 0.6665 0.044 Uiso 1 1 calc R U . . .
H3B H 0.6360 0.4896 0.7041 0.044 Uiso 1 1 calc R U . . .
C4 C 0.72664(13) 0.55299(11) 0.8093(4) 0.0222(4) Uani 1 1 d . . . . .
C5 C 0.78196(11) 0.53535(10) 0.3686(4) 0.0178(4) Uani 1 1 d . . . . .
C6 C 0.86739(11) 0.59791(12) 0.4641(4) 0.0213(4) Uani 1 1 d . . . . .
C7 C 0.88262(16) 0.61836(16) 0.2463(6) 0.0333(7) Uani 1 1 d . . . . .
H7A H 0.8791 0.5848 0.1501 0.050 Uiso 1 1 calc R U . . .
H7B H 0.9234 0.6336 0.2437 0.050 Uiso 1 1 calc R U . . .
H7C H 0.8551 0.6499 0.2042 0.050 Uiso 1 1 calc R U . . .
C8 C 0.90559(16) 0.54646(15) 0.5358(7) 0.0348(7) Uani 1 1 d . . . . .
H8A H 0.8944 0.5353 0.6776 0.052 Uiso 1 1 calc R U . . .
H8B H 0.9475 0.5583 0.5333 0.052 Uiso 1 1 calc R U . . .
H8C H 0.8997 0.5125 0.4431 0.052 Uiso 1 1 calc R U . . .
C9 C 0.87021(14) 0.64946(14) 0.6180(6) 0.0300(6) Uani 1 1 d . . . . .
H9A H 0.8450 0.6820 0.5687 0.045 Uiso 1 1 calc R U . . .
H9B H 0.9113 0.6634 0.6300 0.045 Uiso 1 1 calc R U . . .
H9C H 0.8561 0.6360 0.7541 0.045 Uiso 1 1 calc R U . . .
C10 C 0.69965(11) 0.41306(10) 0.3767(4) 0.0171(4) Uani 1 1 d . . . . .
C11 C 0.68075(12) 0.36946(13) 0.2364(4) 0.0217(5) Uani 1 1 d . . . . .
C12 C 0.68789(12) 0.30923(13) 0.2819(5) 0.0259(5) Uani 1 1 d . . . . .
H12 H 0.6765 0.2800 0.1833 0.031 Uiso 1 1 calc R U . . .
C13 C 0.71155(13) 0.29225(12) 0.4702(6) 0.0288(6) Uani 1 1 d . . . . .
H13 H 0.7156 0.2512 0.5023 0.035 Uiso 1 1 calc R U . . .
C14 C 0.72943(13) 0.33493(12) 0.6133(5) 0.0259(5) Uani 1 1 d . . . . .
H14 H 0.7453 0.3231 0.7435 0.031 Uiso 1 1 calc R U . . .
C15 C 0.72395(12) 0.39522(11) 0.5651(4) 0.0199(4) Uani 1 1 d . . . . .
H15 H 0.7370 0.4243 0.6619 0.024 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 C3 1.776(5) . ?
S1 C1 1.823(3) . ?
O1 C4 1.215(3) . ?
O2 C4 1.315(3) . ?
O2 H2 0.8400 . ?
O3 C5 1.234(3) . ?
O4 C5 1.333(3) . ?
O4 C6 1.486(3) . ?
O5 C11 1.369(4) . ?
O5 H5 0.8400 . ?
N1 C5 1.351(3) . ?
N1 C2 1.455(4) . ?
N1 C1 1.465(3) . ?
C1 C10 1.504(4) . ?
C1 H1 1.0000 . ?
C2 C4 1.504(4) . ?
C2 C3 1.544(4) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C7 1.516(4) . ?
C6 C8 1.514(4) . ?
C6 C9 1.527(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.390(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.396(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C3 S1 C1 88.88(14) . . ?
C4 O2 H2 109.5 . . ?
C5 O4 C6 121.5(2) . . ?
C11 O5 H5 109.5 . . ?
C5 N1 C2 121.2(2) . . ?
C5 N1 C1 119.3(2) . . ?
C2 N1 C1 117.3(2) . . ?
N1 C1 C10 114.8(2) . . ?
N1 C1 S1 103.9(2) . . ?
C10 C1 S1 112.49(19) . . ?
N1 C1 H1 108.5 . . ?
C10 C1 H1 108.5 . . ?
S1 C1 H1 108.5 . . ?
N1 C2 C4 115.5(2) . . ?
N1 C2 C3 104.0(2) . . ?
C4 C2 C3 110.3(3) . . ?
N1 C2 H2A 108.9 . . ?
C4 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C2 C3 S1 106.6(3) . . ?
C2 C3 H3A 110.4 . . ?
S1 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
S1 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O1 C4 O2 122.9(3) . . ?
O1 C4 C2 120.4(3) . . ?
O2 C4 C2 116.6(2) . . ?
O3 C5 O4 124.9(2) . . ?
O3 C5 N1 124.1(2) . . ?
O4 C5 N1 111.1(2) . . ?
O4 C6 C7 110.8(2) . . ?
O4 C6 C8 109.0(2) . . ?
C7 C6 C8 112.7(3) . . ?
O4 C6 C9 101.5(2) . . ?
C7 C6 C9 111.2(3) . . ?
C8 C6 C9 111.0(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.7(2) . . ?
C15 C10 C1 122.8(2) . . ?
C11 C10 C1 118.4(2) . . ?
O5 C11 C12 122.6(2) . . ?
O5 C11 C10 116.7(3) . . ?
C12 C11 C10 120.6(3) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.6(2) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C10 92.9(3) . . . . ?
C2 N1 C1 C10 -103.7(3) . . . . ?
C5 N1 C1 S1 -143.9(2) . . . . ?
C2 N1 C1 S1 19.5(3) . . . . ?
C3 S1 C1 N1 -34.38(19) . . . . ?
C3 S1 C1 C10 90.3(2) . . . . ?
C5 N1 C2 C4 -66.4(3) . . . . ?
C1 N1 C2 C4 130.6(2) . . . . ?
C5 N1 C2 C3 172.6(2) . . . . ?
C1 N1 C2 C3 9.6(3) . . . . ?
N1 C2 C3 S1 -35.6(3) . . . . ?
C4 C2 C3 S1 -159.96(19) . . . . ?
C1 S1 C3 C2 41.4(2) . . . . ?
N1 C2 C4 O1 166.8(3) . . . . ?
C3 C2 C4 O1 -75.6(4) . . . . ?
N1 C2 C4 O2 -14.7(3) . . . . ?
C3 C2 C4 O2 102.8(3) . . . . ?
C6 O4 C5 O3 -13.8(4) . . . . ?
C6 O4 C5 N1 166.1(2) . . . . ?
C2 N1 C5 O3 -173.3(2) . . . . ?
C1 N1 C5 O3 -10.6(4) . . . . ?
C2 N1 C5 O4 6.8(3) . . . . ?
C1 N1 C5 O4 169.5(2) . . . . ?
C5 O4 C6 C7 62.8(3) . . . . ?
C5 O4 C6 C8 -61.8(3) . . . . ?
C5 O4 C6 C9 -179.0(2) . . . . ?
N1 C1 C10 C15 18.1(4) . . . . ?
S1 C1 C10 C15 -100.4(3) . . . . ?
N1 C1 C10 C11 -162.7(2) . . . . ?
S1 C1 C10 C11 78.8(3) . . . . ?
C15 C10 C11 O5 178.8(3) . . . . ?
C1 C10 C11 O5 -0.4(4) . . . . ?
C15 C10 C11 C12 -2.0(4) . . . . ?
C1 C10 C11 C12 178.7(3) . . . . ?
O5 C11 C12 C13 -178.2(3) . . . . ?
C10 C11 C12 C13 2.7(4) . . . . ?
C11 C12 C13 C14 -1.3(4) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C11 C10 C15 C14 0.0(4) . . . . ?
C1 C10 C15 C14 179.3(3) . . . . ?
C13 C14 C15 C10 1.3(5) . . . . ?

_refine_diff_density_max         1.456
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.078

