# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_KHG-R165
_audit_block_doi                 10.5517/cc10vd6g
_database_code_depnum_ccdc_archive 'CCDC 948885'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tet.2014.03.053 2014
_audit_update_record             
;
2013-07-05 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2012-11-26
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_systematic        1,5,3-dithiazepan-3-ol
_chemical_formula_moiety         '0.67(C4 H9 N O S2)'
_chemical_formula_sum            'C2.667 H6 N0.667 O0.667 S1.333'
_chemical_formula_weight         100.84
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P 1'
_symmetry_int_tables_number      1
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_cell_length_a                   6.5991(7)
_cell_length_b                   6.9097(7)
_cell_length_c                   8.2602(9)
_cell_angle_alpha                109.839(10)
_cell_angle_beta                 95.545(9)
_cell_angle_gamma                94.714(8)
_cell_volume                     349.97(7)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2575
_cell_measurement_theta_max      31.1844
_cell_measurement_theta_min      2.6395
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_recrystallization_method 'hexane, ethylacetate, chloroforme'
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293.2
_exptl_crystal_colour_modifier   ?
_exptl_crystal_density_diffrn    1.4353
_exptl_crystal_F_000             160.5417
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5222
_diffrn_reflns_theta_full        31.254342
_diffrn_reflns_theta_max         31.25
_diffrn_reflns_theta_min         2.64
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9892
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -10.00   47.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -      -23.6098   77.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00  -32.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -      -23.6098  178.0000  150.0000 68

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   40.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -      -23.6098   57.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   47.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -      -23.6098   77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   95.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -       24.3911   77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
  6 omega    4.00   93.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -       24.3911   57.0000  -60.0000 89

#__ type_ start__ end____ width___ exp.time_
  7 omega  -23.00   63.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -       24.3911  -99.0000  150.0000 86

#__ type_ start__ end____ width___ exp.time_
  8 omega   18.00   72.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -       24.3911   57.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   66.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -       24.3911  -99.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   -5.00   89.00   1.0000    6.3000
omega____ theta____ kappa____ phi______ frames
    -       24.3911   77.0000 -180.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0495988000
_diffrn_orient_matrix_UB_12      0.0559316000
_diffrn_orient_matrix_UB_13      -0.0467288000
_diffrn_orient_matrix_UB_21      0.0889913000
_diffrn_orient_matrix_UB_22      0.0071396000
_diffrn_orient_matrix_UB_23      -0.0404219000
_diffrn_orient_matrix_UB_31      -0.0382196000
_diffrn_orient_matrix_UB_32      -0.0944048000
_diffrn_orient_matrix_UB_33      -0.0683050000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'Xcalibur Eos'
_reflns_Friedel_coverage         0.768
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -10
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                3197
_reflns_number_total             3814
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.287669
_refine_diff_density_min         -0.328083
_refine_diff_density_rms         0.054512
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.46(11)
_refine_ls_d_res_high            0.684925
_refine_ls_d_res_low             7.701107
_refine_ls_goodness_of_fit_ref   1.106929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.044094
_refine_ls_R_factor_gt           0.035372
_refine_ls_restrained_S_all      1.106929
_refine_ls_shift/su_max          9.7732
_refine_ls_shift/su_mean         1.0583
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.0384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.110300
_atom_sites_solution_primary     direct
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_refinement_flags_posn
S1 S -0.15887(13) 0.32920(13) 0.93624(11) 0.0499(3) Uani 1.000000 .
S2 S 0.32912(14) 0.46287(13) 0.83291(12) 0.0513(3) Uani 1.000000 .
S3 S 0.77122(13) 0.99383(13) 0.32547(12) 0.0476(3) Uani 1.000000 .
S4 S 0.28269(13) 0.85842(14) 0.42668(13) 0.0521(3) Uani 1.000000 .
N1 N -0.0603(6) 0.5691(5) 0.7455(5) 0.0423(9) Uani 1.000000 .
N2 N 0.6691(5) 0.7571(5) 0.5191(5) 0.0419(9) Uani 1.000000 .
C3 C 0.5051(7) 0.8814(7) 0.5789(6) 0.0446(11) Uani 1.000000 .
O4 O 0.5978(5) 0.5419(4) 0.4975(4) 0.0603(11) Uani 1.000000 .
O5 O 0.0127(6) 0.7799(5) 0.7671(5) 0.0632(12) Uani 1.000000 .
C6 C 0.7162(7) 0.7440(6) 0.3469(6) 0.0431(11) Uani 1.000000 .
C7 C 0.0886(8) 0.2975(9) 1.0332(7) 0.0605(15) Uani 1.000000 .
C8 C 0.5211(7) 1.0281(6) 0.2337(6) 0.0504(13) Uani 1.000000 .
C9 C 0.1032(7) 0.4460(7) 0.6812(6) 0.0447(11) Uani 1.000000 .
C10 C -0.1067(7) 0.5795(7) 0.9190(6) 0.0502(12) Uani 1.000000 .
C11 C 0.3564(7) 1.0583(7) 0.3490(7) 0.0615(14) Uani 1.000000 .
C12 C 0.2490(8) 0.2505(7) 0.9091(7) 0.0520(14) Uani 1.000000 .
H10a H 0.022(6) 0.679(5) 1.009(5) 0.043(10) Uiso 1.000000 .
H6a H 0.612(6) 0.690(5) 0.269(5) 0.033(9) Uiso 1.000000 .
H9a H 0.060(5) 0.333(5) 0.654(4) 0.036(8) Uiso 1.000000 .
H10b H -0.206(6) 0.678(5) 0.955(5) 0.045(9) Uiso 1.000000 .
H3a H 0.486(5) 0.852(4) 0.665(4) 0.023(6) Uiso 1.000000 .
H4 H 0.702(4) 0.522(4) 0.580(3) 0.027(6) Uiso 1.000000 .
H8a H 0.551(4) 1.155(4) 0.202(3) 0.027(6) Uiso 1.000000 .
H7a H 0.140(5) 0.443(5) 1.155(4) 0.040(8) Uiso 1.000000 .
H11a H 0.412(7) 1.181(7) 0.460(6) 0.048(12) Uiso 1.000000 .
H12a H 0.228(9) 0.112(9) 0.818(7) 0.079(17) Uiso 1.000000 .
H11b H 0.232(3) 1.078(3) 0.270(3) 0.046(4) Uiso 1.000000 .
H5 H -0.079(8) 0.806(8) 0.767(7) 0.087(17) Uiso 1.000000 .
H6b H 0.857(6) 0.690(5) 0.337(5) 0.053(10) Uiso 1.000000 .
H12b H 0.360(11) 0.240(10) 0.961(9) 0.08(2) Uiso 1.000000 .
H9b H 0.189(6) 0.484(6) 0.587(5) 0.047(12) Uiso 1.000000 .
H3b H 0.564(5) 1.040(5) 0.640(4) 0.032(10) Uiso 1.000000 .
H8b H 0.519(5) 0.941(6) 0.169(4) 0.034(9) Uiso 1.000000 .
H7b H 0.063(8) 0.245(8) 1.114(7) 0.110(17) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.811(6) .
S1 C10 1.791(5) .
S2 C9 1.821(5) .
S2 C12 1.842(5) .
S3 C6 1.806(5) .
S3 C8 1.816(5) .
S4 C3 1.797(5) .
S4 C11 1.763(6) .
N1 O5 1.442(4) .
N1 C9 1.458(7) .
N1 C10 1.473(7) .
N2 C3 1.456(6) .
N2 O4 1.467(4) .
N2 C6 1.460(7) .
C3 H3a 0.82(3) .
C3 H3b 1.06(3) .
O4 H4 0.97(3) .
O5 H5 0.65(5) .
C6 H6a 0.86(4) .
C6 H6b 1.03(4) .
C7 C12 1.522(8) .
C7 H7a 1.15(3) .
C7 H7b 0.89(5) .
C8 C11 1.495(8) .
C8 H8a 1.01(3) .
C8 H8b 0.65(3) .
C9 H9a 0.76(3) .
C9 H9b 1.09(4) .
C10 H10a 1.08(3) .
C10 H10b 0.98(4) .
C11 H11a 1.02(4) .
C11 H11b 1.05(2) .
C12 H12a 0.98(6) .
C12 H12b 0.83(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
C10 S1 C7 101.4(2) . .
C12 S2 C9 100.1(2) . .
C8 S3 C6 101.0(2) . .
C11 S4 C3 100.4(2) . .
C9 N1 O5 106.3(3) . .
C10 N1 O5 104.4(3) . .
C10 N1 C9 115.3(4) . .
O4 N2 C3 107.7(3) . .
C6 N2 C3 114.5(4) . .
C6 N2 O4 103.7(3) . .
N2 C3 S4 118.6(3) . .
H3a C3 S4 117(2) . .
H3a C3 N2 100(2) . .
H3b C3 S4 109.3(19) . .
H3b C3 N2 111(2) . .
H3b C3 H3a 100(3) . .
H4 O4 N2 98.9(15) . .
H5 O5 N1 92(4) . .
N2 C6 S3 113.5(3) . .
H6a C6 S3 102(2) . .
H6a C6 N2 112(2) . .
H6b C6 S3 101.2(19) . .
H6b C6 N2 106(2) . .
H6b C6 H6a 123(3) . .
C12 C7 S1 114.3(4) . .
H7a C7 S1 107.4(16) . .
H7a C7 C12 113.2(16) . .
H7b C7 S1 106(3) . .
H7b C7 C12 129(3) . .
H7b C7 H7a 81(3) . .
C11 C8 S3 116.7(4) . .
H8a C8 S3 103.1(16) . .
H8a C8 C11 109.9(16) . .
H8b C8 S3 90(3) . .
H8b C8 C11 121(3) . .
H8b C8 H8a 113(3) . .
N1 C9 S2 118.5(3) . .
H9a C9 S2 102(3) . .
H9a C9 N1 107(3) . .
H9b C9 S2 95(2) . .
H9b C9 N1 118(2) . .
H9b C9 H9a 114(3) . .
N1 C10 S1 113.1(3) . .
H10a C10 S1 115(2) . .
H10a C10 N1 105(2) . .
H10b C10 S1 118(2) . .
H10b C10 N1 109(2) . .
H10b C10 H10a 95(3) . .
C8 C11 S4 118.3(3) . .
H11a C11 S4 104(3) . .
H11a C11 C8 107(3) . .
H11b C11 S4 109.6(12) . .
H11b C11 C8 102.2(13) . .
H11b C11 H11a 117(3) . .
C7 C12 S2 114.7(4) . .
H12a C12 S2 114(3) . .
H12a C12 C7 116(3) . .
H12b C12 S2 101(5) . .
H12b C12 C7 110(5) . .
H12b C12 H12a 98(5) . .

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

data_compound_5
_database_code_depnum_ccdc_archive 'CCDC 1403369'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2016-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        '2-(1,5,3-dithiazepan-3-yl)propanoic acid'
_chemical_formula_moiety         'C7 H13 N O2 S2'
_chemical_formula_sum            'C7 H13 N O2 S2'
_chemical_formula_weight         207.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.4993(6)
_cell_length_b                   8.6630(6)
_cell_length_c                   8.5034(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.738(7)
_cell_angle_gamma                90
_cell_volume                     463.01(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1257
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      31.1775
_cell_measurement_theta_min      2.3463
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             220.0
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2474
_diffrn_reflns_point_group_measured_fraction_full 0.849
_diffrn_reflns_point_group_measured_fraction_max 0.678
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.247
_diffrn_reflns_theta_min         2.477
_diffrn_ambient_temperature      200.2
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   64.00  100.00   1.0000    3.5900
omega____ theta____ kappa____ phi______ frames
    -       24.0786  178.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   82.00   1.0000    3.5900
omega____ theta____ kappa____ phi______ frames
    -       24.0786    0.0000 -120.0000 124

#__ type_ start__ end____ width___ exp.time_
  3 omega   25.00   92.00   1.0000    3.5900
omega____ theta____ kappa____ phi______ frames
    -       24.0786   77.0000   60.0000 67
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0218700000
_diffrn_orient_matrix_UB_12      -0.0290756000
_diffrn_orient_matrix_UB_13      -0.0805717000
_diffrn_orient_matrix_UB_21      -0.1102960000
_diffrn_orient_matrix_UB_22      0.0115168000
_diffrn_orient_matrix_UB_23      -0.0088166000
_diffrn_orient_matrix_UB_31      0.0083674000
_diffrn_orient_matrix_UB_32      0.0757372000
_diffrn_orient_matrix_UB_33      -0.0295939000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.455
_reflns_Friedel_fraction_full    0.674
_reflns_Friedel_fraction_max     0.451
_reflns_number_gt                1968
_reflns_number_total             2052
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2052
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.03071(13) -0.47972(10) -0.04969(10) 0.0196(2) Uani 1 1 d . . . . .
S5 S -0.49945(13) -0.53458(11) 0.07977(11) 0.0224(2) Uani 1 1 d . . . . .
N3 N -0.0840(4) -0.4950(3) 0.2687(3) 0.0154(5) Uani 1 1 d . . . . .
C10 C 0.3044(6) -0.4781(6) 0.4256(5) 0.0263(7) Uani 1 1 d . . . . .
O2 O -0.0459(5) -0.6434(4) 0.5691(4) 0.0319(7) Uani 1 1 d . . . . .
C2 C -0.0535(6) -0.3910(4) 0.1395(4) 0.0182(7) Uani 1 1 d . . . . .
C4 C -0.2560(6) -0.6096(4) 0.2090(4) 0.0186(7) Uani 1 1 d . . . . .
C9 C 0.0743(6) -0.6806(4) 0.4869(4) 0.0187(7) Uani 1 1 d . . . . .
O1 O 0.1910(5) -0.8068(3) 0.5097(4) 0.0266(6) Uani 1 1 d . . . . .
C8 C 0.1128(5) -0.5824(4) 0.3480(4) 0.0181(7) Uani 1 1 d . . . . .
C6 C -0.4609(6) -0.5699(5) -0.1210(5) 0.0246(8) Uani 1 1 d . . . . .
C7 C -0.3030(5) -0.4637(5) -0.1718(4) 0.0223(7) Uani 1 1 d . . . . .
H4A H -0.293(6) -0.651(5) 0.305(5) 0.012(10) Uiso 1 1 d . . . . .
H10A H 0.351(9) -0.418(7) 0.346(7) 0.036(15) Uiso 1 1 d . . . . .
H7A H -0.277(6) -0.494(6) -0.272(5) 0.015(10) Uiso 1 1 d . . . . .
H2A H -0.180(7) -0.318(6) 0.108(6) 0.019(11) Uiso 1 1 d . . . . .
H2B H 0.076(7) -0.322(5) 0.183(5) 0.017(11) Uiso 1 1 d . . . . .
H8 H 0.152(7) -0.644(5) 0.268(6) 0.015(10) Uiso 1 1 d . . . . .
H7B H -0.346(7) -0.363(6) -0.172(6) 0.018(11) Uiso 1 1 d . . . . .
H6A H -0.410(7) -0.672(6) -0.122(5) 0.021(12) Uiso 1 1 d . . . . .
H10B H 0.262(9) -0.412(7) 0.511(7) 0.039(16) Uiso 1 1 d . . . . .
H10C H 0.402(9) -0.555(7) 0.468(7) 0.042(15) Uiso 1 1 d . . . . .
H4B H -0.211(7) -0.692(5) 0.142(5) 0.011(10) Uiso 1 1 d . . . . .
H6B H -0.603(9) -0.560(7) -0.187(7) 0.041(15) Uiso 1 1 d . . . . .
H1 H 0.148(8) -0.870(7) 0.579(7) 0.028(13) 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
S1 C2 1.823(4) . ?
S1 C7 1.815(3) . ?
S5 C4 1.802(4) . ?
S5 C6 1.813(4) . ?
N3 C2 1.472(4) . ?
N3 C4 1.484(4) . ?
N3 C8 1.492(4) . ?
C10 C8 1.544(5) . ?
C10 H10A 0.96(6) . ?
C10 H10B 1.02(6) . ?
C10 H10C 0.93(6) . ?
O2 C9 1.217(4) . ?
C2 H2A 1.02(5) . ?
C2 H2B 1.02(4) . ?
C4 H4A 0.98(4) . ?
C4 H4B 1.00(4) . ?
C9 O1 1.316(4) . ?
C9 C8 1.528(5) . ?
O1 H1 0.90(6) . ?
C8 H8 0.95(5) . ?
C6 C7 1.520(5) . ?
C6 H6A 0.94(5) . ?
C6 H6B 0.95(6) . ?
C7 H7A 0.95(4) . ?
C7 H7B 0.91(5) . ?

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
C7 S1 C2 100.74(17) . . ?
C4 S5 C6 101.72(18) . . ?
C2 N3 C4 112.7(3) . . ?
C2 N3 C8 112.6(3) . . ?
C4 N3 C8 107.5(3) . . ?
C8 C10 H10A 112(3) . . ?
C8 C10 H10B 107(3) . . ?
C8 C10 H10C 98(4) . . ?
H10A C10 H10B 113(4) . . ?
H10A C10 H10C 110(5) . . ?
H10B C10 H10C 114(5) . . ?
S1 C2 H2A 105(3) . . ?
S1 C2 H2B 109(2) . . ?
N3 C2 S1 117.2(2) . . ?
N3 C2 H2A 109(3) . . ?
N3 C2 H2B 110(2) . . ?
H2A C2 H2B 106(4) . . ?
S5 C4 H4A 106(2) . . ?
S5 C4 H4B 104(2) . . ?
N3 C4 S5 115.8(3) . . ?
N3 C4 H4A 107(2) . . ?
N3 C4 H4B 112(2) . . ?
H4A C4 H4B 112(3) . . ?
O2 C9 O1 124.4(3) . . ?
O2 C9 C8 123.5(3) . . ?
O1 C9 C8 112.0(3) . . ?
C9 O1 H1 110(3) . . ?
N3 C8 C10 113.7(3) . . ?
N3 C8 C9 110.0(3) . . ?
N3 C8 H8 109(3) . . ?
C10 C8 H8 108(3) . . ?
C9 C8 C10 105.6(3) . . ?
C9 C8 H8 112(3) . . ?
S5 C6 H6A 107(3) . . ?
S5 C6 H6B 101(3) . . ?
C7 C6 S5 115.5(3) . . ?
C7 C6 H6A 108(3) . . ?
C7 C6 H6B 113(4) . . ?
H6A C6 H6B 112(4) . . ?
S1 C7 H7A 97(2) . . ?
S1 C7 H7B 109(3) . . ?
C6 C7 S1 114.9(3) . . ?
C6 C7 H7A 112(3) . . ?
C6 C7 H7B 110(3) . . ?
H7A C7 H7B 113(4) . . ?

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
S5 C6 C7 S1 64.0(4) . . . . ?
O2 C9 C8 N3 -31.8(5) . . . . ?
O2 C9 C8 C10 91.2(4) . . . . ?
C2 S1 C7 C6 -71.2(3) . . . . ?
C2 N3 C4 S5 -45.7(4) . . . . ?
C2 N3 C8 C10 58.6(4) . . . . ?
C2 N3 C8 C9 176.7(3) . . . . ?
C4 S5 C6 C7 -73.8(3) . . . . ?
C4 N3 C2 S1 -49.1(4) . . . . ?
C4 N3 C8 C10 -176.7(3) . . . . ?
C4 N3 C8 C9 -58.5(3) . . . . ?
O1 C9 C8 N3 150.1(3) . . . . ?
O1 C9 C8 C10 -86.8(4) . . . . ?
C8 N3 C2 S1 72.7(3) . . . . ?
C8 N3 C4 S5 -170.4(2) . . . . ?
C6 S5 C4 N3 94.8(3) . . . . ?
C7 S1 C2 N3 96.0(3) . . . . ?

_olex2_date_sample_data_collection 1393988609.55
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_2b
_database_code_depnum_ccdc_archive 'CCDC 1403635'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2016-05-12
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        '2-(1,5,3-dithiazepan-3-yl)acetic acid'
_chemical_formula_moiety         'C6 H11 N O2 S2, C2 H6 O S'
_chemical_formula_sum            'C8 H17 N O3 S3'
_chemical_formula_weight         271.41
_chemical_melting_point          ?
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.58182(17)
_cell_length_b                   16.4019(4)
_cell_length_c                   11.5843(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.923(3)
_cell_angle_gamma                90
_cell_volume                     1235.44(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2846
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      31.0395
_cell_measurement_theta_min      1.7759
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             576.0
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6313
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.109
_diffrn_reflns_theta_min         2.170
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   46.00   97.00   1.0000    5.1200
omega____ theta____ kappa____ phi______ frames
    -       24.2348  178.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00   63.00   1.0000    5.1200
omega____ theta____ kappa____ phi______ frames
    -       24.2348  -99.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   82.00   1.0000    5.1200
omega____ theta____ kappa____ phi______ frames
    -       24.2348    0.0000  150.0000 119
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0349587000
_diffrn_orient_matrix_UB_12      -0.0392469000
_diffrn_orient_matrix_UB_13      -0.0135335000
_diffrn_orient_matrix_UB_21      -0.0323918000
_diffrn_orient_matrix_UB_22      -0.0159359000
_diffrn_orient_matrix_UB_23      0.0511081000
_diffrn_orient_matrix_UB_31      -0.0981164000
_diffrn_orient_matrix_UB_32      -0.0087107000
_diffrn_orient_matrix_UB_33      -0.0323443000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3144
_reflns_number_total             3538
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+0.2249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0762
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.19260(5) 0.42558(2) 0.55893(3) 0.02480(9) Uani 1 1 d . . . . .
S1 S 0.92089(5) 0.71894(2) 1.03434(3) 0.02791(9) Uani 1 1 d . . . . .
S5 S 1.35105(5) 0.68578(2) 0.91232(3) 0.02691(9) Uani 1 1 d . . . . .
O1 O 0.63739(15) 0.50561(6) 0.81424(9) 0.0296(2) Uani 1 1 d . . . . .
N3 N 1.00111(16) 0.58530(7) 0.89658(10) 0.0217(2) Uani 1 1 d . . . . .
O2 O 0.56107(16) 0.59519(7) 0.66905(9) 0.0306(2) Uani 1 1 d . . . . .
C2 C 0.9347(2) 0.60904(8) 1.00400(12) 0.0227(3) Uani 1 1 d . . . . .
O1' O 0.23725(16) 0.51578(7) 0.57436(11) 0.0373(3) Uani 1 1 d . . . . .
C9 C 0.67935(19) 0.56495(8) 0.76206(11) 0.0216(2) Uani 1 1 d . . . . .
C8 C 0.8750(2) 0.61415(9) 0.79161(12) 0.0256(3) Uani 1 1 d . . . . .
C4 C 1.2189(2) 0.58692(9) 0.89677(14) 0.0266(3) Uani 1 1 d . . . . .
C7 C 1.1769(2) 0.74992(11) 1.09998(14) 0.0339(3) Uani 1 1 d . . . . .
C6 C 1.3565(2) 0.70222(10) 1.06681(13) 0.0285(3) Uani 1 1 d . . . . .
C1' C 0.4241(2) 0.37493(10) 0.61744(15) 0.0371(4) Uani 1 1 d . . . . .
H1'A H 0.5276 0.3862 0.5696 0.056 Uiso 1 1 calc R U . . .
H1'B H 0.4000 0.3172 0.6188 0.056 Uiso 1 1 calc R U . . .
H1'C H 0.4699 0.3940 0.6955 0.056 Uiso 1 1 calc R U . . .
C2' C 0.0439(3) 0.39999(12) 0.66842(16) 0.0464(4) Uani 1 1 d . . . . .
H2'A H 0.1171 0.4151 0.7436 0.070 Uiso 1 1 calc R U . . .
H2'B H 0.0186 0.3423 0.6668 0.070 Uiso 1 1 calc R U . . .
H2'C H -0.0848 0.4286 0.6543 0.070 Uiso 1 1 calc R U . . .
H2A H 1.019(3) 0.5825(11) 1.0683(16) 0.033(5) Uiso 1 1 d . . . . .
H4A H 1.286(2) 0.5531(11) 0.9588(14) 0.023(4) Uiso 1 1 d . . . . .
H2B H 0.790(3) 0.5927(11) 1.0026(14) 0.026(4) Uiso 1 1 d . . . . .
H6A H 1.479(3) 0.7308(11) 1.0866(15) 0.034(5) Uiso 1 1 d . . . . .
H4B H 1.248(3) 0.5646(11) 0.8256(16) 0.034(5) Uiso 1 1 d . . . . .
H2 H 0.458(3) 0.5669(13) 0.6469(18) 0.050(6) Uiso 1 1 d . . . . .
H7A H 1.186(3) 0.7466(14) 1.1812(19) 0.050(6) Uiso 1 1 d . . . . .
H6B H 1.362(3) 0.6488(12) 1.1024(15) 0.033(5) Uiso 1 1 d . . . . .
H7B H 1.192(3) 0.8039(15) 1.0763(18) 0.053(6) Uiso 1 1 d . . . . .
H8A H 0.839(2) 0.6684(11) 0.7959(14) 0.024(4) Uiso 1 1 d . . . . .
H8B H 0.948(3) 0.6087(12) 0.7298(16) 0.037(5) 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
S1' O1' 1.5136(12) . ?
S1' C1' 1.7750(14) . ?
S1' C2' 1.7688(17) . ?
S1 C2 1.8414(14) . ?
S1 C7 1.8105(15) . ?
S5 C4 1.8356(14) . ?
S5 C6 1.8047(15) . ?
O1 C9 1.2003(16) . ?
N3 C2 1.4353(18) . ?
N3 C8 1.4418(17) . ?
N3 C4 1.4334(17) . ?
O2 C9 1.3239(16) . ?
C9 C8 1.5132(18) . ?
C7 C6 1.516(2) . ?

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
O1' S1' C1' 105.84(7) . . ?
O1' S1' C2' 105.44(8) . . ?
C2' S1' C1' 98.79(9) . . ?
C7 S1 C2 106.54(7) . . ?
C6 S5 C4 99.53(7) . . ?
C2 N3 C8 115.42(11) . . ?
C4 N3 C2 115.64(11) . . ?
C4 N3 C8 116.10(12) . . ?
N3 C2 S1 117.50(10) . . ?
O1 C9 O2 124.16(12) . . ?
O1 C9 C8 124.94(12) . . ?
O2 C9 C8 110.89(12) . . ?
N3 C8 C9 111.97(11) . . ?
N3 C4 S5 118.37(10) . . ?
C6 C7 S1 117.40(11) . . ?
C7 C6 S5 115.61(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_8
_database_code_depnum_ccdc_archive 'CCDC 1403639'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2016-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
'3-(1,5,3-dithiazepan-3-yl)-2-phenylpropanoic acid'
_chemical_formula_moiety         'C13 H17 N O2 S2'
_chemical_formula_sum            'C13 H17 N O2 S2'
_chemical_formula_weight         283.40
_chemical_melting_point          ?
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.5874(4)
_cell_length_b                   10.2833(3)
_cell_length_c                   25.2185(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2745.64(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3587
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      31.0363
_cell_measurement_theta_min      1.9196
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200.0
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9252
_diffrn_reflns_theta_full        31.11
_diffrn_reflns_theta_max         31.11
_diffrn_reflns_theta_min         2.51
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -100.00  -64.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4536  178.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00    6.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4536   38.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega   11.00   91.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       24.2348   57.0000 -180.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0258746000
_diffrn_orient_matrix_UB_12      0.0124710000
_diffrn_orient_matrix_UB_13      -0.0254129000
_diffrn_orient_matrix_UB_21      -0.0605479000
_diffrn_orient_matrix_UB_22      0.0189167000
_diffrn_orient_matrix_UB_23      -0.0092949000
_diffrn_orient_matrix_UB_31      0.0125842000
_diffrn_orient_matrix_UB_32      0.0651520000
_diffrn_orient_matrix_UB_33      0.0076072000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3396
_reflns_number_total             3986
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3986
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+1.6551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1176
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.95759(4) 0.20692(5) 0.698733(18) 0.03191(13) Uani 1 d . . .
S5 S 0.77564(5) -0.06364(5) 0.739635(17) 0.03415(13) Uani 1 d . . .
O1 O 0.66109(11) 0.26246(11) 0.61587(5) 0.0254(2) Uani 1 d . . .
O2 O 0.85450(12) 0.30494(12) 0.58511(6) 0.0320(3) Uani 1 d . . .
N3 N 0.83294(12) 0.01701(13) 0.63801(5) 0.0211(3) Uani 1 d . . .
C8 C 0.78540(14) 0.08221(14) 0.58910(6) 0.0199(3) Uani 1 d . . .
C4 C 0.73320(16) 0.01652(17) 0.67893(6) 0.0237(3) Uani 1 d . . .
C16 C 0.77205(14) 0.22894(15) 0.59617(6) 0.0212(3) Uani 1 d . . .
C9 C 0.86836(17) 0.05059(17) 0.54154(7) 0.0271(3) Uani 1 d . . .
C2 C 0.95613(16) 0.06294(18) 0.65690(7) 0.0273(3) Uani 1 d . . .
C10 C 0.81398(17) 0.10006(17) 0.49012(7) 0.0281(3) Uani 1 d . . .
C15 C 0.8798(2) 0.1897(2) 0.46015(8) 0.0398(5) Uani 1 d . . .
C6 C 0.8247(2) 0.0750(2) 0.77893(7) 0.0394(5) Uani 1 d . . .
C7 C 0.9514(2) 0.1320(2) 0.76353(8) 0.0408(5) Uani 1 d . . .
C13 C 0.7178(3) 0.1875(3) 0.39415(10) 0.0635(8) Uani 1 d . . .
C12 C 0.6503(3) 0.1002(4) 0.42390(11) 0.0637(8) Uani 1 d . . .
C11 C 0.6986(2) 0.0541(3) 0.47186(9) 0.0461(5) Uani 1 d . . .
C14 C 0.8327(3) 0.2322(3) 0.41183(10) 0.0572(7) Uani 1 d . . .
H9A H 0.953(2) 0.091(2) 0.5465(9) 0.030(5) Uiso 1 d . . .
H2A H 1.006(2) 0.085(2) 0.6263(9) 0.034(6) Uiso 1 d . . .
H8 H 0.7020(18) 0.0487(18) 0.5839(8) 0.019(4) Uiso 1 d . . .
H2B H 0.996(2) -0.005(2) 0.6782(9) 0.035(6) Uiso 1 d . . .
H4A H 0.663(2) -0.029(2) 0.6660(8) 0.028(5) Uiso 1 d . . .
H4B H 0.706(2) 0.107(2) 0.6888(9) 0.033(6) Uiso 1 d . . .
H9B H 0.879(2) -0.043(2) 0.5395(8) 0.030(5) Uiso 1 d . . .
H7A H 1.015(3) 0.063(3) 0.7654(11) 0.058(8) Uiso 1 d . . .
H7B H 0.971(2) 0.203(2) 0.7858(10) 0.040(6) Uiso 1 d . . .
H6A H 0.829(2) 0.037(2) 0.8142(11) 0.047(7) Uiso 1 d . . .
H6B H 0.756(2) 0.140(2) 0.7783(9) 0.038(6) Uiso 1 d . . .
H15 H 0.961(2) 0.226(3) 0.4735(11) 0.050(7) Uiso 1 d . . .
H1 H 0.657(3) 0.348(3) 0.6247(12) 0.071(9) Uiso 1 d . . .
H11 H 0.653(2) -0.010(3) 0.4931(11) 0.054(7) Uiso 1 d . . .
H12 H 0.565(3) 0.066(3) 0.4147(13) 0.077(10) Uiso 1 d . . .
H13 H 0.686(3) 0.214(3) 0.3594(14) 0.080(10) Uiso 1 d . . .
H14 H 0.881(3) 0.303(4) 0.3917(16) 0.098(12) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.8181(18) . ?
S1 C7 1.808(2) . ?
S5 C4 1.7959(17) . ?
S5 C6 1.812(2) . ?
O1 C16 1.3213(19) . ?
O2 C16 1.2044(19) . ?
N3 C8 1.4914(19) . ?
N3 C4 1.476(2) . ?
N3 C2 1.467(2) . ?
C8 C16 1.526(2) . ?
C8 C9 1.522(2) . ?
C9 C10 1.507(2) . ?
C10 C15 1.380(3) . ?
C10 C11 1.388(3) . ?
C15 C14 1.387(3) . ?
C6 C7 1.515(3) . ?
C13 C12 1.371(5) . ?
C13 C14 1.375(4) . ?
C12 C11 1.396(3) . ?

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
C7 S1 C2 100.21(10) . . ?
C4 S5 C6 100.17(9) . . ?
C4 N3 C8 109.76(12) . . ?
C2 N3 C8 115.08(13) . . ?
C2 N3 C4 114.22(13) . . ?
N3 C8 C16 112.28(12) . . ?
N3 C8 C9 111.16(12) . . ?
C9 C8 C16 110.91(13) . . ?
N3 C4 S5 114.73(11) . . ?
O1 C16 C8 112.60(13) . . ?
O2 C16 O1 124.21(15) . . ?
O2 C16 C8 123.19(14) . . ?
C10 C9 C8 112.67(14) . . ?
N3 C2 S1 117.27(11) . . ?
C15 C10 C9 120.24(18) . . ?
C15 C10 C11 119.32(19) . . ?
C11 C10 C9 120.43(18) . . ?
C10 C15 C14 120.7(2) . . ?
C7 C6 S5 114.70(15) . . ?
C6 C7 S1 115.37(14) . . ?
C12 C13 C14 120.2(2) . . ?
C13 C12 C11 120.4(3) . . ?
C10 C11 C12 119.6(3) . . ?
C13 C14 C15 119.8(3) . . ?

_olex2_date_sample_data_collection 1386672494.92
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_7
_database_code_depnum_ccdc_archive 'CCDC 1403644'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2016-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-(+)-2-(1,5,3-dithiazepan-3-yl)-4-methylpentanoic acid'
_chemical_formula_moiety         'C10 H19 N O2 S2'
_chemical_formula_sum            'C10 H19 N O2 S2'
_chemical_formula_weight         249.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   10.6926(6)
_cell_length_b                   10.9871(7)
_cell_length_c                   21.4364(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2518.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    200.19(10)
_cell_measurement_theta_max      31.0486
_cell_measurement_theta_min      1.8498
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8525
_diffrn_reflns_theta_full        31.12
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_min         2.65
_diffrn_ambient_temperature      200.19(10)
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   80.00   1.0000   38.1400
omega____ theta____ kappa____ phi______ frames
    -       24.0786    0.0000   30.0000 126

#__ type_ start__ end____ width___ exp.time_
  2 omega   66.00   95.00   1.0000   38.1400
omega____ theta____ kappa____ phi______ frames
    -       24.0786 -178.0000   90.0000 29
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0186109000
_diffrn_orient_matrix_UB_12      -0.0247984000
_diffrn_orient_matrix_UB_13      0.0291064000
_diffrn_orient_matrix_UB_21      -0.0632762000
_diffrn_orient_matrix_UB_22      0.0136285000
_diffrn_orient_matrix_UB_23      -0.0070142000
_diffrn_orient_matrix_UB_31      -0.0068807000
_diffrn_orient_matrix_UB_32      -0.0580510000
_diffrn_orient_matrix_UB_33      -0.0140853000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5207
_reflns_number_total             6260
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0406P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4'(H4'A,H4'B), C9(H9A,H9B), C7'(H7'A,H7'B), C2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C13'(H13D,H13E,H13F), C11'(H11D,
 H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S -0.86449(8) -0.74233(7) -0.35474(4) 0.03107(18) Uani 1 d . . .
S5' S -0.15232(8) -0.53003(7) -0.38589(4) 0.0349(2) Uani 1 d . . .
S5 S -0.64007(9) -0.50768(7) -0.37072(4) 0.0375(2) Uani 1 d . . .
S1' S -0.31735(9) -0.26499(8) -0.34455(4) 0.0377(2) Uani 1 d . . .
O1' O -0.4092(2) -0.5734(2) -0.52008(13) 0.0391(6) Uani 1 d . . .
O1 O -0.6724(2) -0.3944(2) -0.52842(11) 0.0290(5) Uani 1 d . . .
O2' O -0.2024(2) -0.5924(2) -0.52588(11) 0.0303(5) Uani 1 d . . .
O2 O -0.8700(2) -0.4209(2) -0.50065(12) 0.0427(6) Uani 1 d . . .
N3' N -0.2455(2) -0.3411(2) -0.46151(12) 0.0223(5) Uani 1 d . . .
N3 N -0.7434(2) -0.6649(2) -0.46103(12) 0.0219(5) Uani 1 d . . .
C12 C -0.7686(3) -0.4620(3) -0.51464(14) 0.0231(6) Uani 1 d . . .
C4 C -0.6338(3) -0.6376(3) -0.42289(15) 0.0272(6) Uani 1 d . . .
C12' C -0.3068(3) -0.5290(3) -0.52260(13) 0.0238(6) Uani 1 d . . .
C4' C -0.1330(3) -0.3954(3) -0.43435(14) 0.0271(6) Uani 1 d . . .
H4'A H -0.0919 -0.3335 -0.4094 0.032 Uiso 1 calc . . R
H4'B H -0.0768 -0.4161 -0.4682 0.032 Uiso 1 calc . . R
C9 C -0.8392(3) -0.6514(3) -0.56712(13) 0.0281(6) Uani 1 d . . .
H9A H -0.9226 -0.6339 -0.5518 0.034 Uiso 1 calc . . R
H9B H -0.8295 -0.7391 -0.5681 0.034 Uiso 1 calc . . R
C8 C -0.7443(3) -0.5987(3) -0.52153(14) 0.0238(6) Uani 1 d . . .
C9' C -0.1994(3) -0.3522(3) -0.57546(15) 0.0284(7) Uani 1 d . . .
C10 C -0.8277(3) -0.6026(3) -0.63364(15) 0.0299(7) Uani 1 d . . .
C8' C -0.2858(3) -0.3904(3) -0.52266(14) 0.0238(6) Uani 1 d . . .
C2' C -0.3532(3) -0.3342(3) -0.41870(15) 0.0287(6) Uani 1 d . . .
C6 C -0.6920(4) -0.5825(4) -0.30009(17) 0.0409(9) Uani 1 d . . .
C11 C -0.9360(4) -0.6518(4) -0.67228(17) 0.0431(9) Uani 1 d . . .
H11A H -0.9348 -0.7391 -0.6713 0.065 Uiso 1 calc . . GR
H11B H -0.9278 -0.6243 -0.7146 0.065 Uiso 1 calc . . GR
H11C H -1.0136 -0.6229 -0.6553 0.065 Uiso 1 calc . . GR
C10' C -0.2483(3) -0.3799(3) -0.64040(15) 0.0316(7) Uani 1 d . . .
C7' C -0.2880(4) -0.3974(3) -0.29699(16) 0.0383(8) Uani 1 d . . .
H7'A H -0.2907 -0.3735 -0.2535 0.046 Uiso 1 calc . . R
H7'B H -0.3547 -0.4558 -0.3038 0.046 Uiso 1 calc . . R
C7 C -0.8272(3) -0.6219(4) -0.30024(17) 0.0381(8) Uani 1 d . . .
C13 C -0.7015(4) -0.6311(4) -0.66231(16) 0.0452(9) Uani 1 d . . .
H13A H -0.6372 -0.5893 -0.6395 0.068 Uiso 1 calc . . GR
H13B H -0.7006 -0.6047 -0.7050 0.068 Uiso 1 calc . . GR
H13C H -0.6867 -0.7172 -0.6605 0.068 Uiso 1 calc . . GR
C13' C -0.1524(4) -0.3431(3) -0.68850(16) 0.0458(10) Uani 1 d . . .
H13D H -0.1371 -0.2572 -0.6855 0.069 Uiso 1 calc . . GR
H13E H -0.1831 -0.3621 -0.7294 0.069 Uiso 1 calc . . GR
H13F H -0.0759 -0.3865 -0.6811 0.069 Uiso 1 calc . . GR
C6' C -0.1648(4) -0.4591(4) -0.30945(18) 0.0414(9) Uani 1 d . . .
C11' C -0.3728(4) -0.3148(4) -0.65296(18) 0.0579(12) Uani 1 d . . .
H11D H -0.4383 -0.3542 -0.6300 0.087 Uiso 1 calc . . GR
H11E H -0.3913 -0.3181 -0.6967 0.087 Uiso 1 calc . . GR
H11F H -0.3664 -0.2313 -0.6400 0.087 Uiso 1 calc . . GR
C2 C -0.8639(3) -0.6580(3) -0.42704(13) 0.0244(6) Uani 1 d . . .
H2A H -0.9298 -0.6892 -0.4537 0.029 Uiso 1 calc . . R
H2B H -0.8826 -0.5734 -0.4182 0.029 Uiso 1 calc . . R
H6'A H -0.154(4) -0.533(3) -0.2878(15) 0.041(10) Uiso 1 d . . .
H7A H -0.878(4) -0.556(3) -0.3068(15) 0.037(10) Uiso 1 d . . .
H10' H -0.263(3) -0.460(3) -0.6433(14) 0.032(9) Uiso 1 d . . .
H6'B H -0.099(4) -0.408(4) -0.3058(19) 0.056(13) Uiso 1 d . . .
H6A H -0.678(3) -0.512(3) -0.2676(15) 0.038(10) Uiso 1 d . . .
H6B H -0.636(4) -0.661(3) -0.2919(15) 0.041(10) Uiso 1 d . . .
H2'A H -0.393(3) -0.416(3) -0.4122(15) 0.037(10) Uiso 1 d . . .
H10 H -0.835(3) -0.520(3) -0.6306(13) 0.027(9) Uiso 1 d . . .
H1 H -0.701(4) -0.329(3) -0.5275(16) 0.035(11) Uiso 1 d . . .
H8 H -0.657(3) -0.607(2) -0.5352(10) 0.000(6) Uiso 1 d . . .
H9'A H -0.126(3) -0.397(3) -0.5688(14) 0.024(8) Uiso 1 d . . .
H8' H -0.369(3) -0.355(3) -0.5285(13) 0.018(8) Uiso 1 d . . .
H2' H -0.224(4) -0.670(4) -0.5309(18) 0.055(13) Uiso 1 d . . .
H7B H -0.838(4) -0.653(3) -0.2574(17) 0.054(12) Uiso 1 d . . .
H2'B H -0.415(3) -0.279(3) -0.4381(15) 0.032(9) Uiso 1 d . . .
H9'B H -0.184(3) -0.271(3) -0.5752(14) 0.032(9) Uiso 1 d . . .
H4A H -0.572(4) -0.621(3) -0.4503(16) 0.037(10) Uiso 1 d . . .
H4B H -0.620(3) -0.706(3) -0.3976(14) 0.024(8) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.809(4) . ?
S1 C2 1.805(3) . ?
S5' C4' 1.819(3) . ?
S5' C6' 1.819(4) . ?
S5 C4 1.815(3) . ?
S5 C6 1.810(4) . ?
S1' C2' 1.803(3) . ?
S1' C7' 1.804(4) . ?
O1' C12' 1.200(4) . ?
O1 C12 1.302(3) . ?
O2' C12' 1.318(4) . ?
O2 C12 1.212(4) . ?
N3' C4' 1.463(4) . ?
N3' C8' 1.482(4) . ?
N3' C2' 1.474(4) . ?
N3 C4 1.460(4) . ?
N3 C8 1.487(4) . ?
N3 C2 1.482(4) . ?
C12 C8 1.532(4) . ?
C12' C8' 1.540(4) . ?
C9 C8 1.523(4) . ?
C9 C10 1.528(4) . ?
C9' C8' 1.520(4) . ?
C9' C10' 1.518(5) . ?
C10 C11 1.522(5) . ?
C10 C13 1.516(5) . ?
C6 C7 1.509(5) . ?
C10' C13' 1.510(5) . ?
C10' C11' 1.535(5) . ?
C7' C6' 1.504(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C7 100.28(17) . . ?
C4' S5' C6' 100.04(17) . . ?
C6 S5 C4 99.76(16) . . ?
C2' S1' C7' 101.23(16) . . ?
C4' N3' C8' 116.2(2) . . ?
C4' N3' C2' 114.5(2) . . ?
C2' N3' C8' 110.0(2) . . ?
C4 N3 C8 113.2(2) . . ?
C4 N3 C2 114.3(2) . . ?
C2 N3 C8 113.5(2) . . ?
O1 C12 C8 113.8(2) . . ?
O2 C12 O1 123.4(3) . . ?
O2 C12 C8 122.7(3) . . ?
N3 C4 S5 118.5(2) . . ?
O1' C12' O2' 124.1(3) . . ?
O1' C12' C8' 122.4(3) . . ?
O2' C12' C8' 113.5(3) . . ?
N3' C4' S5' 117.7(2) . . ?
C8 C9 C10 114.4(3) . . ?
N3 C8 C12 113.3(2) . . ?
N3 C8 C9 112.2(2) . . ?
C9 C8 C12 108.7(3) . . ?
C10' C9' C8' 114.7(3) . . ?
C11 C10 C9 108.8(3) . . ?
C13 C10 C9 112.2(3) . . ?
C13 C10 C11 112.5(3) . . ?
N3' C8' C12' 113.8(2) . . ?
N3' C8' C9' 112.4(3) . . ?
C9' C8' C12' 111.2(2) . . ?
N3' C2' S1' 113.8(2) . . ?
C7 C6 S5 115.0(3) . . ?
C9' C10' C11' 111.5(3) . . ?
C13' C10' C9' 109.8(3) . . ?
C13' C10' C11' 110.2(3) . . ?
C6' C7' S1' 114.5(3) . . ?
C6 C7 S1 115.0(2) . . ?
C7' C6' S5' 114.6(3) . . ?
N3 C2 S1 113.51(19) . . ?

_olex2_date_sample_data_collection 1389245900.18
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_4
_database_code_depnum_ccdc_archive 'CCDC 1403648'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2016-03-28
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        '2-(1,5,3-dithiazepan-3-yl)butanoic acid'
_chemical_formula_moiety         'C8 H15 N O2 S2'
_chemical_formula_sum            'C8 H15 N O2 S2'
_chemical_formula_weight         221.33
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0968(3)
_cell_length_b                   6.7869(3)
_cell_length_c                   16.6360(10)
_cell_angle_alpha                78.801(5)
_cell_angle_beta                 87.344(5)
_cell_angle_gamma                69.141(5)
_cell_volume                     527.34(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2049
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.9914
_cell_measurement_theta_min      2.4919
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             236.0
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4589
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.061
_diffrn_reflns_theta_min         2.497
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -29.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -      -23.4536  154.0000  131.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega   10.00   83.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       24.0786   57.0000  150.0000 73

#__ type_ start__ end____ width___ exp.time_
  3 omega   37.00   78.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       24.0786 -121.0000   69.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega  -39.00   40.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       24.0786  -57.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega  -18.00   95.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       24.0786   19.0000   90.0000 113
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1371008000
_diffrn_orient_matrix_UB_12      0.0374676000
_diffrn_orient_matrix_UB_13      0.0156566000
_diffrn_orient_matrix_UB_21      -0.0579967000
_diffrn_orient_matrix_UB_22      0.0253979000
_diffrn_orient_matrix_UB_23      -0.0402698000
_diffrn_orient_matrix_UB_31      -0.0057248000
_diffrn_orient_matrix_UB_32      -0.1045469000
_diffrn_orient_matrix_UB_33      0.0048484000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2551
_reflns_number_total             3000
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1328
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.87256(10) 0.20006(6) 0.28546(2) 0.03445(15) Uani 1 1 d . . . . .
S5 S 0.81082(9) 0.59246(6) 0.39138(2) 0.03237(14) Uani 1 1 d . . . . .
N3 N 0.5261(3) 0.63433(18) 0.24418(7) 0.0235(3) Uani 1 1 d . . . . .
C10 C 0.3067(3) 0.9858(2) 0.10385(9) 0.0235(3) Uani 1 1 d . . . . .
C9 C 0.5928(3) 0.9296(2) 0.14232(9) 0.0253(3) Uani 1 1 d . . . . .
C8 C 0.7135(3) 0.6936(2) 0.18301(9) 0.0271(3) Uani 1 1 d . . . . .
C2 C 0.5343(4) 0.4181(2) 0.25378(11) 0.0295(3) Uani 1 1 d . . . . .
C4 C 0.5097(4) 0.7149(2) 0.31798(10) 0.0291(3) Uani 1 1 d . . . . .
C6 C 0.7541(5) 0.3465(3) 0.43607(10) 0.0384(4) Uani 1 1 d . . . . .
C7 C 0.8964(6) 0.1579(3) 0.39550(12) 0.0478(5) Uani 1 1 d . . . . .
H8A H 0.745(4) 0.601(3) 0.1408(12) 0.030(5) Uiso 1 1 d . . . . .
H4A H 0.486(5) 0.874(3) 0.3005(13) 0.035(5) Uiso 1 1 d . . . . .
H6A H 0.816(5) 0.311(3) 0.4872(15) 0.049(6) Uiso 1 1 d . . . . .
H7A H 0.813(6) 0.039(4) 0.4188(16) 0.062(7) Uiso 1 1 d . . . . .
H6B H 0.534(6) 0.388(4) 0.4354(16) 0.058(7) Uiso 1 1 d . . . . .
H7B H 1.117(9) 0.080(6) 0.401(2) 0.115(13) Uiso 1 1 d . . . . .
H9A H 0.727(4) 0.959(3) 0.0995(13) 0.037(5) Uiso 1 1 d . . . . .
H2A H 0.387(5) 0.389(4) 0.2923(15) 0.047(6) Uiso 1 1 d . . . . .
H9B H 0.569(4) 1.023(3) 0.1811(12) 0.032(5) Uiso 1 1 d . . . . .
H2B H 0.507(5) 0.387(3) 0.2030(14) 0.039(6) Uiso 1 1 d . . . . .
H8B H 0.900(4) 0.657(3) 0.2071(12) 0.035(5) Uiso 1 1 d . . . . .
H10A H 0.188(4) 0.963(3) 0.1419(12) 0.028(5) Uiso 1 1 d . . . . .
H10B H 0.312(5) 0.897(4) 0.0624(13) 0.041(6) Uiso 1 1 d . . . . .
O1 O 0.2846(3) 1.34929(17) 0.05829(8) 0.0376(3) Uani 1 1 d . . . . .
O2 O -0.0642(3) 1.25552(19) 0.02487(9) 0.0393(3) Uani 1 1 d . . . . .
C11 C 0.1775(3) 1.2139(2) 0.06031(8) 0.0216(3) Uani 1 1 d . . . . .
H2 H -0.118(6) 1.371(4) -0.0027(17) 0.054(7) Uiso 1 1 d . . . . .
H4B H 0.363(5) 0.698(3) 0.3520(14) 0.039(5) 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
S1 C2 1.8450(16) . ?
S1 C7 1.8001(19) . ?
S5 C4 1.8462(17) . ?
S5 C6 1.8066(19) . ?
N3 C8 1.4609(19) . ?
N3 C2 1.4306(18) . ?
N3 C4 1.426(2) . ?
C10 C9 1.509(2) . ?
C10 C11 1.4960(19) . ?
C9 C8 1.523(2) . ?
C6 C7 1.500(3) . ?
O1 C11 1.2193(18) . ?
O2 C11 1.3036(18) . ?

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
C7 S1 C2 106.66(10) . . ?
C6 S5 C4 99.42(9) . . ?
C2 N3 C8 115.44(12) . . ?
C4 N3 C8 115.26(13) . . ?
C4 N3 C2 115.87(13) . . ?
C11 C10 C9 114.71(12) . . ?
C10 C9 C8 111.46(12) . . ?
N3 C8 C9 111.95(12) . . ?
N3 C2 S1 117.60(11) . . ?
N3 C4 S5 118.46(11) . . ?
C7 C6 S5 116.15(15) . . ?
C6 C7 S1 118.07(13) . . ?
O1 C11 C10 123.85(13) . . ?
O1 C11 O2 122.81(13) . . ?
O2 C11 C10 113.34(12) . . ?

_olex2_date_sample_data_collection 2014-03-27
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_6
_database_code_depnum_ccdc_archive 'CCDC 1403653'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2016-03-28
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-(+)-2-(1,5,3-dithiazepan-3-yl)-3-hydroxypropanoic acid'
_chemical_formula_moiety         'C7 H13 N O3 S2'
_chemical_formula_sum            'C7 H13 N O3 S2'
_chemical_formula_weight         223.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?

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

_cell_length_a                   6.8616(11)
_cell_length_b                   8.8688(8)
_cell_length_c                   8.9458(10)
_cell_angle_alpha                66.923(10)
_cell_angle_beta                 70.122(13)
_cell_angle_gamma                85.373(10)
_cell_volume                     470.11(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2158
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.9270
_cell_measurement_theta_min      2.5140
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236.0
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4183
_diffrn_reflns_point_group_measured_fraction_full 0.638
_diffrn_reflns_point_group_measured_fraction_max 0.546
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.919
_diffrn_reflns_theta_min         2.501
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -60.00  -35.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      -23.4536 -178.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   46.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -       24.0786   82.0000  140.0000 51

#__ type_ start__ end____ width___ exp.time_
  3 omega   38.00   64.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -       24.0786  -99.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   97.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -       24.0786   38.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   93.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -       24.0786   77.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  6 omega  -48.00   64.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -       24.0786  -19.0000   90.0000 112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0288510000
_diffrn_orient_matrix_UB_12      0.0119821000
_diffrn_orient_matrix_UB_13      -0.0880862000
_diffrn_orient_matrix_UB_21      -0.0496962000
_diffrn_orient_matrix_UB_22      0.0751863000
_diffrn_orient_matrix_UB_23      -0.0170416000
_diffrn_orient_matrix_UB_31      0.0939471000
_diffrn_orient_matrix_UB_32      0.0422953000
_diffrn_orient_matrix_UB_33      -0.0180450000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_number_gt                2873
_reflns_number_total             3248
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.12(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3248
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      0.763
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1182
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.36517(14) 0.37079(11) 0.27600(11) 0.0322(2) Uani 1 1 d . . . . .
S1' S 0.48878(14) 0.81552(10) -0.83359(11) 0.0316(2) Uani 1 1 d . . . . .
S5' S 0.94067(16) 0.85946(14) -0.74918(15) 0.0400(3) Uani 1 1 d . . . . .
S5 S -0.07512(14) 0.35269(14) 0.16284(13) 0.0371(3) Uani 1 1 d . . . . .
O1' O 0.1573(6) 0.6276(5) -0.2603(4) 0.0379(8) Uani 1 1 d . . . . .
O2 O 0.6966(6) 0.5800(4) -0.3048(4) 0.0390(8) Uani 1 1 d . . . . .
H2 H 0.5953 0.5735 -0.3313 0.059 Uiso 1 1 calc R U . . .
N3 N 0.3489(5) 0.4051(4) -0.0407(4) 0.0211(6) Uani 1 1 d . . . . .
N3' N 0.5271(5) 0.7958(4) -0.5284(4) 0.0227(6) Uani 1 1 d . . . . .
C8' C 0.3362(6) 0.8835(4) -0.4749(5) 0.0242(7) Uani 1 1 d . . . . .
C8 C 0.5439(5) 0.3171(4) -0.0915(5) 0.0211(6) Uani 1 1 d . . . . .
C4' C 0.7090(7) 0.9203(5) -0.6252(6) 0.0319(8) Uani 1 1 d . . . . .
C4 C 0.1609(6) 0.2837(5) 0.0507(5) 0.0259(7) Uani 1 1 d . . . . .
O3' O 0.2428(5) 1.0734(4) -0.3428(4) 0.0406(7) Uani 1 1 d . . . . .
C2 C 0.3733(7) 0.4983(5) 0.0619(5) 0.0280(8) Uani 1 1 d . . . . .
C2' C 0.5072(7) 0.6953(4) -0.6247(5) 0.0281(8) Uani 1 1 d . . . . .
H2'A H 0.3846 0.6209 -0.5562 0.034 Uiso 1 1 calc R U . . .
H2'B H 0.6268 0.6293 -0.6384 0.034 Uiso 1 1 calc R U . . .
C9' C 0.1382(6) 0.7733(5) -0.3938(5) 0.0312(8) Uani 1 1 d . . . . .
C10 C 0.7285(6) 0.4417(4) -0.2100(5) 0.0242(7) Uani 1 1 d . . . . .
O3 O 0.9003(4) 0.3895(3) -0.2030(4) 0.0351(6) Uani 1 1 d . . . . .
O2' O 0.4720(8) 0.8922(5) -0.2657(6) 0.0586(11) Uani 1 1 d . . . . .
H2' H 0.4478 0.7924 -0.2222 0.088 Uiso 1 1 calc R U . . .
O1 O 0.4476(6) 0.3025(4) -0.3191(4) 0.0369(7) Uani 1 1 d . . . . .
H1 H 0.4437 0.2465 -0.3724 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0956(8) 0.3828(6) 0.3962(6) 0.0411(11) Uani 1 1 d . . . . .
C6' C 0.9077(8) 0.9293(7) -0.9578(6) 0.0469(12) Uani 1 1 d . . . . .
H6'A H 0.8593 1.0395 -0.9852 0.056 Uiso 1 1 calc R U . . .
H6'B H 1.0421 0.9354 -1.0442 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5166(6) 0.2094(5) -0.1809(5) 0.0278(7) Uani 1 1 d . . . . .
H9A H 0.6478 0.1645 -0.2232 0.033 Uiso 1 1 calc R U . . .
H9B H 0.4164 0.1186 -0.0993 0.033 Uiso 1 1 calc R U . . .
C7' C 0.7558(8) 0.8208(6) -0.9704(6) 0.0442(11) Uani 1 1 d . . . . .
H7'A H 0.8016 0.7097 -0.9396 0.053 Uiso 1 1 calc R U . . .
H7'B H 0.7605 0.8604 -1.0893 0.053 Uiso 1 1 calc R U . . .
C6 C -0.0575(8) 0.2855(6) 0.3769(6) 0.0439(11) Uani 1 1 d . . . . .
H6A H -0.1939 0.2887 0.4563 0.053 Uiso 1 1 calc R U . . .
H6B H -0.0209 0.1720 0.4116 0.053 Uiso 1 1 calc R U . . .
C10' C 0.3569(7) 0.9567(5) -0.3483(5) 0.0296(8) Uani 1 1 d . . . . .
H4'A H 0.648(7) 1.015(5) -0.700(6) 0.021(10) Uiso 1 1 d . . . . .
H2A H 0.507(8) 0.560(5) 0.007(7) 0.032(11) Uiso 1 1 d . . . . .
H4A H 0.199(8) 0.197(6) 0.129(7) 0.024(11) Uiso 1 1 d . . . . .
H4'B H 0.761(8) 0.925(6) -0.550(7) 0.030(12) Uiso 1 1 d . . . . .
H8' H 0.343(8) 0.974(6) -0.596(7) 0.033(12) Uiso 1 1 d . . . . .
H4B H 0.153(8) 0.246(6) -0.029(7) 0.032(12) Uiso 1 1 d . . . . .
H8 H 0.588(7) 0.242(5) -0.002(6) 0.022(10) Uiso 1 1 d . . . . .
H7A H 0.096(8) 0.323(6) 0.522(7) 0.037(12) Uiso 1 1 d . . . . .
H2B H 0.280(11) 0.572(8) 0.086(9) 0.061(17) Uiso 1 1 d . . . . .
H1' H 0.074(9) 0.576(7) -0.238(8) 0.042(15) Uiso 1 1 d . . . . .
H9'A H 0.025(8) 0.834(6) -0.334(7) 0.034(13) Uiso 1 1 d . . . . .
H9'B H 0.085(8) 0.762(6) -0.490(7) 0.041(13) Uiso 1 1 d . . . . .
H7B H 0.076(9) 0.508(7) 0.365(8) 0.050(15) 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
S1 C2 1.786(4) . ?
S1 C7 1.815(5) . ?
S1' C2' 1.795(4) . ?
S1' C7' 1.817(5) . ?
S5' C4' 1.783(5) . ?
S5' C6' 1.810(5) . ?
S5 C4 1.794(4) . ?
S5 C6 1.813(5) . ?
O1' C9' 1.408(5) . ?
O2 C10 1.240(5) . ?
N3 C8 1.517(5) . ?
N3 C4 1.520(4) . ?
N3 C2 1.507(5) . ?
N3' C8' 1.500(5) . ?
N3' C4' 1.505(5) . ?
N3' C2' 1.502(5) . ?
C8' C9' 1.522(5) . ?
C8' C10' 1.557(5) . ?
C8 C10 1.531(5) . ?
C8 C9 1.522(5) . ?
O3' C10' 1.252(5) . ?
C10 O3 1.244(5) . ?
O2' C10' 1.220(6) . ?
O1 C9 1.403(5) . ?
C7 C6 1.505(8) . ?
C6' C7' 1.534(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C7 100.5(2) . . ?
C2' S1' C7' 100.7(2) . . ?
C4' S5' C6' 101.9(2) . . ?
C4 S5 C6 101.6(2) . . ?
C8 N3 C4 109.7(3) . . ?
C2 N3 C8 110.4(3) . . ?
C2 N3 C4 114.1(3) . . ?
C8' N3' C4' 108.0(3) . . ?
C8' N3' C2' 113.8(3) . . ?
C2' N3' C4' 113.6(3) . . ?
N3' C8' C9' 112.6(3) . . ?
N3' C8' C10' 109.7(3) . . ?
C9' C8' C10' 110.4(3) . . ?
N3 C8 C10 110.2(3) . . ?
N3 C8 C9 111.5(3) . . ?
C9 C8 C10 109.7(3) . . ?
N3' C4' S5' 116.6(3) . . ?
N3 C4 S5 116.3(3) . . ?
N3 C2 S1 114.1(2) . . ?
N3' C2' S1' 113.9(2) . . ?
O1' C9' C8' 110.2(3) . . ?
O2 C10 C8 118.9(4) . . ?
O2 C10 O3 126.4(4) . . ?
O3 C10 C8 114.7(3) . . ?
C6 C7 S1 114.6(3) . . ?
C7' C6' S5' 114.8(3) . . ?
O1 C9 C8 109.8(3) . . ?
C6' C7' S1' 114.1(3) . . ?
C7 C6 S5 116.1(3) . . ?
O3' C10' C8' 112.9(4) . . ?
O2' C10' C8' 117.8(4) . . ?
O2' C10' O3' 129.3(4) . . ?

_olex2_date_sample_data_collection 2014-10-27
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1403859'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2016-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        '3-(1,5,3-dithiazepan-3-yl)propanoic acid'
_chemical_formula_moiety         'C7 H12 N O2 S2'
_chemical_formula_sum            'C7 H12 N O2 S2'
_chemical_formula_weight         206.30
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.9212(5)
_cell_length_b                   30.519(2)
_cell_length_c                   6.7336(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.709(8)
_cell_angle_gamma                90
_cell_volume                     982.53(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1205
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      31.1397
_cell_measurement_theta_min      1.9978
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             436.0
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.878
_diffrn_reflns_Laue_measured_fraction_max 0.717
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3485
_diffrn_reflns_point_group_measured_fraction_full 0.878
_diffrn_reflns_point_group_measured_fraction_max 0.717
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.210
_diffrn_reflns_theta_min         2.670
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   59.00   98.00   1.0000   11.2700
omega____ theta____ kappa____ phi______ frames
    -       24.0786  178.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   62.00   1.0000   11.2700
omega____ theta____ kappa____ phi______ frames
    -       24.0786  -19.0000  -60.0000 111

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00   -5.00   1.0000   11.2700
omega____ theta____ kappa____ phi______ frames
    -       24.0786  -99.0000 -101.0000 2
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0148444000
_diffrn_orient_matrix_UB_12      -0.0146958000
_diffrn_orient_matrix_UB_13      -0.0784075000
_diffrn_orient_matrix_UB_21      0.0509083000
_diffrn_orient_matrix_UB_22      -0.0163258000
_diffrn_orient_matrix_UB_23      0.0744052000
_diffrn_orient_matrix_UB_31      -0.1385986000
_diffrn_orient_matrix_UB_32      -0.0075663000
_diffrn_orient_matrix_UB_33      -0.0085488000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1850
_reflns_number_total             2291
_reflns_odcompleteness_completeness 81.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+0.6655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1448
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Others
 Sof(H6B)=Sof(C7B)=Sof(H7BA)=Sof(H7BB)=1-FVAR(1)
 Sof(H6A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C8(H8A,H8B), C4(H4A,H4B), C7A(H7AA,H7AB), C7B(H7BA,
 H7BB)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.31021(19) 0.13346(3) 0.23197(11) 0.0569(3) Uani 1 1 d . . . . .
S5 S 0.50682(19) 0.19991(2) 0.63190(14) 0.0534(3) Uani 1 1 d . . . . .
O1 O 0.7709(5) 0.04621(6) 1.0097(3) 0.0436(5) Uani 1 1 d . . . . .
O2 O 0.7756(4) -0.00577(6) 0.7816(3) 0.0414(5) Uani 1 1 d . . . . .
C10 C 0.6683(5) 0.02665(7) 0.8365(3) 0.0286(5) Uani 1 1 d . . . . .
N3 N 0.6451(4) 0.11126(6) 0.6162(3) 0.0296(5) Uani 1 1 d . . . . .
C2 C 0.6007(6) 0.10514(8) 0.3992(4) 0.0345(6) Uani 1 1 d . . . . .
H2A H 0.5763 0.0740 0.3717 0.041 Uiso 1 1 calc R . . . .
H2B H 0.7705 0.1139 0.3606 0.041 Uiso 1 1 calc R . . . .
C9 C 0.4059(6) 0.04638(9) 0.7109(4) 0.0373(6) Uani 1 1 d . . . . .
H9A H 0.2503 0.0377 0.7676 0.045 Uiso 1 1 calc R . . . .
H9B H 0.3721 0.0348 0.5731 0.045 Uiso 1 1 calc R . . . .
C8 C 0.4161(6) 0.09597(8) 0.7017(4) 0.0346(6) Uani 1 1 d . . . . .
H8A H 0.2403 0.1068 0.6185 0.042 Uiso 1 1 calc R . . . .
H8B H 0.4387 0.1078 0.8383 0.042 Uiso 1 1 calc R . . . .
C4 C 0.7476(6) 0.15349(9) 0.6890(4) 0.0419(6) Uani 1 1 d . . . . .
H4A H 0.9080 0.1600 0.6336 0.050 Uiso 1 1 calc R . . . .
H4B H 0.8146 0.1517 0.8364 0.050 Uiso 1 1 calc R . . . .
C6 C 0.5489(14) 0.21483(18) 0.3839(9) 0.0896(17) Uani 1 1 d . . . . .
H6A H 0.47(3) 0.240(5) 0.361(19) 0.107 Uiso 0.44(3) 1 d R . P A 2
H6B H 0.64(2) 0.236(4) 0.394(16) 0.107 Uiso 0.56(3) 1 d R . P A 3
C7A C 0.374(6) 0.1843(4) 0.1890(18) 0.052(4) Uani 0.44(3) 1 d . . P A 2
H7AA H 0.1963 0.1986 0.1330 0.062 Uiso 0.44(3) 1 calc R . P A 2
H7AB H 0.4783 0.1848 0.0835 0.062 Uiso 0.44(3) 1 calc R . P A 2
C7B C 0.525(6) 0.1895(4) 0.238(2) 0.070(4) Uani 0.56(3) 1 d . . P A 3
H7BA H 0.7117 0.1818 0.2269 0.084 Uiso 0.56(3) 1 calc R . P A 3
H7BB H 0.4382 0.2058 0.1154 0.084 Uiso 0.56(3) 1 calc R . P A 3
H1 H 0.922(8) 0.0343(12) 1.081(6) 0.062(11) 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
S1 C2 1.816(3) . ?
S1 C7A 1.622(13) . ?
S1 C7B 2.005(19) . ?
S5 C4 1.829(3) . ?
S5 C6 1.789(5) . ?
O1 C10 1.301(3) . ?
O1 H1 0.86(4) . ?
O2 C10 1.219(3) . ?
C10 C9 1.492(4) . ?
N3 C2 1.437(3) . ?
N3 C8 1.458(3) . ?
N3 C4 1.428(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.516(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6A 0.87(13) . ?
C6 H6B 0.79(11) . ?
C6 C7A 1.673(19) . ?
C6 C7B 1.234(16) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C7B 93.5(7) . . ?
C7A S1 C2 114.1(9) . . ?
C6 S5 C4 100.4(2) . . ?
C10 O1 H1 114(2) . . ?
O1 C10 C9 115.0(2) . . ?
O2 C10 O1 122.7(2) . . ?
O2 C10 C9 122.3(2) . . ?
C2 N3 C8 114.5(2) . . ?
C4 N3 C2 115.0(2) . . ?
C4 N3 C8 113.4(2) . . ?
S1 C2 H2A 107.7 . . ?
S1 C2 H2B 107.7 . . ?
N3 C2 S1 118.44(17) . . ?
N3 C2 H2A 107.7 . . ?
N3 C2 H2B 107.7 . . ?
H2A C2 H2B 107.1 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C10 C9 C8 113.2(2) . . ?
H9A C9 H9B 107.8 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
N3 C8 C9 111.8(2) . . ?
N3 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
S5 C4 H4A 107.8 . . ?
S5 C4 H4B 107.8 . . ?
N3 C4 S5 117.9(2) . . ?
N3 C4 H4A 107.8 . . ?
N3 C4 H4B 107.8 . . ?
H4A C4 H4B 107.2 . . ?
S5 C6 H6A 105(9) . . ?
S5 C6 H6B 109(8) . . ?
C7A C6 S5 116.0(5) . . ?
C7A C6 H6A 104(9) . . ?
C7B C6 S5 125.0(5) . . ?
C7B C6 H6B 121(8) . . ?
S1 C7A C6 118.6(7) . . ?
S1 C7A H7AA 107.7 . . ?
S1 C7A H7AB 107.7 . . ?
C6 C7A H7AA 107.7 . . ?
C6 C7A H7AB 107.7 . . ?
H7AA C7A H7AB 107.1 . . ?
S1 C7B H7BA 107.3 . . ?
S1 C7B H7BB 107.3 . . ?
C6 C7B S1 120.1(7) . . ?
C6 C7B H7BA 107.3 . . ?
C6 C7B H7BB 107.3 . . ?
H7BA C7B H7BB 106.9 . . ?

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
S5 C6 C7A S1 -29.1(17) . . . . ?
S5 C6 C7B S1 21(2) . . . . ?
O1 C10 C9 C8 44.2(3) . . . . ?
O2 C10 C9 C8 -136.8(2) . . . . ?
C10 C9 C8 N3 59.0(3) . . . . ?
C2 S1 C7A C6 -41.6(15) . . . . ?
C2 N3 C8 C9 73.5(3) . . . . ?
C2 N3 C4 S5 72.1(3) . . . . ?
C8 N3 C2 S1 62.6(3) . . . . ?
C8 N3 C4 S5 -62.3(3) . . . . ?
C4 S5 C6 C7A 79.6(8) . . . . ?
C4 S5 C6 C7B 52.9(15) . . . . ?
C4 N3 C2 S1 -71.3(3) . . . . ?
C4 N3 C8 C9 -151.9(2) . . . . ?
C6 S5 C4 N3 -85.6(3) . . . . ?
C7A S1 C2 N3 80.9(5) . . . . ?
C7A C6 C7B S1 -55.2(15) . . . . ?
C7B S1 C2 N3 82.6(3) . . . . ?
C7B S1 C7A C6 -46.4(14) . . . . ?
C7B C6 C7A S1 88.7(19) . . . . ?

_olex2_date_sample_data_collection 1384406396.26
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_2a
_database_code_depnum_ccdc_archive 'CCDC 1403867'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2016-05-12
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        '2-(1,5,3-dithiazepan-3-yl)acetic acid'
_chemical_formula_moiety         'C6 H11 N O2 S2, H2 O'
_chemical_formula_sum            'C6 H13 N O3 S2'
_chemical_formula_weight         211.29
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.6882(3)
_cell_length_b                   8.6039(4)
_cell_length_c                   8.0793(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.507(5)
_cell_angle_gamma                90
_cell_volume                     463.48(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1280
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      31.1197
_cell_measurement_theta_min      2.5237
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             224.0
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0084
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2436
_diffrn_reflns_point_group_measured_fraction_full 0.840
_diffrn_reflns_point_group_measured_fraction_max 0.684
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.189
_diffrn_reflns_theta_min         3.055
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   50.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -       24.2348  -38.0000  -30.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   53.00   96.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -       24.2348  178.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -19.00   67.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -       24.2348  -19.0000   30.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0231131000
_diffrn_orient_matrix_UB_12      -0.0627213000
_diffrn_orient_matrix_UB_13      -0.0553230000
_diffrn_orient_matrix_UB_21      -0.0910382000
_diffrn_orient_matrix_UB_22      -0.0126711000
_diffrn_orient_matrix_UB_23      0.0374140000
_diffrn_orient_matrix_UB_31      -0.0499039000
_diffrn_orient_matrix_UB_32      0.0520848000
_diffrn_orient_matrix_UB_33      -0.0573142000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.462
_reflns_Friedel_fraction_full    0.677
_reflns_Friedel_fraction_max     0.459
_reflns_number_gt                1990
_reflns_number_total             2054
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 626 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.13(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      0.752
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0888
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.49076(8) -0.52899(7) -0.58966(7) 0.02430(16) Uani 1 1 d . . . . .
S5 S -0.96115(9) -0.59110(8) -0.42915(7) 0.02582(16) Uani 1 1 d . . . . .
N3 N -0.8601(3) -0.5973(3) -0.7571(2) 0.0170(3) Uani 1 1 d . . . . .
O2 O -1.3455(3) -0.5793(3) -0.9965(3) 0.0297(4) Uani 1 1 d . . . . .
H2 H -1.4179 -0.6466 -1.0413 0.045 Uiso 1 1 calc R U . . .
C8 C -1.0429(3) -0.5239(3) -0.8419(3) 0.0198(4) Uani 1 1 d . . . . .
O3 O -1.3382(3) -0.2683(2) -1.0409(3) 0.0272(4) Uani 1 1 d G . . . .
H3A H -1.2287 -0.2257 -1.0628 0.041 Uiso 1 1 d G U . . .
H3B H -1.3221 -0.3662 -1.0344 0.041 Uiso 1 1 d G U . . .
C2 C -0.7082(3) -0.4697(3) -0.7166(3) 0.0203(4) Uani 1 1 d . . . . .
C4 C -0.9041(4) -0.6950(3) -0.6112(3) 0.0203(4) Uani 1 1 d . . . . .
C9 C -1.1911(3) -0.6422(3) -0.9242(3) 0.0205(4) Uani 1 1 d . . . . .
O1 O -1.1536(3) -0.7821(2) -0.9149(2) 0.0274(4) Uani 1 1 d . . . . .
C6 C -0.7167(4) -0.5875(4) -0.3154(3) 0.0296(5) Uani 1 1 d . . . . .
C7 C -0.5636(4) -0.4817(4) -0.3846(3) 0.0285(5) Uani 1 1 d . . . . .
H4A H -1.010(6) -0.761(5) -0.647(5) 0.031(9) Uiso 1 1 d . . . . .
H8A H -1.096(5) -0.464(4) -0.774(4) 0.022(8) Uiso 1 1 d . . . . .
H4B H -0.794(5) -0.763(4) -0.599(4) 0.020(7) Uiso 1 1 d . . . . .
H6A H -0.644(6) -0.692(5) -0.329(5) 0.036(10) Uiso 1 1 d . . . . .
H7A H -0.568(7) -0.365(7) -0.406(6) 0.063(16) Uiso 1 1 d . . . . .
H2A H -0.673(5) -0.434(4) -0.817(4) 0.014(7) Uiso 1 1 d . . . . .
H6B H -0.748(6) -0.559(6) -0.232(6) 0.043(11) Uiso 1 1 d . . . . .
H8B H -0.975(5) -0.461(5) -0.941(4) 0.028(9) Uiso 1 1 d . . . . .
H7B H -0.425(5) -0.487(5) -0.316(4) 0.030(9) Uiso 1 1 d . . . . .
H2B H -0.749(5) -0.387(4) -0.657(4) 0.014(7) 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
S1 C2 1.787(2) . ?
S1 C7 1.809(3) . ?
S5 C4 1.787(2) . ?
S5 C6 1.812(3) . ?
N3 C8 1.494(3) . ?
N3 C2 1.514(3) . ?
N3 C4 1.496(3) . ?
O2 C9 1.267(3) . ?
C8 C9 1.536(3) . ?
C9 O1 1.230(3) . ?
C6 C7 1.510(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
C2 S1 C7 101.28(12) . . ?
C4 S5 C6 100.58(13) . . ?
C8 N3 C2 107.7(2) . . ?
C8 N3 C4 113.24(16) . . ?
C4 N3 C2 114.00(18) . . ?
N3 C8 C9 113.3(2) . . ?
N3 C2 S1 114.80(17) . . ?
N3 C4 S5 115.83(16) . . ?
O2 C9 C8 113.0(2) . . ?
O1 C9 O2 126.9(2) . . ?
O1 C9 C8 120.1(2) . . ?
C7 C6 S5 115.7(2) . . ?
C6 C7 S1 116.3(2) . . ?

_olex2_date_sample_data_collection 1386301073.56
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
