# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_5a_VHQAU
_database_code_depnum_ccdc_archive 'CCDC 1826226'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H19 N3 O3 S'
_chemical_formula_sum            'C12 H19 N3 O3 S'
_chemical_formula_weight         285.36

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

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

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

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

_cell_length_a                   7.6720(11)
_cell_length_b                   9.7977(13)
_cell_length_c                   9.9187(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.011(5)
_cell_angle_gamma                90
_cell_volume                     745.57(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2545
_cell_measurement_theta_min      2.053
_cell_measurement_theta_max      27.364

_exptl_crystal_description       rod
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.60
_diffrn_reflns_number            6038
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         27.364
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3186
_reflns_number_gt                2857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_max     0.889
_reflns_Friedel_fraction_full    0.960

_reflns_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 >
σ(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.
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+0.0208P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3186
_refine_ls_number_parameters     215
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.0158(3) 0.1348(3) 0.1766(2) 0.0614(6) Uani 1 1 d . . . . .
C1 C 0.4576(3) 0.2120(3) -0.0381(3) 0.0391(6) Uani 1 1 d . . . . .
O1 O 0.5406(3) 0.3183(2) -0.0494(3) 0.0543(6) Uani 1 1 d . . . . .
N2 N 0.5332(3) 0.0942(2) -0.0100(3) 0.0428(5) Uani 1 1 d . . . . .
H2 H 0.477(6) 0.019(5) -0.003(5) 0.086(14) Uiso 1 1 d . . . . .
N3 N 0.7155(3) 0.0836(3) 0.0075(4) 0.0527(7) Uani 1 1 d . . . . .
H3A H 0.752(6) 0.131(5) -0.047(5) 0.080(15) Uiso 1 1 d . . . . .
H3B H 0.741(6) 0.107(5) 0.088(5) 0.076(14) Uiso 1 1 d . . . . .
C4 C 0.2589(3) 0.2088(3) -0.0577(3) 0.0376(5) Uani 1 1 d . . . . .
H4 H 0.218(3) 0.122(3) -0.039(3) 0.028(6) Uiso 1 1 d . . . . .
C41 C 0.2136(4) 0.2533(4) -0.2026(3) 0.0471(6) Uani 1 1 d . . . . .
H41 H 0.254(4) 0.340(4) -0.209(3) 0.046(8) Uiso 1 1 d . . . . .
C42 C 0.3009(6) 0.1607(5) -0.3050(4) 0.0749(11) Uani 1 1 d . . . . .
H42A H 0.2650 0.0681 -0.2898 0.112 Uiso 1 1 calc R U . . .
H42B H 0.4251 0.1673 -0.2957 0.112 Uiso 1 1 calc R U . . .
H42C H 0.2677 0.1881 -0.3944 0.112 Uiso 1 1 calc R U . . .
C43 C 0.0177(4) 0.2553(5) -0.2260(3) 0.0637(8) Uani 1 1 d . . . . .
H43A H -0.0063 0.2892 -0.3149 0.096 Uiso 1 1 calc R U . . .
H43B H -0.0367 0.3134 -0.1605 0.096 Uiso 1 1 calc R U . . .
H43C H -0.0277 0.1644 -0.2175 0.096 Uiso 1 1 calc R U . . .
N5 N 0.1761(3) 0.3012(2) 0.0384(2) 0.0386(5) Uani 1 1 d . . . . .
H5 H 0.206(4) 0.376(4) 0.030(4) 0.049(10) Uiso 1 1 d . . . . .
S6 S 0.12359(7) 0.25384(8) 0.18839(6) 0.0444(2) Uani 1 1 d . . . . .
O7 O 0.0571(3) 0.3733(3) 0.2543(3) 0.0671(7) Uani 1 1 d . . . . .
C9 C 0.3161(3) 0.2007(3) 0.2722(3) 0.0407(6) Uani 1 1 d . . . . .
C10 C 0.3360(5) 0.0668(3) 0.3115(3) 0.0517(7) Uani 1 1 d . . . . .
H10 H 0.254(5) 0.010(4) 0.293(4) 0.058(10) Uiso 1 1 d . . . . .
C11 C 0.4871(5) 0.0262(4) 0.3749(3) 0.0580(8) Uani 1 1 d . . . . .
H11 H 0.498(5) -0.064(5) 0.396(4) 0.073(12) Uiso 1 1 d . . . . .
C12 C 0.6222(4) 0.1172(4) 0.3988(3) 0.0531(8) Uani 1 1 d . . . . .
C121 C 0.7867(5) 0.0708(6) 0.4688(4) 0.0812(12) Uani 1 1 d . . . . .
H12A H 0.8852 0.0879 0.4116 0.122 Uiso 1 1 calc R U . . .
H12B H 0.7792 -0.0252 0.4876 0.122 Uiso 1 1 calc R U . . .
H12C H 0.8003 0.1201 0.5518 0.122 Uiso 1 1 calc R U . . .
C13 C 0.6021(4) 0.2512(5) 0.3560(3) 0.0578(7) Uani 1 1 d . . . . .
H13 H 0.675(5) 0.324(4) 0.380(4) 0.071(11) Uiso 1 1 d . . . . .
C14 C 0.4496(4) 0.2935(3) 0.2933(3) 0.0509(7) Uani 1 1 d . . . . .
H14 H 0.430(5) 0.374(5) 0.261(4) 0.073(12) 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
O8 S6 1.434(2) . ?
C1 O1 1.226(3) . ?
C1 N2 1.321(3) . ?
C1 C4 1.537(3) . ?
N2 N3 1.413(3) . ?
N2 H2 0.85(5) . ?
N3 H3A 0.77(5) . ?
N3 H3B 0.85(4) . ?
C4 N5 1.460(3) . ?
C4 C41 1.541(4) . ?
C4 H4 0.92(3) . ?
C41 C42 1.518(4) . ?
C41 C43 1.521(4) . ?
C41 H41 0.91(4) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
N5 S6 1.610(2) . ?
N5 H5 0.77(4) . ?
S6 O7 1.434(2) . ?
S6 C9 1.772(3) . ?
C9 C10 1.378(5) . ?
C9 C14 1.386(4) . ?
C10 C11 1.377(5) . ?
C10 H10 0.86(4) . ?
C11 C12 1.387(5) . ?
C11 H11 0.91(5) . ?
C12 C13 1.389(6) . ?
C12 C121 1.510(5) . ?
C121 H12A 0.9600 . ?
C121 H12B 0.9600 . ?
C121 H12C 0.9600 . ?
C13 C14 1.388(5) . ?
C13 H13 0.94(4) . ?
C14 H14 0.86(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
O1 C1 N2 122.3(2) . . ?
O1 C1 C4 121.4(2) . . ?
N2 C1 C4 116.4(2) . . ?
C1 N2 N3 121.6(2) . . ?
C1 N2 H2 123(3) . . ?
N3 N2 H2 116(3) . . ?
N2 N3 H3A 103(3) . . ?
N2 N3 H3B 109(3) . . ?
H3A N3 H3B 115(5) . . ?
N5 C4 C1 109.6(2) . . ?
N5 C4 C41 109.6(2) . . ?
C1 C4 C41 109.6(2) . . ?
N5 C4 H4 106.8(16) . . ?
C1 C4 H4 109.1(17) . . ?
C41 C4 H4 112.1(17) . . ?
C42 C41 C43 110.0(3) . . ?
C42 C41 C4 110.8(3) . . ?
C43 C41 C4 111.6(2) . . ?
C42 C41 H41 111(2) . . ?
C43 C41 H41 108(2) . . ?
C4 C41 H41 105(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C4 N5 S6 122.3(2) . . ?
C4 N5 H5 113(3) . . ?
S6 N5 H5 116(3) . . ?
O8 S6 O7 119.72(14) . . ?
O8 S6 N5 107.68(14) . . ?
O7 S6 N5 105.95(15) . . ?
O8 S6 C9 106.23(14) . . ?
O7 S6 C9 108.81(14) . . ?
N5 S6 C9 108.01(12) . . ?
C10 C9 C14 120.0(3) . . ?
C10 C9 S6 120.3(2) . . ?
C14 C9 S6 119.6(2) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 122(3) . . ?
C9 C10 H10 118(3) . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 118(3) . . ?
C12 C11 H11 121(3) . . ?
C11 C12 C13 118.2(3) . . ?
C11 C12 C121 120.6(4) . . ?
C13 C12 C121 121.2(4) . . ?
C12 C121 H12A 109.5 . . ?
C12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
C12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 113(3) . . ?
C12 C13 H13 126(3) . . ?
C9 C14 C13 119.6(3) . . ?
C9 C14 H14 115(3) . . ?
C13 C14 H14 126(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N2 N3 -0.7(5) . . . . ?
C4 C1 N2 N3 178.7(3) . . . . ?
O1 C1 C4 N5 -58.8(4) . . . . ?
N2 C1 C4 N5 121.9(3) . . . . ?
O1 C1 C4 C41 61.5(4) . . . . ?
N2 C1 C4 C41 -117.8(3) . . . . ?
N5 C4 C41 C42 178.9(3) . . . . ?
C1 C4 C41 C42 58.5(3) . . . . ?
N5 C4 C41 C43 -58.2(4) . . . . ?
C1 C4 C41 C43 -178.6(3) . . . . ?
C1 C4 N5 S6 -87.0(3) . . . . ?
C41 C4 N5 S6 152.7(2) . . . . ?
C4 N5 S6 O8 -54.4(2) . . . . ?
C4 N5 S6 O7 176.3(2) . . . . ?
C4 N5 S6 C9 59.9(2) . . . . ?
O8 S6 C9 C10 -0.1(3) . . . . ?
O7 S6 C9 C10 130.0(2) . . . . ?
N5 S6 C9 C10 -115.4(2) . . . . ?
O8 S6 C9 C14 177.4(2) . . . . ?
O7 S6 C9 C14 -52.5(3) . . . . ?
N5 S6 C9 C14 62.1(3) . . . . ?
C14 C9 C10 C11 1.6(5) . . . . ?
S6 C9 C10 C11 179.1(2) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 C121 179.8(3) . . . . ?
C11 C12 C13 C14 1.2(5) . . . . ?
C121 C12 C13 C14 -179.1(3) . . . . ?
C10 C9 C14 C13 -0.9(5) . . . . ?
S6 C9 C14 C13 -178.4(2) . . . . ?
C12 C13 C14 C9 -0.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.85(5) 2.04(5) 2.823(3) 152(5) 2_645
N3 H3B O8 0.85(4) 2.30(4) 2.894(4) 127(4) 1_655
N5 H5 N3 0.77(4) 2.15(4) 2.925(4) 176(4) 2_655

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.036

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

data_5b_LHQAU
_database_code_depnum_ccdc_archive 'CCDC 1826227'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H21 N3 O3 S'
_chemical_formula_sum            'C13 H21 N3 O3 S'
_chemical_formula_weight         299.39

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

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

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

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

_cell_length_a                   10.3216(9)
_cell_length_b                   6.6441(5)
_cell_length_c                   12.0540(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.426(4)
_cell_angle_gamma                90
_cell_volume                     796.86(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2608
_cell_measurement_theta_min      1.753
_cell_measurement_theta_max      27.120

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.214
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            6854
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.753
_diffrn_reflns_theta_max         27.120
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_point_group_measured_fraction_full 0.829
_reflns_number_total             2788
_reflns_number_gt                2608
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.451
_reflns_Friedel_fraction_max     0.536
_reflns_Friedel_fraction_full    0.622

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

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+0.0361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 776 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2788
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8041(2) 0.2259(3) 0.99141(19) 0.0369(5) Uani 1 1 d . . . . .
O1 O 0.89617(17) 0.1722(3) 0.95166(17) 0.0499(4) Uani 1 1 d . . . . .
N2 N 0.7621(2) 0.4170(3) 0.98660(19) 0.0441(5) Uani 1 1 d . . . . .
H2 H 0.700(3) 0.447(6) 1.013(2) 0.059(8) Uiso 1 1 d . . . . .
N3 N 0.8195(2) 0.5675(3) 0.9323(2) 0.0516(5) Uani 1 1 d . . . . .
H3A H 0.909(3) 0.578(5) 0.967(3) 0.062(9) Uiso 1 1 d . . . . .
H3B H 0.818(3) 0.519(6) 0.859(3) 0.074(11) Uiso 1 1 d . . . . .
C4 C 0.7261(2) 0.0759(4) 1.0451(2) 0.0396(5) Uani 1 1 d . . . . .
H4 H 0.657(3) 0.135(4) 1.063(2) 0.050(8) Uiso 1 1 d . . . . .
C41 C 0.8142(3) -0.0330(6) 1.1500(2) 0.0536(6) Uani 1 1 d . . . . .
H41A H 0.761(3) -0.143(5) 1.170(2) 0.051(5) Uiso 1 1 d . U . . .
H41B H 0.891(3) -0.077(5) 1.133(2) 0.051(5) Uiso 1 1 d . U . . .
C42 C 0.8557(4) 0.0899(7) 1.2609(3) 0.0794(11) Uani 1 1 d . . . . .
H42 H 0.782(4) 0.179(7) 1.272(4) 0.108(14) Uiso 1 1 d . . . . .
C43 C 0.9658(6) 0.2395(9) 1.2623(4) 0.1204(19) Uani 1 1 d . . . . .
H43A H 1.0472 0.1690 1.2628 0.181 Uiso 1 1 calc R U . . .
H43B H 0.9805 0.3219 1.3299 0.181 Uiso 1 1 calc R U . . .
H43C H 0.9401 0.3231 1.1950 0.181 Uiso 1 1 calc R U . . .
C44 C 0.8999(5) -0.0514(13) 1.3632(3) 0.134(2) Uani 1 1 d . . . . .
H44A H 0.9249 0.0259 1.4330 0.201 Uiso 1 1 calc R U . . .
H44B H 0.9756 -0.1292 1.3558 0.201 Uiso 1 1 calc R U . . .
H44C H 0.8272 -0.1400 1.3654 0.201 Uiso 1 1 calc R U . . .
N5 N 0.6658(2) -0.0778(3) 0.95977(17) 0.0400(4) Uani 1 1 d . . . . .
H5 H 0.713(3) -0.163(5) 0.942(2) 0.039(7) Uiso 1 1 d . . . . .
S6 S 0.53762(5) -0.03814(8) 0.85367(5) 0.03900(15) Uani 1 1 d . . . . .
O7 O 0.44161(17) 0.0755(3) 0.89520(16) 0.0523(5) Uani 1 1 d . . . . .
O8 O 0.4993(2) -0.2306(3) 0.80089(18) 0.0565(5) Uani 1 1 d . . . . .
C9 C 0.5862(2) 0.1133(4) 0.7513(2) 0.0393(5) Uani 1 1 d . . . . .
C10 C 0.5408(3) 0.3074(4) 0.7296(2) 0.0484(6) Uani 1 1 d . . . . .
H10 H 0.484(3) 0.339(6) 0.769(3) 0.066(10) Uiso 1 1 d . . . . .
C11 C 0.5777(3) 0.4199(5) 0.6460(2) 0.0582(7) Uani 1 1 d . . . . .
H11 H 0.548(4) 0.554(7) 0.636(3) 0.083(11) Uiso 1 1 d . . . . .
C12 C 0.6611(3) 0.3400(5) 0.5838(2) 0.0575(7) Uani 1 1 d . . . . .
C121 C 0.7002(4) 0.4623(8) 0.4919(3) 0.0858(11) Uani 1 1 d . . . . .
H12A H 0.6457 0.4228 0.4175 0.129 Uiso 1 1 calc R U . . .
H12B H 0.7932 0.4391 0.4961 0.129 Uiso 1 1 calc R U . . .
H12C H 0.6865 0.6027 0.5039 0.129 Uiso 1 1 calc R U . . .
C13 C 0.7077(3) 0.1456(6) 0.6088(3) 0.0672(9) Uani 1 1 d . . . . .
H13 H 0.758(3) 0.083(6) 0.566(3) 0.072(10) Uiso 1 1 d . . . . .
C14 C 0.6709(3) 0.0308(5) 0.6908(3) 0.0592(7) Uani 1 1 d . . . . .
H14 H 0.709(3) -0.099(6) 0.709(3) 0.069(10) 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
C1 O1 1.225(3) . ?
C1 N2 1.338(3) . ?
C1 C4 1.529(3) . ?
N2 N3 1.409(3) . ?
N2 H2 0.82(3) . ?
N3 H3A 0.91(3) . ?
N3 H3B 0.94(4) . ?
C4 N5 1.466(3) . ?
C4 C41 1.529(4) . ?
C4 H4 0.89(3) . ?
C41 C42 1.527(5) . ?
C41 H41A 0.98(3) . ?
C41 H41B 0.92(3) . ?
C42 C43 1.507(6) . ?
C42 C44 1.520(7) . ?
C42 H42 1.00(4) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
N5 S6 1.599(2) . ?
N5 H5 0.81(3) . ?
S6 O8 1.4358(19) . ?
S6 O7 1.4376(19) . ?
S6 C9 1.765(2) . ?
C9 C10 1.373(4) . ?
C9 C14 1.392(4) . ?
C10 C11 1.387(4) . ?
C10 H10 0.87(3) . ?
C11 C12 1.388(5) . ?
C11 H11 0.94(4) . ?
C12 C13 1.383(5) . ?
C12 C121 1.512(4) . ?
C121 H12A 0.9600 . ?
C121 H12B 0.9600 . ?
C121 H12C 0.9600 . ?
C13 C14 1.379(5) . ?
C13 H13 0.92(3) . ?
C14 H14 0.95(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
O1 C1 N2 122.4(2) . . ?
O1 C1 C4 121.7(2) . . ?
N2 C1 C4 115.8(2) . . ?
C1 N2 N3 121.5(2) . . ?
C1 N2 H2 120(3) . . ?
N3 N2 H2 119(3) . . ?
N2 N3 H3A 110(2) . . ?
N2 N3 H3B 107(2) . . ?
H3A N3 H3B 103(3) . . ?
N5 C4 C1 109.33(18) . . ?
N5 C4 C41 107.4(2) . . ?
C1 C4 C41 113.2(2) . . ?
N5 C4 H4 105.0(18) . . ?
C1 C4 H4 111.0(19) . . ?
C41 C4 H4 110.5(18) . . ?
C42 C41 C4 116.0(3) . . ?
C42 C41 H41A 103.2(17) . . ?
C4 C41 H41A 107.7(17) . . ?
C42 C41 H41B 107.7(17) . . ?
C4 C41 H41B 109.4(17) . . ?
H41A C41 H41B 113(3) . . ?
C43 C42 C44 109.6(4) . . ?
C43 C42 C41 113.5(3) . . ?
C44 C42 C41 109.5(4) . . ?
C43 C42 H42 102(3) . . ?
C44 C42 H42 109(3) . . ?
C41 C42 H42 113(3) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C4 N5 S6 123.56(16) . . ?
C4 N5 H5 120.2(19) . . ?
S6 N5 H5 109.0(18) . . ?
O8 S6 O7 119.22(12) . . ?
O8 S6 N5 106.21(12) . . ?
O7 S6 N5 107.97(11) . . ?
O8 S6 C9 107.09(11) . . ?
O7 S6 C9 107.11(12) . . ?
N5 S6 C9 108.95(10) . . ?
C10 C9 C14 119.9(3) . . ?
C10 C9 S6 121.55(19) . . ?
C14 C9 S6 118.5(2) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 112(2) . . ?
C11 C10 H10 128(2) . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11 118(2) . . ?
C12 C11 H11 121(2) . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 C121 121.1(3) . . ?
C11 C12 C121 121.0(3) . . ?
C12 C121 H12A 109.5 . . ?
C12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
C12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 H13 117(2) . . ?
C12 C13 H13 121(2) . . ?
C13 C14 C9 119.3(3) . . ?
C13 C14 H14 119(2) . . ?
C9 C14 H14 121(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N2 N3 1.8(4) . . . . ?
C4 C1 N2 N3 -175.6(2) . . . . ?
O1 C1 C4 N5 -58.2(3) . . . . ?
N2 C1 C4 N5 119.2(2) . . . . ?
O1 C1 C4 C41 61.4(3) . . . . ?
N2 C1 C4 C41 -121.1(2) . . . . ?
N5 C4 C41 C42 -163.8(3) . . . . ?
C1 C4 C41 C42 75.4(3) . . . . ?
C4 C41 C42 C43 -76.2(4) . . . . ?
C4 C41 C42 C44 161.0(3) . . . . ?
C1 C4 N5 S6 -74.4(2) . . . . ?
C41 C4 N5 S6 162.47(17) . . . . ?
C4 N5 S6 O8 -172.18(19) . . . . ?
C4 N5 S6 O7 -43.2(2) . . . . ?
C4 N5 S6 C9 72.8(2) . . . . ?
O8 S6 C9 C10 133.2(2) . . . . ?
O7 S6 C9 C10 4.3(2) . . . . ?
N5 S6 C9 C10 -112.3(2) . . . . ?
O8 S6 C9 C14 -45.8(2) . . . . ?
O7 S6 C9 C14 -174.7(2) . . . . ?
N5 S6 C9 C14 68.7(2) . . . . ?
C14 C9 C10 C11 1.0(4) . . . . ?
S6 C9 C10 C11 -178.0(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C10 C11 C12 C121 179.4(3) . . . . ?
C11 C12 C13 C14 1.5(5) . . . . ?
C121 C12 C13 C14 -178.8(3) . . . . ?
C12 C13 C14 C9 -1.0(5) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
S6 C9 C14 C13 178.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O7 0.82(3) 2.22(3) 3.026(3) 168(3) 2_657
N3 H3A O1 0.91(3) 2.08(3) 2.979(3) 167(3) 2_757
N5 H5 N3 0.81(3) 2.12(3) 2.908(3) 163(3) 1_545
C10 H10 O7 0.87(3) 2.44(3) 2.915(4) 115(3) .

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.033

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

data_5c_LMOHQAU
_database_code_depnum_ccdc_archive 'CCDC 1826228'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H19 N3 O4 S'
_chemical_formula_sum            'C12 H19 N3 O4 S'
_chemical_formula_weight         301.36

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

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

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

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

_cell_length_a                   10.4333(7)
_cell_length_b                   6.8279(4)
_cell_length_c                   11.1774(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.332(4)
_cell_angle_gamma                90
_cell_volume                     731.14(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2730
_cell_measurement_theta_min      1.984
_cell_measurement_theta_max      27.267

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            6469
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.984
_diffrn_reflns_theta_max         27.267
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3061
_reflns_number_gt                2731
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_max     0.860
_reflns_Friedel_fraction_full    0.910

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

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3061
_refine_ls_number_parameters     224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2611(3) 0.9273(4) -0.1047(2) 0.0341(6) Uani 1 1 d . . . . .
O1 O 0.3685(2) 0.9845(3) -0.1129(2) 0.0523(6) Uani 1 1 d . . . . .
N2 N 0.2424(3) 0.7427(4) -0.0789(2) 0.0395(5) Uani 1 1 d . . . . .
H2 H 0.174(3) 0.707(5) -0.072(3) 0.044(10) Uiso 1 1 d . . . . .
N3 N 0.3427(3) 0.5932(4) -0.0613(4) 0.0509(7) Uani 1 1 d . . . . .
H3A H 0.377(4) 0.612(6) -0.121(4) 0.075(13) Uiso 1 1 d . . . . .
H3B H 0.401(5) 0.606(8) 0.013(5) 0.11(2) Uiso 1 1 d . . . . .
C4 C 0.1380(3) 1.0636(4) -0.1310(2) 0.0318(6) Uani 1 1 d . . . . .
H4 H 0.072(3) 0.997(4) -0.109(2) 0.026(7) Uiso 1 1 d . . . . .
C41 C 0.0749(3) 1.1195(5) -0.2762(3) 0.0429(7) Uani 1 1 d . . . . .
H41 H 0.152(3) 1.195(4) -0.290(3) 0.041(8) Uiso 1 1 d . . . . .
C42 C -0.0511(4) 1.2505(6) -0.3079(3) 0.0647(9) Uani 1 1 d . . . . .
H42A H -0.0877 1.2841 -0.3987 0.097 Uiso 1 1 calc R U . . .
H42B H -0.0243 1.3677 -0.2565 0.097 Uiso 1 1 calc R U . . .
H42C H -0.1213 1.1829 -0.2885 0.097 Uiso 1 1 calc R U . . .
C43 C 0.0360(4) 0.9362(6) -0.3597(3) 0.0665(10) Uani 1 1 d . . . . .
H43A H -0.0248 0.8565 -0.3344 0.100 Uiso 1 1 calc R U . . .
H43B H 0.1191 0.8637 -0.3479 0.100 Uiso 1 1 calc R U . . .
H43C H -0.0107 0.9723 -0.4497 0.100 Uiso 1 1 calc R U . . .
N5 N 0.1791(2) 1.2414(3) -0.05194(19) 0.0356(5) Uani 1 1 d . . . . .
H5 H 0.236(3) 1.316(5) -0.063(3) 0.042(9) Uiso 1 1 d . . . . .
S6 S 0.18618(7) 1.25353(8) 0.09390(6) 0.03400(17) Uani 1 1 d . . . . .
O7 O 0.2114(2) 1.4553(3) 0.13226(19) 0.0474(5) Uani 1 1 d . . . . .
O8 O 0.0646(2) 1.1577(3) 0.09517(19) 0.0438(5) Uani 1 1 d . . . . .
C9 C 0.3322(3) 1.1203(4) 0.1982(2) 0.0336(6) Uani 1 1 d . . . . .
C10 C 0.4587(3) 1.2165(4) 0.2581(3) 0.0477(8) Uani 1 1 d . . . . .
H10 H 0.463(4) 1.346(6) 0.241(3) 0.069(11) Uiso 1 1 d . . . . .
C11 C 0.5730(4) 1.1163(5) 0.3414(3) 0.0543(8) Uani 1 1 d . . . . .
H11 H 0.668(4) 1.174(5) 0.381(3) 0.070(11) Uiso 1 1 d . . . . .
C12 C 0.5636(3) 0.9161(4) 0.3628(3) 0.0430(7) Uani 1 1 d . . . . .
O12 O 0.6829(3) 0.8334(3) 0.4476(2) 0.0641(7) Uani 1 1 d . . . . .
C121 C 0.6822(4) 0.6302(5) 0.4706(4) 0.0650(10) Uani 1 1 d . . . . .
H12A H 0.6116 0.6007 0.5026 0.097 Uiso 1 1 calc R U . . .
H12B H 0.7718 0.5912 0.5340 0.097 Uiso 1 1 calc R U . . .
H12C H 0.6629 0.5603 0.3907 0.097 Uiso 1 1 calc R U . . .
C13 C 0.4380(3) 0.8203(4) 0.3011(3) 0.0406(7) Uani 1 1 d . . . . .
H13 H 0.434(3) 0.686(5) 0.314(3) 0.040(8) Uiso 1 1 d . . . . .
C14 C 0.3230(3) 0.9230(4) 0.2186(2) 0.0362(6) Uani 1 1 d . . . . .
H14 H 0.238(3) 0.863(4) 0.178(2) 0.026(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
C1 O1 1.224(3) . ?
C1 N2 1.325(4) . ?
C1 C4 1.518(4) . ?
N2 N3 1.419(4) . ?
N2 H2 0.78(3) . ?
N3 H3A 0.88(4) . ?
N3 H3B 0.81(5) . ?
C4 N5 1.462(3) . ?
C4 C41 1.539(4) . ?
C4 H4 0.93(3) . ?
C41 C42 1.512(4) . ?
C41 C43 1.517(5) . ?
C41 H41 1.01(3) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
N5 S6 1.605(2) . ?
N5 H5 0.82(3) . ?
S6 O8 1.432(2) . ?
S6 O7 1.436(2) . ?
S6 C9 1.761(3) . ?
C9 C14 1.376(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.370(4) . ?
C10 H10 0.91(4) . ?
C11 C12 1.398(5) . ?
C11 H11 0.99(4) . ?
C12 O12 1.353(4) . ?
C12 C13 1.380(4) . ?
O12 C121 1.412(4) . ?
C121 H12A 0.9600 . ?
C121 H12B 0.9600 . ?
C121 H12C 0.9600 . ?
C13 C14 1.381(4) . ?
C13 H13 0.93(3) . ?
C14 H14 0.92(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
O1 C1 N2 122.6(3) . . ?
O1 C1 C4 121.3(2) . . ?
N2 C1 C4 116.0(2) . . ?
C1 N2 N3 123.4(2) . . ?
C1 N2 H2 122(2) . . ?
N3 N2 H2 114(2) . . ?
N2 N3 H3A 107(3) . . ?
N2 N3 H3B 106(4) . . ?
H3A N3 H3B 113(4) . . ?
N5 C4 C1 111.6(2) . . ?
N5 C4 C41 109.4(2) . . ?
C1 C4 C41 109.3(2) . . ?
N5 C4 H4 108.6(16) . . ?
C1 C4 H4 107.8(16) . . ?
C41 C4 H4 110.0(15) . . ?
C42 C41 C43 110.4(3) . . ?
C42 C41 C4 111.2(2) . . ?
C43 C41 C4 110.0(3) . . ?
C42 C41 H41 109.2(16) . . ?
C43 C41 H41 111.4(16) . . ?
C4 C41 H41 104.4(16) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C4 N5 S6 122.75(19) . . ?
C4 N5 H5 119(2) . . ?
S6 N5 H5 111.7(19) . . ?
O8 S6 O7 119.57(13) . . ?
O8 S6 N5 107.58(13) . . ?
O7 S6 N5 106.40(12) . . ?
O8 S6 C9 107.16(12) . . ?
O7 S6 C9 106.84(13) . . ?
N5 S6 C9 108.98(12) . . ?
C14 C9 C10 119.9(3) . . ?
C14 C9 S6 121.1(2) . . ?
C10 C9 S6 118.9(2) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 122(2) . . ?
C9 C10 H10 118(2) . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 124(2) . . ?
C12 C11 H11 116(2) . . ?
O12 C12 C13 125.4(3) . . ?
O12 C12 C11 114.9(3) . . ?
C13 C12 C11 119.7(3) . . ?
C12 O12 C121 117.9(3) . . ?
O12 C121 H12A 109.5 . . ?
O12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
O12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 119(2) . . ?
C14 C13 H13 122(2) . . ?
C9 C14 C13 120.6(3) . . ?
C9 C14 H14 118.0(17) . . ?
C13 C14 H14 121.4(16) . . ?

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
O1 C1 N2 N3 -1.5(5) . . . . ?
C4 C1 N2 N3 175.4(3) . . . . ?
O1 C1 C4 N5 -53.7(3) . . . . ?
N2 C1 C4 N5 129.4(2) . . . . ?
O1 C1 C4 C41 67.5(3) . . . . ?
N2 C1 C4 C41 -109.4(3) . . . . ?
N5 C4 C41 C42 -59.2(3) . . . . ?
C1 C4 C41 C42 178.3(3) . . . . ?
N5 C4 C41 C43 178.1(3) . . . . ?
C1 C4 C41 C43 55.6(3) . . . . ?
C1 C4 N5 S6 -85.7(3) . . . . ?
C41 C4 N5 S6 153.2(2) . . . . ?
C4 N5 S6 O8 -43.0(2) . . . . ?
C4 N5 S6 O7 -172.3(2) . . . . ?
C4 N5 S6 C9 72.8(2) . . . . ?
O8 S6 C9 C14 28.1(2) . . . . ?
O7 S6 C9 C14 157.4(2) . . . . ?
N5 S6 C9 C14 -88.0(2) . . . . ?
O8 S6 C9 C10 -153.2(2) . . . . ?
O7 S6 C9 C10 -23.9(3) . . . . ?
N5 S6 C9 C10 90.6(2) . . . . ?
C14 C9 C10 C11 -2.5(5) . . . . ?
S6 C9 C10 C11 178.8(3) . . . . ?
C9 C10 C11 C12 2.1(5) . . . . ?
C10 C11 C12 O12 -179.6(3) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C13 C12 O12 C121 3.5(5) . . . . ?
C11 C12 O12 C121 -177.9(3) . . . . ?
O12 C12 C13 C14 178.7(3) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C10 C9 C14 C13 1.7(4) . . . . ?
S6 C9 C14 C13 -179.7(2) . . . . ?
C12 C13 C14 C9 -0.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O8 0.78(3) 2.42(3) 3.189(3) 165(3) 2_545
N3 H3B O1 0.81(5) 2.37(5) 2.962(4) 131(4) 2_645
N5 H5 N3 0.82(3) 2.20(3) 2.973(4) 157(3) 1_565

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_5e_VCH
_database_code_depnum_ccdc_archive 'CCDC 1826230'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H16 Cl N3 O3 S'
_chemical_formula_weight         305.78

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

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

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

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

_cell_length_a                   10.4296(6)
_cell_length_b                   6.7642(3)
_cell_length_c                   11.2829(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.623(3)
_cell_angle_gamma                90
_cell_volume                     729.28(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2891
_cell_measurement_theta_min      2.249
_cell_measurement_theta_max      27.862

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.412
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.60
_diffrn_reflns_number            6483
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         27.862
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3285
_reflns_number_gt                2892
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.891
_reflns_Friedel_fraction_full    0.947

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

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+0.0383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3285
_refine_ls_number_parameters     214
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2344(3) 0.1013(4) 0.5993(3) 0.0479(6) Uani 1 1 d . . . . .
O1 O 0.1234(2) 0.1564(4) 0.6005(3) 0.0742(7) Uani 1 1 d . . . . .
N2 N 0.2584(3) -0.0857(4) 0.5795(2) 0.0529(5) Uani 1 1 d . . . . .
H2 H 0.326(4) -0.113(6) 0.571(3) 0.059(10) Uiso 1 1 d . . . . .
N3 N 0.1589(4) -0.2373(4) 0.5602(5) 0.0675(8) Uani 1 1 d . . . . .
H3A H 0.122(4) -0.230(7) 0.614(4) 0.072(13) Uiso 1 1 d . . . . .
H3B H 0.103(6) -0.213(10) 0.492(6) 0.11(2) Uiso 1 1 d . . . . .
C4 C 0.3554(3) 0.2425(4) 0.6279(3) 0.0462(6) Uani 1 1 d . . . . .
H4 H 0.417(4) 0.187(6) 0.614(3) 0.052(9) Uiso 1 1 d . . . . .
C41 C 0.4091(4) 0.3113(6) 0.7703(3) 0.0668(9) Uani 1 1 d . . . . .
H41 H 0.336(3) 0.394(5) 0.781(2) 0.043(7) Uiso 1 1 d . . . . .
C42 C 0.5376(5) 0.4377(9) 0.8061(4) 0.0927(14) Uani 1 1 d . . . . .
H42A H 0.5701 0.4749 0.8955 0.139 Uiso 1 1 calc R U . . .
H42B H 0.5154 0.5543 0.7532 0.139 Uiso 1 1 calc R U . . .
H42C H 0.6094 0.3646 0.7925 0.139 Uiso 1 1 calc R U . . .
C43 C 0.4397(6) 0.1328(9) 0.8595(4) 0.1061(17) Uani 1 1 d . . . . .
H32A H 0.5018 0.0446 0.8416 0.159 Uiso 1 1 calc R U . . .
H43B H 0.3538 0.0653 0.8455 0.159 Uiso 1 1 calc R U . . .
H43C H 0.4827 0.1759 0.9479 0.159 Uiso 1 1 calc R U . . .
N5 N 0.3139(3) 0.4162(4) 0.5435(2) 0.0494(5) Uani 1 1 d . . . . .
H5 H 0.255(4) 0.480(6) 0.549(3) 0.056(10) Uiso 1 1 d . . . . .
S6 S 0.31287(7) 0.42219(10) 0.40177(6) 0.04774(19) Uani 1 1 d . . . . .
O7 O 0.4375(2) 0.3274(4) 0.4063(2) 0.0600(6) Uani 1 1 d . . . . .
O8 O 0.2846(3) 0.6229(3) 0.3586(2) 0.0674(6) Uani 1 1 d . . . . .
C9 C 0.1702(3) 0.2789(4) 0.2962(3) 0.0486(6) Uani 1 1 d . . . . .
C10 C 0.0407(4) 0.3652(6) 0.2342(4) 0.0639(9) Uani 1 1 d . . . . .
H10 H 0.030(4) 0.482(8) 0.251(4) 0.075(13) Uiso 1 1 d . . . . .
C11 C -0.0695(4) 0.2542(7) 0.1487(4) 0.0747(10) Uani 1 1 d . . . . .
H11 H -0.152(5) 0.301(7) 0.114(4) 0.078(12) Uiso 1 1 d . . . . .
C12 C -0.0476(4) 0.0572(6) 0.1289(3) 0.0671(9) Uani 1 1 d . . . . .
Cl12 Cl -0.18417(12) -0.0816(3) 0.02029(11) 0.1093(5) Uani 1 1 d . . . . .
C13 C 0.0798(4) -0.0297(5) 0.1918(4) 0.0651(9) Uani 1 1 d . . . . .
H13 H 0.087(4) -0.164(7) 0.170(4) 0.070(11) Uiso 1 1 d . . . . .
C14 C 0.1894(3) 0.0832(5) 0.2773(3) 0.0564(7) Uani 1 1 d . . . . .
H14 H 0.272(4) 0.022(6) 0.323(4) 0.063(10) 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
C1 O1 1.221(4) . ?
C1 N2 1.326(4) . ?
C1 C4 1.511(4) . ?
N2 N3 1.412(4) . ?
N2 H2 0.77(4) . ?
N3 H3A 0.84(4) . ?
N3 H3B 0.78(6) . ?
C4 N5 1.464(4) . ?
C4 C41 1.545(5) . ?
C4 H4 0.81(4) . ?
C41 C42 1.502(6) . ?
C41 C43 1.522(6) . ?
C41 H41 0.99(3) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H32A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
N5 S6 1.596(2) . ?
N5 H5 0.77(4) . ?
S6 O7 1.432(2) . ?
S6 O8 1.432(2) . ?
S6 C9 1.775(3) . ?
C9 C14 1.369(5) . ?
C9 C10 1.377(5) . ?
C10 C11 1.388(6) . ?
C10 H10 0.83(5) . ?
C11 C12 1.385(6) . ?
C11 H11 0.86(4) . ?
C12 C13 1.364(5) . ?
C12 Cl12 1.736(4) . ?
C13 C14 1.392(5) . ?
C13 H13 0.95(4) . ?
C14 H14 0.90(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
O1 C1 N2 122.5(3) . . ?
O1 C1 C4 121.2(3) . . ?
N2 C1 C4 116.2(2) . . ?
C1 N2 N3 122.8(2) . . ?
C1 N2 H2 120(3) . . ?
N3 N2 H2 117(3) . . ?
N2 N3 H3A 111(3) . . ?
N2 N3 H3B 102(5) . . ?
H3A N3 H3B 109(6) . . ?
N5 C4 C1 111.4(2) . . ?
N5 C4 C41 108.9(3) . . ?
C1 C4 C41 109.7(3) . . ?
N5 C4 H4 107(2) . . ?
C1 C4 H4 109(3) . . ?
C41 C4 H4 111(2) . . ?
C42 C41 C43 110.2(4) . . ?
C42 C41 C4 111.3(3) . . ?
C43 C41 C4 110.0(4) . . ?
C42 C41 H41 106.9(19) . . ?
C43 C41 H41 109.7(17) . . ?
C4 C41 H41 108.6(16) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H32A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H32A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H32A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C4 N5 S6 123.6(2) . . ?
C4 N5 H5 116(3) . . ?
S6 N5 H5 112(3) . . ?
O7 S6 O8 119.81(15) . . ?
O7 S6 N5 108.13(14) . . ?
O8 S6 N5 106.40(16) . . ?
O7 S6 C9 106.54(14) . . ?
O8 S6 C9 106.62(14) . . ?
N5 S6 C9 109.02(14) . . ?
C14 C9 C10 120.4(3) . . ?
C14 C9 S6 119.8(2) . . ?
C10 C9 S6 119.8(3) . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 H10 118(3) . . ?
C11 C10 H10 122(3) . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 H11 119(3) . . ?
C10 C11 H11 121(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 Cl12 119.2(3) . . ?
C11 C12 Cl12 119.5(3) . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 116(3) . . ?
C14 C13 H13 125(3) . . ?
C9 C14 C13 120.6(3) . . ?
C9 C14 H14 121(3) . . ?
C13 C14 H14 118(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N2 N3 -1.0(5) . . . . ?
C4 C1 N2 N3 175.7(3) . . . . ?
O1 C1 C4 N5 -54.7(4) . . . . ?
N2 C1 C4 N5 128.6(3) . . . . ?
O1 C1 C4 C41 65.9(4) . . . . ?
N2 C1 C4 C41 -110.8(3) . . . . ?
N5 C4 C41 C42 -63.0(4) . . . . ?
C1 C4 C41 C42 174.9(3) . . . . ?
N5 C4 C41 C43 174.6(3) . . . . ?
C1 C4 C41 C43 52.5(4) . . . . ?
C1 C4 N5 S6 -84.8(3) . . . . ?
C41 C4 N5 S6 154.1(2) . . . . ?
C4 N5 S6 O7 -42.6(3) . . . . ?
C4 N5 S6 O8 -172.5(2) . . . . ?
C4 N5 S6 C9 72.8(3) . . . . ?
O7 S6 C9 C14 24.6(3) . . . . ?
O8 S6 C9 C14 153.6(3) . . . . ?
N5 S6 C9 C14 -91.9(3) . . . . ?
O7 S6 C9 C10 -155.7(3) . . . . ?
O8 S6 C9 C10 -26.6(3) . . . . ?
N5 S6 C9 C10 87.9(3) . . . . ?
C14 C9 C10 C11 -2.2(5) . . . . ?
S6 C9 C10 C11 178.0(3) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C10 C11 C12 Cl12 -179.0(3) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
Cl12 C12 C13 C14 179.1(3) . . . . ?
C10 C9 C14 C13 2.3(5) . . . . ?
S6 C9 C14 C13 -177.9(3) . . . . ?
C12 C13 C14 C9 -1.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O7 0.77(4) 2.41(4) 3.165(3) 167(3) 2_646
N3 H3B O1 0.78(6) 2.34(6) 2.863(4) 126(6) 2_546
N5 H5 N3 0.77(4) 2.19(4) 2.896(4) 153(4) 1_565

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039

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

data_5d_HACNQAU
_database_code_depnum_ccdc_archive 'CCDC 1826229'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 Cl N3 O3 S'
_chemical_formula_weight         277.73

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

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

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

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

_cell_length_a                   10.0850(5)
_cell_length_b                   6.6661(3)
_cell_length_c                   18.9899(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.813(3)
_cell_angle_gamma                90
_cell_volume                     1234.22(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5005
_cell_measurement_theta_min      1.109
_cell_measurement_theta_max      27.460

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.479
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.60
_diffrn_reflns_number            10869
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.109
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5581
_reflns_number_gt                5008
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.2225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2041 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5581
_refine_ls_number_parameters     381
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C -0.0279(3) 0.7282(5) 0.33629(17) 0.0348(6) Uani 1 1 d . . . . .
O1A O -0.0024(3) 0.7860(4) 0.28035(14) 0.0522(7) Uani 1 1 d . . . . .
N2A N -0.0296(3) 0.5348(4) 0.35379(15) 0.0418(6) Uani 1 1 d . . . . .
H2A H -0.050(4) 0.498(7) 0.390(2) 0.056(12) Uiso 1 1 d . . . . .
N3A N 0.0056(4) 0.3813(4) 0.31013(17) 0.0465(7) Uani 1 1 d . . . . .
H3A H -0.069(5) 0.346(7) 0.270(2) 0.059(12) Uiso 1 1 d . . . . .
H3B H 0.077(4) 0.445(7) 0.287(2) 0.058(12) Uiso 1 1 d . . . . .
C4A C -0.0636(3) 0.8732(5) 0.39121(18) 0.0370(7) Uani 1 1 d . . . . .
H4A H -0.063(3) 0.811(5) 0.4331(18) 0.025(8) Uiso 1 1 d . . . . .
C41A C -0.2061(4) 0.9593(7) 0.3598(2) 0.0543(10) Uani 1 1 d . . . . .
H41A H -0.2257 1.0574 0.3928 0.081 Uiso 1 1 calc R U . . .
H41B H -0.2727 0.8535 0.3531 0.081 Uiso 1 1 calc R U . . .
H41C H -0.2098 1.0215 0.3138 0.081 Uiso 1 1 calc R U . . .
N5A N 0.0353(3) 1.0375(4) 0.40869(15) 0.0375(5) Uani 1 1 d . . . . .
H5A H 0.033(4) 1.121(6) 0.378(2) 0.040(10) Uiso 1 1 d . . . . .
S6A S 0.18046(8) 1.01220(12) 0.46668(4) 0.03829(18) Uani 1 1 d . . . . .
O7A O 0.2399(3) 1.2083(4) 0.47728(16) 0.0571(7) Uani 1 1 d . . . . .
O8A O 0.1575(3) 0.9026(4) 0.52736(12) 0.0502(6) Uani 1 1 d . . . . .
C9A C 0.2872(3) 0.8608(5) 0.42747(17) 0.0378(7) Uani 1 1 d . . . . .
C10A C 0.3376(5) 0.9390(7) 0.3723(2) 0.0540(10) Uani 1 1 d . . . . .
H10A H 0.317(4) 1.052(8) 0.354(2) 0.060(13) Uiso 1 1 d . . . . .
C11A C 0.4182(4) 0.8213(7) 0.3398(2) 0.0583(10) Uani 1 1 d . . . . .
H11A H 0.464(5) 0.876(7) 0.306(3) 0.067(13) Uiso 1 1 d . . . . .
C12A C 0.4481(4) 0.6287(6) 0.3642(2) 0.0477(8) Uani 1 1 d . . . . .
Cl1A Cl 0.54900(12) 0.4785(2) 0.32333(7) 0.0721(3) Uani 1 1 d . . . . .
C13A C 0.3997(4) 0.5498(7) 0.4191(2) 0.0558(9) Uani 1 1 d . . . . .
H13A H 0.427(6) 0.422(9) 0.437(3) 0.084(17) Uiso 1 1 d . . . . .
C14A C 0.3179(4) 0.6678(6) 0.4517(2) 0.0511(9) Uani 1 1 d . . . . .
H14A H 0.288(5) 0.624(8) 0.489(3) 0.068(14) Uiso 1 1 d . . . . .
C1B C 0.6462(3) 0.3325(5) 0.15699(18) 0.0373(7) Uani 1 1 d . . . . .
O1B O 0.7351(3) 0.2734(4) 0.20850(15) 0.0543(7) Uani 1 1 d . . . . .
N2B N 0.6265(3) 0.5263(5) 0.14026(15) 0.0449(6) Uani 1 1 d . . . . .
H2B H 0.566(5) 0.562(8) 0.109(2) 0.063(14) Uiso 1 1 d . . . . .
N3B N 0.7086(4) 0.6775(5) 0.1820(2) 0.0558(9) Uani 1 1 d . . . . .
H3C H 0.699(5) 0.678(8) 0.228(3) 0.067(14) Uiso 1 1 d . . . . .
H3D H 0.799(5) 0.658(8) 0.180(2) 0.067(14) Uiso 1 1 d . . . . .
C4B C 0.5475(4) 0.1871(5) 0.1069(2) 0.0428(8) Uani 1 1 d . . . . .
H4B H 0.507(4) 0.240(6) 0.062(2) 0.046(10) Uiso 1 1 d . . . . .
C41B C 0.4453(5) 0.1082(8) 0.1457(3) 0.0721(13) Uani 1 1 d . . . . .
H41D H 0.3809 0.0221 0.1136 0.108 Uiso 1 1 calc R U . . .
H41E H 0.3973 0.2185 0.1604 0.108 Uiso 1 1 calc R U . . .
H41F H 0.4926 0.0337 0.1880 0.108 Uiso 1 1 calc R U . . .
N5B N 0.6216(3) 0.0188(5) 0.08605(16) 0.0408(6) Uani 1 1 d . . . . .
H5B H 0.650(4) -0.056(7) 0.116(2) 0.039(11) Uiso 1 1 d . . . . .
S6B S 0.71179(8) 0.04004(13) 0.02818(4) 0.0425(2) Uani 1 1 d . . . . .
O7B O 0.6324(3) 0.1531(5) -0.03238(14) 0.0580(7) Uani 1 1 d . . . . .
O8B O 0.7559(3) -0.1583(4) 0.01697(17) 0.0617(8) Uani 1 1 d . . . . .
C9B C 0.8591(3) 0.1833(5) 0.06783(18) 0.0408(7) Uani 1 1 d . . . . .
C10B C 0.8697(4) 0.3796(6) 0.0458(2) 0.0492(8) Uani 1 1 d . . . . .
H10B H 0.805(5) 0.413(8) -0.001(3) 0.079(16) Uiso 1 1 d . . . . .
C11B C 0.9825(4) 0.4926(7) 0.0803(3) 0.0571(10) Uani 1 1 d . . . . .
H11B H 0.998(5) 0.613(8) 0.073(3) 0.064(14) Uiso 1 1 d . . . . .
C12B C 1.0818(4) 0.4092(7) 0.1350(2) 0.0559(10) Uani 1 1 d . . . . .
Cl1B Cl 1.22053(12) 0.5531(3) 0.17981(8) 0.0905(5) Uani 1 1 d . . . . .
C13B C 1.0723(4) 0.2134(8) 0.1570(2) 0.0573(10) Uani 1 1 d . . . . .
H13B H 1.133(5) 0.167(7) 0.192(2) 0.057(12) Uiso 1 1 d . . . . .
C14B C 0.9606(4) 0.0996(7) 0.1232(2) 0.0501(9) Uani 1 1 d . . . . .
H14B H 0.945(4) -0.014(8) 0.143(2) 0.053(12) 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
C1A O1A 1.218(4) . ?
C1A N2A 1.332(4) . ?
C1A C4A 1.531(4) . ?
N2A N3A 1.417(4) . ?
N2A H2A 0.81(4) . ?
N3A H3A 0.96(5) . ?
N3A H3B 1.03(5) . ?
C4A N5A 1.462(4) . ?
C4A C41A 1.520(5) . ?
C4A H4A 0.89(3) . ?
C41A H41A 0.9600 . ?
C41A H41B 0.9600 . ?
C41A H41C 0.9600 . ?
N5A S6A 1.600(3) . ?
N5A H5A 0.80(4) . ?
S6A O7A 1.431(3) . ?
S6A O8A 1.432(3) . ?
S6A C9A 1.773(3) . ?
C9A C14A 1.374(5) . ?
C9A C10A 1.378(5) . ?
C10A C11A 1.383(6) . ?
C10A H10A 0.84(5) . ?
C11A C12A 1.372(6) . ?
C11A H11A 0.95(5) . ?
C12A C13A 1.365(6) . ?
C12A Cl1A 1.744(4) . ?
C13A C14A 1.394(6) . ?
C13A H13A 0.93(6) . ?
C14A H14A 0.88(5) . ?
C1B O1B 1.212(4) . ?
C1B N2B 1.333(5) . ?
C1B C4B 1.534(5) . ?
N2B N3B 1.413(4) . ?
N2B H2B 0.77(5) . ?
N3B H3C 0.90(5) . ?
N3B H3D 0.93(5) . ?
C4B N5B 1.457(4) . ?
C4B C41B 1.507(6) . ?
C4B H4B 0.92(4) . ?
C41B H41D 0.9600 . ?
C41B H41E 0.9600 . ?
C41B H41F 0.9600 . ?
N5B S6B 1.602(3) . ?
N5B H5B 0.75(4) . ?
S6B O8B 1.428(3) . ?
S6B O7B 1.436(3) . ?
S6B C9B 1.765(3) . ?
C9B C14B 1.384(5) . ?
C9B C10B 1.386(5) . ?
C10B C11B 1.382(6) . ?
C10B H10B 0.98(5) . ?
C11B C12B 1.364(6) . ?
C11B H11B 0.84(5) . ?
C12B C13B 1.381(7) . ?
C12B Cl1B 1.731(4) . ?
C13B C14B 1.374(6) . ?
C13B H13B 0.84(5) . ?
C14B H14B 0.88(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
O1A C1A N2A 122.9(3) . . ?
O1A C1A C4A 122.2(3) . . ?
N2A C1A C4A 114.9(3) . . ?
C1A N2A N3A 122.1(3) . . ?
C1A N2A H2A 122(3) . . ?
N3A N2A H2A 116(3) . . ?
N2A N3A H3A 113(3) . . ?
N2A N3A H3B 105(2) . . ?
H3A N3A H3B 104(3) . . ?
N5A C4A C41A 109.1(3) . . ?
N5A C4A C1A 111.2(3) . . ?
C41A C4A C1A 109.5(3) . . ?
N5A C4A H4A 107(2) . . ?
C41A C4A H4A 108(2) . . ?
C1A C4A H4A 111(2) . . ?
C4A C41A H41A 109.5 . . ?
C4A C41A H41B 109.5 . . ?
H41A C41A H41B 109.5 . . ?
C4A C41A H41C 109.5 . . ?
H41A C41A H41C 109.5 . . ?
H41B C41A H41C 109.5 . . ?
C4A N5A S6A 121.9(2) . . ?
C4A N5A H5A 117(3) . . ?
S6A N5A H5A 115(3) . . ?
O7A S6A O8A 120.06(17) . . ?
O7A S6A N5A 106.07(17) . . ?
O8A S6A N5A 107.45(15) . . ?
O7A S6A C9A 107.56(17) . . ?
O8A S6A C9A 106.76(16) . . ?
N5A S6A C9A 108.54(14) . . ?
C14A C9A C10A 120.9(4) . . ?
C14A C9A S6A 120.1(3) . . ?
C10A C9A S6A 119.1(3) . . ?
C9A C10A C11A 119.8(4) . . ?
C9A C10A H10A 124(3) . . ?
C11A C10A H10A 116(3) . . ?
C12A C11A C10A 118.9(4) . . ?
C12A C11A H11A 119(3) . . ?
C10A C11A H11A 121(3) . . ?
C13A C12A C11A 121.8(4) . . ?
C13A C12A Cl1A 118.8(3) . . ?
C11A C12A Cl1A 119.4(3) . . ?
C12A C13A C14A 119.3(4) . . ?
C12A C13A H13A 120(4) . . ?
C14A C13A H13A 121(4) . . ?
C9A C14A C13A 119.2(4) . . ?
C9A C14A H14A 119(3) . . ?
C13A C14A H14A 122(3) . . ?
O1B C1B N2B 122.8(3) . . ?
O1B C1B C4B 121.6(3) . . ?
N2B C1B C4B 115.5(3) . . ?
C1B N2B N3B 121.8(3) . . ?
C1B N2B H2B 122(4) . . ?
N3B N2B H2B 116(4) . . ?
N2B N3B H3C 111(3) . . ?
N2B N3B H3D 109(3) . . ?
H3C N3B H3D 113(4) . . ?
N5B C4B C41B 109.0(3) . . ?
N5B C4B C1B 111.0(3) . . ?
C41B C4B C1B 109.5(3) . . ?
N5B C4B H4B 101(2) . . ?
C41B C4B H4B 113(2) . . ?
C1B C4B H4B 113(3) . . ?
C4B C41B H41D 109.5 . . ?
C4B C41B H41E 109.5 . . ?
H41D C41B H41E 109.5 . . ?
C4B C41B H41F 109.5 . . ?
H41D C41B H41F 109.5 . . ?
H41E C41B H41F 109.5 . . ?
C4B N5B S6B 122.6(3) . . ?
C4B N5B H5B 115(3) . . ?
S6B N5B H5B 113(3) . . ?
O8B S6B O7B 119.86(18) . . ?
O8B S6B N5B 105.87(18) . . ?
O7B S6B N5B 107.31(17) . . ?
O8B S6B C9B 107.72(17) . . ?
O7B S6B C9B 107.09(18) . . ?
N5B S6B C9B 108.61(15) . . ?
C14B C9B C10B 120.7(4) . . ?
C14B C9B S6B 119.0(3) . . ?
C10B C9B S6B 120.2(3) . . ?
C11B C10B C9B 119.3(4) . . ?
C11B C10B H10B 125(3) . . ?
C9B C10B H10B 114(3) . . ?
C12B C11B C10B 119.6(4) . . ?
C12B C11B H11B 113(4) . . ?
C10B C11B H11B 128(4) . . ?
C11B C12B C13B 121.5(4) . . ?
C11B C12B Cl1B 119.5(4) . . ?
C13B C12B Cl1B 119.0(4) . . ?
C14B C13B C12B 119.5(4) . . ?
C14B C13B H13B 121(3) . . ?
C12B C13B H13B 120(3) . . ?
C13B C14B C9B 119.4(4) . . ?
C13B C14B H14B 119(3) . . ?
C9B C14B H14B 120(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A N2A N3A 3.4(5) . . . . ?
C4A C1A N2A N3A -177.8(3) . . . . ?
O1A C1A C4A N5A -49.1(4) . . . . ?
N2A C1A C4A N5A 132.1(3) . . . . ?
O1A C1A C4A C41A 71.7(4) . . . . ?
N2A C1A C4A C41A -107.1(3) . . . . ?
C41A C4A N5A S6A 157.9(2) . . . . ?
C1A C4A N5A S6A -81.1(3) . . . . ?
C4A N5A S6A O7A -171.8(3) . . . . ?
C4A N5A S6A O8A -42.3(3) . . . . ?
C4A N5A S6A C9A 72.8(3) . . . . ?
O7A S6A C9A C14A 137.3(3) . . . . ?
O8A S6A C9A C14A 7.2(3) . . . . ?
N5A S6A C9A C14A -108.3(3) . . . . ?
O7A S6A C9A C10A -43.2(3) . . . . ?
O8A S6A C9A C10A -173.3(3) . . . . ?
N5A S6A C9A C10A 71.2(3) . . . . ?
C14A C9A C10A C11A 1.1(6) . . . . ?
S6A C9A C10A C11A -178.4(3) . . . . ?
C9A C10A C11A C12A -1.0(7) . . . . ?
C10A C11A C12A C13A 0.5(7) . . . . ?
C10A C11A C12A Cl1A 179.7(3) . . . . ?
C11A C12A C13A C14A -0.2(6) . . . . ?
Cl1A C12A C13A C14A -179.4(3) . . . . ?
C10A C9A C14A C13A -0.8(6) . . . . ?
S6A C9A C14A C13A 178.7(3) . . . . ?
C12A C13A C14A C9A 0.4(6) . . . . ?
O1B C1B N2B N3B -0.2(6) . . . . ?
C4B C1B N2B N3B 179.3(4) . . . . ?
O1B C1B C4B N5B -46.8(5) . . . . ?
N2B C1B C4B N5B 133.7(3) . . . . ?
O1B C1B C4B C41B 73.7(5) . . . . ?
N2B C1B C4B C41B -105.9(4) . . . . ?
C41B C4B N5B S6B 165.2(3) . . . . ?
C1B C4B N5B S6B -74.1(4) . . . . ?
C4B N5B S6B O8B -174.3(3) . . . . ?
C4B N5B S6B O7B -45.2(3) . . . . ?
C4B N5B S6B C9B 70.3(3) . . . . ?
O8B S6B C9B C14B -43.4(3) . . . . ?
O7B S6B C9B C14B -173.6(3) . . . . ?
N5B S6B C9B C14B 70.8(3) . . . . ?
O8B S6B C9B C10B 139.4(3) . . . . ?
O7B S6B C9B C10B 9.2(4) . . . . ?
N5B S6B C9B C10B -106.4(3) . . . . ?
C14B C9B C10B C11B -0.6(6) . . . . ?
S6B C9B C10B C11B 176.5(3) . . . . ?
C9B C10B C11B C12B 0.4(6) . . . . ?
C10B C11B C12B C13B -0.1(6) . . . . ?
C10B C11B C12B Cl1B -178.2(3) . . . . ?
C11B C12B C13B C14B 0.0(6) . . . . ?
Cl1B C12B C13B C14B 178.1(3) . . . . ?
C12B C13B C14B C9B -0.2(6) . . . . ?
C10B C9B C14B C13B 0.5(6) . . . . ?
S6B C9B C14B C13B -176.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2A H2A O8A 0.81(4) 2.21(4) 3.004(4) 166(4) 2_546
N3A H3A O1B 0.96(5) 2.08(5) 2.998(4) 161(4) 1_455
N5A H5A N3A 0.80(4) 2.14(4) 2.925(4) 168(4) 1_565
N2B H2B O7B 0.77(5) 2.24(5) 2.999(4) 170(5) 2_655
N5B H5B N3B 0.75(4) 2.17(4) 2.907(4) 166(4) 1_545

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048

