# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_d8v18271_0m
_database_code_depnum_ccdc_archive 'CCDC 1834287'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N O3 S'
_chemical_formula_weight         345.44

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 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.0366(5)
_cell_length_b                   20.3622(13)
_cell_length_c                   12.3027(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.424(3)
_cell_angle_gamma                90
_cell_volume                     1751.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4091
_cell_measurement_theta_min      5.207
_cell_measurement_theta_max      54.888

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6464
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8987
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.080
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3215
_reflns_number_gt                2565
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1139P)²+2.3803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.2223
_refine_ls_wR_factor_gt          0.2099
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.24844(13) 0.55104(4) 0.69514(8) 0.0471(4) Uani 1 1 d . . . . .
O1 O 0.3129(7) 0.7228(2) 0.2241(3) 0.1029(14) Uani 1 1 d . . . . .
O2 O 0.0606(4) 0.54189(15) 0.7276(3) 0.0668(8) Uani 1 1 d . . . . .
O3 O 0.3307(4) 0.50073(13) 0.6346(2) 0.0578(8) Uani 1 1 d . . . . .
N1 N 0.2431(4) 0.61794(15) 0.6257(2) 0.0445(7) Uani 1 1 d . . . . .
C1 C 0.3781(6) 0.7374(2) 0.4169(4) 0.0669(12) Uani 1 1 d . . . . .
H1A H 0.3111 0.7789 0.4051 0.080 Uiso 1 1 calc R U . . .
H1B H 0.5138 0.7471 0.4278 0.080 Uiso 1 1 calc R U . . .
C2 C 0.3396(7) 0.6972(2) 0.3146(4) 0.0700(13) Uani 1 1 d . . . . .
C3 C 0.3456(7) 0.6240(2) 0.3271(4) 0.0667(12) Uani 1 1 d . . . . .
H3A H 0.4777 0.6096 0.3312 0.080 Uiso 1 1 calc R U . . .
H3B H 0.2772 0.6043 0.2624 0.080 Uiso 1 1 calc R U . . .
C4 C 0.2592(6) 0.59888(18) 0.4281(3) 0.0494(9) Uani 1 1 d . . . . .
H4 H 0.2815 0.5515 0.4344 0.059 Uiso 1 1 calc R U . . .
C5 C 0.3562(5) 0.63239(17) 0.5320(3) 0.0439(8) Uani 1 1 d . . . . .
C6 C 0.3216(5) 0.70721(17) 0.5220(3) 0.0480(9) Uani 1 1 d . . . . .
H6 H 0.3942 0.7290 0.5844 0.058 Uiso 1 1 calc R U . . .
C7 C 0.1082(5) 0.71133(17) 0.5356(3) 0.0454(8) Uani 1 1 d . . . . .
H7 H 0.0690 0.7567 0.5477 0.054 Uiso 1 1 calc R U . . .
C8 C -0.0020(5) 0.68251(18) 0.4355(3) 0.0461(9) Uani 1 1 d . . . . .
C9 C 0.0425(6) 0.61131(19) 0.4167(3) 0.0522(9) Uani 1 1 d . . . . .
H9A H -0.0126 0.5986 0.3439 0.063 Uiso 1 1 calc R U . . .
H9B H -0.0152 0.5844 0.4692 0.063 Uiso 1 1 calc R U . . .
C10 C -0.1150(7) 0.7184(3) 0.3668(4) 0.0651(12) Uani 1 1 d . . . . .
C11 C 0.0986(6) 0.66920(19) 0.6379(3) 0.0518(9) Uani 1 1 d . . . . .
H11A H 0.1311 0.6946 0.7040 0.062 Uiso 1 1 calc R U . . .
H11B H -0.0275 0.6502 0.6393 0.062 Uiso 1 1 calc R U . . .
C12 C 0.5670(6) 0.6162(2) 0.5579(4) 0.0652(12) Uani 1 1 d . . . . .
H12A H 0.6144 0.6352 0.6271 0.098 Uiso 1 1 calc R U . . .
H12B H 0.6366 0.6338 0.5017 0.098 Uiso 1 1 calc R U . . .
H12C H 0.5833 0.5694 0.5612 0.098 Uiso 1 1 calc R U . . .
C13 C 0.4055(6) 0.56440(18) 0.8152(3) 0.0503(9) Uani 1 1 d . . . . .
C14 C 0.3377(7) 0.5915(2) 0.9062(3) 0.0627(11) Uani 1 1 d . . . . .
H14 H 0.2090 0.6022 0.9051 0.075 Uiso 1 1 calc R U . . .
C15 C 0.4642(10) 0.6027(2) 0.9994(4) 0.0764(15) Uani 1 1 d . . . . .
H15 H 0.4183 0.6209 1.0607 0.092 Uiso 1 1 calc R U . . .
C16 C 0.6548(9) 0.5876(2) 1.0036(4) 0.0738(15) Uani 1 1 d . . . . .
C17 C 0.7194(7) 0.5601(2) 0.9123(4) 0.0712(13) Uani 1 1 d . . . . .
H17 H 0.8481 0.5492 0.9141 0.085 Uiso 1 1 calc R U . . .
C18 C 0.5975(6) 0.5482(2) 0.8179(4) 0.0596(11) Uani 1 1 d . . . . .
H18 H 0.6439 0.5296 0.7571 0.072 Uiso 1 1 calc R U . . .
C19 C 0.7901(11) 0.6009(3) 1.1051(4) 0.108(2) Uani 1 1 d . . . . .
H19A H 0.8706 0.6375 1.0923 0.163 Uiso 1 1 calc R U . . .
H19B H 0.8677 0.5628 1.1228 0.163 Uiso 1 1 calc R U . . .
H19C H 0.7180 0.6109 1.1648 0.163 Uiso 1 1 calc R U . . .
H10A H -0.177(7) 0.700(2) 0.299(4) 0.073(14) Uiso 1 1 d . . . . .
H10B H -0.138(7) 0.769(2) 0.383(4) 0.073(14) 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 O3 1.427(3) . ?
S1 O2 1.435(3) . ?
S1 N1 1.606(3) . ?
S1 C13 1.764(4) . ?
O1 C2 1.224(5) . ?
N1 C11 1.476(4) . ?
N1 C5 1.501(4) . ?
C1 C2 1.501(7) . ?
C1 C6 1.524(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.497(6) . ?
C3 C4 1.532(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.536(5) . ?
C4 C5 1.540(5) . ?
C4 H4 0.9800 . ?
C5 C12 1.518(5) . ?
C5 C6 1.546(5) . ?
C6 C7 1.532(5) . ?
C6 H6 0.9800 . ?
C7 C8 1.499(5) . ?
C7 C11 1.531(5) . ?
C7 H7 0.9800 . ?
C8 C10 1.316(6) . ?
C8 C9 1.507(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.97(5) . ?
C10 H10B 1.07(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.380(6) . ?
C13 C18 1.388(6) . ?
C14 C15 1.390(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(7) . ?
C16 C19 1.508(7) . ?
C17 C18 1.386(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 119.49(18) . . ?
O3 S1 N1 108.54(16) . . ?
O2 S1 N1 106.90(17) . . ?
O3 S1 C13 107.17(18) . . ?
O2 S1 C13 107.29(19) . . ?
N1 S1 C13 106.84(17) . . ?
C11 N1 C5 111.7(3) . . ?
C11 N1 S1 121.4(2) . . ?
C5 N1 S1 126.3(2) . . ?
C2 C1 C6 116.8(3) . . ?
C2 C1 H1A 108.1 . . ?
C6 C1 H1A 108.1 . . ?
C2 C1 H1B 108.1 . . ?
C6 C1 H1B 108.1 . . ?
H1A C1 H1B 107.3 . . ?
O1 C2 C3 121.1(5) . . ?
O1 C2 C1 121.6(4) . . ?
C3 C2 C1 117.2(4) . . ?
C2 C3 C4 114.0(4) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C9 110.5(3) . . ?
C3 C4 C5 110.2(3) . . ?
C9 C4 C5 110.3(3) . . ?
C3 C4 H4 108.6 . . ?
C9 C4 H4 108.6 . . ?
C5 C4 H4 108.6 . . ?
N1 C5 C12 112.7(3) . . ?
N1 C5 C4 109.1(3) . . ?
C12 C5 C4 114.2(3) . . ?
N1 C5 C6 99.3(3) . . ?
C12 C5 C6 111.8(3) . . ?
C4 C5 C6 108.6(3) . . ?
C1 C6 C7 115.0(3) . . ?
C1 C6 C5 114.4(3) . . ?
C7 C6 C5 101.1(3) . . ?
C1 C6 H6 108.7 . . ?
C7 C6 H6 108.7 . . ?
C5 C6 H6 108.7 . . ?
C8 C7 C11 112.9(3) . . ?
C8 C7 C6 108.2(3) . . ?
C11 C7 C6 101.2(3) . . ?
C8 C7 H7 111.4 . . ?
C11 C7 H7 111.4 . . ?
C6 C7 H7 111.4 . . ?
C10 C8 C7 122.0(4) . . ?
C10 C8 C9 123.8(4) . . ?
C7 C8 C9 113.9(3) . . ?
C8 C9 C4 111.4(3) . . ?
C8 C9 H9A 109.3 . . ?
C4 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C4 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C8 C10 H10A 121(3) . . ?
C8 C10 H10B 121(3) . . ?
H10A C10 H10B 118(4) . . ?
N1 C11 C7 102.6(3) . . ?
N1 C11 H11A 111.2 . . ?
C7 C11 H11A 111.2 . . ?
N1 C11 H11B 111.2 . . ?
C7 C11 H11B 111.2 . . ?
H11A C11 H11B 109.2 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 120.0(4) . . ?
C14 C13 S1 120.0(4) . . ?
C18 C13 S1 120.0(3) . . ?
C13 C14 C15 119.1(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 121.8(5) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 118.2(4) . . ?
C15 C16 C19 121.0(5) . . ?
C17 C16 C19 120.9(6) . . ?
C16 C17 C18 121.6(5) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 119.2(4) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N1 C11 152.7(3) . . . . ?
O2 S1 N1 C11 22.6(3) . . . . ?
C13 S1 N1 C11 -92.0(3) . . . . ?
O3 S1 N1 C5 -17.4(3) . . . . ?
O2 S1 N1 C5 -147.6(3) . . . . ?
C13 S1 N1 C5 97.8(3) . . . . ?
C6 C1 C2 O1 153.2(4) . . . . ?
C6 C1 C2 C3 -30.0(6) . . . . ?
O1 C2 C3 C4 -144.3(5) . . . . ?
C1 C2 C3 C4 38.9(6) . . . . ?
C2 C3 C4 C9 67.1(5) . . . . ?
C2 C3 C4 C5 -55.0(5) . . . . ?
C11 N1 C5 C12 140.1(3) . . . . ?
S1 N1 C5 C12 -49.0(4) . . . . ?
C11 N1 C5 C4 -92.0(3) . . . . ?
S1 N1 C5 C4 79.0(4) . . . . ?
C11 N1 C5 C6 21.5(4) . . . . ?
S1 N1 C5 C6 -167.5(3) . . . . ?
C3 C4 C5 N1 168.3(3) . . . . ?
C9 C4 C5 N1 45.9(4) . . . . ?
C3 C4 C5 C12 -64.6(4) . . . . ?
C9 C4 C5 C12 173.1(3) . . . . ?
C3 C4 C5 C6 61.0(4) . . . . ?
C9 C4 C5 C6 -61.4(4) . . . . ?
C2 C1 C6 C7 -78.9(5) . . . . ?
C2 C1 C6 C5 37.5(5) . . . . ?
N1 C5 C6 C1 -166.5(3) . . . . ?
C12 C5 C6 C1 74.3(4) . . . . ?
C4 C5 C6 C1 -52.7(4) . . . . ?
N1 C5 C6 C7 -42.4(3) . . . . ?
C12 C5 C6 C7 -161.6(3) . . . . ?
C4 C5 C6 C7 71.5(4) . . . . ?
C1 C6 C7 C8 53.7(4) . . . . ?
C5 C6 C7 C8 -70.1(4) . . . . ?
C1 C6 C7 C11 172.5(3) . . . . ?
C5 C6 C7 C11 48.8(3) . . . . ?
C11 C7 C8 C10 135.2(4) . . . . ?
C6 C7 C8 C10 -113.7(4) . . . . ?
C11 C7 C8 C9 -50.0(4) . . . . ?
C6 C7 C8 C9 61.1(4) . . . . ?
C10 C8 C9 C4 127.4(4) . . . . ?
C7 C8 C9 C4 -47.4(4) . . . . ?
C3 C4 C9 C8 -75.6(4) . . . . ?
C5 C4 C9 C8 46.5(4) . . . . ?
C5 N1 C11 C7 8.1(4) . . . . ?
S1 N1 C11 C7 -163.4(2) . . . . ?
C8 C7 C11 N1 80.6(4) . . . . ?
C6 C7 C11 N1 -34.7(3) . . . . ?
O3 S1 C13 C14 -156.8(3) . . . . ?
O2 S1 C13 C14 -27.3(4) . . . . ?
N1 S1 C13 C14 87.0(3) . . . . ?
O3 S1 C13 C18 23.8(4) . . . . ?
O2 S1 C13 C18 153.3(3) . . . . ?
N1 S1 C13 C18 -92.4(3) . . . . ?
C18 C13 C14 C15 0.5(6) . . . . ?
S1 C13 C14 C15 -178.9(3) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C14 C15 C16 C17 -0.7(7) . . . . ?
C14 C15 C16 C19 179.2(4) . . . . ?
C15 C16 C17 C18 0.6(7) . . . . ?
C19 C16 C17 C18 -179.3(4) . . . . ?
C16 C17 C18 C13 0.0(7) . . . . ?
C14 C13 C18 C17 -0.5(6) . . . . ?
S1 C13 C18 C17 178.9(3) . . . . ?

_refine_diff_density_max         0.854
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

