# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_k14sip1
_database_code_depnum_ccdc_archive 'CCDC 1542385'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N4 O2 S, Cl, H2 O'
_chemical_formula_sum            'C21 H23 Cl N4 O3 S'
_chemical_formula_weight         446.94

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2813(2)
_cell_length_b                   9.4897(3)
_cell_length_c                   15.4934(6)
_cell_angle_alpha                91.1888(12)
_cell_angle_beta                 101.8010(12)
_cell_angle_gamma                100.7680(15)
_cell_volume                     1027.54(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11912
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '175 2.0 degree images with ω scans'
_diffrn_reflns_number            15108
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.0688
_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       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.914
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4689
_reflns_number_gt                3495
_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2013 (Sheldrick, 2013)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX- 2013.3 publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 2012, 45, 849-854
;

_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)+(0.0382P)²+0.2294P] 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_number_reflns         4689
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Cl Cl 0.28146(7) -0.24875(5) 0.45820(3) 0.03019(13) Uani 1 1 d . . . . .
S S 0.43543(6) -0.48603(5) -0.16003(3) 0.02380(13) Uani 1 1 d . . . . .
N1 N 0.2031(2) 0.23994(15) 0.40712(10) 0.0204(3) Uani 1 1 d . . . . .
H1 H 0.252(3) 0.183(2) 0.4468(16) 0.040(6) Uiso 1 1 d . . . . .
N2 N 0.1674(2) 0.07310(14) 0.24561(10) 0.0186(3) Uani 1 1 d . . . . .
N3 N 0.2396(2) -0.30034(14) -0.09586(10) 0.0182(3) Uani 1 1 d . . . . .
N4 N 0.0969(2) -0.44794(15) -0.22783(10) 0.0231(3) Uani 1 1 d . . . . .
O1 O 0.20475(18) -0.47626(12) -0.00002(9) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.31172(17) -0.12389(12) -0.18810(8) 0.0218(3) Uani 1 1 d . . . . .
O3 O 0.3162(2) 0.06178(15) 0.53720(9) 0.0270(3) Uani 1 1 d . . . . .
H3C H 0.431(4) 0.098(3) 0.5511(19) 0.059(8) Uiso 1 1 d . . . . .
H3D H 0.306(4) -0.026(3) 0.5158(19) 0.069(9) Uiso 1 1 d . . . . .
C1 C 0.1788(3) 0.36697(19) 0.45889(13) 0.0295(4) Uani 1 1 d . . . . .
H1A H 0.3032 0.4146 0.4944 0.044 Uiso 1 1 calc R U . . .
H1B H 0.0908 0.3353 0.4979 0.044 Uiso 1 1 calc R U . . .
H1C H 0.1265 0.4345 0.4183 0.044 Uiso 1 1 calc R U . . .
C2 C 0.0152(2) 0.15442(18) 0.35803(12) 0.0224(4) Uani 1 1 d . . . . .
H2A H -0.0503 0.2151 0.3156 0.027 Uiso 1 1 calc R U . . .
H2B H -0.0675 0.1226 0.4001 0.027 Uiso 1 1 calc R U . . .
C3 C 0.0473(2) 0.02448(18) 0.30876(12) 0.0214(4) Uani 1 1 d . . . . .
H3A H 0.1109 -0.0372 0.3511 0.026 Uiso 1 1 calc R U . . .
H3B H -0.0771 -0.0327 0.2770 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3327(3) 0.28295(19) 0.34513(13) 0.0235(4) Uani 1 1 d . . . . .
H4A H 0.4593 0.3332 0.3789 0.028 Uiso 1 1 calc R U . . .
H4B H 0.2792 0.3503 0.3037 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3560(2) 0.15247(18) 0.29347(12) 0.0216(4) Uani 1 1 d . . . . .
H5A H 0.4378 0.1833 0.2509 0.026 Uiso 1 1 calc R U . . .
H5B H 0.4194 0.0889 0.3344 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1800(2) -0.03322(17) 0.18231(11) 0.0179(4) Uani 1 1 d . . . . .
C7 C 0.2166(2) 0.01225(17) 0.09896(12) 0.0168(3) Uani 1 1 d . . . . .
C8 C 0.2348(2) 0.15781(17) 0.07643(12) 0.0181(4) Uani 1 1 d . . . . .
H8 H 0.2210 0.2285 0.1177 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2720(2) 0.19829(17) -0.00374(12) 0.0194(4) Uani 1 1 d . . . . .
H9 H 0.2870 0.2966 -0.0168 0.023 Uiso 1 1 calc R U . . .
C10 C 0.2880(2) 0.09490(17) -0.06647(12) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.3150 0.1236 -0.1217 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2647(2) -0.04809(17) -0.04826(11) 0.0166(3) Uani 1 1 d . . . . .
C12 C 0.2750(2) -0.15443(17) -0.11697(12) 0.0176(4) Uani 1 1 d . . . . .
C13 C 0.2149(2) -0.34923(17) -0.01264(12) 0.0184(4) Uani 1 1 d . . . . .
C14 C 0.2037(2) -0.23944(17) 0.05349(12) 0.0178(4) Uani 1 1 d . . . . .
C15 C 0.1648(2) -0.28012(18) 0.13325(12) 0.0212(4) Uani 1 1 d . . . . .
H15 H 0.1455 -0.3790 0.1452 0.025 Uiso 1 1 calc R U . . .
C16 C 0.1531(3) -0.17774(18) 0.19745(12) 0.0219(4) Uani 1 1 d . . . . .
H16 H 0.1262 -0.2083 0.2523 0.026 Uiso 1 1 calc R U . . .
C17 C 0.2296(2) -0.09159(16) 0.03420(11) 0.0156(3) Uani 1 1 d . . . . .
C18 C 0.2400(2) -0.40577(17) -0.16245(12) 0.0185(4) Uani 1 1 d . . . . .
C19 C 0.1403(3) -0.55087(18) -0.28099(12) 0.0243(4) Uani 1 1 d . . . . .
H19 H 0.0522 -0.5945 -0.3327 0.029 Uiso 1 1 calc R U . . .
C20 C 0.3147(3) -0.58647(18) -0.25561(12) 0.0228(4) Uani 1 1 d . . . . .
C21 C 0.3972(3) -0.6960(2) -0.29854(14) 0.0330(5) Uani 1 1 d . . . . .
H21A H 0.2991 -0.7499 -0.3468 0.049 Uiso 1 1 calc R U . . .
H21B H 0.4406 -0.7623 -0.2548 0.049 Uiso 1 1 calc R U . . .
H21C H 0.5058 -0.6473 -0.3221 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C20 1.7235(18) . ?
S C18 1.7294(17) . ?
N1 C4 1.491(2) . ?
N1 C1 1.492(2) . ?
N1 C2 1.497(2) . ?
N1 H1 0.89(2) . ?
N2 C6 1.421(2) . ?
N2 C3 1.467(2) . ?
N2 C5 1.475(2) . ?
N3 C13 1.414(2) . ?
N3 C12 1.418(2) . ?
N3 C18 1.423(2) . ?
N4 C18 1.291(2) . ?
N4 C19 1.386(2) . ?
O1 C13 1.216(2) . ?
O2 C12 1.215(2) . ?
O3 H3C 0.82(3) . ?
O3 H3D 0.88(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.516(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.515(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C16 1.381(2) . ?
C6 C7 1.430(2) . ?
C7 C8 1.421(2) . ?
C7 C17 1.421(2) . ?
C8 C9 1.372(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(2) . ?
C10 H10 0.9500 . ?
C11 C17 1.409(2) . ?
C11 C12 1.474(2) . ?
C13 C14 1.471(2) . ?
C14 C15 1.371(2) . ?
C14 C17 1.426(2) . ?
C15 C16 1.402(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C19 C20 1.357(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.501(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C20 S C18 89.28(8) . . ?
C4 N1 C1 111.53(14) . . ?
C4 N1 C2 110.33(14) . . ?
C1 N1 C2 111.99(14) . . ?
C4 N1 H1 110.6(15) . . ?
C1 N1 H1 105.9(14) . . ?
C2 N1 H1 106.2(14) . . ?
C6 N2 C3 115.99(13) . . ?
C6 N2 C5 113.14(13) . . ?
C3 N2 C5 109.75(14) . . ?
C13 N3 C12 125.43(14) . . ?
C13 N3 C18 117.27(13) . . ?
C12 N3 C18 117.20(14) . . ?
C18 N4 C19 109.33(15) . . ?
H3C O3 H3D 108(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 109.90(14) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N2 C3 C2 109.13(14) . . ?
N2 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
N2 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N1 C4 C5 110.71(14) . . ?
N1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N2 C5 C4 110.12(14) . . ?
N2 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N2 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C16 C6 N2 122.57(16) . . ?
C16 C6 C7 119.28(15) . . ?
N2 C6 C7 118.13(14) . . ?
C8 C7 C17 117.84(15) . . ?
C8 C7 C6 122.67(15) . . ?
C17 C7 C6 119.46(14) . . ?
C9 C8 C7 121.29(16) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.20(15) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.23(16) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C17 120.44(15) . . ?
C10 C11 C12 118.78(16) . . ?
C17 C11 C12 120.77(14) . . ?
O2 C12 N3 119.85(15) . . ?
O2 C12 C11 124.17(15) . . ?
N3 C12 C11 115.98(15) . . ?
O1 C13 N3 119.20(15) . . ?
O1 C13 C14 124.50(17) . . ?
N3 C13 C14 116.30(14) . . ?
C15 C14 C17 120.07(15) . . ?
C15 C14 C13 119.66(15) . . ?
C17 C14 C13 120.25(16) . . ?
C14 C15 C16 120.86(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C6 C16 C15 121.16(17) . . ?
C6 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C11 C17 C7 119.93(14) . . ?
C11 C17 C14 120.91(15) . . ?
C7 C17 C14 119.15(15) . . ?
N4 C18 N3 122.93(15) . . ?
N4 C18 S 115.75(13) . . ?
N3 C18 S 121.31(12) . . ?
C20 C19 N4 116.85(16) . . ?
C20 C19 H19 121.6 . . ?
N4 C19 H19 121.6 . . ?
C19 C20 C21 128.40(17) . . ?
C19 C20 S 108.79(13) . . ?
C21 C20 S 122.79(15) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
N1 H1 O3 0.89(2) 1.87(2) 2.754(2) 170(2) .
O3 H3C Cl 0.82(3) 2.34(3) 3.1147(16) 158(3) 2_656
O3 H3D Cl 0.88(3) 2.24(3) 3.1130(15) 179(3) .

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
