# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_mx6876
_database_code_depnum_ccdc_archive 'CCDC 1836267'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N3 O3 S'
_chemical_formula_sum            'C14 H11 N3 O3 S'
_chemical_formula_weight         301.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.471(4)
_cell_length_b                   10.038(3)
_cell_length_c                   13.551(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.028(5)
_cell_angle_gamma                90
_cell_volume                     1398.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4478
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4607
_cell_measurement_theta_min      1.9816
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10678
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         2.542
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2956
_reflns_number_total             3175
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.9384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1274
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.55199(5) 0.23424(5) 0.54903(4) 0.03052(16) Uani 1 1 d . . . . .
C1 C 0.6924(2) 0.2209(2) 0.41768(15) 0.0298(4) Uani 1 1 d . . . . .
N1 N 0.44966(16) 0.31833(18) 0.46731(12) 0.0274(4) Uani 1 1 d . . . . .
O1 O 0.62772(15) 0.14545(14) 0.48163(11) 0.0338(4) Uani 1 1 d . . . . .
O2 O 0.64372(15) 0.32464(16) 0.60441(11) 0.0383(4) Uani 1 1 d . . . . .
N2 N 0.43889(19) 0.0896(2) 0.23122(15) 0.0384(4) Uani 1 1 d . . . . .
C2 C 0.8137(2) 0.1783(3) 0.40540(18) 0.0426(6) Uani 1 1 d . . . . .
H2 H 0.852601 0.101482 0.439540 0.051 Uiso 1 1 calc R . . . .
N3 N 0.3809(2) 0.4975(2) 0.14103(15) 0.0485(6) Uani 1 1 d . . . . .
C3 C 0.8770(2) 0.2499(3) 0.3423(2) 0.0498(7) Uani 1 1 d . . . . .
H3 H 0.959684 0.221053 0.331643 0.060 Uiso 1 1 calc R . . . .
O3 O 0.48323(18) 0.14416(18) 0.59974(12) 0.0473(4) Uani 1 1 d . . . . .
C4 C 0.8212(2) 0.3636(3) 0.29444(19) 0.0461(6) Uani 1 1 d . . . . .
H4 H 0.865659 0.412600 0.251436 0.055 Uiso 1 1 calc R . . . .
C5 C 0.7005(2) 0.4055(2) 0.30941(16) 0.0344(5) Uani 1 1 d . . . . .
H5 H 0.663279 0.484540 0.277612 0.041 Uiso 1 1 calc R . . . .
C6 C 0.63305(19) 0.3333(2) 0.37051(14) 0.0256(4) Uani 1 1 d . . . . .
C7 C 0.49792(18) 0.37511(19) 0.38043(13) 0.0236(4) Uani 1 1 d . . . . .
H7 H 0.495663 0.474473 0.385100 0.028 Uiso 1 1 calc R . . . .
C8 C 0.38990(19) 0.3294(2) 0.28906(14) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.26655(19) 0.3313(2) 0.33521(15) 0.0305(4) Uani 1 1 d . . . . .
H9A H 0.233904 0.423435 0.338771 0.037 Uiso 1 1 calc R . . . .
H9B H 0.197023 0.276239 0.295094 0.037 Uiso 1 1 calc R . . . .
C10 C 0.31024(19) 0.2730(2) 0.44063(15) 0.0300(4) Uani 1 1 d . . . . .
H10 H 0.304898 0.173568 0.438897 0.036 Uiso 1 1 calc R . . . .
C11 C 0.41740(19) 0.1940(2) 0.25584(14) 0.0262(4) Uani 1 1 d . . . . .
C12 C 0.3835(2) 0.4225(2) 0.20444(15) 0.0326(5) Uani 1 1 d . . . . .
C13 C 0.2306(2) 0.3292(3) 0.51189(17) 0.0469(6) Uani 1 1 d . . . . .
H13 H 0.232767 0.422958 0.521520 0.056 Uiso 1 1 calc R . . . .
C14 C 0.1600(3) 0.2613(4) 0.5607(2) 0.0700(10) Uani 1 1 d . . . . .
H14A H 0.155081 0.167222 0.553236 0.084 Uiso 1 1 calc R . . . .
H14B H 0.112527 0.304907 0.604398 0.084 Uiso 1 1 calc R . . . .


_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 N1 1.6226(17) . ?
S1 O1 1.5920(16) . ?
S1 O2 1.4260(16) . ?
S1 O3 1.4133(17) . ?
C1 O1 1.417(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.383(3) . ?
N1 C7 1.481(2) . ?
N1 C10 1.506(3) . ?
N2 C11 1.135(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
N3 C12 1.139(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 C7 1.506(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.577(3) . ?
C8 C9 1.539(3) . ?
C8 C11 1.477(3) . ?
C8 C12 1.471(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.531(3) . ?
C10 H10 1.0000 . ?
C10 C13 1.501(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.278(4) . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 103.65(8) . . ?
O2 S1 N1 108.57(10) . . ?
O2 S1 O1 107.39(10) . . ?
O3 S1 N1 109.48(10) . . ?
O3 S1 O1 106.06(10) . . ?
O3 S1 O2 120.38(10) . . ?
C2 C1 O1 117.8(2) . . ?
C2 C1 C6 122.7(2) . . ?
C6 C1 O1 119.56(18) . . ?
C7 N1 S1 117.49(13) . . ?
C7 N1 C10 112.83(15) . . ?
C10 N1 S1 119.34(14) . . ?
C1 O1 S1 113.59(13) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.76(19) . . ?
C1 C6 C7 122.18(18) . . ?
C5 C6 C7 120.02(18) . . ?
N1 C7 C6 115.64(16) . . ?
N1 C7 H7 108.5 . . ?
N1 C7 C8 102.11(15) . . ?
C6 C7 H7 108.5 . . ?
C6 C7 C8 113.18(15) . . ?
C8 C7 H7 108.5 . . ?
C9 C8 C7 102.06(15) . . ?
C11 C8 C7 110.76(15) . . ?
C11 C8 C9 111.28(17) . . ?
C12 C8 C7 110.26(16) . . ?
C12 C8 C9 113.07(17) . . ?
C12 C8 C11 109.25(16) . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C8 104.49(16) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
N1 C10 C9 102.21(16) . . ?
N1 C10 H10 110.8 . . ?
C9 C10 H10 110.8 . . ?
C13 C10 N1 111.39(17) . . ?
C13 C10 C9 110.68(19) . . ?
C13 C10 H10 110.8 . . ?
N2 C11 C8 179.4(2) . . ?
N3 C12 C8 177.7(2) . . ?
C10 C13 H13 117.3 . . ?
C14 C13 C10 125.4(3) . . ?
C14 C13 H13 117.3 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C7 C6 7.6(2) . . . . ?
S1 N1 C7 C8 130.95(14) . . . . ?
S1 N1 C10 C9 -155.09(14) . . . . ?
S1 N1 C10 C13 86.7(2) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C6 C7 N1 19.4(3) . . . . ?
C1 C6 C7 C8 -97.9(2) . . . . ?
N1 S1 O1 C1 58.93(14) . . . . ?
N1 C7 C8 C9 32.95(18) . . . . ?
N1 C7 C8 C11 -85.60(18) . . . . ?
N1 C7 C8 C12 153.35(16) . . . . ?
N1 C10 C13 C14 -126.9(3) . . . . ?
O1 S1 N1 C7 -42.79(16) . . . . ?
O1 S1 N1 C10 99.79(15) . . . . ?
O1 C1 C2 C3 179.19(19) . . . . ?
O1 C1 C6 C5 179.18(17) . . . . ?
O1 C1 C6 C7 -3.2(3) . . . . ?
O2 S1 N1 C7 71.17(16) . . . . ?
O2 S1 N1 C10 -146.25(15) . . . . ?
O2 S1 O1 C1 -55.88(15) . . . . ?
C2 C1 O1 S1 140.67(17) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C1 C6 C7 176.94(19) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
O3 S1 N1 C7 -155.61(14) . . . . ?
O3 S1 N1 C10 -13.03(18) . . . . ?
O3 S1 O1 C1 174.21(13) . . . . ?
C4 C5 C6 C1 1.8(3) . . . . ?
C4 C5 C6 C7 -175.86(19) . . . . ?
C5 C6 C7 N1 -163.06(17) . . . . ?
C5 C6 C7 C8 79.6(2) . . . . ?
C6 C1 O1 S1 -39.2(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C7 C8 C9 157.93(17) . . . . ?
C6 C7 C8 C11 39.4(2) . . . . ?
C6 C7 C8 C12 -81.7(2) . . . . ?
C7 N1 C10 C9 -10.9(2) . . . . ?
C7 N1 C10 C13 -129.1(2) . . . . ?
C7 C8 C9 C10 -40.9(2) . . . . ?
C8 C9 C10 N1 32.0(2) . . . . ?
C8 C9 C10 C13 150.76(18) . . . . ?
C9 C10 C13 C14 120.1(3) . . . . ?
C10 N1 C7 C6 -137.30(17) . . . . ?
C10 N1 C7 C8 -14.0(2) . . . . ?
C11 C8 C9 C10 77.24(19) . . . . ?
C12 C8 C9 C10 -159.35(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
