# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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data_new
_audit_creation_date             2014-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        4-hydroxy-3-methoxy-N-phenylbenzothioamide
_chemical_formula_moiety         'C14 H13 N O2 S'
_chemical_formula_sum            'C14 H13 N O2 S'
_chemical_formula_weight         259.31
_chemical_absolute_configuration ?
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.7799(16)
_cell_length_b                   12.8970(16)
_cell_length_c                   7.5173(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.827(10)
_cell_angle_gamma                90
_cell_volume                     1220.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3890
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7068
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.659
_diffrn_reflns_theta_min         2.260
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                2494
_reflns_number_total             2641
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1080 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0459P)²+0.1112P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0866
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, H11 of C11, H14 of C14, H9 of C9, H3 of C3, H8 of C8, H7
  of C7, H13 of C13, H12 of C12
 At 1.5 times of:
  All C(H,H,H) groups, H1 of C14
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.49486(6) 0.33504(5) 0.77053(8) 0.0399(2) Uani 1 1 d . . . . .
O1 O 0.8524(2) 0.3755(2) 0.2242(3) 0.0562(6) Uani 1 1 d . . . . .
O2 O 0.88064(17) 0.34993(19) 0.5839(3) 0.0496(5) Uani 1 1 d . . . . .
N1 N 0.41690(17) 0.44857(18) 0.4838(3) 0.0342(5) Uani 1 1 d . . . . .
H1A H 0.4294 0.4810 0.3897 0.041 Uiso 1 1 calc R . . . .
C1 C 0.7667(2) 0.3742(2) 0.3098(4) 0.0387(6) Uani 1 1 d . . . . .
C2 C 0.7783(2) 0.3636(2) 0.4974(4) 0.0359(6) Uani 1 1 d . . . . .
C3 C 0.6906(2) 0.3677(2) 0.5803(3) 0.0338(5) Uani 1 1 d . . . . .
H3 H 0.6986 0.3610 0.7051 0.041 Uiso 1 1 calc R . . . .
C4 C 0.5895(2) 0.38163(18) 0.4782(3) 0.0303(5) Uani 1 1 d . . . . .
C5 C 0.4958(2) 0.39036(19) 0.5704(3) 0.0309(5) Uani 1 1 d . . . . .
C6 C 0.3137(2) 0.4631(2) 0.5297(3) 0.0326(5) Uani 1 1 d . . . . .
C7 C 0.2495(3) 0.3797(2) 0.5519(4) 0.0398(6) Uani 1 1 d . . . . .
H7 H 0.2745 0.3124 0.5447 0.048 Uiso 1 1 calc R . . . .
C8 C 0.1477(2) 0.3968(3) 0.5850(4) 0.0449(7) Uani 1 1 d . . . . .
H8 H 0.1042 0.3408 0.5997 0.054 Uiso 1 1 calc R . . . .
C9 C 0.1106(2) 0.4962(3) 0.5962(4) 0.0454(7) Uani 1 1 d . . . . .
H9 H 0.0422 0.5073 0.6188 0.054 Uiso 1 1 calc R . . . .
C10 C 0.8972(3) 0.3427(3) 0.7740(5) 0.0550(9) Uani 1 1 d . . . . .
H10A H 0.8704 0.4039 0.8232 0.082 Uiso 1 1 calc GR . . . .
H10B H 0.9718 0.3361 0.8193 0.082 Uiso 1 1 calc GR . . . .
H10C H 0.8607 0.2829 0.8088 0.082 Uiso 1 1 calc GR . . . .
C11 C 0.5793(2) 0.3885(2) 0.2910(3) 0.0367(6) Uani 1 1 d . . . . .
H11 H 0.5122 0.3959 0.2212 0.044 Uiso 1 1 calc R . . . .
C12 C 0.6671(2) 0.3846(2) 0.2087(4) 0.0406(7) Uani 1 1 d . . . . .
H12 H 0.6592 0.3889 0.0836 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2763(2) 0.5631(2) 0.5381(4) 0.0397(6) Uani 1 1 d . . . . .
H13 H 0.3189 0.6192 0.5199 0.048 Uiso 1 1 calc R . . . .
C14 C 0.1747(3) 0.5794(3) 0.5739(4) 0.0461(7) Uani 1 1 d . . . . .
H14 H 0.1498 0.6466 0.5829 0.055 Uiso 1 1 calc R . . . .
H1 H 0.897(4) 0.355(4) 0.294(6) 0.069 Uiso 1 1 d 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 C5 1.667(3) . ?
O1 C1 1.362(3) . ?
O1 H1 0.75(5) . ?
O2 C2 1.369(4) . ?
O2 C10 1.412(4) . ?
N1 H1A 0.8600 . ?
N1 C5 1.335(3) . ?
N1 C6 1.431(3) . ?
C1 C2 1.399(4) . ?
C1 C12 1.372(4) . ?
C2 C3 1.373(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(4) . ?
C4 C5 1.487(4) . ?
C4 C11 1.393(4) . ?
C6 C7 1.380(4) . ?
C6 C13 1.381(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(5) . ?
C9 H9 0.9300 . ?
C9 C14 1.377(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.373(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.385(4) . ?
C14 H14 0.9300 . ?

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
C1 O1 H1 104(4) . . ?
C2 O2 C10 117.1(2) . . ?
C5 N1 H1A 116.3 . . ?
C5 N1 C6 127.3(2) . . ?
C6 N1 H1A 116.3 . . ?
O1 C1 C2 121.4(3) . . ?
O1 C1 C12 118.8(3) . . ?
C12 C1 C2 119.8(2) . . ?
O2 C2 C1 114.8(2) . . ?
O2 C2 C3 125.2(3) . . ?
C3 C2 C1 119.9(2) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.7(2) . . ?
C11 C4 C3 118.8(2) . . ?
C11 C4 C5 121.5(2) . . ?
N1 C5 S1 124.1(2) . . ?
N1 C5 C4 114.6(2) . . ?
C4 C5 S1 121.28(19) . . ?
C7 C6 N1 121.3(2) . . ?
C7 C6 C13 120.3(3) . . ?
C13 C6 N1 118.3(2) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C14 120.0(3) . . ?
C14 C9 H9 120.0 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11 119.7 . . ?
C12 C11 C4 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C1 C12 C11 120.4(2) . . ?
C1 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C6 C13 H13 120.2 . . ?
C6 C13 C14 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 120.1(3) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?

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
C12 H12 S1 0.93 2.96 3.692(3) 136.9 1_554
O1 H1 O2 0.75(5) 2.22(5) 2.686(4) 121(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
O1 C1 C2 O2 -3.1(4) . . . . ?
O1 C1 C2 C3 176.8(2) . . . . ?
O1 C1 C12 C11 -176.9(3) . . . . ?
O2 C2 C3 C4 -179.8(3) . . . . ?
N1 C6 C7 C8 -175.9(2) . . . . ?
N1 C6 C13 C14 177.0(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C1 C12 C11 2.4(4) . . . . ?
C2 C3 C4 C5 -177.4(2) . . . . ?
C2 C3 C4 C11 1.7(4) . . . . ?
C3 C4 C5 S1 -27.2(3) . . . . ?
C3 C4 C5 N1 150.2(2) . . . . ?
C3 C4 C11 C12 -1.8(4) . . . . ?
C4 C11 C12 C1 -0.3(4) . . . . ?
C5 N1 C6 C7 -54.3(4) . . . . ?
C5 N1 C6 C13 130.5(3) . . . . ?
C5 C4 C11 C12 177.3(2) . . . . ?
C6 N1 C5 S1 -9.2(4) . . . . ?
C6 N1 C5 C4 173.5(2) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C6 C13 C14 C9 -1.7(4) . . . . ?
C7 C6 C13 C14 1.8(4) . . . . ?
C7 C8 C9 C14 0.2(5) . . . . ?
C8 C9 C14 C13 0.7(4) . . . . ?
C10 O2 C2 C1 177.8(3) . . . . ?
C10 O2 C2 C3 -2.1(4) . . . . ?
C11 C4 C5 S1 153.7(2) . . . . ?
C11 C4 C5 N1 -28.9(3) . . . . ?
C12 C1 C2 O2 177.7(3) . . . . ?
C12 C1 C2 C3 -2.5(4) . . . . ?
C13 C6 C7 C8 -0.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethylacetate:pet ether'
_database_code_depnum_ccdc_archive 'CCDC 1021399'
