# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1577443'
_audit_update_record             
;
2017-10-01 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        '(E)-1-phenyl-2-tosylethanone oxime'
_chemical_name_common            ?
_chemical_melting_point          474.16-475.16
_chemical_formula_moiety         289.34
_chemical_formula_sum            'C15 H15 N O3 S'
_chemical_formula_weight         289.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2479(4)
_cell_length_b                   5.55410(10)
_cell_length_c                   16.8079(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.501(2)
_cell_angle_gamma                90
_cell_volume                     1416.88(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    2997
_cell_measurement_theta_min      5.2760
_cell_measurement_theta_max      71.1430

_exptl_crystal_description       block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.093
_shelx_estimated_absorpt_T_min   0.668
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_T_min  0.62985
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            4536
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.288
_diffrn_reflns_theta_max         70.896
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2663
_reflns_number_gt                2396
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0632P)²+0.2660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2663
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
S1 S 0.28795(3) 0.70321(8) 0.57223(2) 0.04824(16) Uani 1 1 d . . . . .
O3 O 0.33841(9) 0.5926(3) 0.51452(7) 0.0662(4) Uani 1 1 d . . . . .
O2 O 0.27400(10) 0.9582(3) 0.56853(9) 0.0730(4) Uani 1 1 d . . . . .
O1 O 0.06706(10) 0.9114(3) 0.57334(7) 0.0763(5) Uani 1 1 d . . . . .
H1 H 0.0303 1.0194 0.5713 0.115 Uiso 1 1 calc R U . . .
N1 N 0.06756(10) 0.8058(3) 0.49811(8) 0.0542(4) Uani 1 1 d . . . . .
C4 C 0.12890(10) 0.5227(3) 0.41572(9) 0.0416(3) Uani 1 1 d . . . . .
C9 C 0.33447(10) 0.6277(3) 0.66912(9) 0.0415(3) Uani 1 1 d . . . . .
C7 C 0.12402(10) 0.6374(3) 0.49467(9) 0.0426(3) Uani 1 1 d . . . . .
C8 C 0.18238(10) 0.5578(3) 0.56732(9) 0.0463(4) Uani 1 1 d . . . . .
H8A H 0.1904 0.3847 0.5655 0.056 Uiso 1 1 calc R U . . .
H8B H 0.1541 0.5957 0.6151 0.056 Uiso 1 1 calc R U . . .
C12 C 0.40458(10) 0.5059(3) 0.82203(9) 0.0485(4) Uani 1 1 d . . . . .
C14 C 0.32193(11) 0.7790(3) 0.73245(11) 0.0483(4) Uani 1 1 d . . . . .
H14 H 0.2899 0.9206 0.7239 0.058 Uiso 1 1 calc R U . . .
C10 C 0.38174(11) 0.4169(3) 0.68097(10) 0.0479(4) Uani 1 1 d . . . . .
H10 H 0.3901 0.3158 0.6382 0.058 Uiso 1 1 calc R U . . .
C13 C 0.35740(12) 0.7177(3) 0.80835(10) 0.0514(4) Uani 1 1 d . . . . .
H13 H 0.3496 0.8198 0.8509 0.062 Uiso 1 1 calc R U . . .
C11 C 0.41642(11) 0.3586(3) 0.75738(10) 0.0507(4) Uani 1 1 d . . . . .
H11 H 0.4485 0.2170 0.7657 0.061 Uiso 1 1 calc R U . . .
C5 C 0.08598(13) 0.6273(4) 0.34731(10) 0.0559(4) Uani 1 1 d . . . . .
H5 H 0.0548 0.7698 0.3518 0.067 Uiso 1 1 calc R U . . .
C3 C 0.17565(13) 0.3135(3) 0.40664(13) 0.0597(5) Uani 1 1 d . . . . .
H3 H 0.2059 0.2408 0.4510 0.072 Uiso 1 1 calc R U . . .
C1 C 0.13456(15) 0.3163(4) 0.26537(14) 0.0739(6) Uani 1 1 d . . . . .
H1A H 0.1364 0.2464 0.2153 0.089 Uiso 1 1 calc R U . . .
C6 C 0.08890(15) 0.5237(4) 0.27316(11) 0.0701(6) Uani 1 1 d . . . . .
H6 H 0.0595 0.5959 0.2283 0.084 Uiso 1 1 calc R U . . .
C2 C 0.17774(15) 0.2109(4) 0.33137(16) 0.0761(7) Uani 1 1 d . . . . .
H2 H 0.2089 0.0689 0.3259 0.091 Uiso 1 1 calc R U . . .
C15 C 0.44249(15) 0.4378(5) 0.90498(12) 0.0765(6) Uani 1 1 d . . . . .
H15A H 0.4626 0.5800 0.9336 0.115 Uiso 1 1 calc R U . . .
H15B H 0.4911 0.3295 0.9016 0.115 Uiso 1 1 calc R U . . .
H15C H 0.3979 0.3604 0.9326 0.115 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
S1 O2 1.4329(15) . ?
S1 O3 1.4330(14) . ?
S1 C9 1.7633(15) . ?
S1 C8 1.7958(16) . ?
O1 N1 1.3946(17) . ?
O1 H1 0.8200 . ?
N1 C7 1.276(2) . ?
C4 C3 1.380(2) . ?
C4 C5 1.394(2) . ?
C4 C7 1.480(2) . ?
C9 C10 1.380(2) . ?
C9 C14 1.384(2) . ?
C7 C8 1.5067(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 C11 1.386(2) . ?
C12 C13 1.386(3) . ?
C12 C15 1.505(2) . ?
C14 C13 1.380(2) . ?
C14 H14 0.9300 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C5 C6 1.377(2) . ?
C5 H5 0.9300 . ?
C3 C2 1.391(3) . ?
C3 H3 0.9300 . ?
C1 C6 1.359(3) . ?
C1 C2 1.366(4) . ?
C1 H1A 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O2 S1 O3 118.78(9) . . ?
O2 S1 C9 108.67(8) . . ?
O3 S1 C9 109.19(8) . . ?
O2 S1 C8 108.30(9) . . ?
O3 S1 C8 108.25(9) . . ?
C9 S1 C8 102.42(7) . . ?
N1 O1 H1 109.5 . . ?
C7 N1 O1 114.30(13) . . ?
C3 C4 C5 117.81(15) . . ?
C3 C4 C7 122.19(15) . . ?
C5 C4 C7 120.01(14) . . ?
C10 C9 C14 120.88(14) . . ?
C10 C9 S1 119.57(12) . . ?
C14 C9 S1 119.54(12) . . ?
N1 C7 C4 116.62(13) . . ?
N1 C7 C8 121.80(14) . . ?
C4 C7 C8 121.57(14) . . ?
C7 C8 S1 111.25(11) . . ?
C7 C8 H8A 109.4 . . ?
S1 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
S1 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C11 C12 C13 118.38(15) . . ?
C11 C12 C15 120.70(17) . . ?
C13 C12 C15 120.91(17) . . ?
C13 C14 C9 119.38(15) . . ?
C13 C14 H14 120.3 . . ?
C9 C14 H14 120.3 . . ?
C9 C10 C11 118.81(15) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C14 C13 C12 120.92(16) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C10 C11 C12 121.62(15) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C6 C5 C4 121.26(18) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C3 C2 120.20(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C6 C1 C2 119.77(18) . . ?
C6 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C1 C6 C5 120.2(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C1 C2 C3 120.78(19) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O2 S1 C9 C10 -157.43(14) . . . . ?
O3 S1 C9 C10 -26.45(16) . . . . ?
C8 S1 C9 C10 88.13(14) . . . . ?
O2 S1 C9 C14 23.56(16) . . . . ?
O3 S1 C9 C14 154.53(14) . . . . ?
C8 S1 C9 C14 -90.88(15) . . . . ?
O1 N1 C7 C4 -178.60(15) . . . . ?
O1 N1 C7 C8 1.9(3) . . . . ?
C3 C4 C7 N1 -168.59(17) . . . . ?
C5 C4 C7 N1 11.9(2) . . . . ?
C3 C4 C7 C8 11.0(2) . . . . ?
C5 C4 C7 C8 -168.50(16) . . . . ?
N1 C7 C8 S1 -96.02(18) . . . . ?
C4 C7 C8 S1 84.45(17) . . . . ?
O2 S1 C8 C7 54.57(14) . . . . ?
O3 S1 C8 C7 -75.44(14) . . . . ?
C9 S1 C8 C7 169.28(12) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
S1 C9 C14 C13 179.11(13) . . . . ?
C14 C9 C10 C11 0.1(2) . . . . ?
S1 C9 C10 C11 -178.91(13) . . . . ?
C9 C14 C13 C12 -0.6(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C15 C12 C13 C14 -179.37(18) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C13 C12 C11 C10 -0.7(3) . . . . ?
C15 C12 C11 C10 179.57(18) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C7 C4 C5 C6 -179.55(18) . . . . ?
C5 C4 C3 C2 -1.1(3) . . . . ?
C7 C4 C3 C2 179.41(17) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C4 C3 C2 C1 0.7(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
O1 H1 N1 0.82 2.05 2.7661(19) 146.0 3_576

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Petroleum ether'
