# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mx3220
_database_code_depnum_ccdc_archive 'CCDC 1444389'
_audit_update_record             
;
2015-12-27 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        (E)-2,3-diphenyl-N-tosylbut-2-enamide
_chemical_formula_moiety         'C23 H21 N O3 S'
_chemical_formula_sum            'C23 H21 N O3 S'
_chemical_formula_weight         391.47
_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                   9.710(3)
_cell_length_b                   19.200(5)
_cell_length_c                   22.065(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.104(4)
_cell_angle_gamma                90
_cell_volume                     4082.2(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11764
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4846
_cell_measurement_theta_min      0.9300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            29405
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         1.860
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             9621
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0341
_diffrn_orient_matrix_UB_12      0.0884
_diffrn_orient_matrix_UB_13      -0.0423
_diffrn_orient_matrix_UB_21      0.0183
_diffrn_orient_matrix_UB_22      0.0151
_diffrn_orient_matrix_UB_23      0.0464
_diffrn_orient_matrix_UB_31      0.0416
_diffrn_orient_matrix_UB_32      -0.0150
_diffrn_orient_matrix_UB_33      -0.0116
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7541
_reflns_number_total             9326
_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  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         9326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0870
_refine_ls_restrained_S_all      1.197
_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)+(0.0135P)²+3.8809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C11A(H11A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A),
 C21A(H21A), C22A(H22A), N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6),
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C21(H21),
  C22(H22)
2.b Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C23A(H23A,H23B,H23C), C8(H8A,H8B,H8C), C23(H23D,H23E,H23F)
;
_atom_sites_solution_hydrogens   geom
_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
S1A S 0.36934(8) 0.27681(5) 0.26825(4) 0.0397(2) Uani 1 1 d . . . . .
O1A O 0.16688(18) 0.27228(11) 0.35755(9) 0.0362(5) Uani 1 1 d . . . . .
O2A O 0.5055(2) 0.28374(14) 0.25079(10) 0.0572(7) Uani 1 1 d . . . . .
O3A O 0.2875(2) 0.21684(12) 0.24991(10) 0.0509(6) Uani 1 1 d . . . . .
N1A N 0.3944(2) 0.27954(13) 0.34378(10) 0.0335(6) Uani 1 1 d . . . . .
H1A H 0.4783 0.2813 0.3615 0.040 Uiso 1 1 calc R . . . .
C1A C 0.4561(3) 0.35264(15) 0.53352(13) 0.0283(6) Uani 1 1 d . . . . .
C2A C 0.4173(3) 0.40711(16) 0.56991(13) 0.0332(7) Uani 1 1 d . . . . .
H2A H 0.3550 0.4406 0.5529 0.040 Uiso 1 1 calc R . . . .
C3A C 0.4705(3) 0.41170(17) 0.63105(14) 0.0379(7) Uani 1 1 d . . . . .
H3A H 0.4426 0.4477 0.6550 0.046 Uiso 1 1 calc R . . . .
C4A C 0.5652(3) 0.36276(17) 0.65643(14) 0.0385(7) Uani 1 1 d . . . . .
H4A H 0.5995 0.3652 0.6976 0.046 Uiso 1 1 calc R . . . .
C5A C 0.6086(3) 0.31014(16) 0.62038(14) 0.0371(7) Uani 1 1 d . . . . .
H5A H 0.6749 0.2783 0.6371 0.044 Uiso 1 1 calc R . . . .
C6A C 0.5542(3) 0.30445(16) 0.55955(14) 0.0337(7) Uani 1 1 d . . . . .
H6A H 0.5830 0.2684 0.5359 0.040 Uiso 1 1 calc R . . . .
C7A C 0.3939(3) 0.34495(15) 0.46879(12) 0.0281(6) Uani 1 1 d . . . . .
C8A C 0.4005(3) 0.40875(15) 0.42903(13) 0.0340(7) Uani 1 1 d . . . . .
H8AA H 0.3869 0.4498 0.4525 0.051 Uiso 1 1 calc GR . . . .
H8AB H 0.3291 0.4060 0.3949 0.051 Uiso 1 1 calc GR . . . .
H8AC H 0.4896 0.4109 0.4145 0.051 Uiso 1 1 calc GR . . . .
C9A C 0.3353(3) 0.28455(15) 0.44694(13) 0.0278(6) Uani 1 1 d . . . . .
C10A C 0.3104(3) 0.21979(16) 0.48064(14) 0.0323(7) Uani 1 1 d . . . . .
C11A C 0.3191(3) 0.15558(17) 0.45273(16) 0.0441(8) Uani 1 1 d . . . . .
H11A H 0.3399 0.1537 0.4127 0.053 Uiso 1 1 calc R . . . .
C12A C 0.2974(4) 0.09439(19) 0.48303(19) 0.0549(10) Uani 1 1 d . . . . .
H12A H 0.3051 0.0519 0.4634 0.066 Uiso 1 1 calc R . . . .
C13A C 0.2647(4) 0.0955(2) 0.54177(19) 0.0573(10) Uani 1 1 d . . . . .
H13A H 0.2510 0.0542 0.5622 0.069 Uiso 1 1 calc R . . . .
C14A C 0.2524(4) 0.1590(2) 0.56988(18) 0.0561(10) Uani 1 1 d . . . . .
H14A H 0.2290 0.1604 0.6095 0.067 Uiso 1 1 calc R . . . .
C15A C 0.2744(3) 0.22056(18) 0.54000(15) 0.0438(8) Uani 1 1 d . . . . .
H15A H 0.2651 0.2629 0.5596 0.053 Uiso 1 1 calc R . . . .
C16A C 0.2883(3) 0.27918(15) 0.37963(13) 0.0288(6) Uani 1 1 d . . . . .
C17A C 0.2736(3) 0.35230(17) 0.24664(13) 0.0358(7) Uani 1 1 d . . . . .
C18A C 0.1360(3) 0.34825(18) 0.22209(14) 0.0419(8) Uani 1 1 d . . . . .
H18A H 0.0902 0.3056 0.2194 0.050 Uiso 1 1 calc R . . . .
C19A C 0.0669(3) 0.4086(2) 0.20148(15) 0.0488(9) Uani 1 1 d . . . . .
H19A H -0.0257 0.4059 0.1849 0.059 Uiso 1 1 calc R . . . .
C20A C 0.1326(4) 0.4725(2) 0.20500(15) 0.0482(9) Uani 1 1 d . . . . .
C21A C 0.2681(4) 0.47552(19) 0.23123(16) 0.0525(9) Uani 1 1 d . . . . .
H21A H 0.3127 0.5185 0.2350 0.063 Uiso 1 1 calc R . . . .
C22A C 0.3402(3) 0.41634(19) 0.25229(15) 0.0455(8) Uani 1 1 d . . . . .
H22A H 0.4320 0.4195 0.2700 0.055 Uiso 1 1 calc R . . . .
C23A C 0.0591(5) 0.5372(2) 0.1792(2) 0.0746(13) Uani 1 1 d . . . . .
H23A H 0.0583 0.5379 0.1356 0.112 Uiso 1 1 calc GR . . . .
H23B H 0.1069 0.5777 0.1966 0.112 Uiso 1 1 calc GR . . . .
H23C H -0.0345 0.5373 0.1889 0.112 Uiso 1 1 calc GR . . . .
S1 S 0.91773(8) 0.41462(4) 0.38445(4) 0.03649(19) Uani 1 1 d . . . . .
O1 O 0.67441(19) 0.31817(11) 0.38867(10) 0.0399(5) Uani 1 1 d . . . . .
O2 O 1.0524(2) 0.42963(11) 0.36804(10) 0.0448(6) Uani 1 1 d . . . . .
O3 O 0.7987(2) 0.45224(12) 0.35798(10) 0.0471(6) Uani 1 1 d . . . . .
N1 N 0.8965(2) 0.33013(13) 0.36765(11) 0.0347(6) Uani 1 1 d . . . . .
H1 H 0.9614 0.3095 0.3513 0.042 Uiso 1 1 calc R . . . .
C1 C 0.8668(3) 0.10188(16) 0.33432(14) 0.0357(7) Uani 1 1 d . . . . .
C2 C 0.9601(3) 0.07505(18) 0.38176(15) 0.0432(8) Uani 1 1 d . . . . .
H2 H 1.0016 0.1050 0.4117 0.052 Uiso 1 1 calc R . . . .
C3 C 0.9924(4) 0.00478(19) 0.38513(17) 0.0507(9) Uani 1 1 d . . . . .
H3 H 1.0547 -0.0120 0.4172 0.061 Uiso 1 1 calc R . . . .
C4 C 0.9320(4) -0.04041(19) 0.34081(17) 0.0512(9) Uani 1 1 d . . . . .
H4 H 0.9525 -0.0877 0.3434 0.061 Uiso 1 1 calc R . . . .
C5 C 0.8416(4) -0.01518(19) 0.29295(18) 0.0511(9) Uani 1 1 d . . . . .
H5 H 0.8015 -0.0454 0.2628 0.061 Uiso 1 1 calc R . . . .
C6 C 0.8101(3) 0.05517(18) 0.28957(16) 0.0438(8) Uani 1 1 d . . . . .
H6 H 0.7497 0.0717 0.2567 0.053 Uiso 1 1 calc R . . . .
C7 C 0.8331(3) 0.17775(16) 0.33075(14) 0.0348(7) Uani 1 1 d . . . . .
C8 C 0.8323(4) 0.21080(18) 0.26865(15) 0.0498(9) Uani 1 1 d . . . . .
H8A H 0.9242 0.2094 0.2569 0.075 Uiso 1 1 calc GR . . . .
H8B H 0.8023 0.2583 0.2703 0.075 Uiso 1 1 calc GR . . . .
H8C H 0.7699 0.1857 0.2393 0.075 Uiso 1 1 calc GR . . . .
C9 C 0.8062(3) 0.21388(15) 0.38008(13) 0.0306(6) Uani 1 1 d . . . . .
C10 C 0.7930(3) 0.18584(16) 0.44224(14) 0.0329(7) Uani 1 1 d . . . . .
C11 C 0.8780(3) 0.21136(18) 0.49304(15) 0.0452(8) Uani 1 1 d . . . . .
H11 H 0.9451 0.2446 0.4876 0.054 Uiso 1 1 calc R . . . .
C12 C 0.8643(4) 0.1882(2) 0.55148(16) 0.0552(10) Uani 1 1 d . . . . .
H12 H 0.9222 0.2056 0.5847 0.066 Uiso 1 1 calc R . . . .
C13 C 0.7654(4) 0.1396(2) 0.56021(17) 0.0534(10) Uani 1 1 d . . . . .
H13 H 0.7560 0.1240 0.5994 0.064 Uiso 1 1 calc R . . . .
C14 C 0.6796(4) 0.11399(19) 0.51056(19) 0.0544(10) Uani 1 1 d . . . . .
H14 H 0.6120 0.0812 0.5165 0.065 Uiso 1 1 calc R . . . .
C15 C 0.6936(3) 0.13681(17) 0.45198(16) 0.0439(8) Uani 1 1 d . . . . .
H15 H 0.6357 0.1190 0.4189 0.053 Uiso 1 1 calc R . . . .
C16 C 0.7828(3) 0.29095(16) 0.37794(13) 0.0315(7) Uani 1 1 d . . . . .
C17 C 0.9241(3) 0.41485(15) 0.46416(14) 0.0327(7) Uani 1 1 d . . . . .
C18 C 0.8063(3) 0.42781(15) 0.49194(14) 0.0340(7) Uani 1 1 d . . . . .
H18 H 0.7229 0.4389 0.4685 0.041 Uiso 1 1 calc R . . . .
C19 C 0.8137(3) 0.42419(16) 0.55459(14) 0.0361(7) Uani 1 1 d . . . . .
H19 H 0.7345 0.4332 0.5731 0.043 Uiso 1 1 calc R . . . .
C20 C 0.9365(3) 0.40742(16) 0.59095(15) 0.0368(7) Uani 1 1 d . . . . .
C21 C 1.0529(3) 0.39406(18) 0.56187(15) 0.0429(8) Uani 1 1 d . . . . .
H21 H 1.1359 0.3822 0.5853 0.052 Uiso 1 1 calc R . . . .
C22 C 1.0484(3) 0.39789(17) 0.49956(15) 0.0393(8) Uani 1 1 d . . . . .
H22 H 1.1278 0.3892 0.4811 0.047 Uiso 1 1 calc R . . . .
C23 C 0.9444(4) 0.40341(19) 0.65936(15) 0.0516(9) Uani 1 1 d . . . . .
H23D H 0.8611 0.4224 0.6721 0.077 Uiso 1 1 calc GR . . . .
H23E H 1.0230 0.4296 0.6776 0.077 Uiso 1 1 calc GR . . . .
H23F H 0.9541 0.3557 0.6721 0.077 Uiso 1 1 calc GR . . . .


_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
S1A O2A 1.429(2) . ?
S1A O3A 1.429(2) . ?
S1A N1A 1.655(2) . ?
S1A C17A 1.756(3) . ?
O1A C16A 1.226(3) . ?
N1A H1A 0.8600 . ?
N1A C16A 1.375(3) . ?
C1A C2A 1.398(4) . ?
C1A C6A 1.400(4) . ?
C1A C7A 1.488(4) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.387(4) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.383(4) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.384(4) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.385(4) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.513(4) . ?
C7A C9A 1.354(4) . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C9A C10A 1.484(4) . ?
C9A C16A 1.503(4) . ?
C10A C11A 1.385(4) . ?
C10A C15A 1.397(4) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.381(5) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.372(5) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.380(5) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.382(5) . ?
C15A H15A 0.9300 . ?
C17A C18A 1.381(4) . ?
C17A C22A 1.387(4) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.387(5) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.380(5) . ?
C20A C21A 1.372(5) . ?
C20A C23A 1.509(5) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.385(5) . ?
C22A H22A 0.9300 . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
S1 O2 1.429(2) . ?
S1 O3 1.426(2) . ?
S1 N1 1.671(3) . ?
S1 C17 1.752(3) . ?
O1 C16 1.224(3) . ?
N1 H1 0.8600 . ?
N1 C16 1.378(3) . ?
C1 C2 1.396(4) . ?
C1 C6 1.396(4) . ?
C1 C7 1.493(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.509(4) . ?
C7 C9 1.343(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.494(4) . ?
C9 C16 1.497(4) . ?
C10 C11 1.396(4) . ?
C10 C15 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(5) . ?
C15 H15 0.9300 . ?
C17 C18 1.385(4) . ?
C17 C22 1.393(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(4) . ?
C20 C21 1.391(4) . ?
C20 C23 1.504(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.372(4) . ?
C22 H22 0.9300 . ?
C23 H23D 0.9600 . ?
C23 H23E 0.9600 . ?
C23 H23F 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
O2A S1A N1A 104.06(13) . . ?
O2A S1A C17A 109.05(15) . . ?
O3A S1A O2A 119.96(15) . . ?
O3A S1A N1A 108.55(14) . . ?
O3A S1A C17A 109.36(14) . . ?
N1A S1A C17A 104.73(13) . . ?
S1A N1A H1A 118.2 . . ?
C16A N1A S1A 123.50(19) . . ?
C16A N1A H1A 118.2 . . ?
C2A C1A C6A 118.5(3) . . ?
C2A C1A C7A 121.3(3) . . ?
C6A C1A C7A 120.2(3) . . ?
C1A C2A H2A 119.6 . . ?
C3A C2A C1A 120.8(3) . . ?
C3A C2A H2A 119.6 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 120.0(3) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4A 120.1 . . ?
C3A C4A C5A 119.9(3) . . ?
C5A C4A H4A 120.1 . . ?
C4A C5A H5A 119.7 . . ?
C4A C5A C6A 120.5(3) . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A H6A 119.8 . . ?
C5A C6A C1A 120.3(3) . . ?
C5A C6A H6A 119.8 . . ?
C1A C7A C8A 115.8(2) . . ?
C9A C7A C1A 122.0(3) . . ?
C9A C7A C8A 122.2(3) . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7A C9A C10A 128.8(3) . . ?
C7A C9A C16A 118.3(3) . . ?
C10A C9A C16A 112.9(2) . . ?
C11A C10A C9A 120.0(3) . . ?
C11A C10A C15A 117.5(3) . . ?
C15A C10A C9A 122.4(3) . . ?
C10A C11A H11A 119.3 . . ?
C12A C11A C10A 121.4(3) . . ?
C12A C11A H11A 119.3 . . ?
C11A C12A H12A 119.6 . . ?
C13A C12A C11A 120.7(4) . . ?
C13A C12A H12A 119.6 . . ?
C12A C13A H13A 120.6 . . ?
C12A C13A C14A 118.8(3) . . ?
C14A C13A H13A 120.6 . . ?
C13A C14A H14A 119.5 . . ?
C13A C14A C15A 120.9(4) . . ?
C15A C14A H14A 119.5 . . ?
C10A C15A H15A 119.7 . . ?
C14A C15A C10A 120.6(3) . . ?
C14A C15A H15A 119.7 . . ?
O1A C16A N1A 121.6(3) . . ?
O1A C16A C9A 124.1(2) . . ?
N1A C16A C9A 114.2(2) . . ?
C18A C17A S1A 120.9(3) . . ?
C18A C17A C22A 120.2(3) . . ?
C22A C17A S1A 118.8(2) . . ?
C17A C18A H18A 120.4 . . ?
C17A C18A C19A 119.1(3) . . ?
C19A C18A H18A 120.4 . . ?
C18A C19A H19A 119.2 . . ?
C20A C19A C18A 121.5(3) . . ?
C20A C19A H19A 119.2 . . ?
C19A C20A C23A 121.2(4) . . ?
C21A C20A C19A 118.3(3) . . ?
C21A C20A C23A 120.5(4) . . ?
C20A C21A H21A 119.1 . . ?
C20A C21A C22A 121.7(3) . . ?
C22A C21A H21A 119.1 . . ?
C17A C22A H22A 120.4 . . ?
C21A C22A C17A 119.1(3) . . ?
C21A C22A H22A 120.4 . . ?
C20A C23A H23A 109.5 . . ?
C20A C23A H23B 109.5 . . ?
C20A C23A H23C 109.5 . . ?
H23A C23A H23B 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
O2 S1 N1 103.37(12) . . ?
O2 S1 C17 109.52(14) . . ?
O3 S1 O2 121.02(15) . . ?
O3 S1 N1 109.22(14) . . ?
O3 S1 C17 109.63(14) . . ?
N1 S1 C17 102.31(14) . . ?
S1 N1 H1 117.5 . . ?
C16 N1 S1 125.0(2) . . ?
C16 N1 H1 117.5 . . ?
C2 C1 C6 117.1(3) . . ?
C2 C1 C7 121.1(3) . . ?
C6 C1 C7 121.7(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.6(3) . . ?
C5 C6 H6 119.2 . . ?
C1 C7 C8 115.8(3) . . ?
C9 C7 C1 121.6(3) . . ?
C9 C7 C8 122.6(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 C10 127.3(3) . . ?
C7 C9 C16 121.9(3) . . ?
C10 C9 C16 110.8(2) . . ?
C11 C10 C9 120.1(3) . . ?
C15 C10 C9 121.9(3) . . ?
C15 C10 C11 117.9(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.7(3) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O1 C16 N1 121.6(3) . . ?
O1 C16 C9 123.2(3) . . ?
N1 C16 C9 115.0(2) . . ?
C18 C17 S1 121.1(2) . . ?
C18 C17 C22 120.0(3) . . ?
C22 C17 S1 118.9(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.7(3) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C21 117.7(3) . . ?
C19 C20 C23 121.6(3) . . ?
C21 C20 C23 120.7(3) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.7(3) . . ?
C22 C21 H21 119.2 . . ?
C17 C22 H22 120.3 . . ?
C21 C22 C17 119.5(3) . . ?
C21 C22 H22 120.3 . . ?
C20 C23 H23D 109.5 . . ?
C20 C23 H23E 109.5 . . ?
C20 C23 H23F 109.5 . . ?
H23D C23 H23E 109.5 . . ?
H23D C23 H23F 109.5 . . ?
H23E C23 H23F 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
N1A H1A O1 0.86 2.05 2.874(3) 160.0 .
N1 H1 O1A 0.86 2.11 2.885(3) 150.0 1_655

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
S1A N1A C16A O1A 4.8(4) . . . . ?
S1A N1A C16A C9A -177.9(2) . . . . ?
S1A C17A C18A C19A -175.3(2) . . . . ?
S1A C17A C22A C21A 175.3(2) . . . . ?
O2A S1A N1A C16A 175.6(2) . . . . ?
O2A S1A C17A C18A 139.3(3) . . . . ?
O2A S1A C17A C22A -38.0(3) . . . . ?
O3A S1A N1A C16A -55.6(3) . . . . ?
O3A S1A C17A C18A 6.4(3) . . . . ?
O3A S1A C17A C22A -171.0(2) . . . . ?
N1A S1A C17A C18A -109.8(3) . . . . ?
N1A S1A C17A C22A 72.8(3) . . . . ?
C1A C2A C3A C4A 1.2(4) . . . . ?
C1A C7A C9A C10A 5.6(4) . . . . ?
C1A C7A C9A C16A -173.8(2) . . . . ?
C2A C1A C6A C5A 1.4(4) . . . . ?
C2A C1A C7A C8A 52.8(3) . . . . ?
C2A C1A C7A C9A -127.2(3) . . . . ?
C2A C3A C4A C5A 1.3(4) . . . . ?
C3A C4A C5A C6A -2.5(5) . . . . ?
C4A C5A C6A C1A 1.1(4) . . . . ?
C6A C1A C2A C3A -2.6(4) . . . . ?
C6A C1A C7A C8A -128.0(3) . . . . ?
C6A C1A C7A C9A 51.9(4) . . . . ?
C7A C1A C2A C3A 176.6(3) . . . . ?
C7A C1A C6A C5A -177.8(3) . . . . ?
C7A C9A C10A C11A -146.3(3) . . . . ?
C7A C9A C10A C15A 35.4(4) . . . . ?
C7A C9A C16A O1A -115.1(3) . . . . ?
C7A C9A C16A N1A 67.6(3) . . . . ?
C8A C7A C9A C10A -174.5(3) . . . . ?
C8A C7A C9A C16A 6.1(4) . . . . ?
C9A C10A C11A C12A 179.6(3) . . . . ?
C9A C10A C15A C14A -179.8(3) . . . . ?
C10A C9A C16A O1A 65.4(4) . . . . ?
C10A C9A C16A N1A -111.9(3) . . . . ?
C10A C11A C12A C13A 0.9(5) . . . . ?
C11A C10A C15A C14A 1.8(5) . . . . ?
C11A C12A C13A C14A 0.6(6) . . . . ?
C12A C13A C14A C15A -0.9(6) . . . . ?
C13A C14A C15A C10A -0.4(5) . . . . ?
C15A C10A C11A C12A -2.1(5) . . . . ?
C16A C9A C10A C11A 33.2(4) . . . . ?
C16A C9A C10A C15A -145.1(3) . . . . ?
C17A S1A N1A C16A 61.1(3) . . . . ?
C17A C18A C19A C20A 0.0(5) . . . . ?
C18A C17A C22A C21A -2.0(5) . . . . ?
C18A C19A C20A C21A -1.9(5) . . . . ?
C18A C19A C20A C23A 176.4(3) . . . . ?
C19A C20A C21A C22A 1.8(5) . . . . ?
C20A C21A C22A C17A 0.1(5) . . . . ?
C22A C17A C18A C19A 2.0(5) . . . . ?
C23A C20A C21A C22A -176.5(3) . . . . ?
S1 N1 C16 O1 15.6(4) . . . . ?
S1 N1 C16 C9 -159.6(2) . . . . ?
S1 C17 C18 C19 176.8(2) . . . . ?
S1 C17 C22 C21 -176.4(3) . . . . ?
O2 S1 N1 C16 177.3(2) . . . . ?
O2 S1 C17 C18 155.6(2) . . . . ?
O2 S1 C17 C22 -28.0(3) . . . . ?
O3 S1 N1 C16 -52.6(3) . . . . ?
O3 S1 C17 C18 20.6(3) . . . . ?
O3 S1 C17 C22 -163.0(2) . . . . ?
N1 S1 C17 C18 -95.2(3) . . . . ?
N1 S1 C17 C22 81.2(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C7 C9 C10 -5.7(4) . . . . ?
C1 C7 C9 C16 175.4(2) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C2 C1 C7 C8 134.6(3) . . . . ?
C2 C1 C7 C9 -45.0(4) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C6 C1 C2 C3 -1.6(4) . . . . ?
C6 C1 C7 C8 -43.3(4) . . . . ?
C6 C1 C7 C9 137.1(3) . . . . ?
C7 C1 C2 C3 -179.6(3) . . . . ?
C7 C1 C6 C5 179.9(3) . . . . ?
C7 C9 C10 C11 122.8(3) . . . . ?
C7 C9 C10 C15 -60.1(4) . . . . ?
C7 C9 C16 O1 119.1(3) . . . . ?
C7 C9 C16 N1 -65.8(4) . . . . ?
C8 C7 C9 C10 174.7(3) . . . . ?
C8 C7 C9 C16 -4.2(4) . . . . ?
C9 C10 C11 C12 177.5(3) . . . . ?
C9 C10 C15 C14 -177.1(3) . . . . ?
C10 C9 C16 O1 -59.9(4) . . . . ?
C10 C9 C16 N1 115.1(3) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C10 C15 C14 0.0(5) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
C15 C10 C11 C12 0.4(5) . . . . ?
C16 C9 C10 C11 -58.1(3) . . . . ?
C16 C9 C10 C15 118.9(3) . . . . ?
C17 S1 N1 C16 63.6(3) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C17 C22 C21 0.1(5) . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C18 C19 C20 C23 -179.9(3) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C21 C22 C17 -0.7(5) . . . . ?
C22 C17 C18 C19 0.4(5) . . . . ?
C23 C20 C21 C22 -179.5(3) . . . . ?

####################################################################### 
# 
# 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_sa3798
_database_code_depnum_ccdc_archive 'CCDC 1444390'
_audit_update_record             
;
2015-12-27 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;
_audit_creation_date             2014-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        (E)-2-(naphthalen-2-yl)-N-tosylhept-2-enamide
_chemical_formula_moiety         'C24 H25 N O3 S'
_chemical_formula_sum            'C24 H25 N O3 S'
_chemical_formula_weight         407.51
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3077(19)
_cell_length_b                   11.580(2)
_cell_length_c                   11.683(2)
_cell_angle_alpha                116.41(3)
_cell_angle_beta                 100.50(3)
_cell_angle_gamma                90.85(3)
_cell_volume                     1102.3(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    298.1500
_cell_measurement_theta_max      27.4814
_cell_measurement_theta_min      2.2387
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9421
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.664
_diffrn_ambient_temperature      298.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             4961
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0123
_diffrn_orient_matrix_UB_12      0.0915
_diffrn_orient_matrix_UB_13      0.0596
_diffrn_orient_matrix_UB_21      0.0946
_diffrn_orient_matrix_UB_22      0.0162
_diffrn_orient_matrix_UB_23      0.0142
_diffrn_orient_matrix_UB_31      0.0426
_diffrn_orient_matrix_UB_32      0.0673
_diffrn_orient_matrix_UB_33      -0.0566
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3979
_reflns_number_total             4952
_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., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution    
;
 'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.129
_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)+(0.0575P)²+0.2606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1520
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_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 0.97923(6) 0.31248(5) 0.03169(6) 0.05495(18) Uani 1 1 d . . . . .
O1 O 1.06807(18) 0.37358(15) -0.01811(19) 0.0703(5) Uani 1 1 d . . . . .
O2 O 1.04771(19) 0.27749(16) 0.12914(18) 0.0730(5) Uani 1 1 d . . . . .
O3 O 0.7252(2) 0.28746(15) 0.13439(18) 0.0706(5) Uani 1 1 d . . . . .
N1 N 0.8617(2) 0.41904(16) 0.09065(19) 0.0552(5) Uani 1 1 d . . . . .
H1 H 0.8733 0.4935 0.0920 0.066 Uiso 1 1 calc R . . . .
C1 C 0.6054(5) -0.1548(4) -0.4176(4) 0.1346(16) Uani 1 1 d . . . . .
H1A H 0.6397 -0.2330 -0.4189 0.202 Uiso 1 1 calc GR . . . .
H1B H 0.6106 -0.1536 -0.4985 0.202 Uiso 1 1 calc GR . . . .
H1C H 0.5055 -0.1513 -0.4069 0.202 Uiso 1 1 calc GR . . . .
C2 C 0.7008(3) -0.0387(3) -0.3051(3) 0.0814(8) Uani 1 1 d . . . . .
C3 C 0.7644(3) -0.0423(2) -0.1912(3) 0.0776(8) Uani 1 1 d . . . . .
H3 H 0.7505 -0.1183 -0.1839 0.093 Uiso 1 1 calc R . . . .
C4 C 0.8487(3) 0.0645(2) -0.0871(3) 0.0625(6) Uani 1 1 d . . . . .
H4 H 0.8901 0.0607 -0.0103 0.075 Uiso 1 1 calc R . . . .
C5 C 0.8707(2) 0.1766(2) -0.0981(2) 0.0527(5) Uani 1 1 d . . . . .
C6 C 0.8086(3) 0.1824(3) -0.2120(3) 0.0700(7) Uani 1 1 d . . . . .
H6 H 0.8235 0.2581 -0.2195 0.084 Uiso 1 1 calc R . . . .
C7 C 0.7243(3) 0.0750(3) -0.3143(3) 0.0869(9) Uani 1 1 d . . . . .
H7 H 0.6825 0.0789 -0.3909 0.104 Uiso 1 1 calc R . . . .
C8 C 0.7456(2) 0.3926(2) 0.1378(2) 0.0516(5) Uani 1 1 d . . . . .
C9 C 0.6477(2) 0.49757(19) 0.1862(2) 0.0483(5) Uani 1 1 d . . . . .
C10 C 0.5156(2) 0.4607(2) 0.1952(2) 0.0556(5) Uani 1 1 d . . . . .
H10 H 0.4944 0.3722 0.1666 0.067 Uiso 1 1 calc R . . . .
C11 C 0.3983(2) 0.5422(2) 0.2449(2) 0.0600(6) Uani 1 1 d . . . . .
H11A H 0.3150 0.5224 0.1733 0.072 Uiso 1 1 calc R . . . .
H11B H 0.4345 0.6329 0.2801 0.072 Uiso 1 1 calc R . . . .
C12 C 0.3491(3) 0.5189(3) 0.3505(3) 0.0662(6) Uani 1 1 d . . . . .
H12A H 0.3167 0.4273 0.3150 0.079 Uiso 1 1 calc R . . . .
H12B H 0.4331 0.5399 0.4218 0.079 Uiso 1 1 calc R . . . .
C13 C 0.2275(3) 0.5955(3) 0.4045(3) 0.0776(7) Uani 1 1 d . . . . .
H13A H 0.2592 0.6872 0.4400 0.093 Uiso 1 1 calc R . . . .
H13B H 0.1426 0.5739 0.3338 0.093 Uiso 1 1 calc R . . . .
C14 C 0.1834(5) 0.5703(4) 0.5093(4) 0.1264(14) Uani 1 1 d . . . . .
H14A H 0.1559 0.4791 0.4759 0.190 Uiso 1 1 calc GR . . . .
H14B H 0.1015 0.6170 0.5362 0.190 Uiso 1 1 calc GR . . . .
H14C H 0.2645 0.5986 0.5828 0.190 Uiso 1 1 calc GR . . . .
C15 C 0.7008(2) 0.63255(18) 0.2192(2) 0.0451(4) Uani 1 1 d . . . . .
C16 C 0.8337(2) 0.6939(2) 0.3116(2) 0.0534(5) Uani 1 1 d . . . . .
H16 H 0.8853 0.6503 0.3534 0.064 Uiso 1 1 calc R . . . .
C17 C 0.8871(3) 0.8162(2) 0.3399(2) 0.0571(5) Uani 1 1 d . . . . .
H17 H 0.9747 0.8546 0.4007 0.068 Uiso 1 1 calc R . . . .
C18 C 0.8114(2) 0.88548(19) 0.2784(2) 0.0513(5) Uani 1 1 d . . . . .
C19 C 0.6761(2) 0.82709(19) 0.1889(2) 0.0502(5) Uani 1 1 d . . . . .
C20 C 0.6245(2) 0.69961(19) 0.1612(2) 0.0489(5) Uani 1 1 d . . . . .
H20 H 0.5361 0.6603 0.1018 0.059 Uiso 1 1 calc R . . . .
C21 C 0.5989(3) 0.8955(2) 0.1280(3) 0.0697(7) Uani 1 1 d . . . . .
H21 H 0.5088 0.8588 0.0707 0.084 Uiso 1 1 calc R . . . .
C22 C 0.6558(4) 1.0153(3) 0.1526(3) 0.0822(8) Uani 1 1 d . . . . .
H22 H 0.6038 1.0599 0.1123 0.099 Uiso 1 1 calc R . . . .
C23 C 0.7915(4) 1.0718(2) 0.2378(3) 0.0784(8) Uani 1 1 d . . . . .
H23 H 0.8302 1.1527 0.2518 0.094 Uiso 1 1 calc R . . . .
C24 C 0.8670(3) 1.0101(2) 0.3000(3) 0.0683(7) Uani 1 1 d . . . . .
H24 H 0.9564 1.0495 0.3576 0.082 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 O1 1.4308(17) . ?
S1 O2 1.4213(18) . ?
S1 N1 1.6586(19) . ?
S1 C5 1.751(2) . ?
O3 C8 1.211(2) . ?
N1 C8 1.387(3) . ?
C1 C2 1.513(4) . ?
C2 C3 1.374(4) . ?
C2 C7 1.385(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.375(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.377(4) . ?
C8 C9 1.496(3) . ?
C9 C10 1.333(3) . ?
C9 C15 1.486(3) . ?
C10 C11 1.481(3) . ?
C11 C12 1.518(3) . ?
C12 C13 1.502(4) . ?
C13 C14 1.501(4) . ?
C15 C16 1.416(3) . ?
C15 C20 1.370(3) . ?
C16 C17 1.365(3) . ?
C17 C18 1.415(3) . ?
C18 C19 1.415(3) . ?
C18 C24 1.421(3) . ?
C19 C20 1.418(3) . ?
C19 C21 1.408(3) . ?
C21 C22 1.361(3) . ?
C22 C23 1.397(4) . ?
C23 C24 1.351(4) . ?

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 103.47(9) . . ?
O1 S1 C5 109.73(11) . . ?
O2 S1 O1 119.16(12) . . ?
O2 S1 N1 109.44(11) . . ?
O2 S1 C5 109.08(11) . . ?
N1 S1 C5 104.96(10) . . ?
C8 N1 S1 122.47(14) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 C7 118.3(3) . . ?
C7 C2 C1 120.4(3) . . ?
C2 C3 C4 121.4(3) . . ?
C5 C4 C3 119.4(3) . . ?
C4 C5 S1 120.23(19) . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 S1 119.48(18) . . ?
C7 C6 C5 119.3(3) . . ?
C6 C7 C2 121.2(3) . . ?
O3 C8 N1 120.0(2) . . ?
O3 C8 C9 123.6(2) . . ?
N1 C8 C9 116.33(17) . . ?
C10 C9 C8 115.89(19) . . ?
C10 C9 C15 124.66(19) . . ?
C15 C9 C8 119.45(18) . . ?
C9 C10 C11 128.4(2) . . ?
C10 C11 C12 111.07(19) . . ?
C13 C12 C11 114.7(2) . . ?
C14 C13 C12 112.9(3) . . ?
C16 C15 C9 119.89(18) . . ?
C20 C15 C9 121.40(19) . . ?
C20 C15 C16 118.70(19) . . ?
C17 C16 C15 120.8(2) . . ?
C16 C17 C18 121.2(2) . . ?
C17 C18 C24 122.9(2) . . ?
C19 C18 C17 118.70(19) . . ?
C19 C18 C24 118.4(2) . . ?
C18 C19 C20 118.55(19) . . ?
C21 C19 C18 119.3(2) . . ?
C21 C19 C20 122.2(2) . . ?
C15 C20 C19 122.0(2) . . ?
C22 C21 C19 120.3(3) . . ?
C21 C22 C23 120.7(3) . . ?
C24 C23 C22 120.6(2) . . ?
C23 C24 C18 120.7(2) . . ?

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 C8 O3 -1.6(3) . . . . ?
S1 N1 C8 C9 -179.19(15) . . . . ?
S1 C5 C6 C7 179.5(2) . . . . ?
O1 S1 N1 C8 173.77(18) . . . . ?
O1 S1 C5 C4 140.07(19) . . . . ?
O1 S1 C5 C6 -39.4(2) . . . . ?
O2 S1 N1 C8 -58.2(2) . . . . ?
O2 S1 C5 C4 7.9(2) . . . . ?
O2 S1 C5 C6 -171.55(19) . . . . ?
O3 C8 C9 C10 -16.4(3) . . . . ?
O3 C8 C9 C15 164.2(2) . . . . ?
N1 S1 C5 C4 -109.33(19) . . . . ?
N1 S1 C5 C6 71.3(2) . . . . ?
N1 C8 C9 C10 161.2(2) . . . . ?
N1 C8 C9 C15 -18.3(3) . . . . ?
C1 C2 C3 C4 -178.4(3) . . . . ?
C1 C2 C7 C6 178.8(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C2 C7 C6 -0.4(5) . . . . ?
C3 C4 C5 S1 -179.10(19) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 S1 N1 C8 58.7(2) . . . . ?
C5 C6 C7 C2 0.0(4) . . . . ?
C7 C2 C3 C4 0.7(4) . . . . ?
C8 C9 C10 C11 177.0(2) . . . . ?
C8 C9 C15 C16 -55.9(3) . . . . ?
C8 C9 C15 C20 123.5(2) . . . . ?
C9 C10 C11 C12 -126.6(3) . . . . ?
C9 C15 C16 C17 177.7(2) . . . . ?
C9 C15 C20 C19 -178.07(19) . . . . ?
C10 C9 C15 C16 124.6(2) . . . . ?
C10 C9 C15 C20 -56.0(3) . . . . ?
C10 C11 C12 C13 -178.6(2) . . . . ?
C11 C12 C13 C14 -179.5(3) . . . . ?
C15 C9 C10 C11 -3.6(4) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C15 C20 C19 1.3(3) . . . . ?
C16 C17 C18 C19 1.8(3) . . . . ?
C16 C17 C18 C24 -176.6(2) . . . . ?
C17 C18 C19 C20 -2.2(3) . . . . ?
C17 C18 C19 C21 179.4(2) . . . . ?
C17 C18 C24 C23 179.2(2) . . . . ?
C18 C19 C20 C15 0.6(3) . . . . ?
C18 C19 C21 C22 1.6(4) . . . . ?
C19 C18 C24 C23 0.8(4) . . . . ?
C19 C21 C22 C23 0.3(5) . . . . ?
C20 C15 C16 C17 -1.7(3) . . . . ?
C20 C19 C21 C22 -176.8(2) . . . . ?
C21 C19 C20 C15 179.0(2) . . . . ?
C21 C22 C23 C24 -1.7(5) . . . . ?
C22 C23 C24 C18 1.1(4) . . . . ?
C24 C18 C19 C20 176.3(2) . . . . ?
C24 C18 C19 C21 -2.1(3) . . . . ?

