# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  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_fbp1517

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_structural     C21H21NO2S
_chemical_formula_sum            'C21 H21 N O2 S'
_chemical_formula_weight         351.45

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'

_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                   15.9577(7)
_cell_length_b                   6.3713(3)
_cell_length_c                   17.8868(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.0337(15)
_cell_angle_gamma                90
_cell_volume                     1804.89(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9793
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      34.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.193
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2012/1 (Sheldrick)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            75519
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         34.968
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7935
_reflns_number_gt                6901
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT V8.34A'
_computing_data_reduction        'Bruker SAINT V8.34A'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7935
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.001
_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 0.76168(2) 0.72154(3) 0.26160(2) 0.01561(6) Uani 1 1 d . . . . .
O1 O 0.58926(4) 1.09176(8) 0.35244(3) 0.01876(11) Uani 1 1 d . . . . .
O2 O 0.57811(4) 0.77847(9) 0.49715(3) 0.01590(11) Uani 1 1 d . . . . .
N1 N 0.62237(4) 0.73691(9) 0.32750(3) 0.01164(10) Uani 1 1 d . . . . .
C1 C 0.61026(4) 0.91290(10) 0.36943(4) 0.01268(12) Uani 1 1 d . . . . .
C2 C 0.63504(4) 0.79364(10) 0.44375(4) 0.01252(12) Uani 1 1 d . . . . .
H2 H 0.6906 0.8464 0.4685 0.015 Uiso 1 1 calc R U . . .
C3 C 0.64965(4) 0.59906(10) 0.39208(3) 0.01102(11) Uani 1 1 d . . . . .
H3 H 0.6080 0.4843 0.3972 0.013 Uiso 1 1 calc R U . . .
C4 C 0.64548(4) 0.70381(11) 0.25258(4) 0.01267(12) Uani 1 1 d . . . . .
C5 C 0.61710(5) 0.48532(12) 0.22538(4) 0.01725(13) Uani 1 1 d . . . . .
H5A H 0.6365 0.4580 0.1764 0.026 Uiso 1 1 calc R U . . .
H5B H 0.5553 0.4772 0.2204 0.026 Uiso 1 1 calc R U . . .
H5C H 0.6412 0.3804 0.2619 0.026 Uiso 1 1 calc R U . . .
C6 C 0.60924(5) 0.87219(12) 0.19737(4) 0.01808(13) Uani 1 1 d . . . . .
H6A H 0.6282 1.0107 0.2163 0.027 Uiso 1 1 calc R U . . .
H6B H 0.5474 0.8662 0.1920 0.027 Uiso 1 1 calc R U . . .
H6C H 0.6288 0.8480 0.1482 0.027 Uiso 1 1 calc R U . . .
C7 C 0.79002(4) 0.56496(11) 0.34277(4) 0.01301(12) Uani 1 1 d . . . . .
C8 C 0.73860(4) 0.51566(11) 0.39509(3) 0.01207(11) Uani 1 1 d . . . . .
C9 C 0.88006(4) 0.49942(11) 0.34599(4) 0.01313(12) Uani 1 1 d . . . . .
C10 C 0.94111(5) 0.58203(13) 0.40033(4) 0.01942(14) Uani 1 1 d . . . . .
H10 H 0.9250 0.6798 0.4361 0.023 Uiso 1 1 calc R U . . .
C11 C 1.02537(5) 0.52310(14) 0.40293(5) 0.02176(15) Uani 1 1 d . . . . .
H11 H 1.0664 0.5806 0.4403 0.026 Uiso 1 1 calc R U . . .
C12 C 1.04939(5) 0.38079(14) 0.35110(5) 0.02142(15) Uani 1 1 d . . . . .
H12 H 1.1069 0.3401 0.3530 0.026 Uiso 1 1 calc R U . . .
C13 C 0.98914(5) 0.29728(13) 0.29613(5) 0.02150(15) Uani 1 1 d . . . . .
H13 H 1.0055 0.1994 0.2606 0.026 Uiso 1 1 calc R U . . .
C14 C 0.90513(5) 0.35752(12) 0.29347(4) 0.01749(13) Uani 1 1 d . . . . .
H14 H 0.8643 0.3016 0.2555 0.021 Uiso 1 1 calc R U . . .
C15 C 0.76409(4) 0.37005(11) 0.45915(4) 0.01279(12) Uani 1 1 d . . . . .
C16 C 0.73899(5) 0.41193(13) 0.53015(4) 0.01850(14) Uani 1 1 d . . . . .
H16 H 0.7067 0.5342 0.5370 0.022 Uiso 1 1 calc R U . . .
C17 C 0.76067(6) 0.27718(14) 0.59087(4) 0.02088(15) Uani 1 1 d . . . . .
H17 H 0.7431 0.3087 0.6385 0.025 Uiso 1 1 calc R U . . .
C18 C 0.80750(5) 0.09810(13) 0.58229(4) 0.02001(14) Uani 1 1 d . . . . .
H18 H 0.8229 0.0074 0.6239 0.024 Uiso 1 1 calc R U . . .
C19 C 0.83174(5) 0.05253(12) 0.51202(4) 0.02027(14) Uani 1 1 d . . . . .
H19 H 0.8635 -0.0708 0.5056 0.024 Uiso 1 1 calc R U . . .
C20 C 0.80995(5) 0.18584(11) 0.45083(4) 0.01657(13) Uani 1 1 d . . . . .
H20 H 0.8264 0.1513 0.4031 0.020 Uiso 1 1 calc R U . . .
C21 C 0.49199(5) 0.75016(13) 0.46531(5) 0.01862(14) Uani 1 1 d . . . . .
H21A H 0.4563 0.7355 0.5059 0.028 Uiso 1 1 calc R U . . .
H21B H 0.4873 0.6234 0.4340 0.028 Uiso 1 1 calc R U . . .
H21C H 0.4735 0.8722 0.4342 0.028 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 C7 1.7738(7) . ?
S1 C4 1.8450(7) . ?
O1 C1 1.2158(8) . ?
O2 C2 1.3997(8) . ?
O2 C21 1.4331(10) . ?
N1 C1 1.3757(9) . ?
N1 C4 1.4483(9) . ?
N1 C3 1.4737(8) . ?
C1 C2 1.5402(9) . ?
C2 C3 1.5806(9) . ?
C2 H2 1.0000 . ?
C3 C8 1.5105(9) . ?
C3 H3 1.0000 . ?
C4 C6 1.5233(10) . ?
C4 C5 1.5250(10) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3549(9) . ?
C7 C9 1.4907(9) . ?
C8 C15 1.4915(9) . ?
C9 C10 1.3926(10) . ?
C9 C14 1.3971(10) . ?
C10 C11 1.3912(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.3841(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.3939(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.3897(11) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.4007(10) . ?
C15 C16 1.4032(9) . ?
C16 C17 1.3944(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.3827(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.3904(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.3953(10) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
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
C7 S1 C4 100.95(3) . . ?
C2 O2 C21 114.11(6) . . ?
C1 N1 C4 133.77(6) . . ?
C1 N1 C3 96.10(5) . . ?
C4 N1 C3 123.66(5) . . ?
O1 C1 N1 132.88(6) . . ?
O1 C1 C2 135.40(6) . . ?
N1 C1 C2 91.72(5) . . ?
O2 C2 C1 120.24(6) . . ?
O2 C2 C3 119.96(5) . . ?
C1 C2 C3 85.58(5) . . ?
O2 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
N1 C3 C8 115.07(5) . . ?
N1 C3 C2 86.58(5) . . ?
C8 C3 C2 117.41(5) . . ?
N1 C3 H3 111.8 . . ?
C8 C3 H3 111.8 . . ?
C2 C3 H3 111.8 . . ?
N1 C4 C6 112.20(6) . . ?
N1 C4 C5 109.19(5) . . ?
C6 C4 C5 111.21(6) . . ?
N1 C4 S1 106.09(4) . . ?
C6 C4 S1 108.14(5) . . ?
C5 C4 S1 109.87(5) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C9 124.80(6) . . ?
C8 C7 S1 125.49(5) . . ?
C9 C7 S1 109.70(4) . . ?
C7 C8 C15 122.93(6) . . ?
C7 C8 C3 122.66(6) . . ?
C15 C8 C3 114.38(5) . . ?
C10 C9 C14 118.71(6) . . ?
C10 C9 C7 120.65(6) . . ?
C14 C9 C7 120.62(6) . . ?
C11 C10 C9 120.79(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.02(7) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.92(7) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.86(7) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 120.68(7) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C20 C15 C16 117.79(6) . . ?
C20 C15 C8 122.44(6) . . ?
C16 C15 C8 119.72(6) . . ?
C17 C16 C15 121.12(7) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 120.51(7) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.12(7) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 120.78(7) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 120.67(7) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C4 N1 C1 O1 26.87(13) . . . . ?
C3 N1 C1 O1 177.84(8) . . . . ?
C4 N1 C1 C2 -152.22(7) . . . . ?
C3 N1 C1 C2 -1.25(5) . . . . ?
C21 O2 C2 C1 38.31(8) . . . . ?
C21 O2 C2 C3 -65.17(8) . . . . ?
O1 C1 C2 O2 59.79(11) . . . . ?
N1 C1 C2 O2 -121.16(6) . . . . ?
O1 C1 C2 C3 -177.88(9) . . . . ?
N1 C1 C2 C3 1.17(5) . . . . ?
C1 N1 C3 C8 -117.54(6) . . . . ?
C4 N1 C3 C8 37.56(9) . . . . ?
C1 N1 C3 C2 1.22(5) . . . . ?
C4 N1 C3 C2 156.32(6) . . . . ?
O2 C2 C3 N1 121.48(6) . . . . ?
C1 C2 C3 N1 -1.09(5) . . . . ?
O2 C2 C3 C8 -121.96(7) . . . . ?
C1 C2 C3 C8 115.47(6) . . . . ?
C1 N1 C4 C6 -34.72(10) . . . . ?
C3 N1 C4 C6 -179.28(6) . . . . ?
C1 N1 C4 C5 -158.48(7) . . . . ?
C3 N1 C4 C5 56.96(8) . . . . ?
C1 N1 C4 S1 83.17(8) . . . . ?
C3 N1 C4 S1 -61.39(7) . . . . ?
C7 S1 C4 N1 45.62(5) . . . . ?
C7 S1 C4 C6 166.17(5) . . . . ?
C7 S1 C4 C5 -72.29(5) . . . . ?
C4 S1 C7 C8 -20.03(7) . . . . ?
C4 S1 C7 C9 161.37(5) . . . . ?
C9 C7 C8 C15 -6.32(11) . . . . ?
S1 C7 C8 C15 175.29(5) . . . . ?
C9 C7 C8 C3 175.47(6) . . . . ?
S1 C7 C8 C3 -2.92(10) . . . . ?
N1 C3 C8 C7 0.54(9) . . . . ?
C2 C3 C8 C7 -99.15(8) . . . . ?
N1 C3 C8 C15 -177.81(6) . . . . ?
C2 C3 C8 C15 82.50(7) . . . . ?
C8 C7 C9 C10 -68.89(10) . . . . ?
S1 C7 C9 C10 109.72(7) . . . . ?
C8 C7 C9 C14 112.57(8) . . . . ?
S1 C7 C9 C14 -68.82(8) . . . . ?
C14 C9 C10 C11 -0.66(12) . . . . ?
C7 C9 C10 C11 -179.22(7) . . . . ?
C9 C10 C11 C12 0.01(13) . . . . ?
C10 C11 C12 C13 0.26(13) . . . . ?
C11 C12 C13 C14 0.12(13) . . . . ?
C12 C13 C14 C9 -0.78(13) . . . . ?
C10 C9 C14 C13 1.04(12) . . . . ?
C7 C9 C14 C13 179.60(7) . . . . ?
C7 C8 C15 C20 -40.43(10) . . . . ?
C3 C8 C15 C20 137.92(7) . . . . ?
C7 C8 C15 C16 142.16(7) . . . . ?
C3 C8 C15 C16 -39.49(9) . . . . ?
C20 C15 C16 C17 1.47(11) . . . . ?
C8 C15 C16 C17 179.00(7) . . . . ?
C15 C16 C17 C18 -0.14(13) . . . . ?
C16 C17 C18 C19 -0.87(13) . . . . ?
C17 C18 C19 C20 0.52(13) . . . . ?
C18 C19 C20 C15 0.84(12) . . . . ?
C16 C15 C20 C19 -1.81(11) . . . . ?
C8 C15 C20 C19 -179.27(7) . . . . ?

_refine_diff_density_max         0.577
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 976016'
