# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1012033'

_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 F2 N2 O3 S'
_chemical_formula_weight         380.40

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7793(15)
_cell_length_b                   8.4442(15)
_cell_length_c                   23.810(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.312(6)
_cell_angle_gamma                90.00
_cell_volume                     1750.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2005
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      24.99

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_T_max  0.001
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14668
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3077
_reflns_number_gt                2684
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT--Plus (Bruker, 2001)'
_computing_data_reduction        SAINT--Plus
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0875P)²+0.7360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3077
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6694(2) 0.5645(3) 0.33594(10) 0.0447(5) Uani 1 1 d . . .
C6 C 0.5341(2) 0.5834(2) 0.35904(9) 0.0365(5) Uani 1 1 d . . .
C5 C 0.4212(3) 0.6715(3) 0.32755(10) 0.0490(6) Uani 1 1 d . . .
H3 H 0.3291 0.6899 0.3419 0.059 Uiso 1 1 calc R . .
C4 C 0.4418(3) 0.7332(3) 0.27524(11) 0.0597(7) Uani 1 1 d . . .
H4 H 0.3647 0.7921 0.2544 0.072 Uiso 1 1 calc R . .
C3 C 0.5781(3) 0.7056(3) 0.25474(11) 0.0585(7) Uani 1 1 d . . .
C2 C 0.6955(3) 0.6231(3) 0.28413(12) 0.0580(7) Uani 1 1 d . . .
H6 H 0.7883 0.6073 0.2700 0.070 Uiso 1 1 calc R . .
C13 C 0.1006(2) 0.1070(3) 0.36580(9) 0.0385(5) Uani 1 1 d . . .
C12 C 0.2177(3) 0.0895(3) 0.41033(10) 0.0432(5) Uani 1 1 d . . .
H8 H 0.2401 -0.0099 0.4261 0.052 Uiso 1 1 calc R . .
C11 C 0.3003(2) 0.2199(3) 0.43111(9) 0.0403(5) Uani 1 1 d . . .
H9 H 0.3793 0.2088 0.4608 0.048 Uiso 1 1 calc R . .
C10 C 0.2657(2) 0.3687(2) 0.40761(8) 0.0340(5) Uani 1 1 d . . .
C14 C 0.0659(2) 0.2550(3) 0.34245(9) 0.0416(5) Uani 1 1 d . . .
H11 H -0.0129 0.2661 0.3127 0.050 Uiso 1 1 calc R . .
C15 C 0.1482(2) 0.3860(3) 0.36341(10) 0.0408(5) Uani 1 1 d . . .
H12 H 0.1249 0.4855 0.3479 0.049 Uiso 1 1 calc R . .
C16 C -0.2870(3) 0.0478(3) 0.36281(14) 0.0658(8) Uani 1 1 d . . .
H13A H -0.3687 0.0261 0.3324 0.079 Uiso 1 1 calc R . .
H13B H -0.2526 0.1567 0.3616 0.079 Uiso 1 1 calc R . .
C8 C 0.3049(2) 0.6238(2) 0.45767(9) 0.0370(5) Uani 1 1 d . . .
C9 C 0.1495(3) 0.6048(3) 0.47658(11) 0.0512(6) Uani 1 1 d . . .
H15A H 0.1050 0.5065 0.4625 0.077 Uiso 1 1 calc R . .
H15B H 0.0846 0.6909 0.4621 0.077 Uiso 1 1 calc R . .
H15C H 0.1594 0.6050 0.5172 0.077 Uiso 1 1 calc R . .
C7 C 0.5160(2) 0.5089(3) 0.41508(9) 0.0401(5) Uani 1 1 d . . .
H7A H 0.5562 0.4019 0.4155 0.048 Uiso 1 1 calc R . .
H7B H 0.5774 0.5679 0.4448 0.048 Uiso 1 1 calc R . .
C18 C -0.1690(3) -0.0912(4) 0.42815(12) 0.0616(7) Uani 1 1 d . . .
H17A H -0.0888 -0.0364 0.4524 0.074 Uiso 1 1 calc R . .
H17B H -0.1762 -0.2011 0.4394 0.074 Uiso 1 1 calc R . .
C17 C -0.3228(3) -0.0043(4) 0.42063(14) 0.0686(8) Uani 1 1 d . . .
H18A H -0.4113 -0.0735 0.4195 0.082 Uiso 1 1 calc R . .
H18B H -0.3289 0.0821 0.4471 0.082 Uiso 1 1 calc R . .
N1 N -0.1609(2) -0.0694(2) 0.36736(9) 0.0457(5) Uani 1 1 d . . .
N2 N 0.35756(18) 0.5030(2) 0.42793(7) 0.0351(4) Uani 1 1 d . . .
O1 O 0.38424(18) 0.74030(19) 0.47069(7) 0.0496(4) Uani 1 1 d . . .
O2 O -0.0512(3) -0.0306(2) 0.27960(8) 0.0689(6) Uani 1 1 d . . .
O3 O 0.08117(19) -0.19746(19) 0.35635(9) 0.0595(5) Uani 1 1 d . . .
F1 F 0.5958(3) 0.7614(3) 0.20283(8) 0.0956(7) Uani 1 1 d . . .
F2 F 0.78369(17) 0.4820(2) 0.36687(8) 0.0728(5) Uani 1 1 d . . .
S2 S -0.00544(6) -0.05936(7) 0.33804(2) 0.0439(2) Uani 1 1 d . . .


_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
C1 F2 1.359(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.381(3) . ?
C6 C5 1.382(3) . ?
C6 C7 1.502(3) . ?
C5 C4 1.383(4) . ?
C5 H3 0.9300 . ?
C4 C3 1.369(4) . ?
C4 H4 0.9300 . ?
C3 F1 1.350(3) . ?
C3 C2 1.362(4) . ?
C2 H6 0.9300 . ?
C13 C14 1.386(3) . ?
C13 C12 1.388(3) . ?
C13 S2 1.766(2) . ?
C12 C11 1.376(3) . ?
C12 H8 0.9300 . ?
C11 C10 1.393(3) . ?
C11 H9 0.9300 . ?
C10 C15 1.384(3) . ?
C10 N2 1.439(3) . ?
C14 C15 1.380(3) . ?
C14 H11 0.9300 . ?
C15 H12 0.9300 . ?
C16 N1 1.479(3) . ?
C16 C17 1.516(5) . ?
C16 H13A 0.9700 . ?
C16 H13B 0.9700 . ?
C8 O1 1.223(3) . ?
C8 N2 1.356(3) . ?
C8 C9 1.499(3) . ?
C9 H15A 0.9600 . ?
C9 H15B 0.9600 . ?
C9 H15C 0.9600 . ?
C7 N2 1.463(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C18 N1 1.470(3) . ?
C18 C17 1.527(4) . ?
C18 H17A 0.9700 . ?
C18 H17B 0.9700 . ?
C17 H18A 0.9700 . ?
C17 H18B 0.9700 . ?
N1 S2 1.612(2) . ?
O2 S2 1.419(2) . ?
O3 S2 1.4296(18) . ?

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
F2 C1 C2 118.4(2) . . ?
F2 C1 C6 117.2(2) . . ?
C2 C1 C6 124.5(2) . . ?
C1 C6 C5 116.1(2) . . ?
C1 C6 C7 119.94(19) . . ?
C5 C6 C7 123.92(19) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H3 119.2 . . ?
C4 C5 H3 119.2 . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
F1 C3 C2 118.8(2) . . ?
F1 C3 C4 118.3(3) . . ?
C2 C3 C4 122.9(2) . . ?
C3 C2 C1 116.3(2) . . ?
C3 C2 H6 121.8 . . ?
C1 C2 H6 121.8 . . ?
C14 C13 C12 120.43(19) . . ?
C14 C13 S2 119.25(16) . . ?
C12 C13 S2 120.32(17) . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H8 120.2 . . ?
C13 C12 H8 120.2 . . ?
C12 C11 C10 119.96(19) . . ?
C12 C11 H9 120.0 . . ?
C10 C11 H9 120.0 . . ?
C15 C10 C11 120.28(19) . . ?
C15 C10 N2 120.25(18) . . ?
C11 C10 N2 119.41(17) . . ?
C15 C14 C13 119.97(19) . . ?
C15 C14 H11 120.0 . . ?
C13 C14 H11 120.0 . . ?
C14 C15 C10 119.72(19) . . ?
C14 C15 H12 120.1 . . ?
C10 C15 H12 120.1 . . ?
N1 C16 C17 88.8(2) . . ?
N1 C16 H13A 113.8 . . ?
C17 C16 H13A 113.8 . . ?
N1 C16 H13B 113.8 . . ?
C17 C16 H13B 113.8 . . ?
H13A C16 H13B 111.1 . . ?
O1 C8 N2 121.09(19) . . ?
O1 C8 C9 121.4(2) . . ?
N2 C8 C9 117.43(19) . . ?
C8 C9 H15A 109.5 . . ?
C8 C9 H15B 109.5 . . ?
H15A C9 H15B 109.5 . . ?
C8 C9 H15C 109.5 . . ?
H15A C9 H15C 109.5 . . ?
H15B C9 H15C 109.5 . . ?
N2 C7 C6 114.27(17) . . ?
N2 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C18 C17 88.7(2) . . ?
N1 C18 H17A 113.9 . . ?
C17 C18 H17A 113.9 . . ?
N1 C18 H17B 113.9 . . ?
C17 C18 H17B 113.9 . . ?
H17A C18 H17B 111.1 . . ?
C16 C17 C18 87.9(2) . . ?
C16 C17 H18A 114.0 . . ?
C18 C17 H18A 114.0 . . ?
C16 C17 H18B 114.0 . . ?
C18 C17 H18B 114.0 . . ?
H18A C17 H18B 111.2 . . ?
C18 N1 C16 91.5(2) . . ?
C18 N1 S2 125.64(16) . . ?
C16 N1 S2 126.87(18) . . ?
C8 N2 C10 123.67(16) . . ?
C8 N2 C7 118.69(17) . . ?
C10 N2 C7 117.64(17) . . ?
O2 S2 O3 120.79(12) . . ?
O2 S2 N1 106.48(12) . . ?
O3 S2 N1 105.75(11) . . ?
O2 S2 C13 107.50(11) . . ?
O3 S2 C13 107.47(10) . . ?
N1 S2 C13 108.35(10) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1012034'
_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
_audit_creation_date             2014-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H14 N2 O3 S'
_chemical_formula_sum            'C11 H14 N2 O3 S'
_chemical_formula_weight         254.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O4N2S1
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.9357(16)
_cell_length_b                   19.6992(7)
_cell_length_c                   7.3342(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 139.81(3)
_cell_angle_gamma                90.00
_cell_volume                     1206.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1810
_cell_measurement_theta_min      4.4730
_exptl_absorpt_coefficient_mu    2.396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2246
_diffrn_reflns_theta_full        72.34
_diffrn_reflns_theta_max         72.34
_diffrn_reflns_theta_min         4.49
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -77.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega -112.00  -69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   61.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega -115.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000    0.0000  -30.0000 129

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega   90.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  7 omega   89.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
  8 omega   96.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega  133.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
 11 omega   47.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
 12 omega   63.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   51.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 14 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega -111.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000 -120.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0749283000
_diffrn_orient_matrix_UB_12      -0.0181836000
_diffrn_orient_matrix_UB_13      0.2865459000
_diffrn_orient_matrix_UB_21      -0.0841576000
_diffrn_orient_matrix_UB_22      -0.0695537000
_diffrn_orient_matrix_UB_23      -0.1185052000
_diffrn_orient_matrix_UB_31      0.1462377000
_diffrn_orient_matrix_UB_32      -0.0307214000
_diffrn_orient_matrix_UB_33      0.0988517000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1405
_reflns_number_total             1495
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1495
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.44786(10) 0.65749(4) 0.67560(16) 0.0464(2) Uani 1 d . . .
O1 O 0.5619(4) 0.60747(16) 0.7736(7) 0.0637(9) Uani 1 d . . .
O2 O 0.4914(4) 0.70737(16) 0.8665(7) 0.0657(9) Uani 1 d . . .
O3 O -0.0911(4) 0.40595(14) 0.1436(9) 0.0754(11) Uani 1 d . . .
N1 N 0.3974(4) 0.69875(16) 0.4242(8) 0.0481(8) Uani 1 d . . .
N2 N -0.1459(4) 0.51742(17) 0.1160(7) 0.0473(8) Uani 1 d . . .
H2 H -0.204(6) 0.547(2) 0.083(10) 0.050(12) Uiso 1 d . . .
C1 C 0.3132(6) 0.6664(2) 0.1537(10) 0.0612(11) Uani 1 d . . .
H1A H 0.2480 0.6276 0.0993 0.073 Uiso 1 calc . . R
H1B H 0.3828 0.6558 0.1454 0.073 Uiso 1 calc . . R
C2 C 0.2189(7) 0.7318(3) 0.0032(11) 0.0777(15) Uani 1 d . . .
H2A H 0.1037 0.7253 -0.1543 0.093 Uiso 1 calc . . R
H2B H 0.2540 0.7593 -0.0517 0.093 Uiso 1 calc . . R
C3 C 0.2827(6) 0.7558(2) 0.2726(10) 0.0603(11) Uani 1 d . . .
H3A H 0.3330 0.8001 0.3364 0.072 Uiso 1 calc . . R
H3B H 0.2050 0.7531 0.2659 0.072 Uiso 1 calc . . R
C4 C 0.1149(5) 0.51337(18) 0.3127(8) 0.0431(8) Uani 1 d . . .
H4 H 0.1002 0.4679 0.2632 0.052 Uiso 1 calc . . R
C5 C 0.2520(4) 0.54705(18) 0.4421(8) 0.0431(8) Uani 1 d . . .
H5 H 0.3276 0.5246 0.4731 0.052 Uiso 1 calc . . R
C6 C 0.2771(4) 0.61409(17) 0.5258(8) 0.0422(8) Uani 1 d . . .
C7 C 0.1636(5) 0.64861(16) 0.4765(9) 0.0456(8) Uani 1 d . . .
H7 H 0.1807 0.6936 0.5331 0.055 Uiso 1 calc . . R
C8 C 0.0245(5) 0.61523(17) 0.3420(9) 0.0466(9) Uani 1 d . . .
H8 H -0.0519 0.6379 0.3085 0.056 Uiso 1 calc . . R
C9 C -0.0006(4) 0.54783(18) 0.2571(8) 0.0415(8) Uani 1 d . . .
C10 C -0.1834(5) 0.4497(2) 0.0646(9) 0.0516(10) Uani 1 d . . .
C11 C -0.3500(6) 0.4342(2) -0.0950(11) 0.0659(12) Uani 1 d . . .
H11A H -0.3473 0.4229 0.0359 0.099 Uiso 1 calc . . GR
H11B H -0.3923 0.3966 -0.2198 0.099 Uiso 1 calc . . GR
H11C H -0.4169 0.4733 -0.2032 0.099 Uiso 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
S1 O1 1.430(3) . ?
S1 O2 1.428(3) . ?
S1 N1 1.627(4) . ?
S1 C6 1.764(4) . ?
O3 C10 1.203(5) . ?
N1 C1 1.492(6) . ?
N1 C3 1.476(5) . ?
N2 H2 0.83(4) . ?
N2 C9 1.411(5) . ?
N2 C10 1.371(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.520(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.522(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.383(5) . ?
C4 C9 1.390(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(5) . ?
C6 C7 1.391(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(5) . ?
C10 C11 1.501(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
O1 S1 N1 106.3(2) . . ?
O1 S1 C6 107.44(17) . . ?
O2 S1 O1 119.9(2) . . ?
O2 S1 N1 106.48(18) . . ?
O2 S1 C6 108.2(2) . . ?
N1 S1 C6 108.00(18) . . ?
C1 N1 S1 123.2(3) . . ?
C3 N1 S1 122.4(3) . . ?
C3 N1 C1 91.8(3) . . ?
C9 N2 H2 108(3) . . ?
C10 N2 H2 124(3) . . ?
C10 N2 C9 127.5(3) . . ?
N1 C1 H1A 113.9 . . ?
N1 C1 H1B 113.9 . . ?
N1 C1 C2 88.2(3) . . ?
H1A C1 H1B 111.1 . . ?
C2 C1 H1A 113.9 . . ?
C2 C1 H1B 113.9 . . ?
C1 C2 H2A 113.8 . . ?
C1 C2 H2B 113.8 . . ?
C1 C2 C3 88.9(4) . . ?
H2A C2 H2B 111.0 . . ?
C3 C2 H2A 113.8 . . ?
C3 C2 H2B 113.8 . . ?
N1 C3 C2 88.8(3) . . ?
N1 C3 H3A 113.9 . . ?
N1 C3 H3B 113.9 . . ?
C2 C3 H3A 113.9 . . ?
C2 C3 H3B 113.9 . . ?
H3A C3 H3B 111.1 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C9 119.6(3) . . ?
C9 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 S1 119.7(3) . . ?
C5 C6 C7 120.4(3) . . ?
C7 C6 S1 119.7(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 N2 122.7(3) . . ?
C4 C9 C8 120.1(3) . . ?
C8 C9 N2 117.2(3) . . ?
O3 C10 N2 123.5(4) . . ?
O3 C10 C11 122.5(4) . . ?
N2 C10 C11 114.0(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N2 H2 O1 0.83(4) 2.29(5) 3.039(4) 151(4) 1_454

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 C1 C2 142.9(4) . . . . ?
S1 N1 C3 C2 -143.5(4) . . . . ?
S1 C6 C7 C8 175.9(3) . . . . ?
O1 S1 N1 C1 63.8(4) . . . . ?
O1 S1 N1 C3 -178.9(3) . . . . ?
O1 S1 C6 C5 -19.8(4) . . . . ?
O1 S1 C6 C7 164.2(3) . . . . ?
O2 S1 N1 C1 -167.2(3) . . . . ?
O2 S1 N1 C3 -50.0(4) . . . . ?
O2 S1 C6 C5 -150.6(3) . . . . ?
O2 S1 C6 C7 33.4(4) . . . . ?
N1 S1 C6 C5 94.5(3) . . . . ?
N1 S1 C6 C7 -81.5(3) . . . . ?
N1 C1 C2 C3 -11.2(4) . . . . ?
C1 N1 C3 C2 -11.6(4) . . . . ?
C1 C2 C3 N1 11.4(4) . . . . ?
C3 N1 C1 C2 11.6(4) . . . . ?
C4 C5 C6 S1 -177.1(3) . . . . ?
C4 C5 C6 C7 -1.1(6) . . . . ?
C5 C4 C9 N2 177.5(3) . . . . ?
C5 C4 C9 C8 -2.6(6) . . . . ?
C5 C6 C7 C8 -0.1(6) . . . . ?
C6 S1 N1 C1 -51.2(4) . . . . ?
C6 S1 N1 C3 66.0(4) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
C7 C8 C9 N2 -178.6(3) . . . . ?
C7 C8 C9 C4 1.5(6) . . . . ?
C9 N2 C10 O3 2.0(7) . . . . ?
C9 N2 C10 C11 -179.2(4) . . . . ?
C9 C4 C5 C6 2.4(6) . . . . ?
C10 N2 C9 C4 14.2(6) . . . . ?
C10 N2 C9 C8 -165.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
