# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1487716'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(E)-6-methyl-N-(1-phenylethylidene)pyridine-2-sulfonamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N2 O2 S'
_chemical_formula_sum            'C14 H14 N2 O2 S'
_chemical_formula_weight         274.33

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.121(5)
_cell_length_b                   8.835(7)
_cell_length_c                   13.265(12)
_cell_angle_alpha                83.14(2)
_cell_angle_beta                 79.60(2)
_cell_angle_gamma                72.93(2)
_cell_volume                     672.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2335
_cell_measurement_theta_min      1.56
_cell_measurement_theta_max      25.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_T_max  0.9610
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4111
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.16
_reflns_number_total             2335
_reflns_number_gt                1533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1435P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2335
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.2162
_refine_ls_wR_factor_gt          0.1851
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22057(18) 0.25564(12) 0.80139(8) 0.0547(4) Uani 1 1 d . . .
O1 O 0.3358(6) 0.3774(4) 0.7834(3) 0.0813(11) Uani 1 1 d . . .
O2 O 0.0189(5) 0.2750(4) 0.8766(2) 0.0663(9) Uani 1 1 d . . .
N1 N 0.1733(6) 0.2141(4) 0.6919(2) 0.0506(8) Uani 1 1 d . . .
N2 N 0.3477(5) -0.0524(4) 0.8464(2) 0.0491(8) Uani 1 1 d . . .
C1 C 0.0127(7) 0.3076(4) 0.6450(3) 0.0470(9) Uani 1 1 d . . .
C2 C -0.0122(7) 0.2600(4) 0.5461(3) 0.0490(9) Uani 1 1 d . . .
C3 C -0.2200(9) 0.3115(6) 0.5068(4) 0.0662(13) Uani 1 1 d . . .
H3 H -0.330(8) 0.352(5) 0.546(4) 0.060(14) Uiso 1 1 d . . .
C4 C -0.2387(10) 0.2603(7) 0.4164(4) 0.0743(14) Uani 1 1 d . . .
H4 H -0.380(9) 0.298(6) 0.392(4) 0.074(14) Uiso 1 1 d . . .
C5 C -0.0561(10) 0.1618(6) 0.3617(4) 0.0699(14) Uani 1 1 d . . .
H5 H -0.061(7) 0.120(5) 0.304(3) 0.057(12) Uiso 1 1 d . . .
C6 C 0.1534(9) 0.1128(6) 0.3981(3) 0.0634(12) Uani 1 1 d . . .
H6 H 0.294(8) 0.041(5) 0.361(3) 0.066(13) Uiso 1 1 d . . .
C7 C 0.1746(8) 0.1585(5) 0.4903(3) 0.0542(10) Uani 1 1 d . . .
H7 H 0.323(8) 0.123(5) 0.513(3) 0.057(12) Uiso 1 1 d . . .
C8 C -0.1474(10) 0.4578(5) 0.6835(4) 0.0633(12) Uani 1 1 d . . .
H8C H -0.070(11) 0.493(7) 0.731(5) 0.11(2) Uiso 1 1 d . . .
H8B H -0.280(12) 0.435(8) 0.717(5) 0.13(2) Uiso 1 1 d . . .
H8A H -0.170(8) 0.527(6) 0.628(4) 0.075(15) Uiso 1 1 d . . .
C9 C 0.4232(7) 0.0769(5) 0.8367(3) 0.0483(9) Uani 1 1 d . . .
C10 C 0.6315(8) 0.0812(7) 0.8589(3) 0.0617(12) Uani 1 1 d . . .
H10 H 0.671(8) 0.171(5) 0.857(3) 0.063(13) Uiso 1 1 d . . .
C11 C 0.7734(9) -0.0590(8) 0.8930(4) 0.0753(15) Uani 1 1 d . . .
H11 H 0.906(8) -0.064(5) 0.914(3) 0.066(13) Uiso 1 1 d . . .
C12 C 0.7029(8) -0.1950(7) 0.9036(3) 0.0671(13) Uani 1 1 d . . .
H12 H 0.807(11) -0.294(8) 0.923(5) 0.11(2) Uiso 1 1 d . . .
C13 C 0.4870(7) -0.1881(5) 0.8802(3) 0.0538(10) Uani 1 1 d . . .
C14 C 0.3949(11) -0.3285(6) 0.8928(5) 0.0741(14) Uani 1 1 d . . .
H14C H 0.278(9) -0.331(6) 0.958(4) 0.084(15) Uiso 1 1 d . . .
H14B H 0.347(13) -0.343(8) 0.821(6) 0.14(3) Uiso 1 1 d . . .
H14A H 0.516(11) -0.422(7) 0.903(4) 0.103(19) Uiso 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
S1 O2 1.421(3) . ?
S1 O1 1.427(3) . ?
S1 N1 1.633(4) . ?
S1 C9 1.771(5) . ?
N1 C1 1.287(5) . ?
N2 C13 1.332(5) . ?
N2 C9 1.337(5) . ?
C1 C2 1.471(6) . ?
C1 C8 1.483(6) . ?
C2 C7 1.383(6) . ?
C2 C3 1.392(6) . ?
C3 C4 1.365(7) . ?
C3 H3 0.79(5) . ?
C4 C5 1.349(7) . ?
C4 H4 0.93(5) . ?
C5 C6 1.383(7) . ?
C5 H5 0.90(4) . ?
C6 C7 1.371(6) . ?
C6 H6 1.00(5) . ?
C7 H7 0.96(4) . ?
C8 H8C 0.98(7) . ?
C8 H8B 0.92(7) . ?
C8 H8A 0.91(5) . ?
C9 C10 1.371(6) . ?
C10 C11 1.367(8) . ?
C10 H10 0.89(4) . ?
C11 C12 1.376(7) . ?
C11 H11 0.89(5) . ?
C12 C13 1.394(6) . ?
C12 H12 0.96(6) . ?
C13 C14 1.487(6) . ?
C14 H14C 1.02(5) . ?
C14 H14B 1.08(8) . ?
C14 H14A 0.95(6) . ?

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 O1 118.7(2) . . ?
O2 S1 N1 111.17(18) . . ?
O1 S1 N1 109.26(19) . . ?
O2 S1 C9 107.53(19) . . ?
O1 S1 C9 107.5(2) . . ?
N1 S1 C9 101.08(17) . . ?
C1 N1 S1 121.4(3) . . ?
C13 N2 C9 117.2(3) . . ?
N1 C1 C2 116.9(3) . . ?
N1 C1 C8 124.9(4) . . ?
C2 C1 C8 118.2(4) . . ?
C7 C2 C3 118.2(4) . . ?
C7 C2 C1 119.5(4) . . ?
C3 C2 C1 122.3(4) . . ?
C4 C3 C2 120.6(5) . . ?
C4 C3 H3 122(3) . . ?
C2 C3 H3 115(4) . . ?
C5 C4 C3 121.1(5) . . ?
C5 C4 H4 121(3) . . ?
C3 C4 H4 118(3) . . ?
C4 C5 C6 119.1(5) . . ?
C4 C5 H5 125(3) . . ?
C6 C5 H5 116(3) . . ?
C7 C6 C5 120.8(5) . . ?
C7 C6 H6 116(3) . . ?
C5 C6 H6 123(2) . . ?
C6 C7 C2 120.0(5) . . ?
C6 C7 H7 119(2) . . ?
C2 C7 H7 121(2) . . ?
C1 C8 H8C 107(4) . . ?
C1 C8 H8B 107(4) . . ?
H8C C8 H8B 111(5) . . ?
C1 C8 H8A 106(3) . . ?
H8C C8 H8A 111(5) . . ?
H8B C8 H8A 114(5) . . ?
N2 C9 C10 125.4(4) . . ?
N2 C9 S1 114.8(3) . . ?
C10 C9 S1 119.7(4) . . ?
C11 C10 C9 116.9(5) . . ?
C11 C10 H10 120(3) . . ?
C9 C10 H10 123(3) . . ?
C10 C11 C12 119.6(5) . . ?
C10 C11 H11 122(3) . . ?
C12 C11 H11 118(3) . . ?
C11 C12 C13 119.6(5) . . ?
C11 C12 H12 119(4) . . ?
C13 C12 H12 121(4) . . ?
N2 C13 C12 121.3(4) . . ?
N2 C13 C14 115.7(4) . . ?
C12 C13 C14 123.0(5) . . ?
C13 C14 H14C 113(3) . . ?
C13 C14 H14B 109(4) . . ?
H14C C14 H14B 118(5) . . ?
C13 C14 H14A 109(4) . . ?
H14C C14 H14A 103(4) . . ?
H14B C14 H14A 103(5) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        25.16
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.076
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'dichloromethane, iso-propanol'
_chemical_compound_source        synthesis
_chemical_properties_physical    ', Moisture-sensitive'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1487720'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(R)-6-methyl-N-(1-nitro-2-phenylpropan-2-yl)pyridine-2-sulfonamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N3 O4 S'
_chemical_formula_weight         335.38
_chemical_absolute_configuration AD

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.6132(15)
_cell_length_b                   7.4744(14)
_cell_length_c                   12.867(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.429(5)
_cell_angle_gamma                90.00
_cell_volume                     781.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2200
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.12

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5194
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.30
_reflns_number_total             2777
_reflns_number_gt                2581
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0499P)²+0.0523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_number_reflns         2777
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0316(3) 0.2617(6) 0.5061(3) 0.0672(11) Uani 1 1 d . . .
H1A H 1.0049 0.3220 0.5638 0.101 Uiso 1 1 calc R . .
H1B H 1.0984 0.3383 0.4785 0.101 Uiso 1 1 calc R . .
H1C H 1.0912 0.1539 0.5347 0.101 Uiso 1 1 calc R . .
C2 C 0.8766(3) 0.2160(4) 0.4148(2) 0.0392(6) Uani 1 1 d . . .
C3 C 0.8802(3) 0.1439(4) 0.3166(2) 0.0395(6) Uani 1 1 d . . .
H3 H 0.9802 0.1300 0.3045 0.047 Uiso 1 1 calc R . .
C4 C 0.7369(3) 0.0930(4) 0.2372(2) 0.0417(7) Uani 1 1 d . . .
H4 H 0.7386 0.0439 0.1712 0.050 Uiso 1 1 calc R . .
C5 C 0.5901(3) 0.1155(4) 0.2565(2) 0.0357(6) Uani 1 1 d . . .
H5 H 0.4905 0.0797 0.2054 0.043 Uiso 1 1 calc R . .
C6 C 0.5975(3) 0.1930(3) 0.35452(19) 0.0283(5) Uani 1 1 d . . .
C7 C 0.5237(3) 0.4434(4) 0.0394(2) 0.0384(6) Uani 1 1 d . . .
H7 H 0.5074 0.3892 -0.0285 0.046 Uiso 1 1 calc R . .
C8 C 0.6717(3) 0.5218(4) 0.0942(2) 0.0394(6) Uani 1 1 d . . .
H8 H 0.7556 0.5217 0.0636 0.047 Uiso 1 1 calc R . .
C9 C 0.6957(3) 0.6010(4) 0.1950(2) 0.0395(6) Uani 1 1 d . . .
H9 H 0.7959 0.6551 0.2326 0.047 Uiso 1 1 calc R . .
C10 C 0.5716(3) 0.6001(3) 0.24040(19) 0.0318(5) Uani 1 1 d . . .
H10 H 0.5893 0.6528 0.3089 0.038 Uiso 1 1 calc R . .
C11 C 0.4205(2) 0.5217(3) 0.18516(18) 0.0241(5) Uani 1 1 d . . .
C12 C 0.3978(3) 0.4438(4) 0.08385(19) 0.0327(6) Uani 1 1 d . . .
H12 H 0.2972 0.3913 0.0452 0.039 Uiso 1 1 calc R . .
C13 C 0.2873(3) 0.5188(3) 0.24059(18) 0.0254(5) Uani 1 1 d . . .
C14 C 0.1302(3) 0.4219(4) 0.1724(2) 0.0362(6) Uani 1 1 d . . .
H14A H 0.1571 0.3030 0.1559 0.054 Uiso 1 1 calc R . .
H14B H 0.0792 0.4861 0.1050 0.054 Uiso 1 1 calc R . .
H14C H 0.0556 0.4158 0.2136 0.054 Uiso 1 1 calc R . .
C15 C 0.2435(3) 0.7098(3) 0.26739(19) 0.0314(6) Uani 1 1 d . . .
H15A H 0.1786 0.7024 0.3160 0.038 Uiso 1 1 calc R . .
H15B H 0.3441 0.7739 0.3060 0.038 Uiso 1 1 calc R . .
N1 N 0.7345(2) 0.2431(4) 0.43392(15) 0.0347(4) Uani 1 1 d . . .
N2 N 0.3535(2) 0.4393(3) 0.35362(15) 0.0268(4) Uani 1 1 d . . .
H2 H 0.3616 0.5098 0.4080 0.032 Uiso 1 1 calc R . .
N3 N 0.1496(3) 0.8114(3) 0.16674(19) 0.0386(5) Uani 1 1 d . . .
O1 O 0.44980(18) 0.2246(3) 0.50096(13) 0.0399(4) Uani 1 1 d . . .
O2 O 0.2900(2) 0.1182(2) 0.31421(15) 0.0396(4) Uani 1 1 d . . .
O3 O 0.0055(2) 0.8400(4) 0.1511(2) 0.0695(7) Uani 1 1 d . . .
O4 O 0.2229(3) 0.8613(3) 0.10723(17) 0.0612(6) Uani 1 1 d . . .
S1 S 0.41150(6) 0.23440(7) 0.38395(4) 0.02731(15) 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 C2 1.496(4) . ?
C2 N1 1.341(3) . ?
C2 C3 1.384(4) . ?
C3 C4 1.369(4) . ?
C4 C5 1.378(4) . ?
C5 C6 1.370(3) . ?
C6 N1 1.332(3) . ?
C6 S1 1.792(2) . ?
C7 C8 1.366(4) . ?
C7 C12 1.384(3) . ?
C8 C9 1.378(4) . ?
C9 C10 1.378(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.381(3) . ?
C11 C13 1.540(3) . ?
C13 N2 1.497(3) . ?
C13 C14 1.528(3) . ?
C13 C15 1.545(3) . ?
C15 N3 1.487(3) . ?
N2 S1 1.618(2) . ?
N3 O4 1.202(3) . ?
N3 O3 1.209(3) . ?
O1 S1 1.4320(17) . ?
O2 S1 1.4250(17) . ?

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
N1 C2 C3 121.7(2) . . ?
N1 C2 C1 116.9(2) . . ?
C3 C2 C1 121.4(2) . . ?
C4 C3 C2 120.1(2) . . ?
C3 C4 C5 119.1(3) . . ?
C6 C5 C4 116.9(2) . . ?
N1 C6 C5 125.7(2) . . ?
N1 C6 S1 114.56(17) . . ?
C5 C6 S1 119.75(17) . . ?
C8 C7 C12 120.7(2) . . ?
C7 C8 C9 119.4(2) . . ?
C10 C9 C8 120.2(2) . . ?
C9 C10 C11 120.8(2) . . ?
C12 C11 C10 118.4(2) . . ?
C12 C11 C13 122.56(19) . . ?
C10 C11 C13 119.00(19) . . ?
C11 C12 C7 120.4(2) . . ?
N2 C13 C14 110.36(18) . . ?
N2 C13 C11 110.71(17) . . ?
C14 C13 C11 113.26(18) . . ?
N2 C13 C15 101.09(18) . . ?
C14 C13 C15 109.31(19) . . ?
C11 C13 C15 111.43(18) . . ?
N3 C15 C13 112.33(19) . . ?
C6 N1 C2 116.5(2) . . ?
C13 N2 S1 126.68(16) . . ?
O4 N3 O3 124.5(2) . . ?
O4 N3 C15 117.7(2) . . ?
O3 N3 C15 117.8(2) . . ?
O2 S1 O1 119.67(11) . . ?
O2 S1 N2 108.80(10) . . ?
O1 S1 N2 104.28(11) . . ?
O2 S1 C6 106.42(11) . . ?
O1 S1 C6 107.69(10) . . ?
N2 S1 C6 109.78(10) . . ?

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
N1 C2 C3 C4 -2.1(4) . . . . ?
C1 C2 C3 C4 175.9(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 1.7(4) . . . . ?
C4 C5 C6 N1 -2.3(4) . . . . ?
C4 C5 C6 S1 177.8(2) . . . . ?
C12 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C9 C10 C11 C13 178.1(2) . . . . ?
C10 C11 C12 C7 0.5(4) . . . . ?
C13 C11 C12 C7 -177.3(2) . . . . ?
C8 C7 C12 C11 -0.8(4) . . . . ?
C12 C11 C13 N2 124.6(2) . . . . ?
C10 C11 C13 N2 -53.1(3) . . . . ?
C12 C11 C13 C14 0.0(3) . . . . ?
C10 C11 C13 C14 -177.7(2) . . . . ?
C12 C11 C13 C15 -123.7(2) . . . . ?
C10 C11 C13 C15 58.5(3) . . . . ?
N2 C13 C15 N3 -171.07(18) . . . . ?
C14 C13 C15 N3 -54.7(2) . . . . ?
C11 C13 C15 N3 71.3(2) . . . . ?
C5 C6 N1 C2 0.6(4) . . . . ?
S1 C6 N1 C2 -179.4(2) . . . . ?
C3 C2 N1 C6 1.6(4) . . . . ?
C1 C2 N1 C6 -176.4(3) . . . . ?
C14 C13 N2 S1 60.1(2) . . . . ?
C11 C13 N2 S1 -66.1(2) . . . . ?
C15 C13 N2 S1 175.72(15) . . . . ?
C13 C15 N3 O4 -72.2(3) . . . . ?
C13 C15 N3 O3 108.7(3) . . . . ?
C13 N2 S1 O2 -46.3(2) . . . . ?
C13 N2 S1 O1 -175.03(17) . . . . ?
C13 N2 S1 C6 69.83(19) . . . . ?
N1 C6 S1 O2 -159.02(19) . . . . ?
C5 C6 S1 O2 21.0(2) . . . . ?
N1 C6 S1 O1 -29.5(2) . . . . ?
C5 C6 S1 O1 150.4(2) . . . . ?
N1 C6 S1 N2 83.4(2) . . . . ?
C5 C6 S1 N2 -96.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.039
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'dichloromethane, isopropanol'
_chemical_compound_source        synthesis
