# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_0230b-1
_database_code_depnum_ccdc_archive 'CCDC 1051440'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            
'6-methyl-8-(4-methylphenylsulfonamido)quinoline N-oxide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 O3 S'
_chemical_formula_sum            'C17 H16 N2 O3 S'
_chemical_formula_weight         328.38

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   C2/c

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

_cell_length_a                   26.8782(11)
_cell_length_b                   8.2244(3)
_cell_length_c                   19.4674(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 132.6436(12)
_cell_angle_gamma                90.00
_cell_volume                     3165.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    33667
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9227
_exptl_absorpt_correction_T_max  0.9448
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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_reflns_number            33667
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3921
_reflns_number_gt                3574
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0575P)²+2.5092P] 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         3921
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
S1 S 0.204703(14) 0.87105(4) 0.12314(2) 0.02354(10) Uani 1 1 d . . .
C11 C 0.19333(6) 0.69173(15) 0.06472(8) 0.0221(2) Uani 1 1 d . . .
C14 C 0.17335(6) 0.41013(16) -0.03043(10) 0.0273(3) Uani 1 1 d . . .
C15 C 0.19601(7) 0.40164(16) 0.05838(10) 0.0289(3) Uani 1 1 d . . .
H15A H 0.2050 0.2986 0.0869 0.035 Uiso 1 1 calc R . .
C16 C 0.20564(6) 0.54227(16) 0.10601(9) 0.0261(3) Uani 1 1 d . . .
H16A H 0.2205 0.5354 0.1662 0.031 Uiso 1 1 calc R . .
C13 C 0.16100(8) 0.56249(18) -0.07062(10) 0.0345(3) Uani 1 1 d . . .
H13A H 0.1455 0.5696 -0.1312 0.041 Uiso 1 1 calc R . .
C17 C 0.16149(8) 0.25809(18) -0.08325(11) 0.0374(3) Uani 1 1 d . . .
H17A H 0.1131 0.2322 -0.1287 0.056 Uiso 1 1 calc R . .
H17B H 0.1867 0.1675 -0.0393 0.056 Uiso 1 1 calc R . .
H17C H 0.1769 0.2758 -0.1160 0.056 Uiso 1 1 calc R . .
C12 C 0.17090(8) 0.70386(17) -0.02406(10) 0.0333(3) Uani 1 1 d . . .
H12A H 0.1626 0.8071 -0.0520 0.040 Uiso 1 1 calc R . .
O2 O 0.24304(5) 0.98553(12) 0.11920(7) 0.0335(2) Uani 1 1 d . . .
O3 O 0.22845(5) 0.82598(14) 0.21224(6) 0.0331(2) Uani 1 1 d . . .
N2 N 0.12938(5) 0.95283(13) 0.05906(7) 0.0232(2) Uani 1 1 d . . .
O1 O 0.05316(5) 1.01677(13) -0.11579(6) 0.0303(2) Uani 1 1 d . . .
N1 N 0.00261(5) 0.93850(14) -0.13303(7) 0.0239(2) Uani 1 1 d . . .
C9 C 0.01108(6) 0.86243(14) -0.06144(8) 0.0217(2) Uani 1 1 d . . .
C8 C 0.07378(6) 0.86371(14) 0.03386(8) 0.0214(2) Uani 1 1 d . . .
C7 C 0.07770(7) 0.78397(16) 0.09982(9) 0.0267(3) Uani 1 1 d . . .
H7A H 0.1193 0.7852 0.1632 0.032 Uiso 1 1 calc R . .
C1 C -0.05709(7) 0.93601(19) -0.22142(9) 0.0321(3) Uani 1 1 d . . .
H1A H -0.0610 0.9862 -0.2689 0.039 Uiso 1 1 calc R . .
C6 C 0.02195(7) 0.70076(16) 0.07626(10) 0.0303(3) Uani 1 1 d . . .
C2 C -0.11362(7) 0.8613(2) -0.24528(10) 0.0379(3) Uani 1 1 d . . .
H2A H -0.1557 0.8634 -0.3082 0.046 Uiso 1 1 calc R . .
C4 C -0.04553(6) 0.78209(16) -0.08509(9) 0.0270(3) Uani 1 1 d . . .
C5 C -0.03842(7) 0.70170(17) -0.01474(10) 0.0314(3) Uani 1 1 d . . .
H5A H -0.0763 0.6471 -0.0309 0.038 Uiso 1 1 calc R . .
C3 C -0.10865(7) 0.7855(2) -0.17875(10) 0.0354(3) Uani 1 1 d . . .
H3A H -0.1472 0.7352 -0.1949 0.042 Uiso 1 1 calc R . .
C10 C 0.02864(10) 0.6185(2) 0.15130(13) 0.0435(4) Uani 1 1 d . . .
H10A H 0.0234 0.6992 0.1830 0.065 Uiso 1 1 calc R . .
H10B H 0.0733 0.5677 0.1967 0.065 Uiso 1 1 calc R . .
H10C H -0.0064 0.5350 0.1231 0.065 Uiso 1 1 calc R . .
H1 H 0.1174(11) 0.994(3) 0.0076(15) 0.052 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 O3 1.4330(10) . ?
S1 O2 1.4357(11) . ?
S1 N2 1.6388(10) . ?
S1 C11 1.7581(12) . ?
C11 C16 1.3806(18) . ?
C11 C12 1.3958(17) . ?
C14 C15 1.3922(19) . ?
C14 C13 1.393(2) . ?
C14 C17 1.5094(18) . ?
C15 C16 1.3926(18) . ?
C13 C12 1.3847(19) . ?
N2 C8 1.4205(15) . ?
O1 N1 1.3247(14) . ?
N1 C1 1.3398(16) . ?
N1 C9 1.3986(16) . ?
C9 C4 1.4193(17) . ?
C9 C8 1.4304(16) . ?
C8 C7 1.3809(17) . ?
C7 C6 1.4116(19) . ?
C1 C2 1.395(2) . ?
C6 C5 1.370(2) . ?
C6 C10 1.506(2) . ?
C2 C3 1.360(2) . ?
C4 C5 1.4124(19) . ?
C4 C3 1.4186(19) . ?

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
O3 S1 O2 119.15(6) . . ?
O3 S1 N2 109.58(6) . . ?
O2 S1 N2 104.56(6) . . ?
O3 S1 C11 107.81(6) . . ?
O2 S1 C11 109.39(6) . . ?
N2 S1 C11 105.55(5) . . ?
C16 C11 C12 121.10(12) . . ?
C16 C11 S1 120.14(9) . . ?
C12 C11 S1 118.75(10) . . ?
C15 C14 C13 118.68(12) . . ?
C15 C14 C17 121.15(13) . . ?
C13 C14 C17 120.17(13) . . ?
C14 C15 C16 120.85(12) . . ?
C11 C16 C15 119.26(12) . . ?
C12 C13 C14 121.38(12) . . ?
C13 C12 C11 118.73(12) . . ?
C8 N2 S1 121.28(9) . . ?
O1 N1 C1 117.61(11) . . ?
O1 N1 C9 121.22(10) . . ?
C1 N1 C9 121.17(11) . . ?
N1 C9 C4 118.04(11) . . ?
N1 C9 C8 122.85(11) . . ?
C4 C9 C8 119.10(11) . . ?
C7 C8 N2 121.62(11) . . ?
C7 C8 C9 118.90(11) . . ?
N2 C8 C9 119.42(11) . . ?
C8 C7 C6 122.18(12) . . ?
N1 C1 C2 121.42(13) . . ?
C5 C6 C7 118.95(12) . . ?
C5 C6 C10 121.02(14) . . ?
C7 C6 C10 119.98(14) . . ?
C3 C2 C1 120.17(13) . . ?
C5 C4 C3 120.94(12) . . ?
C5 C4 C9 119.49(12) . . ?
C3 C4 C9 119.56(12) . . ?
C6 C5 C4 121.35(12) . . ?
C2 C3 C4 119.58(13) . . ?

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
O3 S1 C11 C16 1.51(12) . . . . ?
O2 S1 C11 C16 132.46(10) . . . . ?
N2 S1 C11 C16 -115.54(10) . . . . ?
O3 S1 C11 C12 -179.35(11) . . . . ?
O2 S1 C11 C12 -48.40(12) . . . . ?
N2 S1 C11 C12 63.60(12) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C17 C14 C15 C16 -178.79(12) . . . . ?
C12 C11 C16 C15 0.56(19) . . . . ?
S1 C11 C16 C15 179.68(10) . . . . ?
C14 C15 C16 C11 -0.87(19) . . . . ?
C15 C14 C13 C12 0.1(2) . . . . ?
C17 C14 C13 C12 179.44(14) . . . . ?
C14 C13 C12 C11 -0.4(2) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
S1 C11 C12 C13 -179.06(12) . . . . ?
O3 S1 N2 C8 -61.21(11) . . . . ?
O2 S1 N2 C8 170.00(9) . . . . ?
C11 S1 N2 C8 54.63(11) . . . . ?
O1 N1 C9 C4 179.46(11) . . . . ?
C1 N1 C9 C4 0.04(17) . . . . ?
O1 N1 C9 C8 0.04(17) . . . . ?
C1 N1 C9 C8 -179.38(12) . . . . ?
S1 N2 C8 C7 51.64(15) . . . . ?
S1 N2 C8 C9 -131.35(10) . . . . ?
N1 C9 C8 C7 -179.37(11) . . . . ?
C4 C9 C8 C7 1.21(17) . . . . ?
N1 C9 C8 N2 3.53(17) . . . . ?
C4 C9 C8 N2 -175.89(10) . . . . ?
N2 C8 C7 C6 177.27(11) . . . . ?
C9 C8 C7 C6 0.24(18) . . . . ?
O1 N1 C1 C2 -177.74(13) . . . . ?
C9 N1 C1 C2 1.7(2) . . . . ?
C8 C7 C6 C5 -1.28(19) . . . . ?
C8 C7 C6 C10 -178.85(12) . . . . ?
N1 C1 C2 C3 -1.5(2) . . . . ?
N1 C9 C4 C5 178.94(11) . . . . ?
C8 C9 C4 C5 -1.62(17) . . . . ?
N1 C9 C4 C3 -1.91(18) . . . . ?
C8 C9 C4 C3 177.53(11) . . . . ?
C7 C6 C5 C4 0.9(2) . . . . ?
C10 C6 C5 C4 178.39(13) . . . . ?
C3 C4 C5 C6 -178.56(13) . . . . ?
C9 C4 C5 C6 0.59(19) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C5 C4 C3 C2 -178.78(14) . . . . ?
C9 C4 C3 C2 2.1(2) . . . . ?

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 H1 O1 0.89(2) 1.78(2) 2.5712(14) 148(2) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.056
