# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_20161124
_database_code_depnum_ccdc_archive 'CCDC 1534620'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Methyl 4-hydroxy-7-methoxy-2-(methylthio)quinoline-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 N O4 S'
_chemical_formula_weight         279.30

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)/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                   9.10090(10)
_cell_length_b                   17.5658(2)
_cell_length_c                   8.18620(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.2940(10)
_cell_angle_gamma                90.00
_cell_volume                     1273.61(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    5040
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.27

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9299
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3202
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         28.44
_reflns_number_total             3202
_reflns_number_gt                2545
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0748P)²+0.1717P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 -0.02015(5) 0.60966(3) 0.22315(7) 0.04765(18) Uani 1 1 d . . .
O1 O 0.39833(15) 0.94818(7) 0.62089(17) 0.0503(4) Uani 1 1 d . . .
O2 O 0.47092(15) 0.59323(7) 0.69594(16) 0.0467(3) Uani 1 1 d . . .
H2 H 0.4609 0.5477 0.6743 0.070 Uiso 1 1 calc R . .
O3 O 0.33726(17) 0.47459(7) 0.56158(19) 0.0578(4) Uani 1 1 d . . .
O4 O 0.13296(17) 0.48363(7) 0.35454(19) 0.0570(4) Uani 1 1 d . . .
N1 N 0.14465(16) 0.72159(8) 0.37744(19) 0.0390(3) Uani 1 1 d . . .
C1 C 0.13705(19) 0.64734(10) 0.3710(2) 0.0369(4) Uani 1 1 d . . .
C2 C 0.26287(18) 0.75499(9) 0.4903(2) 0.0344(4) Uani 1 1 d . . .
C3 C 0.26927(19) 0.83499(10) 0.4936(2) 0.0388(4) Uani 1 1 d . . .
H3A H 0.1965 0.8633 0.4202 0.047 Uiso 1 1 calc R . .
C4 C 0.3833(2) 0.87111(10) 0.6056(2) 0.0382(4) Uani 1 1 d . . .
C5 C 0.4955(2) 0.82884(10) 0.7167(2) 0.0442(4) Uani 1 1 d . . .
H5A H 0.5724 0.8539 0.7920 0.053 Uiso 1 1 calc R . .
C6 C 0.49082(19) 0.75154(10) 0.7135(2) 0.0410(4) Uani 1 1 d . . .
H6A H 0.5652 0.7239 0.7865 0.049 Uiso 1 1 calc R . .
C7 C 0.37439(18) 0.71259(9) 0.6006(2) 0.0344(4) Uani 1 1 d . . .
C8 C 0.36370(19) 0.63216(10) 0.5911(2) 0.0360(4) Uani 1 1 d . . .
C9 C 0.24457(19) 0.59738(10) 0.4755(2) 0.0369(4) Uani 1 1 d . . .
C10 C 0.2437(2) 0.51416(10) 0.4697(2) 0.0411(4) Uani 1 1 d . . .
C11 C 0.1318(3) 0.40149(11) 0.3424(3) 0.0642(6) Uani 1 1 d . . .
H11A H 0.0474 0.3856 0.2556 0.096 Uiso 1 1 calc R . .
H11B H 0.1234 0.3799 0.4476 0.096 Uiso 1 1 calc R . .
H11C H 0.2238 0.3845 0.3159 0.096 Uiso 1 1 calc R . .
C12 C -0.1103(3) 0.69582(13) 0.1328(3) 0.0588(6) Uani 1 1 d . . .
H12A H -0.198(3) 0.6821(16) 0.057(4) 0.088 Uiso 1 1 d . . .
H12B H -0.040(3) 0.7246(16) 0.082(3) 0.088 Uiso 1 1 d . . .
H12C H -0.132(3) 0.7270(17) 0.228(4) 0.088 Uiso 1 1 d . . .
C13 C 0.2904(2) 0.99431(11) 0.5097(3) 0.0508(5) Uani 1 1 d . . .
H13A H 0.3133 1.0471 0.5335 0.076 Uiso 1 1 calc R . .
H13B H 0.1911 0.9834 0.5251 0.076 Uiso 1 1 calc R . .
H13C H 0.2942 0.9835 0.3958 0.076 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 C1 1.7759(17) . ?
S1 C12 1.798(2) . ?
O1 C4 1.363(2) . ?
O1 C13 1.428(2) . ?
O2 C8 1.331(2) . ?
O2 H2 0.8200 . ?
O3 C10 1.216(2) . ?
O4 C10 1.325(2) . ?
O4 C11 1.446(2) . ?
N1 C1 1.306(2) . ?
N1 C2 1.378(2) . ?
C1 C9 1.440(2) . ?
C2 C7 1.406(2) . ?
C2 C3 1.407(2) . ?
C3 C4 1.372(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.412(2) . ?
C5 C6 1.359(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.412(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.417(2) . ?
C8 C9 1.405(2) . ?
C9 C10 1.462(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.92(3) . ?
C12 H12B 0.98(3) . ?
C12 H12C 1.00(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C1 S1 C12 100.75(9) . . ?
C4 O1 C13 117.73(14) . . ?
C8 O2 H2 109.5 . . ?
C10 O4 C11 116.43(16) . . ?
C1 N1 C2 118.55(15) . . ?
N1 C1 C9 124.20(15) . . ?
N1 C1 S1 115.24(13) . . ?
C9 C1 S1 120.55(13) . . ?
N1 C2 C7 122.82(15) . . ?
N1 C2 C3 117.44(15) . . ?
C7 C2 C3 119.74(15) . . ?
C4 C3 C2 119.78(16) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
O1 C4 C3 124.39(16) . . ?
O1 C4 C5 114.89(15) . . ?
C3 C4 C5 120.72(16) . . ?
C6 C5 C4 119.89(16) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C7 120.82(16) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C2 C7 C6 119.05(15) . . ?
C2 C7 C8 117.55(15) . . ?
C6 C7 C8 123.40(15) . . ?
O2 C8 C9 123.29(16) . . ?
O2 C8 C7 116.50(15) . . ?
C9 C8 C7 120.21(16) . . ?
C8 C9 C1 116.66(15) . . ?
C8 C9 C10 117.00(16) . . ?
C1 C9 C10 126.32(16) . . ?
O3 C10 O4 121.23(16) . . ?
O3 C10 C9 123.62(17) . . ?
O4 C10 C9 115.14(16) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S1 C12 H12A 107.4(18) . . ?
S1 C12 H12B 109.1(17) . . ?
H12A C12 H12B 114(2) . . ?
S1 C12 H12C 107.0(16) . . ?
H12A C12 H12C 112(2) . . ?
H12B C12 H12C 108(2) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C2 N1 C1 C9 0.3(3) . . . . ?
C2 N1 C1 S1 179.43(12) . . . . ?
C12 S1 C1 N1 0.99(18) . . . . ?
C12 S1 C1 C9 -179.80(16) . . . . ?
C1 N1 C2 C7 -1.0(2) . . . . ?
C1 N1 C2 C3 179.41(15) . . . . ?
N1 C2 C3 C4 178.94(16) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C13 O1 C4 C3 -1.8(3) . . . . ?
C13 O1 C4 C5 178.67(17) . . . . ?
C2 C3 C4 O1 -178.87(16) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
O1 C4 C5 C6 179.42(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
N1 C2 C7 C6 -179.37(16) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
N1 C2 C7 C8 1.0(2) . . . . ?
C3 C2 C7 C8 -179.38(16) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C5 C6 C7 C8 179.87(17) . . . . ?
C2 C7 C8 O2 179.61(15) . . . . ?
C6 C7 C8 O2 0.0(3) . . . . ?
C2 C7 C8 C9 -0.3(2) . . . . ?
C6 C7 C8 C9 -179.95(16) . . . . ?
O2 C8 C9 C1 179.76(16) . . . . ?
C7 C8 C9 C1 -0.3(2) . . . . ?
O2 C8 C9 C10 -1.7(3) . . . . ?
C7 C8 C9 C10 178.24(16) . . . . ?
N1 C1 C9 C8 0.4(3) . . . . ?
S1 C1 C9 C8 -178.78(13) . . . . ?
N1 C1 C9 C10 -178.02(17) . . . . ?
S1 C1 C9 C10 2.8(2) . . . . ?
C11 O4 C10 O3 -1.2(3) . . . . ?
C11 O4 C10 C9 178.18(18) . . . . ?
C8 C9 C10 O3 1.9(3) . . . . ?
C1 C9 C10 O3 -179.70(18) . . . . ?
C8 C9 C10 O4 -177.46(16) . . . . ?
C1 C9 C10 O4 0.9(3) . . . . ?

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
O2 H2 O3 0.82 1.81 2.5331(18) 145.7 .
O2 H2 O1 0.82 2.55 3.0554(18) 120.8 2_646

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.44
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.067
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, Methanol'
####################################################################### 
# 
# 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_20161229_0m
_database_code_depnum_ccdc_archive 'CCDC 1534621'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Methyl 8-methoxy-2-(methylthio)-4-oxo-1,4-dihydroquinoline-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N O5 S'
_chemical_formula_weight         297.32

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                   7.2268(3)
_cell_length_b                   9.0737(4)
_cell_length_c                   10.4696(4)
_cell_angle_alpha                80.813(2)
_cell_angle_beta                 84.674(2)
_cell_angle_gamma                88.958(3)
_cell_volume                     674.80(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    5192
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9172
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3359
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         28.48
_reflns_number_total             3359
_reflns_number_gt                2808
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.1004P)²+0.1146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3359
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.73572(8) 0.05405(5) 0.39168(4) 0.05486(19) Uani 1 1 d . . .
O1 O 0.65527(18) 0.32919(13) -0.04966(11) 0.0497(3) Uani 1 1 d . . .
O2 O 0.85323(19) -0.31092(12) 0.06660(11) 0.0497(3) Uani 1 1 d . . .
O3 O 0.7375(3) -0.38555(17) 0.34197(16) 0.0895(6) Uani 1 1 d . . .
O4 O 0.9012(2) -0.22399(15) 0.42116(12) 0.0561(4) Uani 1 1 d . . .
N1 N 0.73462(18) 0.10966(13) 0.13479(11) 0.0363(3) Uani 1 1 d . . .
H1A H 0.7197 0.2004 0.1482 0.044 Uiso 1 1 calc R . .
C1 C 0.7577(2) 0.00191(16) 0.23650(13) 0.0344(3) Uani 1 1 d . . .
C2 C 0.73421(18) 0.07936(16) 0.00975(13) 0.0320(3) Uani 1 1 d . . .
C3 C 0.6943(2) 0.19700(17) -0.09024(14) 0.0365(3) Uani 1 1 d . . .
C4 C 0.6968(2) 0.1678(2) -0.21508(15) 0.0436(4) Uani 1 1 d . . .
H4A H 0.6717 0.2440 -0.2819 0.052 Uiso 1 1 calc R . .
C5 C 0.7369(3) 0.0243(2) -0.24209(16) 0.0479(4) Uani 1 1 d . . .
H5A H 0.7393 0.0063 -0.3272 0.057 Uiso 1 1 calc R . .
C6 C 0.7729(2) -0.09093(18) -0.14531(15) 0.0420(4) Uani 1 1 d . . .
H6A H 0.7980 -0.1862 -0.1648 0.050 Uiso 1 1 calc R . .
C7 C 0.77157(19) -0.06395(16) -0.01673(13) 0.0328(3) Uani 1 1 d . . .
C8 C 0.8097(2) -0.18408(16) 0.08956(14) 0.0340(3) Uani 1 1 d . . .
C9 C 0.7918(2) -0.14466(16) 0.21866(14) 0.0339(3) Uani 1 1 d . . .
C10 C 0.8056(2) -0.26587(17) 0.33093(15) 0.0410(4) Uani 1 1 d . . .
C11 C 0.9032(4) -0.3213(2) 0.54372(18) 0.0640(5) Uani 1 1 d . . .
H11A H 0.7953 -0.3840 0.5576 0.096 Uiso 1 1 calc R . .
H11B H 0.9026 -0.2627 0.6124 0.096 Uiso 1 1 calc R . .
H11C H 1.0131 -0.3824 0.5430 0.096 Uiso 1 1 calc R . .
C12 C 0.6038(3) 0.2252(2) 0.3696(2) 0.0585(5) Uani 1 1 d . . .
H12A H 0.5847 0.2625 0.4507 0.088 Uiso 1 1 calc R . .
H12B H 0.4857 0.2066 0.3403 0.088 Uiso 1 1 calc R . .
H12C H 0.6708 0.2978 0.3061 0.088 Uiso 1 1 calc R . .
C13 C 0.6275(3) 0.4562(2) -0.1459(2) 0.0571(5) Uani 1 1 d . . .
H13A H 0.7374 0.4730 -0.2053 0.086 Uiso 1 1 calc R . .
H13B H 0.6025 0.5425 -0.1045 0.086 Uiso 1 1 calc R . .
H13C H 0.5241 0.4385 -0.1927 0.086 Uiso 1 1 calc R . .
O5 O 0.0762(2) 0.61491(15) 0.84050(13) 0.0537(3) Uani 1 1 d . . .
H5B H 0.101(4) 0.519(3) 0.852(3) 0.082(8) Uiso 1 1 d . . .
H5C H -0.006(4) 0.625(3) 0.908(3) 0.071(7) 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 C1 1.7559(15) . ?
S1 C12 1.802(2) . ?
O1 C3 1.3516(19) . ?
O1 C13 1.4294(19) . ?
O2 C8 1.2421(18) . ?
O3 C10 1.185(2) . ?
O4 C10 1.326(2) . ?
O4 C11 1.438(2) . ?
N1 C1 1.3461(18) . ?
N1 C2 1.3803(18) . ?
N1 H1A 0.8600 . ?
C1 C9 1.387(2) . ?
C2 C7 1.389(2) . ?
C2 C3 1.4166(19) . ?
C3 C4 1.373(2) . ?
C4 C5 1.396(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.374(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.405(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.4700(19) . ?
C8 C9 1.446(2) . ?
C9 C10 1.4853(19) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O5 H5B 0.87(3) . ?
O5 H5C 0.89(3) . ?

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
C1 S1 C12 103.58(8) . . ?
C3 O1 C13 117.90(14) . . ?
C10 O4 C11 118.28(15) . . ?
C1 N1 C2 122.18(12) . . ?
C1 N1 H1A 118.9 . . ?
C2 N1 H1A 118.9 . . ?
N1 C1 C9 120.90(13) . . ?
N1 C1 S1 117.23(11) . . ?
C9 C1 S1 121.85(11) . . ?
N1 C2 C7 120.38(12) . . ?
N1 C2 C3 118.65(13) . . ?
C7 C2 C3 120.97(13) . . ?
O1 C3 C4 126.73(13) . . ?
O1 C3 C2 114.47(13) . . ?
C4 C3 C2 118.80(14) . . ?
C3 C4 C5 120.27(14) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 121.27(15) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C7 119.59(15) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C2 C7 C6 119.09(13) . . ?
C2 C7 C8 119.63(13) . . ?
C6 C7 C8 121.28(13) . . ?
O2 C8 C9 123.53(13) . . ?
O2 C8 C7 120.45(13) . . ?
C9 C8 C7 116.02(12) . . ?
C1 C9 C8 120.56(12) . . ?
C1 C9 C10 121.26(13) . . ?
C8 C9 C10 118.16(13) . . ?
O3 C10 O4 122.87(15) . . ?
O3 C10 C9 125.12(15) . . ?
O4 C10 C9 111.99(13) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H5B O5 H5C 103(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
C2 N1 C1 C9 3.4(2) . . . . ?
C2 N1 C1 S1 -174.78(11) . . . . ?
C12 S1 C1 N1 20.78(14) . . . . ?
C12 S1 C1 C9 -157.34(14) . . . . ?
C1 N1 C2 C7 -4.7(2) . . . . ?
C1 N1 C2 C3 175.00(13) . . . . ?
C13 O1 C3 C4 -5.3(2) . . . . ?
C13 O1 C3 C2 175.27(14) . . . . ?
N1 C2 C3 O1 -1.6(2) . . . . ?
C7 C2 C3 O1 178.13(13) . . . . ?
N1 C2 C3 C4 178.93(13) . . . . ?
C7 C2 C3 C4 -1.3(2) . . . . ?
O1 C3 C4 C5 -178.96(16) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
N1 C2 C7 C6 -179.06(13) . . . . ?
C3 C2 C7 C6 1.2(2) . . . . ?
N1 C2 C7 C8 0.7(2) . . . . ?
C3 C2 C7 C8 -179.06(13) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C5 C6 C7 C8 -179.91(15) . . . . ?
C2 C7 C8 O2 -176.08(14) . . . . ?
C6 C7 C8 O2 3.7(2) . . . . ?
C2 C7 C8 C9 4.3(2) . . . . ?
C6 C7 C8 C9 -175.95(13) . . . . ?
N1 C1 C9 C8 2.1(2) . . . . ?
S1 C1 C9 C8 -179.85(11) . . . . ?
N1 C1 C9 C10 -176.09(13) . . . . ?
S1 C1 C9 C10 2.0(2) . . . . ?
O2 C8 C9 C1 174.68(14) . . . . ?
C7 C8 C9 C1 -5.7(2) . . . . ?
O2 C8 C9 C10 -7.1(2) . . . . ?
C7 C8 C9 C10 172.52(13) . . . . ?
C11 O4 C10 O3 -7.6(3) . . . . ?
C11 O4 C10 C9 171.02(15) . . . . ?
C1 C9 C10 O3 136.8(2) . . . . ?
C8 C9 C10 O3 -41.5(3) . . . . ?
C1 C9 C10 O4 -41.9(2) . . . . ?
C8 C9 C10 O4 139.91(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.48
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.066
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, Methanol'
####################################################################### 
# 
# 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_20170522_0m
_database_code_depnum_ccdc_archive 'CCDC 1838137'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Methyl 8-methoxy-2-(methylsulfinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 N O8 S'
_chemical_formula_weight         349.35

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                   7.2412(9)
_cell_length_b                   9.7236(12)
_cell_length_c                   11.4552(15)
_cell_angle_alpha                85.640(6)
_cell_angle_beta                 87.406(6)
_cell_angle_gamma                77.183(6)
_cell_volume                     783.86(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    7691
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            silver-white
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10645
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2965
_reflns_number_gt                2446
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0820P)²+0.0292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2965
_refine_ls_number_parameters     232
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.078
_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 0.03480(6) 0.11210(5) 0.34434(4) 0.03651(19) Uani 1 1 d . . .
O1 O 0.3099(2) -0.29133(15) 0.06376(13) 0.0571(4) Uani 1 1 d . . .
O2 O 0.1824(2) 0.32834(14) -0.03434(12) 0.0516(4) Uani 1 1 d . . .
O3 O 0.1603(2) -0.34107(14) 0.28120(12) 0.0456(4) Uani 1 1 d . . .
O4 O -0.0185(2) 0.26477(14) 0.30094(12) 0.0478(4) Uani 1 1 d . . .
O5 O 0.1075(2) -0.16093(15) 0.39689(13) 0.0530(4) Uani 1 1 d . . .
N1 N 0.1583(2) 0.12477(15) 0.12655(12) 0.0338(4) Uani 1 1 d . . .
H1A H 0.1304 0.2126 0.1410 0.041 Uiso 1 1 calc R . .
C1 C 0.2310(3) 0.1958(2) -0.07265(17) 0.0374(5) Uani 1 1 d . . .
C2 C 0.2890(3) 0.1597(2) -0.18384(17) 0.0444(5) Uani 1 1 d . . .
H2A H 0.2990 0.2293 -0.2427 0.053 Uiso 1 1 calc R . .
C3 C 0.3329(3) 0.0167(2) -0.20791(17) 0.0460(5) Uani 1 1 d . . .
H3A H 0.3697 -0.0073 -0.2839 0.055 Uiso 1 1 calc R . .
C4 C 0.3235(3) -0.0882(2) -0.12337(17) 0.0417(5) Uani 1 1 d . . .
H4B H 0.3545 -0.1822 -0.1419 0.050 Uiso 1 1 calc R . .
C5 C 0.2671(2) -0.0543(2) -0.00868(15) 0.0342(4) Uani 1 1 d . . .
C6 C 0.2198(2) 0.08773(19) 0.01511(15) 0.0316(4) Uani 1 1 d . . .
C7 C 0.1829(4) 0.4454(2) -0.1180(2) 0.0619(7) Uani 1 1 d . . .
H7A H 0.1461 0.5321 -0.0796 0.093 Uiso 1 1 calc R . .
H7B H 0.0952 0.4446 -0.1782 0.093 Uiso 1 1 calc R . .
H7C H 0.3079 0.4379 -0.1524 0.093 Uiso 1 1 calc R . .
C8 C 0.1413(2) 0.02714(19) 0.21222(15) 0.0313(4) Uani 1 1 d . . .
C9 C 0.1864(2) -0.11567(19) 0.19847(16) 0.0337(4) Uani 1 1 d . . .
C10 C 0.2579(3) -0.1657(2) 0.08447(17) 0.0366(4) Uani 1 1 d . . .
C11 C 0.1500(3) -0.2069(2) 0.30137(17) 0.0372(4) Uani 1 1 d . . .
C12 C 0.1153(4) -0.4295(2) 0.3814(2) 0.0570(6) Uani 1 1 d . . .
H12A H 0.1269 -0.5242 0.3590 0.086 Uiso 1 1 calc R . .
H12B H -0.0121 -0.3929 0.4089 0.086 Uiso 1 1 calc R . .
H12C H 0.2014 -0.4298 0.4428 0.086 Uiso 1 1 calc R . .
C13 C 0.2512(3) 0.0987(3) 0.41939(19) 0.0535(6) Uani 1 1 d . . .
H13A H 0.2954 0.0033 0.4509 0.080 Uiso 1 1 calc R . .
H13B H 0.2286 0.1612 0.4820 0.080 Uiso 1 1 calc R . .
H13C H 0.3451 0.1245 0.3654 0.080 Uiso 1 1 calc R . .
O11 O 0.3916(3) 0.4238(2) 0.15506(19) 0.0720(6) Uani 1 1 d D . .
H11A H 0.442(6) 0.396(4) 0.093(2) 0.147(19) Uiso 1 1 d D . .
H11B H 0.348(5) 0.516(4) 0.153(3) 0.114(12) Uiso 1 1 d . . .
O12 O 0.5954(3) 0.3736(2) 0.35615(16) 0.0759(6) Uani 1 1 d D . .
H12D H 0.520(4) 0.385(3) 0.297(2) 0.111(13) Uiso 1 1 d D . .
H12E H 0.706(3) 0.338(3) 0.339(3) 0.094(10) Uiso 1 1 d D . .
O13 O 0.4247(3) 0.3328(3) 0.58289(19) 0.0804(6) Uani 1 1 d D . .
H13D H 0.477(5) 0.328(4) 0.516(2) 0.126(14) Uiso 1 1 d D . .
H13E H 0.458(6) 0.396(4) 0.624(3) 0.159(19) Uiso 1 1 d 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 O4 1.5002(14) . ?
S1 C13 1.796(2) . ?
S1 C8 1.8355(18) . ?
O1 C10 1.233(2) . ?
O2 C1 1.359(2) . ?
O2 C7 1.432(2) . ?
O3 C11 1.328(2) . ?
O3 C12 1.450(2) . ?
O5 C11 1.214(2) . ?
N1 C8 1.334(2) . ?
N1 C6 1.380(2) . ?
N1 H1A 0.8600 . ?
C1 C2 1.370(3) . ?
C1 C6 1.411(2) . ?
C2 C3 1.402(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.363(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.400(3) . ?
C4 H4B 0.9300 . ?
C5 C6 1.392(3) . ?
C5 C10 1.472(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.374(3) . ?
C9 C10 1.461(3) . ?
C9 C11 1.470(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O11 H11A 0.822(19) . ?
O11 H11B 0.88(3) . ?
O12 H12D 0.875(18) . ?
O12 H12E 0.819(17) . ?
O13 H13D 0.835(19) . ?
O13 H13E 0.880(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
O4 S1 C13 103.87(10) . . ?
O4 S1 C8 102.10(8) . . ?
C13 S1 C8 97.17(9) . . ?
C1 O2 C7 118.08(17) . . ?
C11 O3 C12 115.22(16) . . ?
C8 N1 C6 121.35(15) . . ?
C8 N1 H1A 119.3 . . ?
C6 N1 H1A 119.3 . . ?
O2 C1 C2 126.96(17) . . ?
O2 C1 C6 113.99(17) . . ?
C2 C1 C6 119.05(18) . . ?
C1 C2 C3 119.22(18) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 122.01(19) . . ?
C4 C3 H3A 119.0 . . ?
C2 C3 H3A 119.0 . . ?
C3 C4 C5 119.88(19) . . ?
C3 C4 H4B 120.1 . . ?
C5 C4 H4B 120.1 . . ?
C6 C5 C4 118.29(17) . . ?
C6 C5 C10 120.80(16) . . ?
C4 C5 C10 120.91(17) . . ?
N1 C6 C5 119.64(15) . . ?
N1 C6 C1 118.82(16) . . ?
C5 C6 C1 121.54(17) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 123.67(16) . . ?
N1 C8 S1 110.21(13) . . ?
C9 C8 S1 125.99(13) . . ?
C8 C9 C10 119.13(15) . . ?
C8 C9 C11 115.89(16) . . ?
C10 C9 C11 124.92(17) . . ?
O1 C10 C9 124.50(17) . . ?
O1 C10 C5 120.17(17) . . ?
C9 C10 C5 115.33(16) . . ?
O5 C11 O3 122.75(17) . . ?
O5 C11 C9 121.99(17) . . ?
O3 C11 C9 115.23(17) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H11A O11 H11B 113(3) . . ?
H12D O12 H12E 113(3) . . ?
H13D O13 H13E 113(4) . . ?

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
C7 O2 C1 C2 2.8(3) . . . . ?
C7 O2 C1 C6 -177.85(17) . . . . ?
O2 C1 C2 C3 -179.74(18) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C3 C4 C5 C10 -179.28(17) . . . . ?
C8 N1 C6 C5 -0.6(3) . . . . ?
C8 N1 C6 C1 178.59(15) . . . . ?
C4 C5 C6 N1 178.09(16) . . . . ?
C10 C5 C6 N1 -1.9(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C10 C5 C6 C1 178.88(16) . . . . ?
O2 C1 C6 N1 1.7(2) . . . . ?
C2 C1 C6 N1 -178.93(16) . . . . ?
O2 C1 C6 C5 -179.13(16) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C6 N1 C8 C9 1.5(3) . . . . ?
C6 N1 C8 S1 -174.48(13) . . . . ?
O4 S1 C8 N1 7.21(15) . . . . ?
C13 S1 C8 N1 -98.70(15) . . . . ?
O4 S1 C8 C9 -168.68(16) . . . . ?
C13 S1 C8 C9 85.41(18) . . . . ?
N1 C8 C9 C10 0.2(3) . . . . ?
S1 C8 C9 C10 175.58(13) . . . . ?
N1 C8 C9 C11 -177.27(16) . . . . ?
S1 C8 C9 C11 -1.9(2) . . . . ?
C8 C9 C10 O1 176.90(18) . . . . ?
C11 C9 C10 O1 -5.9(3) . . . . ?
C8 C9 C10 C5 -2.6(3) . . . . ?
C11 C9 C10 C5 174.67(16) . . . . ?
C6 C5 C10 O1 -176.07(18) . . . . ?
C4 C5 C10 O1 3.9(3) . . . . ?
C6 C5 C10 C9 3.4(3) . . . . ?
C4 C5 C10 C9 -176.59(17) . . . . ?
C12 O3 C11 O5 0.6(3) . . . . ?
C12 O3 C11 C9 -177.13(17) . . . . ?
C8 C9 C11 O5 -9.7(3) . . . . ?
C10 C9 C11 O5 172.96(18) . . . . ?
C8 C9 C11 O3 167.99(16) . . . . ?
C10 C9 C11 O3 -9.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, Methanol'
####################################################################### 
# 
# 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_20171102_0m
_database_code_depnum_ccdc_archive 'CCDC 1838136'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Methyl 5-methoxy-2-(methylsulfinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O5 S'
_chemical_formula_weight         331.33

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   6.6266(6)
_cell_length_b                   18.2993(15)
_cell_length_c                   11.8645(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.670(6)
_cell_angle_gamma                90.00
_cell_volume                     1418.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    3965
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.33

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9273
_exptl_absorpt_correction_T_max  0.9412
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2776
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2776
_reflns_number_gt                2120
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.1395P)²+1.5612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2512
_refine_ls_wR_factor_gt          0.2396
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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 0.69267(16) 0.89690(6) 0.14128(10) 0.0457(4) Uani 1 1 d . . .
O1 O 0.6436(5) 0.97134(18) 0.0917(3) 0.0631(10) Uani 1 1 d . . .
O2 O -0.1521(4) 0.69098(16) -0.0721(3) 0.0483(8) Uani 1 1 d . . .
O3 O 0.2063(5) 0.67149(16) 0.0547(3) 0.0591(10) Uani 1 1 d . . .
O4 O 0.7584(5) 0.75895(17) 0.2123(3) 0.0559(9) Uani 1 1 d . . .
O5 O 0.6035(4) 0.65805(15) 0.1358(3) 0.0492(8) Uani 1 1 d . . .
N1 N 0.3179(5) 0.88818(18) 0.0259(3) 0.0397(8) Uani 1 1 d . . .
H1B H 0.3443 0.9340 0.0208 0.048 Uiso 1 1 calc R . .
C1 C 0.6419(9) 0.9049(3) 0.2826(4) 0.0607(13) Uani 1 1 d . . .
H1C H 0.7505 0.9318 0.3282 0.091 Uiso 1 1 calc R . .
H1D H 0.6331 0.8571 0.3146 0.091 Uiso 1 1 calc R . .
H1E H 0.5148 0.9303 0.2815 0.091 Uiso 1 1 calc R . .
C2 C 0.4602(6) 0.8447(2) 0.0855(3) 0.0364(9) Uani 1 1 d . . .
C3 C 0.1303(6) 0.8620(2) -0.0276(3) 0.0368(9) Uani 1 1 d . . .
C4 C -0.0086(6) 0.9108(2) -0.0894(4) 0.0457(11) Uani 1 1 d . . .
H4A H 0.0233 0.9601 -0.0926 0.055 Uiso 1 1 calc R . .
C5 C -0.1906(7) 0.8851(3) -0.1446(4) 0.0517(12) Uani 1 1 d . . .
H5A H -0.2828 0.9174 -0.1861 0.062 Uiso 1 1 calc R . .
C6 C -0.2425(6) 0.8116(2) -0.1405(4) 0.0468(11) Uani 1 1 d . . .
H6A H -0.3680 0.7953 -0.1796 0.056 Uiso 1 1 calc R . .
C7 C -0.1088(6) 0.7629(2) -0.0789(3) 0.0368(9) Uani 1 1 d . . .
C8 C 0.0865(6) 0.7869(2) -0.0199(3) 0.0331(8) Uani 1 1 d . . .
C9 C 0.2403(6) 0.7368(2) 0.0438(3) 0.0357(9) Uani 1 1 d . . .
C10 C 0.4351(6) 0.7710(2) 0.0951(3) 0.0337(8) Uani 1 1 d . . .
C11 C -0.3385(7) 0.6646(3) -0.1387(4) 0.0545(12) Uani 1 1 d . . .
H11A H -0.3508 0.6131 -0.1261 0.082 Uiso 1 1 calc R . .
H11B H -0.3366 0.6734 -0.2183 0.082 Uiso 1 1 calc R . .
H11C H -0.4528 0.6896 -0.1163 0.082 Uiso 1 1 calc R . .
C12 C 0.6140(6) 0.7294(2) 0.1547(3) 0.0368(9) Uani 1 1 d . . .
C13 C 0.7861(8) 0.6173(3) 0.1842(5) 0.0616(14) Uani 1 1 d . . .
H13A H 0.7654 0.5663 0.1669 0.092 Uiso 1 1 calc R . .
H13B H 0.8128 0.6239 0.2657 0.092 Uiso 1 1 calc R . .
H13C H 0.9007 0.6348 0.1522 0.092 Uiso 1 1 calc R . .
Q11 C 0.092(2) 0.0225(7) 0.4506(16) 0.150(6) Uani 1 1 d . . .
Q12 C 0.245(3) 0.0226(8) 0.4344(14) 0.171(6) Uani 1 1 d . . .
Q13 C 0.479(4) 0.0304(9) 0.4895(19) 0.246(9) 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
S1 O1 1.498(3) . ?
S1 C1 1.771(6) . ?
S1 C2 1.839(4) . ?
O2 C7 1.353(5) . ?
O2 C11 1.433(5) . ?
O3 C9 1.226(5) . ?
O4 C12 1.207(5) . ?
O5 C12 1.324(5) . ?
O5 C13 1.455(5) . ?
N1 C2 1.340(5) . ?
N1 C3 1.383(5) . ?
N1 H1B 0.8600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C2 C10 1.366(5) . ?
C3 C4 1.398(5) . ?
C3 C8 1.411(5) . ?
C4 C5 1.355(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.391(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.377(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.433(5) . ?
C8 C9 1.481(5) . ?
C9 C10 1.472(5) . ?
C10 C12 1.484(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
Q11 Q12 1.07(2) . ?
Q11 Q11 2.00(3) 3_556 ?
Q12 Q13 1.58(3) . ?
Q13 Q13 1.17(3) 3_656 ?

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 C1 103.5(2) . . ?
O1 S1 C2 102.56(18) . . ?
C1 S1 C2 95.9(2) . . ?
C7 O2 C11 117.8(3) . . ?
C12 O5 C13 114.9(3) . . ?
C2 N1 C3 122.3(3) . . ?
C2 N1 H1B 118.8 . . ?
C3 N1 H1B 118.8 . . ?
S1 C1 H1C 109.5 . . ?
S1 C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
S1 C1 H1E 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
N1 C2 C10 123.0(3) . . ?
N1 C2 S1 110.7(3) . . ?
C10 C2 S1 126.1(3) . . ?
N1 C3 C4 118.8(4) . . ?
N1 C3 C8 119.1(3) . . ?
C4 C3 C8 122.1(4) . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C7 C6 C5 120.2(4) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
O2 C7 C6 122.5(3) . . ?
O2 C7 C8 116.9(3) . . ?
C6 C7 C8 120.6(4) . . ?
C3 C8 C7 116.4(3) . . ?
C3 C8 C9 120.4(3) . . ?
C7 C8 C9 123.2(3) . . ?
O3 C9 C10 122.4(3) . . ?
O3 C9 C8 122.3(3) . . ?
C10 C9 C8 115.4(3) . . ?
C2 C10 C9 119.8(3) . . ?
C2 C10 C12 116.6(3) . . ?
C9 C10 C12 123.6(3) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O5 123.5(4) . . ?
O4 C12 C10 122.3(4) . . ?
O5 C12 C10 114.2(3) . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Q12 Q11 Q11 143(2) . 3_556 ?
Q11 Q12 Q13 145(2) . . ?
Q13 Q13 Q12 101(3) 3_656 . ?

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
C3 N1 C2 C10 2.3(6) . . . . ?
C3 N1 C2 S1 178.4(3) . . . . ?
O1 S1 C2 N1 -3.8(3) . . . . ?
C1 S1 C2 N1 101.5(3) . . . . ?
O1 S1 C2 C10 172.1(4) . . . . ?
C1 S1 C2 C10 -82.7(4) . . . . ?
C2 N1 C3 C4 -179.1(4) . . . . ?
C2 N1 C3 C8 -0.3(6) . . . . ?
N1 C3 C4 C5 178.2(4) . . . . ?
C8 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C5 C6 C7 0.4(8) . . . . ?
C11 O2 C7 C6 4.6(6) . . . . ?
C11 O2 C7 C8 -174.5(4) . . . . ?
C5 C6 C7 O2 179.9(4) . . . . ?
C5 C6 C7 C8 -1.1(7) . . . . ?
N1 C3 C8 C7 -178.9(4) . . . . ?
C4 C3 C8 C7 -0.1(6) . . . . ?
N1 C3 C8 C9 -0.5(6) . . . . ?
C4 C3 C8 C9 178.3(4) . . . . ?
O2 C7 C8 C3 180.0(3) . . . . ?
C6 C7 C8 C3 0.9(6) . . . . ?
O2 C7 C8 C9 1.6(6) . . . . ?
C6 C7 C8 C9 -177.4(4) . . . . ?
C3 C8 C9 O3 178.3(4) . . . . ?
C7 C8 C9 O3 -3.5(6) . . . . ?
C3 C8 C9 C10 -0.6(5) . . . . ?
C7 C8 C9 C10 177.7(4) . . . . ?
N1 C2 C10 C9 -3.4(6) . . . . ?
S1 C2 C10 C9 -178.8(3) . . . . ?
N1 C2 C10 C12 174.4(4) . . . . ?
S1 C2 C10 C12 -1.0(5) . . . . ?
O3 C9 C10 C2 -176.4(4) . . . . ?
C8 C9 C10 C2 2.5(5) . . . . ?
O3 C9 C10 C12 5.9(6) . . . . ?
C8 C9 C10 C12 -175.2(3) . . . . ?
C13 O5 C12 O4 -3.6(6) . . . . ?
C13 O5 C12 C10 174.2(4) . . . . ?
C2 C10 C12 O4 15.0(6) . . . . ?
C9 C10 C12 O4 -167.2(4) . . . . ?
C2 C10 C12 O5 -162.8(4) . . . . ?
C9 C10 C12 O5 14.9(6) . . . . ?
Q11 Q11 Q12 Q13 -52(5) 3_556 . . . ?
Q11 Q12 Q13 Q13 91(4) . . . 3_656 ?

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
N1 H1B O1 0.86 2.20 2.957(4) 147.1 3_675
N1 H1B O1 0.86 2.13 2.649(4) 118.1 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.094
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, Methanol'
