# 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_SMBACPR12
_database_code_depnum_ccdc_archive 'CCDC 1414163'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; caprolactam'
_chemical_name_common            'Sulfonamide benzoic acid; caprolactam'
_chemical_melting_point          426
_chemical_formula_moiety         C7H7NO4S,2(C6H11NO)
_chemical_formula_sum            'C19 H29 N3 O6 S'
_chemical_formula_weight         427.51

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   7.0964(5)
_cell_length_b                   16.230(2)
_cell_length_c                   19.1256(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2202.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    774
_cell_measurement_theta_min      3.5140
_cell_measurement_theta_max      60.5840

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    1.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31385
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7278
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_sigmaI/netI    0.1565
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         65.08
_reflns_number_total             3745
_reflns_number_gt                1118
_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)+(0.0614P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_number_reflns         3745
_refine_ls_number_parameters     282
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2338
_refine_ls_R_factor_gt           0.0872
_refine_ls_wR_factor_ref         0.2387
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_restrained_S_all      0.931
_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
C10 C 0.7620(17) 0.3355(8) 0.5408(6) 0.139(5) Uani 1 1 d . . .
H10A H 0.8124 0.2803 0.5352 0.166 Uiso 1 1 calc R . .
H10B H 0.6422 0.3308 0.5649 0.166 Uiso 1 1 calc R . .
S1 S -0.0614(4) 0.3825(2) 0.02628(15) 0.0986(9) Uani 1 1 d . . .
N1 N -0.0279(15) 0.3054(6) -0.0237(5) 0.098(3) Uani 1 1 d . . .
O2 O -0.2553(8) 0.3807(6) 0.0500(3) 0.130(3) Uani 1 1 d . . .
O4 O 0.6057(10) 0.3292(5) 0.2670(3) 0.116(2) Uani 1 1 d D . .
O6 O 0.3446(10) 0.3236(5) 0.9275(4) 0.114(2) Uani 1 1 d . . .
C5 C 0.1110(13) 0.3363(6) 0.2213(5) 0.101(3) Uani 1 1 d . . .
H5 H 0.0564 0.3226 0.2640 0.121 Uiso 1 1 calc R . .
O5 O 0.8424(9) 0.3049(5) 0.3656(4) 0.105(2) Uani 1 1 d . . .
C1 C 0.0795(12) 0.3704(6) 0.1013(4) 0.080(3) Uani 1 1 d . . .
C2 C 0.2758(13) 0.3802(7) 0.0953(5) 0.098(3) Uani 1 1 d . . .
H2 H 0.3297 0.3934 0.0524 0.118 Uiso 1 1 calc R . .
O3 O 0.3642(10) 0.3271(7) 0.3381(4) 0.153(4) Uani 1 1 d . . .
C4 C 0.3075(14) 0.3457(7) 0.2164(5) 0.093(3) Uani 1 1 d . . .
C6 C -0.0002(13) 0.3472(7) 0.1636(4) 0.098(3) Uani 1 1 d . . .
H6 H -0.1296 0.3390 0.1666 0.117 Uiso 1 1 calc R . .
N2 N 1.0532(14) 0.3703(7) 0.4294(5) 0.109(3) Uani 1 1 d D . .
C7 C 0.4232(15) 0.3338(8) 0.2802(6) 0.103(3) Uani 1 1 d . . .
O1 O 0.0056(10) 0.4526(4) -0.0135(4) 0.118(3) Uani 1 1 d . . .
C3 C 0.3884(13) 0.3701(7) 0.1542(5) 0.107(4) Uani 1 1 d . . .
H3 H 0.5174 0.3797 0.1517 0.129 Uiso 1 1 calc R . .
C8 C 0.8786(16) 0.3484(7) 0.4186(6) 0.102(4) Uani 1 1 d . . .
C9 C 0.7281(13) 0.3716(8) 0.4702(6) 0.121(4) Uani 1 1 d . . .
H9A H 0.7229 0.4311 0.4741 0.145 Uiso 1 1 calc R . .
H9B H 0.6071 0.3527 0.4529 0.145 Uiso 1 1 calc R . .
C14 C 0.4096(18) 0.3673(10) 0.8813(6) 0.129(5) Uani 1 1 d . . .
N3 N 0.5899(16) 0.3847(10) 0.8780(6) 0.147(4) Uani 1 1 d D . .
C17 C 0.488(2) 0.4278(9) 0.7216(6) 0.161(6) Uani 1 1 d . . .
H17A H 0.4611 0.4854 0.7125 0.193 Uiso 1 1 calc R . .
H17B H 0.5027 0.4007 0.6768 0.193 Uiso 1 1 calc R . .
C12 C 1.1014(18) 0.3836(9) 0.5582(6) 0.143(5) Uani 1 1 d . . .
H12A H 1.1835 0.4121 0.5907 0.172 Uiso 1 1 calc R . .
H12B H 1.1438 0.3269 0.5548 0.172 Uiso 1 1 calc R . .
C16 C 0.3225(19) 0.3905(12) 0.7587(7) 0.202(8) Uani 1 1 d . . .
H16A H 0.2114 0.4109 0.7347 0.243 Uiso 1 1 calc R . .
H16B H 0.3281 0.3318 0.7494 0.243 Uiso 1 1 calc R . .
C15 C 0.2893(19) 0.3977(12) 0.8230(7) 0.236(12) Uani 1 1 d . . .
H15A H 0.1664 0.3730 0.8303 0.284 Uiso 1 1 calc R . .
H15B H 0.2733 0.4563 0.8312 0.284 Uiso 1 1 calc R . .
C19 C 0.689(2) 0.4396(11) 0.8271(8) 0.212(9) Uani 1 1 d . . .
H19A H 0.6408 0.4951 0.8338 0.254 Uiso 1 1 calc R . .
H19B H 0.8212 0.4405 0.8396 0.254 Uiso 1 1 calc R . .
C11 C 0.8971(18) 0.3853(8) 0.5863(6) 0.133(4) Uani 1 1 d . . .
H11A H 0.8955 0.3633 0.6335 0.159 Uiso 1 1 calc R . .
H11B H 0.8539 0.4420 0.5884 0.159 Uiso 1 1 calc R . .
C13 C 1.1146(16) 0.4241(7) 0.4870(6) 0.134(5) Uani 1 1 d . . .
H13A H 1.0377 0.4735 0.4870 0.161 Uiso 1 1 calc R . .
H13B H 1.2441 0.4407 0.4788 0.161 Uiso 1 1 calc R . .
C18 C 0.677(2) 0.4226(11) 0.7608(8) 0.195(8) Uani 1 1 d . . .
H18A H 0.7243 0.3669 0.7548 0.235 Uiso 1 1 calc R . .
H18B H 0.7647 0.4588 0.7368 0.235 Uiso 1 1 calc R . .
H1B H -0.068(8) 0.261(3) -0.002(3) 0.021(16) Uiso 1 1 d . . .
H3A H 0.664(16) 0.361(9) 0.911(5) 0.20(8) Uiso 1 1 d D . .
H1A H -0.047(16) 0.311(6) -0.066(5) 0.14(5) Uiso 1 1 d . . .
H4A H 0.679(8) 0.328(4) 0.306(2) 0.06(2) Uiso 1 1 d D . .
H2A H 1.126(10) 0.367(5) 0.391(3) 0.09(3) 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
C10 C9 1.492(12) . ?
C10 C11 1.527(13) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
S1 O1 1.449(6) . ?
S1 O2 1.449(6) . ?
S1 N1 1.593(10) . ?
S1 C1 1.760(8) . ?
N1 H1B 0.88(5) . ?
N1 H1A 0.83(9) . ?
O4 C7 1.322(11) . ?
O4 H4A 0.91(2) . ?
O6 C14 1.223(12) . ?
C5 C6 1.369(11) . ?
C5 C4 1.406(11) . ?
C5 H5 0.9300 . ?
O5 C8 1.263(12) . ?
C1 C6 1.371(10) . ?
C1 C2 1.407(11) . ?
C2 C3 1.392(11) . ?
C2 H2 0.9300 . ?
O3 C7 1.188(11) . ?
C4 C3 1.378(11) . ?
C4 C7 1.483(13) . ?
C6 H6 0.9300 . ?
N2 C8 1.305(12) . ?
N2 C13 1.473(12) . ?
N2 H2A 0.90(2) . ?
C3 H3 0.9300 . ?
C8 C9 1.501(13) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 N3 1.312(13) . ?
C14 C15 1.490(15) . ?
N3 C19 1.495(17) . ?
N3 H3A 0.91(2) . ?
C17 C16 1.502(16) . ?
C17 C18 1.538(17) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C12 C13 1.515(13) . ?
C12 C11 1.546(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C16 C15 1.258(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C19 C18 1.300(14) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
C9 C10 C11 114.2(11) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
O1 S1 O2 119.5(5) . . ?
O1 S1 N1 104.7(4) . . ?
O2 S1 N1 108.3(6) . . ?
O1 S1 C1 109.3(5) . . ?
O2 S1 C1 106.3(4) . . ?
N1 S1 C1 108.4(5) . . ?
S1 N1 H1B 108(4) . . ?
S1 N1 H1A 118(8) . . ?
H1B N1 H1A 121(9) . . ?
C7 O4 H4A 114(4) . . ?
C6 C5 C4 120.2(10) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C1 C2 120.7(9) . . ?
C6 C1 S1 120.3(7) . . ?
C2 C1 S1 118.8(8) . . ?
C3 C2 C1 119.2(9) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C3 C4 C5 120.2(9) . . ?
C3 C4 C7 121.1(10) . . ?
C5 C4 C7 118.6(10) . . ?
C5 C6 C1 119.9(9) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 N2 C13 124.1(11) . . ?
C8 N2 H2A 113(6) . . ?
C13 N2 H2A 119(6) . . ?
O3 C7 O4 121.2(11) . . ?
O3 C7 C4 125.7(10) . . ?
O4 C7 C4 113.1(11) . . ?
C4 C3 C2 119.6(9) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O5 C8 N2 118.2(12) . . ?
O5 C8 C9 121.5(10) . . ?
N2 C8 C9 120.3(12) . . ?
C10 C9 C8 112.4(9) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
O6 C14 N3 121.8(14) . . ?
O6 C14 C15 121.1(13) . . ?
N3 C14 C15 116.8(14) . . ?
C14 N3 C19 128.1(15) . . ?
C14 N3 H3A 116(10) . . ?
C19 N3 H3A 116(9) . . ?
C16 C17 C18 115.5(10) . . ?
C16 C17 H17A 108.4 . . ?
C18 C17 H17A 108.4 . . ?
C16 C17 H17B 108.4 . . ?
C18 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C13 C12 C11 111.3(11) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C15 C16 C17 124.8(16) . . ?
C15 C16 H16A 106.1 . . ?
C17 C16 H16A 106.1 . . ?
C15 C16 H16B 106.1 . . ?
C17 C16 H16B 106.1 . . ?
H16A C16 H16B 106.3 . . ?
C16 C15 C14 126.5(16) . . ?
C16 C15 H15A 105.7 . . ?
C14 C15 H15A 105.7 . . ?
C16 C15 H15B 105.7 . . ?
C14 C15 H15B 105.7 . . ?
H15A C15 H15B 106.1 . . ?
C18 C19 N3 118.6(15) . . ?
C18 C19 H19A 107.7 . . ?
N3 C19 H19A 107.7 . . ?
C18 C19 H19B 107.7 . . ?
N3 C19 H19B 107.7 . . ?
H19A C19 H19B 107.1 . . ?
C10 C11 C12 112.4(10) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N2 C13 C12 113.4(10) . . ?
N2 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C19 C18 C17 121.2(17) . . ?
C19 C18 H18A 107.0 . . ?
C17 C18 H18A 107.0 . . ?
C19 C18 H18B 107.0 . . ?
C17 C18 H18B 107.0 . . ?
H18A C18 H18B 106.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        65.08
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.051
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAHPFORMI
_database_code_depnum_ccdc_archive 'CCDC 1414164'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; 2pyridone f'
_chemical_name_common            'Sulfonamide benzoic acid; 2pyridone form I'
_chemical_melting_point          414
_chemical_formula_moiety         C7H7NO4S,C5H5NO
_chemical_formula_sum            'C48 H48 N8 O20 S4'
_chemical_formula_weight         1185.22

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'

_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                   14.990(4)
_cell_length_b                   11.3156(3)
_cell_length_c                   7.90(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.96(11)
_cell_angle_gamma                90.00
_cell_volume                     1333(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2558
_cell_measurement_theta_min      4.9550
_cell_measurement_theta_max      71.8710

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    2.378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4278
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.91
_diffrn_reflns_theta_max         65.08
_reflns_number_total             2255
_reflns_number_gt                2050
_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)+(0.1353P)²+0.4093P] 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         2255
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1880
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.28867(4) 0.83448(6) 0.59019(8) 0.0509(3) Uani 1 1 d . . .
O2 O 0.32985(13) 0.72045(18) 0.6172(3) 0.0645(6) Uani 1 1 d . . .
O3 O -0.13281(16) 0.8580(2) 0.2195(4) 0.0842(8) Uani 1 1 d . . .
O4 O -0.12030(15) 0.66483(19) 0.2533(4) 0.0784(8) Uani 1 1 d . . .
H4A H -0.1702 0.6648 0.2014 0.094 Uiso 1 1 d R . .
O1 O 0.28738(15) 0.9131(2) 0.7313(3) 0.0711(7) Uani 1 1 d . . .
N1 N 0.33963(14) 0.9023(2) 0.4519(3) 0.0546(6) Uani 1 1 d . . .
H1A H 0.3429 0.8633 0.3718 0.066 Uiso 1 1 d R . .
H1B H 0.3200 0.9841 0.4297 0.066 Uiso 1 1 d R . .
C4 C 0.00325(16) 0.7820(3) 0.3546(3) 0.0495(6) Uani 1 1 d . . .
C2 C 0.14139(19) 0.6988(3) 0.4801(4) 0.0557(7) Uani 1 1 d . . .
H2 H 0.1763 0.6332 0.5136 0.067 Uiso 1 1 calc R . .
C7 C -0.09059(18) 0.7728(3) 0.2685(4) 0.0543(7) Uani 1 1 d . . .
C6 C 0.1253(2) 0.9094(3) 0.4545(4) 0.0615(8) Uani 1 1 d . . .
H6 H 0.1487 0.9849 0.4738 0.074 Uiso 1 1 calc R . .
C1 C 0.17613(16) 0.8113(2) 0.5019(3) 0.0472(6) Uani 1 1 d . . .
C5 C 0.03926(19) 0.8940(3) 0.3779(4) 0.0603(8) Uani 1 1 d . . .
H5 H 0.0051 0.9596 0.3416 0.072 Uiso 1 1 calc R . .
C3 C 0.0538(2) 0.6848(3) 0.4077(4) 0.0573(7) Uani 1 1 d . . .
H3 H 0.0291 0.6095 0.3950 0.069 Uiso 1 1 calc R . .
O5 O 0.27552(13) 0.35607(18) -0.0828(3) 0.0627(6) Uani 1 1 d . . .
N2 N 0.40853(19) 0.3046(3) 0.0886(4) 0.0765(9) Uani 1 1 d . . .
H2A H 0.4234 0.3809 0.1071 0.092 Uiso 1 1 d R . .
C9 C 0.30697(16) 0.1627(2) -0.0309(3) 0.0402(6) Uani 1 1 d . . .
H9 H 0.2531 0.1430 -0.0937 0.048 Uiso 1 1 calc R . .
C8 C 0.32732(17) 0.2787(2) -0.0118(3) 0.0489(6) Uani 1 1 d . . .
C12 C 0.46135(19) 0.2158(3) 0.1568(4) 0.0648(8) Uani 1 1 d . . .
H12 H 0.5149 0.2339 0.2219 0.078 Uiso 1 1 calc R . .
C10 C 0.3596(2) 0.0732(3) 0.0351(4) 0.0610(7) Uani 1 1 d . . .
H10 H 0.3424 -0.0048 0.0139 0.073 Uiso 1 1 calc R . .
C11 C 0.4366(2) 0.0972(3) 0.1309(4) 0.0664(8) Uani 1 1 d . . .
H11 H 0.4728 0.0366 0.1790 0.080 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 O1 1.428(3) . ?
S1 O2 1.437(2) . ?
S1 N1 1.594(3) . ?
S1 C1 1.777(3) . ?
O3 C7 1.195(4) . ?
O4 C7 1.302(3) . ?
O4 H4A 0.8146 . ?
N1 H1A 0.7770 . ?
N1 H1B 0.9815 . ?
C4 C3 1.377(4) . ?
C4 C5 1.382(4) . ?
C4 C7 1.501(4) . ?
C2 C1 1.380(4) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9300 . ?
C6 C1 1.376(4) . ?
C6 C5 1.377(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
O5 C8 1.262(3) . ?
N2 C12 1.356(4) . ?
N2 C8 1.413(4) . ?
N2 H2A 0.8998 . ?
C9 C8 1.352(4) . ?
C9 C10 1.355(4) . ?
C9 H9 0.9300 . ?
C12 C11 1.402(5) . ?
C12 H12 0.9300 . ?
C10 C11 1.341(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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 O2 118.95(16) . . ?
O1 S1 N1 106.34(19) . . ?
O2 S1 N1 107.77(14) . . ?
O1 S1 C1 108.00(16) . . ?
O2 S1 C1 107.57(12) . . ?
N1 S1 C1 107.76(17) . . ?
C7 O4 H4A 109.6 . . ?
S1 N1 H1A 111.1 . . ?
S1 N1 H1B 114.8 . . ?
H1A N1 H1B 115.6 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 C7 122.9(2) . . ?
C5 C4 C7 117.3(2) . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
O3 C7 O4 124.2(2) . . ?
O3 C7 C4 122.0(3) . . ?
O4 C7 C4 113.7(2) . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C1 C2 121.3(2) . . ?
C6 C1 S1 117.7(2) . . ?
C2 C1 S1 121.0(2) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C12 N2 C8 120.2(3) . . ?
C12 N2 H2A 121.5 . . ?
C8 N2 H2A 118.3 . . ?
C8 C9 C10 124.5(2) . . ?
C8 C9 H9 117.7 . . ?
C10 C9 H9 117.7 . . ?
O5 C8 C9 120.1(2) . . ?
O5 C8 N2 124.1(3) . . ?
C9 C8 N2 115.8(2) . . ?
N2 C12 C11 121.1(3) . . ?
N2 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        65.08
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.095
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAHPFORMII
_database_code_depnum_ccdc_archive 'CCDC 1414165'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; 2pyridone form II'
_chemical_name_common            'Sulfonamide benzoic acid; 2pyridone form II'
_chemical_melting_point          411
_chemical_formula_moiety         C7H7NO4S,C5H5NO

_chemical_formula_sum            'C12 H12 N2 O5 S'
_chemical_formula_weight         296.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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                   5.3090(3)
_cell_length_b                   10.5807(8)
_cell_length_c                   12.1499(10)
_cell_angle_alpha                76.377(7)
_cell_angle_beta                 89.187(6)
_cell_angle_gamma                77.195(6)
_cell_volume                     646.28(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2031
_cell_measurement_theta_min      0.79164
_cell_measurement_theta_max      1.0000

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  4.3990
_exptl_absorpt_correction_T_max  71.9310
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3592
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         67.08
_reflns_number_total             2304
_reflns_number_gt                2083
_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)+(0.1041P)²+0.0637P] 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         2304
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_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 0.20835(9) 0.69614(4) 0.49139(4) 0.0422(2) Uani 1 1 d . . .
O3 O 0.8046(3) 1.02139(15) 0.78366(14) 0.0549(4) Uani 1 1 d . . .
O1 O 0.2125(3) 0.55951(15) 0.54367(15) 0.0545(4) Uani 1 1 d . . .
O4 O 1.0051(3) 0.80921(15) 0.85642(14) 0.0562(4) Uani 1 1 d . . .
H4A H 1.0941 0.8434 0.8901 0.084 Uiso 1 1 calc R . .
O2 O -0.0323(3) 0.78959(16) 0.45777(15) 0.0568(4) Uani 1 1 d . . .
C4 C 0.6647(4) 0.84889(19) 0.72327(16) 0.0384(4) Uani 1 1 d . . .
N1 N 0.3706(5) 0.6974(2) 0.37880(19) 0.0529(5) Uani 1 1 d D . .
C1 C 0.3777(4) 0.75593(19) 0.58562(16) 0.0380(4) Uani 1 1 d . . .
C7 C 0.8297(4) 0.9032(2) 0.79100(17) 0.0415(4) Uani 1 1 d . . .
C3 C 0.4599(4) 0.9344(2) 0.6576(2) 0.0520(5) Uani 1 1 d . . .
H3 H 0.4178 1.0239 0.6595 0.062 Uiso 1 1 calc R . .
C2 C 0.3163(4) 0.8878(2) 0.5887(2) 0.0539(6) Uani 1 1 d . . .
H2 H 0.1777 0.9459 0.5442 0.065 Uiso 1 1 calc R . .
C5 C 0.7205(5) 0.7158(2) 0.7221(2) 0.0570(6) Uani 1 1 d . . .
H5 H 0.8554 0.6571 0.7684 0.068 Uiso 1 1 calc R . .
C6 C 0.5789(5) 0.6685(2) 0.6532(2) 0.0572(6) Uani 1 1 d . . .
H6 H 0.6185 0.5786 0.6524 0.069 Uiso 1 1 calc R . .
O5 O 0.3412(3) 0.88554(15) -0.03826(14) 0.0573(5) Uani 1 1 d . . .
N2 N 0.6747(3) 0.84314(17) 0.08760(15) 0.0447(4) Uani 1 1 d . . .
H2A H 0.6704 0.9272 0.0715 0.054 Uiso 1 1 calc R . .
C8 C 0.5016(4) 0.8005(2) 0.03272(17) 0.0438(5) Uani 1 1 d . . .
C12 C 0.8537(4) 0.7619(2) 0.1660(2) 0.0523(5) Uani 1 1 d . . .
H12 H 0.9673 0.7977 0.2003 0.063 Uiso 1 1 calc R . .
C9 C 0.5184(5) 0.6610(2) 0.0612(2) 0.0553(6) Uani 1 1 d . . .
H9 H 0.4063 0.6255 0.0257 0.066 Uiso 1 1 calc R . .
C11 C 0.8684(5) 0.6302(3) 0.1944(3) 0.0650(7) Uani 1 1 d . . .
H11 H 0.9894 0.5739 0.2491 0.078 Uiso 1 1 calc R . .
C10 C 0.6967(5) 0.5793(2) 0.1398(3) 0.0666(7) Uani 1 1 d . . .
H10 H 0.7055 0.4880 0.1578 0.080 Uiso 1 1 calc R . .
H1B H 0.366(5) 0.773(3) 0.344(2) 0.045(7) Uiso 1 1 d D . .
H1A H 0.480(7) 0.655(4) 0.391(3) 0.078(12) 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 O2 1.4290(15) . ?
S1 O1 1.4308(16) . ?
S1 N1 1.605(2) . ?
S1 C1 1.7725(19) . ?
O3 C7 1.210(3) . ?
O4 C7 1.314(3) . ?
O4 H4A 0.8200 . ?
C4 C3 1.373(3) . ?
C4 C5 1.377(3) . ?
C4 C7 1.497(3) . ?
N1 H1B 0.81(3) . ?
N1 H1A 0.65(4) . ?
C1 C2 1.370(3) . ?
C1 C6 1.379(3) . ?
C3 C2 1.380(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O5 C8 1.263(3) . ?
N2 C12 1.352(3) . ?
N2 C8 1.355(3) . ?
N2 H2A 0.8600 . ?
C8 C9 1.417(3) . ?
C12 C11 1.339(3) . ?
C12 H12 0.9300 . ?
C9 C10 1.352(3) . ?
C9 H9 0.9300 . ?
C11 C10 1.402(4) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?

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 120.17(10) . . ?
O2 S1 N1 106.29(12) . . ?
O1 S1 N1 106.97(12) . . ?
O2 S1 C1 108.25(9) . . ?
O1 S1 C1 106.94(9) . . ?
N1 S1 C1 107.67(10) . . ?
C7 O4 H4A 109.5 . . ?
C3 C4 C5 119.39(18) . . ?
C3 C4 C7 119.34(18) . . ?
C5 C4 C7 121.22(17) . . ?
S1 N1 H1B 111.1(17) . . ?
S1 N1 H1A 109(3) . . ?
H1B N1 H1A 120(4) . . ?
C2 C1 C6 120.31(18) . . ?
C2 C1 S1 120.73(15) . . ?
C6 C1 S1 118.92(15) . . ?
O3 C7 O4 124.44(18) . . ?
O3 C7 C4 122.83(18) . . ?
O4 C7 C4 112.71(17) . . ?
C4 C3 C2 120.17(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C1 C2 C3 120.05(19) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C5 C6 120.79(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.25(19) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C12 N2 C8 124.16(18) . . ?
C12 N2 H2A 117.9 . . ?
C8 N2 H2A 117.9 . . ?
O5 C8 N2 118.75(18) . . ?
O5 C8 C9 125.49(19) . . ?
N2 C8 C9 115.76(18) . . ?
C11 C12 N2 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
N2 C12 H12 119.8 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.08
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.082
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAHPFORMIII
_database_code_depnum_ccdc_archive 'CCDC 1414166'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; 2pyridone form III'
_chemical_name_common            'Sulfonamide benzoic acid; 2pyridone form III'
_chemical_melting_point          409
_chemical_formula_moiety         C7H7NO4S,C5H5NO

_chemical_formula_sum            'C12 H12 N2 O5 S'
_chemical_formula_weight         296.30

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)/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                   8.464(3)
_cell_length_b                   9.721(3)
_cell_length_c                   16.137(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.001(5)
_cell_angle_gamma                90.00
_cell_volume                     1307.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5511
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.32

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            13109
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         26.47
_reflns_number_total             2686
_reflns_number_gt                2223
_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)+(0.0926P)²+0.1962P] 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         2686
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.18387(6) 0.58217(5) 0.25936(3) 0.0407(2) Uani 1 1 d . . .
O3 O 0.12238(19) 0.65526(18) -0.16234(9) 0.0615(5) Uani 1 1 d . . .
O1 O 0.05040(18) 0.66155(18) 0.27475(10) 0.0595(4) Uani 1 1 d . . .
C4 C 0.2003(2) 0.58423(19) -0.01994(12) 0.0400(4) Uani 1 1 d . . .
C1 C 0.1846(2) 0.58158(18) 0.14937(12) 0.0375(4) Uani 1 1 d . . .
O5 O 0.37142(19) 0.50044(18) 0.71909(10) 0.0602(5) Uani 1 1 d . . .
O2 O 0.1994(2) 0.44225(16) 0.28715(10) 0.0534(4) Uani 1 1 d . . .
C2 C 0.0878(2) 0.6702(2) 0.09667(13) 0.0457(5) Uani 1 1 d . . .
H2 H 0.0184 0.7292 0.1181 0.055 Uiso 1 1 calc R . .
C7 C 0.2085(2) 0.5861(2) -0.11220(13) 0.0442(5) Uani 1 1 d . . .
O4 O 0.3178(2) 0.5035(2) -0.13106(11) 0.0795(7) Uani 1 1 d . . .
C6 C 0.2889(2) 0.4929(2) 0.11894(12) 0.0432(5) Uani 1 1 d . . .
H6 H 0.3527 0.4325 0.1550 0.052 Uiso 1 1 calc R . .
N1 N 0.3446(2) 0.6597(2) 0.30314(11) 0.0483(4) Uani 1 1 d . . .
N2 N 0.1520(2) 0.6235(2) 0.66115(13) 0.0567(5) Uani 1 1 d . . .
C5 C 0.2967(2) 0.4956(2) 0.03391(12) 0.0447(5) Uani 1 1 d . . .
H5 H 0.3674 0.4373 0.0128 0.054 Uiso 1 1 calc R . .
C3 C 0.0945(2) 0.6711(2) 0.01146(13) 0.0451(5) Uani 1 1 d . . .
H3 H 0.0282 0.7297 -0.0246 0.054 Uiso 1 1 calc R . .
C8 C 0.2850(3) 0.5492(2) 0.65493(13) 0.0484(5) Uani 1 1 d . . .
C9 C 0.3154(3) 0.5334(3) 0.57146(15) 0.0621(6) Uani 1 1 d . . .
H9 H 0.4058 0.4853 0.5623 0.075 Uiso 1 1 calc R . .
C10 C 0.2147(4) 0.5875(3) 0.50543(16) 0.0692(7) Uani 1 1 d . . .
H10 H 0.2368 0.5753 0.4514 0.083 Uiso 1 1 calc R . .
C11 C 0.0783(3) 0.6612(3) 0.51623(16) 0.0651(7) Uani 1 1 d . . .
H11 H 0.0088 0.6977 0.4705 0.078 Uiso 1 1 calc R . .
C12 C 0.0515(3) 0.6774(3) 0.59548(16) 0.0655(7) Uani 1 1 d . . .
H12 H -0.0379 0.7266 0.6050 0.079 Uiso 1 1 calc R . .
H1A H 0.340(3) 0.749(3) 0.2913(18) 0.075(9) Uiso 1 1 d . . .
H2A H 0.144(4) 0.638(3) 0.710(2) 0.084(10) Uiso 1 1 d . . .
H4A H 0.333(4) 0.512(3) -0.180(2) 0.086(10) Uiso 1 1 d . . .
H1B H 0.424(3) 0.608(3) 0.2969(17) 0.064(8) 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 O1 1.4251(16) . ?
S1 O2 1.4311(17) . ?
S1 N1 1.6073(19) . ?
S1 C1 1.776(2) . ?
O3 C7 1.197(2) . ?
C4 C5 1.385(3) . ?
C4 C3 1.389(3) . ?
C4 C7 1.503(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.384(3) . ?
O5 C8 1.252(3) . ?
C2 C3 1.386(3) . ?
C7 O4 1.301(3) . ?
C6 C5 1.385(3) . ?
N2 C12 1.345(3) . ?
N2 C8 1.356(3) . ?
C8 C9 1.423(3) . ?
C9 C10 1.350(4) . ?
C10 C11 1.395(4) . ?
C11 C12 1.346(4) . ?

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 O2 119.52(10) . . ?
O1 S1 N1 107.78(11) . . ?
O2 S1 N1 106.45(11) . . ?
O1 S1 C1 108.45(9) . . ?
O2 S1 C1 107.10(9) . . ?
N1 S1 C1 106.92(9) . . ?
C5 C4 C3 119.77(18) . . ?
C5 C4 C7 120.40(17) . . ?
C3 C4 C7 119.83(17) . . ?
C2 C1 C6 121.25(18) . . ?
C2 C1 S1 120.69(15) . . ?
C6 C1 S1 118.03(14) . . ?
C1 C2 C3 119.64(18) . . ?
O3 C7 O4 124.27(19) . . ?
O3 C7 C4 123.32(18) . . ?
O4 C7 C4 112.41(17) . . ?
C1 C6 C5 118.88(17) . . ?
C12 N2 C8 124.7(2) . . ?
C4 C5 C6 120.59(17) . . ?
C2 C3 C4 119.86(18) . . ?
O5 C8 N2 120.89(19) . . ?
O5 C8 C9 124.5(2) . . ?
N2 C8 C9 114.6(2) . . ?
C10 C9 C8 120.8(3) . . ?
C9 C10 C11 121.6(2) . . ?
C12 C11 C10 117.3(2) . . ?
N2 C12 C11 121.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.098
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAINA11
_database_code_depnum_ccdc_archive 'CCDC 1414167'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; isonicotina'
_chemical_name_common            'Sulfonamide benzoic acid; isonicotinamide'
_chemical_melting_point          448
_chemical_formula_moiety         C7H7NO4S,C6H6N2O

_chemical_formula_sum            'C13 H13 N3 O5 S'
_chemical_formula_weight         323.32

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           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                   31.237(4)
_cell_length_b                   5.1056(6)
_cell_length_c                   20.362(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.550(2)
_cell_angle_gamma                90.00
_cell_volume                     2674.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2840
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.29

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_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    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            13340
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         26.39
_reflns_number_total             2742
_reflns_number_gt                2209
_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)+(0.0755P)²+0.0763P] 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         2742
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.231297(19) 0.71776(10) 0.13534(3) 0.02831(18) Uani 1 1 d . . .
O4 O 0.13522(5) -0.1403(3) -0.16182(8) 0.0309(3) Uani 1 1 d . . .
O5 O 0.07564(5) -0.2015(3) -0.13618(9) 0.0360(4) Uani 1 1 d . . .
C4 C 0.13933(7) 0.1313(4) -0.06462(11) 0.0261(4) Uani 1 1 d . . .
C7 C 0.11355(7) -0.0844(4) -0.12423(11) 0.0263(4) Uani 1 1 d . . .
O2 O 0.20421(6) 0.7618(3) 0.17171(9) 0.0446(4) Uani 1 1 d . . .
C2 C 0.20445(7) 0.4661(4) -0.00076(11) 0.0301(5) Uani 1 1 d . . .
H2 H 0.2303 0.5666 0.0021 0.036 Uiso 1 1 calc R . .
C3 C 0.17801(8) 0.2813(4) -0.05983(12) 0.0288(4) Uani 1 1 d . . .
H3 H 0.1861 0.2568 -0.0968 0.035 Uiso 1 1 calc R . .
O1 O 0.24577(6) 0.9314(3) 0.10689(8) 0.0401(4) Uani 1 1 d . . .
C1 C 0.19237(7) 0.5016(4) 0.05456(11) 0.0269(4) Uani 1 1 d . . .
C5 C 0.12612(8) 0.1769(4) -0.01111(12) 0.0332(5) Uani 1 1 d . . .
H5 H 0.0991 0.0828 -0.0157 0.040 Uiso 1 1 calc R . .
N1 N 0.28415(7) 0.5720(4) 0.20000(11) 0.0376(5) Uani 1 1 d . . .
C6 C 0.15268(8) 0.3604(4) 0.04892(12) 0.0331(5) Uani 1 1 d . . .
H6 H 0.1439 0.3885 0.0851 0.040 Uiso 1 1 calc R . .
N2 N 0.09443(6) 0.5395(3) 0.24272(9) 0.0296(4) Uani 1 1 d . . .
O3 O 0.04744(6) 1.2447(3) 0.04493(9) 0.0366(4) Uani 1 1 d . . .
N3 N -0.01520(7) 1.3030(4) 0.06537(11) 0.0316(4) Uani 1 1 d . . .
C8 C 0.04864(7) 0.9565(4) 0.13688(11) 0.0258(4) Uani 1 1 d . . .
C13 C 0.02628(7) 1.1808(4) 0.07818(11) 0.0257(4) Uani 1 1 d . . .
C9 C 0.09232(8) 0.8322(4) 0.15029(12) 0.0305(5) Uani 1 1 d . . .
H9 H 0.1070 0.8876 0.1237 0.037 Uiso 1 1 calc R . .
C11 C 0.05275(8) 0.6610(4) 0.23063(12) 0.0323(5) Uani 1 1 d . . .
H11 H 0.0392 0.6033 0.2586 0.039 Uiso 1 1 calc R . .
C12 C 0.02886(8) 0.8676(4) 0.17876(12) 0.0319(5) Uani 1 1 d . . .
H12 H -0.0002 0.9465 0.1719 0.038 Uiso 1 1 calc R . .
C10 C 0.11392(8) 0.6270(4) 0.20301(12) 0.0314(5) Uani 1 1 d . . .
H10 H 0.1433 0.5457 0.2114 0.038 Uiso 1 1 calc R . .
H3A H -0.0313(10) 1.264(5) 0.0892(15) 0.047(7) Uiso 1 1 d . . .
H3B H -0.0274(8) 1.425(5) 0.0310(13) 0.036(6) Uiso 1 1 d . . .
H1A H 0.3036(10) 0.543(5) 0.1841(16) 0.057(8) Uiso 1 1 d . . .
H1B H 0.2813(9) 0.457(6) 0.2280(15) 0.051(7) Uiso 1 1 d . . .
H4A H 0.1176(12) -0.300(7) -0.2007(19) 0.086(10) 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 1.4233(15) . ?
S1 O1 1.4237(15) . ?
S1 N1 1.596(2) . ?
S1 C1 1.770(2) . ?
O4 C7 1.309(2) . ?
O5 C7 1.221(2) . ?
C4 C5 1.386(3) . ?
C4 C3 1.386(3) . ?
C4 C7 1.492(3) . ?
C2 C3 1.376(3) . ?
C2 C1 1.388(3) . ?
C1 C6 1.382(3) . ?
C5 C6 1.382(3) . ?
N2 C11 1.333(2) . ?
N2 C10 1.335(2) . ?
O3 C13 1.228(2) . ?
N3 C13 1.324(3) . ?
C8 C12 1.383(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.510(3) . ?
C9 C10 1.373(3) . ?
C11 C12 1.375(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
O2 S1 O1 120.70(10) . . ?
O2 S1 N1 106.64(11) . . ?
O1 S1 N1 105.91(10) . . ?
O2 S1 C1 106.51(9) . . ?
O1 S1 C1 108.00(9) . . ?
N1 S1 C1 108.66(10) . . ?
C5 C4 C3 119.22(18) . . ?
C5 C4 C7 119.95(17) . . ?
C3 C4 C7 120.78(17) . . ?
O5 C7 O4 122.78(18) . . ?
O5 C7 C4 122.57(17) . . ?
O4 C7 C4 114.65(16) . . ?
C3 C2 C1 119.64(18) . . ?
C2 C3 C4 120.49(18) . . ?
C6 C1 C2 120.58(18) . . ?
C6 C1 S1 120.90(14) . . ?
C2 C1 S1 118.42(15) . . ?
C6 C5 C4 120.79(18) . . ?
C1 C6 C5 119.17(18) . . ?
C11 N2 C10 117.75(17) . . ?
C12 C8 C9 117.57(18) . . ?
C12 C8 C13 124.70(17) . . ?
C9 C8 C13 117.73(17) . . ?
O3 C13 N3 122.60(18) . . ?
O3 C13 C8 119.05(17) . . ?
N3 C13 C8 118.35(17) . . ?
C10 C9 C8 119.77(18) . . ?
N2 C11 C12 123.13(18) . . ?
C11 C12 C8 119.21(18) . . ?
N2 C10 C9 122.57(18) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.067
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAINAHP111
_database_code_depnum_ccdc_archive 'CCDC 1414168'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Sulfonamide benzoic acid; isonicotinamide; 2pyridone'
_chemical_name_common            
'Sulfonamide benzoic acid; isonicotinamide; 2pyridone'
_chemical_melting_point          418
_chemical_formula_moiety         C7H7NO4S,C6H6N2O,C5H5NO
_chemical_formula_sum            'C18 H18 N4 O6 S'
_chemical_formula_weight         418.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   20.4140(14)
_cell_length_b                   6.5885(4)
_cell_length_c                   14.7470(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.671(6)
_cell_angle_gamma                90.00
_cell_volume                     1942.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3550
_cell_measurement_theta_min      4.3780
_cell_measurement_theta_max      71.5760

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71451
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10420
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         67.06
_reflns_number_total             3464
_reflns_number_gt                2690
_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)+(0.1285P)²+0.1029P] 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         3464
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.2053
_refine_ls_wR_factor_gt          0.1833
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.71773(4) 0.80437(11) 0.70029(5) 0.0610(3) Uani 1 1 d . . .
O6 O 0.57578(10) 0.9572(3) 0.46055(16) 0.0688(6) Uani 1 1 d . . .
O5 O 0.69327(11) 0.1148(3) 1.00386(15) 0.0686(6) Uani 1 1 d . . .
O1 O 0.68134(12) 0.9592(4) 0.73580(17) 0.0825(7) Uani 1 1 d . . .
O4 O 0.97350(12) 1.3554(4) 0.61795(19) 0.0770(7) Uani 1 1 d . . .
N1 N 0.67542(16) 0.7431(5) 0.6013(2) 0.0687(7) Uani 1 1 d . . .
O2 O 0.73379(14) 0.6213(4) 0.75102(18) 0.0895(8) Uani 1 1 d . . .
N4 N 0.47944(13) 0.7771(4) 0.42823(18) 0.0605(6) Uani 1 1 d . . .
C1 C 0.79417(14) 0.9100(4) 0.68368(17) 0.0514(6) Uani 1 1 d . . .
N2 N 0.90949(13) -0.0131(4) 0.90734(17) 0.0657(7) Uani 1 1 d . . .
O3 O 1.02393(14) 1.0594(4) 0.6339(3) 0.1092(11) Uani 1 1 d . . .
N3 N 0.69122(15) 0.3602(5) 0.8993(2) 0.0716(8) Uani 1 1 d . . .
C2 C 0.84988(16) 0.7897(4) 0.6893(2) 0.0615(7) Uani 1 1 d . . .
H2 H 0.8482 0.6534 0.7050 0.074 Uiso 1 1 calc R . .
C15 C 0.57096(16) 0.6617(5) 0.3681(2) 0.0625(7) Uani 1 1 d . . .
H15 H 0.6149 0.6746 0.3605 0.075 Uiso 1 1 calc R . .
C14 C 0.54419(14) 0.8063(4) 0.42067(19) 0.0543(7) Uani 1 1 d . . .
C6 C 0.79594(15) 1.1145(4) 0.6621(2) 0.0591(7) Uani 1 1 d . . .
H6 H 0.7583 1.1956 0.6589 0.071 Uiso 1 1 calc R . .
C12 C 0.82916(16) 0.2533(5) 0.8964(2) 0.0628(7) Uani 1 1 d . . .
H12 H 0.8177 0.3873 0.8808 0.075 Uiso 1 1 calc R . .
C4 C 0.91091(15) 1.0744(4) 0.64954(18) 0.0552(6) Uani 1 1 d . . .
C5 C 0.85461(16) 1.1953(4) 0.6454(2) 0.0595(7) Uani 1 1 d . . .
H5 H 0.8566 1.3324 0.6312 0.071 Uiso 1 1 calc R . .
C3 C 0.90820(16) 0.8711(5) 0.6717(2) 0.0623(7) Uani 1 1 d . . .
H3 H 0.9457 0.7894 0.6747 0.075 Uiso 1 1 calc R . .
C13 C 0.71828(15) 0.2002(4) 0.94547(19) 0.0554(7) Uani 1 1 d . . .
C11 C 0.89106(17) 0.1780(5) 0.8883(2) 0.0675(8) Uani 1 1 d . . .
H11 H 0.9211 0.2653 0.8686 0.081 Uiso 1 1 calc R . .
C7 C 0.97561(16) 1.1609(5) 0.6324(2) 0.0635(7) Uani 1 1 d . . .
C8 C 0.78499(14) 0.1272(4) 0.92793(17) 0.0539(6) Uani 1 1 d . . .
C9 C 0.80404(16) -0.0717(4) 0.9483(2) 0.0618(7) Uani 1 1 d . . .
H9 H 0.7753 -0.1616 0.9693 0.074 Uiso 1 1 calc R . .
C16 C 0.53322(19) 0.5038(5) 0.3285(2) 0.0759(9) Uani 1 1 d . . .
H16 H 0.5515 0.4093 0.2939 0.091 Uiso 1 1 calc R . .
C17 C 0.4673(2) 0.4815(6) 0.3390(3) 0.0870(11) Uani 1 1 d . . .
H17 H 0.4414 0.3731 0.3118 0.104 Uiso 1 1 calc R . .
C10 C 0.86626(17) -0.1348(5) 0.9368(2) 0.0686(8) Uani 1 1 d . . .
H10 H 0.8786 -0.2690 0.9504 0.082 Uiso 1 1 calc R . .
C18 C 0.44186(19) 0.6197(5) 0.3893(3) 0.0805(10) Uani 1 1 d . . .
H18 H 0.3980 0.6066 0.3974 0.097 Uiso 1 1 calc R . .
H1B H 0.689(2) 0.645(7) 0.578(3) 0.093(14) Uiso 1 1 d . . .
H1A H 0.6519(19) 0.845(6) 0.570(3) 0.083(12) Uiso 1 1 d . . .
H4B H 0.4637(18) 0.867(6) 0.465(3) 0.085(11) Uiso 1 1 d . . .
H4A H 1.012(2) 1.404(6) 0.610(3) 0.094(13) Uiso 1 1 d . . .
H3A H 0.7090(18) 0.407(6) 0.857(3) 0.077(11) Uiso 1 1 d . . .
H3B H 0.655(2) 0.416(5) 0.913(3) 0.083(11) 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 1.422(3) . ?
S1 O1 1.423(2) . ?
S1 N1 1.591(3) . ?
S1 C1 1.770(3) . ?
O6 C14 1.264(3) . ?
O5 C13 1.223(3) . ?
O4 C7 1.298(4) . ?
N4 C18 1.347(4) . ?
N4 C14 1.362(4) . ?
C1 C2 1.375(4) . ?
C1 C6 1.387(4) . ?
N2 C11 1.328(4) . ?
N2 C10 1.329(4) . ?
O3 C7 1.188(4) . ?
N3 C13 1.314(4) . ?
C2 C3 1.377(4) . ?
C15 C16 1.354(5) . ?
C15 C14 1.407(4) . ?
C6 C5 1.377(4) . ?
C12 C8 1.375(4) . ?
C12 C11 1.385(4) . ?
C4 C3 1.383(4) . ?
C4 C5 1.389(4) . ?
C4 C7 1.506(4) . ?
C13 C8 1.515(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.379(4) . ?
C16 C17 1.394(5) . ?
C17 C18 1.343(5) . ?

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 119.76(17) . . ?
O2 S1 N1 106.98(18) . . ?
O1 S1 N1 107.03(17) . . ?
O2 S1 C1 106.89(15) . . ?
O1 S1 C1 108.02(14) . . ?
N1 S1 C1 107.64(14) . . ?
C18 N4 C14 123.5(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 S1 120.4(2) . . ?
C6 C1 S1 118.6(2) . . ?
C11 N2 C10 117.6(3) . . ?
C1 C2 C3 120.0(3) . . ?
C16 C15 C14 120.5(3) . . ?
O6 C14 N4 119.0(2) . . ?
O6 C14 C15 124.8(3) . . ?
N4 C14 C15 116.2(3) . . ?
C5 C6 C1 118.7(3) . . ?
C8 C12 C11 119.0(3) . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 C7 119.0(3) . . ?
C5 C4 C7 121.4(3) . . ?
C6 C5 C4 120.8(3) . . ?
C2 C3 C4 119.9(3) . . ?
O5 C13 N3 122.8(3) . . ?
O5 C13 C8 119.4(3) . . ?
N3 C13 C8 117.7(2) . . ?
N2 C11 C12 123.1(3) . . ?
O3 C7 O4 123.9(3) . . ?
O3 C7 C4 122.5(3) . . ?
O4 C7 C4 113.6(3) . . ?
C12 C8 C9 118.1(3) . . ?
C12 C8 C13 122.6(3) . . ?
C9 C8 C13 119.2(3) . . ?
C10 C9 C8 119.0(3) . . ?
C15 C16 C17 120.7(3) . . ?
C18 C17 C16 118.7(3) . . ?
N2 C10 C9 123.2(3) . . ?
C17 C18 N4 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.06
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.062
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAMEHP12
_database_code_depnum_ccdc_archive 'CCDC 1414169'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; 6methyl 2pyridone'
_chemical_name_common            'Sulfonamide benzoic acid; 6methyl 2pyridone'
_chemical_melting_point          434
_chemical_formula_moiety         C7H7NO4S,2(C6H7NO)
_chemical_formula_sum            'C19 H21 N3 O6 S'
_chemical_formula_weight         419.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.3848(8)
_cell_length_b                   31.150(3)
_cell_length_c                   8.9746(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.676(2)
_cell_angle_gamma                90.00
_cell_volume                     2064.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5576
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.95

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            21034
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.94
_reflns_number_total             4005
_reflns_number_gt                3282
_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)+(0.0745P)²+0.2442P] 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         4005
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.39302(7) 0.279279(13) 1.09804(5) 0.05246(16) Uani 1 1 d . . .
O3 O 0.0998(2) 0.45978(4) 0.76171(16) 0.0807(5) Uani 1 1 d . . .
N2 N 0.8928(2) 0.37221(4) 0.19762(17) 0.0517(4) Uani 1 1 d . . .
O6 O 0.77118(18) 0.33552(4) 0.93160(14) 0.0623(3) Uani 1 1 d . . .
O4 O 0.2324(2) 0.48564(4) 0.96478(16) 0.0742(4) Uani 1 1 d . . .
O1 O 0.4631(2) 0.28616(4) 1.24539(14) 0.0738(4) Uani 1 1 d . . .
O5 O 0.82506(19) 0.43510(4) 0.08657(14) 0.0658(4) Uani 1 1 d . . .
C1 C 0.3269(2) 0.33074(5) 1.03448(17) 0.0457(4) Uani 1 1 d . . .
O2 O 0.2483(2) 0.24970(4) 1.07651(17) 0.0745(4) Uani 1 1 d . . .
N1 N 0.5566(2) 0.26342(5) 0.99819(17) 0.0519(4) Uani 1 1 d . . .
N3 N 0.7001(2) 0.39706(5) 0.81005(18) 0.0558(4) Uani 1 1 d . . .
C4 C 0.2342(2) 0.41126(5) 0.93333(17) 0.0462(4) Uani 1 1 d . . .
C8 C 0.8940(2) 0.41608(5) 0.19756(19) 0.0526(4) Uani 1 1 d . . .
C2 C 0.3805(3) 0.36644(6) 1.11411(18) 0.0552(4) Uani 1 1 d . . .
H2 H 0.4479 0.3634 1.2016 0.066 Uiso 1 1 calc R . .
C7 C 0.1812(3) 0.45449(5) 0.87655(19) 0.0537(4) Uani 1 1 d . . .
C5 C 0.1818(2) 0.37523(5) 0.85444(19) 0.0526(4) Uani 1 1 d . . .
H5 H 0.1146 0.3783 0.7668 0.063 Uiso 1 1 calc R . .
C3 C 0.3338(3) 0.40663(5) 1.06366(19) 0.0550(4) Uani 1 1 d . . .
H3 H 0.3693 0.4308 1.1174 0.066 Uiso 1 1 calc R . .
C12 C 0.9637(2) 0.34693(6) 0.30719(19) 0.0551(4) Uani 1 1 d . . .
C13 C 0.9419(3) 0.29993(6) 0.2899(2) 0.0696(5) Uani 1 1 d . . .
H13A H 1.0230 0.2854 0.3574 0.104 Uiso 1 1 calc R . .
H13B H 0.9691 0.2919 0.1894 0.104 Uiso 1 1 calc R . .
H13C H 0.8193 0.2920 0.3117 0.104 Uiso 1 1 calc R . .
C6 C 0.2277(2) 0.33467(5) 0.90374(18) 0.0528(4) Uani 1 1 d . . .
H6 H 0.1926 0.3105 0.8500 0.063 Uiso 1 1 calc R . .
C14 C 0.7105(2) 0.35338(6) 0.8158(2) 0.0538(4) Uani 1 1 d . . .
C10 C 1.0479(3) 0.41119(7) 0.4327(2) 0.0753(6) Uani 1 1 d . . .
H10 H 1.1024 0.4245 0.5144 0.090 Uiso 1 1 calc R . .
C15 C 0.6472(3) 0.33165(7) 0.6869(2) 0.0672(5) Uani 1 1 d . . .
H15 H 0.6533 0.3019 0.6825 0.081 Uiso 1 1 calc R . .
C9 C 0.9744(3) 0.43564(6) 0.3228(2) 0.0647(5) Uani 1 1 d . . .
H9 H 0.9771 0.4654 0.3303 0.078 Uiso 1 1 calc R . .
C17 C 0.5698(3) 0.39834(7) 0.5725(2) 0.0738(6) Uani 1 1 d . . .
H17 H 0.5209 0.4131 0.4914 0.089 Uiso 1 1 calc R . .
C11 C 1.0437(3) 0.36651(7) 0.4256(2) 0.0691(5) Uani 1 1 d . . .
H11 H 1.0955 0.3502 0.5018 0.083 Uiso 1 1 calc R . .
C18 C 0.6331(3) 0.42017(6) 0.6934(2) 0.0611(5) Uani 1 1 d . . .
C16 C 0.5785(3) 0.35372(7) 0.5709(2) 0.0760(6) Uani 1 1 d . . .
H16 H 0.5359 0.3389 0.4877 0.091 Uiso 1 1 calc R . .
C19 C 0.6359(4) 0.46764(7) 0.7093(3) 0.0832(7) Uani 1 1 d . . .
H19A H 0.5667 0.4804 0.6296 0.125 Uiso 1 1 calc R . .
H19B H 0.7586 0.4777 0.7055 0.125 Uiso 1 1 calc R . .
H19C H 0.5842 0.4755 0.8031 0.125 Uiso 1 1 calc R . .
H1A H 0.523(3) 0.2519(6) 0.923(2) 0.052(5) Uiso 1 1 d . . .
H1B H 0.636(3) 0.2838(8) 0.981(2) 0.076(7) Uiso 1 1 d . . .
H3A H 0.738(2) 0.4097(6) 0.8874(19) 0.048(5) Uiso 1 1 d . . .
H2A H 0.847(3) 0.3607(6) 0.119(2) 0.057(5) Uiso 1 1 d . . .
H4A H 0.201(4) 0.5137(10) 0.932(3) 0.109(9) 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 1.4224(15) . ?
S1 O1 1.4307(14) . ?
S1 N1 1.5909(17) . ?
S1 C1 1.7681(16) . ?
O3 C7 1.198(2) . ?
N2 C12 1.360(2) . ?
N2 C8 1.367(2) . ?
O6 C14 1.257(2) . ?
O4 C7 1.306(2) . ?
O5 C8 1.261(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.381(2) . ?
N3 C18 1.359(2) . ?
N3 C14 1.364(2) . ?
C4 C5 1.380(2) . ?
C4 C3 1.382(2) . ?
C4 C7 1.490(2) . ?
C8 C9 1.404(2) . ?
C2 C3 1.374(2) . ?
C5 C6 1.380(2) . ?
C12 C11 1.355(3) . ?
C12 C13 1.481(3) . ?
C14 C15 1.415(2) . ?
C10 C9 1.355(3) . ?
C10 C11 1.394(3) . ?
C15 C16 1.342(3) . ?
C17 C18 1.359(3) . ?
C17 C16 1.391(3) . ?
C18 C19 1.486(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
O2 S1 O1 119.07(9) . . ?
O2 S1 N1 107.24(9) . . ?
O1 S1 N1 107.35(9) . . ?
O2 S1 C1 109.84(8) . . ?
O1 S1 C1 104.94(7) . . ?
N1 S1 C1 107.95(8) . . ?
C12 N2 C8 125.23(16) . . ?
C2 C1 C6 121.01(15) . . ?
C2 C1 S1 119.22(13) . . ?
C6 C1 S1 119.74(12) . . ?
C18 N3 C14 125.27(16) . . ?
C5 C4 C3 119.50(15) . . ?
C5 C4 C7 119.24(14) . . ?
C3 C4 C7 121.26(14) . . ?
O5 C8 N2 117.87(15) . . ?
O5 C8 C9 126.25(17) . . ?
N2 C8 C9 115.87(16) . . ?
C3 C2 C1 119.69(15) . . ?
O3 C7 O4 123.93(16) . . ?
O3 C7 C4 123.05(15) . . ?
O4 C7 C4 113.02(15) . . ?
C6 C5 C4 120.92(15) . . ?
C2 C3 C4 120.22(15) . . ?
C11 C12 N2 117.87(17) . . ?
C11 C12 C13 124.97(17) . . ?
N2 C12 C13 117.13(16) . . ?
C5 C6 C1 118.66(15) . . ?
O6 C14 N3 119.48(16) . . ?
O6 C14 C15 125.14(17) . . ?
N3 C14 C15 115.38(17) . . ?
C9 C10 C11 121.32(18) . . ?
C16 C15 C14 120.48(19) . . ?
C10 C9 C8 120.07(18) . . ?
C18 C17 C16 119.51(19) . . ?
C12 C11 C10 119.63(18) . . ?
N3 C18 C17 117.95(19) . . ?
N3 C18 C19 116.67(17) . . ?
C17 C18 C19 125.38(19) . . ?
C15 C16 C17 121.39(19) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.94
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.085
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAC, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBANAM12
_database_code_depnum_ccdc_archive 'CCDC 1414170'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; nicotinamide'
_chemical_name_common            'Sulfonamide benzoic acid; nicotinamide'
_chemical_melting_point          403
_chemical_formula_moiety         'C7H7NO4S,2(C6H6 N2O)'

_chemical_formula_sum            'C19 H18 N5 O6 S'
_chemical_formula_weight         444.44

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                   5.0179(5)
_cell_length_b                   11.3168(17)
_cell_length_c                   18.156(2)
_cell_angle_alpha                95.966(12)
_cell_angle_beta                 90.050(9)
_cell_angle_gamma                95.469(10)
_cell_volume                     1020.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1536
_cell_measurement_theta_min      4.2240
_cell_measurement_theta_max      26.8140

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_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    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7085
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4153
_reflns_number_gt                2562
_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)+(0.0533P)²+0.0885P] 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         4153
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.34677(16) 0.35347(9) 1.09212(5) 0.0568(3) Uani 1 1 d . . .
O5 O -0.3834(4) 0.87336(17) 0.53790(11) 0.0442(5) Uani 1 1 d . . .
O1 O -0.3293(4) 0.1006(2) 0.79023(12) 0.0554(6) Uani 1 1 d . . .
N3 N -0.2406(5) 1.0644(2) 0.57098(16) 0.0431(6) Uani 1 1 d . . .
N2 N 0.3397(4) 0.9495(2) 0.70997(13) 0.0427(6) Uani 1 1 d . . .
O2 O -0.1782(5) -0.0592(2) 0.82906(13) 0.0658(7) Uani 1 1 d . . .
C19 C -0.2326(5) 0.9488(2) 0.57536(15) 0.0339(6) Uani 1 1 d . . .
C15 C 0.1627(5) 0.9861(3) 0.66478(15) 0.0388(7) Uani 1 1 d . . .
H15 H 0.1715 1.0669 0.6586 0.047 Uiso 1 1 calc R . .
C14 C -0.0334(5) 0.9096(2) 0.62665(14) 0.0330(6) Uani 1 1 d . . .
N1 N 0.1545(5) 0.3147(3) 1.15748(14) 0.0508(7) Uani 1 1 d . . .
H1A H -0.003(6) 0.332(3) 1.1524(17) 0.061 Uiso 1 1 d . . .
H1B H 0.175(6) 0.234(3) 1.1627(18) 0.061 Uiso 1 1 d . . .
C18 C -0.0429(5) 0.7900(3) 0.63662(16) 0.0408(7) Uani 1 1 d . . .
H18 H -0.1728 0.7358 0.6121 0.049 Uiso 1 1 calc R . .
C1 C 0.2188(6) 0.2696(3) 1.00998(16) 0.0478(8) Uani 1 1 d . . .
C7 C -0.1861(6) 0.0472(3) 0.83388(16) 0.0438(7) Uani 1 1 d . . .
C16 C 0.3267(6) 0.8334(3) 0.71883(16) 0.0451(7) Uani 1 1 d . . .
H16 H 0.4489 0.8075 0.7506 0.054 Uiso 1 1 calc R . .
C4 C -0.0335(5) 0.1287(3) 0.89251(15) 0.0412(7) Uani 1 1 d . . .
C17 C 0.1399(6) 0.7512(3) 0.68277(17) 0.0461(7) Uani 1 1 d . . .
H17 H 0.1370 0.6707 0.6894 0.055 Uiso 1 1 calc R . .
C5 C -0.0921(6) 0.2451(3) 0.90912(16) 0.0487(8) Uani 1 1 d . . .
H5 H -0.2164 0.2763 0.8804 0.058 Uiso 1 1 calc R . .
O4 O 0.5996(4) 0.3142(3) 1.10828(14) 0.0858(9) Uani 1 1 d . . .
C3 C 0.1586(6) 0.0849(3) 0.93380(17) 0.0547(9) Uani 1 1 d . . .
H3 H 0.2026 0.0072 0.9218 0.066 Uiso 1 1 calc R . .
C6 C 0.0332(6) 0.3154(3) 0.96814(17) 0.0536(8) Uani 1 1 d . . .
H6 H -0.0080 0.3935 0.9796 0.064 Uiso 1 1 calc R . .
C2 C 0.2857(6) 0.1545(3) 0.99249(18) 0.0587(9) Uani 1 1 d . . .
H2 H 0.4152 0.1245 1.0201 0.070 Uiso 1 1 calc R . .
O6 O 0.1436(4) 0.47347(18) 0.41162(12) 0.0560(6) Uani 1 1 d . . .
N4 N 0.9084(5) 0.7235(2) 0.34940(14) 0.0467(6) Uani 1 1 d . . .
C8 C 0.5131(5) 0.5989(2) 0.37731(15) 0.0371(7) Uani 1 1 d . . .
N5 N 0.2944(5) 0.6232(2) 0.49642(14) 0.0483(7) Uani 1 1 d . . .
H5A H 0.1744 0.6026 0.5276 0.058 Uiso 1 1 calc R . .
H5B H 0.4085 0.6839 0.5080 0.058 Uiso 1 1 calc R . .
C13 C 0.3035(5) 0.5608(2) 0.43004(16) 0.0403(7) Uani 1 1 d . . .
C9 C 0.7229(5) 0.6858(2) 0.39616(16) 0.0414(7) Uani 1 1 d . . .
H9 H 0.7348 0.7202 0.4450 0.050 Uiso 1 1 calc R . .
C10 C 0.8899(6) 0.6729(3) 0.28048(18) 0.0528(8) Uani 1 1 d . . .
H10 H 1.0172 0.6978 0.2467 0.063 Uiso 1 1 calc R . .
C12 C 0.4983(6) 0.5469(3) 0.30453(18) 0.0521(8) Uani 1 1 d . . .
C11 C 0.6923(7) 0.5857(3) 0.25642(19) 0.0635(10) Uani 1 1 d . . .
H11 H 0.6887 0.5524 0.2074 0.076 Uiso 1 1 calc R . .
H1C H -0.463(8) 0.036(4) 0.754(2) 0.106(14) Uiso 1 1 d . . .
O3 O 0.3238(6) 0.4766(2) 1.08625(14) 0.0861(8) Uani 1 1 d . . .
H3A H -0.155(5) 1.116(3) 0.6003(15) 0.037(8) Uiso 1 1 d . . .
H3B H -0.373(7) 1.082(3) 0.539(2) 0.077(11) 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 O4 1.424(2) . ?
S1 O3 1.424(3) . ?
S1 N1 1.600(3) . ?
S1 C1 1.768(3) . ?
O5 C19 1.233(3) . ?
O1 C7 1.300(3) . ?
N3 C19 1.323(4) . ?
N2 C15 1.332(3) . ?
N2 C16 1.335(4) . ?
O2 C7 1.203(4) . ?
C19 C14 1.494(4) . ?
C15 C14 1.381(4) . ?
C14 C18 1.380(4) . ?
C18 C17 1.374(4) . ?
C1 C6 1.373(4) . ?
C1 C2 1.381(4) . ?
C7 C4 1.493(4) . ?
C16 C17 1.371(4) . ?
C4 C3 1.380(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.379(4) . ?
C3 C2 1.376(4) . ?
O6 C13 1.230(3) . ?
N4 C10 1.320(4) . ?
N4 C9 1.330(3) . ?
C8 C9 1.387(4) . ?
C8 C12 1.389(4) . ?
C8 C13 1.487(4) . ?
N5 C13 1.335(3) . ?
C10 C11 1.368(4) . ?
C12 C11 1.380(4) . ?

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 O3 120.14(18) . . ?
O4 S1 N1 105.30(16) . . ?
O3 S1 N1 107.37(16) . . ?
O4 S1 C1 108.06(15) . . ?
O3 S1 C1 108.75(16) . . ?
N1 S1 C1 106.41(15) . . ?
C15 N2 C16 118.4(3) . . ?
O5 C19 N3 121.6(3) . . ?
O5 C19 C14 119.6(2) . . ?
N3 C19 C14 118.8(2) . . ?
N2 C15 C14 123.1(3) . . ?
C15 C14 C18 117.5(3) . . ?
C15 C14 C19 123.9(2) . . ?
C18 C14 C19 118.6(2) . . ?
C17 C18 C14 119.9(3) . . ?
C6 C1 C2 120.5(3) . . ?
C6 C1 S1 119.4(3) . . ?
C2 C1 S1 119.8(2) . . ?
O2 C7 O1 123.6(3) . . ?
O2 C7 C4 121.8(3) . . ?
O1 C7 C4 114.6(3) . . ?
N2 C16 C17 122.4(3) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 C7 119.4(3) . . ?
C5 C4 C7 121.1(3) . . ?
C16 C17 C18 118.7(3) . . ?
C6 C5 C4 120.2(3) . . ?
C2 C3 C4 120.8(3) . . ?
C1 C6 C5 119.8(3) . . ?
C3 C2 C1 119.2(3) . . ?
C10 N4 C9 116.8(3) . . ?
C9 C8 C12 117.4(3) . . ?
C9 C8 C13 123.7(3) . . ?
C12 C8 C13 118.9(3) . . ?
O6 C13 N5 121.8(3) . . ?
O6 C13 C8 119.6(3) . . ?
N5 C13 C8 118.7(3) . . ?
N4 C9 C8 124.7(3) . . ?
N4 C10 C11 123.1(3) . . ?
C11 C12 C8 117.6(3) . . ?
C10 C11 C12 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBANAMHP111
_database_code_depnum_ccdc_archive 'CCDC 1414171'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Sulfonamide benzoic acid; nicotinamide; 2pyridone'
_chemical_name_common            
'Sulfonamide benzoic acid; nicotinamide; 2pyridone'
_chemical_melting_point          413
_chemical_formula_moiety         C7H7NO4S,C6H6N2O,C5H5NO
_chemical_formula_sum            'C18 H18 N4 O6 S'
_chemical_formula_weight         418.42

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'

_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                   19.7594(7)
_cell_length_b                   5.25798(10)
_cell_length_c                   20.2747(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.924(4)
_cell_angle_gamma                90.00
_cell_volume                     1861.18(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5510
_cell_measurement_theta_min      4.3100
_cell_measurement_theta_max      71.6440

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11494
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.94
_diffrn_reflns_theta_max         67.07
_reflns_number_total             3327
_reflns_number_gt                2966
_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)+(0.0661P)²+0.7522P] 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         3327
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C2 C 0.96512(12) 0.4163(4) 0.09383(12) 0.0490(5) Uani 1 1 d . . .
H2 H 0.9779 0.5253 0.0653 0.059 Uiso 1 1 calc R . .
C5 C 0.92598(12) 0.0855(4) 0.17678(12) 0.0475(5) Uani 1 1 d . . .
H5 H 0.9122 -0.0282 0.2036 0.057 Uiso 1 1 calc R . .
C3 C 0.89995(11) 0.4581(4) 0.10123(12) 0.0472(5) Uani 1 1 d . . .
H3 H 0.8689 0.5973 0.0778 0.057 Uiso 1 1 calc R . .
C6 C 0.99179(12) 0.0444(4) 0.17066(12) 0.0466(5) Uani 1 1 d . . .
H6 H 1.0230 -0.0943 0.1942 0.056 Uiso 1 1 calc R . .
C1 C 1.01084(11) 0.2107(4) 0.12941(11) 0.0405(4) Uani 1 1 d . . .
C4 C 0.88038(11) 0.2948(4) 0.14326(10) 0.0401(4) Uani 1 1 d . . .
S1 S 1.09788(3) 0.16577(10) 0.12535(3) 0.04658(18) Uani 1 1 d . . .
O5 O 0.45914(8) 1.1634(3) 0.14178(8) 0.0459(3) Uani 1 1 d . . .
O6 O 0.40197(9) 0.6915(3) 0.01142(9) 0.0526(4) Uani 1 1 d . . .
N2 N 0.34773(9) 0.5540(3) 0.08128(9) 0.0428(4) Uani 1 1 d . . .
H2A H 0.3812 0.4341 0.0985 0.051 Uiso 1 1 calc R . .
N3 N 0.66929(9) 0.6641(3) 0.16372(10) 0.0451(4) Uani 1 1 d . . .
N4 N 0.50751(9) 1.2568(3) 0.06434(9) 0.0445(4) Uani 1 1 d . . .
H4A H 0.4755 1.3793 0.0441 0.053 Uiso 1 1 calc R . .
H4B H 0.5407 1.2224 0.0494 0.053 Uiso 1 1 calc R . .
O4 O 0.78068(9) 0.5647(3) 0.13104(11) 0.0632(5) Uani 1 1 d . . .
H4C H 0.7430 0.5800 0.1376 0.095 Uiso 1 1 calc R . .
O3 O 0.78712(9) 0.1826(3) 0.18119(10) 0.0627(4) Uani 1 1 d . . .
C13 C 0.50566(10) 1.1215(4) 0.11840(10) 0.0361(4) Uani 1 1 d . . .
C12 C 0.61885(11) 0.8531(4) 0.13253(11) 0.0419(4) Uani 1 1 d . . .
H12 H 0.6216 0.9502 0.0955 0.050 Uiso 1 1 calc R . .
C11 C 0.66573(11) 0.5272(4) 0.21757(11) 0.0456(5) Uani 1 1 d . . .
H11 H 0.7006 0.3955 0.2394 0.055 Uiso 1 1 calc R . .
C8 C 0.56290(10) 0.9103(4) 0.15291(10) 0.0359(4) Uani 1 1 d . . .
O2 O 1.08606(11) 0.2343(4) 0.05319(10) 0.0730(5) Uani 1 1 d . . .
C15 C 0.29747(12) 0.9239(4) 0.00898(12) 0.0473(5) Uani 1 1 d . . .
H15 H 0.2986 1.0493 -0.0228 0.057 Uiso 1 1 calc R . .
C9 C 0.56050(11) 0.7666(4) 0.20905(11) 0.0422(4) Uani 1 1 d . . .
H9 H 0.5239 0.8005 0.2245 0.051 Uiso 1 1 calc R . .
C14 C 0.35225(10) 0.7224(4) 0.03217(10) 0.0398(4) Uani 1 1 d . . .
C7 C 0.81112(11) 0.3406(4) 0.15386(11) 0.0445(5) Uani 1 1 d . . .
C17 C 0.24118(12) 0.7510(5) 0.08114(13) 0.0531(5) Uani 1 1 d . . .
H17 H 0.2038 0.7580 0.0967 0.064 Uiso 1 1 calc R . .
O1 O 1.12539(10) -0.0815(3) 0.15425(12) 0.0707(5) Uani 1 1 d . . .
N1 N 1.15996(12) 0.3632(5) 0.18284(14) 0.0613(5) Uani 1 1 d . . .
H1A H 1.1451(17) 0.515(6) 0.1669(16) 0.074 Uiso 1 1 d . . .
H1B H 1.1708(17) 0.322(6) 0.2245(17) 0.074 Uiso 1 1 d . . .
C10 C 0.61276(12) 0.5732(4) 0.24187(11) 0.0468(5) Uani 1 1 d . . .
H10 H 0.6121 0.4756 0.2798 0.056 Uiso 1 1 calc R . .
C18 C 0.29351(12) 0.5646(4) 0.10462(12) 0.0494(5) Uani 1 1 d . . .
H18 H 0.2928 0.4414 0.1372 0.059 Uiso 1 1 calc R . .
C16 C 0.24398(12) 0.9347(4) 0.03270(12) 0.0505(5) Uani 1 1 d . . .
H16 H 0.2085 1.0665 0.0165 0.061 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
C2 C1 1.376(3) . ?
C2 C3 1.382(3) . ?
C5 C6 1.380(3) . ?
C5 C4 1.382(3) . ?
C3 C4 1.386(3) . ?
C6 C1 1.378(3) . ?
C1 S1 1.7759(19) . ?
C4 C7 1.501(3) . ?
S1 O2 1.4157(17) . ?
S1 O1 1.4250(16) . ?
S1 N1 1.613(2) . ?
O5 C13 1.235(2) . ?
O6 C14 1.247(2) . ?
N2 C18 1.360(2) . ?
N2 C14 1.366(2) . ?
N3 C11 1.337(3) . ?
N3 C12 1.338(3) . ?
N4 C13 1.321(2) . ?
O4 C7 1.306(3) . ?
O3 C7 1.212(3) . ?
C13 C8 1.504(3) . ?
C12 C8 1.382(2) . ?
C11 C10 1.371(3) . ?
C8 C9 1.385(3) . ?
C15 C16 1.352(3) . ?
C15 C14 1.428(3) . ?
C9 C10 1.379(3) . ?
C17 C18 1.340(3) . ?
C17 C16 1.397(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 C2 C3 118.97(19) . . ?
C6 C5 C4 120.34(19) . . ?
C2 C3 C4 120.68(18) . . ?
C1 C6 C5 119.46(18) . . ?
C2 C1 C6 121.16(18) . . ?
C2 C1 S1 119.50(15) . . ?
C6 C1 S1 119.29(15) . . ?
C5 C4 C3 119.35(18) . . ?
C5 C4 C7 119.05(18) . . ?
C3 C4 C7 121.60(18) . . ?
O2 S1 O1 120.24(12) . . ?
O2 S1 N1 106.54(13) . . ?
O1 S1 N1 105.99(12) . . ?
O2 S1 C1 108.62(10) . . ?
O1 S1 C1 107.07(10) . . ?
N1 S1 C1 107.82(10) . . ?
C18 N2 C14 123.91(17) . . ?
C11 N3 C12 118.27(16) . . ?
O5 C13 N4 122.46(17) . . ?
O5 C13 C8 119.07(16) . . ?
N4 C13 C8 118.46(15) . . ?
N3 C12 C8 122.90(18) . . ?
N3 C11 C10 122.66(18) . . ?
C12 C8 C9 117.83(17) . . ?
C12 C8 C13 123.66(16) . . ?
C9 C8 C13 118.50(16) . . ?
C16 C15 C14 120.84(19) . . ?
C10 C9 C8 119.54(17) . . ?
O6 C14 N2 119.48(17) . . ?
O6 C14 C15 125.53(18) . . ?
N2 C14 C15 114.99(17) . . ?
O3 C7 O4 124.54(19) . . ?
O3 C7 C4 122.26(19) . . ?
O4 C7 C4 113.20(18) . . ?
C18 C17 C16 118.52(19) . . ?
C11 C10 C9 118.80(18) . . ?
C17 C18 N2 120.6(2) . . ?
C15 C16 C17 121.07(19) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAC, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBANAMMEHP111
_database_code_depnum_ccdc_archive 'CCDC 1414172'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Sulfonamide benzoic acid; nicotinamide; 6methyl 2pyridone'
_chemical_name_common            
'Sulfonamide benzoic acid; nicotinamide; 6methyl 2pyridone'
_chemical_melting_point          423
_chemical_formula_moiety         C7H7NO4S,C6H6N2O,C6H7NO
_chemical_formula_sum            'C19 H20 N4 O6 S'
_chemical_formula_weight         432.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.2357(8)
_cell_length_b                   26.102(3)
_cell_length_c                   9.2781(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.283(2)
_cell_angle_gamma                90.00
_cell_volume                     1973.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5576
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.95

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_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    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            20165
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.98
_reflns_number_total             3854
_reflns_number_gt                3533
_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)+(0.0492P)²+1.0550P] 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         3854
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.204
_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 0.29996(7) 0.71894(2) 0.97826(6) 0.03667(17) Uani 1 1 d . . .
O5 O 1.0307(2) 0.36482(6) 0.16015(19) 0.0462(4) Uani 1 1 d . . .
O2 O 0.2372(2) 0.70442(7) 1.10843(17) 0.0511(5) Uani 1 1 d . . .
O4 O 0.6668(3) 0.54311(7) 0.6191(2) 0.0599(6) Uani 1 1 d . . .
N3 N 0.1725(3) 0.36166(8) 0.8842(2) 0.0423(5) Uani 1 1 d . . .
O1 O 0.4097(2) 0.76131(7) 0.9828(2) 0.0522(5) Uani 1 1 d . . .
N2 N 0.7939(3) 0.45809(8) 0.5183(2) 0.0530(6) Uani 1 1 d . . .
C6 C 0.3887(3) 0.61772(9) 0.9803(2) 0.0389(5) Uani 1 1 d . . .
H6 H 0.3364 0.6143 1.0621 0.047 Uiso 1 1 calc R . .
O3 O 0.6103(3) 0.49300(7) 0.7979(2) 0.0680(6) Uani 1 1 d . . .
C4 C 0.5373(3) 0.58073(8) 0.8016(2) 0.0356(5) Uani 1 1 d . . .
O6 O 0.1275(3) 0.44695(7) 0.8605(2) 0.0644(6) Uani 1 1 d . . .
C1 C 0.3965(3) 0.66459(8) 0.9142(2) 0.0334(5) Uani 1 1 d . . .
N4 N 0.9889(3) 0.44863(9) 0.1264(3) 0.0543(6) Uani 1 1 d . . .
C2 C 0.4743(3) 0.67009(9) 0.7924(2) 0.0412(5) Uani 1 1 d . . .
H2 H 0.4784 0.7019 0.7481 0.049 Uiso 1 1 calc R . .
C5 C 0.4596(3) 0.57578(9) 0.9238(2) 0.0411(5) Uani 1 1 d . . .
H5 H 0.4553 0.5439 0.9680 0.049 Uiso 1 1 calc R . .
C3 C 0.5450(3) 0.62831(9) 0.7377(2) 0.0409(5) Uani 1 1 d . . .
H3 H 0.5987 0.6320 0.6567 0.049 Uiso 1 1 calc R . .
C8 C 0.9199(3) 0.41018(8) 0.3454(2) 0.0371(5) Uani 1 1 d . . .
C19 C 0.6083(3) 0.53412(9) 0.7413(3) 0.0420(6) Uani 1 1 d . . .
N1 N 0.1450(3) 0.73269(9) 0.8581(2) 0.0403(5) Uani 1 1 d . . .
C13 C 0.1955(3) 0.40792(9) 0.8201(3) 0.0459(6) Uani 1 1 d . . .
C16 C 0.3330(3) 0.31580(10) 0.7418(3) 0.0499(6) Uani 1 1 d . . .
H16 H 0.3779 0.2853 0.7142 0.060 Uiso 1 1 calc R . .
C7 C 0.8535(3) 0.45442(9) 0.3930(3) 0.0474(6) Uani 1 1 d . . .
H7 H 0.8502 0.4834 0.3341 0.057 Uiso 1 1 calc R . .
C12 C 0.9844(3) 0.40667(8) 0.2027(2) 0.0380(5) Uani 1 1 d . . .
C17 C 0.2368(3) 0.31605(9) 0.8481(3) 0.0413(5) Uani 1 1 d . . .
C9 C 0.9250(3) 0.36787(9) 0.4351(3) 0.0487(6) Uani 1 1 d . . .
H9 H 0.9703 0.3373 0.4081 0.058 Uiso 1 1 calc R . .
C18 C 0.1941(3) 0.27064(10) 0.9315(3) 0.0571(7) Uani 1 1 d . . .
H18A H 0.2448 0.2407 0.8977 0.086 Uiso 1 1 calc R . .
H18B H 0.0772 0.2662 0.9175 0.086 Uiso 1 1 calc R . .
H18C H 0.2328 0.2757 1.0331 0.086 Uiso 1 1 calc R . .
C15 C 0.3646(4) 0.36176(12) 0.6739(3) 0.0563(7) Uani 1 1 d . . .
H15 H 0.4319 0.3615 0.6016 0.068 Uiso 1 1 calc R . .
C10 C 0.8629(4) 0.37106(10) 0.5643(3) 0.0576(7) Uani 1 1 d . . .
H10 H 0.8645 0.3427 0.6253 0.069 Uiso 1 1 calc R . .
C14 C 0.2999(4) 0.40644(11) 0.7105(3) 0.0550(7) Uani 1 1 d . . .
H14 H 0.3235 0.4365 0.6640 0.066 Uiso 1 1 calc R . .
C11 C 0.7985(4) 0.41675(10) 0.6018(3) 0.0524(7) Uani 1 1 d . . .
H11 H 0.7562 0.4188 0.6893 0.063 Uiso 1 1 calc R . .
H1B H 0.173(3) 0.7473(11) 0.786(3) 0.050(8) Uiso 1 1 d . . .
H1A H 0.088(3) 0.7067(11) 0.840(3) 0.043(7) Uiso 1 1 d . . .
H4A H 0.953(3) 0.4778(12) 0.150(3) 0.057(8) Uiso 1 1 d . . .
H4B H 1.024(4) 0.4470(12) 0.045(4) 0.066(9) Uiso 1 1 d . . .
H3A H 0.119(3) 0.3629(11) 0.957(3) 0.055(8) Uiso 1 1 d . . .
H4C H 0.706(4) 0.5147(14) 0.588(4) 0.089(12) 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 O1 1.4250(18) . ?
S1 O2 1.4317(17) . ?
S1 N1 1.610(2) . ?
S1 C1 1.771(2) . ?
O5 C12 1.240(3) . ?
O4 C19 1.315(3) . ?
N3 C17 1.364(3) . ?
N3 C13 1.371(3) . ?
N2 C11 1.326(3) . ?
N2 C7 1.329(3) . ?
C6 C1 1.374(3) . ?
C6 C5 1.380(3) . ?
O3 C19 1.194(3) . ?
C4 C3 1.382(3) . ?
C4 C5 1.385(3) . ?
C4 C19 1.494(3) . ?
O6 C13 1.246(3) . ?
C1 C2 1.385(3) . ?
N4 C12 1.308(3) . ?
C2 C3 1.368(3) . ?
C8 C7 1.377(3) . ?
C8 C9 1.380(3) . ?
C8 C12 1.498(3) . ?
C13 C14 1.424(4) . ?
C16 C17 1.351(3) . ?
C16 C15 1.397(4) . ?
C17 C18 1.485(4) . ?
C9 C10 1.372(4) . ?
C15 C14 1.346(4) . ?
C10 C11 1.370(4) . ?

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 O2 119.00(11) . . ?
O1 S1 N1 106.49(12) . . ?
O2 S1 N1 107.25(12) . . ?
O1 S1 C1 108.58(11) . . ?
O2 S1 C1 107.78(10) . . ?
N1 S1 C1 107.19(10) . . ?
C17 N3 C13 125.4(2) . . ?
C11 N2 C7 118.0(2) . . ?
C1 C6 C5 119.2(2) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 C19 121.77(19) . . ?
C5 C4 C19 118.9(2) . . ?
C6 C1 C2 120.9(2) . . ?
C6 C1 S1 120.77(16) . . ?
C2 C1 S1 118.28(17) . . ?
C3 C2 C1 119.5(2) . . ?
C6 C5 C4 120.5(2) . . ?
C2 C3 C4 120.6(2) . . ?
C7 C8 C9 117.1(2) . . ?
C7 C8 C12 122.8(2) . . ?
C9 C8 C12 120.0(2) . . ?
O3 C19 O4 123.8(2) . . ?
O3 C19 C4 123.3(2) . . ?
O4 C19 C4 112.9(2) . . ?
O6 C13 N3 119.6(2) . . ?
O6 C13 C14 125.5(2) . . ?
N3 C13 C14 114.9(2) . . ?
C17 C16 C15 119.4(2) . . ?
N2 C7 C8 123.7(2) . . ?
O5 C12 N4 122.1(2) . . ?
O5 C12 C8 120.0(2) . . ?
N4 C12 C8 117.9(2) . . ?
C16 C17 N3 118.2(2) . . ?
C16 C17 C18 125.7(2) . . ?
N3 C17 C18 116.1(2) . . ?
C10 C9 C8 119.7(2) . . ?
C14 C15 C16 121.6(2) . . ?
C11 C10 C9 118.8(2) . . ?
C15 C14 C13 120.4(3) . . ?
N2 C11 C10 122.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAC, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBANAMOMEHP212
_database_code_depnum_ccdc_archive 'CCDC 1414173'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Sulfonamide benzoic acid; nicotinamide; 3methoxy 2pyridone'
_chemical_name_common            
'Sulfonamide benzoic acid; nicotinamide; 3methoxy 2pyridone'
_chemical_melting_point          431
_chemical_formula_moiety         2(C7H7NO4S),C6H6N2O,2(C6H7NO2)
_chemical_formula_sum            'C32 H34 N6 O13 S2'
_chemical_formula_weight         774.77

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'

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'

_cell_length_a                   13.2514(3)
_cell_length_b                   7.05170(19)
_cell_length_c                   38.1412(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.962(2)
_cell_angle_gamma                90.00
_cell_volume                     3562.02(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4131
_cell_measurement_theta_min      4.1310
_cell_measurement_theta_max      71.5320

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_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    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    2.002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6038
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         4.64
_diffrn_reflns_theta_max         65.05
_reflns_number_total             3639
_reflns_number_gt                3595
_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)+(0.0624P)²+0.3910P] 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   0.040(13)
_refine_ls_number_reflns         3639
_refine_ls_number_parameters     505
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_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 0.31326(4) 0.14902(9) 0.210850(17) 0.03829(16) Uani 1 1 d . . .
O15 O 0.44885(18) 0.6254(3) 0.26090(6) 0.0505(5) Uani 1 1 d . . .
C22 C 0.4219(2) 0.6873(4) 0.29278(8) 0.0409(6) Uani 1 1 d . . .
N2 N 0.4054(2) 0.2385(4) 0.23312(7) 0.0439(5) Uani 1 1 d . . .
O5 O 0.25363(19) 0.0449(3) 0.23461(6) 0.0554(5) Uani 1 1 d . . .
O7 O 0.01902(16) 0.9017(3) 0.17296(6) 0.0504(5) Uani 1 1 d . . .
O6 O 0.35376(18) 0.0504(3) 0.18160(6) 0.0537(5) Uani 1 1 d . . .
N3 N 0.3294(2) 0.6059(3) 0.34277(6) 0.0426(5) Uani 1 1 d . . .
H3A H 0.2912 0.5296 0.3538 0.051 Uiso 1 1 calc R . .
C5 C 0.1221(2) 0.4482(4) 0.14828(7) 0.0431(6) Uani 1 1 d . . .
H5 H 0.0874 0.4314 0.1269 0.052 Uiso 1 1 calc R . .
O14 O 0.32958(18) 0.3993(3) 0.29711(6) 0.0527(5) Uani 1 1 d . . .
C7 C 0.0396(2) 0.7665(4) 0.15443(7) 0.0406(6) Uani 1 1 d . . .
C21 C 0.3578(2) 0.5530(4) 0.31024(7) 0.0405(6) Uani 1 1 d . . .
C2 C 0.2259(2) 0.5009(4) 0.21208(7) 0.0413(6) Uani 1 1 d . . .
H2 H 0.2611 0.5180 0.2334 0.050 Uiso 1 1 calc R . .
O8 O 0.00272(17) 0.7422(3) 0.12262(5) 0.0517(5) Uani 1 1 d . . .
H23 H -0.0371 0.8279 0.1177 0.078 Uiso 1 1 calc R . .
C1 C 0.23662(19) 0.3354(4) 0.19306(7) 0.0358(5) Uani 1 1 d . . .
C6 C 0.1857(2) 0.3080(4) 0.16132(7) 0.0426(6) Uani 1 1 d . . .
H6 H 0.1941 0.1962 0.1488 0.051 Uiso 1 1 calc R . .
C4 C 0.1099(2) 0.6142(4) 0.16718(7) 0.0365(5) Uani 1 1 d . . .
C26 C 0.5158(3) 0.7436(5) 0.24206(9) 0.0556(8) Uani 1 1 d . . .
H26A H 0.4849 0.8649 0.2379 0.083 Uiso 1 1 calc R . .
H26B H 0.5300 0.6851 0.2200 0.083 Uiso 1 1 calc R . .
H26C H 0.5776 0.7600 0.2556 0.083 Uiso 1 1 calc R . .
C23 C 0.4488(3) 0.8519(4) 0.30850(9) 0.0543(8) Uani 1 1 d . . .
H23A H 0.4890 0.9378 0.2968 0.065 Uiso 1 1 calc R . .
C3 C 0.1621(2) 0.6401(4) 0.19887(8) 0.0422(6) Uani 1 1 d . . .
H3 H 0.1540 0.7520 0.2114 0.051 Uiso 1 1 calc R . .
C24 C 0.4164(3) 0.8951(5) 0.34253(11) 0.0615(9) Uani 1 1 d . . .
H24 H 0.4359 1.0080 0.3534 0.074 Uiso 1 1 calc R . .
C25 C 0.3570(2) 0.7707(5) 0.35911(9) 0.0538(8) Uani 1 1 d . . .
H25 H 0.3351 0.7973 0.3815 0.065 Uiso 1 1 calc R . .
S2 S 0.70388(5) 1.11056(11) 0.45749(2) 0.04745(18) Uani 1 1 d . . .
O17 O 0.07515(19) 0.1193(4) 0.40957(7) 0.0603(6) Uani 1 1 d . . .
N6 N 0.1926(2) 0.1392(4) 0.32777(7) 0.0465(6) Uani 1 1 d . . .
O9 O 0.6641(2) 1.2212(4) 0.48498(7) 0.0656(6) Uani 1 1 d . . .
C27 C 0.1650(2) 0.1927(4) 0.36001(8) 0.0428(6) Uani 1 1 d . . .
C28 C 0.1003(2) 0.0592(5) 0.37747(8) 0.0481(7) Uani 1 1 d . . .
C8 C 0.7846(2) 0.9380(4) 0.47728(7) 0.0433(6) Uani 1 1 d . . .
O12 O 1.00832(19) 0.3962(3) 0.51212(7) 0.0577(6) Uani 1 1 d . . .
N1 N 0.6123(3) 1.0056(5) 0.43770(9) 0.0590(7) Uani 1 1 d . . .
C11 C 0.9187(2) 0.6877(4) 0.50937(8) 0.0429(6) Uani 1 1 d . . .
C12 C 0.9099(2) 0.8698(4) 0.52177(8) 0.0451(6) Uani 1 1 d . . .
H12 H 0.9493 0.9078 0.5412 0.054 Uiso 1 1 calc R . .
C9 C 0.7913(2) 0.7559(5) 0.46462(8) 0.0501(7) Uani 1 1 d . . .
H9 H 0.7512 0.7175 0.4454 0.060 Uiso 1 1 calc R . .
O10 O 0.7608(2) 1.2063(4) 0.43166(7) 0.0708(7) Uani 1 1 d . . .
C10 C 0.8588(3) 0.6297(5) 0.48088(9) 0.0534(8) Uani 1 1 d . . .
H10 H 0.8638 0.5062 0.4726 0.064 Uiso 1 1 calc R . .
C32 C 0.0079(3) 0.0038(7) 0.42864(11) 0.0732(11) Uani 1 1 d . . .
H32A H -0.0577 0.0050 0.4171 0.110 Uiso 1 1 calc R . .
H32B H 0.0030 0.0526 0.4520 0.110 Uiso 1 1 calc R . .
H32C H 0.0330 -0.1238 0.4296 0.110 Uiso 1 1 calc R . .
C13 C 0.8437(2) 0.9978(4) 0.50589(8) 0.0467(6) Uani 1 1 d . . .
H13 H 0.8389 1.1212 0.5142 0.056 Uiso 1 1 calc R . .
C14 C 0.9920(2) 0.5589(5) 0.52832(8) 0.0471(7) Uani 1 1 d . . .
O11 O 1.03167(19) 0.6034(4) 0.55615(6) 0.0608(6) Uani 1 1 d . . .
C29 C 0.0724(3) -0.1026(5) 0.36174(10) 0.0596(8) Uani 1 1 d . . .
H29 H 0.0315 -0.1876 0.3733 0.072 Uiso 1 1 calc R . .
C30 C 0.1043(3) -0.1462(5) 0.32772(11) 0.0663(10) Uani 1 1 d . . .
H30 H 0.0838 -0.2582 0.3167 0.080 Uiso 1 1 calc R . .
C31 C 0.1645(3) -0.0240(5) 0.31145(9) 0.0527(7) Uani 1 1 d . . .
H31 H 0.1869 -0.0512 0.2891 0.063 Uiso 1 1 calc R . .
O13 O 0.36331(16) 0.4746(3) 0.10197(5) 0.0493(5) Uani 1 1 d . . .
N5 N 0.14879(18) 0.7985(4) 0.04914(7) 0.0442(5) Uani 1 1 d . . .
C16 C 0.2076(2) 0.6932(4) 0.07080(7) 0.0400(6) Uani 1 1 d . . .
H16 H 0.1977 0.5627 0.0710 0.048 Uiso 1 1 calc R . .
C15 C 0.2818(2) 0.7682(4) 0.09261(7) 0.0360(5) Uani 1 1 d . . .
C19 C 0.2973(2) 0.9635(4) 0.09248(8) 0.0453(6) Uani 1 1 d . . .
H19 H 0.3466 1.0190 0.1071 0.054 Uiso 1 1 calc R . .
N4 N 0.3893(2) 0.6973(4) 0.14330(7) 0.0501(6) Uani 1 1 d . . .
H4A H 0.4283 0.6239 0.1556 0.060 Uiso 1 1 calc R . .
H4B H 0.3772 0.8104 0.1505 0.060 Uiso 1 1 calc R . .
C20 C 0.3481(2) 0.6363(4) 0.11335(7) 0.0380(6) Uani 1 1 d . . .
C18 C 0.2376(3) 1.0721(4) 0.07012(9) 0.0525(7) Uani 1 1 d . . .
H18 H 0.2458 1.2030 0.0694 0.063 Uiso 1 1 calc R . .
C17 C 0.1657(2) 0.9848(4) 0.04884(8) 0.0485(7) Uani 1 1 d . . .
H17 H 0.1270 1.0596 0.0335 0.058 Uiso 1 1 calc R . .
H6A H 0.232(3) 0.214(6) 0.3191(10) 0.054(10) Uiso 1 1 d . . .
O16 O 0.19394(19) 0.3443(4) 0.37360(6) 0.0614(6) Uani 1 1 d . . .
H2A H 0.437(3) 0.301(5) 0.2216(9) 0.038(9) Uiso 1 1 d . . .
H1A H 0.625(3) 0.944(6) 0.4205(10) 0.049(10) Uiso 1 1 d . . .
H2B H 0.388(3) 0.287(6) 0.2527(11) 0.059(11) Uiso 1 1 d . . .
H1B H 0.571(5) 0.947(9) 0.4473(18) 0.12(2) Uiso 1 1 d . . .
H1C H 1.057(5) 0.323(10) 0.5239(17) 0.15(3) 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 O5 1.426(2) . ?
S1 O6 1.434(2) . ?
S1 N2 1.594(3) . ?
S1 C1 1.781(3) . ?
O15 C22 1.352(4) . ?
O15 C26 1.429(4) . ?
C22 C23 1.349(4) . ?
C22 C21 1.449(4) . ?
O7 C7 1.222(4) . ?
N3 C21 1.361(4) . ?
N3 C25 1.363(4) . ?
C5 C6 1.381(4) . ?
C5 C4 1.387(4) . ?
O14 C21 1.246(4) . ?
C7 O8 1.304(3) . ?
C7 C4 1.493(4) . ?
C2 C3 1.380(4) . ?
C2 C1 1.384(4) . ?
C1 C6 1.380(4) . ?
C4 C3 1.384(4) . ?
C23 C24 1.414(5) . ?
C24 C25 1.350(5) . ?
S2 O9 1.423(2) . ?
S2 O10 1.430(3) . ?
S2 N1 1.590(4) . ?
S2 C8 1.772(3) . ?
O17 C28 1.348(4) . ?
O17 C32 1.425(4) . ?
N6 C27 1.348(4) . ?
N6 C31 1.355(4) . ?
C27 O16 1.243(4) . ?
C27 C28 1.450(4) . ?
C28 C29 1.335(5) . ?
C8 C9 1.376(4) . ?
C8 C13 1.387(4) . ?
O12 C14 1.324(4) . ?
C11 C12 1.375(4) . ?
C11 C10 1.385(4) . ?
C11 C14 1.497(4) . ?
C12 C13 1.384(4) . ?
C9 C10 1.393(5) . ?
C14 O11 1.210(4) . ?
C29 C30 1.413(6) . ?
C30 C31 1.341(5) . ?
O13 C20 1.239(3) . ?
N5 C17 1.333(4) . ?
N5 C16 1.341(4) . ?
C16 C15 1.371(4) . ?
C15 C19 1.393(4) . ?
C15 C20 1.489(4) . ?
C19 C18 1.376(4) . ?
N4 C20 1.321(4) . ?
C18 C17 1.376(5) . ?

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
O5 S1 O6 118.36(13) . . ?
O5 S1 N2 107.24(15) . . ?
O6 S1 N2 107.82(14) . . ?
O5 S1 C1 107.50(13) . . ?
O6 S1 C1 106.56(13) . . ?
N2 S1 C1 109.12(13) . . ?
C22 O15 C26 116.9(2) . . ?
C23 C22 O15 127.1(3) . . ?
C23 C22 C21 120.6(3) . . ?
O15 C22 C21 112.3(2) . . ?
C21 N3 C25 124.9(3) . . ?
C6 C5 C4 119.8(3) . . ?
O7 C7 O8 123.8(3) . . ?
O7 C7 C4 121.4(3) . . ?
O8 C7 C4 114.7(2) . . ?
O14 C21 N3 121.1(3) . . ?
O14 C21 C22 123.8(3) . . ?
N3 C21 C22 115.1(2) . . ?
C3 C2 C1 118.8(2) . . ?
C6 C1 C2 121.5(2) . . ?
C6 C1 S1 119.1(2) . . ?
C2 C1 S1 119.3(2) . . ?
C1 C6 C5 119.4(2) . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 C7 118.5(2) . . ?
C5 C4 C7 121.3(2) . . ?
C22 C23 C24 120.6(3) . . ?
C2 C3 C4 120.4(2) . . ?
C25 C24 C23 119.4(3) . . ?
C24 C25 N3 119.4(3) . . ?
O9 S2 O10 117.79(17) . . ?
O9 S2 N1 108.03(17) . . ?
O10 S2 N1 107.73(19) . . ?
O9 S2 C8 107.24(15) . . ?
O10 S2 C8 107.01(15) . . ?
N1 S2 C8 108.79(16) . . ?
C28 O17 C32 117.6(3) . . ?
C27 N6 C31 125.3(3) . . ?
O16 C27 N6 122.1(3) . . ?
O16 C27 C28 123.0(3) . . ?
N6 C27 C28 114.9(3) . . ?
C29 C28 O17 127.1(3) . . ?
C29 C28 C27 120.5(3) . . ?
O17 C28 C27 112.4(3) . . ?
C9 C8 C13 121.2(3) . . ?
C9 C8 S2 122.5(2) . . ?
C13 C8 S2 116.3(2) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 C14 117.5(3) . . ?
C10 C11 C14 123.0(3) . . ?
C11 C12 C13 121.2(3) . . ?
C8 C9 C10 119.2(3) . . ?
C11 C10 C9 120.2(3) . . ?
C12 C13 C8 118.6(3) . . ?
O11 C14 O12 124.1(3) . . ?
O11 C14 C11 121.4(3) . . ?
O12 C14 C11 114.5(3) . . ?
C28 C29 C30 120.8(3) . . ?
C31 C30 C29 119.1(3) . . ?
C30 C31 N6 119.5(3) . . ?
C17 N5 C16 117.2(3) . . ?
N5 C16 C15 123.3(3) . . ?
C16 C15 C19 118.8(3) . . ?
C16 C15 C20 118.6(2) . . ?
C19 C15 C20 122.4(2) . . ?
C18 C19 C15 118.1(3) . . ?
O13 C20 N4 122.3(3) . . ?
O13 C20 C15 119.3(2) . . ?
N4 C20 C15 118.4(2) . . ?
C19 C18 C17 119.2(3) . . ?
N5 C17 C18 123.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        65.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAC, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAOMEHP12
_database_code_depnum_ccdc_archive 'CCDC 1414174'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; 3methoxy 2pyridone'
_chemical_name_common            'Sulfonamide benzoic acid; 3methoxy 2pyridone'
_chemical_melting_point          441
_chemical_formula_moiety         C7H7NO4S,2(C6H7NO2)
_chemical_formula_sum            'C19 H21 N3 O8 S'
_chemical_formula_weight         451.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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                   6.95437(16)
_cell_length_b                   12.7192(3)
_cell_length_c                   23.9115(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.737(2)
_cell_angle_gamma                90.00
_cell_volume                     2112.66(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4514
_cell_measurement_theta_min      5.0510
_cell_measurement_theta_max      71.9930

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_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    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7314
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         67.07
_reflns_number_total             3756
_reflns_number_gt                3447
_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)+(0.0667P)²+0.4850P] 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         3756
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 -0.05675(6) 0.12840(3) 0.063909(17) 0.04101(15) Uani 1 1 d . . .
O1 O -0.13000(18) 0.02328(10) 0.06300(5) 0.0508(3) Uani 1 1 d . . .
O7 O 0.0859(2) 0.37563(10) 0.99686(7) 0.0647(4) Uani 1 1 d . . .
O8 O 0.3679(2) 0.25044(10) 0.96828(7) 0.0601(4) Uani 1 1 d . . .
C1 C 0.1616(2) 0.12947(13) 0.10581(7) 0.0410(4) Uani 1 1 d . . .
N3 N 0.2199(2) 0.51554(12) 0.95462(7) 0.0521(4) Uani 1 1 d . . .
H3A H 0.1262 0.5544 0.9645 0.063 Uiso 1 1 calc R . .
O4 O 0.7510(2) 0.23008(11) 0.21641(6) 0.0575(4) Uani 1 1 d . . .
C4 C 0.5087(3) 0.13615(14) 0.16556(7) 0.0443(4) Uani 1 1 d . . .
O3 O 0.7966(2) 0.05870(11) 0.20295(6) 0.0613(4) Uani 1 1 d . . .
O2 O -0.17381(19) 0.21142(11) 0.08352(6) 0.0544(3) Uani 1 1 d . . .
C6 C 0.2665(3) 0.03841(15) 0.11337(9) 0.0554(5) Uani 1 1 d . . .
H6 H 0.2207 -0.0248 0.0985 0.066 Uiso 1 1 calc R . .
C3 C 0.4005(3) 0.22600(15) 0.15841(8) 0.0512(4) Uani 1 1 d . . .
H3 H 0.4456 0.2891 0.1737 0.061 Uiso 1 1 calc R . .
C15 C 0.3785(3) 0.35148(14) 0.95194(8) 0.0465(4) Uani 1 1 d . . .
N1 N -0.0051(2) 0.15699(14) 0.00108(7) 0.0486(4) Uani 1 1 d . . .
H1A H 0.046(3) 0.219(2) -0.0002(9) 0.058 Uiso 1 1 d . . .
C7 C 0.7002(3) 0.13746(15) 0.19672(8) 0.0476(4) Uani 1 1 d . . .
C14 C 0.2182(3) 0.41306(14) 0.96954(8) 0.0465(4) Uani 1 1 d . . .
C5 C 0.4406(3) 0.04243(16) 0.14338(9) 0.0572(5) Uani 1 1 d . . .
H5 H 0.5129 -0.0186 0.1487 0.069 Uiso 1 1 calc R . .
C2 C 0.2252(3) 0.22342(15) 0.12871(8) 0.0516(4) Uani 1 1 d . . .
H2 H 0.1513 0.2841 0.1242 0.062 Uiso 1 1 calc R . .
C16 C 0.5183(3) 0.39651(17) 0.92239(9) 0.0590(5) Uani 1 1 d . . .
H16 H 0.6218 0.3564 0.9114 0.071 Uiso 1 1 calc R . .
C18 C 0.3600(3) 0.56135(17) 0.92510(10) 0.0636(5) Uani 1 1 d . . .
H18 H 0.3534 0.6327 0.9166 0.076 Uiso 1 1 calc R . .
C17 C 0.5074(4) 0.50354(18) 0.90829(11) 0.0694(6) Uani 1 1 d . . .
H17 H 0.6020 0.5341 0.8874 0.083 Uiso 1 1 calc R . .
C19 C 0.5151(4) 0.1811(2) 0.95192(14) 0.0834(8) Uani 1 1 d . . .
H19A H 0.5217 0.1824 0.9119 0.125 Uiso 1 1 calc R . .
H19B H 0.4868 0.1110 0.9639 0.125 Uiso 1 1 calc R . .
H19C H 0.6364 0.2031 0.9689 0.125 Uiso 1 1 calc R . .
O5 O 0.4277(2) 0.73482(11) 0.22773(7) 0.0632(4) Uani 1 1 d . . .
N2 N 0.3444(2) 0.56304(12) 0.23703(7) 0.0515(4) Uani 1 1 d . . .
H2A H 0.4534 0.5512 0.2544 0.062 Uiso 1 1 calc R . .
O6 O 0.0934(2) 0.77949(12) 0.17565(7) 0.0645(4) Uani 1 1 d . . .
C12 C 0.2213(3) 0.48010(16) 0.22964(9) 0.0576(5) Uani 1 1 d . . .
H12 H 0.2542 0.4143 0.2441 0.069 Uiso 1 1 calc R . .
C9 C 0.1236(3) 0.67794(16) 0.19019(7) 0.0500(4) Uani 1 1 d . . .
C10 C 0.0024(3) 0.59578(17) 0.18082(8) 0.0555(5) Uani 1 1 d . . .
H10 H -0.1142 0.6060 0.1609 0.067 Uiso 1 1 calc R . .
C8 C 0.3085(3) 0.66211(15) 0.21923(7) 0.0488(4) Uani 1 1 d . . .
C11 C 0.0520(3) 0.49444(17) 0.20122(9) 0.0610(5) Uani 1 1 d . . .
H11 H -0.0318 0.4382 0.1950 0.073 Uiso 1 1 calc R . .
C13 C -0.0904(3) 0.80554(19) 0.15047(10) 0.0694(6) Uani 1 1 d . . .
H13A H -0.1064 0.7712 0.1148 0.104 Uiso 1 1 calc R . .
H13B H -0.0990 0.8803 0.1454 0.104 Uiso 1 1 calc R . .
H13C H -0.1895 0.7826 0.1743 0.104 Uiso 1 1 calc R . .
H1B H 0.056(3) 0.1028(19) -0.0161(9) 0.059(6) Uiso 1 1 d . . .
H4A H 0.884(5) 0.224(2) 0.2370(14) 0.112(10) 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 1.4263(13) . ?
S1 O1 1.4305(13) . ?
S1 N1 1.6031(16) . ?
S1 C1 1.7788(18) . ?
O7 C14 1.248(2) . ?
O8 C15 1.346(2) . ?
O8 C19 1.420(2) . ?
C1 C6 1.376(2) . ?
C1 C2 1.379(2) . ?
N3 C14 1.352(2) . ?
N3 C18 1.361(3) . ?
O4 C7 1.311(2) . ?
C4 C3 1.375(3) . ?
C4 C5 1.379(3) . ?
C4 C7 1.495(2) . ?
O3 C7 1.211(2) . ?
C6 C5 1.379(3) . ?
C3 C2 1.382(3) . ?
C15 C16 1.356(3) . ?
C15 C14 1.441(2) . ?
C16 C17 1.404(3) . ?
C18 C17 1.339(3) . ?
O5 C8 1.252(2) . ?
N2 C8 1.350(2) . ?
N2 C12 1.365(3) . ?
O6 C9 1.351(2) . ?
O6 C13 1.425(2) . ?
C12 C11 1.343(3) . ?
C9 C10 1.355(3) . ?
C9 C8 1.446(3) . ?
C10 C11 1.415(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
O2 S1 O1 119.25(8) . . ?
O2 S1 N1 107.28(9) . . ?
O1 S1 N1 107.06(9) . . ?
O2 S1 C1 107.12(8) . . ?
O1 S1 C1 108.03(8) . . ?
N1 S1 C1 107.63(8) . . ?
C15 O8 C19 117.54(17) . . ?
C6 C1 C2 121.28(17) . . ?
C6 C1 S1 120.03(13) . . ?
C2 C1 S1 118.65(13) . . ?
C14 N3 C18 124.42(16) . . ?
C3 C4 C5 119.66(17) . . ?
C3 C4 C7 121.49(16) . . ?
C5 C4 C7 118.85(16) . . ?
C1 C6 C5 118.96(17) . . ?
C4 C3 C2 120.58(17) . . ?
O8 C15 C16 127.23(17) . . ?
O8 C15 C14 112.34(16) . . ?
C16 C15 C14 120.43(18) . . ?
O3 C7 O4 124.14(17) . . ?
O3 C7 C4 121.82(17) . . ?
O4 C7 C4 114.04(16) . . ?
O7 C14 N3 121.46(16) . . ?
O7 C14 C15 123.06(17) . . ?
N3 C14 C15 115.48(16) . . ?
C6 C5 C4 120.60(18) . . ?
C1 C2 C3 118.90(17) . . ?
C15 C16 C17 120.19(18) . . ?
C17 C18 N3 119.9(2) . . ?
C18 C17 C16 119.6(2) . . ?
C8 N2 C12 125.10(17) . . ?
C9 O6 C13 117.14(16) . . ?
C11 C12 N2 119.34(19) . . ?
O6 C9 C10 127.36(18) . . ?
O6 C9 C8 112.37(17) . . ?
C10 C9 C8 120.27(18) . . ?
C9 C10 C11 120.40(19) . . ?
O5 C8 N2 121.80(17) . . ?
O5 C8 C9 122.80(17) . . ?
N2 C8 C9 115.39(17) . . ?
C12 C11 C10 119.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.063
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAC, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAPAM11
_database_code_depnum_ccdc_archive 'CCDC 1414175'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; picolinamide'
_chemical_name_common            'Sulfonamide benzoic acid; picolinamide'
_chemical_melting_point          411
_chemical_formula_moiety         C7H7NO4S,C6H6N2O
_chemical_formula_sum            'C13 H13 N3 O5 S'
_chemical_formula_weight         323.32

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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                   10.2113(10)
_cell_length_b                   8.0850(6)
_cell_length_c                   17.663(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.033(9)
_cell_angle_gamma                90.00
_cell_volume                     1457.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1173
_cell_measurement_theta_min      3.4190
_cell_measurement_theta_max      25.6250

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_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    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5731
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         26.36
_reflns_number_total             2954
_reflns_number_gt                1883
_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)+(0.0449P)²+0.0456P] 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         2954
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.006
_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 0.79327(7) 0.43099(8) 0.20259(4) 0.0387(2) Uani 1 1 d . . .
O5 O 1.07420(19) 0.0781(2) 0.91813(12) 0.0520(5) Uani 1 1 d . . .
O2 O 0.84421(18) 0.5910(2) 0.18568(12) 0.0511(6) Uani 1 1 d . . .
O3 O 0.2048(2) 0.4021(2) 0.01985(13) 0.0590(6) Uani 1 1 d . . .
O1 O 0.87538(18) 0.2890(2) 0.19498(11) 0.0501(5) Uani 1 1 d . . .
C8 C 0.8479(3) 0.0724(3) 0.88101(16) 0.0399(7) Uani 1 1 d . . .
N1 N 0.7505(3) 0.4363(4) 0.28896(15) 0.0462(7) Uani 1 1 d . . .
O4 O 0.29839(19) 0.1744(2) -0.02452(12) 0.0562(6) Uani 1 1 d . . .
H4A H 0.2243 0.1567 -0.0421 0.084 Uiso 1 1 calc R . .
N2 N 0.7345(2) 0.1533(3) 0.88548(14) 0.0484(6) Uani 1 1 d . . .
C7 C 0.2985(3) 0.3110(3) 0.01530(16) 0.0414(7) Uani 1 1 d . . .
C4 C 0.4263(3) 0.3437(3) 0.05723(15) 0.0375(7) Uani 1 1 d . . .
C1 C 0.6514(2) 0.3977(3) 0.14403(15) 0.0362(7) Uani 1 1 d . . .
C3 C 0.5362(3) 0.2475(3) 0.04666(15) 0.0395(7) Uani 1 1 d . . .
H3 H 0.5338 0.1642 0.0103 0.047 Uiso 1 1 calc R . .
C6 C 0.5430(3) 0.4973(3) 0.15343(17) 0.0465(8) Uani 1 1 d . . .
H6 H 0.5462 0.5822 0.1890 0.056 Uiso 1 1 calc R . .
C2 C 0.6493(3) 0.2748(3) 0.08980(15) 0.0406(7) Uani 1 1 d . . .
H2 H 0.7235 0.2110 0.0824 0.049 Uiso 1 1 calc R . .
C13 C 0.9658(3) 0.1479(3) 0.92104(16) 0.0436(7) Uani 1 1 d . . .
C5 C 0.4306(3) 0.4705(3) 0.11010(16) 0.0463(8) Uani 1 1 d . . .
H5 H 0.3575 0.5372 0.1162 0.056 Uiso 1 1 calc R . .
N3 N 0.9477(2) 0.2885(3) 0.95667(15) 0.0604(7) Uani 1 1 d D . .
H3A H 1.0127 0.3370 0.9796 0.073 Uiso 1 1 calc R . .
H3B H 0.8708 0.3319 0.9571 0.073 Uiso 1 1 calc RD . .
C12 C 0.8610(3) -0.0739(4) 0.84225(18) 0.0533(8) Uani 1 1 d . . .
H12 H 0.9412 -0.1281 0.8417 0.064 Uiso 1 1 calc R . .
C10 C 0.6349(3) -0.0554(4) 0.80745(18) 0.0561(8) Uani 1 1 d . . .
H10 H 0.5602 -0.0950 0.7818 0.067 Uiso 1 1 calc R . .
C9 C 0.6311(3) 0.0867(4) 0.84935(19) 0.0553(9) Uani 1 1 d . . .
H9 H 0.5508 0.1401 0.8528 0.066 Uiso 1 1 calc R . .
C11 C 0.7523(3) -0.1380(4) 0.80425(18) 0.0629(9) Uani 1 1 d . . .
H11 H 0.7582 -0.2358 0.7768 0.076 Uiso 1 1 calc R . .
H1A H 0.718(3) 0.341(4) 0.3021(16) 0.058(10) Uiso 1 1 d . . .
H1B H 0.706(3) 0.520(4) 0.3023(18) 0.073(12) 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 1.4298(18) . ?
S1 O1 1.4308(17) . ?
S1 N1 1.602(3) . ?
S1 C1 1.770(3) . ?
O5 C13 1.245(3) . ?
O3 C7 1.212(3) . ?
C8 N2 1.335(3) . ?
C8 C12 1.375(4) . ?
C8 C13 1.504(4) . ?
O4 C7 1.309(3) . ?
N2 C9 1.329(4) . ?
C7 C4 1.501(4) . ?
C4 C3 1.384(3) . ?
C4 C5 1.386(4) . ?
C1 C2 1.380(3) . ?
C1 C6 1.383(4) . ?
C3 C2 1.378(3) . ?
C6 C5 1.374(4) . ?
C13 N3 1.316(3) . ?
C12 C11 1.378(4) . ?
C10 C9 1.367(4) . ?
C10 C11 1.375(4) . ?

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 119.18(12) . . ?
O2 S1 N1 106.75(14) . . ?
O1 S1 N1 106.94(14) . . ?
O2 S1 C1 108.15(11) . . ?
O1 S1 C1 107.06(11) . . ?
N1 S1 C1 108.38(14) . . ?
N2 C8 C12 123.4(3) . . ?
N2 C8 C13 117.1(2) . . ?
C12 C8 C13 119.5(3) . . ?
C9 N2 C8 116.7(3) . . ?
O3 C7 O4 124.2(3) . . ?
O3 C7 C4 122.3(3) . . ?
O4 C7 C4 113.4(2) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 C7 122.0(2) . . ?
C5 C4 C7 118.0(2) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 S1 120.49(19) . . ?
C6 C1 S1 118.9(2) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C6 C1 119.8(3) . . ?
C3 C2 C1 119.4(2) . . ?
O5 C13 N3 123.5(3) . . ?
O5 C13 C8 119.6(3) . . ?
N3 C13 C8 116.9(3) . . ?
C6 C5 C4 119.9(3) . . ?
C8 C12 C11 118.4(3) . . ?
C9 C10 C11 118.2(3) . . ?
N2 C9 C10 124.2(3) . . ?
C10 C11 C12 119.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.049
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAC, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAPAMMHP111
_database_code_depnum_ccdc_archive 'CCDC 1414176'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Sulfonamide benzoic acid; picolinamide; 6methyl 2pyridone'
_chemical_name_common            
'Sulfonamide benzoic acid; picolinamide; 6methyl 2pyridone'
_chemical_melting_point          408
_chemical_formula_moiety         C7H7NO4S,C6H6N2O,C6H7NO
_chemical_formula_sum            'C19 H20 N4 O6 S'
_chemical_formula_weight         432.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   11.5333(3)
_cell_length_b                   7.91065(17)
_cell_length_c                   22.4905(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.021(3)
_cell_angle_gamma                90.00
_cell_volume                     2020.65(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3917
_cell_measurement_theta_min      4.0710
_cell_measurement_theta_max      71.5330

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_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    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    1.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6819
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         5.07
_diffrn_reflns_theta_max         67.07
_reflns_number_total             3412
_reflns_number_gt                3125
_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)+(0.0518P)²+0.7782P] 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         3412
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.32448(4) 0.54851(5) 0.245855(19) 0.03935(15) Uani 1 1 d . . .
O1 O 0.26036(13) 0.50206(19) 0.29249(6) 0.0505(3) Uani 1 1 d . . .
O2 O 0.31855(15) 0.71843(18) 0.22443(6) 0.0572(4) Uani 1 1 d . . .
O6 O 0.06377(14) 0.68622(18) 0.98681(7) 0.0556(4) Uani 1 1 d . . .
O3 O 0.18361(15) 0.11589(19) -0.01578(6) 0.0596(4) Uani 1 1 d . . .
N5 N 0.04044(14) 0.4784(2) 0.91683(7) 0.0419(4) Uani 1 1 d . . .
H5 H 0.0191 0.4127 0.9434 0.050 Uiso 1 1 calc R . .
N1 N 0.46017(15) 0.5044(2) 0.27064(8) 0.0454(4) Uani 1 1 d . . .
H1A H 0.502(2) 0.526(3) 0.2440(11) 0.054 Uiso 1 1 d . . .
H1B H 0.471(2) 0.402(3) 0.2862(11) 0.054 Uiso 1 1 d . . .
O4 O 0.15443(19) -0.0740(2) 0.05259(7) 0.0740(5) Uani 1 1 d . . .
H4C H 0.1285 -0.1305 0.0227 0.111 Uiso 1 1 calc R . .
C11 C 0.18287(17) 0.0763(2) 0.03581(8) 0.0413(4) Uani 1 1 d . . .
C13 C 0.06977(16) 0.6415(2) 0.93374(9) 0.0422(4) Uani 1 1 d . . .
C14 C 0.21651(15) 0.1931(2) 0.08815(8) 0.0371(4) Uani 1 1 d . . .
C15 C 0.26408(19) 0.4734(2) 0.12536(8) 0.0451(4) Uani 1 1 d . . .
H15 H 0.2752 0.5876 0.1182 0.054 Uiso 1 1 calc R . .
C17 C 0.2301(2) 0.1341(3) 0.14730(9) 0.0508(5) Uani 1 1 d . . .
H17 H 0.2191 0.0200 0.1546 0.061 Uiso 1 1 calc R . .
C18 C 0.23442(18) 0.3626(2) 0.07779(8) 0.0445(4) Uani 1 1 d . . .
H18 H 0.2264 0.4023 0.0384 0.053 Uiso 1 1 calc R . .
C20 C 0.04251(17) 0.4129(3) 0.86125(9) 0.0439(4) Uani 1 1 d . . .
C21 C 0.27705(15) 0.4128(2) 0.18375(8) 0.0367(4) Uani 1 1 d . . .
C22 C 0.10443(19) 0.7454(3) 0.88943(10) 0.0523(5) Uani 1 1 d . . .
H22 H 0.1252 0.8573 0.8983 0.063 Uiso 1 1 calc R . .
C23 C 0.0064(2) 0.2340(3) 0.85098(10) 0.0601(6) Uani 1 1 d . . .
H23A H 0.0367 0.1687 0.8862 0.090 Uiso 1 1 calc R . .
H23B H 0.0370 0.1906 0.8170 0.090 Uiso 1 1 calc R . .
H23C H -0.0780 0.2269 0.8431 0.090 Uiso 1 1 calc R . .
C24 C 0.2596(2) 0.2433(3) 0.19469(8) 0.0502(5) Uani 1 1 d . . .
H24 H 0.2678 0.2038 0.2342 0.060 Uiso 1 1 calc R . .
C27 C 0.1077(2) 0.6820(3) 0.83352(11) 0.0631(6) Uani 1 1 d . . .
H27 H 0.1311 0.7516 0.8044 0.076 Uiso 1 1 calc R . .
C29 C 0.0769(2) 0.5156(3) 0.81899(10) 0.0572(5) Uani 1 1 d . . .
H29 H 0.0797 0.4745 0.7805 0.069 Uiso 1 1 calc R . .
O5 O 0.56944(14) 0.65438(19) 0.17399(6) 0.0564(4) Uani 1 1 d . . .
N3 N 0.64255(14) 0.4755(2) 0.04103(7) 0.0448(4) Uani 1 1 d . . .
N2 N 0.66866(16) 0.7620(2) 0.10531(8) 0.0509(4) Uani 1 1 d . . .
H2A H 0.6775 0.8582 0.1234 0.061 Uiso 1 1 calc R . .
H2B H 0.6969 0.7461 0.0728 0.061 Uiso 1 1 calc R . .
C12 C 0.60130(15) 0.4758(2) 0.09308(8) 0.0369(4) Uani 1 1 d . . .
C16 C 0.55266(18) 0.3354(3) 0.11567(9) 0.0454(4) Uani 1 1 d . . .
H16 H 0.5247 0.3411 0.1520 0.055 Uiso 1 1 calc R . .
C19 C 0.61192(16) 0.6391(2) 0.12744(8) 0.0394(4) Uani 1 1 d . . .
C25 C 0.58827(19) 0.1845(3) 0.02998(10) 0.0535(5) Uani 1 1 d . . .
H25 H 0.5854 0.0860 0.0072 0.064 Uiso 1 1 calc R . .
C26 C 0.54630(19) 0.1869(3) 0.08345(10) 0.0524(5) Uani 1 1 d . . .
H26 H 0.5142 0.0901 0.0976 0.063 Uiso 1 1 calc R . .
C28 C 0.63468(19) 0.3306(3) 0.01085(9) 0.0522(5) Uani 1 1 d . . .
H28 H 0.6624 0.3277 -0.0256 0.063 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 O2 1.4256(15) . ?
S1 O1 1.4323(14) . ?
S1 N1 1.6057(18) . ?
S1 C21 1.7709(18) . ?
O6 C13 1.258(2) . ?
O3 C11 1.203(2) . ?
N5 C20 1.357(2) . ?
N5 C13 1.371(2) . ?
O4 C11 1.306(2) . ?
C11 C14 1.493(2) . ?
C13 C22 1.402(3) . ?
C14 C18 1.383(3) . ?
C14 C17 1.393(3) . ?
C15 C18 1.379(3) . ?
C15 C21 1.381(3) . ?
C17 C24 1.368(3) . ?
C20 C29 1.361(3) . ?
C20 C23 1.482(3) . ?
C21 C24 1.385(3) . ?
C22 C27 1.360(3) . ?
C27 C29 1.387(3) . ?
O5 C19 1.237(2) . ?
N3 C28 1.328(3) . ?
N3 C12 1.338(2) . ?
N2 C19 1.317(2) . ?
C12 C16 1.380(3) . ?
C12 C19 1.500(2) . ?
C16 C26 1.376(3) . ?
C25 C26 1.372(3) . ?
C25 C28 1.374(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
O2 S1 O1 119.26(9) . . ?
O2 S1 N1 108.00(10) . . ?
O1 S1 N1 106.63(9) . . ?
O2 S1 C21 108.35(8) . . ?
O1 S1 C21 107.10(9) . . ?
N1 S1 C21 106.90(8) . . ?
C20 N5 C13 124.88(17) . . ?
O3 C11 O4 124.03(18) . . ?
O3 C11 C14 123.69(17) . . ?
O4 C11 C14 112.27(16) . . ?
O6 C13 N5 118.43(17) . . ?
O6 C13 C22 125.39(18) . . ?
N5 C13 C22 116.18(18) . . ?
C18 C14 C17 119.38(17) . . ?
C18 C14 C11 119.53(16) . . ?
C17 C14 C11 121.09(17) . . ?
C18 C15 C21 119.21(17) . . ?
C24 C17 C14 120.26(18) . . ?
C15 C18 C14 120.65(17) . . ?
N5 C20 C29 117.98(19) . . ?
N5 C20 C23 117.29(18) . . ?
C29 C20 C23 124.73(19) . . ?
C15 C21 C24 120.67(17) . . ?
C15 C21 S1 120.47(14) . . ?
C24 C21 S1 118.77(14) . . ?
C27 C22 C13 119.9(2) . . ?
C17 C24 C21 119.82(17) . . ?
C22 C27 C29 121.3(2) . . ?
C20 C29 C27 119.7(2) . . ?
C28 N3 C12 116.43(17) . . ?
N3 C12 C16 123.38(17) . . ?
N3 C12 C19 116.25(16) . . ?
C16 C12 C19 120.36(16) . . ?
C26 C16 C12 118.75(18) . . ?
O5 C19 N2 122.95(18) . . ?
O5 C19 C12 120.78(17) . . ?
N2 C19 C12 116.28(15) . . ?
C26 C25 C28 118.6(2) . . ?
C25 C26 C16 118.61(19) . . ?
N3 C28 C25 124.22(19) . . ?

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, THF'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_SMBAVLM11
_database_code_depnum_ccdc_archive 'CCDC 1414177'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sulfonamide benzoic acid; valerolactam'
_chemical_name_common            'Sulfonamide benzoic acid; valerolactam'
_chemical_melting_point          403
_chemical_formula_moiety         C7H7NO4S,C5H9NO
_chemical_formula_sum            'C12 H16 N2 O5 S'
_chemical_formula_weight         300.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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                   8.2121(5)
_cell_length_b                   9.3439(6)
_cell_length_c                   10.6539(8)
_cell_angle_alpha                112.237(7)
_cell_angle_beta                 106.403(6)
_cell_angle_gamma                95.743(5)
_cell_volume                     705.92(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2537
_cell_measurement_theta_min      2.245
_cell_measurement_theta_max      72.0060

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLES
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    2.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4110
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.78
_diffrn_reflns_theta_max         67.08
_reflns_number_total             2520
_reflns_number_gt                2331
_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)+(0.1113P)²+0.1521P] 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         2520
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1543
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.21057(6) 0.72830(6) 0.16087(5) 0.0410(2) Uani 1 1 d . . .
O5 O 0.6473(2) 0.68009(19) 0.16475(16) 0.0476(4) Uani 1 1 d . . .
O4 O 0.2559(2) 0.4112(2) 0.63151(19) 0.0572(5) Uani 1 1 d . . .
O1 O 0.3188(2) 0.88234(19) 0.21183(19) 0.0592(5) Uani 1 1 d . . .
O2 O 0.0250(2) 0.7025(2) 0.09921(19) 0.0542(4) Uani 1 1 d . . .
O3 O 0.4941(2) 0.6068(2) 0.76214(17) 0.0626(5) Uani 1 1 d . . .
N2 N 0.6776(3) 0.8321(2) 0.0516(2) 0.0443(4) Uani 1 1 d . . .
C4 C 0.3230(3) 0.5875(2) 0.5342(2) 0.0388(5) Uani 1 1 d . . .
N1 N 0.2694(3) 0.6058(3) 0.0402(2) 0.0481(5) Uani 1 1 d . . .
C7 C 0.3670(3) 0.5381(3) 0.6550(2) 0.0414(5) Uani 1 1 d . . .
C8 C 0.7141(3) 0.8098(2) 0.1702(2) 0.0391(5) Uani 1 1 d . . .
C6 C 0.1399(3) 0.5501(3) 0.2999(3) 0.0563(6) Uani 1 1 d . . .
H6 H 0.0407 0.4949 0.2180 0.068 Uiso 1 1 calc R . .
C2 C 0.3995(3) 0.7608(2) 0.4311(2) 0.0450(5) Uani 1 1 d . . .
H2 H 0.4743 0.8467 0.4373 0.054 Uiso 1 1 calc R . .
C3 C 0.4338(3) 0.7153(2) 0.5437(2) 0.0456(5) Uani 1 1 d . . .
H3 H 0.5321 0.7713 0.6262 0.055 Uiso 1 1 calc R . .
C1 C 0.2527(3) 0.6769(2) 0.3095(2) 0.0388(5) Uani 1 1 d . . .
C5 C 0.1755(3) 0.5063(3) 0.4120(3) 0.0549(6) Uani 1 1 d . . .
H5 H 0.0997 0.4211 0.4060 0.066 Uiso 1 1 calc R . .
C9 C 0.8295(4) 0.9418(3) 0.3102(3) 0.0598(7) Uani 1 1 d . . .
H9A H 0.9129 0.8986 0.3615 0.072 Uiso 1 1 calc R . .
H9B H 0.7586 0.9834 0.3684 0.072 Uiso 1 1 calc R . .
C10 C 0.9288(5) 1.0777(3) 0.2980(3) 0.0824(10) Uani 1 1 d . . .
H10A H 0.9655 1.1715 0.3893 0.099 Uiso 1 1 calc R . .
H10B H 1.0327 1.0507 0.2782 0.099 Uiso 1 1 calc R . .
C12 C 0.7540(4) 0.9709(3) 0.0388(3) 0.0634(7) Uani 1 1 d . . .
H12A H 0.6670 0.9919 -0.0311 0.076 Uiso 1 1 calc R . .
H12B H 0.8498 0.9495 0.0035 0.076 Uiso 1 1 calc R . .
C11 C 0.8196(6) 1.1140(4) 0.1803(4) 0.0907(11) Uani 1 1 d . . .
H11A H 0.7214 1.1506 0.2045 0.109 Uiso 1 1 calc R . .
H11B H 0.8886 1.1986 0.1724 0.109 Uiso 1 1 calc R . .
H1A H 0.368(4) 0.614(3) 0.064(3) 0.044(7) Uiso 1 1 d . . .
H1B H 0.205(4) 0.509(4) -0.003(3) 0.050(7) Uiso 1 1 d . . .
H2A H 0.614(3) 0.754(3) -0.027(3) 0.050(7) Uiso 1 1 d . . .
H4A H 0.293(5) 0.384(5) 0.700(5) 0.110(14) 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 O1 1.4268(17) . ?
S1 O2 1.4331(17) . ?
S1 N1 1.595(2) . ?
S1 C1 1.777(2) . ?
O5 C8 1.252(3) . ?
O4 C7 1.316(3) . ?
O3 C7 1.201(3) . ?
N2 C8 1.315(3) . ?
N2 C12 1.454(3) . ?
C4 C3 1.380(3) . ?
C4 C5 1.384(3) . ?
C4 C7 1.491(3) . ?
C8 C9 1.490(3) . ?
C6 C5 1.370(3) . ?
C6 C1 1.381(3) . ?
C2 C1 1.380(3) . ?
C2 C3 1.384(3) . ?
C9 C10 1.507(4) . ?
C10 C11 1.497(5) . ?
C12 C11 1.490(4) . ?

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 O2 119.64(10) . . ?
O1 S1 N1 107.91(12) . . ?
O2 S1 N1 106.37(11) . . ?
O1 S1 C1 107.10(10) . . ?
O2 S1 C1 107.02(10) . . ?
N1 S1 C1 108.41(10) . . ?
C8 N2 C12 126.0(2) . . ?
C3 C4 C5 119.50(19) . . ?
C3 C4 C7 119.08(18) . . ?
C5 C4 C7 121.4(2) . . ?
O3 C7 O4 123.7(2) . . ?
O3 C7 C4 122.6(2) . . ?
O4 C7 C4 113.67(18) . . ?
O5 C8 N2 119.68(19) . . ?
O5 C8 C9 121.03(19) . . ?
N2 C8 C9 119.3(2) . . ?
C5 C6 C1 119.4(2) . . ?
C1 C2 C3 119.1(2) . . ?
C4 C3 C2 120.41(19) . . ?
C2 C1 C6 120.86(19) . . ?
C2 C1 S1 119.89(16) . . ?
C6 C1 S1 119.23(16) . . ?
C6 C5 C4 120.7(2) . . ?
C8 C9 C10 115.3(2) . . ?
C11 C10 C9 111.4(3) . . ?
N2 C12 C11 111.5(2) . . ?
C12 C11 C10 111.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.08
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.126
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAC, THF'
_chemical_compound_source        synthetic
