# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1474270'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Piroxicam-Saccharin cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N4 O7 S2'
_chemical_formula_weight         514.52

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.516(5)
_cell_length_b                   10.397(5)
_cell_length_c                   12.669(5)
_cell_angle_alpha                66.973(5)
_cell_angle_beta                 71.019(5)
_cell_angle_gamma                89.378(5)
_cell_volume                     1081.1(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      65.65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.302
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Agilent Technologies SuperNova CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33446
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.919
_diffrn_reflns_theta_max         62.675
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             33446
_reflns_number_gt                26912
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+0.0609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         33446
_refine_ls_number_parameters     388
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.080
_refine_ls_shift/su_mean         0.002

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.95126(2) 0.05520(2) 1.26472(2) 0.01217(1) Uani 1 1 d . . . . .
O1 O 0.83701(4) -0.06301(4) 1.34449(3) 0.02084(6) Uani 1 1 d . . . . .
O2 O 1.03000(5) 0.10801(5) 1.32199(4) 0.02289(6) Uani 1 1 d . . . . .
O3 O 1.15836(4) 0.09875(4) 0.94526(2) 0.01838(5) Uani 1 1 d . . . . .
N1 N 1.07134(3) 0.02220(3) 1.15427(2) 0.01412(4) Uani 1 1 d D . . . .
C1 C 0.88780(3) 0.19215(4) 1.16334(3) 0.01252(4) Uani 1 1 d . . . . .
C2 C 0.78019(4) 0.27683(5) 1.19044(3) 0.01732(6) Uani 1 1 d D . . . .
C3 C 0.75104(5) 0.37992(5) 1.09188(4) 0.01953(6) Uani 1 1 d D . . . .
C4 C 0.82619(5) 0.39530(5) 0.97146(4) 0.02008(6) Uani 1 1 d D . . . .
C5 C 0.93263(5) 0.30778(5) 0.94712(3) 0.01845(6) Uani 1 1 d D . . . .
C6 C 0.96372(4) 0.20704(4) 1.04447(3) 0.01302(4) Uani 1 1 d . . . . .
C7 C 1.07505(4) 0.10667(4) 1.03788(3) 0.01311(4) Uani 1 1 d . . . . .
S1' S 0.63191(2) 0.55874(2) 0.67022(2) 0.01019(1) Uani 1 1 d . . . . .
O1' O 0.56763(3) 0.66441(3) 0.59337(2) 0.01557(4) Uani 1 1 d . . . . .
O2' O 0.71763(3) 0.60053(3) 0.72908(3) 0.01410(3) Uani 1 1 d . . . . .
O3' O 0.71989(3) 0.14451(3) 0.85045(2) 0.01382(4) Uani 1 1 d . . . . .
O4' O 0.36252(3) 0.31016(3) 1.02600(2) 0.01579(4) Uani 1 1 d . . . . .
N1' N 0.49767(3) 0.43411(3) 0.77481(2) 0.01085(3) Uani 1 1 d . . . . .
N2' N 0.52385(3) 0.14351(3) 1.04852(2) 0.01193(3) Uani 1 1 d D . . . .
N3' N 0.37035(3) 0.13354(3) 1.23980(2) 0.01138(3) Uani 1 1 d D . . . .
C1' C 0.55068(3) 0.31273(3) 0.84742(2) 0.01038(3) Uani 1 1 d . . . . .
C2' C 0.67083(3) 0.25564(3) 0.79145(2) 0.00990(3) Uani 1 1 d . . . . .
C3' C 0.75004(3) 0.32711(3) 0.65618(2) 0.00995(3) Uani 1 1 d . . . . .
C4' C 0.83899(3) 0.25304(4) 0.59400(3) 0.01222(4) Uani 1 1 d D . . . .
C5' C 0.91753(4) 0.31907(4) 0.46870(3) 0.01498(5) Uani 1 1 d D . . . .
C6' C 0.90916(4) 0.46067(5) 0.40361(3) 0.01640(5) Uani 1 1 d D . . . .
C7' C 0.82055(4) 0.53712(4) 0.46275(3) 0.01405(4) Uani 1 1 d D . . . .
C8' C 0.74222(3) 0.46899(3) 0.58810(2) 0.01055(3) Uani 1 1 d . . . . .
C9' C 0.46995(3) 0.25893(3) 0.97837(2) 0.01102(4) Uani 1 1 d . . . . .
C10' C 0.48011(3) 0.08456(3) 1.17282(2) 0.01013(3) Uani 1 1 d . . . . .
C11' C 0.55009(3) -0.02593(4) 1.23341(3) 0.01214(4) Uani 1 1 d D . . . .
C12' C 0.50476(4) -0.08063(4) 1.35930(3) 0.01321(4) Uani 1 1 d D . . . .
C13' C 0.38990(4) -0.02672(4) 1.42598(3) 0.01303(4) Uani 1 1 d D . . . .
C14' C 0.32469(3) 0.08091(4) 1.36375(3) 0.01232(4) Uani 1 1 d D . . . .
C15' C 0.37574(4) 0.40382(4) 0.73628(4) 0.01693(5) Uani 1 1 d D . . . .
H1A H 1.1397(4) -0.0531(3) 1.1661(11) 0.044(4) Uiso 1 1 d D . . . .
H2 H 0.7266(11) 0.2755(6) 1.2806(2) 0.033(3) Uiso 1 1 d D . . . .
H3 H 0.6679(4) 0.4479(4) 1.1097(7) 0.037(3) Uiso 1 1 d D . . . .
H4 H 0.8082(7) 0.4827(5) 0.8972(4) 0.032(3) Uiso 1 1 d D . . . .
H5 H 0.9839(12) 0.3147(7) 0.8549(2) 0.039(3) Uiso 1 1 d D . . . .
H2A' H 0.6073(5) 0.1105(5) 0.9962(4) 0.037(3) Uiso 1 1 d D . . . .
H3A' H 0.3176(5) 0.2094(4) 1.1955(5) 0.029(3) Uiso 1 1 d D . . . .
H4' H 0.8430(9) 0.1418(2) 0.6421(7) 0.019(2) Uiso 1 1 d D . . . .
H5' H 0.9844(7) 0.2640(4) 0.4172(3) 0.032(3) Uiso 1 1 d D . . . .
H6' H 0.9742(9) 0.5123(12) 0.30685(19) 0.038(3) Uiso 1 1 d D . . . .
H7' H 0.8146(9) 0.6475(2) 0.4130(7) 0.020(2) Uiso 1 1 d D . . . .
H11' H 0.6349(5) -0.0655(5) 1.1774(4) 0.047(4) Uiso 1 1 d D . . . .
H12' H 0.5520(5) -0.1656(4) 1.4136(4) 0.024(2) Uiso 1 1 d D . . . .
H13' H 0.3536(12) -0.0729(12) 1.52495(6) 0.030(3) Uiso 1 1 d D . . . .
H14' H 0.2365(5) 0.1313(4) 1.4052(5) 0.037(3) Uiso 1 1 d D . . . .
H15A H 0.4043(12) 0.3495(3) 0.6777(2) 0.028(3) Uiso 1 1 d D . . . .
H15B H 0.3267(5) 0.4936(4) 0.6942(6) 0.025(2) Uiso 1 1 d D . . . .
H15C H 0.2891(6) 0.3329(7) 0.8164(4) 0.035(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
S1 O1 1.4340(6) . ?
S1 O2 1.4365(5) . ?
S1 N1 1.6458(5) . ?
S1 C1 1.7597(6) . ?
O3 C7 1.2170(5) . ?
N1 C7 1.3785(6) . ?
N1 H1A 1.0090(4) . ?
C1 C6 1.3879(7) . ?
C1 C2 1.3892(6) . ?
C2 C3 1.3988(7) . ?
C2 H2 1.0830(4) . ?
C3 C4 1.4023(8) . ?
C3 H3 1.0830(4) . ?
C4 C5 1.3948(7) . ?
C4 H4 1.0830(3) . ?
C5 C6 1.3877(6) . ?
C5 H5 1.0830(4) . ?
C6 C7 1.4849(7) . ?
S1' O1' 1.4371(5) . ?
S1' O2' 1.4377(5) . ?
S1' N1' 1.6305(6) . ?
S1' C8' 1.7558(6) . ?
O3' C2' 1.2850(5) . ?
O4' C9' 1.2374(5) . ?
N1' C1' 1.4398(6) . ?
N1' C15' 1.4765(7) . ?
N2' C10' 1.3612(6) . ?
N2' C9' 1.3935(6) . ?
N2' H2A' 1.0090(3) . ?
N3' C10' 1.3492(5) . ?
N3' C14' 1.3576(7) . ?
N3' H3A' 1.0090(3) . ?
C1' C2' 1.3962(6) . ?
C1' C9' 1.4525(6) . ?
C2' C3' 1.4943(6) . ?
C3' C4' 1.3989(6) . ?
C3' C8' 1.4033(7) . ?
C4' C5' 1.3916(7) . ?
C4' H4' 1.0830(5) . ?
C5' C6' 1.3943(8) . ?
C5' H5' 1.0830(3) . ?
C6' C7' 1.3945(7) . ?
C6' H6' 1.0830(4) . ?
C7' C8' 1.3931(6) . ?
C7' H7' 1.0830(5) . ?
C10' C11' 1.4065(6) . ?
C11' C12' 1.3788(7) . ?
C11' H11' 1.0830(3) . ?
C12' C13' 1.4068(6) . ?
C12' H12' 1.0830(3) . ?
C13' C14' 1.3681(6) . ?
C13' H13' 1.0830(5) . ?
C14' H14' 1.0830(4) . ?
C15' H15A 1.0660(3) . ?
C15' H15B 1.0660(4) . ?
C15' H15C 1.0660(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
O1 S1 O2 116.36(4) . . ?
O1 S1 N1 110.81(4) . . ?
O2 S1 N1 110.11(4) . . ?
O1 S1 C1 112.46(4) . . ?
O2 S1 C1 111.39(4) . . ?
N1 S1 C1 93.38(3) . . ?
C7 N1 S1 115.21(4) . . ?
C7 N1 H1A 119.6(7) . . ?
S1 N1 H1A 125.2(7) . . ?
C6 C1 C2 122.32(3) . . ?
C6 C1 S1 109.27(3) . . ?
C2 C1 S1 128.41(3) . . ?
C1 C2 C3 117.04(4) . . ?
C1 C2 H2 124.4(4) . . ?
C3 C2 H2 118.2(4) . . ?
C2 C3 C4 121.17(4) . . ?
C2 C3 H3 119.0(5) . . ?
C4 C3 H3 119.8(5) . . ?
C5 C4 C3 120.52(3) . . ?
C5 C4 H4 120.5(3) . . ?
C3 C4 H4 118.7(3) . . ?
C6 C5 C4 118.45(4) . . ?
C6 C5 H5 121.3(4) . . ?
C4 C5 H5 120.1(5) . . ?
C5 C6 C1 120.48(4) . . ?
C5 C6 C7 126.85(3) . . ?
C1 C6 C7 112.67(3) . . ?
O3 C7 N1 124.25(4) . . ?
O3 C7 C6 126.29(3) . . ?
N1 C7 C6 109.46(3) . . ?
O1' S1' O2' 118.71(4) . . ?
O1' S1' N1' 108.28(4) . . ?
O2' S1' N1' 108.55(4) . . ?
O1' S1' C8' 109.75(3) . . ?
O2' S1' C8' 108.44(4) . . ?
N1' S1' C8' 101.77(4) . . ?
C1' N1' C15' 115.71(4) . . ?
C1' N1' S1' 113.47(4) . . ?
C15' N1' S1' 115.89(4) . . ?
C10' N2' C9' 125.96(3) . . ?
C10' N2' H2A' 121.8(3) . . ?
C9' N2' H2A' 112.1(3) . . ?
C10' N3' C14' 122.69(3) . . ?
C10' N3' H3A' 118.0(4) . . ?
C14' N3' H3A' 119.2(4) . . ?
C2' C1' N1' 120.39(3) . . ?
C2' C1' C9' 124.91(3) . . ?
N1' C1' C9' 114.70(3) . . ?
O3' C2' C1' 123.47(3) . . ?
O3' C2' C3' 117.22(3) . . ?
C1' C2' C3' 119.30(3) . . ?
C4' C3' C8' 117.89(4) . . ?
C4' C3' C2' 119.80(4) . . ?
C8' C3' C2' 122.29(3) . . ?
C5' C4' C3' 120.66(4) . . ?
C5' C4' H4' 119.0(5) . . ?
C3' C4' H4' 120.2(5) . . ?
C4' C5' C6' 120.22(3) . . ?
C4' C5' H5' 122.6(2) . . ?
C6' C5' H5' 117.2(2) . . ?
C5' C6' C7' 120.51(4) . . ?
C5' C6' H6' 119.7(7) . . ?
C7' C6' H6' 119.8(7) . . ?
C8' C7' C6' 118.41(4) . . ?
C8' C7' H7' 120.7(5) . . ?
C6' C7' H7' 120.9(5) . . ?
C7' C8' C3' 122.30(3) . . ?
C7' C8' S1' 121.31(4) . . ?
C3' C8' S1' 116.37(3) . . ?
O4' C9' N2' 121.61(4) . . ?
O4' C9' C1' 123.86(3) . . ?
N2' C9' C1' 114.52(3) . . ?
N3' C10' N2' 120.20(3) . . ?
N3' C10' C11' 118.92(4) . . ?
N2' C10' C11' 120.86(3) . . ?
C12' C11' C10' 119.06(3) . . ?
C12' C11' H11' 123.7(3) . . ?
C10' C11' H11' 117.2(3) . . ?
C11' C12' C13' 120.36(3) . . ?
C11' C12' H12' 124.2(3) . . ?
C13' C12' H12' 115.4(3) . . ?
C14' C13' C12' 118.86(4) . . ?
C14' C13' H13' 121.7(7) . . ?
C12' C13' H13' 119.4(7) . . ?
N3' C14' C13' 120.11(3) . . ?
N3' C14' H14' 114.6(3) . . ?
C13' C14' H14' 125.3(3) . . ?
N1' C15' H15A 115.1(6) . . ?
N1' C15' H15B 114.8(3) . . ?
H15A C15' H15B 107.4(6) . . ?
N1' C15' H15C 107.4(4) . . ?
H15A C15' H15C 104.2(6) . . ?
H15B C15' H15C 107.2(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C7 115.91(4) . . . . ?
O2 S1 N1 C7 -113.93(4) . . . . ?
C1 S1 N1 C7 0.32(3) . . . . ?
O1 S1 C1 C6 -113.88(4) . . . . ?
O2 S1 C1 C6 113.43(4) . . . . ?
N1 S1 C1 C6 0.29(3) . . . . ?
O1 S1 C1 C2 66.33(5) . . . . ?
O2 S1 C1 C2 -66.36(5) . . . . ?
N1 S1 C1 C2 -179.50(4) . . . . ?
C6 C1 C2 C3 -0.30(7) . . . . ?
S1 C1 C2 C3 179.46(4) . . . . ?
C1 C2 C3 C4 0.79(7) . . . . ?
C2 C3 C4 C5 -0.17(8) . . . . ?
C3 C4 C5 C6 -0.96(8) . . . . ?
C4 C5 C6 C1 1.45(7) . . . . ?
C4 C5 C6 C7 -178.39(4) . . . . ?
C2 C1 C6 C5 -0.83(6) . . . . ?
S1 C1 C6 C5 179.37(3) . . . . ?
C2 C1 C6 C7 179.02(4) . . . . ?
S1 C1 C6 C7 -0.78(4) . . . . ?
S1 N1 C7 O3 178.83(4) . . . . ?
S1 N1 C7 C6 -0.79(4) . . . . ?
C5 C6 C7 O3 1.24(7) . . . . ?
C1 C6 C7 O3 -178.61(4) . . . . ?
C5 C6 C7 N1 -179.15(4) . . . . ?
C1 C6 C7 N1 1.01(5) . . . . ?
O1' S1' N1' C1' 172.00(2) . . . . ?
O2' S1' N1' C1' -57.88(3) . . . . ?
C8' S1' N1' C1' 56.38(3) . . . . ?
O1' S1' N1' C15' 34.56(3) . . . . ?
O2' S1' N1' C15' 164.69(3) . . . . ?
C8' S1' N1' C15' -81.06(3) . . . . ?
C15' N1' C1' C2' 91.82(5) . . . . ?
S1' N1' C1' C2' -45.69(4) . . . . ?
C15' N1' C1' C9' -88.21(5) . . . . ?
S1' N1' C1' C9' 134.28(3) . . . . ?
N1' C1' C2' O3' -177.31(3) . . . . ?
C9' C1' C2' O3' 2.72(5) . . . . ?
N1' C1' C2' C3' 3.81(5) . . . . ?
C9' C1' C2' C3' -176.16(3) . . . . ?
O3' C2' C3' C4' 19.54(5) . . . . ?
C1' C2' C3' C4' -161.51(3) . . . . ?
O3' C2' C3' C8' -158.65(3) . . . . ?
C1' C2' C3' C8' 20.30(5) . . . . ?
C8' C3' C4' C5' 0.37(5) . . . . ?
C2' C3' C4' C5' -177.90(3) . . . . ?
C3' C4' C5' C6' 0.41(5) . . . . ?
C4' C5' C6' C7' -0.91(6) . . . . ?
C5' C6' C7' C8' 0.60(6) . . . . ?
C6' C7' C8' C3' 0.20(5) . . . . ?
C6' C7' C8' S1' 178.38(3) . . . . ?
C4' C3' C8' C7' -0.68(5) . . . . ?
C2' C3' C8' C7' 177.54(3) . . . . ?
C4' C3' C8' S1' -178.95(2) . . . . ?
C2' C3' C8' S1' -0.72(4) . . . . ?
O1' S1' C8' C7' 32.88(4) . . . . ?
O2' S1' C8' C7' -98.26(4) . . . . ?
N1' S1' C8' C7' 147.42(3) . . . . ?
O1' S1' C8' C3' -148.84(3) . . . . ?
O2' S1' C8' C3' 80.03(4) . . . . ?
N1' S1' C8' C3' -34.30(3) . . . . ?
C10' N2' C9' O4' -7.86(6) . . . . ?
C10' N2' C9' C1' 171.64(3) . . . . ?
C2' C1' C9' O4' -179.10(4) . . . . ?
N1' C1' C9' O4' 0.93(5) . . . . ?
C2' C1' C9' N2' 1.40(5) . . . . ?
N1' C1' C9' N2' -178.57(3) . . . . ?
C14' N3' C10' N2' -178.45(3) . . . . ?
C14' N3' C10' C11' 0.27(5) . . . . ?
C9' N2' C10' N3' 3.16(5) . . . . ?
C9' N2' C10' C11' -175.53(3) . . . . ?
N3' C10' C11' C12' -0.15(5) . . . . ?
N2' C10' C11' C12' 178.55(3) . . . . ?
C10' C11' C12' C13' 0.14(5) . . . . ?
C11' C12' C13' C14' -0.22(6) . . . . ?
C10' N3' C14' C13' -0.36(5) . . . . ?
C12' C13' C14' N3' 0.33(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11' H11' O3 1.0830(3) 2.1957(17) 3.2564(11) 165.8(5) 2_757
C15' H15C O3 1.0660(3) 2.403(4) 3.3703(12) 150.2(6) 1_455
N1 H1A O3' 1.0090(4) 1.637(2) 2.6237(10) 164.6(7) 2_757
N2' H2A' O3' 1.0090(3) 1.701(3) 2.5907(9) 144.7(4) .
N3' H3A' O2' 1.0090(3) 2.487(7) 3.0148(13) 112.1(5) 2_667
N3' H3A' O4' 1.0090(3) 1.882(5) 2.6366(9) 129.0(5) .
C11' H11' O3 1.0830(3) 2.1957(17) 3.2564(11) 165.8(5) 2_757
C15' H15C O3 1.0660(3) 2.403(4) 3.3703(12) 150.2(6) 1_455

_refine_diff_density_max         1.135
_refine_diff_density_min         -1.392
_refine_diff_density_rms         0.088



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1474328'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT150_shelx               
;
PROBLEM: Volume as Calculated Differs from that Given ...    1455.90 Ang-3
RESPONSE: I don't know
;
_vrf_SHFSU01_shelx               
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.10
RESPONSE: DFix on H atoms to standard Neutron Distances
;
_vrf_PLAT080_shelx               
;
PROBLEM: Maximum Shift/Error ............................       0.12 Why ?
RESPONSE: DFix on H atoms to standard Neutron Distances
;
# Added during the CSD deposition process: Friday 15 April 2016 12:55 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Piroxicam
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 O4 S'
_chemical_formula_weight         331.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.034
_cell_length_b                   14.98940(10)
_cell_length_c                   13.89390(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.3870(10)
_cell_angle_gamma                90
_cell_volume                     1455.900(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      65.67

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Agilent Technologies SuperNova CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15187
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         52.157
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             15187
_reflns_number_gt                12915
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.0253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15187
_refine_ls_number_parameters     260
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.116
_refine_ls_shift/su_mean         0.004

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.05515(2) 0.40556(2) 0.09911(2) 0.00877(2) Uani 1 1 d . . . . .
O1 O 0.19437(4) 0.38896(2) 0.03308(2) 0.01302(4) Uani 1 1 d . . . . .
O2 O 0.05314(5) 0.49069(2) 0.14585(3) 0.01379(5) Uani 1 1 d . . . . .
O3 O -0.12502(5) 0.14271(2) 0.02570(3) 0.01520(5) Uani 1 1 d D . . . .
O4 O -0.32385(5) 0.20859(2) -0.12333(3) 0.01598(5) Uani 1 1 d . . . . .
N1 N -0.15886(4) 0.38749(2) 0.04165(2) 0.00937(4) Uani 1 1 d . . . . .
N2 N -0.33923(4) 0.36133(2) -0.14025(3) 0.01120(4) Uani 1 1 d D . . . .
N3 N -0.46986(5) 0.45661(2) -0.25748(3) 0.01570(5) Uani 1 1 d . . . . .
C1 C -0.18206(4) 0.29806(2) 0.00512(3) 0.00979(5) Uani 1 1 d . . . . .
C2 C -0.10753(5) 0.22656(2) 0.05814(3) 0.01014(5) Uani 1 1 d . . . . .
C3 C -0.00345(4) 0.23710(2) 0.15509(3) 0.00971(4) Uani 1 1 d . . . . .
C4 C 0.01986(5) 0.16569(2) 0.22021(3) 0.01203(5) Uani 1 1 d D . . . .
C5 C 0.11086(6) 0.17929(2) 0.31323(3) 0.01389(6) Uani 1 1 d D . . . .
C6 C 0.17879(6) 0.26342(3) 0.34293(3) 0.01483(6) Uani 1 1 d D . . . .
C7 C 0.16034(6) 0.33525(2) 0.27875(3) 0.01310(5) Uani 1 1 d D . . . .
C8 C 0.07155(5) 0.32055(2) 0.18589(3) 0.00979(4) Uani 1 1 d . . . . .
C9 C -0.28680(5) 0.28527(2) -0.09140(3) 0.01077(5) Uani 1 1 d . . . . .
C10 C -0.43156(5) 0.37128(2) -0.23474(3) 0.01106(5) Uani 1 1 d . . . . .
C11 C -0.47625(5) 0.30011(2) -0.29841(3) 0.01304(5) Uani 1 1 d D . . . .
C12 C -0.56511(6) 0.31999(3) -0.39004(3) 0.01620(6) Uani 1 1 d D . . . .
C13 C -0.60672(7) 0.40838(3) -0.41550(4) 0.01938(7) Uani 1 1 d D . . . .
C14 C -0.55586(7) 0.47398(3) -0.34656(4) 0.01954(7) Uani 1 1 d D . . . .
C15 C -0.32061(5) 0.42317(2) 0.09035(3) 0.01414(6) Uani 1 1 d D . . . .
H2A H -0.2810(6) 0.41717(12) -0.1089(3) 0.026(3) Uiso 1 1 d D . . . .
H3A H -0.2054(4) 0.1493(7) -0.03501(13) 0.039(3) Uiso 1 1 d D . . . .
H4 H -0.0426(5) 0.10207(11) 0.1972(4) 0.020(2) Uiso 1 1 d D . . . .
H5 H 0.1285(16) 0.12289(12) 0.36212(16) 0.028(3) Uiso 1 1 d D . . . .
H6 H 0.2559(5) 0.2741(5) 0.41390(12) 0.028(3) Uiso 1 1 d D . . . .
H7 H 0.2229(5) 0.39984(11) 0.2974(5) 0.030(3) Uiso 1 1 d D . . . .
H11 H -0.4455(10) 0.23148(10) -0.2779(4) 0.036(3) Uiso 1 1 d D . . . .
H12 H -0.5977(12) 0.26784(13) -0.44327(16) 0.032(3) Uiso 1 1 d D . . . .
H13 H -0.6841(5) 0.4280(3) -0.48396(13) 0.026(2) Uiso 1 1 d D . . . .
H14 H -0.5792(13) 0.54397(10) -0.3632(5) 0.044(3) Uiso 1 1 d D . . . .
H15A H -0.4495(3) 0.4076(4) 0.0467(2) 0.032(3) Uiso 1 1 d D . . . .
H15B H -0.3001(11) 0.49307(8) 0.0956(8) 0.029(3) Uiso 1 1 d D . . . .
H15C H -0.3185(15) 0.3921(2) 0.15891(11) 0.031(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
S1 O2 1.4326(3) . ?
S1 O1 1.4362(3) . ?
S1 N1 1.6461(3) . ?
S1 C8 1.7492(3) . ?
O3 C2 1.3362(4) . ?
O3 H3A 0.96700(5) . ?
O4 C9 1.2492(4) . ?
N1 C1 1.4362(4) . ?
N1 C15 1.4865(4) . ?
N2 C9 1.3568(4) . ?
N2 C10 1.4064(5) . ?
N2 H2A 1.00900(5) . ?
N3 C10 1.3377(5) . ?
N3 C14 1.3412(7) . ?
C1 C2 1.3713(5) . ?
C1 C9 1.4690(5) . ?
C2 C3 1.4683(5) . ?
C3 C4 1.3995(5) . ?
C3 C8 1.4056(4) . ?
C4 C5 1.3919(6) . ?
C4 H4 1.08300(5) . ?
C5 C6 1.3947(6) . ?
C5 H5 1.08300(5) . ?
C6 C7 1.3947(5) . ?
C6 H6 1.08300(6) . ?
C7 C8 1.3871(6) . ?
C7 H7 1.08300(5) . ?
C10 C11 1.3991(5) . ?
C11 C12 1.3867(6) . ?
C11 H11 1.08300(5) . ?
C12 C13 1.3940(7) . ?
C12 H12 1.08300(6) . ?
C13 C14 1.3914(7) . ?
C13 H13 1.08300(5) . ?
C14 H14 1.08300(5) . ?
C15 H15A 1.05900(5) . ?
C15 H15B 1.05900(6) . ?
C15 H15C 1.05900(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 119.059(18) . . ?
O2 S1 N1 108.168(17) . . ?
O1 S1 N1 108.275(18) . . ?
O2 S1 C8 109.851(18) . . ?
O1 S1 C8 108.465(17) . . ?
N1 S1 C8 101.601(15) . . ?
C2 O3 H3A 102.7(6) . . ?
C1 N1 C15 115.72(3) . . ?
C1 N1 S1 112.75(2) . . ?
C15 N1 S1 115.16(3) . . ?
C9 N2 C10 128.88(3) . . ?
C9 N2 H2A 114.00(19) . . ?
C10 N2 H2A 116.0(2) . . ?
C10 N3 C14 117.50(4) . . ?
C2 C1 N1 121.20(3) . . ?
C2 C1 C9 120.75(3) . . ?
N1 C1 C9 118.04(3) . . ?
O3 C2 C1 122.59(4) . . ?
O3 C2 C3 115.37(3) . . ?
C1 C2 C3 122.04(3) . . ?
C4 C3 C8 118.09(4) . . ?
C4 C3 C2 121.42(3) . . ?
C8 C3 C2 120.47(3) . . ?
C5 C4 C3 119.80(3) . . ?
C5 C4 H4 122.2(3) . . ?
C3 C4 H4 117.9(2) . . ?
C4 C5 C6 120.95(3) . . ?
C4 C5 H5 118.5(3) . . ?
C6 C5 H5 120.6(3) . . ?
C5 C6 C7 120.28(4) . . ?
C5 C6 H6 121.5(4) . . ?
C7 C6 H6 118.0(4) . . ?
C8 C7 C6 118.19(3) . . ?
C8 C7 H7 119.6(3) . . ?
C6 C7 H7 122.0(3) . . ?
C7 C8 C3 122.65(3) . . ?
C7 C8 S1 120.92(2) . . ?
C3 C8 S1 116.40(3) . . ?
O4 C9 N2 124.14(4) . . ?
O4 C9 C1 120.53(3) . . ?
N2 C9 C1 115.33(3) . . ?
N3 C10 C11 123.68(4) . . ?
N3 C10 N2 112.44(3) . . ?
C11 C10 N2 123.88(3) . . ?
C12 C11 C10 117.60(4) . . ?
C12 C11 H11 120.2(3) . . ?
C10 C11 H11 122.2(3) . . ?
C11 C12 C13 119.85(4) . . ?
C11 C12 H12 120.8(2) . . ?
C13 C12 H12 119.35(19) . . ?
C14 C13 C12 117.79(4) . . ?
C14 C13 H13 118.6(3) . . ?
C12 C13 H13 123.5(3) . . ?
N3 C14 C13 123.58(4) . . ?
N3 C14 H14 115.3(3) . . ?
C13 C14 H14 121.1(3) . . ?
N1 C15 H15A 108.1(2) . . ?
N1 C15 H15B 106.4(5) . . ?
H15A C15 H15B 111.0(6) . . ?
N1 C15 H15C 108.4(5) . . ?
H15A C15 H15C 110.1(6) . . ?
H15B C15 H15C 112.7(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C1 -170.63(3) . . . . ?
O1 S1 N1 C1 59.08(3) . . . . ?
C8 S1 N1 C1 -55.02(3) . . . . ?
O2 S1 N1 C15 -34.82(3) . . . . ?
O1 S1 N1 C15 -165.12(2) . . . . ?
C8 S1 N1 C15 80.78(3) . . . . ?
C15 N1 C1 C2 -95.81(4) . . . . ?
S1 N1 C1 C2 39.72(4) . . . . ?
C15 N1 C1 C9 84.72(4) . . . . ?
S1 N1 C1 C9 -139.74(3) . . . . ?
N1 C1 C2 O3 -179.29(3) . . . . ?
C9 C1 C2 O3 0.16(5) . . . . ?
N1 C1 C2 C3 1.03(5) . . . . ?
C9 C1 C2 C3 -179.53(3) . . . . ?
O3 C2 C3 C4 -19.89(5) . . . . ?
C1 C2 C3 C4 159.82(3) . . . . ?
O3 C2 C3 C8 161.78(3) . . . . ?
C1 C2 C3 C8 -18.51(5) . . . . ?
C8 C3 C4 C5 1.64(5) . . . . ?
C2 C3 C4 C5 -176.72(3) . . . . ?
C3 C4 C5 C6 0.29(5) . . . . ?
C4 C5 C6 C7 -1.47(6) . . . . ?
C5 C6 C7 C8 0.63(6) . . . . ?
C6 C7 C8 C3 1.39(5) . . . . ?
C6 C7 C8 S1 -176.30(3) . . . . ?
C4 C3 C8 C7 -2.53(5) . . . . ?
C2 C3 C8 C7 175.84(3) . . . . ?
C4 C3 C8 S1 175.26(2) . . . . ?
C2 C3 C8 S1 -6.36(4) . . . . ?
O2 S1 C8 C7 -28.14(3) . . . . ?
O1 S1 C8 C7 103.54(3) . . . . ?
N1 S1 C8 C7 -142.51(3) . . . . ?
O2 S1 C8 C3 154.02(3) . . . . ?
O1 S1 C8 C3 -74.30(3) . . . . ?
N1 S1 C8 C3 39.66(3) . . . . ?
C10 N2 C9 O4 -4.06(6) . . . . ?
C10 N2 C9 C1 176.61(3) . . . . ?
C2 C1 C9 O4 6.14(5) . . . . ?
N1 C1 C9 O4 -174.39(3) . . . . ?
C2 C1 C9 N2 -174.50(3) . . . . ?
N1 C1 C9 N2 4.96(4) . . . . ?
C14 N3 C10 C11 -0.03(6) . . . . ?
C14 N3 C10 N2 179.18(4) . . . . ?
C9 N2 C10 N3 176.78(4) . . . . ?
C9 N2 C10 C11 -4.01(6) . . . . ?
N3 C10 C11 C12 0.03(6) . . . . ?
N2 C10 C11 C12 -179.09(3) . . . . ?
C10 C11 C12 C13 -0.09(6) . . . . ?
C11 C12 C13 C14 0.14(7) . . . . ?
C10 N3 C14 C13 0.09(7) . . . . ?
C12 C13 C14 N3 -0.14(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 1.0090(1) 2.218(4) 3.0018(4) 133.3(4) 3_565
O3 H3A O4 0.9670(1) 1.662(5) 2.5641(5) 153.6(9) .
C11 H11 O4 1.0830(1) 2.247(5) 2.8929(6) 116.2(3) .
C14 H14 O4 1.0830(1) 2.5613(19) 3.6303(5) 169.0(7) 2_454
C15 H15A O1 1.0590(1) 2.5071(18) 3.4544(5) 148.5(2) 1_455

_refine_diff_density_max         0.829
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.084



####################################################################### 
# 
# 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_xprep
_database_code_depnum_ccdc_archive 'CCDC 1474337'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Saccharin
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H5 N O3 S'
_chemical_formula_weight         183.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.444
_cell_length_b                   6.921
_cell_length_c                   11.684
_cell_angle_alpha                90
_cell_angle_beta                 103.05
_cell_angle_gamma                90
_cell_volume                     743.9
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      65.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.394
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Agilent Technologies SuperNova CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8523
_diffrn_reflns_av_unetI/netI     0.0067
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.445
_diffrn_reflns_theta_max         52.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             8523
_reflns_number_gt                7584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.0455P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    fixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8523
_refine_ls_number_parameters     129
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.28987(2) 0.77144(2) 0.15420(2) 0.01027(2) Uani 1 1 d . . . . .
O1 O 0.25443(3) 0.82939(4) 0.26221(2) 0.01632(4) Uani 1 1 d . . . . .
O2 O 0.41890(3) 0.65838(5) 0.16197(3) 0.01752(4) Uani 1 1 d . . . . .
N1 N 0.14903(3) 0.65741(3) 0.06912(2) 0.01205(3) Uani 1 1 d D . . . .
O3 O -0.02099(3) 0.69215(4) -0.10461(2) 0.01256(3) Uani 1 1 d . . . . .
C1 C 0.27741(3) 0.96566(4) 0.05556(2) 0.01061(3) Uani 1 1 d . . . . .
C2 C 0.36401(3) 1.12964(5) 0.06738(2) 0.01453(4) Uani 1 1 d D . . . .
C3 C 0.33115(3) 1.26511(4) -0.02367(3) 0.01571(5) Uani 1 1 d D . . . .
C4 C 0.21656(4) 1.23591(4) -0.12141(2) 0.01489(4) Uani 1 1 d D . . . .
C5 C 0.12991(3) 1.07084(4) -0.13055(2) 0.01234(4) Uani 1 1 d D . . . .
C6 C 0.16221(3) 0.93583(4) -0.04052(2) 0.00969(3) Uani 1 1 d . . . . .
C7 C 0.08497(3) 0.75203(4) -0.03267(2) 0.00959(3) Uani 1 1 d . . . . .
H1A H 0.11314(9) 0.52481(5) 0.08468(11) 0.030(2) Uiso 1 1 d D . . . .
H2 H 0.44898(6) 1.1535(3) 0.14547(4) 0.035(3) Uiso 1 1 d D . . . .
H3 H 0.39491(6) 1.39452(6) -0.02601(18) 0.038(3) Uiso 1 1 d D . . . .
H4 H 0.1908(6) 1.34024(7) -0.19215(4) 0.030(2) Uiso 1 1 d D . . . .
H5 H 0.03949(6) 1.0462(3) -0.20459(4) 0.025(2) 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 1.4336(3) . ?
S1 O1 1.4340(3) . ?
S1 N1 1.6682(2) . ?
S1 C1 1.7572(3) . ?
N1 C7 1.3726(3) . ?
O3 C7 1.2247(3) . ?
C1 C2 1.3874(4) . ?
C1 C6 1.3909(4) . ?
C2 C3 1.3993(4) . ?
C3 C4 1.3992(5) . ?
C4 C5 1.3952(4) . ?
C5 C6 1.3885(4) . ?
C6 C7 1.4795(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 117.442(18) . . ?
O2 S1 N1 109.356(16) . . ?
O1 S1 N1 110.095(16) . . ?
O2 S1 C1 112.902(16) . . ?
O1 S1 C1 111.645(15) . . ?
N1 S1 C1 92.570(12) . . ?
C7 N1 S1 115.254(17) . . ?
C2 C1 C6 122.54(2) . . ?
C2 C1 S1 127.58(2) . . ?
C6 C1 S1 109.877(19) . . ?
C1 C2 C3 116.61(2) . . ?
C4 C3 C2 121.43(2) . . ?
C5 C4 C3 120.86(2) . . ?
C6 C5 C4 117.93(2) . . ?
C5 C6 C1 120.63(2) . . ?
C5 C6 C7 126.77(2) . . ?
C1 C6 C7 112.60(2) . . ?
O3 C7 N1 124.41(2) . . ?
O3 C7 C6 125.89(2) . . ?
N1 C7 C6 109.69(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C7 -116.14(2) . . . . ?
O1 S1 N1 C7 113.42(2) . . . . ?
C1 S1 N1 C7 -0.75(2) . . . . ?
O2 S1 C1 C2 -68.24(3) . . . . ?
O1 S1 C1 C2 66.66(3) . . . . ?
N1 S1 C1 C2 179.48(3) . . . . ?
O2 S1 C1 C6 112.86(2) . . . . ?
O1 S1 C1 C6 -112.24(2) . . . . ?
N1 S1 C1 C6 0.58(2) . . . . ?
C6 C1 C2 C3 -0.76(4) . . . . ?
S1 C1 C2 C3 -179.53(2) . . . . ?
C1 C2 C3 C4 0.05(5) . . . . ?
C2 C3 C4 C5 0.74(5) . . . . ?
C3 C4 C5 C6 -0.81(5) . . . . ?
C4 C5 C6 C1 0.12(4) . . . . ?
C4 C5 C6 C7 -179.95(3) . . . . ?
C2 C1 C6 C5 0.69(4) . . . . ?
S1 C1 C6 C5 179.65(2) . . . . ?
C2 C1 C6 C7 -179.25(3) . . . . ?
S1 C1 C6 C7 -0.29(3) . . . . ?
S1 N1 C7 O3 -178.65(2) . . . . ?
S1 N1 C7 C6 0.70(3) . . . . ?
C5 C6 C7 O3 -0.84(5) . . . . ?
C1 C6 C7 O3 179.10(3) . . . . ?
C5 C6 C7 N1 179.83(3) . . . . ?
C1 C6 C7 N1 -0.23(3) . . . . ?

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.082



