# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1451204'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT222_shelxl              
;
PROBLEM: Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        7.9 Ratio 
RESPONSE: This hydrogen atom is involved in a moderate strength hydrogen
bond.
;
# end Validation Reply Form



_audit_creation_method           SHELXL-97
_chemical_name_systematic        'piracetam gallic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 O5, C6 H10 N2 O2'
_chemical_formula_sum            'C13 H16 N2 O7'
_chemical_formula_weight         312.28

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'

_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                   12.554(2)
_cell_length_b                   8.8499(15)
_cell_length_c                   12.6253(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.988(5)
_cell_angle_gamma                90.00
_cell_volume                     1361.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10617
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4798
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Rigaku R-AXIS RAPID IP Image Plate diffractometer'
_diffrn_measurement_method       'Image Plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10236
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_sigmaI/netI    0.0888
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3044
_reflns_number_gt                1684
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.3928P] 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         3044
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1633
_refine_ls_wR_factor_gt          0.1176
_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
H4 H 0.108(2) -0.169(3) 0.739(2) 0.014(7) Uiso 1 1 d . . .
H5 H -0.008(2) -0.236(4) 0.414(2) 0.021(8) Uiso 1 1 d . . .
H10 H 0.567(3) 0.311(4) -0.187(2) 0.033(9) Uiso 1 1 d . . .
H9 H 0.549(3) 0.175(4) 0.102(3) 0.041(10) Uiso 1 1 d . . .
H7 H 0.427(3) 0.164(4) -0.065(3) 0.042(10) Uiso 1 1 d . . .
H12 H 0.698(2) 0.113(4) -0.237(3) 0.028(9) Uiso 1 1 d . . .
H11 H 0.491(3) 0.159(4) -0.221(3) 0.046(10) Uiso 1 1 d . . .
H8 H 0.614(3) 0.318(4) 0.070(2) 0.031(9) Uiso 1 1 d . . .
H14 H 0.787(3) -0.105(5) -0.290(3) 0.054(12) Uiso 1 1 d . . .
H16 H -0.169(4) -0.434(5) 0.540(3) 0.078(15) Uiso 1 1 d . . .
H13 H 0.791(3) 0.074(4) -0.124(3) 0.056(12) Uiso 1 1 d . . .
H6 H 0.454(3) 0.353(5) -0.068(3) 0.072(14) Uiso 1 1 d . . .
H1 H 0.068(3) -0.105(4) 0.298(3) 0.052(11) Uiso 1 1 d . . .
H2 H 0.313(4) 0.129(6) 0.570(4) 0.091(17) Uiso 1 1 d . . .
H15 H 0.746(4) -0.269(6) -0.256(3) 0.074(15) Uiso 1 1 d . . .
H3 H 0.272(4) -0.033(6) 0.803(4) 0.111(19) Uiso 1 1 d . . .
O2 O 0.27514(17) 0.0035(3) 0.72932(17) 0.0259(5) Uani 1 1 d . . .
O6 O -0.05016(18) -0.3592(3) 0.69751(16) 0.0290(6) Uani 1 1 d . . .
O5 O -0.11904(19) -0.3692(3) 0.51734(17) 0.0329(6) Uani 1 1 d . . .
O3 O 0.28202(18) 0.0584(3) 0.51496(18) 0.0281(6) Uani 1 1 d . . .
O4 O 0.13273(18) -0.0599(3) 0.34924(16) 0.0259(5) Uani 1 1 d . . .
C10 C 0.2021(2) -0.0292(4) 0.5398(2) 0.0228(7) Uani 1 1 d . . .
C7 C 0.0373(2) -0.2180(4) 0.5803(2) 0.0230(7) Uani 1 1 d . . .
C9 C 0.1956(2) -0.0604(4) 0.6462(2) 0.0234(7) Uani 1 1 d . . .
C5 C 0.1240(3) -0.0951(4) 0.4535(2) 0.0243(7) Uani 1 1 d . . .
C6 C 0.0433(3) -0.1898(4) 0.4732(2) 0.0237(7) Uani 1 1 d . . .
C8 C 0.1129(2) -0.1504(4) 0.6670(3) 0.0229(7) Uani 1 1 d . . .
C11 C -0.0467(3) -0.3197(4) 0.6050(2) 0.0246(7) Uani 1 1 d . . .
O1 O 0.74001(17) 0.0646(3) 0.06840(16) 0.0268(5) Uani 1 1 d . . .
O7 O 0.64457(17) -0.1829(2) -0.12597(16) 0.0266(5) Uani 1 1 d . . .
N1 N 0.6389(2) 0.1281(3) -0.10246(19) 0.0232(6) Uani 1 1 d . . .
C13 C 0.6971(2) -0.1076(4) -0.1789(2) 0.0233(7) Uani 1 1 d . . .
N2 N 0.7492(2) -0.1665(4) -0.2495(2) 0.0293(7) Uani 1 1 d . . .
C4 C 0.6600(2) 0.1302(4) 0.0061(2) 0.0238(7) Uani 1 1 d . . .
C1 C 0.5419(3) 0.2179(4) -0.1555(3) 0.0282(8) Uani 1 1 d . . .
C2 C 0.4859(3) 0.2489(5) -0.0614(3) 0.0322(8) Uani 1 1 d . . .
C3 C 0.5763(3) 0.2266(4) 0.0417(3) 0.0286(8) Uani 1 1 d . . .
C12 C 0.7115(3) 0.0626(4) -0.1631(3) 0.0264(7) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C9 1.382(3) . ?
O2 H3 0.99(5) . ?
O6 C11 1.230(3) . ?
O5 C11 1.325(4) . ?
O5 H16 0.94(5) . ?
O3 C10 1.363(4) . ?
O3 H2 0.94(5) . ?
O4 C5 1.382(3) . ?
O4 H1 0.99(4) . ?
C10 C9 1.394(4) . ?
C10 C5 1.404(4) . ?
C7 C6 1.395(4) . ?
C7 C8 1.399(4) . ?
C7 C11 1.476(4) . ?
C9 C8 1.383(4) . ?
C5 C6 1.383(4) . ?
C6 H5 0.95(3) . ?
C8 H4 0.94(3) . ?
O1 C4 1.258(3) . ?
O7 C13 1.240(4) . ?
N1 C4 1.331(4) . ?
N1 C12 1.447(4) . ?
N1 C1 1.472(4) . ?
C13 N2 1.333(4) . ?
C13 C12 1.524(5) . ?
N2 H14 0.95(4) . ?
N2 H15 0.91(5) . ?
C4 C3 1.505(4) . ?
C1 C2 1.544(4) . ?
C1 H10 0.99(3) . ?
C1 H11 1.05(4) . ?
C2 C3 1.519(5) . ?
C2 H7 1.05(4) . ?
C2 H6 1.00(5) . ?
C3 H9 1.01(3) . ?
C3 H8 0.96(3) . ?
C12 H12 1.01(3) . ?
C12 H13 1.01(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
C9 O2 H3 113(3) . . ?
C11 O5 H16 109(3) . . ?
C10 O3 H2 114(3) . . ?
C5 O4 H1 107(2) . . ?
O3 C10 C9 123.5(3) . . ?
O3 C10 C5 118.2(3) . . ?
C9 C10 C5 118.3(3) . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 C11 121.5(3) . . ?
C8 C7 C11 118.7(3) . . ?
O2 C9 C8 121.9(3) . . ?
O2 C9 C10 116.8(3) . . ?
C8 C9 C10 121.2(3) . . ?
O4 C5 C6 122.5(3) . . ?
O4 C5 C10 116.4(3) . . ?
C6 C5 C10 121.1(3) . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H5 120.3(17) . . ?
C7 C6 H5 119.9(17) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H4 121.0(17) . . ?
C7 C8 H4 119.2(17) . . ?
O6 C11 O5 121.7(3) . . ?
O6 C11 C7 124.4(3) . . ?
O5 C11 C7 113.9(3) . . ?
C4 N1 C12 123.8(3) . . ?
C4 N1 C1 113.4(2) . . ?
C12 N1 C1 122.3(2) . . ?
O7 C13 N2 124.1(3) . . ?
O7 C13 C12 121.5(3) . . ?
N2 C13 C12 114.3(3) . . ?
C13 N2 H14 122(2) . . ?
C13 N2 H15 116(3) . . ?
H14 N2 H15 122(4) . . ?
O1 C4 N1 124.6(3) . . ?
O1 C4 C3 125.8(3) . . ?
N1 C4 C3 109.6(3) . . ?
N1 C1 C2 103.1(2) . . ?
N1 C1 H10 108.8(19) . . ?
C2 C1 H10 113.7(19) . . ?
N1 C1 H11 111(2) . . ?
C2 C1 H11 113.2(19) . . ?
H10 C1 H11 107(3) . . ?
C3 C2 C1 104.6(3) . . ?
C3 C2 H7 108.6(18) . . ?
C1 C2 H7 106.5(18) . . ?
C3 C2 H6 113(2) . . ?
C1 C2 H6 111(2) . . ?
H7 C2 H6 113(3) . . ?
C4 C3 C2 104.4(3) . . ?
C4 C3 H9 111(2) . . ?
C2 C3 H9 113(2) . . ?
C4 C3 H8 106(2) . . ?
C2 C3 H8 114.1(19) . . ?
H9 C3 H8 109(3) . . ?
N1 C12 C13 113.3(3) . . ?
N1 C12 H12 108.9(18) . . ?
C13 C12 H12 109.2(18) . . ?
N1 C12 H13 112(2) . . ?
C13 C12 H13 104(2) . . ?
H12 C12 H13 110(3) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1451205'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT355_shelxl              
;
PROBLEM: Long    O-H (X0.82,N0.98A)  O4     -   H8     ..       1.22 Ang.  
RESPONSE: The hydrogen atom positions are unreliably determined due to the
small, weakly diffracting crystals, the presence of large solvent voids, 
and the fact that it is involved in a moderate strength hydrogen bond.
;
_vrf_PLAT306_shelxl              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......         O6 Check 
RESPONSE: It was not possible to identify the hydrogen atom positions due 
to the presence of disordered solvent molecules within the voids.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Gallic acid monohydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C7 H6 O5), (H2O)'
_chemical_formula_sum            'C7 H8 O6'
_chemical_formula_weight         188.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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/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                   3.6803(3)
_cell_length_b                   27.7240(19)
_cell_length_c                   9.3579(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.397(3)
_cell_angle_gamma                90.00
_cell_volume                     952.00(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12382
_cell_measurement_theta_min      1
_cell_measurement_theta_max      28.05

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8303
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12141
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         28.09
_reflns_number_total             2115
_reflns_number_gt                929
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          SQUEEZE

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.091 0.000 0.000 160 60 ' '
2 -0.083 0.500 0.500 160 60 ' '
_platon_squeeze_details          
;
;

_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)+(0.0792P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2115
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1636
_refine_ls_wR_factor_gt          0.1474
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
O6 O 0.7997(10) 0.15068(9) 0.9784(3) 0.0947(11) Uani 1 1 d . . .
O1 O 0.8380(6) 0.20805(7) 1.7071(2) 0.0405(6) Uani 1 1 d . . .
H2 H 0.699(10) 0.2317(11) 1.690(3) 0.061 Uiso 1 1 d . . .
C5 C 0.8893(7) 0.20673(9) 1.4536(3) 0.0291(7) Uani 1 1 d . . .
O3 O 0.9240(6) 0.20792(7) 1.2061(2) 0.0455(6) Uani 1 1 d . . .
H5 H 0.919(9) 0.1883(12) 1.125(4) 0.068 Uiso 1 1 d . . .
O2 O 0.7518(6) 0.25248(6) 1.4476(2) 0.0386(6) Uani 1 1 d . . .
H1 H 0.707(9) 0.2615(10) 1.347(4) 0.058 Uiso 1 1 d . . .
O4 O 1.3938(7) 0.04307(8) 1.3737(3) 0.0650(8) Uani 1 1 d . . .
H8 H 1.434(10) -0.0006(14) 1.380(4) 0.097 Uiso 1 1 d . . .
O5 O 1.3369(7) 0.04436(8) 1.6098(3) 0.0700(8) Uani 1 1 d . . .
C3 C 1.0679(8) 0.13792(10) 1.5968(4) 0.0387(8) Uani 1 1 d . . .
H3 H 1.107(7) 0.1228(10) 1.699(3) 0.046 Uiso 1 1 d . . .
C6 C 0.9803(8) 0.18244(10) 1.3321(3) 0.0329(7) Uani 1 1 d . . .
C4 C 0.9318(8) 0.18450(9) 1.5860(3) 0.0300(7) Uani 1 1 d . . .
C7 C 1.1153(8) 0.13628(10) 1.3424(4) 0.0389(8) Uani 1 1 d . . .
H4 H 1.230(8) 0.1226(10) 1.274(3) 0.047 Uiso 1 1 d . . .
C2 C 1.1590(8) 0.11390(10) 1.4753(3) 0.0363(8) Uani 1 1 d . . .
C1 C 1.3015(9) 0.06408(11) 1.4847(4) 0.0502(10) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.374(3) . ?
O1 H2 0.84(3) . ?
C5 O2 1.365(3) . ?
C5 C4 1.382(4) . ?
C5 C6 1.385(4) . ?
O3 C6 1.376(3) . ?
O3 H5 0.93(3) . ?
O2 H1 0.98(3) . ?
O4 C1 1.260(4) . ?
O4 H8 1.22(4) . ?
O5 C1 1.290(4) . ?
C3 C2 1.381(4) . ?
C3 C4 1.386(4) . ?
C3 H3 1.04(3) . ?
C6 C7 1.374(4) . ?
C7 C2 1.388(4) . ?
C7 H4 0.88(3) . ?
C2 C1 1.477(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
C4 O1 H2 114(2) . . ?
O2 C5 C4 117.8(3) . . ?
O2 C5 C6 122.0(3) . . ?
C4 C5 C6 120.1(2) . . ?
C6 O3 H5 113(2) . . ?
C5 O2 H1 108.3(18) . . ?
C1 O4 H8 117.4(19) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 122.3(16) . . ?
C4 C3 H3 117.7(16) . . ?
C7 C6 O3 124.6(3) . . ?
C7 C6 C5 120.3(3) . . ?
O3 C6 C5 115.1(2) . . ?
O1 C4 C5 120.6(2) . . ?
O1 C4 C3 119.7(3) . . ?
C5 C4 C3 119.7(3) . . ?
C6 C7 C2 119.7(3) . . ?
C6 C7 H4 123(2) . . ?
C2 C7 H4 115(2) . . ?
C3 C2 C7 120.2(3) . . ?
C3 C2 C1 120.6(3) . . ?
C7 C2 C1 119.2(3) . . ?
O4 C1 O5 122.5(3) . . ?
O4 C1 C2 120.0(3) . . ?
O5 C1 C2 117.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.918
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1451206'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        piroxicam
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3 O4 S'
_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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.8557(3)
_cell_length_b                   10.1043(4)
_cell_length_c                   10.4713(5)
_cell_angle_alpha                80.602(2)
_cell_angle_beta                 68.952(2)
_cell_angle_gamma                69.742(2)
_cell_volume                     727.01(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16529
_cell_measurement_theta_min      1
_cell_measurement_theta_max      61.15

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8667
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16541
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         30.52
_reflns_number_total             4375
_reflns_number_gt                3102
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (2009)'
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0477P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4375
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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
H6 H 0.388(2) 0.4573(18) 0.3851(19) 0.019(5) Uiso 1 1 d . . .
H2 H 0.250(3) 0.607(2) 1.008(2) 0.028(5) Uiso 1 1 d . . .
H9 H 0.177(3) 0.213(2) 0.417(2) 0.035(6) Uiso 1 1 d . . .
H3 H 0.371(3) 0.3710(19) 1.076(2) 0.027(5) Uiso 1 1 d . . .
H11 H 0.207(2) -0.2751(17) 0.3103(18) 0.013(4) Uiso 1 1 d . . .
H10 H 0.244(2) -0.1463(17) 0.4669(19) 0.016(4) Uiso 1 1 d . . .
H4 H 0.402(3) 0.1877(18) 0.9550(19) 0.020(5) Uiso 1 1 d . . .
H1 H 0.138(3) 0.654(2) 0.815(2) 0.027(5) Uiso 1 1 d . . .
H7 H 0.478(3) 0.2863(19) 0.384(2) 0.025(5) Uiso 1 1 d . . .
H12 H 0.131(3) -0.1489(19) 0.114(2) 0.026(5) Uiso 1 1 d . . .
H5 H 0.511(3) 0.3797(18) 0.4807(19) 0.026(5) Uiso 1 1 d . . .
H8 H 0.314(3) 0.011(2) 0.750(3) 0.057(8) Uiso 1 1 d . . .
H13 H 0.107(3) 0.0927(18) 0.0771(19) 0.020(5) Uiso 1 1 d . . .
S1 S 0.10345(5) 0.48134(4) 0.64541(4) 0.01435(10) Uani 1 1 d . . .
O1 O 0.30517(15) -0.02774(11) 0.60096(12) 0.0168(2) Uani 1 1 d . . .
O2 O 0.31423(17) 0.06435(12) 0.80968(12) 0.0191(2) Uani 1 1 d . . .
N1 N 0.24278(17) 0.34877(12) 0.54512(13) 0.0135(3) Uani 1 1 d . . .
O3 O -0.08463(15) 0.46633(11) 0.70252(12) 0.0183(2) Uani 1 1 d . . .
O4 O 0.12639(16) 0.60977(11) 0.57048(12) 0.0187(2) Uani 1 1 d . . .
N2 N 0.21808(19) 0.13009(14) 0.43372(14) 0.0148(3) Uani 1 1 d . . .
C8 C 0.2657(2) 0.21239(15) 0.61662(16) 0.0138(3) Uani 1 1 d . . .
C12 C 0.2171(2) -0.10081(16) 0.38256(17) 0.0168(3) Uani 1 1 d . . .
C10 C 0.2648(2) 0.09536(16) 0.54980(16) 0.0144(3) Uani 1 1 d . . .
C7 C 0.2883(2) 0.19138(16) 0.74243(16) 0.0151(3) Uani 1 1 d . . .
N3 N 0.1578(2) 0.11253(14) 0.24002(14) 0.0185(3) Uani 1 1 d . . .
C11 C 0.1989(2) 0.04247(16) 0.35110(16) 0.0148(3) Uani 1 1 d . . .
C1 C 0.2027(2) 0.44796(16) 0.77797(16) 0.0154(3) Uani 1 1 d . . .
C6 C 0.2792(2) 0.30656(16) 0.81758(16) 0.0152(3) Uani 1 1 d . . .
C3 C 0.2576(2) 0.52844(18) 0.95769(18) 0.0214(3) Uani 1 1 d . . .
C2 C 0.1932(2) 0.55976(17) 0.84556(17) 0.0184(3) Uani 1 1 d . . .
C4 C 0.3314(2) 0.38885(19) 0.99996(18) 0.0206(3) Uani 1 1 d . . .
C14 C 0.1520(2) -0.10403(18) 0.17690(18) 0.0206(3) Uani 1 1 d . . .
C15 C 0.1938(2) -0.17406(17) 0.29239(18) 0.0189(3) Uani 1 1 d . . .
C5 C 0.3444(2) 0.27843(18) 0.93037(17) 0.0182(3) Uani 1 1 d . . .
C9 C 0.4210(2) 0.36762(17) 0.44048(18) 0.0178(3) Uani 1 1 d . . .
C13 C 0.1345(2) 0.03881(18) 0.15551(18) 0.0203(3) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4334(11) . ?
S1 O4 1.4353(11) . ?
S1 N1 1.6473(13) . ?
S1 C1 1.7581(16) . ?
O1 C10 1.2514(18) . ?
O2 C7 1.3460(18) . ?
O2 H8 0.88(3) . ?
N1 C8 1.4422(18) . ?
N1 C9 1.487(2) . ?
N2 C10 1.352(2) . ?
N2 C11 1.4112(19) . ?
N2 H9 0.805(19) . ?
C8 C7 1.365(2) . ?
C8 C10 1.472(2) . ?
C12 C15 1.386(2) . ?
C12 C11 1.400(2) . ?
C12 H10 0.985(18) . ?
C7 C6 1.477(2) . ?
N3 C13 1.341(2) . ?
N3 C11 1.342(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.402(2) . ?
C6 C5 1.400(2) . ?
C3 C2 1.389(2) . ?
C3 C4 1.391(2) . ?
C3 H2 1.00(2) . ?
C2 H1 0.958(18) . ?
C4 C5 1.385(2) . ?
C4 H3 0.92(2) . ?
C14 C15 1.384(2) . ?
C14 C13 1.390(2) . ?
C14 H12 0.95(2) . ?
C15 H11 0.982(16) . ?
C5 H4 0.912(17) . ?
C9 H6 0.998(17) . ?
C9 H7 0.970(19) . ?
C9 H5 0.989(19) . ?
C13 H13 0.959(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 119.23(7) . . ?
O3 S1 N1 107.93(7) . . ?
O4 S1 N1 108.14(7) . . ?
O3 S1 C1 107.92(7) . . ?
O4 S1 C1 109.67(7) . . ?
N1 S1 C1 102.69(7) . . ?
C7 O2 H8 101.4(15) . . ?
C8 N1 C9 115.15(11) . . ?
C8 N1 S1 113.57(10) . . ?
C9 N1 S1 116.65(10) . . ?
C10 N2 C11 128.85(14) . . ?
C10 N2 H9 115.7(15) . . ?
C11 N2 H9 114.5(15) . . ?
C7 C8 N1 121.33(13) . . ?
C7 C8 C10 120.58(13) . . ?
N1 C8 C10 118.10(13) . . ?
C15 C12 C11 117.74(15) . . ?
C15 C12 H10 122.0(10) . . ?
C11 C12 H10 120.3(10) . . ?
O1 C10 N2 123.70(14) . . ?
O1 C10 C8 120.14(14) . . ?
N2 C10 C8 116.16(13) . . ?
O2 C7 C8 122.36(14) . . ?
O2 C7 C6 114.75(14) . . ?
C8 C7 C6 122.86(14) . . ?
C13 N3 C11 117.03(14) . . ?
N3 C11 C12 123.70(15) . . ?
N3 C11 N2 112.40(13) . . ?
C12 C11 N2 123.89(14) . . ?
C2 C1 C6 122.12(15) . . ?
C2 C1 S1 120.22(12) . . ?
C6 C1 S1 117.54(12) . . ?
C5 C6 C1 118.20(15) . . ?
C5 C6 C7 121.41(14) . . ?
C1 C6 C7 120.39(14) . . ?
C2 C3 C4 120.48(15) . . ?
C2 C3 H2 119.6(11) . . ?
C4 C3 H2 120.0(11) . . ?
C3 C2 C1 118.30(15) . . ?
C3 C2 H1 123.2(12) . . ?
C1 C2 H1 118.5(12) . . ?
C5 C4 C3 120.85(16) . . ?
C5 C4 H3 120.4(12) . . ?
C3 C4 H3 118.7(12) . . ?
C15 C14 C13 118.38(16) . . ?
C15 C14 H12 122.7(11) . . ?
C13 C14 H12 118.9(11) . . ?
C14 C15 C12 119.54(15) . . ?
C14 C15 H11 120.3(10) . . ?
C12 C15 H11 120.1(10) . . ?
C4 C5 C6 120.03(16) . . ?
C4 C5 H4 119.7(11) . . ?
C6 C5 H4 120.1(12) . . ?
N1 C9 H6 109.7(10) . . ?
N1 C9 H7 106.3(11) . . ?
H6 C9 H7 111.2(15) . . ?
N1 C9 H5 113.2(11) . . ?
H6 C9 H5 104.0(13) . . ?
H7 C9 H5 112.6(15) . . ?
N3 C13 C14 123.60(16) . . ?
N3 C13 H13 114.3(11) . . ?
C14 C13 H13 122.1(11) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        30.52
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1451207'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_shelxl              
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.947 Note  
RESPONSE: The crystals were small and weakly diffracting
;
_vrf_PLAT201_shelxl              
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          1 Report
RESPONSE: There is some disorder in the crystal structure which could not
be modelled.  One atom was therefore refined only isotropically as
an anisotropic refinement gave unreasonable parameters.
;
_vrf_PLAT910_shelxl              
;
PROBLEM: Missing # of FCF Reflection(s) Below Th(Min) ...         22 Report
RESPONSE: The crystals were small and weakly diffracting.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_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'

_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                   12.6899(9)
_cell_length_b                   14.6928(9)
_cell_length_c                   20.5097(16)
_cell_angle_alpha                84.866(2)
_cell_angle_beta                 74.669(3)
_cell_angle_gamma                84.683(2)
_cell_volume                     3663.7(4)
_cell_formula_units_Z            10
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19223
_cell_measurement_theta_min      6.08
_cell_measurement_theta_max      49.77

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1720
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7733
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40126
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_sigmaI/netI    0.1061
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         24.71
_reflns_number_total             11817
_reflns_number_gt                6294
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

The crystals were small and weakly diffracting and these were the best data 
that were obtainable.  Atom C75, when freely refined, resulted in an 
anomolous anisotropic displacement parameter.  This is likely to be due to
some disorder of one of the zwitterionic piroxicam molecules, where it can
potentially sit in two possible orientations along a channel - there is
some evidence for this in the residual electron density map, where a 
secondary SO2 group can be identified and modelled at approximately 10%
disorder.  However, it is not possible to resolve the atom positions of the
remainder of the disordered molecule as the two positions, and the relatively
low occupancy make it impossible to distinguish them.  The model adopted was
therefore one with only one position and with atom C75 refined only 
isotropically.
;

_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)+(0.1655P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11817
_refine_ls_number_parameters     1040
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1569
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.2819
_refine_ls_wR_factor_gt          0.2094
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
C75 C 0.0327(6) 0.1883(5) 0.6583(4) 0.0470(19) Uiso 1 1 d . . .
H52 H 0.0188 0.2505 0.6649 0.056 Uiso 1 1 calc R . .
S1 S 0.15559(14) 0.43375(12) 0.07259(8) 0.0331(4) Uani 1 1 d . . .
O2 O 0.0590(4) 0.4188(3) 0.1254(2) 0.0372(12) Uani 1 1 d . . .
O3 O 0.4419(4) 0.3563(3) -0.0803(2) 0.0349(11) Uani 1 1 d . . .
H60 H 0.4955 0.3639 -0.0668 0.052 Uiso 1 1 calc R . .
O4 O 0.5495(3) 0.3696(3) 0.0039(2) 0.0335(11) Uani 1 1 d . . .
N1 N 0.5431(4) 0.3553(3) 0.2048(2) 0.0286(12) Uani 1 1 d . . .
O1 O 0.1888(4) 0.5260(3) 0.0546(2) 0.0324(11) Uani 1 1 d . . .
N3 N 0.2608(4) 0.3718(4) 0.0913(2) 0.0313(13) Uani 1 1 d . . .
C6 C 0.4635(6) 0.3768(4) 0.0506(3) 0.0328(16) Uani 1 1 d . . .
C15 C 0.3506(5) 0.3606(4) -0.0281(3) 0.0291(15) Uani 1 1 d . . .
C3 C 0.7416(6) 0.4155(5) 0.1312(3) 0.0358(17) Uani 1 1 d . . .
H3 H 0.8085 0.4364 0.1064 0.043 Uiso 1 1 calc R . .
C7 C 0.3575(5) 0.3710(5) 0.0367(3) 0.0323(16) Uani 1 1 d . . .
N2 N 0.4648(4) 0.3867(4) 0.1159(2) 0.0327(13) Uani 1 1 d . . .
H5 H 0.4025 0.3936 0.1451 0.039 Uiso 1 1 calc R . .
C1 C 0.5608(5) 0.3868(4) 0.1399(3) 0.0291(15) Uani 1 1 d . . .
C5 C 0.6269(6) 0.3545(4) 0.2327(3) 0.0300(15) Uani 1 1 d . . .
H1 H 0.6164 0.3332 0.2779 0.036 Uiso 1 1 calc R . .
C4 C 0.7280(6) 0.3836(5) 0.1986(3) 0.0387(18) Uani 1 1 d . . .
H2 H 0.7848 0.3820 0.2196 0.046 Uiso 1 1 calc R . .
C13 C 0.1468(6) 0.3199(4) -0.1226(3) 0.0378(18) Uani 1 1 d . . .
H7 H 0.1460 0.2996 -0.1641 0.045 Uiso 1 1 calc R . .
C2 C 0.6577(6) 0.4164(4) 0.1013(3) 0.0371(17) Uani 1 1 d . . .
H4 H 0.6663 0.4365 0.0560 0.044 Uiso 1 1 calc R . .
C11 C 0.0492(6) 0.3801(5) -0.0169(3) 0.0369(17) Uani 1 1 d . . .
H9 H -0.0160 0.3988 0.0135 0.044 Uiso 1 1 calc R . .
C9 C 0.2480(5) 0.3563(5) -0.0456(3) 0.0318(16) Uani 1 1 d . . .
C14 C 0.2456(6) 0.3226(4) -0.1074(3) 0.0303(16) Uani 1 1 d . . .
H6 H 0.3102 0.3024 -0.1376 0.036 Uiso 1 1 calc R . .
C12 C 0.0475(6) 0.3467(5) -0.0778(3) 0.0391(17) Uani 1 1 d . . .
H8 H -0.0186 0.3422 -0.0885 0.047 Uiso 1 1 calc R . .
C8 C 0.2354(6) 0.2803(4) 0.1280(3) 0.0368(17) Uani 1 1 d . . .
H10 H 0.2252 0.2388 0.0969 0.055 Uiso 1 1 calc R . .
H11 H 0.1696 0.2871 0.1639 0.055 Uiso 1 1 calc R . .
H12 H 0.2950 0.2564 0.1466 0.055 Uiso 1 1 calc R . .
C10 C 0.1483(5) 0.3854(4) -0.0017(3) 0.0277(15) Uani 1 1 d . . .
S2 S 0.58985(13) 0.63014(11) 0.32160(8) 0.0284(4) Uani 1 1 d . . .
S3 S 0.14938(14) 0.90490(13) 0.06957(8) 0.0349(4) Uani 1 1 d . . .
S5 S 0.57691(14) 1.12733(11) 0.33325(8) 0.0325(4) Uani 1 1 d . . .
O8 O 0.6661(4) 0.5992(3) 0.2615(2) 0.0333(11) Uani 1 1 d . . .
O7 O 0.2785(4) 0.6466(3) 0.4658(2) 0.0351(11) Uani 1 1 d . . .
H64 H 0.2392 0.6905 0.4562 0.053 Uiso 1 1 calc R . .
O6 O 0.6226(4) 0.6928(3) 0.3606(2) 0.0327(11) Uani 1 1 d . . .
O16 O 0.5457(4) 0.8589(3) -0.0110(2) 0.0384(12) Uani 1 1 d . . .
O11 O 0.2657(4) 1.1440(4) 0.4755(2) 0.0461(13) Uani 1 1 d . . .
H62 H 0.2327 1.1933 0.4691 0.069 Uiso 1 1 calc R . .
O10 O 0.6067(4) 1.1858(3) 0.3763(2) 0.0329(11) Uani 1 1 d . . .
O5 O 0.2323(4) 0.7934(3) 0.4013(2) 0.0434(13) Uani 1 1 d . . .
O15 O 0.4313(4) 0.8504(3) -0.0932(2) 0.0368(12) Uani 1 1 d . . .
H65 H 0.4869 0.8520 -0.0802 0.055 Uiso 1 1 calc R . .
O14 O 0.1734(4) 0.9995(3) 0.0575(2) 0.0393(12) Uani 1 1 d . . .
O13 O 0.0574(4) 0.8791(3) 0.1233(2) 0.0442(13) Uani 1 1 d . . .
O12 O 0.2314(4) 1.2990(4) 0.4198(2) 0.0457(13) Uani 1 1 d . . .
O9 O 0.6556(4) 1.0994(3) 0.2736(2) 0.0433(13) Uani 1 1 d . . .
N4 N 0.2954(4) 0.9396(3) 0.2185(3) 0.0296(13) Uani 1 1 d . . .
N6 N 0.4802(4) 0.6771(4) 0.3000(2) 0.0258(12) Uani 1 1 d . . .
C55 C 0.5589(5) 0.8817(4) 0.1238(3) 0.0273(15) Uani 1 1 d . . .
C20 C 0.5391(5) 0.5362(4) 0.3753(3) 0.0220(14) Uani 1 1 d . . .
N11 N 0.4647(4) 0.8733(4) 0.1017(2) 0.0320(13) Uani 1 1 d . . .
H41 H 0.4033 0.8759 0.1321 0.038 Uiso 1 1 calc R . .
C53 C 0.3540(6) 0.8518(4) 0.0251(3) 0.0308(16) Uani 1 1 d . . .
N7 N 0.2891(4) 1.4470(4) 0.2356(3) 0.0309(13) Uani 1 1 d . . .
N9 N 0.4681(4) 1.1780(4) 0.3113(2) 0.0320(13) Uani 1 1 d . . .
C50 C 0.2386(5) 0.8450(4) -0.0554(3) 0.0305(15) Uani 1 1 d . . .
N5 N 0.3449(4) 0.8370(4) 0.2984(3) 0.0324(13) Uani 1 1 d . . .
H17 H 0.4040 0.8225 0.2682 0.039 Uiso 1 1 calc R . .
C54 C 0.4600(6) 0.8615(5) 0.0369(3) 0.0336(16) Uani 1 1 d . . .
C38 C 0.3768(6) 1.1962(5) 0.3691(3) 0.0356(17) Uani 1 1 d . . .
N12 N 0.5462(5) 0.8557(3) 0.1894(3) 0.0316(13) Uani 1 1 d . . .
C42 C 0.2140(5) 1.4779(5) 0.3534(3) 0.0353(17) Uani 1 1 d . . .
H28 H 0.2089 1.4605 0.3988 0.042 Uiso 1 1 calc R . .
N8 N 0.3397(4) 1.3426(4) 0.3148(3) 0.0335(13) Uani 1 1 d . . .
H29 H 0.4000 1.3299 0.2850 0.040 Uiso 1 1 calc R . .
C24 C 0.3182(5) 0.7789(5) 0.3544(3) 0.0339(16) Uani 1 1 d . . .
N10 N 0.2602(4) 0.8460(4) 0.0824(2) 0.0309(13) Uani 1 1 d . . .
C25 C 0.2853(5) 0.9189(4) 0.2848(3) 0.0301(15) Uani 1 1 d . . .
C52 C 0.3433(5) 0.8485(4) -0.0392(3) 0.0313(16) Uani 1 1 d . . .
C21 C 0.4321(5) 0.5467(4) 0.4176(3) 0.0289(15) Uani 1 1 d . . .
C22 C 0.3650(5) 0.6319(5) 0.4125(3) 0.0311(16) Uani 1 1 d . . .
C26 C 0.2237(5) 0.9741(4) 0.3352(3) 0.0338(16) Uani 1 1 d . . .
H16 H 0.2162 0.9565 0.3808 0.041 Uiso 1 1 calc R . .
C23 C 0.3869(5) 0.6952(4) 0.3580(3) 0.0298(15) Uani 1 1 d . . .
C40 C 0.3114(6) 1.2830(5) 0.3700(3) 0.0411(18) Uani 1 1 d . . .
C51 C 0.1392(5) 0.8655(4) -0.0067(3) 0.0289(15) Uani 1 1 d . . .
C44 C 0.2362(6) 1.5255(5) 0.2196(3) 0.0358(17) Uani 1 1 d . . .
H25 H 0.2437 1.5427 0.1739 0.043 Uiso 1 1 calc R . .
C28 C 0.1844(5) 1.0779(4) 0.2469(3) 0.0340(16) Uani 1 1 d . . .
H14 H 0.1512 1.1324 0.2325 0.041 Uiso 1 1 calc R . .
C17 C 0.4528(6) 0.3938(5) 0.4655(3) 0.0367(17) Uani 1 1 d . . .
H19 H 0.4240 0.3453 0.4952 0.044 Uiso 1 1 calc R . .
C27 C 0.1740(5) 1.0560(5) 0.3152(3) 0.0354(17) Uani 1 1 d . . .
H15 H 0.1342 1.0957 0.3473 0.043 Uiso 1 1 calc R . .
C36 C 0.4157(6) 1.0422(5) 0.4243(3) 0.0349(17) Uani 1 1 d . . .
C19 C 0.6022(6) 0.4547(4) 0.3798(3) 0.0325(16) Uani 1 1 d . . .
H18 H 0.6736 0.4479 0.3528 0.039 Uiso 1 1 calc R . .
C16 C 0.3903(6) 0.4743(5) 0.4628(3) 0.0332(16) Uani 1 1 d . . .
H21 H 0.3199 0.4807 0.4911 0.040 Uiso 1 1 calc R . .
C41 C 0.2766(5) 1.4241(5) 0.3028(3) 0.0337(16) Uani 1 1 d . . .
C43 C 0.1595(5) 1.5577(5) 0.3351(3) 0.0366(17) Uani 1 1 d . . .
H27 H 0.1157 1.5942 0.3681 0.044 Uiso 1 1 calc R . .
C30 C 0.4513(6) 0.6323(5) 0.2455(3) 0.0395(18) Uani 1 1 d . . .
H23 H 0.4328 0.5708 0.2611 0.059 Uiso 1 1 calc R . .
H22 H 0.5127 0.6310 0.2063 0.059 Uiso 1 1 calc R . .
H24 H 0.3898 0.6663 0.2338 0.059 Uiso 1 1 calc R . .
C18 C 0.5585(6) 0.3838(5) 0.4245(3) 0.0347(17) Uani 1 1 d . . .
H20 H 0.6003 0.3289 0.4272 0.042 Uiso 1 1 calc R . .
C45 C 0.1710(5) 1.5828(5) 0.2666(3) 0.0330(16) Uani 1 1 d . . .
H26 H 0.1358 1.6366 0.2528 0.040 Uiso 1 1 calc R . .
C57 C 0.7384(6) 0.9257(4) 0.1122(3) 0.0351(17) Uani 1 1 d . . .
H40 H 0.8029 0.9494 0.0862 0.042 Uiso 1 1 calc R . .
C48 C 0.1320(6) 0.8196(5) -0.1323(4) 0.0422(18) Uani 1 1 d . . .
H44 H 0.1297 0.8043 -0.1749 0.051 Uiso 1 1 calc R . .
C59 C 0.6286(6) 0.8655(5) 0.2170(3) 0.0375(17) Uani 1 1 d . . .
H37 H 0.6205 0.8477 0.2626 0.045 Uiso 1 1 calc R . .
C56 C 0.6534(6) 0.9146(4) 0.0831(3) 0.0364(17) Uani 1 1 d . . .
H39 H 0.6606 0.9291 0.0372 0.044 Uiso 1 1 calc R . .
C34 C 0.5229(6) 1.0307(4) 0.3834(3) 0.0365(17) Uani 1 1 d . . .
C49 C 0.2329(6) 0.8217(5) -0.1186(3) 0.0393(18) Uani 1 1 d . . .
H45 H 0.2969 0.8077 -0.1516 0.047 Uiso 1 1 calc R . .
C58 C 0.7251(6) 0.9009(5) 0.1803(4) 0.0390(18) Uani 1 1 d . . .
H38 H 0.7804 0.9080 0.2011 0.047 Uiso 1 1 calc R . .
C29 C 0.2441(6) 1.0185(4) 0.2005(3) 0.0335(16) Uani 1 1 d . . .
H13 H 0.2494 1.0334 0.1548 0.040 Uiso 1 1 calc R . .
C37 C 0.3526(6) 1.1298(5) 0.4216(3) 0.0367(17) Uani 1 1 d . . .
C39 C 0.4393(7) 1.1398(5) 0.2538(3) 0.045(2) Uani 1 1 d . . .
H36 H 0.4139 1.0798 0.2676 0.068 Uiso 1 1 calc R . .
H34 H 0.5028 1.1360 0.2161 0.068 Uiso 1 1 calc R . .
H35 H 0.3825 1.1792 0.2407 0.068 Uiso 1 1 calc R . .
C35 C 0.5843(7) 0.9481(5) 0.3839(3) 0.049(2) Uani 1 1 d . . .
H30 H 0.6551 0.9414 0.3561 0.058 Uiso 1 1 calc R . .
C47 C 0.0333(6) 0.8395(5) -0.0839(3) 0.0434(19) Uani 1 1 d . . .
H43 H -0.0339 0.8371 -0.0937 0.052 Uiso 1 1 calc R . .
C60 C 0.2460(7) 0.7504(5) 0.1140(4) 0.049(2) Uani 1 1 d . . .
H46 H 0.2358 0.7115 0.0813 0.073 Uiso 1 1 calc R . .
H48 H 0.1831 0.7506 0.1522 0.073 Uiso 1 1 calc R . .
H47 H 0.3101 0.7279 0.1286 0.073 Uiso 1 1 calc R . .
C33 C 0.3709(7) 0.9676(5) 0.4662(3) 0.046(2) Uani 1 1 d . . .
H33 H 0.2997 0.9732 0.4935 0.055 Uiso 1 1 calc R . .
C46 C 0.0391(6) 0.8631(5) -0.0211(4) 0.0413(18) Uani 1 1 d . . .
H42 H -0.0250 0.8774 0.0118 0.050 Uiso 1 1 calc R . .
C32 C 0.4330(8) 0.8856(5) 0.4668(4) 0.054(2) Uani 1 1 d . . .
H32 H 0.4029 0.8362 0.4949 0.065 Uiso 1 1 calc R . .
C31 C 0.5391(8) 0.8750(6) 0.4266(4) 0.061(3) Uani 1 1 d . . .
H31 H 0.5799 0.8193 0.4282 0.073 Uiso 1 1 calc R . .
S4 S 0.00294(15) 0.29357(12) 0.31046(8) 0.0365(5) Uani 1 1 d . . .
O19 O -0.0171(4) 0.3745(3) 0.5075(2) 0.0385(12) Uani 1 1 d . . .
O17 O 0.1189(4) 0.2822(3) 0.3025(2) 0.0411(12) Uani 1 1 d . . .
O20 O -0.0046(4) 0.0972(3) 0.4741(2) 0.0410(12) Uani 1 1 d . . .
O18 O -0.0397(4) 0.2726(3) 0.2559(2) 0.0434(13) Uani 1 1 d . . .
N14 N 0.0171(4) 0.2066(4) 0.5420(3) 0.0366(14) Uani 1 1 d . . .
H53 H 0.0214 0.2643 0.5443 0.044 Uiso 1 1 calc R . .
N15 N 0.0463(5) 0.0607(4) 0.5907(3) 0.0378(14) Uani 1 1 d . . .
H63 H 0.0423 0.0383 0.5542 0.045 Uiso 1 1 calc R . .
C65 C -0.0624(5) 0.4207(4) 0.4036(3) 0.0257(14) Uani 1 1 d . . .
C68 C -0.0296(5) 0.2569(5) 0.4393(3) 0.0330(16) Uani 1 1 d . . .
N13 N -0.0566(4) 0.2314(4) 0.3780(3) 0.0340(14) Uani 1 1 d . . .
C69 C -0.0054(6) 0.1797(5) 0.4834(3) 0.0376(18) Uani 1 1 d . . .
C70 C 0.0323(6) 0.1518(5) 0.5942(3) 0.0343(16) Uani 1 1 d . . .
C73 C 0.0727(6) 0.0323(5) 0.7012(4) 0.0391(17) Uani 1 1 d . . .
H50 H 0.0883 -0.0070 0.7361 0.047 Uiso 1 1 calc R . .
C76 C -0.1742(6) 0.2221(5) 0.3871(4) 0.0440(19) Uani 1 1 d . . .
H58 H -0.1982 0.1739 0.4213 0.066 Uiso 1 1 calc R . .
H57 H -0.1865 0.2075 0.3451 0.066 Uiso 1 1 calc R . .
H59 H -0.2147 0.2787 0.4009 0.066 Uiso 1 1 calc R . .
C67 C -0.0343(6) 0.3471(5) 0.4522(3) 0.0372(17) Uani 1 1 d . . .
C62 C -0.1157(6) 0.5578(5) 0.3107(4) 0.0437(19) Uani 1 1 d . . .
H56 H -0.1332 0.6040 0.2804 0.052 Uiso 1 1 calc R . .
C66 C -0.0459(5) 0.4035(5) 0.3344(3) 0.0348(17) Uani 1 1 d . . .
C61 C -0.0710(5) 0.4710(4) 0.2890(3) 0.0343(16) Uani 1 1 d . . .
H61 H -0.0584 0.4592 0.2437 0.041 Uiso 1 1 calc R . .
C64 C -0.1043(6) 0.5055(5) 0.4241(4) 0.0411(18) Uani 1 1 d . . .
H54 H -0.1138 0.5185 0.4690 0.049 Uiso 1 1 calc R . .
C74 C 0.0538(6) 0.1285(5) 0.7067(3) 0.048(2) Uani 1 1 d . . .
H51 H 0.0563 0.1513 0.7471 0.057 Uiso 1 1 calc R . .
C63 C -0.1328(6) 0.5724(5) 0.3784(4) 0.0463(19) Uani 1 1 d . . .
H55 H -0.1644 0.6288 0.3938 0.056 Uiso 1 1 calc R . .
C72 C 0.0666(6) 0.0010(5) 0.6421(4) 0.0466(19) Uani 1 1 d . . .
H49 H 0.0764 -0.0615 0.6363 0.056 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
C75 C74 1.330(10) . ?
C75 C70 1.466(9) . ?
C75 H52 0.9300 . ?
S1 O2 1.425(4) . ?
S1 O1 1.444(4) . ?
S1 N3 1.656(6) . ?
S1 C10 1.765(6) . ?
O3 C15 1.355(7) . ?
O3 H60 0.8200 . ?
O4 C6 1.250(7) . ?
N1 C5 1.333(8) . ?
N1 C1 1.338(8) . ?
N3 C7 1.425(7) . ?
N3 C8 1.499(8) . ?
C6 N2 1.365(8) . ?
C6 C7 1.458(10) . ?
C15 C7 1.377(9) . ?
C15 C9 1.448(9) . ?
C3 C2 1.361(10) . ?
C3 C4 1.390(9) . ?
C3 H3 0.9300 . ?
N2 C1 1.430(8) . ?
N2 H5 0.8600 . ?
C1 C2 1.359(9) . ?
C5 C4 1.375(9) . ?
C5 H1 0.9300 . ?
C4 H2 0.9300 . ?
C13 C14 1.374(10) . ?
C13 C12 1.395(9) . ?
C13 H7 0.9300 . ?
C2 H4 0.9300 . ?
C11 C10 1.384(9) . ?
C11 C12 1.387(9) . ?
C11 H9 0.9300 . ?
C9 C10 1.400(8) . ?
C9 C14 1.410(8) . ?
C14 H6 0.9300 . ?
C12 H8 0.9300 . ?
C8 H10 0.9600 . ?
C8 H11 0.9600 . ?
C8 H12 0.9600 . ?
S2 O6 1.428(4) . ?
S2 O8 1.432(4) . ?
S2 N6 1.644(5) . ?
S2 C20 1.747(6) . ?
S3 O13 1.431(5) . ?
S3 O14 1.436(5) . ?
S3 N10 1.651(6) . ?
S3 C51 1.755(6) . ?
S5 O9 1.425(4) . ?
S5 O10 1.425(4) . ?
S5 N9 1.656(6) . ?
S5 C34 1.757(6) . ?
O7 C22 1.345(7) . ?
O7 H64 0.8200 . ?
O16 C54 1.259(7) . ?
O11 C37 1.354(8) . ?
O11 H62 0.8200 . ?
O5 C24 1.265(7) . ?
O15 C52 1.350(7) . ?
O15 H65 0.8200 . ?
O12 C40 1.256(8) . ?
N4 C25 1.343(8) . ?
N4 C29 1.346(8) . ?
N6 C23 1.464(7) . ?
N6 C30 1.486(7) . ?
C55 N12 1.338(8) . ?
C55 C56 1.368(9) . ?
C55 N11 1.403(8) . ?
C20 C19 1.388(9) . ?
C20 C21 1.407(8) . ?
N11 C54 1.373(8) . ?
N11 H41 0.8600 . ?
C53 C52 1.365(9) . ?
C53 N10 1.437(7) . ?
C53 C54 1.451(10) . ?
N7 C44 1.340(8) . ?
N7 C41 1.359(8) . ?
N9 C38 1.446(8) . ?
N9 C39 1.491(8) . ?
C50 C49 1.390(9) . ?
C50 C51 1.413(8) . ?
C50 C52 1.459(9) . ?
N5 C24 1.354(8) . ?
N5 C25 1.407(8) . ?
N5 H17 0.8600 . ?
C38 C37 1.378(9) . ?
C38 C40 1.453(10) . ?
N12 C59 1.337(9) . ?
C42 C43 1.379(10) . ?
C42 C41 1.389(9) . ?
C42 H28 0.9300 . ?
N8 C40 1.359(9) . ?
N8 C41 1.418(9) . ?
N8 H29 0.8600 . ?
C24 C23 1.449(9) . ?
N10 C60 1.498(8) . ?
C25 C26 1.393(9) . ?
C21 C16 1.394(9) . ?
C21 C22 1.459(9) . ?
C22 C23 1.374(9) . ?
C26 C27 1.387(9) . ?
C26 H16 0.9300 . ?
C51 C46 1.382(10) . ?
C44 C45 1.385(9) . ?
C44 H25 0.9300 . ?
C28 C29 1.373(9) . ?
C28 C27 1.384(9) . ?
C28 H14 0.9300 . ?
C17 C16 1.366(9) . ?
C17 C18 1.384(9) . ?
C17 H19 0.9300 . ?
C27 H15 0.9300 . ?
C36 C33 1.398(9) . ?
C36 C34 1.401(10) . ?
C36 C37 1.457(10) . ?
C19 C18 1.379(9) . ?
C19 H18 0.9300 . ?
C16 H21 0.9300 . ?
C43 C45 1.393(9) . ?
C43 H27 0.9300 . ?
C30 H23 0.9600 . ?
C30 H22 0.9600 . ?
C30 H24 0.9600 . ?
C18 H20 0.9300 . ?
C45 H26 0.9300 . ?
C57 C58 1.382(9) . ?
C57 C56 1.391(10) . ?
C57 H40 0.9300 . ?
C48 C49 1.386(10) . ?
C48 C47 1.403(10) . ?
C48 H44 0.9300 . ?
C59 C58 1.376(9) . ?
C59 H37 0.9300 . ?
C56 H39 0.9300 . ?
C34 C35 1.382(10) . ?
C49 H45 0.9300 . ?
C58 H38 0.9300 . ?
C29 H13 0.9300 . ?
C39 H36 0.9600 . ?
C39 H34 0.9600 . ?
C39 H35 0.9600 . ?
C35 C31 1.389(10) . ?
C35 H30 0.9300 . ?
C47 C46 1.387(9) . ?
C47 H43 0.9300 . ?
C60 H46 0.9600 . ?
C60 H48 0.9600 . ?
C60 H47 0.9600 . ?
C33 C32 1.377(11) . ?
C33 H33 0.9300 . ?
C46 H42 0.9300 . ?
C32 C31 1.383(12) . ?
C32 H32 0.9300 . ?
C31 H31 0.9300 . ?
S4 O17 1.432(5) . ?
S4 O18 1.432(5) . ?
S4 N13 1.635(6) . ?
S4 C66 1.741(7) . ?
O19 C67 1.313(8) . ?
O20 C69 1.243(8) . ?
N14 C70 1.325(8) . ?
N14 C69 1.402(8) . ?
N14 H53 0.8600 . ?
N15 C70 1.340(9) . ?
N15 C72 1.371(9) . ?
N15 H63 0.8600 . ?
C65 C64 1.366(9) . ?
C65 C66 1.420(8) . ?
C65 C67 1.488(9) . ?
C68 C67 1.368(9) . ?
C68 C69 1.448(10) . ?
C68 N13 1.475(8) . ?
N13 C76 1.473(8) . ?
C73 C72 1.357(9) . ?
C73 C74 1.422(10) . ?
C73 H50 0.9300 . ?
C76 H58 0.9600 . ?
C76 H57 0.9600 . ?
C76 H59 0.9600 . ?
C62 C63 1.380(10) . ?
C62 C61 1.408(9) . ?
C62 H56 0.9300 . ?
C66 C61 1.372(9) . ?
C61 H61 0.9300 . ?
C64 C63 1.388(10) . ?
C64 H54 0.9300 . ?
C74 H51 0.9300 . ?
C63 H55 0.9300 . ?
C72 H49 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
C74 C75 C70 117.1(7) . . ?
C74 C75 H52 121.5 . . ?
C70 C75 H52 121.5 . . ?
O2 S1 O1 119.0(3) . . ?
O2 S1 N3 109.4(3) . . ?
O1 S1 N3 106.8(3) . . ?
O2 S1 C10 110.3(3) . . ?
O1 S1 C10 108.3(3) . . ?
N3 S1 C10 101.6(3) . . ?
C15 O3 H60 109.5 . . ?
C5 N1 C1 116.6(5) . . ?
C7 N3 C8 115.0(5) . . ?
C7 N3 S1 113.3(4) . . ?
C8 N3 S1 115.5(4) . . ?
O4 C6 N2 122.1(6) . . ?
O4 C6 C7 120.2(6) . . ?
N2 C6 C7 117.7(6) . . ?
O3 C15 C7 120.9(6) . . ?
O3 C15 C9 115.7(5) . . ?
C7 C15 C9 123.4(6) . . ?
C2 C3 C4 120.4(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C15 C7 N3 119.8(6) . . ?
C15 C7 C6 120.5(6) . . ?
N3 C7 C6 119.6(5) . . ?
C6 N2 C1 125.6(5) . . ?
C6 N2 H5 117.2 . . ?
C1 N2 H5 117.2 . . ?
N1 C1 C2 124.4(6) . . ?
N1 C1 N2 111.7(5) . . ?
C2 C1 N2 123.8(6) . . ?
N1 C5 C4 123.8(6) . . ?
N1 C5 H1 118.1 . . ?
C4 C5 H1 118.1 . . ?
C5 C4 C3 117.1(7) . . ?
C5 C4 H2 121.5 . . ?
C3 C4 H2 121.5 . . ?
C14 C13 C12 122.2(6) . . ?
C14 C13 H7 118.9 . . ?
C12 C13 H7 118.9 . . ?
C1 C2 C3 117.7(6) . . ?
C1 C2 H4 121.1 . . ?
C3 C2 H4 121.1 . . ?
C10 C11 C12 119.7(6) . . ?
C10 C11 H9 120.1 . . ?
C12 C11 H9 120.1 . . ?
C10 C9 C14 118.0(6) . . ?
C10 C9 C15 121.0(6) . . ?
C14 C9 C15 120.9(6) . . ?
C13 C14 C9 119.4(6) . . ?
C13 C14 H6 120.3 . . ?
C9 C14 H6 120.3 . . ?
C11 C12 C13 118.7(7) . . ?
C11 C12 H8 120.7 . . ?
C13 C12 H8 120.7 . . ?
N3 C8 H10 109.5 . . ?
N3 C8 H11 109.5 . . ?
H10 C8 H11 109.5 . . ?
N3 C8 H12 109.5 . . ?
H10 C8 H12 109.5 . . ?
H11 C8 H12 109.5 . . ?
C11 C10 C9 121.9(6) . . ?
C11 C10 S1 121.5(5) . . ?
C9 C10 S1 116.6(5) . . ?
O6 S2 O8 119.4(3) . . ?
O6 S2 N6 107.9(3) . . ?
O8 S2 N6 107.6(3) . . ?
O6 S2 C20 108.4(3) . . ?
O8 S2 C20 109.9(3) . . ?
N6 S2 C20 102.3(3) . . ?
O13 S3 O14 119.2(3) . . ?
O13 S3 N10 108.4(3) . . ?
O14 S3 N10 107.2(3) . . ?
O13 S3 C51 109.7(3) . . ?
O14 S3 C51 108.3(3) . . ?
N10 S3 C51 102.7(3) . . ?
O9 S5 O10 119.7(3) . . ?
O9 S5 N9 108.5(3) . . ?
O10 S5 N9 107.4(3) . . ?
O9 S5 C34 109.9(3) . . ?
O10 S5 C34 107.8(3) . . ?
N9 S5 C34 102.0(3) . . ?
C22 O7 H64 109.5 . . ?
C37 O11 H62 109.5 . . ?
C52 O15 H65 109.5 . . ?
C25 N4 C29 117.6(5) . . ?
C23 N6 C30 113.6(5) . . ?
C23 N6 S2 113.5(4) . . ?
C30 N6 S2 114.8(4) . . ?
N12 C55 C56 123.1(6) . . ?
N12 C55 N11 112.9(5) . . ?
C56 C55 N11 124.0(6) . . ?
C19 C20 C21 119.9(6) . . ?
C19 C20 S2 122.3(5) . . ?
C21 C20 S2 117.8(5) . . ?
C54 N11 C55 127.1(5) . . ?
C54 N11 H41 116.5 . . ?
C55 N11 H41 116.5 . . ?
C52 C53 N10 120.6(6) . . ?
C52 C53 C54 120.8(6) . . ?
N10 C53 C54 118.6(5) . . ?
C44 N7 C41 116.3(6) . . ?
C38 N9 C39 115.1(5) . . ?
C38 N9 S5 112.7(4) . . ?
C39 N9 S5 116.0(5) . . ?
C49 C50 C51 118.0(6) . . ?
C49 C50 C52 121.7(6) . . ?
C51 C50 C52 120.4(5) . . ?
C24 N5 C25 126.3(5) . . ?
C24 N5 H17 116.8 . . ?
C25 N5 H17 116.8 . . ?
O16 C54 N11 120.8(6) . . ?
O16 C54 C53 120.8(6) . . ?
N11 C54 C53 118.4(6) . . ?
C37 C38 N9 118.9(6) . . ?
C37 C38 C40 121.5(6) . . ?
N9 C38 C40 119.6(6) . . ?
C59 N12 C55 118.2(6) . . ?
C43 C42 C41 118.7(6) . . ?
C43 C42 H28 120.6 . . ?
C41 C42 H28 120.6 . . ?
C40 N8 C41 124.5(6) . . ?
C40 N8 H29 117.8 . . ?
C41 N8 H29 117.8 . . ?
O5 C24 N5 121.9(6) . . ?
O5 C24 C23 119.5(6) . . ?
N5 C24 C23 118.5(6) . . ?
C53 N10 C60 113.0(5) . . ?
C53 N10 S3 113.5(4) . . ?
C60 N10 S3 116.6(5) . . ?
N4 C25 C26 123.3(6) . . ?
N4 C25 N5 113.4(5) . . ?
C26 C25 N5 123.3(6) . . ?
O15 C52 C53 121.1(6) . . ?
O15 C52 C50 115.0(5) . . ?
C53 C52 C50 123.9(6) . . ?
C16 C21 C20 119.3(6) . . ?
C16 C21 C22 120.6(6) . . ?
C20 C21 C22 120.1(6) . . ?
O7 C22 C23 120.6(6) . . ?
O7 C22 C21 115.7(5) . . ?
C23 C22 C21 123.7(6) . . ?
C27 C26 C25 117.9(6) . . ?
C27 C26 H16 121.0 . . ?
C25 C26 H16 121.0 . . ?
C22 C23 C24 122.3(6) . . ?
C22 C23 N6 119.7(6) . . ?
C24 C23 N6 117.9(5) . . ?
O12 C40 N8 123.1(7) . . ?
O12 C40 C38 120.0(6) . . ?
N8 C40 C38 116.9(6) . . ?
C46 C51 C50 121.4(6) . . ?
C46 C51 S3 121.5(5) . . ?
C50 C51 S3 116.8(5) . . ?
N7 C44 C45 124.2(6) . . ?
N7 C44 H25 117.9 . . ?
C45 C44 H25 117.9 . . ?
C29 C28 C27 119.3(6) . . ?
C29 C28 H14 120.3 . . ?
C27 C28 H14 120.3 . . ?
C16 C17 C18 120.6(6) . . ?
C16 C17 H19 119.7 . . ?
C18 C17 H19 119.7 . . ?
C28 C27 C26 119.0(6) . . ?
C28 C27 H15 120.5 . . ?
C26 C27 H15 120.5 . . ?
C33 C36 C34 118.5(7) . . ?
C33 C36 C37 121.4(7) . . ?
C34 C36 C37 120.1(6) . . ?
C18 C19 C20 119.6(6) . . ?
C18 C19 H18 120.2 . . ?
C20 C19 H18 120.2 . . ?
C17 C16 C21 120.1(6) . . ?
C17 C16 H21 120.0 . . ?
C21 C16 H21 120.0 . . ?
N7 C41 C42 123.4(6) . . ?
N7 C41 N8 112.3(5) . . ?
C42 C41 N8 124.2(6) . . ?
C42 C43 C45 119.1(6) . . ?
C42 C43 H27 120.5 . . ?
C45 C43 H27 120.5 . . ?
N6 C30 H23 109.5 . . ?
N6 C30 H22 109.5 . . ?
H23 C30 H22 109.5 . . ?
N6 C30 H24 109.5 . . ?
H23 C30 H24 109.5 . . ?
H22 C30 H24 109.5 . . ?
C19 C18 C17 120.5(7) . . ?
C19 C18 H20 119.7 . . ?
C17 C18 H20 119.7 . . ?
C44 C45 C43 118.2(7) . . ?
C44 C45 H26 120.9 . . ?
C43 C45 H26 120.9 . . ?
C58 C57 C56 118.8(6) . . ?
C58 C57 H40 120.6 . . ?
C56 C57 H40 120.6 . . ?
C49 C48 C47 122.1(6) . . ?
C49 C48 H44 119.0 . . ?
C47 C48 H44 119.0 . . ?
N12 C59 C58 122.5(6) . . ?
N12 C59 H37 118.8 . . ?
C58 C59 H37 118.8 . . ?
C55 C56 C57 118.5(6) . . ?
C55 C56 H39 120.8 . . ?
C57 C56 H39 120.8 . . ?
C35 C34 C36 121.5(6) . . ?
C35 C34 S5 121.6(6) . . ?
C36 C34 S5 116.8(5) . . ?
C48 C49 C50 120.0(6) . . ?
C48 C49 H45 120.0 . . ?
C50 C49 H45 120.0 . . ?
C59 C58 C57 118.9(7) . . ?
C59 C58 H38 120.5 . . ?
C57 C58 H38 120.5 . . ?
N4 C29 C28 122.8(6) . . ?
N4 C29 H13 118.6 . . ?
C28 C29 H13 118.6 . . ?
O11 C37 C38 120.2(7) . . ?
O11 C37 C36 115.6(6) . . ?
C38 C37 C36 124.2(6) . . ?
N9 C39 H36 109.5 . . ?
N9 C39 H34 109.5 . . ?
H36 C39 H34 109.5 . . ?
N9 C39 H35 109.5 . . ?
H36 C39 H35 109.5 . . ?
H34 C39 H35 109.5 . . ?
C34 C35 C31 119.2(8) . . ?
C34 C35 H30 120.4 . . ?
C31 C35 H30 120.4 . . ?
C46 C47 C48 117.8(7) . . ?
C46 C47 H43 121.1 . . ?
C48 C47 H43 121.1 . . ?
N10 C60 H46 109.5 . . ?
N10 C60 H48 109.5 . . ?
H46 C60 H48 109.5 . . ?
N10 C60 H47 109.5 . . ?
H46 C60 H47 109.5 . . ?
H48 C60 H47 109.5 . . ?
C32 C33 C36 119.6(8) . . ?
C32 C33 H33 120.2 . . ?
C36 C33 H33 120.2 . . ?
C51 C46 C47 120.7(7) . . ?
C51 C46 H42 119.6 . . ?
C47 C46 H42 119.6 . . ?
C33 C32 C31 121.6(7) . . ?
C33 C32 H32 119.2 . . ?
C31 C32 H32 119.2 . . ?
C32 C31 C35 119.6(8) . . ?
C32 C31 H31 120.2 . . ?
C35 C31 H31 120.2 . . ?
O17 S4 O18 118.7(3) . . ?
O17 S4 N13 108.3(3) . . ?
O18 S4 N13 107.7(3) . . ?
O17 S4 C66 109.8(3) . . ?
O18 S4 C66 109.6(3) . . ?
N13 S4 C66 101.2(3) . . ?
C70 N14 C69 126.3(6) . . ?
C70 N14 H53 116.8 . . ?
C69 N14 H53 116.8 . . ?
C70 N15 C72 123.8(6) . . ?
C70 N15 H63 118.1 . . ?
C72 N15 H63 118.1 . . ?
C64 C65 C66 118.7(6) . . ?
C64 C65 C67 121.2(6) . . ?
C66 C65 C67 120.1(6) . . ?
C67 C68 C69 125.5(6) . . ?
C67 C68 N13 120.0(6) . . ?
C69 C68 N13 114.4(5) . . ?
C76 N13 C68 113.7(5) . . ?
C76 N13 S4 115.4(5) . . ?
C68 N13 S4 112.0(4) . . ?
O20 C69 N14 120.5(7) . . ?
O20 C69 C68 126.7(6) . . ?
N14 C69 C68 112.7(6) . . ?
N14 C70 N15 121.3(6) . . ?
N14 C70 C75 121.4(6) . . ?
N15 C70 C75 117.3(6) . . ?
C72 C73 C74 116.2(7) . . ?
C72 C73 H50 121.9 . . ?
C74 C73 H50 121.9 . . ?
N13 C76 H58 109.5 . . ?
N13 C76 H57 109.5 . . ?
H58 C76 H57 109.5 . . ?
N13 C76 H59 109.5 . . ?
H58 C76 H59 109.5 . . ?
H57 C76 H59 109.5 . . ?
O19 C67 C68 123.3(7) . . ?
O19 C67 C65 116.0(6) . . ?
C68 C67 C65 120.7(6) . . ?
C63 C62 C61 117.9(7) . . ?
C63 C62 H56 121.0 . . ?
C61 C62 H56 121.0 . . ?
C61 C66 C65 120.6(6) . . ?
C61 C66 S4 121.7(5) . . ?
C65 C66 S4 117.6(5) . . ?
C66 C61 C62 120.4(7) . . ?
C66 C61 H61 119.8 . . ?
C62 C61 H61 119.8 . . ?
C65 C64 C63 120.3(7) . . ?
C65 C64 H54 119.9 . . ?
C63 C64 H54 119.9 . . ?
C75 C74 C73 124.7(7) . . ?
C75 C74 H51 117.6 . . ?
C73 C74 H51 117.6 . . ?
C62 C63 C64 122.0(7) . . ?
C62 C63 H55 119.0 . . ?
C64 C63 H55 119.0 . . ?
C73 C72 N15 120.7(7) . . ?
C73 C72 H49 119.6 . . ?
N15 C72 H49 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         1.494
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.132
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1451208'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_ATOM007_shelxl              
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution.  It was therefore not
possible to obtain a meaningful anisotropic refinement of the
displacement parameters and all atoms were only refined isotropically.
;
_vrf_RFACG01_shelxl              
;
PROBLEM: The value of the R factor is > 0.20
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. These
were the best data we were able to obtain. 
;
_vrf_RFACR01_shelxl              
;
PROBLEM: The value of the weighted R factor is > 0.45
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. These
were the best data we were able to obtain.  
;
_vrf_THETM01_shelxl              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. These
were the best data we were able to obtain.
;
_vrf_RINTA01_shelxl              
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. These
were the best data we were able to obtain.
;
_vrf_PLAT082_shelxl              
;
PROBLEM: High R1 Value ..................................       0.23 Report
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. It was therefore 
not possible to obtain a meaningful anisotropic refinement of the
displacement parameters and all atoms were only refined isotropically. These
were the best data we were able to obtain.
;
_vrf_PLAT084_shelxl              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.53 Report
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. It was therefore 
not possible to obtain a meaningful anisotropic refinement of the
displacement parameters and all atoms were only refined isotropically. These
were the best data we were able to obtain.
;
_vrf_PLAT201_shelxl              
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         69 Report
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. It was therefore 
not possible to obtain a meaningful anisotropic refinement of the
displacement parameters and all atoms were only refined isotropically. These
were the best data we were able to obtain.
;
_vrf_PLAT020_shelxl              
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.236 Report
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. It was therefore 
not possible to obtain a meaningful anisotropic refinement of the
displacement parameters and all atoms were only refined isotropically. These
were the best data we were able to obtain.
;
_vrf_PLAT340_shelxl              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03692 Ang.  
RESPONSE: The crystals were very small and needle shaped and very
weakly diffracting.  The data to parameter ratio were low and the 
data only diffracted to low resolution giving high R factors. It was therefore 
not possible to obtain a meaningful anisotropic refinement of the
displacement parameters and all atoms were only refined isotropically. These
were the best data we were able to obtain.
;
_vrf_PLAT780_shelxl              
;
PROBLEM: Coordinates do not Form a Properly Connected Set     Please Do ! 
RESPONSE: The molecules are fully connected within the cif.  There are three
independent piroxicam molecules and one methanol molecule in the asymmetric 
unit.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'piroxicam methanol solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H43 N9 O13 S3'
_chemical_formula_weight         1026.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.0374(19)
_cell_length_b                   12.917(4)
_cell_length_c                   25.467(8)
_cell_angle_alpha                84.077(7)
_cell_angle_beta                 89.174(7)
_cell_angle_gamma                83.327(6)
_cell_volume                     2287.0(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5509
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      21.18

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2351
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Image Plate'
_diffrn_measurement_method       'Image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14992
_diffrn_reflns_av_R_equivalents  0.2357
_diffrn_reflns_av_sigmaI/netI    0.2334
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         20.82
_reflns_number_total             4731
_reflns_number_gt                2059
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
'The data are of poor quality and therefore only an isotropic refinement of the displacement parameters has been carried out.'

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4731
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.3371
_refine_ls_R_factor_gt           0.2271
_refine_ls_wR_factor_ref         0.5325
_refine_ls_wR_factor_gt          0.4776
_refine_ls_goodness_of_fit_ref   1.440
_refine_ls_restrained_S_all      1.440
_refine_ls_shift/su_max          0.023
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O13 O 0.789(2) 0.2981(13) 0.3820(6) 0.066(5) Uiso 1 1 d D . .
C46 C 0.069(3) 0.628(2) 0.2718(10) 0.072(8) Uiso 1 1 d . . .
H23 H 0.0118 0.5703 0.2606 0.107 Uiso 1 1 calc R . .
H25 H 0.0438 0.6880 0.2462 0.107 Uiso 1 1 calc R . .
H24 H 0.0157 0.6450 0.3053 0.107 Uiso 1 1 calc R . .
C50 C 0.876(4) 0.391(2) 0.3736(11) 0.077(8) Uiso 1 1 d . . .
H40 H 0.8428 0.4334 0.4020 0.116 Uiso 1 1 calc R . .
H41 H 0.8321 0.4291 0.3408 0.116 Uiso 1 1 calc R . .
H39 H 1.0123 0.3742 0.3723 0.116 Uiso 1 1 calc R . .
C30 C 0.260(3) 0.753(2) 0.0742(9) 0.056(7) Uiso 1 1 d . . .
H29 H 0.2435 0.8214 0.0585 0.067 Uiso 1 1 calc R . .
H44 H 0.661(5) 0.300(17) 0.385(8) 0.084 Uiso 1 1 d D . .
S2 S 0.1595(9) 0.1224(6) 0.0204(3) 0.062(2) Uiso 1 1 d . . .
O7 O 0.231(2) 0.0118(13) 0.0358(6) 0.069(5) Uiso 1 1 d . . .
O8 O 0.330(2) 0.3501(13) 0.1096(6) 0.066(5) Uiso 1 1 d . . .
N4 N 0.309(3) 0.1921(16) 0.0440(8) 0.061(6) Uiso 1 1 d . . .
N5 N 0.277(2) 0.4809(16) 0.0392(8) 0.065(6) Uiso 1 1 d . . .
H31 H 0.2681 0.4927 0.0054 0.078 Uiso 1 1 calc R . .
N6 N 0.311(2) 0.5522(16) 0.1197(8) 0.059(6) Uiso 1 1 d . . .
H26 H 0.3342 0.4890 0.1343 0.071 Uiso 1 1 calc R . .
O6 O -0.028(2) 0.1587(12) 0.0331(6) 0.061(5) Uiso 1 1 d . . .
O5 O 0.225(2) 0.4306(14) -0.0533(7) 0.071(5) Uiso 1 1 d . . .
C23 C 0.276(3) 0.3049(19) 0.0215(10) 0.056(7) Uiso 1 1 d . . .
C18 C 0.179(3) 0.074(2) -0.0831(9) 0.053(6) Uiso 1 1 d . . .
H35 H 0.1805 0.0040 -0.0696 0.064 Uiso 1 1 calc R . .
C16 C 0.221(3) 0.2026(19) -0.1575(10) 0.061(7) Uiso 1 1 d . . .
H33 H 0.2296 0.2210 -0.1937 0.074 Uiso 1 1 calc R . .
C24 C 0.290(3) 0.3769(19) 0.0613(9) 0.049(6) Uiso 1 1 d . . .
C27 C 0.283(4) 0.735(2) 0.1272(11) 0.085(9) Uiso 1 1 d . . .
H28 H 0.2815 0.7907 0.1478 0.102 Uiso 1 1 calc R . .
C20 C 0.228(3) 0.253(2) -0.0691(10) 0.062(7) Uiso 1 1 d . . .
C22 C 0.248(3) 0.3329(19) -0.0308(9) 0.055(6) Uiso 1 1 d . . .
C26 C 0.260(3) 0.6688(19) 0.0417(10) 0.056(7) Uiso 1 1 d . . .
H30 H 0.2476 0.6813 0.0052 0.068 Uiso 1 1 calc R . .
C28 C 0.309(3) 0.631(2) 0.1506(11) 0.071(8) Uiso 1 1 d . . .
H27 H 0.3249 0.6165 0.1869 0.085 Uiso 1 1 calc R . .
C17 C 0.190(3) 0.0976(18) -0.1373(9) 0.054(6) Uiso 1 1 d . . .
H34 H 0.1761 0.0471 -0.1601 0.065 Uiso 1 1 calc R . .
C21 C 0.241(3) 0.280(2) -0.1204(11) 0.079(8) Uiso 1 1 d . . .
H32 H 0.2619 0.3477 -0.1328 0.094 Uiso 1 1 calc R . .
C29 C 0.524(3) 0.152(2) 0.0496(10) 0.076(8) Uiso 1 1 d . . .
H36 H 0.5810 0.1493 0.0152 0.113 Uiso 1 1 calc R . .
H37 H 0.5381 0.0824 0.0680 0.113 Uiso 1 1 calc R . .
H38 H 0.5864 0.1976 0.0691 0.113 Uiso 1 1 calc R . .
C19 C 0.167(3) 0.151(2) -0.0474(10) 0.064(7) Uiso 1 1 d . . .
C25 C 0.278(3) 0.5663(19) 0.0676(9) 0.052(6) Uiso 1 1 d . . .
S1 S -0.3260(9) 1.0182(6) 0.4323(3) 0.063(2) Uiso 1 1 d . . .
O2 O -0.139(2) 1.0131(13) 0.2499(6) 0.063(5) Uiso 1 1 d . . .
O4 O -0.3001(18) 1.0646(11) 0.4808(6) 0.049(4) Uiso 1 1 d . . .
O3 O -0.5093(19) 1.0350(11) 0.4111(6) 0.054(4) Uiso 1 1 d . . .
C6 C -0.250(3) 0.885(2) 0.4427(11) 0.068(7) Uiso 1 1 d . . .
C8 C -0.175(3) 1.0029(19) 0.3414(9) 0.052(6) Uiso 1 1 d . . .
N1 N -0.176(3) 1.0584(17) 0.3889(8) 0.073(6) Uiso 1 1 d . . .
N2 N -0.169(2) 1.1694(15) 0.2881(7) 0.052(5) Uiso 1 1 d . . .
H5 H -0.1806 1.1967 0.3175 0.062 Uiso 1 1 calc R . .
C2 C -0.215(3) 0.7189(18) 0.4974(9) 0.049(6) Uiso 1 1 d . . .
H2 H -0.2191 0.6808 0.5304 0.059 Uiso 1 1 calc R . .
O1 O -0.156(2) 0.8416(14) 0.3043(7) 0.083(6) Uiso 1 1 d . . .
H42 H -0.1551 0.8829 0.2776 0.125 Uiso 1 1 calc R . .
C7 C -0.175(3) 0.8952(19) 0.3471(9) 0.048(6) Uiso 1 1 d . . .
C10 C -0.167(3) 1.2409(19) 0.2402(9) 0.049(6) Uiso 1 1 d . . .
C15 C 0.023(3) 1.074(2) 0.4089(10) 0.073(8) Uiso 1 1 d . . .
H12 H 0.0917 1.0074 0.4205 0.109 Uiso 1 1 calc R . .
H11 H 0.0084 1.1165 0.4379 0.109 Uiso 1 1 calc R . .
H10 H 0.0924 1.1088 0.3809 0.109 Uiso 1 1 calc R . .
C1 C -0.255(3) 0.8271(17) 0.4929(9) 0.044(6) Uiso 1 1 d . . .
H1 H -0.2856 0.8615 0.5228 0.053 Uiso 1 1 calc R . .
C3 C -0.170(3) 0.668(2) 0.4538(10) 0.064(7) Uiso 1 1 d . . .
H3 H -0.1527 0.5949 0.4572 0.077 Uiso 1 1 calc R . .
C5 C -0.192(3) 0.833(2) 0.3959(9) 0.057(7) Uiso 1 1 d . . .
C4 C -0.149(3) 0.7242(19) 0.4024(10) 0.059(7) Uiso 1 1 d . . .
H4 H -0.1065 0.6882 0.3739 0.071 Uiso 1 1 calc R . .
C12 C 0.148(3) 0.706(2) -0.1473(10) 0.061(7) Uiso 1 1 d . . .
H8 H 0.1255 0.7220 -0.1128 0.073 Uiso 1 1 calc R . .
C9 C -0.156(3) 1.066(2) 0.2904(10) 0.060(7) Uiso 1 1 d . . .
C14 C -0.217(4) 1.420(2) 0.2137(12) 0.086(9) Uiso 1 1 d . . .
H7 H -0.2490 1.4886 0.2208 0.104 Uiso 1 1 calc R . .
N3 N -0.204(3) 1.3407(19) 0.2544(9) 0.082(7) Uiso 1 1 d . . .
C13 C 0.182(4) 0.604(3) -0.1591(12) 0.096(10) Uiso 1 1 d . . .
H9 H 0.1820 0.5495 -0.1322 0.115 Uiso 1 1 calc R . .
C11 C -0.149(3) 1.213(2) 0.1902(9) 0.055(7) Uiso 1 1 d . . .
H6 H -0.1385 1.1430 0.1839 0.067 Uiso 1 1 calc R . .
S3 S 0.4165(12) 0.6745(7) 0.2927(3) 0.093(3) Uiso 1 1 d . . .
O12 O 0.388(2) 0.3754(14) 0.3803(6) 0.070(5) Uiso 1 1 d . . .
C36 C 0.352(3) 0.564(2) 0.3871(9) 0.056(7) Uiso 1 1 d . . .
O11 O 0.299(2) 0.4262(14) 0.2172(7) 0.081(5) Uiso 1 1 d . . .
C38 C 0.361(3) 0.4710(18) 0.3562(9) 0.045(6) Uiso 1 1 d . . .
C37 C 0.333(3) 0.488(2) 0.3022(10) 0.065(7) Uiso 1 1 d . . .
O9 O 0.343(2) 0.7811(14) 0.2687(6) 0.074(5) Uiso 1 1 d . . .
N8 N 0.348(2) 0.3029(15) 0.2882(7) 0.055(5) Uiso 1 1 d . . .
H17 H 0.3619 0.2922 0.3219 0.066 Uiso 1 1 calc R . .
N9 N 0.327(2) 0.2276(16) 0.2099(8) 0.060(6) Uiso 1 1 d . . .
H22 H 0.3135 0.2894 0.1933 0.071 Uiso 1 1 calc R . .
C41 C 0.362(3) 0.113(2) 0.2899(11) 0.065(7) Uiso 1 1 d . . .
H18 H 0.3692 0.1027 0.3266 0.078 Uiso 1 1 calc R . .
C35 C 0.376(4) 0.661(3) 0.3604(12) 0.086(9) Uiso 1 1 d . . .
N7 N 0.285(3) 0.5989(19) 0.2774(9) 0.081(7) Uiso 1 1 d . . .
C40 C 0.350(3) 0.216(2) 0.2615(10) 0.055(7) Uiso 1 1 d . . .
C39 C 0.326(3) 0.406(2) 0.2662(10) 0.063(7) Uiso 1 1 d . . .
O10 O 0.608(3) 0.6321(15) 0.2815(7) 0.089(6) Uiso 1 1 d . . .
C44 C 0.323(3) 0.1441(18) 0.1829(9) 0.047(6) Uiso 1 1 d . . .
H21 H 0.3127 0.1553 0.1463 0.056 Uiso 1 1 calc R . .
C43 C 0.334(3) 0.043(2) 0.2064(10) 0.061(7) Uiso 1 1 d . . .
H20 H 0.3227 -0.0141 0.1873 0.073 Uiso 1 1 calc R . .
C33 C 0.326(4) 0.743(3) 0.4472(12) 0.092(9) Uiso 1 1 d . . .
H14 H 0.3092 0.7993 0.4671 0.111 Uiso 1 1 calc R . .
C32 C 0.328(3) 0.639(2) 0.4690(11) 0.070(8) Uiso 1 1 d . . .
H15 H 0.3119 0.6282 0.5054 0.084 Uiso 1 1 calc R . .
C42 C 0.362(3) 0.031(2) 0.2608(10) 0.065(7) Uiso 1 1 d . . .
H19 H 0.3815 -0.0366 0.2780 0.078 Uiso 1 1 calc R . .
C31 C 0.351(3) 0.549(2) 0.4415(9) 0.059(7) Uiso 1 1 d . . .
H16 H 0.3652 0.4820 0.4594 0.071 Uiso 1 1 calc R . .
C34 C 0.353(5) 0.753(3) 0.3935(16) 0.130(13) Uiso 1 1 d . . .
H13 H 0.3561 0.8200 0.3765 0.156 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
O13 C50 1.41(3) . ?
O13 H44 0.90(2) . ?
C46 N7 1.53(3) . ?
C46 H23 0.9600 . ?
C46 H25 0.9600 . ?
C46 H24 0.9600 . ?
C50 H40 0.9600 . ?
C50 H41 0.9600 . ?
C50 H39 0.9600 . ?
C30 C27 1.35(3) . ?
C30 C26 1.43(3) . ?
C30 H29 0.9300 . ?
S2 O6 1.392(15) . ?
S2 O7 1.474(17) . ?
S2 N4 1.62(2) . ?
S2 C19 1.73(3) . ?
O8 C24 1.27(2) . ?
N4 C23 1.50(3) . ?
N4 C29 1.54(3) . ?
N5 C25 1.38(3) . ?
N5 C24 1.40(3) . ?
N5 H31 0.8600 . ?
N6 C25 1.34(3) . ?
N6 C28 1.35(3) . ?
N6 H26 0.8600 . ?
O5 C22 1.32(2) . ?
C23 C22 1.35(3) . ?
C23 C24 1.45(3) . ?
C18 C17 1.39(3) . ?
C18 C19 1.41(3) . ?
C18 H35 0.9300 . ?
C16 C17 1.44(3) . ?
C16 C21 1.46(3) . ?
C16 H33 0.9300 . ?
C27 C28 1.41(3) . ?
C27 H28 0.9300 . ?
C20 C21 1.32(3) . ?
C20 C19 1.47(3) . ?
C20 C22 1.52(3) . ?
C26 C25 1.41(3) . ?
C26 H30 0.9300 . ?
C28 H27 0.9300 . ?
C17 H34 0.9300 . ?
C21 H32 0.9300 . ?
C29 H36 0.9600 . ?
C29 H37 0.9600 . ?
C29 H38 0.9600 . ?
S1 O3 1.390(15) . ?
S1 O4 1.450(16) . ?
S1 N1 1.608(19) . ?
S1 C6 1.74(3) . ?
O2 C9 1.29(3) . ?
C6 C1 1.42(3) . ?
C6 C5 1.46(3) . ?
C8 C7 1.38(3) . ?
C8 N1 1.47(3) . ?
C8 C9 1.47(3) . ?
N1 C15 1.54(3) . ?
N2 C9 1.33(3) . ?
N2 C10 1.45(3) . ?
N2 H5 0.8600 . ?
C2 C3 1.36(3) . ?
C2 C1 1.39(3) . ?
C2 H2 0.9300 . ?
O1 C7 1.35(3) . ?
O1 H42 0.8200 . ?
C7 C5 1.42(3) . ?
C10 C11 1.36(3) . ?
C10 N3 1.37(3) . ?
C15 H12 0.9600 . ?
C15 H11 0.9600 . ?
C15 H10 0.9600 . ?
C1 H1 0.9300 . ?
C3 C4 1.44(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.40(3) . ?
C4 H4 0.9300 . ?
C12 C13 1.37(3) . ?
C12 C11 1.43(3) 2_575 ?
C12 H8 0.9300 . ?
C14 N3 1.37(3) . ?
C14 C13 1.47(4) 2_575 ?
C14 H7 0.9300 . ?
C13 C14 1.47(4) 2_575 ?
C13 H9 0.9300 . ?
C11 C12 1.43(3) 2_575 ?
C11 H6 0.9300 . ?
S3 O10 1.431(18) . ?
S3 O9 1.486(17) . ?
S3 N7 1.50(2) . ?
S3 C35 1.74(3) . ?
O12 C38 1.32(2) . ?
C36 C31 1.38(3) . ?
C36 C35 1.40(3) . ?
C36 C38 1.49(3) . ?
O11 C39 1.26(3) . ?
C38 C37 1.38(3) . ?
C37 C39 1.47(3) . ?
C37 N7 1.51(3) . ?
N8 C40 1.37(3) . ?
N8 C39 1.38(3) . ?
N8 H17 0.8600 . ?
N9 C40 1.32(3) . ?
N9 C44 1.34(3) . ?
N9 H22 0.8600 . ?
C41 C42 1.35(3) . ?
C41 C40 1.45(3) . ?
C41 H18 0.9300 . ?
C35 C34 1.52(4) . ?
C44 C43 1.38(3) . ?
C44 H21 0.9300 . ?
C43 C42 1.39(3) . ?
C43 H20 0.9300 . ?
C33 C34 1.37(4) . ?
C33 C32 1.39(3) . ?
C33 H14 0.9300 . ?
C32 C31 1.41(3) . ?
C32 H15 0.9300 . ?
C42 H19 0.9300 . ?
C31 H16 0.9300 . ?
C34 H13 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
C50 O13 H44 121(10) . . ?
N7 C46 H23 109.5 . . ?
N7 C46 H25 109.5 . . ?
H23 C46 H25 109.5 . . ?
N7 C46 H24 109.5 . . ?
H23 C46 H24 109.5 . . ?
H25 C46 H24 109.5 . . ?
O13 C50 H40 109.5 . . ?
O13 C50 H41 109.5 . . ?
H40 C50 H41 109.5 . . ?
O13 C50 H39 109.5 . . ?
H40 C50 H39 109.5 . . ?
H41 C50 H39 109.5 . . ?
C27 C30 C26 122(3) . . ?
C27 C30 H29 119.0 . . ?
C26 C30 H29 119.0 . . ?
O6 S2 O7 119.1(9) . . ?
O6 S2 N4 110.7(11) . . ?
O7 S2 N4 106.5(10) . . ?
O6 S2 C19 103.2(11) . . ?
O7 S2 C19 111.0(12) . . ?
N4 S2 C19 105.7(11) . . ?
C23 N4 C29 112.6(16) . . ?
C23 N4 S2 111.7(15) . . ?
C29 N4 S2 121.1(17) . . ?
C25 N5 C24 125(2) . . ?
C25 N5 H31 117.6 . . ?
C24 N5 H31 117.6 . . ?
C25 N6 C28 124(2) . . ?
C25 N6 H26 118.0 . . ?
C28 N6 H26 118.0 . . ?
C22 C23 C24 125(2) . . ?
C22 C23 N4 122(2) . . ?
C24 C23 N4 113(2) . . ?
C17 C18 C19 123(2) . . ?
C17 C18 H35 118.6 . . ?
C19 C18 H35 118.6 . . ?
C17 C16 C21 119(2) . . ?
C17 C16 H33 120.4 . . ?
C21 C16 H33 120.4 . . ?
O8 C24 N5 122(2) . . ?
O8 C24 C23 125(2) . . ?
N5 C24 C23 112(2) . . ?
C30 C27 C28 119(3) . . ?
C30 C27 H28 120.7 . . ?
C28 C27 H28 120.7 . . ?
C21 C20 C19 122(3) . . ?
C21 C20 C22 119(2) . . ?
C19 C20 C22 117(2) . . ?
O5 C22 C23 125(2) . . ?
O5 C22 C20 113(2) . . ?
C23 C22 C20 122(2) . . ?
C25 C26 C30 117(2) . . ?
C25 C26 H30 121.6 . . ?
C30 C26 H30 121.6 . . ?
N6 C28 C27 119(3) . . ?
N6 C28 H27 120.4 . . ?
C27 C28 H27 120.4 . . ?
C18 C17 C16 118(2) . . ?
C18 C17 H34 120.9 . . ?
C16 C17 H34 120.9 . . ?
C20 C21 C16 120(3) . . ?
C20 C21 H32 120.1 . . ?
C16 C21 H32 120.1 . . ?
N4 C29 H36 109.5 . . ?
N4 C29 H37 109.5 . . ?
H36 C29 H37 109.5 . . ?
N4 C29 H38 109.5 . . ?
H36 C29 H38 109.5 . . ?
H37 C29 H38 109.5 . . ?
C18 C19 C20 115(2) . . ?
C18 C19 S2 123.2(19) . . ?
C20 C19 S2 119(2) . . ?
N6 C25 N5 120(2) . . ?
N6 C25 C26 119(2) . . ?
N5 C25 C26 120(2) . . ?
O3 S1 O4 116.1(9) . . ?
O3 S1 N1 109.5(10) . . ?
O4 S1 N1 109.2(10) . . ?
O3 S1 C6 110.3(11) . . ?
O4 S1 C6 108.5(12) . . ?
N1 S1 C6 102.3(12) . . ?
C1 C6 C5 121(2) . . ?
C1 C6 S1 123(2) . . ?
C5 C6 S1 116.1(19) . . ?
C7 C8 N1 119(2) . . ?
C7 C8 C9 124(2) . . ?
N1 C8 C9 117(2) . . ?
C8 N1 C15 115.1(18) . . ?
C8 N1 S1 112.0(16) . . ?
C15 N1 S1 116.8(16) . . ?
C9 N2 C10 126(2) . . ?
C9 N2 H5 117.1 . . ?
C10 N2 H5 117.1 . . ?
C3 C2 C1 121(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C7 O1 H42 109.5 . . ?
O1 C7 C8 120(2) . . ?
O1 C7 C5 115(2) . . ?
C8 C7 C5 125(2) . . ?
C11 C10 N3 126(2) . . ?
C11 C10 N2 126(2) . . ?
N3 C10 N2 107(2) . . ?
N1 C15 H12 109.5 . . ?
N1 C15 H11 109.5 . . ?
H12 C15 H11 109.5 . . ?
N1 C15 H10 109.5 . . ?
H12 C15 H10 109.5 . . ?
H11 C15 H10 109.5 . . ?
C2 C1 C6 120(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C2 C3 C4 122(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C4 C5 C7 124(2) . . ?
C4 C5 C6 117(2) . . ?
C7 C5 C6 119(2) . . ?
C5 C4 C3 120(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C13 C12 C11 118(3) . 2_575 ?
C13 C12 H8 121.2 . . ?
C11 C12 H8 121.2 2_575 . ?
O2 C9 N2 125(2) . . ?
O2 C9 C8 115(2) . . ?
N2 C9 C8 120(2) . . ?
N3 C14 C13 121(3) . 2_575 ?
N3 C14 H7 119.7 . . ?
C13 C14 H7 119.7 2_575 . ?
C10 N3 C14 116(2) . . ?
C12 C13 C14 121(3) . 2_575 ?
C12 C13 H9 119.8 . . ?
C14 C13 H9 119.7 2_575 . ?
C10 C11 C12 119(2) . 2_575 ?
C10 C11 H6 120.7 . . ?
C12 C11 H6 120.7 2_575 . ?
O10 S3 O9 119.5(11) . . ?
O10 S3 N7 107.6(14) . . ?
O9 S3 N7 108.2(12) . . ?
O10 S3 C35 109.9(13) . . ?
O9 S3 C35 111.1(14) . . ?
N7 S3 C35 98.3(13) . . ?
C31 C36 C35 121(3) . . ?
C31 C36 C38 120(2) . . ?
C35 C36 C38 119(2) . . ?
O12 C38 C37 121(2) . . ?
O12 C38 C36 120(2) . . ?
C37 C38 C36 119(2) . . ?
C38 C37 C39 126(2) . . ?
C38 C37 N7 118(2) . . ?
C39 C37 N7 115(2) . . ?
C40 N8 C39 126(2) . . ?
C40 N8 H17 116.9 . . ?
C39 N8 H17 116.9 . . ?
C40 N9 C44 121(2) . . ?
C40 N9 H22 119.5 . . ?
C44 N9 H22 119.5 . . ?
C42 C41 C40 117(2) . . ?
C42 C41 H18 121.5 . . ?
C40 C41 H18 121.5 . . ?
C36 C35 C34 116(3) . . ?
C36 C35 S3 121(2) . . ?
C34 C35 S3 123(3) . . ?
S3 N7 C37 114.5(17) . . ?
S3 N7 C46 122.4(19) . . ?
C37 N7 C46 111.7(18) . . ?
N9 C40 N8 120(2) . . ?
N9 C40 C41 120(2) . . ?
N8 C40 C41 120(2) . . ?
O11 C39 N8 120(3) . . ?
O11 C39 C37 123(2) . . ?
N8 C39 C37 117(2) . . ?
N9 C44 C43 124(2) . . ?
N9 C44 H21 118.2 . . ?
C43 C44 H21 118.2 . . ?
C44 C43 C42 115(3) . . ?
C44 C43 H20 122.5 . . ?
C42 C43 H20 122.5 . . ?
C34 C33 C32 114(3) . . ?
C34 C33 H14 123.1 . . ?
C32 C33 H14 123.1 . . ?
C33 C32 C31 127(3) . . ?
C33 C32 H15 116.7 . . ?
C31 C32 H15 116.7 . . ?
C41 C42 C43 123(3) . . ?
C41 C42 H19 118.3 . . ?
C43 C42 H19 118.3 . . ?
C36 C31 C32 118(2) . . ?
C36 C31 H16 121.2 . . ?
C32 C31 H16 121.2 . . ?
C33 C34 C35 124(4) . . ?
C33 C34 H13 118.2 . . ?
C35 C34 H13 118.2 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        20.82
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.498
_refine_diff_density_min         -1.383
_refine_diff_density_rms         0.192
