#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:37:51 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180479 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/48/7214865.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7214865
loop_
_publ_author_name
'Wales, Craig'
'Thomas, Lynne H.'
'Wilson, Chick C.'
_publ_section_title
;
 Tautomerisation and polymorphism in molecular complexes of piroxicam with
 mono-substituted benzoic acids
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              7264
_journal_paper_doi               10.1039/c2ce26069g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         '2(C15 H13 N3 O4 S), C8 H8 O2, C2 H3 N'
_chemical_formula_sum            'C40 H37 N7 O10 S2'
_chemical_formula_weight         839.91
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.6020(10)
_cell_angle_beta                 104.0920(10)
_cell_angle_gamma                112.1530(10)
_cell_formula_units_Z            1
_cell_length_a                   8.4985(2)
_cell_length_b                   9.8813(2)
_cell_length_c                   12.5408(3)
_cell_measurement_reflns_used    19901
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      1
_cell_volume                     931.91(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo & Scalepack(Otwinowski,Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1337
_diffrn_reflns_av_sigmaI/netI    0.0785
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19882
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             438
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0625P)²+0.6583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                2874
_reflns_number_total             4108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26069g.txt
_cod_data_source_block           shelxl_PXZ_3MBA_ACN
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7214865
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C17 C 0.8146(10) 0.4544(9) 0.8813(5) 0.0242(6) Uani 0.50 1 d P
H17 H 0.8066 0.4604 0.8066 0.029 Uiso 0.50 1 calc PR
C18 C 0.9820(11) 0.5017(9) 0.9591(5) 0.0242(6) Uani 0.50 1 d P
H18 H 1.0832 0.5390 0.9354 0.029 Uiso 0.50 1 calc PR
O6 O 1.4620(7) 0.6521(6) 0.8306(4) 0.0240(11) Uani 0.50 1 d P
C24 C 1.4883(10) 0.6632(8) 0.9412(6) 0.0204(9) Uani 0.50 1 d P
O5 O 0.3635(6) 0.2832(6) 0.9933(4) 0.0474(13) Uani 0.50 1 d P
C21 C 1.1578(7) 0.5594(6) 0.8967(5) 0.0242(6) Uani 0.50 1 d P
H21 H 1.1506 0.5634 0.8219 0.029 Uiso 0.50 1 calc PR
C22 C 1.3236(7) 0.6062(6) 0.9746(4) 0.0204(9) Uani 0.50 1 d P
C20 C 0.6622(7) 0.3994(6) 0.9131(5) 0.0242(6) Uani 0.50 1 d P
H20 H 0.5516 0.3665 0.8606 0.029 Uiso 0.50 1 calc PR
N4 N 0.4181(8) 0.2841(7) 0.9253(6) 0.0465(13) Uani 0.50 1 d P
C25 C 1.4128(12) 0.6273(11) 0.8652(8) 0.035(2) Uani 0.50 1 d P
H25A H 1.4942 0.6581 0.8214 0.052 Uiso 0.50 1 calc PR
H25B H 1.3264 0.6689 0.8455 0.052 Uiso 0.50 1 calc PR
H25C H 1.3539 0.5210 0.8511 0.052 Uiso 0.50 1 calc PR
C23 C 0.8249(10) 0.4616(9) 0.8473(5) 0.0242(6) Uani 0.50 1 d P
H23A H 0.7765 0.5324 0.8604 0.036 Uiso 0.50 1 calc PR
H23B H 0.7471 0.3654 0.8555 0.036 Uiso 0.50 1 calc PR
H23C H 0.8365 0.4578 0.7730 0.036 Uiso 0.50 1 calc PR
C26 C 1.5086(15) 0.6779(12) 0.9819(8) 0.0465(13) Uani 0.50 1 d P
C19 C 1.0010(10) 0.5062(9) 0.9288(6) 0.0242(6) Uani 0.50 1 d P
H4 H -0.206(4) 0.603(3) 0.374(2) 0.020(7) Uiso 1 1 d .
H3 H -0.492(4) 0.582(3) 0.310(3) 0.025(8) Uiso 1 1 d .
H13 H 0.245(4) 1.092(3) 0.709(2) 0.023(7) Uiso 1 1 d .
H1 H -0.467(4) 0.749(3) 0.626(2) 0.019(7) Uiso 1 1 d .
H6 H -0.084(4) 0.794(3) 1.113(2) 0.015(7) Uiso 1 1 d .
H7 H 0.041(3) 0.822(3) 1.303(2) 0.013(6) Uiso 1 1 d .
H5 H -0.045(4) 0.828(3) 0.928(3) 0.031(8) Uiso 1 1 d .
H2 H -0.627(4) 0.652(3) 0.439(2) 0.029(8) Uiso 1 1 d .
H11 H 0.248(4) 1.021(4) 0.588(3) 0.040(9) Uiso 1 1 d .
H9 H 0.514(4) 1.014(3) 1.244(2) 0.018(7) Uiso 1 1 d .
H12 H 0.069(4) 1.027(3) 0.603(3) 0.035(9) Uiso 1 1 d .
H10 H 0.392(4) 0.979(4) 1.065(3) 0.037(9) Uiso 1 1 d .
H8 H 0.357(4) 0.929(3) 1.373(3) 0.035(9) Uiso 1 1 d .
H24 H 1.559(12) 0.699(9) 0.824(7) 0.06(3) Uiso 0.50 1 d P
S1 S 0.06613(8) 0.72291(8) 0.58149(5) 0.0210(2) Uani 1 1 d .
O1 O -0.2276(2) 0.7768(2) 0.79940(15) 0.0224(4) Uani 1 1 d .
O2 O 0.3257(2) 0.9383(2) 0.90460(15) 0.0232(4) Uani 1 1 d .
N3 N 0.0705(3) 0.8712(2) 0.95697(18) 0.0185(5) Uani 1 1 d .
O4 O 0.1521(2) 0.7652(2) 0.49601(15) 0.0278(5) Uani 1 1 d .
O3 O 0.0754(2) 0.6005(2) 0.63263(16) 0.0261(5) Uani 1 1 d .
C8 C 0.0501(3) 0.8470(3) 0.7632(2) 0.0184(5) Uani 1 1 d .
N2 N 0.3199(3) 0.9503(3) 1.11321(18) 0.0202(5) Uani 1 1 d .
N1 N 0.1453(3) 0.8691(2) 0.68005(17) 0.0194(5) Uani 1 1 d .
C7 C -0.1352(3) 0.7901(3) 0.7304(2) 0.0184(6) Uani 1 1 d .
C6 C -0.2335(3) 0.7376(3) 0.6083(2) 0.0188(6) Uani 1 1 d .
C4 C -0.2523(4) 0.6401(3) 0.4199(2) 0.0216(6) Uani 1 1 d .
C12 C 0.0362(4) 0.8384(3) 1.1404(2) 0.0210(6) Uani 1 1 d .
C15 C 0.3998(4) 0.9686(3) 1.2242(2) 0.0227(6) Uani 1 1 d .
C14 C 0.3012(4) 0.9200(3) 1.2958(2) 0.0248(6) Uani 1 1 d .
C5 C -0.1578(3) 0.6974(3) 0.5311(2) 0.0204(6) Uani 1 1 d .
C9 C 0.1616(3) 0.8896(3) 0.8765(2) 0.0189(6) Uani 1 1 d .
C2 C -0.5055(4) 0.6659(3) 0.4582(2) 0.0237(6) Uani 1 1 d .
C11 C 0.1427(3) 0.8870(3) 1.0691(2) 0.0172(5) Uani 1 1 d .
C16 C 0.1818(4) 1.0139(3) 0.6426(2) 0.0239(6) Uani 1 1 d .
C3 C -0.4280(4) 0.6245(3) 0.3841(2) 0.0253(6) Uani 1 1 d .
C13 C 0.1153(4) 0.8525(3) 1.2521(2) 0.0235(6) Uani 1 1 d .
C1 C -0.4106(3) 0.7203(3) 0.5701(2) 0.0213(6) Uani 1 1 d .
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'
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
C20 C17 C18 121.2(5) . .
C20 C17 H17 119.4 . .
C18 C17 H17 119.4 . .
C19 C18 C17 121.0(5) 2_767 .
C19 C18 H18 119.5 2_767 .
C17 C18 H18 119.5 . .
C24 O6 H24 104(6) . .
O5 C24 O6 121.9(7) 2_767 .
O5 C24 C22 124.0(7) 2_767 .
O6 C24 C22 114.2(7) . .
O6 C24 N4 161.5(7) . 2_767
C22 C24 N4 83.4(5) . 2_767
C22 C21 C19 121.4(5) . .
C22 C21 H21 119.3 . .
C19 C21 H21 119.3 . .
C20 C22 C21 120.4(5) 2_767 .
C20 C22 C24 118.2(5) 2_767 .
C21 C22 C24 121.4(5) . .
C17 C20 C22 118.7(6) . 2_767
C17 C20 H20 120.6 . .
C22 C20 H20 120.6 2_767 .
C26 C25 H25A 109.5 . .
C26 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C26 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C26 C25 H24 96(3) . .
H25B C25 H24 111.0 . .
H25C C25 H24 120.0 . .
C19 C23 H23A 109.5 . .
C19 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C19 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
O5 C26 N4 60.1(7) 2_767 2_767
O5 C26 C25 121.0(10) 2_767 .
N4 C26 C25 178.7(11) 2_767 .
C18 C19 C21 117.3(5) 2_767 .
C18 C19 C23 121.0(5) 2_767 .
C21 C19 C23 121.7(6) . .
O3 S1 O4 119.46(12) . .
O3 S1 N1 108.18(11) . .
O4 S1 N1 107.58(12) . .
O3 S1 C5 109.50(12) . .
O4 S1 C5 109.21(12) . .
N1 S1 C5 101.35(12) . .
C11 N3 C9 126.2(2) . .
C11 N3 H5 120(2) . .
C9 N3 H5 113(2) . .
C7 C8 C9 125.3(2) . .
C7 C8 N1 120.2(2) . .
C9 C8 N1 114.5(2) . .
C11 N2 C15 122.4(2) . .
C11 N2 H10 119(2) . .
C15 N2 H10 119(2) . .
C8 N1 C16 113.8(2) . .
C8 N1 S1 112.74(17) . .
C16 N1 S1 116.34(18) . .
O1 C7 C8 123.5(2) . .
O1 C7 C6 117.7(2) . .
C8 C7 C6 118.8(2) . .
C5 C6 C1 118.0(2) . .
C5 C6 C7 122.3(2) . .
C1 C6 C7 119.5(2) . .
C5 C4 C3 118.5(3) . .
C5 C4 H4 120.5(18) . .
C3 C4 H4 120.5(18) . .
C13 C12 C11 119.3(3) . .
C13 C12 H6 119.5(17) . .
C11 C12 H6 121.1(17) . .
N2 C15 C14 120.6(3) . .
N2 C15 H9 114.6(19) . .
C14 C15 H9 124.8(19) . .
C15 C14 C13 118.4(3) . .
C15 C14 H8 121(2) . .
C13 C14 H8 121(2) . .
C4 C5 C6 122.2(2) . .
C4 C5 S1 120.9(2) . .
C6 C5 S1 116.9(2) . .
O2 C9 N3 120.5(2) . .
O2 C9 C8 124.8(2) . .
N3 C9 C8 114.7(2) . .
C3 C2 C1 120.5(3) . .
C3 C2 H2 123.7(18) . .
C1 C2 H2 115.7(18) . .
N2 C11 N3 119.7(2) . .
N2 C11 C12 118.8(2) . .
N3 C11 C12 121.5(2) . .
N1 C16 H13 107.6(16) . .
N1 C16 H11 108.5(19) . .
H13 C16 H11 114(3) . .
N1 C16 H12 113.2(18) . .
H13 C16 H12 107(2) . .
H11 C16 H12 106(3) . .
C2 C3 C4 120.5(3) . .
C2 C3 H3 121.3(18) . .
C4 C3 H3 118.1(18) . .
C12 C13 C14 120.4(3) . .
C12 C13 H7 119.5(16) . .
C14 C13 H7 119.9(15) . .
C2 C1 C6 120.2(3) . .
C2 C1 H1 121.5(15) . .
C6 C1 H1 118.3(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C17 C20 1.371(9) .
C17 C18 1.400(9) .
C17 H17 0.9300 .
C18 C19 1.388(7) 2_767
C18 H18 0.9300 .
O6 C24 1.340(9) .
O6 H24 0.81(9) .
C24 O5 1.217(9) 2_767
C24 C22 1.474(9) .
C24 N4 1.624(9) 2_767
O5 C26 0.965(11) 2_767
O5 C24 1.217(9) 2_767
C21 C22 1.392(8) .
C21 C19 1.404(9) .
C21 H21 0.9300 .
C22 C20 1.389(8) 2_767
C20 C22 1.389(8) 2_767
C20 H20 0.9300 .
N4 C26 1.140(11) 2_767
N4 C24 1.624(9) 2_767
C25 C26 1.440(12) .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C23 C19 1.476(9) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C26 O5 0.965(10) 2_767
C26 N4 1.140(11) 2_767
C19 C18 1.388(7) 2_767
S1 O3 1.423(2) .
S1 O4 1.437(2) .
S1 N1 1.645(2) .
S1 C5 1.765(3) .
O1 C7 1.284(3) .
O2 C9 1.239(3) .
N3 C11 1.363(3) .
N3 C9 1.395(3) .
N3 H5 0.88(3) .
C8 C7 1.397(3) .
C8 C9 1.436(4) .
C8 N1 1.448(3) .
N2 C11 1.344(3) .
N2 C15 1.359(3) .
N2 H10 0.95(3) .
N1 C16 1.478(4) .
C7 C6 1.504(4) .
C6 C5 1.399(4) .
C6 C1 1.403(4) .
C4 C5 1.387(4) .
C4 C3 1.395(4) .
C4 H4 0.90(3) .
C12 C13 1.372(4) .
C12 C11 1.403(4) .
C12 H6 0.91(3) .
C15 C14 1.362(4) .
C15 H9 0.87(3) .
C14 C13 1.407(4) .
C14 H8 0.95(3) .
C2 C3 1.384(4) .
C2 C1 1.391(4) .
C2 H2 0.95(3) .
C16 H13 0.98(3) .
C16 H11 0.98(3) .
C16 H12 1.02(3) .
C3 H3 0.93(3) .
C13 H7 0.98(3) .
C1 H1 1.02(3) .
