#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:37:51 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180479 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/48/7214852.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_7214852
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         'C15 H13 N3 O4 S, C7 H5 Br O2'
_chemical_formula_sum            'C22 H18 Br N3 O6 S'
_chemical_formula_weight         532.36
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.575(5)
_cell_angle_beta                 105.505(6)
_cell_angle_gamma                111.738(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2526(8)
_cell_length_b                   11.0759(10)
_cell_length_c                   13.7895(18)
_cell_measurement_reflns_used    26239
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      52.95
_cell_measurement_theta_min      1
_cell_volume                     1063.1(2)
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_collection       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_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  0.0958
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26239
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         26.32
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    2.079
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0260P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                3370
_reflns_number_total             4328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26069g.txt
_cod_data_source_block           shelxl_PXN_3BRBA.
_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               7214852
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
Br1 Br 0.68780(3) 0.91856(3) 0.13748(2) 0.02272(9) Uani 1 1 d
S1 S 0.56010(8) 0.39898(6) 0.27939(5) 0.01707(14) Uani 1 1 d
O2 O 0.0429(2) 0.46715(18) -0.12764(15) 0.0226(4) Uani 1 1 d
O4 O 0.5036(2) 0.39657(16) 0.36871(13) 0.0212(4) Uani 1 1 d
O3 O 0.4509(2) 0.28518(16) 0.18151(14) 0.0234(4) Uani 1 1 d
O1 O -0.1970(2) 0.52002(17) -0.14878(14) 0.0248(4) Uani 1 1 d
O5 O 1.0152(2) 0.79474(17) 0.47926(13) 0.0188(4) Uani 1 1 d
O6 O 0.7839(2) 0.89724(16) 0.42721(13) 0.0211(4) Uani 1 1 d
N2 N 0.4796(3) 0.7535(2) 0.30850(16) 0.0155(4) Uani 1 1 d
N3 N 0.5751(2) 0.54072(19) 0.25432(15) 0.0158(4) Uani 1 1 d
N1 N 0.2116(3) 0.78297(19) 0.26229(15) 0.0166(4) Uani 1 1 d
C19 C 1.0360(3) 0.3530(3) 0.3329(2) 0.0213(6) Uani 1 1 d
C20 C 1.1724(3) 0.4857(3) 0.3945(2) 0.0198(6) Uani 1 1 d
C9 C 0.2072(3) 1.0006(3) 0.3208(2) 0.0208(6) Uani 1 1 d
C16 C 0.9342(3) 0.5658(2) 0.38073(18) 0.0153(5) Uani 1 1 d
C21 C 1.1236(3) 0.5918(3) 0.41901(19) 0.0179(5) Uani 1 1 d
C14 C 0.7111(3) 0.6670(2) 0.34043(18) 0.0149(5) Uani 1 1 d
C15 C 0.8818(3) 0.6794(2) 0.39993(18) 0.0152(5) Uani 1 1 d
C13 C 0.6630(3) 0.7819(2) 0.36218(19) 0.0168(5) Uani 1 1 d
C2 C 0.1111(3) 0.6973(2) -0.03767(19) 0.0163(5) Uani 1 1 d
C8 C 0.1203(3) 0.8614(3) 0.2661(2) 0.0192(5) Uani 1 1 d
C10 C 0.4007(4) 1.0643(3) 0.3727(2) 0.0210(6) Uani 1 1 d
C6 C 0.1724(4) 0.9287(3) 0.0520(2) 0.0211(6) Uani 1 1 d
C12 C 0.3997(3) 0.8455(2) 0.31530(18) 0.0155(5) Uani 1 1 d
C1 C -0.0292(3) 0.5540(2) -0.10951(19) 0.0171(5) Uani 1 1 d
C18 C 0.8468(3) 0.3234(3) 0.2958(2) 0.0191(6) Uani 1 1 d
C11 C 0.5006(4) 0.9873(3) 0.3705(2) 0.0192(5) Uani 1 1 d
C22 C 0.5668(4) 0.5426(3) 0.1454(2) 0.0198(5) Uani 1 1 d
C3 C 0.3024(3) 0.7329(2) 0.00673(19) 0.0173(5) Uani 1 1 d
C5 C 0.3635(4) 0.9661(3) 0.0961(2) 0.0205(6) Uani 1 1 d
C17 C 0.7974(3) 0.4292(2) 0.32026(18) 0.0164(5) Uani 1 1 d
C7 C 0.0467(4) 0.7956(3) -0.0148(2) 0.0197(6) Uani 1 1 d
C4 C 0.4253(3) 0.8673(2) 0.07354(19) 0.0184(5) Uani 1 1 d
H3 H 0.450(3) 1.061(3) 0.141(2) 0.029(7) Uiso 1 1 d
H18 H 0.680(3) 0.552(2) 0.1342(18) 0.016(6) Uiso 1 1 d
H10 H 0.409(3) 0.669(2) 0.2678(18) 0.009(6) Uiso 1 1 d
H13 H 1.300(3) 0.509(2) 0.423(2) 0.024(7) Uiso 1 1 d
H14 H 1.220(3) 0.689(3) 0.461(2) 0.027(7) Uiso 1 1 d
H8 H 0.464(3) 1.158(3) 0.411(2) 0.028(7) Uiso 1 1 d
H2 H 0.344(3) 0.667(2) -0.0068(19) 0.019(7) Uiso 1 1 d
H5 H -0.076(4) 0.773(2) -0.040(2) 0.023(7) Uiso 1 1 d
H7 H 0.132(3) 1.051(2) 0.3240(19) 0.020(6) Uiso 1 1 d
H12 H 1.068(4) 0.274(3) 0.310(2) 0.037(8) Uiso 1 1 d
H6 H -0.007(3) 0.813(2) 0.2324(19) 0.019(7) Uiso 1 1 d
H11 H 0.757(3) 0.236(3) 0.2536(19) 0.019(7) Uiso 1 1 d
H9 H 0.629(3) 1.030(2) 0.4073(19) 0.020(7) Uiso 1 1 d
H16 H 0.556(3) 0.631(3) 0.1404(19) 0.028(7) Uiso 1 1 d
H17 H 0.460(3) 0.460(3) 0.091(2) 0.024(7) Uiso 1 1 d
H4 H 0.133(4) 0.991(3) 0.065(2) 0.033(8) Uiso 1 1 d
H15 H 0.980(4) 0.857(3) 0.480(2) 0.034(8) Uiso 1 1 d
H1 H -0.048(5) 0.390(3) -0.176(3) 0.062(11) Uiso 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'
Br Br -0.2901 2.4595 '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
O4 S1 O3 119.33(10)
O4 S1 N3 108.02(10)
O3 S1 N3 108.43(10)
O4 S1 C17 108.60(10)
O3 S1 C17 109.56(10)
N3 S1 C17 101.40(10)
C1 O2 H1 107(2)
C15 O5 H15 108.5(19)
C13 N2 C12 127.1(2)
C13 N2 H10 114.1(15)
C12 N2 H10 118.8(15)
C14 N3 C22 115.20(18)
C14 N3 S1 114.80(15)
C22 N3 S1 116.73(16)
C8 N1 C12 117.8(2)
C20 C19 C18 120.4(2)
C20 C19 H12 122.7(15)
C18 C19 H12 116.9(15)
C19 C20 C21 120.8(2)
C19 C20 H13 123.2(15)
C21 C20 H13 116.0(15)
C8 C9 C10 117.8(2)
C8 C9 H7 120.0(14)
C10 C9 H7 122.2(14)
C21 C16 C17 118.0(2)
C21 C16 C15 120.7(2)
C17 C16 C15 121.3(2)
C20 C21 C16 120.2(2)
C20 C21 H14 122.3(14)
C16 C21 H14 117.4(14)
C15 C14 N3 120.6(2)
C15 C14 C13 120.8(2)
N3 C14 C13 118.66(19)
O5 C15 C14 123.3(2)
O5 C15 C16 114.5(2)
C14 C15 C16 122.2(2)
O6 C13 N2 123.2(2)
O6 C13 C14 120.4(2)
N2 C13 C14 116.4(2)
C3 C2 C7 120.2(2)
C3 C2 C1 121.3(2)
C7 C2 C1 118.5(2)
N1 C8 C9 123.9(2)
N1 C8 H6 113.9(15)
C9 C8 H6 122.1(15)
C9 C10 C11 120.1(2)
C9 C10 H8 120.0(15)
C11 C10 H8 119.8(15)
C7 C6 C5 120.5(2)
C7 C6 H4 120.1(18)
C5 C6 H4 119.4(18)
N1 C12 C11 122.3(2)
N1 C12 N2 112.9(2)
C11 C12 N2 124.8(2)
O1 C1 O2 122.5(2)
O1 C1 C2 122.6(2)
O2 C1 C2 114.9(2)
C17 C18 C19 119.0(2)
C17 C18 H11 120.5(15)
C19 C18 H11 120.5(15)
C10 C11 C12 118.1(2)
C10 C11 H9 119.3(15)
C12 C11 H9 122.5(15)
N3 C22 H18 113.5(14)
N3 C22 H16 105.7(14)
H18 C22 H16 105.2(19)
N3 C22 H17 110.4(14)
H18 C22 H17 110(2)
H16 C22 H17 112(2)
C4 C3 C2 118.5(2)
C4 C3 H2 121.4(15)
C2 C3 H2 120.1(15)
C4 C5 C6 118.9(2)
C4 C5 H3 121.8(15)
C6 C5 H3 119.2(15)
C18 C17 C16 121.6(2)
C18 C17 S1 121.70(18)
C16 C17 S1 116.69(17)
C6 C7 C2 120.1(2)
C6 C7 H5 118.7(16)
C2 C7 H5 121.2(16)
C5 C4 C3 121.8(2)
C5 C4 Br1 118.63(18)
C3 C4 Br1 119.53(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.913(2)
S1 O4 1.4303(17)
S1 O3 1.4311(17)
S1 N3 1.6420(19)
S1 C17 1.765(2)
O2 C1 1.323(3)
O2 H1 0.87(3)
O1 C1 1.218(3)
O5 C15 1.340(3)
O5 H15 0.84(3)
O6 C13 1.245(3)
N2 C13 1.376(3)
N2 C12 1.405(3)
N2 H10 0.86(2)
N3 C14 1.443(3)
N3 C22 1.490(3)
N1 C8 1.347(3)
N1 C12 1.348(3)
C19 C20 1.382(4)
C19 C18 1.391(3)
C19 H12 1.02(3)
C20 C21 1.387(3)
C20 H13 0.93(2)
C9 C8 1.373(3)
C9 C10 1.382(3)
C9 H7 0.97(2)
C16 C21 1.403(3)
C16 C17 1.409(3)
C16 C15 1.473(3)
C21 H14 1.00(3)
C14 C15 1.368(3)
C14 C13 1.468(3)
C2 C3 1.395(3)
C2 C7 1.396(3)
C2 C1 1.495(3)
C8 H6 0.91(2)
C10 C11 1.391(3)
C10 H8 0.93(3)
C6 C7 1.382(3)
C6 C5 1.389(3)
C6 H4 0.88(3)
C12 C11 1.397(3)
C18 C17 1.387(3)
C18 H11 0.91(2)
C11 H9 0.92(2)
C22 H18 0.96(2)
C22 H16 1.02(3)
C22 H17 0.98(2)
C3 C4 1.387(3)
C3 H2 0.93(2)
C5 C4 1.385(3)
C5 H3 0.97(3)
C7 H5 0.90(2)
