#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/40/4504058.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_4504058
loop_
_publ_author_name
'Childs, Scott L.'
'Hardcastle, Kenneth I.'
_publ_section_title
;
 Cocrystals of Piroxicam with Carboxylic Acids
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1291
_journal_paper_doi               10.1021/cg060742p
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C15 H13 N3 O4 S, C7 H6 O3'
_chemical_formula_sum            'C22 H19 N3 O7 S'
_chemical_formula_weight         469.46
_chemical_name_common
'piroxicam:4-hydroxybenzoic acid cocrystal, Form 1 (1:1)'
_chemical_name_systematic
;

 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine
 -3-carboxamide-1,1-dioxide 4-hydroxybenzoic acid

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.561(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3201(10)
_cell_length_b                   16.4366(17)
_cell_length_c                   14.2134(15)
_cell_measurement_reflns_used    7132
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.42
_cell_volume                     2140.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31316
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9511
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10, Sheldrick 2003'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irreg
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+1.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                4791
_reflns_number_total             5328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060742psi20061021_092419.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4504058
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'
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
C1 C 0.85887(18) 0.19027(10) 0.16807(11) 0.0222(3) Uani 1 1 d .
C2 C 0.99900(18) 0.20812(10) 0.20973(11) 0.0228(3) Uani 1 1 d .
C3 C 1.10882(18) 0.23340(10) 0.15439(12) 0.0232(3) Uani 1 1 d .
C4 C 1.2336(2) 0.27568(12) 0.19670(13) 0.0293(4) Uani 1 1 d .
H4 H 1.2522 0.2852 0.2638 0.035 Uiso 1 1 calc R
C5 C 1.3306(2) 0.30374(13) 0.14123(15) 0.0353(4) Uani 1 1 d .
H5A H 1.4152 0.3327 0.1706 0.042 Uiso 1 1 calc R
C6 C 1.3060(2) 0.29017(13) 0.04363(15) 0.0355(4) Uani 1 1 d .
H6A H 1.3725 0.3109 0.0063 0.043 Uiso 1 1 calc R
C7 C 1.1842(2) 0.24625(12) -0.00024(13) 0.0290(4) Uani 1 1 d .
H7 H 1.1676 0.2359 -0.0671 0.035 Uiso 1 1 calc R
C8 C 1.08810(18) 0.21809(10) 0.05569(12) 0.0232(3) Uani 1 1 d .
C9 C 0.75309(19) 0.16513(11) 0.22645(12) 0.0245(3) Uani 1 1 d .
C10 C 0.50343(18) 0.10799(11) 0.21297(13) 0.0249(3) Uani 1 1 d .
C11 C 0.4944(2) 0.10623(13) 0.30953(14) 0.0337(4) Uani 1 1 d .
H11 H 0.5688 0.1291 0.3567 0.040 Uiso 1 1 calc R
C12 C 0.3730(2) 0.06993(14) 0.33409(15) 0.0400(5) Uani 1 1 d .
H12 H 0.3625 0.0678 0.3993 0.048 Uiso 1 1 calc R
C13 C 0.2668(2) 0.03664(14) 0.26411(16) 0.0400(5) Uani 1 1 d .
H13 H 0.1839 0.0103 0.2804 0.048 Uiso 1 1 calc R
C14 C 0.2839(2) 0.04262(13) 0.17048(15) 0.0350(4) Uani 1 1 d .
H14 H 0.2103 0.0205 0.1221 0.042 Uiso 1 1 calc R
C15 C 0.7375(2) 0.26915(12) 0.02791(14) 0.0335(4) Uani 1 1 d .
H15A H 0.6623 0.2831 0.0652 0.050 Uiso 1 1 calc R
H15B H 0.6919 0.2611 -0.0393 0.050 Uiso 1 1 calc R
H15C H 0.8088 0.3134 0.0326 0.050 Uiso 1 1 calc R
C16 C 0.88602(19) 0.41284(11) 0.38868(13) 0.0268(4) Uani 1 1 d .
C17 C 0.7465(2) 0.44489(12) 0.38398(13) 0.0289(4) Uani 1 1 d .
H17 H 0.7091 0.4538 0.4410 0.035 Uiso 1 1 calc R
C18 C 0.6628(2) 0.46363(12) 0.29622(13) 0.0286(4) Uani 1 1 d .
H18 H 0.5672 0.4848 0.2932 0.034 Uiso 1 1 calc R
C19 C 0.71660(19) 0.45187(11) 0.21199(12) 0.0256(4) Uani 1 1 d .
C20 C 0.85668(19) 0.41998(11) 0.21761(13) 0.0271(4) Uani 1 1 d .
H20 H 0.8949 0.4120 0.1608 0.032 Uiso 1 1 calc R
C21 C 0.94018(19) 0.39991(11) 0.30506(13) 0.0275(4) Uani 1 1 d .
H21 H 1.0347 0.3773 0.3081 0.033 Uiso 1 1 calc R
C22 C 0.62494(19) 0.47415(11) 0.11970(12) 0.0263(4) Uani 1 1 d .
N1 N 0.81194(15) 0.19340(9) 0.06592(10) 0.0230(3) Uani 1 1 d .
N2 N 0.62161(16) 0.14075(9) 0.17706(10) 0.0256(3) Uani 1 1 d .
H2N H 0.6169 0.1356 0.1159 0.031 Uiso 1 1 d R
N3 N 0.39977(16) 0.07825(10) 0.14426(11) 0.0273(3) Uani 1 1 d .
O1 O 1.04527(14) 0.20440(9) 0.30432(8) 0.0300(3) Uani 1 1 d .
H1O H 0.9635 0.1924 0.3287 0.064(9) Uiso 1 1 d R
O2 O 0.96501(14) 0.07643(8) 0.03668(10) 0.0314(3) Uani 1 1 d .
O3 O 0.89015(15) 0.17666(10) -0.09170(9) 0.0369(3) Uani 1 1 d .
O4 O 0.78408(14) 0.16692(9) 0.31514(9) 0.0321(3) Uani 1 1 d .
O5 O 0.97273(15) 0.39412(10) 0.47260(10) 0.0375(3) Uani 1 1 d .
H5 H 0.9302 0.4063 0.5179 0.056 Uiso 1 1 calc R
O6 O 0.68635(16) 0.46708(10) 0.04466(9) 0.0386(3) Uani 1 1 d .
H6 H 0.6243 0.4762 -0.0050 0.058 Uiso 1 1 calc R
O7 O 0.49800(15) 0.49743(10) 0.11425(10) 0.0392(4) Uani 1 1 d .
S1 S 0.93577(5) 0.15838(3) 0.00741(3) 0.02363(11) 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
C2 C1 N1 121.36(15)
C2 C1 C9 120.47(15)
N1 C1 C9 118.15(14)
O1 C2 C1 122.27(15)
O1 C2 C3 115.22(14)
C1 C2 C3 122.50(15)
C4 C3 C8 118.16(16)
C4 C3 C2 121.43(16)
C8 C3 C2 120.37(15)
C5 C4 C3 120.10(17)
C5 C4 H4 119.9
C3 C4 H4 119.9
C6 C5 C4 120.85(17)
C6 C5 H5A 119.6
C4 C5 H5A 119.6
C5 C6 C7 120.32(17)
C5 C6 H6A 119.8
C7 C6 H6A 119.8
C8 C7 C6 118.50(17)
C8 C7 H7 120.7
C6 C7 H7 120.7
C7 C8 C3 122.01(16)
C7 C8 S1 121.64(13)
C3 C8 S1 116.33(13)
O4 C9 N2 123.56(16)
O4 C9 C1 121.00(15)
N2 C9 C1 115.44(15)
N3 C10 C11 123.22(17)
N3 C10 N2 112.69(15)
C11 C10 N2 124.09(16)
C12 C11 C10 117.37(18)
C12 C11 H11 121.3
C10 C11 H11 121.3
C11 C12 C13 120.13(19)
C11 C12 H12 119.9
C13 C12 H12 119.9
C14 C13 C12 118.32(19)
C14 C13 H13 120.8
C12 C13 H13 120.8
N3 C14 C13 122.94(18)
N3 C14 H14 118.5
C13 C14 H14 118.5
N1 C15 H15A 109.5
N1 C15 H15B 109.5
H15A C15 H15B 109.5
N1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O5 C16 C21 117.96(16)
O5 C16 C17 122.11(17)
C21 C16 C17 119.92(16)
C18 C17 C16 119.73(17)
C18 C17 H17 120.1
C16 C17 H17 120.1
C17 C18 C19 120.86(17)
C17 C18 H18 119.6
C19 C18 H18 119.6
C18 C19 C20 118.89(16)
C18 C19 C22 119.27(16)
C20 C19 C22 121.84(16)
C21 C20 C19 120.57(17)
C21 C20 H20 119.7
C19 C20 H20 119.7
C20 C21 C16 120.01(16)
C20 C21 H21 120.0
C16 C21 H21 120.0
O7 C22 O6 122.43(16)
O7 C22 C19 121.74(16)
O6 C22 C19 115.83(16)
C1 N1 C15 115.75(14)
C1 N1 S1 112.71(11)
C15 N1 S1 115.83(12)
C9 N2 C10 128.31(15)
C9 N2 H2N 115.0
C10 N2 H2N 115.4
C10 N3 C14 117.96(16)
C2 O1 H1O 104.7
C16 O5 H5 109.5
C22 O6 H6 109.5
O2 S1 O3 119.66(9)
O2 S1 N1 107.35(8)
O3 S1 N1 108.40(8)
O2 S1 C8 108.48(8)
O3 S1 C8 109.93(8)
N1 S1 C8 101.45(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.363(2)
C1 N1 1.438(2)
C1 C9 1.460(2)
C2 O1 1.3360(19)
C2 C3 1.461(2)
C3 C4 1.393(2)
C3 C8 1.403(2)
C4 C5 1.383(3)
C4 H4 0.9500
C5 C6 1.382(3)
C5 H5A 0.9500
C6 C7 1.393(3)
C6 H6A 0.9500
C7 C8 1.382(2)
C7 H7 0.9500
C8 S1 1.7584(17)
C9 O4 1.241(2)
C9 N2 1.356(2)
C10 N3 1.334(2)
C10 C11 1.391(3)
C10 N2 1.403(2)
C11 C12 1.379(3)
C11 H11 0.9500
C12 C13 1.381(3)
C12 H12 0.9500
C13 C14 1.373(3)
C13 H13 0.9500
C14 N3 1.340(2)
C14 H14 0.9500
C15 N1 1.479(2)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 O5 1.348(2)
C16 C21 1.390(3)
C16 C17 1.393(2)
C17 C18 1.379(2)
C17 H17 0.9500
C18 C19 1.394(2)
C18 H18 0.9500
C19 C20 1.395(2)
C19 C22 1.474(2)
C20 C21 1.380(2)
C20 H20 0.9500
C21 H21 0.9500
C22 O7 1.232(2)
C22 O6 1.305(2)
N1 S1 1.6452(15)
N2 H2N 0.8673
O1 H1O 0.9140
O2 S1 1.4214(14)
O3 S1 1.4270(13)
O5 H5 0.8400
O6 H6 0.8400
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 N3 0.84 1.89 2.689(2) 159.5 4_666
N2 H2N O5 0.87 2.28 3.0367(19) 146.2 4_565
N2 H2N N1 0.87 2.28 2.724(2) 112.0 .
O6 H6 O7 0.84 1.80 2.6404(19) 174.9 3_665
O1 H1O O4 0.91 1.70 2.5429(18) 151.8 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 C2 O1 -178.98(15)
C9 C1 C2 O1 -0.7(3)
N1 C1 C2 C3 1.6(3)
C9 C1 C2 C3 179.90(15)
O1 C2 C3 C4 -20.4(2)
C1 C2 C3 C4 159.07(17)
O1 C2 C3 C8 161.99(15)
C1 C2 C3 C8 -18.6(3)
C8 C3 C4 C5 2.2(3)
C2 C3 C4 C5 -175.50(17)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C7 -1.4(3)
C5 C6 C7 C8 1.1(3)
C6 C7 C8 C3 0.9(3)
C6 C7 C8 S1 -177.20(15)
C4 C3 C8 C7 -2.5(3)
C2 C3 C8 C7 175.20(16)
C4 C3 C8 S1 175.65(13)
C2 C3 C8 S1 -6.6(2)
C2 C1 C9 O4 6.9(3)
N1 C1 C9 O4 -174.74(16)
C2 C1 C9 N2 -173.40(16)
N1 C1 C9 N2 4.9(2)
N3 C10 C11 C12 1.6(3)
N2 C10 C11 C12 -178.24(18)
C10 C11 C12 C13 0.4(3)
C11 C12 C13 C14 -1.6(3)
C12 C13 C14 N3 0.9(3)
O5 C16 C17 C18 179.43(18)
C21 C16 C17 C18 0.0(3)
C16 C17 C18 C19 -0.8(3)
C17 C18 C19 C20 0.6(3)
C17 C18 C19 C22 -178.81(17)
C18 C19 C20 C21 0.4(3)
C22 C19 C20 C21 179.80(17)
C19 C20 C21 C16 -1.2(3)
O5 C16 C21 C20 -178.46(17)
C17 C16 C21 C20 1.0(3)
C18 C19 C22 O7 -5.3(3)
C20 C19 C22 O7 175.33(18)
C18 C19 C22 O6 175.15(17)
C20 C19 C22 O6 -4.2(3)
C2 C1 N1 C15 -97.4(2)
C9 C1 N1 C15 84.25(19)
C2 C1 N1 S1 39.1(2)
C9 C1 N1 S1 -139.19(14)
O4 C9 N2 C10 -5.4(3)
C1 C9 N2 C10 174.91(16)
N3 C10 N2 C9 -169.70(17)
C11 C10 N2 C9 10.2(3)
C11 C10 N3 C14 -2.3(3)
N2 C10 N3 C14 177.57(16)
C13 C14 N3 C10 1.0(3)
C1 N1 S1 O2 59.20(13)
C15 N1 S1 O2 -164.27(12)
C1 N1 S1 O3 -170.23(12)
C15 N1 S1 O3 -33.70(15)
C1 N1 S1 C8 -54.51(13)
C15 N1 S1 C8 82.02(14)
C7 C8 S1 O2 105.07(16)
C3 C8 S1 O2 -73.11(15)
C7 C8 S1 O3 -27.49(18)
C3 C8 S1 O3 154.34(13)
C7 C8 S1 N1 -142.08(15)
C3 C8 S1 N1 39.75(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661443
2 PubChem 67150286
