An aceto­nitrile-solvated cocrystal of piroxicam and succinic acid with co-existing zwitterionic and non-ionized piroxicam mol­ecules

Liu, X.; Michalchuk, A.A.L.; Pulham, C.R.; Boldyreva, E.V.

doi:10.1107/S2053229618016911

An acetonitrile-solvated cocrystal of piroxicam and succinic acid with co-existing zwitterionic and non-ionized piroxicam molecules

X. Liu, A. A. L. Michalchuk, C. R. Pulham and E. V. Boldyreva

This work reports a new acetonitrile (ACN)-solvated cocrystal of piroxicam (PRX) and succinic acid (SA), 2C₁₅H₁₃N₃O₄S·0.5C₄H₆O₄·C₂H₃N or PRX:SA:ACN (4:1:2), which adopts the triclinic space group P $\overline{1}$ . The outcome of crystallization from ACN solution can be controlled by varying only the PRX:SA ratio, with a higher PRX:SA ratio in solution unexpectedly favouring a lower stoichiometric ratio in the solid product. In the new solvate, zwitterionic (Z) and non-ionized (NI) PRX molecules co-exist in the asymmetric unit. In contrast, the nonsolvated PRX–SA cocrystal contains only NI-type PRX molecules. The ACN molecule entrapped in PRX–SA·ACN does not form any hydrogen bonds with the surrounding molecules. In the solvated cocrystal, Z-type molecules form dimers linked by intermolecular N—H

O hydrogen bonds, whereas every pair of NI-type molecules is linked to SA via N—H

O and O—H

N hydrogen bonds. Thermogravimetry and differential scanning calorimetry suggest that thermal desolvation of the solvate sample occurs at 148 °C, and is followed by recrystallization, presumably of a multicomponent PRX–SA structure. Vibrational spectra (IR and Raman spectroscopy) of PRX–SA·ACN and PRX–SA are also used to demonstrate the ability of spectroscopic techniques to distinguish between NI- and Z-type PRX molecules in the solid state. Hence, vibrational spectroscopy can be used to distinguish the PRX–SA cocrystal and its ACN solvate.

Keywords: piroxicam; succinic acid; crystal structure; cocrystal; solvate.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618016911/ku3231sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618016911/ku3231Isup2.hkl Contains datablock I
	Text file https://doi.org/10.1107/S2053229618016911/ku3231sup3.txt CIF file of cocrystal
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618016911/ku3231sup4.pdf Additional figures, hydrogen-bond geometry and spectra

CCDC reference: 1860488

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4-Hydroxy-2-methyl-N-(pyridin-2-yl)-2H-1,2-benzothiazine-3-\ carboxamide 1,1-dioxide–succinic acid–acetonitrile (4/1/2) top

Crystal data top

4C₁₅H₁₃N₃O₄S·C₄H₆O₄·2C₂H₃N	Z = 1
M_r = 1525.57	F(000) = 794
Triclinic, P1	D_x = 1.499 Mg m⁻³
a = 9.1561 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.7660 (5) Å	Cell parameters from 11463 reflections
c = 15.1022 (5) Å	θ = 4.0–29.3°
α = 83.030 (3)°	µ = 0.23 mm⁻¹
β = 75.313 (3)°	T = 120 K
γ = 83.972 (3)°	Block, clear yellowish yellow
V = 1689.87 (11) Å³	0.44 × 0.16 × 0.09 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Atlas detector	6505 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	R_int = 0.047
Mirror monochromator	θ_max = 29.8°, θ_min = 2.9°
Detector resolution: 5.1574 pixels mm^-1	h = −12→11
ω scans	k = −16→17
30897 measured reflections	l = −20→19
8512 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0488P)² + 0.6069P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
8512 reflections	Δρ_max = 0.43 e Å⁻³
501 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints

Special details top

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.56249 (5)	0.51097 (4)	0.81566 (3)	0.01718 (11)
S1A	0.51996 (5)	0.95151 (4)	0.20324 (3)	0.01738 (11)
O2A	0.35755 (14)	0.89787 (10)	0.49328 (8)	0.0189 (3)
O1	0.85023 (13)	0.54236 (10)	0.55856 (8)	0.0178 (3)
O1A	0.63606 (13)	0.84018 (10)	0.49432 (8)	0.0191 (3)
O3A	0.52506 (14)	0.83890 (10)	0.20667 (9)	0.0218 (3)
O4	0.61816 (14)	0.52241 (11)	0.89421 (9)	0.0246 (3)
O2	0.38987 (13)	0.63539 (10)	0.58349 (8)	0.0204 (3)
O3	0.55616 (14)	0.40694 (10)	0.79172 (9)	0.0228 (3)
O5	0.91844 (14)	0.95196 (11)	0.16737 (9)	0.0246 (3)
O6	1.11296 (16)	0.83233 (12)	0.12959 (10)	0.0294 (3)
O4A	0.56602 (14)	1.01347 (11)	0.11726 (9)	0.0259 (3)
N1A	1.06678 (15)	0.79626 (11)	0.31394 (10)	0.0166 (3)
N2	0.66103 (17)	0.59141 (12)	0.48374 (10)	0.0169 (3)
N1	0.89245 (16)	0.55523 (12)	0.37868 (10)	0.0157 (3)
N3A	0.61791 (15)	0.97913 (12)	0.27301 (10)	0.0161 (3)
N3	0.66282 (16)	0.57882 (12)	0.72692 (10)	0.0165 (3)
N2A	0.82028 (15)	0.86478 (12)	0.35951 (11)	0.0156 (3)
C6	0.34274 (18)	0.62285 (13)	0.74572 (12)	0.0154 (3)
C10A	0.94686 (18)	0.80958 (13)	0.38521 (12)	0.0142 (3)
C7	0.44819 (19)	0.61706 (13)	0.65212 (11)	0.0154 (3)
C10	0.74555 (19)	0.59175 (14)	0.39554 (12)	0.0160 (3)
C9A	0.67602 (18)	0.87595 (13)	0.41232 (12)	0.0149 (3)
C8	0.60287 (19)	0.58837 (14)	0.64623 (11)	0.0154 (3)
C6A	0.30083 (18)	0.98616 (14)	0.35675 (12)	0.0158 (3)
C7A	0.41397 (18)	0.93752 (13)	0.40644 (12)	0.0151 (3)
C8A	0.56444 (18)	0.93173 (13)	0.36512 (12)	0.0148 (3)
C14A	1.19510 (19)	0.74678 (14)	0.33108 (13)	0.0199 (4)
H14A	1.2788	0.7381	0.2819	0.024*
C9	0.71416 (19)	0.57116 (13)	0.56295 (12)	0.0154 (3)
C3A	0.0904 (2)	1.08212 (14)	0.26020 (14)	0.0214 (4)
H3A	0.0199	1.1141	0.2286	0.026*
C5	0.19658 (19)	0.67127 (14)	0.75407 (12)	0.0182 (4)
H5	0.1665	0.7012	0.7016	0.022*
C11A	0.95027 (19)	0.77222 (14)	0.47520 (12)	0.0166 (3)
H11A	0.8654	0.7814	0.5236	0.020*
C1A	0.33696 (18)	0.99931 (14)	0.26045 (12)	0.0167 (3)
C1	0.38137 (19)	0.57745 (14)	0.82679 (12)	0.0171 (4)
C16	1.01926 (19)	0.91257 (15)	0.10927 (12)	0.0203 (4)
C12	0.7771 (2)	0.63371 (15)	0.23344 (13)	0.0215 (4)
H12	0.7380	0.6610	0.1836	0.026*
C12A	1.0841 (2)	0.72088 (14)	0.49062 (13)	0.0196 (4)
H12A	1.0898	0.6949	0.5500	0.023*
C4A	0.05204 (19)	1.06884 (14)	0.35496 (14)	0.0207 (4)
H4A	−0.0445	1.0922	0.3868	0.025*
C4	0.0957 (2)	0.67538 (15)	0.83937 (13)	0.0216 (4)
H4	−0.0009	0.7086	0.8436	0.026*
C2A	0.2346 (2)	1.04773 (14)	0.21159 (13)	0.0202 (4)
H2AC	0.2617	1.0571	0.1477	0.024*
C11	0.6857 (2)	0.63191 (15)	0.32054 (12)	0.0192 (4)
H11	0.5845	0.6572	0.3299	0.023*
C13	0.9296 (2)	0.59466 (15)	0.21870 (12)	0.0213 (4)
H13	0.9920	0.5955	0.1595	0.026*
C14	0.9839 (2)	0.55563 (15)	0.29280 (12)	0.0194 (4)
H14	1.0845	0.5290	0.2845	0.023*
C5A	0.15555 (19)	1.02107 (14)	0.40357 (13)	0.0185 (4)
H5A	0.1278	1.0124	0.4675	0.022*
C17	1.0507 (2)	0.95073 (16)	0.00934 (13)	0.0239 (4)
H17A	1.0347	0.8950	−0.0247	0.029*
H17B	1.1558	0.9666	−0.0124	0.029*
C2	0.2816 (2)	0.58051 (16)	0.91262 (13)	0.0231 (4)
H2A	0.3106	0.5498	0.9652	0.028*
C15	0.7219 (2)	0.67557 (16)	0.74421 (14)	0.0258 (4)
H15A	0.6406	0.7298	0.7568	0.039*
H15B	0.7976	0.6994	0.6910	0.039*
H15C	0.7659	0.6605	0.7961	0.039*
C13A	1.2085 (2)	0.70835 (14)	0.41802 (14)	0.0217 (4)
H13A	1.2992	0.6748	0.4275	0.026*
C15A	0.6571 (2)	1.08983 (15)	0.26579 (14)	0.0219 (4)
H15D	0.6980	1.1138	0.2024	0.033*
H15E	0.7311	1.0936	0.3002	0.033*
H15F	0.5678	1.1339	0.2901	0.033*
C3	0.1373 (2)	0.63041 (16)	0.91858 (13)	0.0252 (4)
H3	0.0688	0.6336	0.9756	0.030*
C18	0.6546 (3)	0.75781 (19)	0.00166 (14)	0.0364 (5)
C19	0.4929 (3)	0.76025 (19)	0.01312 (15)	0.0348 (5)
H19A	0.4702	0.7040	−0.0169	0.052*
H19B	0.4571	0.8270	−0.0136	0.052*
H19C	0.4439	0.7514	0.0775	0.052*
N4	0.7818 (3)	0.7562 (2)	−0.00821 (16)	0.0619 (7)
H6	1.093 (3)	0.819 (2)	0.191 (2)	0.049 (8)*
H2AB	0.837 (2)	0.8879 (17)	0.3023 (16)	0.022 (5)*
H1	0.928 (2)	0.5362 (16)	0.4253 (15)	0.020 (5)*
H2	0.565 (2)	0.6139 (16)	0.4959 (14)	0.020 (5)*
H2AA	0.438 (3)	0.872 (2)	0.5126 (18)	0.050 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0155 (2)	0.0214 (2)	0.0137 (2)	0.00247 (16)	−0.00492 (16)	0.00131 (16)
S1A	0.0146 (2)	0.0221 (2)	0.0146 (2)	−0.00002 (16)	−0.00349 (16)	0.00032 (17)
O2A	0.0148 (6)	0.0251 (7)	0.0152 (6)	−0.0006 (5)	−0.0022 (5)	0.0012 (5)
O1	0.0151 (6)	0.0217 (7)	0.0156 (6)	0.0001 (5)	−0.0039 (5)	0.0008 (5)
O1A	0.0170 (6)	0.0231 (7)	0.0155 (6)	−0.0003 (5)	−0.0035 (5)	0.0021 (5)
O3A	0.0218 (6)	0.0227 (7)	0.0212 (7)	0.0012 (5)	−0.0051 (5)	−0.0056 (5)
O4	0.0213 (6)	0.0384 (8)	0.0142 (6)	0.0031 (6)	−0.0083 (5)	0.0007 (6)
O2	0.0183 (6)	0.0282 (7)	0.0159 (6)	0.0005 (5)	−0.0085 (5)	−0.0001 (5)
O3	0.0243 (6)	0.0185 (7)	0.0237 (7)	0.0020 (5)	−0.0058 (5)	0.0027 (5)
O5	0.0193 (6)	0.0352 (8)	0.0149 (6)	0.0046 (5)	−0.0008 (5)	0.0013 (6)
O6	0.0316 (7)	0.0323 (8)	0.0175 (7)	0.0106 (6)	−0.0010 (6)	0.0023 (6)
O4A	0.0198 (6)	0.0375 (8)	0.0177 (7)	−0.0016 (6)	−0.0041 (5)	0.0059 (6)
N1A	0.0142 (7)	0.0159 (7)	0.0192 (7)	−0.0003 (5)	−0.0039 (6)	−0.0006 (6)
N2	0.0156 (7)	0.0212 (8)	0.0142 (7)	−0.0005 (6)	−0.0049 (6)	−0.0013 (6)
N1	0.0168 (7)	0.0173 (8)	0.0135 (7)	−0.0002 (6)	−0.0059 (6)	0.0000 (6)
N3A	0.0129 (7)	0.0184 (8)	0.0162 (7)	−0.0020 (5)	−0.0043 (6)	0.0035 (6)
N3	0.0159 (7)	0.0207 (8)	0.0134 (7)	−0.0013 (6)	−0.0055 (6)	−0.0003 (6)
N2A	0.0143 (7)	0.0176 (8)	0.0143 (8)	0.0002 (5)	−0.0044 (6)	0.0018 (6)
C6	0.0161 (8)	0.0153 (9)	0.0155 (8)	−0.0010 (6)	−0.0055 (7)	−0.0012 (7)
C10A	0.0130 (7)	0.0130 (8)	0.0174 (8)	−0.0018 (6)	−0.0051 (6)	−0.0011 (6)
C7	0.0187 (8)	0.0147 (8)	0.0131 (8)	−0.0019 (6)	−0.0055 (7)	0.0009 (6)
C10	0.0179 (8)	0.0145 (9)	0.0162 (8)	−0.0031 (6)	−0.0047 (7)	−0.0008 (6)
C9A	0.0143 (8)	0.0138 (8)	0.0172 (8)	−0.0018 (6)	−0.0049 (7)	−0.0012 (6)
C8	0.0162 (8)	0.0176 (9)	0.0132 (8)	−0.0016 (6)	−0.0062 (7)	0.0014 (6)
C6A	0.0123 (8)	0.0151 (8)	0.0201 (9)	−0.0016 (6)	−0.0039 (7)	−0.0018 (7)
C7A	0.0161 (8)	0.0146 (8)	0.0148 (8)	−0.0017 (6)	−0.0035 (7)	−0.0021 (6)
C8A	0.0145 (8)	0.0154 (9)	0.0150 (8)	−0.0008 (6)	−0.0050 (6)	−0.0003 (6)
C14A	0.0148 (8)	0.0174 (9)	0.0279 (10)	0.0000 (7)	−0.0067 (7)	−0.0020 (7)
C9	0.0177 (8)	0.0120 (8)	0.0169 (8)	−0.0025 (6)	−0.0054 (7)	0.0003 (6)
C3A	0.0165 (8)	0.0181 (9)	0.0315 (11)	−0.0004 (7)	−0.0111 (8)	0.0002 (8)
C5	0.0177 (8)	0.0176 (9)	0.0197 (9)	0.0008 (7)	−0.0079 (7)	0.0010 (7)
C11A	0.0181 (8)	0.0167 (9)	0.0155 (8)	−0.0019 (7)	−0.0047 (7)	−0.0013 (7)
C1A	0.0142 (8)	0.0167 (9)	0.0196 (9)	−0.0021 (6)	−0.0051 (7)	−0.0008 (7)
C1	0.0155 (8)	0.0174 (9)	0.0183 (9)	0.0006 (6)	−0.0054 (7)	−0.0003 (7)
C16	0.0164 (8)	0.0249 (10)	0.0185 (9)	−0.0025 (7)	−0.0029 (7)	0.0001 (7)
C12	0.0254 (9)	0.0234 (10)	0.0178 (9)	−0.0027 (7)	−0.0103 (8)	0.0019 (7)
C12A	0.0229 (9)	0.0167 (9)	0.0220 (9)	−0.0015 (7)	−0.0121 (7)	0.0012 (7)
C4A	0.0130 (8)	0.0187 (9)	0.0314 (11)	−0.0003 (7)	−0.0063 (7)	−0.0051 (8)
C4	0.0154 (8)	0.0237 (10)	0.0249 (10)	0.0033 (7)	−0.0045 (7)	−0.0041 (8)
C2A	0.0207 (9)	0.0198 (9)	0.0211 (9)	−0.0030 (7)	−0.0085 (7)	0.0022 (7)
C11	0.0190 (8)	0.0210 (9)	0.0191 (9)	−0.0012 (7)	−0.0081 (7)	−0.0010 (7)
C13	0.0230 (9)	0.0260 (10)	0.0141 (9)	−0.0054 (7)	−0.0019 (7)	−0.0015 (7)
C14	0.0179 (8)	0.0214 (9)	0.0178 (9)	−0.0019 (7)	−0.0027 (7)	−0.0011 (7)
C5A	0.0146 (8)	0.0191 (9)	0.0213 (9)	−0.0022 (7)	−0.0025 (7)	−0.0038 (7)
C17	0.0224 (9)	0.0298 (11)	0.0157 (9)	0.0022 (8)	−0.0007 (7)	0.0011 (8)
C2	0.0206 (9)	0.0324 (11)	0.0151 (9)	0.0034 (8)	−0.0050 (7)	−0.0010 (8)
C15	0.0303 (10)	0.0261 (11)	0.0257 (10)	−0.0075 (8)	−0.0133 (8)	−0.0018 (8)
C13A	0.0176 (8)	0.0172 (9)	0.0328 (11)	0.0018 (7)	−0.0130 (8)	−0.0009 (8)
C15A	0.0186 (8)	0.0202 (10)	0.0265 (10)	−0.0045 (7)	−0.0064 (8)	0.0034 (8)
C3	0.0193 (9)	0.0345 (12)	0.0183 (9)	0.0035 (8)	−0.0003 (7)	−0.0022 (8)
C18	0.0418 (13)	0.0415 (14)	0.0211 (11)	0.0069 (10)	−0.0023 (9)	−0.0051 (9)
C19	0.0411 (12)	0.0364 (13)	0.0269 (11)	−0.0051 (10)	−0.0098 (10)	0.0016 (9)
N4	0.0391 (13)	0.093 (2)	0.0449 (14)	0.0120 (12)	0.0023 (10)	−0.0163 (13)

Geometric parameters (Å, º) top

S1—O4	1.4327 (13)	C6—C1	1.402 (2)
S1—O3	1.4287 (14)	C10A—C11A	1.392 (2)
S1—N3	1.6283 (15)	C7—C8	1.408 (2)
S1—C1	1.7597 (17)	C10—C11	1.400 (2)
S1A—O3A	1.4285 (14)	C9A—C8A	1.467 (2)
S1A—O4A	1.4258 (13)	C8—C9	1.428 (2)
S1A—N3A	1.6354 (15)	C6A—C7A	1.472 (2)
S1A—C1A	1.7622 (18)	C6A—C1A	1.400 (2)
O2A—C7A	1.339 (2)	C6A—C5A	1.394 (2)
O1—C9	1.249 (2)	C7A—C8A	1.359 (2)
O1A—C9A	1.243 (2)	C14A—C13A	1.376 (3)
O2—C7	1.269 (2)	C3A—C4A	1.378 (3)
O5—C16	1.214 (2)	C3A—C2A	1.393 (3)
O6—C16	1.324 (2)	C5—C4	1.385 (3)
N1A—C10A	1.341 (2)	C11A—C12A	1.387 (2)
N1A—C14A	1.344 (2)	C1A—C2A	1.387 (2)
N2—C10	1.360 (2)	C1—C2	1.386 (3)
N2—C9	1.389 (2)	C16—C17	1.493 (3)
N1—C10	1.347 (2)	C12—C11	1.368 (3)
N1—C14	1.354 (2)	C12—C13	1.404 (3)
N3A—C8A	1.433 (2)	C12A—C13A	1.377 (3)
N3A—C15A	1.479 (2)	C4A—C5A	1.390 (2)
N3—C8	1.446 (2)	C4—C3	1.387 (3)
N3—C15	1.475 (2)	C13—C14	1.357 (2)
N2A—C10A	1.407 (2)	C17—C17ⁱ	1.524 (4)
N2A—C9A	1.362 (2)	C2—C3	1.392 (2)
C6—C7	1.501 (2)	C18—C19	1.444 (3)
C6—C5	1.396 (2)	C18—N4	1.135 (3)

O4—S1—N3	108.25 (8)	C1A—C6A—C7A	120.63 (15)
O4—S1—C1	109.80 (8)	C5A—C6A—C7A	121.38 (16)
O3—S1—O4	118.80 (8)	C5A—C6A—C1A	117.99 (15)
O3—S1—N3	108.52 (8)	O2A—C7A—C6A	115.32 (14)
O3—S1—C1	108.08 (8)	O2A—C7A—C8A	123.16 (15)
N3—S1—C1	102.09 (8)	C8A—C7A—C6A	121.50 (15)
O3A—S1A—N3A	107.47 (8)	N3A—C8A—C9A	118.19 (14)
O3A—S1A—C1A	108.85 (8)	C7A—C8A—N3A	120.38 (14)
O4A—S1A—O3A	120.15 (8)	C7A—C8A—C9A	121.42 (15)
O4A—S1A—N3A	108.97 (8)	N1A—C14A—C13A	123.07 (17)
O4A—S1A—C1A	109.22 (8)	O1—C9—N2	120.79 (16)
N3A—S1A—C1A	100.36 (8)	O1—C9—C8	124.47 (15)
C10A—N1A—C14A	118.27 (15)	N2—C9—C8	114.73 (14)
C10—N2—C9	126.60 (15)	C4A—C3A—C2A	120.16 (16)
C10—N1—C14	122.92 (15)	C4—C5—C6	120.97 (16)
C8A—N3A—S1A	112.74 (11)	C12A—C11A—C10A	118.00 (16)
C8A—N3A—C15A	114.87 (14)	C6A—C1A—S1A	116.90 (12)
C15A—N3A—S1A	117.03 (11)	C2A—C1A—S1A	121.03 (14)
C8—N3—S1	113.83 (11)	C2A—C1A—C6A	122.07 (16)
C8—N3—C15	115.29 (14)	C6—C1—S1	117.16 (13)
C15—N3—S1	116.95 (12)	C2—C1—S1	120.23 (13)
C9A—N2A—C10A	127.38 (15)	C2—C1—C6	122.57 (15)
C5—C6—C7	119.74 (15)	O5—C16—O6	122.55 (17)
C5—C6—C1	117.19 (16)	O5—C16—C17	123.48 (16)
C1—C6—C7	123.01 (15)	O6—C16—C17	113.97 (16)
N1A—C10A—N2A	113.35 (15)	C11—C12—C13	120.56 (16)
N1A—C10A—C11A	122.36 (15)	C13A—C12A—C11A	120.02 (16)
C11A—C10A—N2A	124.29 (16)	C3A—C4A—C5A	120.92 (17)
O2—C7—C6	117.07 (14)	C5—C4—C3	120.63 (16)
O2—C7—C8	124.47 (16)	C1A—C2A—C3A	118.66 (17)
C8—C7—C6	118.43 (14)	C12—C11—C10	119.53 (16)
N2—C10—C11	121.94 (15)	C14—C13—C12	118.47 (17)
N1—C10—N2	119.85 (15)	N1—C14—C13	120.33 (16)
N1—C10—C11	118.19 (16)	C4A—C5A—C6A	120.18 (17)
O1A—C9A—N2A	124.25 (15)	C16—C17—C17ⁱ	111.9 (2)
O1A—C9A—C8A	120.33 (15)	C1—C2—C3	118.74 (16)
N2A—C9A—C8A	115.40 (15)	C14A—C13A—C12A	118.27 (16)
C7—C8—N3	120.94 (15)	C4—C3—C2	119.89 (17)
C7—C8—C9	124.80 (15)	N4—C18—C19	179.3 (3)
C9—C8—N3	114.20 (14)

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11A—H11A···O1A	0.93	2.29	2.869 (2)	120
C15—H15C···O4	0.96	2.45	2.843 (2)	105
C15A—H15D···O4A	0.96	2.50	2.886 (2)	104
O6—H6···N1A	0.89 (3)	1.81 (3)	2.697 (2)	176 (3)
N2A—H2AB···O5	0.86 (2)	2.08 (2)	2.927 (2)	168.8 (19)
N2A—H2AB···N3A	0.86 (2)	2.33 (2)	2.7326 (19)	109.1 (16)
N1—H1···O1	0.85 (2)	1.97 (2)	2.6322 (19)	134.5 (18)
N1—H1···O1ⁱⁱ	0.85 (2)	2.22 (2)	2.8690 (18)	132.9 (18)
N2—H2···O2	0.88 (2)	1.82 (2)	2.6009 (19)	147.1 (19)
O2A—H2AA···O1A	0.88 (3)	1.78 (3)	2.5823 (17)	152 (3)

Symmetry code: (ii) −x+2, −y+1, −z+1.

Crystallographic data for PRX–SA and PRX–SA·ACN at 120 K top

Compound	PRX-SA	PRX-SA·ACN
Chemical formula in the asymmetric unit	C₁₅H₁₃N₃O₄S.0.5C₄H₆O₄	2C₁₅H₁₃N₃O₄S·0.5C₄H₆O₄·2C₂H₃N
Formula weight	390.39	762.16
Crystal system	Triclinic	Triclinic
Space group	P1	P1
a (Å)	7.6779 (9)	9.156 (3)
b (Å)	8.4177 (9)	12.7660 (5)
c (Å)	14.3934 (10)	15.1022 (5)
α (°)	79.528 (8)	83.030 (3)
β (°)	74.650 (8)	75.313 (3)
γ (°)	72.820 (10)	83.972 (3)
V (Å³)	851.61 (16)	1689.87 (11)
Z	2	2
Density (calc) (Mg m^-3)	1.522	1.499
Crystal colour	colourless	yellow
Radiation type	Cu Kα	Mo Kα
Theta range (°)	5.5180–74.1820	4.0350–29.3170
hkl range	-9 < h < 9, -9 < k < 10, -17 < l <17	-12 < h < 11, -16 < k < 17, -20 < l < 19
Completeness (%)	99	100
R_int (%)	5.46	4.73
Refinement method	Least-squares minimization	Least-squares minimization
R[F² > 2σ(F² )] wR(F² )	R₁ = 5.48%, wR₂ = 15.38%	R₁ = 4.27%, wR₂ = 11.07%

Goodness-of-fit	1.055	1.055

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An aceto­nitrile-solvated cocrystal of piroxicam and succinic acid with co-existing zwitterionic and non-ionized piroxicam mol­ecules

Supporting information

An acetonitrile-solvated cocrystal of piroxicam and succinic acid with co-existing zwitterionic and non-ionized piroxicam molecules