2-Oxo-1,2-di­hydro­quinoline-4-carb­oxy­lic acid monohydrate

Filali Baba, Y.; Mague, J.T.; Kandri Rodi, Y.; Ouzidan, Y.; Essassi, E.M.; Zouihri, H.

doi:10.1107/S2414314616009974

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160997

doi:10.1107/S2414314616009974

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2-Oxo-1,2-dihydroquinoline-4-carboxylic acid monohydrate

Yassir Filali Baba,^a Joel T. Mague,^b Youssef Kandri Rodi,^a ^* Younes Ouzidan,^a El Mokhtar Essassi ^c and Hafid Zouihri ^d

^aLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco, and ^dDépartement de Chimie, Faculté des Sciences, Université Ibn Zohr, BP 8106, Cité Dakhla, 80000 Agadir, Morocco
^*Correspondence e-mail: youssef_kandri_rodi@yahoo.fr

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 31 May 2016; accepted 19 June 2016; online 24 June 2016)

In the title compound, C₁₀H₇NO₃·H₂O, O—H⋯O hydrogen bonds involving the carboxyl groups, the keto groups and the lattice water molecules form stepped sheets approximately parallel to {010} which are tied together by pairwise N—H⋯O interactions. The asymmetric unit contains two independent quinolone derivatives and two water molecules, one of which is disordered over two positions, of equal occupancy.

Keywords: crystal structure; quinoline; hydrogen bonds.

CCDC reference: 1486461

Structure description

Quinolone derivatives are a classical division of organic chemistry; many of these molecules have shown remarkable biological properties, including exceptional antibacterial activity (Beena & Rawat, 2013 ; Chai et al., 2011 ; Hoshino et al., 2008 ). Quinolone derivatives are frequently associated with medicinal applications, such as anti-fungal (Musiol et al., 2010 ), anti-tumoral (Bergh et al., 1997 ) and anti-cancer drugs (Elderfield & LeVon, 1960 ).

The asymmetric unit contains two independent molecules, which differ primarily in the orientation of the carboxyl group. O—H⋯O hydrogen bonds involving the carboxyl groups, the keto groups and the lattice water molecules (Table 1 and Fig. 1) form stepped sheets approximately parallel to {010} in the crystal. These layers are tied together by pairwise N—H⋯O interactions (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4	0.87	1.73	2.5734 (15)	162
N1—H1⋯O1ⁱ	0.91	1.91	2.8100 (17)	169
O6—H6A⋯O7	0.87	1.68	2.5423 (17)	172
N2—H2B⋯O4ⁱⁱ	0.91	1.92	2.8229 (16)	171
O7—H7A⋯O1ⁱⁱⁱ	0.87	1.88	2.7336 (16)	165
O7—H7B⋯O8	0.87	2.01	2.841 (5)	159
O7—H7B⋯O8A	0.87	1.85	2.713 (4)	172
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) $[-x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Figure 1
The asymmetric unit of the title compound with 50% probability ellipsoids. Only one site for the disordered water molecule (O8) is shown, and O—H⋯O hydrogen bonds are depicted as dotted lines.

Figure 2
Packing structure viewed along the b axis, with O—H⋯O and N—H⋯O hydrogen bonds shown as red and blue dotted lines, respectively.

Synthesis and crystallization

To a solution of isatin (2 g, 13.6 mmol) and malonic acid (1.4 g, 13.6 mmol) in 30 ml of acetic acid was added sodium acetate (0.11 g, 1.36 mmol). The reaction mixture was refluxed for 24 h. and after cooling, 100 ml of water–ice was added. The precipitate obtained was recrystallized from water to afford colourless crystals of the title hydrate in 90% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₇NO₃·H₂O
M_r	207.18
Crystal system, space group	Monoclinic, P2/n
Temperature (K)	150
a, b, c (Å)	20.7884 (8), 3.7215 (1), 23.8849 (9)
β (°)	98.582 (2)
V (Å³)	1827.14 (11)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	1.00
Crystal size (mm)	0.18 × 0.15 × 0.04

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.85, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	12922, 3541, 2964
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.04
No. of reflections	3541
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.25
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1486461

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616009974/bh4007sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009974/bh4007Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009974/bh4007Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Oxo-1,2-dihydroquinoline-4-carboxylic acid monohydrate top

Crystal data top

C₁₀H₇NO₃·H₂O	F(000) = 864
M_r = 207.18	D_x = 1.506 Mg m⁻³
Monoclinic, P2/n	Cu Kα radiation, λ = 1.54178 Å
a = 20.7884 (8) Å	Cell parameters from 8389 reflections
b = 3.7215 (1) Å	θ = 2.6–72.2°
c = 23.8849 (9) Å	µ = 1.00 mm⁻¹
β = 98.582 (2)°	T = 150 K
V = 1827.14 (11) Å³	Plate, colourless
Z = 8	0.18 × 0.15 × 0.04 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3541 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2964 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.035
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.2°, θ_min = 3.1°
ω scans	h = −24→20
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −4→4
T_min = 0.85, T_max = 0.96	l = −29→28
12922 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: mixed
wR(F²) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0589P)² + 0.7256P] where P = (F_o² + 2F_c²)/3
3541 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³
0 constraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.05828 (5)	0.4566 (3)	0.55972 (4)	0.0263 (3)
O2	0.30022 (5)	0.0876 (3)	0.48988 (4)	0.0271 (3)
H2	0.3400	0.0624	0.5069	0.032*
O3	0.28157 (6)	−0.1782 (4)	0.57018 (5)	0.0341 (3)
N1	0.06261 (6)	0.2096 (4)	0.47364 (5)	0.0203 (3)
H1	0.0213	0.2875	0.4620	0.024*
C1	0.09018 (7)	0.2917 (4)	0.52711 (6)	0.0208 (3)
C2	0.15720 (7)	0.1848 (4)	0.54320 (6)	0.0216 (3)
H2A	0.1777	0.2205	0.5811	0.026*
C3	0.19130 (7)	0.0348 (4)	0.50521 (6)	0.0199 (3)
C4	0.16090 (7)	−0.0446 (4)	0.44812 (6)	0.0195 (3)
C5	0.19256 (8)	−0.2098 (4)	0.40645 (6)	0.0226 (3)
H5	0.2373	−0.2721	0.4150	0.027*
C6	0.15898 (8)	−0.2811 (4)	0.35347 (6)	0.0244 (3)
H6	0.1809	−0.3876	0.3255	0.029*
C7	0.09275 (8)	−0.1973 (4)	0.34063 (6)	0.0241 (3)
H7	0.0699	−0.2517	0.3041	0.029*
C8	0.06040 (8)	−0.0374 (4)	0.38018 (6)	0.0221 (3)
H8	0.0154	0.0180	0.3713	0.027*
C9	0.09468 (7)	0.0431 (4)	0.43393 (6)	0.0197 (3)
C10	0.26237 (7)	−0.0371 (4)	0.52540 (6)	0.0217 (3)
O4	0.42412 (5)	0.0548 (3)	0.52056 (4)	0.0251 (3)
O5	0.37123 (6)	0.7177 (4)	0.69734 (5)	0.0375 (3)
O6	0.45531 (6)	0.4850 (4)	0.75528 (5)	0.0347 (3)
H6A	0.4327	0.5472	0.7816	0.042*
N2	0.51852 (6)	0.2797 (4)	0.56588 (5)	0.0197 (3)
H2B	0.5374	0.1958	0.5365	0.024*
C11	0.45441 (7)	0.2135 (4)	0.56345 (6)	0.0203 (3)
C12	0.42424 (7)	0.3275 (4)	0.61097 (6)	0.0221 (3)
H12	0.3787	0.2959	0.6100	0.026*
C13	0.46007 (8)	0.4797 (4)	0.65710 (6)	0.0209 (3)
C14	0.52881 (7)	0.5455 (4)	0.65896 (6)	0.0197 (3)
C15	0.56950 (8)	0.7117 (4)	0.70415 (6)	0.0231 (3)
H15	0.5519	0.7850	0.7368	0.028*
C16	0.63443 (8)	0.7692 (4)	0.70153 (7)	0.0260 (4)
H16	0.6613	0.8780	0.7326	0.031*
C17	0.66096 (8)	0.6681 (5)	0.65332 (7)	0.0254 (3)
H17	0.7057	0.7105	0.6518	0.030*
C18	0.62274 (8)	0.5076 (4)	0.60813 (6)	0.0226 (3)
H18	0.6408	0.4413	0.5753	0.027*
C19	0.55683 (7)	0.4432 (4)	0.61111 (6)	0.0196 (3)
C20	0.42396 (8)	0.5753 (5)	0.70562 (6)	0.0245 (3)
O7	0.39711 (6)	0.7156 (4)	0.83450 (5)	0.0389 (3)
H7A	0.4043	0.6144	0.8677	0.058*
H7B	0.3549	0.7252	0.8268	0.058*
O8	0.26582 (17)	0.934 (2)	0.80246 (18)	0.0619 (19)	0.494 (12)
H8A	0.2609	1.1497	0.8152	0.093*	0.494 (12)
H8B	0.2407	0.7859	0.8173	0.093*	0.494 (12)
O8A	0.26537 (17)	0.681 (3)	0.8129 (2)	0.071 (2)	0.506 (12)
H8AA	0.2488	0.7914	0.7819	0.107*	0.506 (12)
H8AB	0.2466	0.7575	0.8408	0.107*	0.506 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0222 (6)	0.0375 (7)	0.0196 (5)	0.0065 (5)	0.0043 (4)	−0.0006 (5)
O2	0.0149 (5)	0.0434 (7)	0.0228 (5)	0.0000 (5)	0.0028 (4)	0.0026 (5)
O3	0.0236 (6)	0.0495 (8)	0.0279 (6)	0.0038 (5)	−0.0003 (5)	0.0117 (6)
N1	0.0154 (6)	0.0263 (7)	0.0192 (6)	0.0016 (5)	0.0024 (5)	0.0018 (5)
C1	0.0197 (8)	0.0250 (8)	0.0182 (7)	0.0008 (6)	0.0044 (6)	0.0030 (6)
C2	0.0193 (7)	0.0271 (8)	0.0178 (7)	−0.0001 (6)	0.0012 (5)	0.0024 (6)
C3	0.0185 (7)	0.0211 (7)	0.0195 (7)	0.0003 (6)	0.0014 (5)	0.0033 (6)
C4	0.0187 (7)	0.0204 (7)	0.0192 (7)	−0.0005 (6)	0.0025 (5)	0.0023 (6)
C5	0.0215 (8)	0.0239 (8)	0.0230 (7)	0.0014 (6)	0.0047 (6)	0.0010 (6)
C6	0.0285 (8)	0.0245 (8)	0.0209 (7)	0.0011 (6)	0.0059 (6)	−0.0002 (6)
C7	0.0286 (8)	0.0238 (8)	0.0186 (7)	−0.0021 (6)	−0.0007 (6)	0.0010 (6)
C8	0.0205 (7)	0.0240 (8)	0.0210 (7)	−0.0012 (6)	0.0002 (6)	0.0038 (6)
C9	0.0204 (7)	0.0205 (7)	0.0182 (7)	−0.0004 (6)	0.0032 (5)	0.0031 (6)
C10	0.0195 (8)	0.0256 (8)	0.0196 (7)	0.0010 (6)	0.0021 (6)	−0.0015 (6)
O4	0.0184 (5)	0.0376 (7)	0.0188 (5)	0.0002 (5)	0.0016 (4)	−0.0062 (5)
O5	0.0298 (7)	0.0586 (9)	0.0247 (6)	0.0155 (6)	0.0066 (5)	−0.0015 (6)
O6	0.0305 (7)	0.0586 (9)	0.0157 (5)	0.0077 (6)	0.0056 (5)	0.0029 (5)
N2	0.0184 (6)	0.0263 (7)	0.0150 (6)	0.0017 (5)	0.0039 (5)	−0.0008 (5)
C11	0.0196 (7)	0.0243 (8)	0.0166 (7)	0.0015 (6)	0.0017 (5)	0.0008 (6)
C12	0.0192 (7)	0.0285 (8)	0.0189 (7)	0.0024 (6)	0.0040 (6)	0.0009 (6)
C13	0.0232 (8)	0.0227 (8)	0.0169 (7)	0.0038 (6)	0.0033 (6)	0.0024 (6)
C14	0.0222 (8)	0.0192 (7)	0.0173 (7)	0.0027 (6)	0.0021 (5)	0.0020 (5)
C15	0.0281 (8)	0.0228 (8)	0.0183 (7)	0.0002 (6)	0.0031 (6)	0.0003 (6)
C16	0.0284 (9)	0.0239 (8)	0.0241 (8)	−0.0028 (6)	−0.0020 (6)	−0.0012 (6)
C17	0.0200 (8)	0.0272 (8)	0.0283 (8)	−0.0016 (6)	0.0013 (6)	0.0032 (7)
C18	0.0204 (8)	0.0257 (8)	0.0220 (7)	0.0019 (6)	0.0045 (6)	0.0012 (6)
C19	0.0213 (8)	0.0196 (7)	0.0173 (7)	0.0020 (6)	0.0014 (5)	0.0021 (6)
C20	0.0240 (8)	0.0309 (9)	0.0189 (7)	0.0007 (6)	0.0039 (6)	−0.0015 (6)
O7	0.0332 (7)	0.0630 (9)	0.0212 (6)	0.0031 (6)	0.0064 (5)	0.0029 (6)
O8	0.0327 (18)	0.080 (5)	0.075 (3)	−0.0015 (19)	0.0131 (15)	0.007 (2)
O8A	0.0355 (19)	0.098 (6)	0.080 (3)	0.009 (2)	0.0097 (17)	−0.006 (3)

Geometric parameters (Å, º) top

O1—C1	1.2558 (19)	O6—H6A	0.8703
O2—C10	1.3242 (19)	N2—C11	1.348 (2)
O2—H2	0.8700	N2—C19	1.3836 (19)
O3—C10	1.2047 (19)	N2—H2B	0.9098
N1—C1	1.3545 (19)	C11—C12	1.440 (2)
N1—C9	1.3844 (19)	C12—C13	1.358 (2)
N1—H1	0.9101	C12—H12	0.9500
C1—C2	1.445 (2)	C13—C14	1.444 (2)
C2—C3	1.353 (2)	C13—C20	1.514 (2)
C2—H2A	0.9500	C14—C19	1.410 (2)
C3—C4	1.445 (2)	C14—C15	1.411 (2)
C3—C10	1.508 (2)	C15—C16	1.377 (2)
C4—C9	1.406 (2)	C15—H15	0.9500
C4—C5	1.413 (2)	C16—C17	1.400 (2)
C5—C6	1.377 (2)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.377 (2)
C6—C7	1.400 (2)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.403 (2)
C7—C8	1.374 (2)	C18—H18	0.9500
C7—H7	0.9500	O7—H7A	0.8700
C8—C9	1.405 (2)	O7—H7B	0.8701
C8—H8	0.9500	O8—H8A	0.8700
O4—C11	1.2661 (18)	O8—H8B	0.8702
O5—C20	1.207 (2)	O8A—H8AA	0.8699
O6—C20	1.3091 (19)	O8A—H8AB	0.8700

C10—O2—H2	106.1	C11—N2—H2B	116.2
C1—N1—C9	124.59 (13)	C19—N2—H2B	119.3
C1—N1—H1	117.5	O4—C11—N2	119.30 (14)
C9—N1—H1	117.6	O4—C11—C12	123.55 (14)
O1—C1—N1	120.45 (13)	N2—C11—C12	117.15 (13)
O1—C1—C2	123.16 (13)	C13—C12—C11	120.77 (14)
N1—C1—C2	116.37 (13)	C13—C12—H12	119.6
C3—C2—C1	121.09 (13)	C11—C12—H12	119.6
C3—C2—H2A	119.5	C12—C13—C14	121.06 (14)
C1—C2—H2A	119.5	C12—C13—C20	116.39 (14)
C2—C3—C4	121.21 (14)	C14—C13—C20	122.55 (13)
C2—C3—C10	116.44 (13)	C19—C14—C15	117.74 (14)
C4—C3—C10	122.35 (14)	C19—C14—C13	117.11 (13)
C9—C4—C5	118.25 (13)	C15—C14—C13	125.13 (14)
C9—C4—C3	117.03 (14)	C16—C15—C14	120.87 (15)
C5—C4—C3	124.70 (14)	C16—C15—H15	119.6
C6—C5—C4	120.36 (15)	C14—C15—H15	119.6
C6—C5—H5	119.8	C15—C16—C17	120.29 (14)
C4—C5—H5	119.8	C15—C16—H16	119.9
C5—C6—C7	120.38 (15)	C17—C16—H16	119.9
C5—C6—H6	119.8	C18—C17—C16	120.60 (15)
C7—C6—H6	119.8	C18—C17—H17	119.7
C8—C7—C6	120.79 (14)	C16—C17—H17	119.7
C8—C7—H7	119.6	C17—C18—C19	119.20 (15)
C6—C7—H7	119.6	C17—C18—H18	120.4
C7—C8—C9	119.15 (14)	C19—C18—H18	120.4
C7—C8—H8	120.4	N2—C19—C18	119.21 (13)
C9—C8—H8	120.4	N2—C19—C14	119.49 (14)
N1—C9—C8	119.41 (14)	C18—C19—C14	121.29 (14)
N1—C9—C4	119.54 (13)	O5—C20—O6	125.33 (15)
C8—C9—C4	121.05 (14)	O5—C20—C13	121.30 (14)
O3—C10—O2	124.87 (14)	O6—C20—C13	113.37 (14)
O3—C10—C3	122.70 (14)	H7A—O7—H7B	104.1
O2—C10—C3	112.36 (12)	H8A—O8—H8B	109.5
C20—O6—H6A	109.7	H8AA—O8A—H8AB	109.5
C11—N2—C19	124.34 (13)

C9—N1—C1—O1	177.00 (14)	C19—N2—C11—O4	−178.38 (14)
C9—N1—C1—C2	−2.0 (2)	C19—N2—C11—C12	1.1 (2)
O1—C1—C2—C3	−174.35 (15)	O4—C11—C12—C13	176.50 (15)
N1—C1—C2—C3	4.6 (2)	N2—C11—C12—C13	−3.0 (2)
C1—C2—C3—C4	−3.9 (2)	C11—C12—C13—C14	2.6 (2)
C1—C2—C3—C10	174.98 (14)	C11—C12—C13—C20	−177.53 (14)
C2—C3—C4—C9	0.4 (2)	C12—C13—C14—C19	−0.4 (2)
C10—C3—C4—C9	−178.41 (14)	C20—C13—C14—C19	179.79 (14)
C2—C3—C4—C5	−178.18 (15)	C12—C13—C14—C15	177.96 (15)
C10—C3—C4—C5	3.0 (2)	C20—C13—C14—C15	−1.9 (2)
C9—C4—C5—C6	0.1 (2)	C19—C14—C15—C16	−0.4 (2)
C3—C4—C5—C6	178.66 (15)	C13—C14—C15—C16	−178.72 (15)
C4—C5—C6—C7	−1.3 (2)	C14—C15—C16—C17	1.0 (2)
C5—C6—C7—C8	1.1 (2)	C15—C16—C17—C18	−0.5 (2)
C6—C7—C8—C9	0.2 (2)	C16—C17—C18—C19	−0.6 (2)
C1—N1—C9—C8	178.27 (15)	C11—N2—C19—C18	−178.15 (14)
C1—N1—C9—C4	−1.4 (2)	C11—N2—C19—C14	1.1 (2)
C7—C8—C9—N1	178.94 (14)	C17—C18—C19—N2	−179.57 (14)
C7—C8—C9—C4	−1.4 (2)	C17—C18—C19—C14	1.2 (2)
C5—C4—C9—N1	−179.12 (14)	C15—C14—C19—N2	−179.93 (13)
C3—C4—C9—N1	2.2 (2)	C13—C14—C19—N2	−1.5 (2)
C5—C4—C9—C8	1.2 (2)	C15—C14—C19—C18	−0.7 (2)
C3—C4—C9—C8	−177.40 (14)	C13—C14—C19—C18	177.75 (14)
C2—C3—C10—O3	46.5 (2)	C12—C13—C20—O5	−43.5 (2)
C4—C3—C10—O3	−134.67 (17)	C14—C13—C20—O5	136.39 (18)
C2—C3—C10—O2	−130.40 (15)	C12—C13—C20—O6	135.88 (16)
C4—C3—C10—O2	48.4 (2)	C14—C13—C20—O6	−44.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.87	1.73	2.5734 (15)	162
N1—H1···O1ⁱ	0.91	1.91	2.8100 (17)	169
O6—H6A···O7	0.87	1.68	2.5423 (17)	172
N2—H2B···O4ⁱⁱ	0.91	1.92	2.8229 (16)	171
O7—H7A···O1ⁱⁱⁱ	0.87	1.88	2.7336 (16)	165
O7—H7B···O8	0.87	2.01	2.841 (5)	159
O7—H7B···O8A	0.87	1.85	2.713 (4)	172

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y, −z+3/2.

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