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In the title hydrated salt, C9H8NO+·C8H4NO6·H2O, the deprotonated carboxyl­ate group is almost normal to its attached benzene ring [dihedral angle = 83.56 (8)°], whereas the protonated carboxyl­ate group is close to parallel [dihedral angle = 24.56 (9)°]. In the crystal, the components are linked by N—H...O and O—H...O hydrogen bonds, generating [001] chains. The packing is consolidated by C—H...O and π–π [centroid-to-centroid distances = 3.6408 (9) and 3.6507 (9) Å] inter­actions, which result in a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901500571X/hb7385sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901500571X/hb7385Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901500571X/hb7385Isup3.cml
Supplementary material

CCDC reference: 1055171

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.060
  • wR factor = 0.176
  • Data-to-parameter ratio = 28.6

checkCIF/PLATON results

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Alert level C PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... N1 Check PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -1.917 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 9 Note PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 5 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 49 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Chemical context top

The quinoline nucleus is found in many synthetic and natural products having a wide range of pharmacological activities such as anti-viral (Font et al., 1997), and anti-inflammatory (Sloboda et al., 1991) activities.

Structural commentary top

We herewith report the crystal structure of the title compound (I), (Fig.1). The asymmetric unit of the title compound consists of C9 H8 N O+ cation, C8 H4 N O6- anion and a water molecule. The geometric parameters of the title compound are comparable to the reported structures [Castañeda et al., 2014; Kafka et al., 2012; Li & Chai (2007)]. The benzene ring (C1—C6) of anion makes the dihedral angle of 58.18 (6)° with the quinolinium ring (C9—C12/N2/C13—C17) of cation.

Supra­molecular features top

The molecular structure is stabilized by weak intra­molecular N—H···O and O—H···O hydrogen bonds (Table 1). The crystal structure is formed by weak inter­molecular N—H···O, O—H···O and C—H···O hydrogen bonds (Table 1 & Fig. 2) by linking the adjacent anions and cations by bridging water molecules through O—H···O hydrogen bonds into infinite two-dimensional network along [1 0 0] plane. The crystal structure is further stabilized by weak C—H···π (Table 1) and ππ [Cg1···Cg1i = 3.6507 (9); Cg2···Cg2ii = 3.6507 (9)Å; (i) -x,1-y,1-z; (ii) x,1/2-y,1/2+z; Cg1 and Cg2 are the centroids of the rings (C1—C6) and (N2/C12/C11/C10/C9/C13)] inter­actions.

Synthesis and crystallization top

The title compound was synthesized by taking at 1:1 ratio of 8-hy­droxy­quinoline and of 3-nitro­phthalic acid was dissolved in a mixed solvent of methanol and water. The salt was formed while adding the base instanstaouly. The solution was stirred for about 2 h to get a homogenous solution. The solution was filtered off and kept aside for slow evaporation at room temperature which yields single crystals suitable for X-ray diffraction.

Refinement top

C-bound H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms for O atoms were located from Fourier map and refined with O—H = 0.82 (1)Å and Uiso(H) = 1.5 Ueq(O). H atom for N atom was located from Fourier map and refined freely with N—H = 0.88 (1)Å.

Related literature top

For the biological activity of quinoline derivatives, see: Font et al. (1997); Sloboda et al. (1991). For similar structures, see: Castañeda et al. (2014); Kafka et al. (2012); Li & Chai (2007).

Structure description top

The quinoline nucleus is found in many synthetic and natural products having a wide range of pharmacological activities such as anti-viral (Font et al., 1997), and anti-inflammatory (Sloboda et al., 1991) activities.

We herewith report the crystal structure of the title compound (I), (Fig.1). The asymmetric unit of the title compound consists of C9 H8 N O+ cation, C8 H4 N O6- anion and a water molecule. The geometric parameters of the title compound are comparable to the reported structures [Castañeda et al., 2014; Kafka et al., 2012; Li & Chai (2007)]. The benzene ring (C1—C6) of anion makes the dihedral angle of 58.18 (6)° with the quinolinium ring (C9—C12/N2/C13—C17) of cation.

The molecular structure is stabilized by weak intra­molecular N—H···O and O—H···O hydrogen bonds (Table 1). The crystal structure is formed by weak inter­molecular N—H···O, O—H···O and C—H···O hydrogen bonds (Table 1 & Fig. 2) by linking the adjacent anions and cations by bridging water molecules through O—H···O hydrogen bonds into infinite two-dimensional network along [1 0 0] plane. The crystal structure is further stabilized by weak C—H···π (Table 1) and ππ [Cg1···Cg1i = 3.6507 (9); Cg2···Cg2ii = 3.6507 (9)Å; (i) -x,1-y,1-z; (ii) x,1/2-y,1/2+z; Cg1 and Cg2 are the centroids of the rings (C1—C6) and (N2/C12/C11/C10/C9/C13)] inter­actions.

For the biological activity of quinoline derivatives, see: Font et al. (1997); Sloboda et al. (1991). For similar structures, see: Castañeda et al. (2014); Kafka et al. (2012); Li & Chai (2007).

Synthesis and crystallization top

The title compound was synthesized by taking at 1:1 ratio of 8-hy­droxy­quinoline and of 3-nitro­phthalic acid was dissolved in a mixed solvent of methanol and water. The salt was formed while adding the base instanstaouly. The solution was stirred for about 2 h to get a homogenous solution. The solution was filtered off and kept aside for slow evaporation at room temperature which yields single crystals suitable for X-ray diffraction.

Refinement details top

C-bound H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms for O atoms were located from Fourier map and refined with O—H = 0.82 (1)Å and Uiso(H) = 1.5 Ueq(O). H atom for N atom was located from Fourier map and refined freely with N—H = 0.88 (1)Å.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down c axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
8-Hydroxyquinolinium 2-carboxy-6-nitrobenzoate monohydrate top
Crystal data top
C9H8NO+·C8H4NO6·H2OF(000) = 776
Mr = 374.30Dx = 1.581 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9900 reflections
a = 14.4283 (5) Åθ = 2.8–33.4°
b = 13.8196 (5) ŵ = 0.13 mm1
c = 8.0483 (3) ÅT = 295 K
β = 101.441 (2)°Block, colourless
V = 1572.89 (10) Å30.26 × 0.22 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7431 independent reflections
Radiation source: fine-focus sealed tube4272 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω and φ scansθmax = 36.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2323
Tmin = 0.968, Tmax = 0.977k = 1922
58922 measured reflectionsl = 1312
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0619P)2 + 0.9848P]
where P = (Fo2 + 2Fc2)/3
7431 reflections(Δ/σ)max < 0.001
260 parametersΔρmax = 0.50 e Å3
5 restraintsΔρmin = 0.38 e Å3
Crystal data top
C9H8NO+·C8H4NO6·H2OV = 1572.89 (10) Å3
Mr = 374.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.4283 (5) ŵ = 0.13 mm1
b = 13.8196 (5) ÅT = 295 K
c = 8.0483 (3) Å0.26 × 0.22 × 0.18 mm
β = 101.441 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7431 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4272 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.977Rint = 0.034
58922 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0605 restraints
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.50 e Å3
7431 reflectionsΔρmin = 0.38 e Å3
260 parameters
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.17265 (9)0.48978 (9)0.55989 (18)0.0237 (2)
C20.13410 (10)0.48988 (10)0.70682 (19)0.0262 (3)
C30.06506 (11)0.42272 (12)0.7270 (2)0.0331 (3)
H30.04030.42380.82520.040*
C40.03290 (11)0.35481 (12)0.6037 (2)0.0370 (4)
H40.01170.30910.62030.044*
C50.06716 (11)0.35508 (12)0.4557 (2)0.0339 (3)
H50.04490.31080.37020.041*
C60.13531 (10)0.42230 (10)0.43632 (19)0.0267 (3)
C70.24827 (10)0.56315 (10)0.53939 (18)0.0249 (3)
C80.16432 (11)0.56359 (11)0.84160 (19)0.0294 (3)
C90.46422 (11)0.34368 (10)0.87844 (19)0.0288 (3)
C100.53122 (13)0.40133 (12)0.8201 (2)0.0377 (4)
H100.52250.46800.81250.045*
C110.60883 (13)0.36137 (14)0.7744 (2)0.0424 (4)
H110.65210.40020.73410.051*
C120.62252 (11)0.26245 (14)0.7886 (2)0.0390 (4)
H120.67520.23460.75750.047*
C130.48139 (9)0.24333 (10)0.89029 (18)0.0247 (3)
C140.41699 (10)0.18003 (10)0.94525 (19)0.0284 (3)
C150.33963 (11)0.21885 (13)0.9934 (2)0.0364 (3)
H150.29780.17851.03460.044*
C160.32192 (13)0.31850 (15)0.9818 (2)0.0432 (4)
H160.26800.34281.01400.052*
C170.38181 (13)0.38061 (12)0.9246 (2)0.0390 (4)
H170.36850.44650.91600.047*
N10.16655 (10)0.42040 (10)0.27386 (18)0.0337 (3)
N20.56126 (9)0.20732 (9)0.84612 (17)0.0305 (3)
H20.5741 (15)0.1450 (8)0.866 (3)0.047 (6)*
O10.22455 (12)0.47889 (11)0.24810 (18)0.0545 (4)
O20.13344 (13)0.35960 (13)0.1701 (2)0.0684 (5)
O30.33312 (7)0.53639 (8)0.57868 (15)0.0318 (2)
O40.22067 (8)0.64521 (8)0.49029 (15)0.0326 (2)
O50.09894 (10)0.57856 (11)0.93152 (18)0.0465 (3)
H5A0.1152 (18)0.6216 (15)1.002 (3)0.070*
O60.23875 (9)0.60562 (10)0.86357 (17)0.0435 (3)
O70.43930 (9)0.08565 (8)0.94455 (17)0.0378 (3)
H70.3990 (13)0.0519 (15)0.981 (3)0.057*
O80.13275 (9)0.78915 (10)0.66412 (16)0.0392 (3)
H8A0.1644 (15)0.8061 (18)0.7569 (18)0.059*
H8B0.1616 (16)0.7423 (13)0.635 (3)0.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0214 (5)0.0215 (5)0.0289 (6)0.0023 (4)0.0070 (5)0.0021 (5)
C20.0244 (6)0.0266 (6)0.0286 (7)0.0001 (5)0.0074 (5)0.0023 (5)
C30.0308 (7)0.0365 (8)0.0344 (8)0.0042 (6)0.0123 (6)0.0047 (6)
C40.0300 (7)0.0364 (8)0.0457 (9)0.0096 (6)0.0101 (7)0.0028 (7)
C50.0298 (7)0.0321 (7)0.0395 (8)0.0067 (6)0.0064 (6)0.0041 (6)
C60.0244 (6)0.0262 (6)0.0304 (7)0.0012 (5)0.0076 (5)0.0007 (5)
C70.0269 (6)0.0238 (6)0.0262 (6)0.0013 (5)0.0109 (5)0.0016 (5)
C80.0323 (7)0.0301 (7)0.0269 (7)0.0003 (5)0.0084 (5)0.0024 (5)
C90.0337 (7)0.0212 (6)0.0294 (7)0.0003 (5)0.0014 (5)0.0015 (5)
C100.0465 (9)0.0239 (7)0.0395 (8)0.0065 (6)0.0006 (7)0.0066 (6)
C110.0365 (8)0.0441 (9)0.0449 (10)0.0124 (7)0.0041 (7)0.0152 (8)
C120.0267 (7)0.0467 (9)0.0441 (9)0.0008 (6)0.0088 (6)0.0120 (7)
C130.0249 (6)0.0221 (6)0.0264 (6)0.0004 (4)0.0034 (5)0.0023 (5)
C140.0289 (7)0.0256 (6)0.0303 (7)0.0042 (5)0.0052 (5)0.0017 (5)
C150.0316 (7)0.0420 (9)0.0371 (8)0.0043 (6)0.0103 (6)0.0004 (7)
C160.0377 (8)0.0510 (10)0.0427 (9)0.0119 (7)0.0126 (7)0.0041 (8)
C170.0446 (9)0.0305 (7)0.0415 (9)0.0111 (7)0.0072 (7)0.0023 (7)
N10.0339 (7)0.0353 (7)0.0334 (7)0.0031 (5)0.0103 (5)0.0067 (5)
N20.0281 (6)0.0267 (6)0.0368 (7)0.0031 (4)0.0069 (5)0.0071 (5)
O10.0734 (10)0.0545 (8)0.0431 (7)0.0271 (7)0.0301 (7)0.0107 (6)
O20.0782 (11)0.0794 (12)0.0555 (9)0.0402 (9)0.0328 (8)0.0384 (8)
O30.0249 (5)0.0287 (5)0.0439 (6)0.0004 (4)0.0122 (4)0.0032 (4)
O40.0375 (6)0.0241 (5)0.0365 (6)0.0007 (4)0.0084 (5)0.0031 (4)
O50.0434 (7)0.0575 (8)0.0442 (7)0.0089 (6)0.0222 (6)0.0169 (6)
O60.0428 (7)0.0496 (7)0.0410 (7)0.0147 (6)0.0153 (5)0.0122 (6)
O70.0393 (6)0.0232 (5)0.0537 (7)0.0050 (4)0.0161 (5)0.0044 (5)
O80.0429 (7)0.0397 (7)0.0361 (6)0.0043 (5)0.0104 (5)0.0014 (5)
Geometric parameters (Å, º) top
C1—C61.392 (2)C11—C121.383 (3)
C1—C21.4030 (19)C11—H110.9300
C1—C71.5222 (18)C12—N21.318 (2)
C2—C31.394 (2)C12—H120.9300
C2—C81.489 (2)C13—N21.3655 (18)
C3—C41.378 (2)C13—C141.4097 (19)
C3—H30.9300C14—O71.3437 (18)
C4—C51.377 (2)C14—C151.362 (2)
C4—H40.9300C15—C161.400 (3)
C5—C61.384 (2)C15—H150.9300
C5—H50.9300C16—C171.362 (3)
C6—N11.4654 (19)C16—H160.9300
C7—O41.2404 (17)C17—H170.9300
C7—O31.2577 (17)N1—O11.2106 (18)
C8—O61.2028 (19)N1—O21.2137 (19)
C8—O51.3142 (19)N2—H20.889 (9)
C9—C101.403 (2)O5—H5A0.823 (10)
C9—C131.4085 (19)O7—H70.841 (9)
C9—C171.410 (2)O8—H8A0.828 (10)
C10—C111.363 (3)O8—H8B0.829 (10)
C10—H100.9300
C6—C1—C2116.16 (12)C10—C11—C12119.32 (15)
C6—C1—C7123.58 (12)C10—C11—H11120.3
C2—C1—C7120.21 (12)C12—C11—H11120.3
C3—C2—C1120.61 (14)N2—C12—C11120.37 (16)
C3—C2—C8118.90 (13)N2—C12—H12119.8
C1—C2—C8120.46 (12)C11—C12—H12119.8
C4—C3—C2121.06 (14)N2—C13—C9119.16 (13)
C4—C3—H3119.5N2—C13—C14119.89 (13)
C2—C3—H3119.5C9—C13—C14120.94 (13)
C5—C4—C3119.59 (14)O7—C14—C15126.44 (14)
C5—C4—H4120.2O7—C14—C13115.32 (13)
C3—C4—H4120.2C15—C14—C13118.23 (14)
C4—C5—C6118.98 (15)C14—C15—C16121.17 (15)
C4—C5—H5120.5C14—C15—H15119.4
C6—C5—H5120.5C16—C15—H15119.4
C5—C6—C1123.52 (14)C17—C16—C15121.51 (16)
C5—C6—N1116.10 (13)C17—C16—H16119.2
C1—C6—N1120.38 (12)C15—C16—H16119.2
O4—C7—O3125.72 (13)C16—C17—C9119.08 (15)
O4—C7—C1116.86 (12)C16—C17—H17120.5
O3—C7—C1117.37 (12)C9—C17—H17120.5
O6—C8—O5124.10 (15)O1—N1—O2122.38 (15)
O6—C8—C2124.14 (14)O1—N1—C6119.10 (13)
O5—C8—C2111.75 (13)O2—N1—C6118.52 (14)
C10—C9—C13117.26 (14)C12—N2—C13122.68 (14)
C10—C9—C17123.74 (14)C12—N2—H2119.6 (14)
C13—C9—C17119.00 (14)C13—N2—H2117.5 (14)
C11—C10—C9121.17 (15)C8—O5—H5A110.8 (19)
C11—C10—H10119.4C14—O7—H7110.7 (17)
C9—C10—H10119.4H8A—O8—H8B105 (2)
C6—C1—C2—C32.4 (2)C9—C10—C11—C121.1 (3)
C7—C1—C2—C3179.76 (13)C10—C11—C12—N20.1 (3)
C6—C1—C2—C8175.78 (13)C10—C9—C13—N20.3 (2)
C7—C1—C2—C82.0 (2)C17—C9—C13—N2179.84 (14)
C1—C2—C3—C40.0 (2)C10—C9—C13—C14179.04 (14)
C8—C2—C3—C4178.20 (15)C17—C9—C13—C140.8 (2)
C2—C3—C4—C52.1 (3)N2—C13—C14—O72.0 (2)
C3—C4—C5—C61.7 (3)C9—C13—C14—O7177.38 (14)
C4—C5—C6—C10.8 (2)N2—C13—C14—C15177.96 (14)
C4—C5—C6—N1178.24 (15)C9—C13—C14—C152.7 (2)
C2—C1—C6—C52.9 (2)O7—C14—C15—C16177.32 (17)
C7—C1—C6—C5179.40 (14)C13—C14—C15—C162.8 (2)
C2—C1—C6—N1176.16 (13)C14—C15—C16—C171.0 (3)
C7—C1—C6—N11.6 (2)C15—C16—C17—C91.0 (3)
C6—C1—C7—O496.24 (16)C10—C9—C17—C16179.12 (17)
C2—C1—C7—O481.38 (17)C13—C9—C17—C161.0 (2)
C6—C1—C7—O385.96 (18)C5—C6—N1—O1178.42 (16)
C2—C1—C7—O396.42 (16)C1—C6—N1—O10.7 (2)
C3—C2—C8—O6157.79 (16)C5—C6—N1—O22.0 (2)
C1—C2—C8—O624.0 (2)C1—C6—N1—O2178.93 (17)
C3—C2—C8—O523.5 (2)C11—C12—N2—C131.5 (3)
C1—C2—C8—O5154.77 (14)C9—C13—N2—C121.6 (2)
C13—C9—C10—C111.0 (2)C14—C13—N2—C12177.75 (15)
C17—C9—C10—C11178.83 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.89 (1)2.00 (1)2.8112 (16)151 (2)
O5—H5A···O8ii0.82 (1)1.78 (1)2.5928 (18)171 (3)
O7—H7···O3iii0.84 (1)1.82 (1)2.6482 (15)168 (2)
O8—H8B···O40.83 (1)2.07 (1)2.8683 (17)163 (2)
O8—H8A···O4ii0.83 (1)2.01 (1)2.8288 (18)170 (2)
C11—H11···O1iv0.932.423.295 (2)156
C12—H12···O6i0.932.483.343 (2)155
C16—H16···O2v0.932.523.413 (2)160
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x, y+3/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x+1, y+1, z+1; (v) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.889 (9)2.002 (14)2.8112 (16)151 (2)
O5—H5A···O8ii0.823 (10)1.777 (11)2.5928 (18)171 (3)
O7—H7···O3iii0.841 (9)1.820 (11)2.6482 (15)168 (2)
O8—H8B···O40.829 (10)2.067 (12)2.8683 (17)163 (2)
O8—H8A···O4ii0.828 (10)2.009 (11)2.8288 (18)170 (2)
C11—H11···O1iv0.932.423.295 (2)156
C12—H12···O6i0.932.483.343 (2)155
C16—H16···O2v0.932.523.413 (2)160
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x, y+3/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x+1, y+1, z+1; (v) x, y, z+1.
 

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