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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o203.
Published online 2007 December 6. doi:  10.1107/S1600536807063982
PMCID: PMC2915265

4-Amino-2-methyl­quinolinium hydrogensulfate dihydrate

Abstract

In the title compound, C10H11N2 +·HSO4 ·2H2O, the asymmetric unit contains two protonated 4-amino­quinoline cations and two hydrogen sulfate anions with four water mol­ecules. The crystal structure involves extensive N—H(...)O and O—H(...)O hydrogen bonding.

Related literature

For related literature, see: Amini et al. (2007a [triangle],b [triangle]); Repicky et al. (2005 [triangle]).

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Object name is e-64-0o203-scheme1.jpg

Experimental

Crystal data

  • C10H11N2 +·HSO4 ·2H2O
  • M r = 292.32
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o203-efi1.jpg
  • a = 10.1585 (9) Å
  • b = 11.2131 (9) Å
  • c = 13.3545 (11) Å
  • α = 68.283 (6)°
  • β = 76.355 (7)°
  • γ = 67.949 (6)°
  • V = 1301.51 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 120 (2) K
  • 0.5 × 0.15 × 0.12 mm

Data collection

  • Stoe IPDSII diffractometer
  • Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 [triangle]) T min = 0.950, T max = 0.970
  • 16357 measured reflections
  • 7008 independent reflections
  • 5729 reflections with I > 2σ(I)
  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.182
  • S = 1.06
  • 7008 reflections
  • 409 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.99 e Å−3

Data collection: X-RED32 (Stoe & Cie, 2005 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063982/om2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063982/om2193Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge Shahid Beheshti University for financial support.

supplementary crystallographic information

Comment

In continuation of our research on the structure determination of simple ammonium salts (Amini et al., 2007a) as precursors for synthesis of double sulfate (Amini et al., 2007b), we have found that the this compound (Fig. 1) forms structures with extended hydrogen bonding in the presence of water molecules. From the packing diagram (Fig. 2), it seems that the intermolecular and intramolecular N—H···O and O—H···O and O—H···O hydrogen bonds (Table 1) are effective in the stabilization of the crystal structure. These compounds could be classified as an outstanding model system for polymers with higher dimensional hydrogen bonding. 4-aminoquinoline derivatives have cytotoxic activity (Repicky et al., 2005), so determination of molecular structure of these compounds could be beneficial. As it is shown in Fig. 2, the quinoline rings form π bonding stacks. The closest contact distance between adjacent aromatic rings is 3.328 (3) A°.

Experimental

2-methylquinolin-4-amine (1.58 g, 0.01 mol) was dissolved in 30 ml dichloromethane. Dropwise addition of concentrated sulfuric acid (0.98 g, 0.01 mol) resulted in a white precipitate which was filtered and dissolved in methanol. Needle shape crystals were grown by slow evaporation of a methanol solution at room temperature.

Refinement

The N-bond and O-bond H atoms were located in a difference map and their positions were freely refined. Other hydrogen atoms were refined using a riding model (C—H = 0.93–0.96 A°) with their displacement parameters set at 1.2 times Ueq of the parent atom.

Figures

Fig. 1.
Molecular structure. Displacement ellipsoids are drawn at the 30% probability level
Fig. 2.
Unit-cell packing diagram as viewed down the a-direction. Hydrogen bonds are shown as dashed lines.

Crystal data

C10H11N2+·HSO4·2H2OZ = 4
Mr = 292.32F000 = 616
Triclinic, P1Dx = 1.492 Mg m3
a = 10.1585 (9) ÅMo Kα radiation λ = 0.71073 Å
b = 11.2131 (9) ÅCell parameters from 2500 reflections
c = 13.3545 (11) Åθ = 1.7–29.2º
α = 68.283 (6)ºµ = 0.27 mm1
β = 76.355 (7)ºT = 120 (2) K
γ = 67.949 (6)ºNeedle, colorless
V = 1301.51 (19) Å30.5 × 0.15 × 0.12 mm

Data collection

Stoe IPDSII diffractometerRint = 0.087
ω scansθmax = 29.2º
Absorption correction: numerical(X-SHAPE; Stoe & Cie, 2005)θmin = 1.7º
Tmin = 0.950, Tmax = 0.970h = −13→13
16357 measured reflectionsk = −15→15
7008 independent reflectionsl = −18→16
5729 reflections with I > 2σ(I)

Refinement

Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.0853P)2 + 1.1102P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.060(Δ/σ)max = 0.019
wR(F2) = 0.182Δρmax = 0.39 e Å3
S = 1.06Δρmin = −0.99 e Å3
7008 reflectionsExtinction correction: none
409 parameters

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

xyzUiso*/Ueq
C1−0.2667 (2)0.3412 (2)0.37942 (17)0.0230 (4)
H1A−0.17890.35650.35830.028*
C2−0.2725 (2)0.2116 (2)0.42028 (19)0.0251 (4)
H2A−0.18820.13890.42680.03*
C3−0.4052 (2)0.1875 (2)0.45255 (19)0.0251 (4)
H3A−0.4080.09910.480.03*
C4−0.5305 (2)0.2943 (2)0.44357 (17)0.0228 (4)
H4A−0.61740.27720.46480.027*
C5−0.5292 (2)0.4296 (2)0.40258 (16)0.0206 (4)
C6−0.6557 (2)0.5461 (2)0.39237 (17)0.0208 (4)
C7−0.6404 (2)0.6757 (2)0.34890 (17)0.0228 (4)
H7−0.72150.75190.34110.027*
C8−0.5072 (2)0.6914 (2)0.31778 (17)0.0217 (4)
C9−0.4852 (3)0.8274 (2)0.27189 (19)0.0274 (5)
H9C−0.43420.83680.20050.033*
H9B−0.43110.83510.31790.033*
H9A−0.57640.89730.26790.033*
C10−0.3942 (2)0.4510 (2)0.36953 (17)0.0205 (4)
C11−0.7437 (2)0.6655 (2)0.12158 (18)0.0240 (4)
H11A−0.83390.65530.14150.029*
C12−0.7303 (2)0.7924 (2)0.08060 (19)0.0268 (4)
H12A−0.81160.86830.07360.032*
C13−0.5935 (2)0.8088 (2)0.04894 (19)0.0257 (4)
H13−0.58540.89530.02080.031*
C14−0.4726 (2)0.6974 (2)0.05956 (17)0.0230 (4)
H14−0.38320.70930.03860.028*
C15−0.4823 (2)0.5647 (2)0.10199 (16)0.0203 (4)
C16−0.3599 (2)0.4439 (2)0.11442 (17)0.0202 (4)
C17−0.3833 (2)0.3176 (2)0.15913 (17)0.0217 (4)
H17−0.30550.23850.16880.026*
C18−0.5200 (2)0.3094 (2)0.18876 (17)0.0216 (4)
C19−0.5493 (2)0.1767 (2)0.23516 (18)0.0253 (4)
H19A−0.46170.10440.2530.03*
H19B−0.58890.16410.18270.03*
H19C−0.61590.17670.29950.03*
C20−0.6205 (2)0.5506 (2)0.13349 (17)0.0207 (4)
N1−0.7861 (2)0.5326 (2)0.42328 (17)0.0264 (4)
H1B−0.799 (3)0.452 (3)0.450 (2)0.035 (8)*
H1C−0.863 (3)0.604 (3)0.421 (2)0.034 (8)*
N2−0.38895 (19)0.58169 (19)0.32826 (15)0.0215 (4)
H2B−0.297 (3)0.591 (3)0.304 (2)0.033 (8)*
N3−0.2264 (2)0.4497 (2)0.08604 (16)0.0241 (4)
H3B−0.206 (3)0.528 (3)0.056 (3)0.041 (9)*
H3C−0.156 (3)0.375 (3)0.090 (2)0.030 (7)*
N4−0.63363 (19)0.42260 (19)0.17560 (15)0.0217 (4)
H4B−0.724 (3)0.421 (3)0.197 (2)0.024 (7)*
O10.21598 (18)0.09186 (18)0.12957 (15)0.0304 (4)
H1D0.174 (4)0.085 (4)0.196 (3)0.049 (10)*
O20.19440 (18)0.16254 (17)−0.05753 (13)0.0285 (4)
O30.11031 (19)0.33038 (17)0.03498 (15)0.0316 (4)
O4−0.02002 (17)0.17733 (17)0.07138 (14)0.0279 (4)
O5−0.21953 (18)−0.06596 (18)0.35374 (15)0.0299 (4)
H5−0.169 (4)−0.059 (4)0.284 (3)0.054 (10)*
O6−0.20017 (18)−0.15065 (18)0.54201 (14)0.0307 (4)
O7−0.10350 (19)−0.30542 (17)0.43617 (14)0.0306 (4)
O80.01481 (18)−0.14707 (19)0.41604 (15)0.0328 (4)
O90.1039 (3)0.0757 (2)0.31884 (16)0.0445 (5)
H9D0.080 (4)0.007 (4)0.356 (3)0.056 (11)*
H9E0.133 (4)0.098 (4)0.358 (3)0.047 (10)*
O10−0.0982 (2)−0.0478 (2)0.16311 (16)0.0396 (5)
H10A−0.073 (4)0.026 (4)0.129 (3)0.050 (10)*
H10B−0.127 (4)−0.073 (3)0.124 (3)0.042 (9)*
O11−0.12512 (18)−0.36765 (18)0.25826 (15)0.0276 (4)
H11C−0.112 (3)−0.346 (3)0.309 (3)0.038 (8)*
H11B−0.137 (4)−0.303 (4)0.203 (3)0.070 (13)*
O12−0.90519 (19)0.4039 (2)0.21908 (16)0.0316 (4)
H12B−0.916 (4)0.386 (4)0.165 (3)0.058 (11)*
H12C−0.979 (4)0.478 (4)0.231 (3)0.063 (11)*
S10.12067 (5)0.19469 (5)0.04176 (4)0.02081 (14)
S2−0.12161 (5)−0.17207 (5)0.44180 (4)0.02107 (14)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0200 (10)0.0298 (11)0.0256 (10)−0.0120 (8)−0.0022 (8)−0.0116 (8)
C20.0199 (10)0.0276 (11)0.0317 (11)−0.0074 (8)−0.0033 (8)−0.0137 (9)
C30.0260 (11)0.0250 (10)0.0304 (11)−0.0135 (9)−0.0012 (8)−0.0111 (8)
C40.0205 (10)0.0282 (11)0.0258 (10)−0.0132 (8)−0.0009 (8)−0.0108 (8)
C50.0196 (9)0.0262 (10)0.0220 (9)−0.0122 (8)−0.0019 (7)−0.0095 (8)
C60.0168 (9)0.0281 (10)0.0224 (9)−0.0096 (8)−0.0002 (7)−0.0118 (8)
C70.0223 (10)0.0237 (10)0.0258 (10)−0.0077 (8)−0.0040 (8)−0.0102 (8)
C80.0222 (10)0.0240 (10)0.0228 (9)−0.0099 (8)−0.0033 (7)−0.0086 (8)
C90.0317 (12)0.0254 (11)0.0297 (11)−0.0148 (9)−0.0041 (9)−0.0076 (8)
C100.0197 (9)0.0247 (10)0.0230 (9)−0.0109 (8)−0.0022 (7)−0.0102 (8)
C110.0184 (9)0.0310 (11)0.0278 (10)−0.0109 (8)−0.0033 (8)−0.0113 (8)
C120.0213 (10)0.0281 (11)0.0329 (11)−0.0059 (8)−0.0057 (8)−0.0121 (9)
C130.0266 (11)0.0245 (10)0.0307 (11)−0.0120 (9)−0.0034 (9)−0.0098 (8)
C140.0213 (10)0.0275 (10)0.0253 (10)−0.0126 (8)−0.0030 (8)−0.0086 (8)
C150.0192 (9)0.0264 (10)0.0212 (9)−0.0112 (8)−0.0019 (7)−0.0101 (8)
C160.0178 (9)0.0268 (10)0.0225 (9)−0.0113 (8)−0.0015 (7)−0.0109 (8)
C170.0176 (9)0.0252 (10)0.0278 (10)−0.0091 (8)−0.0035 (8)−0.0115 (8)
C180.0201 (9)0.0260 (10)0.0242 (10)−0.0121 (8)−0.0025 (7)−0.0091 (8)
C190.0258 (10)0.0272 (11)0.0288 (11)−0.0154 (9)−0.0009 (8)−0.0097 (8)
C200.0192 (9)0.0251 (10)0.0228 (9)−0.0102 (8)−0.0035 (7)−0.0092 (8)
N10.0177 (9)0.0285 (10)0.0355 (10)−0.0099 (8)−0.0012 (7)−0.0112 (8)
N20.0199 (8)0.0259 (9)0.0248 (8)−0.0121 (7)−0.0015 (7)−0.0106 (7)
N30.0160 (9)0.0269 (10)0.0325 (10)−0.0104 (8)−0.0011 (7)−0.0101 (8)
N40.0171 (8)0.0292 (9)0.0255 (9)−0.0130 (7)−0.0011 (6)−0.0109 (7)
O10.0226 (8)0.0384 (10)0.0315 (9)−0.0084 (7)−0.0048 (7)−0.0127 (7)
O20.0302 (8)0.0337 (9)0.0284 (8)−0.0149 (7)0.0030 (6)−0.0162 (7)
O30.0305 (9)0.0282 (8)0.0435 (10)−0.0172 (7)0.0046 (7)−0.0167 (7)
O40.0183 (7)0.0330 (9)0.0387 (9)−0.0157 (7)−0.0021 (6)−0.0111 (7)
O50.0238 (8)0.0329 (9)0.0346 (9)−0.0071 (7)−0.0045 (7)−0.0135 (7)
O60.0300 (9)0.0380 (9)0.0305 (8)−0.0175 (7)0.0027 (7)−0.0148 (7)
O70.0325 (9)0.0268 (8)0.0367 (9)−0.0127 (7)−0.0027 (7)−0.0121 (7)
O80.0206 (8)0.0443 (10)0.0398 (10)−0.0194 (7)−0.0011 (7)−0.0124 (8)
O90.0656 (14)0.0587 (13)0.0308 (10)−0.0463 (12)0.0001 (9)−0.0143 (9)
O100.0614 (13)0.0439 (11)0.0288 (9)−0.0365 (10)−0.0023 (8)−0.0099 (8)
O110.0253 (8)0.0320 (9)0.0328 (9)−0.0150 (7)−0.0018 (7)−0.0130 (7)
O120.0208 (8)0.0380 (10)0.0445 (10)−0.0133 (7)−0.0023 (7)−0.0191 (8)
S10.0171 (3)0.0242 (3)0.0272 (3)−0.0123 (2)−0.00033 (19)−0.0103 (2)
S20.0170 (3)0.0253 (3)0.0263 (3)−0.0114 (2)−0.00057 (19)−0.0105 (2)

Geometric parameters (Å, °)

C1—C21.369 (3)C16—C171.407 (3)
C1—C101.405 (3)C17—C181.380 (3)
C1—H1A0.93C17—H170.93
C2—C31.411 (3)C18—N41.344 (3)
C2—H2A0.93C18—C191.499 (3)
C3—C41.374 (3)C19—H19A0.96
C3—H3A0.93C19—H19B0.96
C4—C51.414 (3)C19—H19C0.96
C4—H4A0.93C20—N41.380 (3)
C5—C101.420 (3)N1—H1B0.89 (3)
C5—C61.437 (3)N1—H1C0.89 (3)
C6—N11.339 (3)N2—H2B0.95 (3)
C6—C71.406 (3)N3—H3B0.90 (3)
C7—C81.376 (3)N3—H3C0.86 (3)
C7—H70.93N4—H4B0.90 (3)
C8—N21.348 (3)O1—S11.5293 (18)
C8—C91.500 (3)O1—H1D0.87 (4)
C9—H9C0.96O2—S11.4601 (17)
C9—H9B0.96O3—S11.4548 (16)
C9—H9A0.96O4—S11.4568 (15)
C10—N21.379 (3)O5—S21.5543 (18)
C11—C121.370 (3)O5—H50.94 (4)
C11—C201.408 (3)O6—S21.4406 (17)
C11—H11A0.93O7—S21.4646 (17)
C12—C131.414 (3)O8—S21.4536 (15)
C12—H12A0.93O9—H9D0.84 (4)
C13—C141.374 (3)O9—H9E0.81 (4)
C13—H130.93O10—H10A0.88 (4)
C14—C151.415 (3)O10—H10B0.82 (3)
C14—H140.93O11—H11C0.85 (3)
C15—C201.419 (3)O11—H11B0.82 (4)
C15—C161.440 (3)O12—H12B0.86 (4)
C16—N31.339 (2)O12—H12C0.92 (4)
C2—C1—C10119.60 (19)N3—C16—C17120.0 (2)
C2—C1—H1A120.2N3—C16—C15121.66 (19)
C10—C1—H1A120.2C17—C16—C15118.32 (18)
C1—C2—C3120.6 (2)C18—C17—C16121.0 (2)
C1—C2—H2A119.7C18—C17—H17119.5
C3—C2—H2A119.7C16—C17—H17119.5
C4—C3—C2120.19 (19)N4—C18—C17120.30 (19)
C4—C3—H3A119.9N4—C18—C19117.20 (18)
C2—C3—H3A119.9C17—C18—C19122.5 (2)
C3—C4—C5121.01 (19)C18—C19—H19A109.5
C3—C4—H4A119.5C18—C19—H19B109.5
C5—C4—H4A119.5H19A—C19—H19B109.5
C4—C5—C10117.63 (19)C18—C19—H19C109.5
C4—C5—C6124.08 (18)H19A—C19—H19C109.5
C10—C5—C6118.30 (18)H19B—C19—H19C109.5
N1—C6—C7120.1 (2)N4—C20—C11119.97 (18)
N1—C6—C5121.16 (19)N4—C20—C15119.33 (19)
C7—C6—C5118.71 (18)C11—C20—C15120.70 (19)
C8—C7—C6120.9 (2)C6—N1—H1B122 (2)
C8—C7—H7119.6C6—N1—H1C120.9 (19)
C6—C7—H7119.6H1B—N1—H1C117 (3)
N2—C8—C7120.14 (19)C8—N2—C10122.78 (17)
N2—C8—C9116.95 (18)C8—N2—H2B121.3 (18)
C7—C8—C9122.9 (2)C10—N2—H2B115.9 (18)
C8—C9—H9C109.5C16—N3—H3B123 (2)
C8—C9—H9B109.5C16—N3—H3C118.9 (19)
H9C—C9—H9B109.5H3B—N3—H3C118 (3)
C8—C9—H9A109.5C18—N4—C20122.61 (17)
H9C—C9—H9A109.5C18—N4—H4B122.8 (17)
H9B—C9—H9A109.5C20—N4—H4B114.6 (17)
N2—C10—C1119.84 (18)S1—O1—H1D114 (2)
N2—C10—C5119.20 (19)S2—O5—H5111 (2)
C1—C10—C5120.96 (19)H9D—O9—H9E109 (4)
C12—C11—C20119.83 (19)H10A—O10—H10B114 (3)
C12—C11—H11A120.1H11C—O11—H11B111 (3)
C20—C11—H11A120.1H12B—O12—H12C111 (3)
C11—C12—C13120.4 (2)O3—S1—O4110.45 (10)
C11—C12—H12A119.8O3—S1—O2111.62 (10)
C13—C12—H12A119.8O4—S1—O2112.86 (10)
C14—C13—C12120.2 (2)O3—S1—O1108.74 (10)
C14—C13—H13119.9O4—S1—O1108.47 (10)
C12—C13—H13119.9O2—S1—O1104.41 (10)
C13—C14—C15120.93 (19)O6—S2—O8113.87 (10)
C13—C14—H14119.5O6—S2—O7112.78 (10)
C15—C14—H14119.5O8—S2—O7110.74 (11)
C14—C15—C20117.89 (19)O6—S2—O5104.17 (10)
C14—C15—C16123.65 (18)O8—S2—O5108.13 (10)
C20—C15—C16118.47 (18)O7—S2—O5106.56 (10)
C10—C1—C2—C30.0 (3)C13—C14—C15—C16179.5 (2)
C1—C2—C3—C4−0.2 (3)C14—C15—C16—N30.0 (3)
C2—C3—C4—C5−0.3 (3)C20—C15—C16—N3179.79 (19)
C3—C4—C5—C101.0 (3)C14—C15—C16—C17179.10 (19)
C3—C4—C5—C6−179.1 (2)C20—C15—C16—C17−1.2 (3)
C4—C5—C6—N10.8 (3)N3—C16—C17—C18−179.9 (2)
C10—C5—C6—N1−179.22 (19)C15—C16—C17—C181.0 (3)
C4—C5—C6—C7−179.12 (19)C16—C17—C18—N4−0.2 (3)
C10—C5—C6—C70.8 (3)C16—C17—C18—C19179.12 (19)
N1—C6—C7—C8179.3 (2)C12—C11—C20—N4179.5 (2)
C5—C6—C7—C8−0.7 (3)C12—C11—C20—C15−0.9 (3)
C6—C7—C8—N20.3 (3)C14—C15—C20—N4−179.74 (18)
C6—C7—C8—C9−179.5 (2)C16—C15—C20—N40.5 (3)
C2—C1—C10—N2−179.89 (19)C14—C15—C20—C110.7 (3)
C2—C1—C10—C50.8 (3)C16—C15—C20—C11−179.10 (19)
C4—C5—C10—N2179.44 (18)C7—C8—N2—C100.1 (3)
C6—C5—C10—N2−0.5 (3)C9—C8—N2—C10179.83 (18)
C4—C5—C10—C1−1.3 (3)C1—C10—N2—C8−179.24 (19)
C6—C5—C10—C1178.79 (19)C5—C10—N2—C80.1 (3)
C20—C11—C12—C130.8 (3)C17—C18—N4—C20−0.5 (3)
C11—C12—C13—C14−0.4 (3)C19—C18—N4—C20−179.86 (18)
C12—C13—C14—C150.1 (3)C11—C20—N4—C18179.95 (19)
C13—C14—C15—C20−0.2 (3)C15—C20—N4—C180.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O7i0.89 (3)2.16 (3)2.981 (3)154 (3)
N1—H1C···O7ii0.88 (3)2.26 (3)3.049 (3)149 (3)
N1—H1C···O8ii0.88 (3)2.58 (3)3.374 (3)151 (3)
O1—H1D···O90.88 (4)1.61 (4)2.485 (3)177 (5)
N2—H2B···O11iii0.95 (3)1.88 (3)2.819 (3)172 (3)
N3—H3B···O3iv0.90 (3)2.03 (3)2.902 (3)163 (3)
N3—H3C···O30.87 (3)2.54 (3)3.177 (3)132 (3)
N3—H3C···O40.87 (3)2.20 (3)3.034 (3)162 (3)
N4—H4B···O120.90 (3)1.87 (3)2.753 (3)169 (3)
O5—H5···O100.94 (4)1.58 (4)2.523 (3)174 (5)
O9—H9D···O80.84 (4)1.91 (4)2.736 (3)169 (4)
O9—H9E···O6v0.81 (4)1.98 (4)2.783 (3)178 (5)
O10—H10A···O40.89 (4)1.81 (4)2.695 (3)175 (3)
O10—H10B···O2vi0.83 (4)1.93 (4)2.745 (3)169 (4)
O11—H11B···O2vi0.82 (4)2.04 (4)2.843 (3)167 (5)
O11—H11C···O70.85 (4)1.94 (4)2.787 (3)172 (3)
O12—H12B···O3vii0.86 (4)1.98 (4)2.823 (3)166 (4)
O12—H12C···O11ii0.92 (4)1.90 (4)2.823 (3)177 (4)

Symmetry codes: (i) −x−1, −y, −z+1; (ii) x−1, y+1, z; (iii) x, y+1, z; (iv) −x, −y+1, −z; (v) −x, −y, −z+1; (vi) −x, −y, −z; (vii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2193).

References

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