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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o806–o807.
Published online 2010 March 13. doi:  10.1107/S1600536810008779
PMCID: PMC2984073

5,6,7,8-Tetra­hydro­quinoline 1-oxide hemihydrate

Abstract

In the title compound, C9H11NO·0.5H2O, the asymmetric unit contains two similar mol­ecules of 5,6,7,8-tetra­hydro­quinoline 1-oxide and one water mol­ecule. The water mol­ecule links the two O atoms of both independent N-oxides into dimers via O—H(...)O hydrogen bonds, forming a three-dimensional network along [101], which is additionally stabilized by weak C—H(...)O inter­molecular inter­actions. In each mol­ecule, the saturated six-membered rings exist in a conformation inter­mediate between a half-chair and sofa.

Related literature

For background to the chemistry of the title compound and its applications, see: Coperet et al. (1998 [triangle]); Li (2005 [triangle]); Kaiser et al. (2006 [triangle]); Kaczorowski et al. (2009 [triangle]). For the synthesis, see: Jacobs et al. (2000 [triangle]); Barbay et al. (2008 [triangle]). For the biological activity of 5,6,7,8-tetra­hydro­quinoline derivatives, see: Calhoun et al. (1995 [triangle]); Abd El-Salam et al. (2009 [triangle]). For a related structure, see: HXTHQO (CSD, November 2009 release). For structure inter­pretation tools, see: Duax & Norton (1975 [triangle]); Allen et al. (1987 [triangle]); Allen (2002 [triangle]); Bruno et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o806-scheme1.jpg

Experimental

Crystal data

  • C9H11NO·0.5H2O
  • M r = 158.20
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o806-efi1.jpg
  • a = 14.725 (4) Å
  • b = 14.464 (4) Å
  • c = 15.474 (3) Å
  • V = 3295.7 (14) Å3
  • Z = 16
  • Cu Kα radiation
  • μ = 0.70 mm−1
  • T = 293 K
  • 0.28 × 0.26 × 0.21 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.832, T max = 0.873
  • 11258 measured reflections
  • 2727 independent reflections
  • 1989 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.205
  • S = 1.39
  • 2727 reflections
  • 215 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008779/jj2025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008779/jj2025Isup2.hkl

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

supplementary crystallographic information

Comment

5,6,7,8-Tetrahydroquinoline 1-oxide, (I), is an important intermediate for the synthesis of quinoline derivatives via Boekelheide rearrangement (Li, 2002; Kaiser et al., 2006; Coperet et al., 1998). The 5,6,7,8-tetrahydroquinoline moiety is found as a subunit in numerous medicinally interesting compounds (Calhoun et al., 1995; Abd El-Salam et al., 2009). Compound (I) can be obtained by the reaction of 5,6,7,8-tetrahydroquinoline with hydrogen peroxide or with MCPBA (Jacobs et al., 2000; Barbay et al., 2008). A search of the Cambridge Structural Database (November 2009 Release; Allen, 2002; Bruno et al., 2002) showed 26 organic compounds with the 5,6,7,8-tetrahydroquinoline moiety. Due to our interest in the preparartion of new nanomaterials based on organometallic complexes similar to those obtained from Cinchona alkaloids (Kaczorowski et al., 2009), a new method of synthesis for (I), by the oxidation of 5,6,7,8-tetrahydroquinoline with the catalytic system of oxone/TlOAc/PhI in a water-acetonitrile solution at room temperature has been developed and its crystal and molecular structure reported.

The asymmetric unit contains two similar molecules of 5,6,7,8-tetrahydroquinoline 1-oxide and one water molecule (Fig. 1). The water molecule links the two O atoms of both independent N-oxides by O—H···O hydrogen bonds into dimmers, which form a three-dimensional network along the [101] (Fig. 2). Additional weak C—H···O intermolecular interactions help stabilize the crystal packing (Table 1). The water molecule is observed in the 1H NMR spectrum as a broad signal at 2.4 ppm and in the IR spectrum as two absorption maxima for two different O—H bonds at 3368 and 3312 cm-1, respectively. The bond distances and angles in (I) are in normal ranges (Allen et al., 1987) and are comparable to the corresponding values observed in related structure of 5-hydroxy-5,6,7,8-tetrahydroquinoline 1-oxide (HXTHQO; CSD, November 2009 Release). In (I) the 6-membered fused-ring systems of the molecules A and B, are observed in an intermediate conformation between a half-chair and sofa with asymmetry parameters ΔCs(C6A) = 13.4 (3)°, ΔC2(C6A,C7A) = 11.2 (4)°, ΔCs(C6B) = 11.1 (2)° and ΔC2(C6B, C7B) =14.8 (3)° (Duax & Norton, 1975).

Experimental

The title compound, C9H11NO.0.5H2O, was synthesized by the oxidation process of the 5,6,7,8-tetrahydroquinoline with an oxone/TlOAc/PhI in water-acetonitrile solution, catalytic system at room temperature. To a solution of 5,6,7,8-tetrahydroquinoline (333 mg, 0.325 ml, 2.5 mmol,), in acetonitrile (7.5 ml) and water (7.5 ml), PhI (1.25 ml of a 0.1M solution in MeCN, 0.124 mmol) and thallous acetate (50 µl of 0.16M solution in water, 0.008 mmol) were added. Next, oxone (6.98 g, 11.5 mmol) was added in five portions over 6 h under stirring at room temperature. Substrate disappearing and new product forming was observed by TLC (Rf = 0.75 and Rf = 015, respectively, in ethyl acetate/methanol 50:1). The next day (after 20 h), 10% sodium hydroxide (10 ml), dichloromethane (30 ml) and water (30 ml) were added and the mixture was stirred for 5 min. The organic solution was separated and the aqueous phase was extracted with CH2Cl2 (2 x 15 ml). The combined organic phase was dried (anhydrous Na2SO4) and concentrated. Pure products 350 mg (95.0%) were obtained in oily form. After purification on column chromatography with silica gel and using ethyl acetate, the trace of the substrate was first removed. The product was eluted with a mixture of ethyl acetate/methanol (50:1) and colourless crystals were obtained. Yield: 310 mg (83%) and m.p. 344 K. Crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a dichloromethane/hexane (1:10) solution.

Refinement

The H atoms of the water molecule involved in the intramolecular hydrogen bonds were located by difference Fourier synthesis and refined freely [O—H = 0.96 (3) and 0.95 (4) Å]. The remaining H atoms were positioned geometrically and treated as riding on their C atoms, with C—H distances of 0.93 Å (aromatic) and 0.97 Å (CH2). All H atoms were refined with Uiso(H) = 1.5Ueq(O, C)].

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. Dashed lines indicate O—H ··· O hydrogen bonds.
Fig. 2.
A view of the molecular packing in (I) (black - molecules A, red - molecules B, green - H2O). Dashed lines indicate O—H ··· O hydrogen bonds and weak C—H···O intermolecular interactions.

Crystal data

C9H11NO·0.5H2OF(000) = 1360
Mr = 158.20Dx = 1.275 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 3676 reflections
a = 14.725 (4) Åθ = 5.7–66.9°
b = 14.464 (4) ŵ = 0.70 mm1
c = 15.474 (3) ÅT = 293 K
V = 3295.7 (14) Å3Block, colourless
Z = 160.28 × 0.26 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer2727 independent reflections
Radiation source: fine-focus sealed tube1989 reflections with I > 2σ(I)
graphiteRint = 0.053
[var phi] and ω scansθmax = 65.4°, θmin = 5.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −17→16
Tmin = 0.832, Tmax = 0.873k = −16→17
11258 measured reflectionsl = −18→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.205w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.39(Δ/σ)max < 0.001
2727 reflectionsΔρmax = 0.44 e Å3
215 parametersΔρmin = −0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0014 (4)

Special details

Experimental. 1H MNR (400 MHz, CDCl3) δ: 8.13 (d, 1H, J = 6.0 Hz), 7.04–6.99 (m, 2H), 2.93 (t, 2H, J = 6.4 Hz), 2.75 (t, 2H, J = 6.4 Hz), 2.40 (br s, 1H), 1.92–1.85 (m, 2H), 1,78–1.72 (m, 2H); 13C MNR (100 MHz, CDCl3) δ: 148.8, 136.9, 136.4, 126.6, 121.9, 28.6, 24.6, 21.8, 21.6; IR (KBr, ν, cm-1): 3368 (s, OH), 3312 (s, OH), 3076 (m), 3050 (m), 3009 (m), 2935 (s), 2871 (m), 2837 (m), 2498 (w), 2410 (w), 2151 (w), 1970 (w), 1686 (m, NO), 1596 (m), 1482 (m), 1449 (s), 1334 (m), 1253 (s), 1232 (s), 1211 (s), 1194 (s), 1155 (m), 1089 (m), 1074 (s), 1041 (m), 971 (s), 897 (m), 865 (w), 830 (m), 797 (s), 701 (m), 676 (m).
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 > σ(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)

xyzUiso*/Ueq
O1A0.11925 (15)0.33158 (10)0.13008 (9)0.0703 (6)
N1A0.13994 (15)0.41708 (12)0.11018 (11)0.0502 (6)
C2A0.16947 (18)0.47498 (16)0.17206 (15)0.0581 (7)
H2A0.17370.45470.22900.087*
C3A0.1930 (2)0.56261 (17)0.15166 (17)0.0666 (8)
H3A0.21430.60250.19420.100*
C4A0.1853 (2)0.59244 (16)0.06758 (18)0.0669 (8)
H4A0.20180.65270.05360.100*
C5A0.1449 (2)0.56465 (16)−0.08980 (17)0.0686 (8)
H51A0.09000.6010−0.09640.103*
H52A0.19610.6041−0.10410.103*
C6A0.1422 (2)0.4849 (2)−0.15194 (16)0.0774 (9)
H61A0.12680.5075−0.20910.116*
H62A0.20180.4566−0.15510.116*
C7A0.0749 (2)0.41457 (18)−0.12508 (14)0.0673 (8)
H71A0.07410.3649−0.16720.101*
H72A0.01490.4424−0.12420.101*
C8A0.09560 (19)0.37485 (14)−0.03650 (13)0.0534 (7)
H81A0.04080.3472−0.01320.080*
H82A0.14050.3262−0.04260.080*
C9A0.13012 (16)0.44502 (14)0.02589 (12)0.0455 (6)
C10A0.15331 (17)0.53397 (15)0.00343 (15)0.0520 (6)
O1B0.13846 (14)0.36329 (13)0.38241 (10)0.0701 (6)
N1B0.05059 (15)0.35441 (11)0.39183 (10)0.0489 (6)
C2B−0.0012 (2)0.33685 (15)0.32153 (14)0.0571 (7)
H2B0.02580.33140.26740.086*
C3B−0.0921 (2)0.32725 (16)0.32982 (17)0.0647 (8)
H3B−0.12770.31480.28150.097*
C4B−0.1320 (2)0.33585 (16)0.40978 (19)0.0658 (7)
H4B−0.19460.32970.41530.099*
C5B−0.1198 (3)0.3615 (2)0.57197 (19)0.0843 (11)
H51B−0.16950.31790.57760.126*
H52B−0.14410.42320.58000.126*
C6B−0.0486 (3)0.3418 (2)0.64194 (17)0.0941 (12)
H61B−0.07470.35380.69840.141*
H62B−0.03150.27710.63970.141*
C7B0.0323 (3)0.3992 (2)0.63022 (15)0.0853 (11)
H71B0.07470.38700.67680.128*
H72B0.01510.46380.63310.128*
C8B0.0784 (2)0.38036 (16)0.54433 (14)0.0591 (7)
H81B0.11620.43290.52950.089*
H82B0.11770.32700.55050.089*
C9B0.01368 (19)0.36319 (13)0.47254 (13)0.0475 (6)
C10B−0.0792 (2)0.35369 (15)0.48235 (15)0.0569 (7)
O20.21964 (17)0.24427 (13)0.26255 (13)0.0781 (7)
H210.188 (2)0.269 (2)0.213 (2)0.117*
H220.195 (2)0.280 (2)0.308 (2)0.117*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.1126 (19)0.0511 (9)0.0473 (9)−0.0176 (9)−0.0026 (9)0.0080 (7)
N1A0.0606 (16)0.0485 (10)0.0415 (9)−0.0037 (8)0.0024 (8)−0.0043 (8)
C2A0.0615 (18)0.0618 (14)0.0510 (11)−0.0026 (12)−0.0041 (11)−0.0143 (11)
C3A0.067 (2)0.0616 (14)0.0708 (15)−0.0049 (12)−0.0088 (14)−0.0202 (12)
C4A0.070 (2)0.0476 (12)0.0833 (17)−0.0082 (12)0.0021 (15)−0.0046 (12)
C5A0.079 (2)0.0593 (14)0.0676 (14)−0.0017 (13)0.0070 (14)0.0177 (12)
C6A0.099 (3)0.0823 (18)0.0509 (12)0.0069 (16)0.0040 (14)0.0130 (13)
C7A0.086 (3)0.0698 (16)0.0463 (12)0.0007 (14)−0.0053 (12)−0.0003 (11)
C8A0.069 (2)0.0491 (12)0.0426 (11)−0.0037 (10)0.0005 (11)−0.0051 (9)
C9A0.0486 (16)0.0471 (11)0.0408 (10)0.0002 (9)0.0054 (10)−0.0019 (9)
C10A0.0497 (17)0.0473 (12)0.0590 (12)−0.0006 (9)0.0060 (11)0.0004 (11)
O1B0.0602 (16)0.0916 (13)0.0584 (10)−0.0088 (10)0.0101 (9)−0.0125 (9)
N1B0.0553 (16)0.0495 (10)0.0418 (9)−0.0027 (8)0.0034 (9)−0.0025 (8)
C2B0.071 (2)0.0567 (13)0.0439 (11)−0.0008 (12)−0.0046 (12)−0.0036 (10)
C3B0.074 (2)0.0562 (14)0.0638 (15)−0.0020 (12)−0.0162 (14)0.0025 (11)
C4B0.0531 (19)0.0587 (14)0.0855 (18)0.0083 (12)0.0009 (15)0.0121 (13)
C5B0.089 (3)0.0870 (19)0.0769 (18)0.0294 (17)0.0379 (18)0.0192 (15)
C6B0.142 (4)0.086 (2)0.0537 (15)0.026 (2)0.0270 (18)0.0116 (14)
C7B0.136 (4)0.0739 (17)0.0454 (13)0.0120 (19)0.0020 (16)−0.0034 (13)
C8B0.081 (2)0.0520 (12)0.0446 (11)0.0045 (11)−0.0058 (12)−0.0046 (10)
C9B0.0632 (19)0.0377 (10)0.0416 (11)0.0064 (9)0.0042 (10)0.0016 (8)
C10B0.065 (2)0.0469 (12)0.0583 (13)0.0125 (11)0.0090 (12)0.0092 (10)
O20.0836 (19)0.0752 (12)0.0755 (11)0.0184 (10)0.0147 (11)0.0021 (9)

Geometric parameters (Å, °)

O1A—N1A1.310 (2)N1B—C2B1.353 (3)
N1A—C2A1.344 (3)N1B—C9B1.368 (3)
N1A—C9A1.373 (3)C2B—C3B1.352 (4)
C2A—C3A1.351 (3)C2B—H2B0.9300
C2A—H2A0.9300C3B—C4B1.375 (4)
C3A—C4A1.375 (4)C3B—H3B0.9300
C3A—H3A0.9300C4B—C10B1.390 (4)
C4A—C10A1.387 (4)C4B—H4B0.9300
C4A—H4A0.9300C5B—C10B1.514 (4)
C5A—C6A1.503 (4)C5B—C6B1.534 (5)
C5A—C10A1.514 (3)C5B—H51B0.9700
C5A—H51A0.9700C5B—H52B0.9700
C5A—H52A0.9700C6B—C7B1.462 (5)
C6A—C7A1.480 (4)C6B—H61B0.9700
C6A—H61A0.9700C6B—H62B0.9700
C6A—H62A0.9700C7B—C8B1.517 (4)
C7A—C8A1.517 (3)C7B—H71B0.9700
C7A—H71A0.9700C7B—H72B0.9700
C7A—H72A0.9700C8B—C9B1.484 (3)
C8A—C9A1.490 (3)C8B—H81B0.9700
C8A—H81A0.9700C8B—H82B0.9700
C8A—H82A0.9700C9B—C10B1.383 (4)
C9A—C10A1.376 (3)O2—H210.96 (3)
O1B—N1B1.308 (3)O2—H220.95 (4)
O1A—N1A—C2A119.72 (18)O1B—N1B—C9B119.0 (2)
O1A—N1A—C9A118.46 (17)C2B—N1B—C9B121.9 (2)
C2A—N1A—C9A121.83 (19)N1B—C2B—C3B120.1 (2)
N1A—C2A—C3A120.0 (2)N1B—C2B—H2B120.0
N1A—C2A—H2A120.0C3B—C2B—H2B120.0
C3A—C2A—H2A120.0C2B—C3B—C4B119.9 (3)
C2A—C3A—C4A119.6 (2)C2B—C3B—H3B120.0
C2A—C3A—H3A120.2C4B—C3B—H3B120.0
C4A—C3A—H3A120.2C3B—C4B—C10B120.3 (3)
C3A—C4A—C10A120.9 (2)C3B—C4B—H4B119.8
C3A—C4A—H4A119.5C10B—C4B—H4B119.8
C10A—C4A—H4A119.5C10B—C5B—C6B111.2 (3)
C6A—C5A—C10A112.75 (19)C10B—C5B—H51B109.4
C6A—C5A—H51A109.0C6B—C5B—H51B109.4
C10A—C5A—H51A109.0C10B—C5B—H52B109.4
C6A—C5A—H52A109.0C6B—C5B—H52B109.4
C10A—C5A—H52A109.0H51B—C5B—H52B108.0
H51A—C5A—H52A107.8C7B—C6B—C5B111.3 (3)
C7A—C6A—C5A111.5 (2)C7B—C6B—H61B109.4
C7A—C6A—H61A109.3C5B—C6B—H61B109.4
C5A—C6A—H61A109.3C7B—C6B—H62B109.4
C7A—C6A—H62A109.3C5B—C6B—H62B109.4
C5A—C6A—H62A109.3H61B—C6B—H62B108.0
H61A—C6A—H62A108.0C6B—C7B—C8B111.8 (2)
C6A—C7A—C8A112.3 (2)C6B—C7B—H71B109.3
C6A—C7A—H71A109.1C8B—C7B—H71B109.3
C8A—C7A—H71A109.1C6B—C7B—H72B109.3
C6A—C7A—H72A109.1C8B—C7B—H72B109.3
C8A—C7A—H72A109.1H71B—C7B—H72B107.9
H71A—C7A—H72A107.9C9B—C8B—C7B113.5 (3)
C9A—C8A—C7A113.33 (19)C9B—C8B—H81B108.9
C9A—C8A—H81A108.9C7B—C8B—H81B108.9
C7A—C8A—H81A108.9C9B—C8B—H82B108.9
C9A—C8A—H82A108.9C7B—C8B—H82B108.9
C7A—C8A—H82A108.9H81B—C8B—H82B107.7
H81A—C8A—H82A107.7N1B—C9B—C10B118.9 (2)
N1A—C9A—C10A119.28 (19)N1B—C9B—C8B116.3 (2)
N1A—C9A—C8A116.81 (18)C10B—C9B—C8B124.7 (2)
C10A—C9A—C8A123.91 (19)C9B—C10B—C4B118.9 (2)
C9A—C10A—C4A118.3 (2)C9B—C10B—C5B118.9 (3)
C9A—C10A—C5A119.6 (2)C4B—C10B—C5B122.2 (3)
C4A—C10A—C5A122.1 (2)H21—O2—H22102 (3)
O1B—N1B—C2B119.10 (19)
O1A—N1A—C2A—C3A178.4 (2)O1B—N1B—C2B—C3B179.9 (2)
C9A—N1A—C2A—C3A−2.0 (4)C9B—N1B—C2B—C3B−0.2 (3)
N1A—C2A—C3A—C4A0.9 (4)N1B—C2B—C3B—C4B0.4 (4)
C2A—C3A—C4A—C10A0.3 (4)C2B—C3B—C4B—C10B−0.5 (4)
C10A—C5A—C6A—C7A49.6 (3)C10B—C5B—C6B—C7B52.8 (3)
C5A—C6A—C7A—C8A−59.9 (3)C5B—C6B—C7B—C8B−61.4 (3)
C6A—C7A—C8A—C9A38.5 (3)C6B—C7B—C8B—C9B37.8 (3)
O1A—N1A—C9A—C10A−178.6 (2)O1B—N1B—C9B—C10B−179.94 (19)
C2A—N1A—C9A—C10A1.7 (4)C2B—N1B—C9B—C10B0.1 (3)
O1A—N1A—C9A—C8A0.5 (3)O1B—N1B—C9B—C8B−1.3 (3)
C2A—N1A—C9A—C8A−179.2 (2)C2B—N1B—C9B—C8B178.68 (18)
C7A—C8A—C9A—N1A172.3 (2)C7B—C8B—C9B—N1B174.06 (19)
C7A—C8A—C9A—C10A−8.7 (4)C7B—C8B—C9B—C10B−7.4 (3)
N1A—C9A—C10A—C4A−0.5 (4)N1B—C9B—C10B—C4B−0.2 (3)
C8A—C9A—C10A—C4A−179.5 (2)C8B—C9B—C10B—C4B−178.7 (2)
N1A—C9A—C10A—C5A178.5 (2)N1B—C9B—C10B—C5B178.77 (19)
C8A—C9A—C10A—C5A−0.6 (4)C8B—C9B—C10B—C5B0.3 (3)
C3A—C4A—C10A—C9A−0.5 (4)C3B—C4B—C10B—C9B0.4 (3)
C3A—C4A—C10A—C5A−179.4 (3)C3B—C4B—C10B—C5B−178.5 (2)
C6A—C5A—C10A—C9A−19.7 (4)C6B—C5B—C10B—C9B−22.2 (3)
C6A—C5A—C10A—C4A159.2 (3)C6B—C5B—C10B—C4B156.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H21···O1A0.96 (3)1.87 (3)2.825 (3)170 (3)
O2—H22···O1B0.95 (4)1.86 (3)2.799 (3)170 (3)
C2B—H2B···O1A0.932.533.454 (3)171
C3A—H3A···O2i0.932.503.392 (3)160
C3B—H3B···O2ii0.932.563.342 (4)142
C5A—H52A···O1Biii0.972.493.383 (4)153

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2025).

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