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The title mol­ecule, C19H23NO3, is an amphiphilic mol­ecule with a hydro­phobic alkyl chain and polar hydr­oxy groups. The mol­ecule is almost planar, with a dihedral angle between the aromatic rings of 8.52 (11)°. This conformation is, at least partially, a consequence of a strong intra­molecular hydrogen bond between the imine N atom and the ortho OH functionality, resulting in an S(6) ring. The mol­ecules are associated in a layered network built via O—H...O inter­molecular hydrogen bonds involving all the hydr­oxy groups. The mol­ecules in the layers are arranged in a head-to-head tail-to-tail fashion, and C—H...π inter­layer contacts further stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040408/zl2051sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040408/zl2051Isup2.hkl
Contains datablock I

CCDC reference: 660320

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.158
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg.
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Imines or Schiff bases are potential precursors for liquid crystalline compounds (Sudhakar et al., 2000) and polymers (Cerrada et al., 1996; Wang et al., 1996). We are interested in the synthesis and characterization of imines, as well as in the incorporation of reactive functional groups that can undergo radical or condensation polymerization reactions (Herrera, 2006).

The title compound, (I), is such a potential precursors for liquid crystalline materials. It is an amphiphilic molecule with a hydrophobic alkyl-chain and polar hydroxyl groups (Fig. 1), and the hexyloxy chains are in an all-trans conformation. The benzene rings bonded to the imine core functionality are almost co-planar, with a dihedral angle of 8.52 (11)°. A strong intramolecular hydrogen bond is observed, involving the imine N atom and the ortho-hydroxyl functionality of the benzylidene group, forming an S(6) ring motif (Bernstein et al., 1995). The planar conformation of the molecule is probably a consequence of this contact.

The packing of the molecules in the crystal is partially facilitated by intermolecular O—H···O hydrogen bonds involving the meta-hydroxyl functionality of the benzylidene as the H-donor and the ortho-hydroxyl group of a neighboring molecules as the acceptor. The resulting crystal structure exhibits a head-to-head tail-to-tail arrangement (Fig. 2). Molecules are thus arranged in layers, and the crystal structure is further stabilized through C—H···π interlayer contacts: C6—H6 and C14—H14 groups in the asymmetric unit are close to the centroids of the C1···C6 rings of symmetry related molecules at positions -1/2 + x, y, 1/2 - z and 3/2 - x, -1/2 + y, z, respectively. H···centroids separations are 2.74 for the former, and 2.82 Å for the latter contact, with corresponding C—H···centroid tilt angles of 132 and 134°.

The arrangement of molecules in the crystal structure of (I) is reminiscent of that stabilized for the starting material, 4-(hexyloxy)aniline (Herrera et al., 2005).

Related literature top

The crystal structure of the title compound is closely related to that of its starting material, 4-(hexyloxy)aniline (Herrera et al., 2005; Herrera, 2006). For related imines as potential precursors for liquid crystalline compounds and polymers, see: Sudhakar et al. (2000); Cerrada et al. (1996); Wang et al. (1996). For the graph-set notation S(6), see: Bernstein et al. (1995).

Experimental top

To a stirred solution of 2,5-dihydroxybenzaldehyde (0.24 g, 1.76 mmol) in 60 ml of dry ethanol was added 2.10 mmol (0.41 g) of 4-hexyloxyaniline (Herrera et al., 2005) under Ar. The mixture was heated to 325 K for 4 h, and then cooled to room temperature. Ethanol was evaporated, and finally the resulting solid product was recrystallized from petroleum ether, affording thin orange crystals (yield 0.50 g, 91% based on aldehyde; m.p. 389 K). Analysis found: C 72.83, H 7.32, O 15.33, N 4.45%; Calcd. for C19H23NO3: C 72.82, H 7.40, O 15.32, N 4.47%. 1H NMR (400 MHz, DMSO-d6): δ 0.88 (t, J = 6.4 Hz, 3H, CH3), 1.42–1.30 (m, J = 7.2 Hz, 6H, CH2), 1.71 (m, J = 6.8 Hz, 2H, CH2), 3.97 (t, J = 6.8 Hz, 6.4 Hz, 2H, OCH2), 6.79 (m, J = 8.7 Hz, 2H, Ph), 6.99 (m, 3H, Ph), 7.36 (d, J = 8.8 Hz, 2H, Ph), 8.82 (s, 1H, NCH), 9.08 (s, 1H, OH), 12.50 (s, 1H, OH).

Refinement top

All C-bonded H atoms were placed in idealized positions and refined using a riding model; C—H bond lengths were set to 0.96 (methyl CH3 group, considered as a free to rotate rigid group), 0.97 (methylene CH2 groups) or 0.93 Å (aromatic CH). Hydroxyl H atoms were found in a difference map and refined with a regularized geometry (O—H = 0.82 Å; C—O—H = 109.5°) allowing free rotation about the C—O axis. Isotropic displacement parameters were fixed for all H atoms: Uiso(H) = 1.2 Ueq(carrier C) for methylene and aromatic H atoms, Uiso(H) = 1.5 Ueq(carrier atom) for methyl and hydroxyl H atoms.

Structure description top

Imines or Schiff bases are potential precursors for liquid crystalline compounds (Sudhakar et al., 2000) and polymers (Cerrada et al., 1996; Wang et al., 1996). We are interested in the synthesis and characterization of imines, as well as in the incorporation of reactive functional groups that can undergo radical or condensation polymerization reactions (Herrera, 2006).

The title compound, (I), is such a potential precursors for liquid crystalline materials. It is an amphiphilic molecule with a hydrophobic alkyl-chain and polar hydroxyl groups (Fig. 1), and the hexyloxy chains are in an all-trans conformation. The benzene rings bonded to the imine core functionality are almost co-planar, with a dihedral angle of 8.52 (11)°. A strong intramolecular hydrogen bond is observed, involving the imine N atom and the ortho-hydroxyl functionality of the benzylidene group, forming an S(6) ring motif (Bernstein et al., 1995). The planar conformation of the molecule is probably a consequence of this contact.

The packing of the molecules in the crystal is partially facilitated by intermolecular O—H···O hydrogen bonds involving the meta-hydroxyl functionality of the benzylidene as the H-donor and the ortho-hydroxyl group of a neighboring molecules as the acceptor. The resulting crystal structure exhibits a head-to-head tail-to-tail arrangement (Fig. 2). Molecules are thus arranged in layers, and the crystal structure is further stabilized through C—H···π interlayer contacts: C6—H6 and C14—H14 groups in the asymmetric unit are close to the centroids of the C1···C6 rings of symmetry related molecules at positions -1/2 + x, y, 1/2 - z and 3/2 - x, -1/2 + y, z, respectively. H···centroids separations are 2.74 for the former, and 2.82 Å for the latter contact, with corresponding C—H···centroid tilt angles of 132 and 134°.

The arrangement of molecules in the crystal structure of (I) is reminiscent of that stabilized for the starting material, 4-(hexyloxy)aniline (Herrera et al., 2005).

The crystal structure of the title compound is closely related to that of its starting material, 4-(hexyloxy)aniline (Herrera et al., 2005; Herrera, 2006). For related imines as potential precursors for liquid crystalline compounds and polymers, see: Sudhakar et al. (2000); Cerrada et al. (1996); Wang et al. (1996). For the graph-set notation S(6), see: Bernstein et al. (1995).

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus (Sheldrick, 1998); molecular graphics: SHELXTL-Plus (Sheldrick, 1998) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 1998).

Figures top
[Figure 1] Fig. 1. The structure of (I) with displacement ellipsoids for non-H atoms at the 50% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the hydrogen-bonding scheme (dashed lines). The red molecule corresponds to the asymmetric unit, while the green molecule is related to the asymmetric unit through operator 1 - x, 1 - y, 1 - z.
2-[(4-Hexyloxyphenyl)iminomethyl]benzene-1,4-diol top
Crystal data top
C19H23NO3Dx = 1.221 Mg m3
Mr = 313.38Melting point: 389 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 80 reflections
a = 7.5559 (10) Åθ = 3.9–12.2°
b = 12.3351 (15) ŵ = 0.08 mm1
c = 36.597 (4) ÅT = 296 K
V = 3411.0 (7) Å3Plate, orange
Z = 80.60 × 0.54 × 0.16 mm
F(000) = 1344
Data collection top
Bruker P4
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tube, FN4θmax = 25.0°, θmin = 2.2°
Graphite monochromatorh = 81
ω scansk = 141
3894 measured reflectionsl = 431
2996 independent reflections3 standard reflections every 97 reflections
1762 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.158 w = 1/[σ2(Fo2) + (0.0794P)2 + 0.2325P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2996 reflectionsΔρmax = 0.22 e Å3
212 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXTL-Plus (Sheldrick, 1998), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0027 (6)
Crystal data top
C19H23NO3V = 3411.0 (7) Å3
Mr = 313.38Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.5559 (10) ŵ = 0.08 mm1
b = 12.3351 (15) ÅT = 296 K
c = 36.597 (4) Å0.60 × 0.54 × 0.16 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.021
3894 measured reflections3 standard reflections every 97 reflections
2996 independent reflections intensity decay: 1%
1762 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
2996 reflectionsΔρmin = 0.18 e Å3
212 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3979 (3)0.76235 (16)0.27705 (6)0.0461 (6)
C20.4892 (3)0.77627 (16)0.31019 (6)0.0449 (6)
C30.5559 (3)0.87943 (16)0.31853 (6)0.0483 (6)
H3C0.61880.88970.34010.058*
C40.5297 (3)0.96557 (16)0.29535 (6)0.0489 (6)
C50.4367 (3)0.95043 (18)0.26302 (6)0.0497 (6)
H5C0.41721.00880.24740.060*
C60.3732 (3)0.84884 (16)0.25397 (6)0.0513 (6)
H6C0.31320.83890.23200.062*
C70.5198 (3)0.68504 (18)0.33457 (6)0.0502 (6)
H7A0.58890.69480.35530.060*
N80.4534 (2)0.59150 (14)0.32798 (5)0.0502 (5)
C90.4813 (3)0.49935 (17)0.35029 (6)0.0480 (6)
C100.5530 (4)0.50164 (19)0.38539 (6)0.0607 (7)
H10B0.58730.56740.39560.073*
C110.5733 (4)0.40725 (19)0.40491 (6)0.0645 (7)
H11B0.62050.40990.42840.077*
C120.5246 (3)0.30830 (19)0.39013 (6)0.0550 (6)
C130.4544 (3)0.30473 (18)0.35534 (6)0.0567 (7)
H13B0.42220.23890.34490.068*
C140.4327 (3)0.40059 (17)0.33616 (6)0.0550 (6)
H14A0.38340.39800.31290.066*
O150.5508 (3)0.22029 (13)0.41222 (5)0.0722 (6)
C160.4815 (4)0.11738 (18)0.40096 (7)0.0617 (7)
H16A0.54760.08960.38030.074*
H16B0.35820.12430.39400.074*
C170.4999 (4)0.04240 (19)0.43334 (7)0.0651 (7)
H17B0.62280.04130.44100.078*
H17C0.43060.07110.45350.078*
C180.4411 (4)0.07187 (19)0.42573 (7)0.0727 (8)
H18A0.50810.09990.40520.087*
H18B0.31720.07100.41880.087*
C190.4643 (4)0.1480 (2)0.45808 (7)0.0788 (9)
H19A0.58580.14260.46640.095*
H19B0.38920.12260.47780.095*
C200.4251 (6)0.2609 (2)0.45176 (9)0.1174 (14)
H20A0.49270.28460.43070.141*
H20B0.30080.26690.44540.141*
C210.4617 (5)0.3377 (3)0.48262 (10)0.1139 (13)
H21A0.42620.40950.47570.171*
H21B0.39640.31540.50380.171*
H21C0.58600.33720.48810.171*
O220.3302 (2)0.66392 (11)0.26689 (4)0.0615 (5)
H220.35040.61920.28290.092*
O230.5998 (3)1.06534 (11)0.30460 (4)0.0687 (6)
H230.60401.10400.28640.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0512 (14)0.0380 (12)0.0490 (12)0.0011 (11)0.0011 (11)0.0034 (10)
C20.0515 (14)0.0408 (12)0.0425 (11)0.0051 (10)0.0028 (10)0.0010 (10)
C30.0604 (15)0.0448 (13)0.0398 (11)0.0015 (12)0.0009 (11)0.0040 (10)
C40.0633 (15)0.0364 (12)0.0469 (13)0.0008 (11)0.0070 (11)0.0047 (10)
C50.0583 (15)0.0404 (12)0.0505 (13)0.0051 (12)0.0014 (11)0.0039 (10)
C60.0588 (14)0.0479 (13)0.0471 (12)0.0034 (13)0.0085 (11)0.0015 (11)
C70.0593 (15)0.0491 (14)0.0422 (12)0.0033 (12)0.0008 (11)0.0011 (10)
N80.0594 (12)0.0404 (11)0.0508 (11)0.0024 (10)0.0006 (9)0.0041 (8)
C90.0561 (14)0.0418 (12)0.0460 (13)0.0032 (11)0.0004 (11)0.0044 (10)
C100.0833 (19)0.0459 (13)0.0529 (14)0.0040 (13)0.0095 (13)0.0008 (11)
C110.089 (2)0.0542 (15)0.0503 (14)0.0056 (14)0.0184 (13)0.0056 (12)
C120.0646 (16)0.0467 (13)0.0538 (14)0.0001 (12)0.0026 (12)0.0097 (11)
C130.0730 (17)0.0445 (13)0.0527 (14)0.0039 (13)0.0084 (13)0.0019 (11)
C140.0685 (16)0.0502 (14)0.0463 (12)0.0027 (13)0.0084 (12)0.0047 (11)
O150.1023 (15)0.0477 (10)0.0667 (11)0.0070 (10)0.0228 (10)0.0171 (8)
C160.0777 (18)0.0459 (14)0.0614 (15)0.0004 (13)0.0003 (14)0.0083 (12)
C170.0819 (19)0.0511 (14)0.0624 (15)0.0053 (14)0.0054 (14)0.0136 (12)
C180.093 (2)0.0542 (15)0.0706 (17)0.0019 (15)0.0001 (15)0.0139 (13)
C190.102 (2)0.0641 (17)0.0703 (17)0.0069 (16)0.0087 (16)0.0165 (14)
C200.196 (4)0.0631 (19)0.093 (2)0.014 (2)0.020 (3)0.0166 (17)
C210.139 (3)0.080 (2)0.123 (3)0.007 (2)0.014 (2)0.042 (2)
O220.0849 (13)0.0416 (9)0.0581 (9)0.0041 (9)0.0170 (9)0.0001 (7)
O230.1063 (14)0.0424 (9)0.0574 (10)0.0136 (10)0.0045 (11)0.0020 (7)
Geometric parameters (Å, º) top
C1—O221.369 (2)C13—H13B0.9300
C1—C61.374 (3)C14—H14A0.9300
C1—C21.406 (3)O15—C161.434 (3)
C2—C31.402 (3)C16—C171.510 (3)
C2—C71.455 (3)C16—H16A0.9700
C3—C41.374 (3)C16—H16B0.9700
C3—H3C0.9300C17—C181.504 (3)
C4—O231.382 (2)C17—H17B0.9700
C4—C51.388 (3)C17—H17C0.9700
C5—C61.382 (3)C18—C191.521 (3)
C5—H5C0.9300C18—H18A0.9700
C6—H6C0.9300C18—H18B0.9700
C7—N81.281 (3)C19—C201.443 (4)
C7—H7A0.9300C19—H19A0.9700
N8—C91.415 (3)C19—H19B0.9700
C9—C141.374 (3)C20—C211.500 (4)
C9—C101.395 (3)C20—H20A0.9700
C10—C111.375 (3)C20—H20B0.9700
C10—H10B0.9300C21—H21A0.9600
C11—C121.385 (3)C21—H21B0.9600
C11—H11B0.9300C21—H21C0.9600
C12—O151.368 (3)O22—H220.8200
C12—C131.380 (3)O23—H230.8200
C13—C141.385 (3)
O22—C1—C6118.11 (19)C12—O15—C16118.69 (18)
O22—C1—C2121.74 (18)O15—C16—C17106.5 (2)
C6—C1—C2120.1 (2)O15—C16—H16A110.4
C3—C2—C1118.36 (19)C17—C16—H16A110.4
C3—C2—C7120.8 (2)O15—C16—H16B110.4
C1—C2—C7120.8 (2)C17—C16—H16B110.4
C4—C3—C2121.0 (2)H16A—C16—H16B108.6
C4—C3—H3C119.5C18—C17—C16113.7 (2)
C2—C3—H3C119.5C18—C17—H17B108.8
C3—C4—O23118.8 (2)C16—C17—H17B108.8
C3—C4—C5119.7 (2)C18—C17—H17C108.8
O23—C4—C5121.50 (19)C16—C17—H17C108.8
C6—C5—C4120.1 (2)H17B—C17—H17C107.7
C6—C5—H5C119.9C17—C18—C19113.6 (2)
C4—C5—H5C119.9C17—C18—H18A108.8
C1—C6—C5120.6 (2)C19—C18—H18A108.8
C1—C6—H6C119.7C17—C18—H18B108.8
C5—C6—H6C119.7C19—C18—H18B108.8
N8—C7—C2121.3 (2)H18A—C18—H18B107.7
N8—C7—H7A119.4C20—C19—C18116.6 (2)
C2—C7—H7A119.4C20—C19—H19A108.1
C7—N8—C9123.80 (19)C18—C19—H19A108.1
C14—C9—C10117.9 (2)C20—C19—H19B108.1
C14—C9—N8117.09 (19)C18—C19—H19B108.1
C10—C9—N8125.0 (2)H19A—C19—H19B107.3
C11—C10—C9120.3 (2)C19—C20—C21116.8 (3)
C11—C10—H10B119.8C19—C20—H20A108.1
C9—C10—H10B119.8C21—C20—H20A108.1
C10—C11—C12120.9 (2)C19—C20—H20B108.1
C10—C11—H11B119.5C21—C20—H20B108.1
C12—C11—H11B119.5H20A—C20—H20B107.3
O15—C12—C13125.1 (2)C20—C21—H21A109.5
O15—C12—C11115.5 (2)C20—C21—H21B109.5
C13—C12—C11119.4 (2)H21A—C21—H21B109.5
C12—C13—C14119.1 (2)C20—C21—H21C109.5
C12—C13—H13B120.5H21A—C21—H21C109.5
C14—C13—H13B120.5H21B—C21—H21C109.5
C9—C14—C13122.3 (2)C1—O22—H22109.5
C9—C14—H14A118.8C4—O23—H23109.5
C13—C14—H14A118.8
O22—C1—C2—C3179.5 (2)C14—C9—C10—C110.1 (4)
C6—C1—C2—C31.0 (3)N8—C9—C10—C11179.5 (2)
O22—C1—C2—C71.9 (3)C9—C10—C11—C120.5 (4)
C6—C1—C2—C7178.7 (2)C10—C11—C12—O15179.9 (2)
C1—C2—C3—C41.4 (3)C10—C11—C12—C130.1 (4)
C7—C2—C3—C4179.0 (2)O15—C12—C13—C14179.0 (2)
C2—C3—C4—O23179.3 (2)C11—C12—C13—C140.7 (4)
C2—C3—C4—C50.4 (3)C10—C9—C14—C130.7 (4)
C3—C4—C5—C61.0 (3)N8—C9—C14—C13179.7 (2)
O23—C4—C5—C6177.9 (2)C12—C13—C14—C91.1 (4)
O22—C1—C6—C5179.2 (2)C13—C12—O15—C168.2 (4)
C2—C1—C6—C50.3 (4)C11—C12—O15—C16171.5 (2)
C4—C5—C6—C11.3 (4)C12—O15—C16—C17169.6 (2)
C3—C2—C7—N8177.1 (2)O15—C16—C17—C18177.2 (2)
C1—C2—C7—N85.3 (3)C16—C17—C18—C19178.5 (2)
C2—C7—N8—C9178.73 (19)C17—C18—C19—C20174.8 (3)
C7—N8—C9—C14167.1 (2)C18—C19—C20—C21175.2 (3)
C7—N8—C9—C1013.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22—H22···N80.821.852.581 (2)147
O23—H23···O22i0.822.142.933 (2)162
Symmetry code: (i) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H23NO3
Mr313.38
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)7.5559 (10), 12.3351 (15), 36.597 (4)
V3)3411.0 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.60 × 0.54 × 0.16
Data collection
DiffractometerBruker P4
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3894, 2996, 1762
Rint0.021
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.158, 1.03
No. of reflections2996
No. of parameters212
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.18

Computer programs: XSCANS (Siemens, 1996), SHELXTL-Plus (Sheldrick, 1998) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22—H22···N80.821.852.581 (2)146.9
O23—H23···O22i0.822.142.933 (2)161.5
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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