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The title compound, C22H18N2O2, is a biologically active 1,5-benzodiazepine derivative, containing three planar six-membered rings and one nonplanar seven-membered ring. The six-membered rings A (phenol), B (fused benzene) and C (methoxyphenyl) are oriented with respect to each other at dihedral angles of 39.22 (2) (A/B), 87.31 (3) (A/C) and 54.42 (3)° (B/C). The seven-membered ring adopts a near-boat conformation. In the crystal structure, intra­molecular O—H...N and inter­molecular C—H...O hydrogen bonds are present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034630/hk2293sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034630/hk2293Isup2.hkl
Contains datablock I

CCDC reference: 657806

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.116
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

The title compound belongs to an important class of the pharmacologically pre-eminent 1,5-benzodiazepines which are extensively studied for medicinal activities (Krapcho & Turk, 1966). In recent years, benzodiazepines have replaced barbiturates which were used once for the purpose of hypnotic effects, owing to their less toxic and less severe withdrawal effects (Gringauz, 1999). The importance of 1,5-benzodiazepines, in particular is evident from the pharmaceutical application of Globazam (Butcher & Hamor, 1985). The difficulties encountered in the cyclization of these seven-membered heterocycles limited their structural studies. In view of the importance of this class of compounds, the title compound, (I), has been synthesized and its crystal structure is reported here.

A perspective view of (I) is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Structural Database, Version 5.28, November 2006; Allen, 2002; Mogul, Version 1.1; Bruno et al., 2004). The seven membered diazepine ring has a fragment N1—C10—C11—N2, which is conjugated with the adjacent benzene ring. Like azepines, diazepines are not planar and generally adopt boat conformation (Armarego, 1977).

The rings A (C1—C6), B (C10—C15) and C (C16—C21) are, of course, planar and dihedral angles between them are A/B = 39.22 (2)°, A/C = 87.31 (3)° and B/C = 54.42 (3)°. The seven membered ring D (N1/N2/C7—C11) is non-planar and adopts nearly boat conformation.

In the crystal structure, intramolecular O—H···N and intermolecular C—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For bond-length data, see: Allen (2002); Bruno et al. (2004). For general background, see: Krapcho & Turk (1966); Gringauz (1999); Butcher & Hamor (1985); Armarego (1977). For related literature, see: Ahmed et al. (1990).

Experimental top

1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione (2.7 g, 10 mmol), prepared according to the reported procedure (Ahmed et al., 1990), was subjected to cyclo-condensation with phenylene diamine (1,08 g, 10 mmol) using toluene (100 ml) as solvent to get the title compound (yield; 62%, m.p.481–483 K). Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of dichloromethane solution.

Refinement top

H1 (for OH) was located in difference syntheses and refined isotropically [O1—H1 = 0.92 (2) Å and Uiso(H) = 0.088 (6) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Structure description top

The title compound belongs to an important class of the pharmacologically pre-eminent 1,5-benzodiazepines which are extensively studied for medicinal activities (Krapcho & Turk, 1966). In recent years, benzodiazepines have replaced barbiturates which were used once for the purpose of hypnotic effects, owing to their less toxic and less severe withdrawal effects (Gringauz, 1999). The importance of 1,5-benzodiazepines, in particular is evident from the pharmaceutical application of Globazam (Butcher & Hamor, 1985). The difficulties encountered in the cyclization of these seven-membered heterocycles limited their structural studies. In view of the importance of this class of compounds, the title compound, (I), has been synthesized and its crystal structure is reported here.

A perspective view of (I) is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Structural Database, Version 5.28, November 2006; Allen, 2002; Mogul, Version 1.1; Bruno et al., 2004). The seven membered diazepine ring has a fragment N1—C10—C11—N2, which is conjugated with the adjacent benzene ring. Like azepines, diazepines are not planar and generally adopt boat conformation (Armarego, 1977).

The rings A (C1—C6), B (C10—C15) and C (C16—C21) are, of course, planar and dihedral angles between them are A/B = 39.22 (2)°, A/C = 87.31 (3)° and B/C = 54.42 (3)°. The seven membered ring D (N1/N2/C7—C11) is non-planar and adopts nearly boat conformation.

In the crystal structure, intramolecular O—H···N and intermolecular C—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

For bond-length data, see: Allen (2002); Bruno et al. (2004). For general background, see: Krapcho & Turk (1966); Gringauz (1999); Butcher & Hamor (1985); Armarego (1977). For related literature, see: Ahmed et al. (1990).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. Preparation of the title compound.
2-[(1E,4E)-2-(4-Methoxyphenyl)-3H-benzo[b][1,4]diazepin-4-yl]phenol top
Crystal data top
C22H18N2O2F(000) = 720
Mr = 342.38Dx = 1.337 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3874 reflections
a = 9.8203 (7) Åθ = 2.3–28.3°
b = 16.2920 (12) ŵ = 0.09 mm1
c = 11.0178 (8) ÅT = 298 K
β = 105.203 (1)°Block, yellow
V = 1701.1 (2) Å30.33 × 0.30 × 0.27 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4220 independent reflections
Radiation source: fine-focus sealed tube3022 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω and φ scansθmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.897, Tmax = 0.980k = 2120
9963 measured reflectionsl = 147
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.3204P]
where P = (Fo2 + 2Fc2)/3
3928 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C22H18N2O2V = 1701.1 (2) Å3
Mr = 342.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.8203 (7) ŵ = 0.09 mm1
b = 16.2920 (12) ÅT = 298 K
c = 11.0178 (8) Å0.33 × 0.30 × 0.27 mm
β = 105.203 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4220 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3022 reflections with I > 2σ(I)
Tmin = 0.897, Tmax = 0.980Rint = 0.017
9963 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.20 e Å3
3928 reflectionsΔρmin = 0.18 e Å3
239 parameters
Special details top

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.

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) top
xyzUiso*/Ueq
O10.03533 (12)0.86806 (6)0.61876 (11)0.0555 (3)
H10.039 (2)0.8542 (13)0.5869 (19)0.088 (6)*
O20.72160 (11)1.13972 (6)1.11673 (10)0.0535 (3)
N10.51345 (11)0.89159 (7)0.66528 (10)0.0416 (3)
N20.19812 (11)0.87562 (7)0.55763 (11)0.0411 (3)
C10.00688 (14)0.94474 (8)0.66394 (13)0.0415 (3)
C20.10065 (16)0.98059 (9)0.72371 (15)0.0519 (4)
H2A0.18030.95170.72980.062*
C30.07683 (17)1.05816 (9)0.77385 (15)0.0560 (4)
H3A0.13931.08080.81500.067*
C40.03994 (17)1.10289 (9)0.76347 (14)0.0516 (4)
H4A0.05641.15520.79790.062*
C50.13119 (15)1.06868 (8)0.70144 (13)0.0433 (3)
H5A0.20781.09950.69260.052*
C60.11271 (13)0.98942 (8)0.65144 (11)0.0365 (3)
C70.21520 (12)0.95158 (8)0.59207 (12)0.0364 (3)
C80.34185 (13)0.99771 (8)0.57406 (12)0.0383 (3)
H8A0.33101.05620.58480.046*
H8B0.35400.98790.49070.046*
C90.46674 (13)0.96498 (8)0.67378 (12)0.0375 (3)
C100.44695 (14)0.83856 (8)0.56771 (12)0.0401 (3)
C110.29969 (14)0.83181 (8)0.51475 (13)0.0409 (3)
C120.24887 (16)0.77175 (9)0.42316 (15)0.0513 (4)
H12A0.15200.76620.38990.062*
C130.33820 (17)0.72090 (9)0.38116 (16)0.0557 (4)
H13A0.30230.68370.31670.067*
C140.48251 (17)0.72541 (9)0.43547 (16)0.0548 (4)
H14A0.54340.69010.40910.066*
C150.53528 (15)0.78209 (9)0.52820 (14)0.0488 (3)
H15A0.63180.78320.56590.059*
C160.53499 (13)1.01454 (8)0.78517 (12)0.0375 (3)
C170.51971 (15)1.09936 (8)0.79032 (14)0.0457 (3)
H17A0.46731.12690.71950.055*
C180.58070 (15)1.14386 (8)0.89838 (14)0.0478 (3)
H18A0.56831.20040.90000.057*
C190.65993 (13)1.10332 (8)1.00349 (12)0.0411 (3)
C200.68271 (15)1.01928 (8)0.99855 (13)0.0451 (3)
H20A0.74040.99251.06770.054*
C210.62032 (13)0.97595 (8)0.89211 (12)0.0409 (3)
H21A0.63480.91960.89060.049*
C220.68065 (19)1.22061 (10)1.13736 (17)0.0611 (4)
H22A0.73181.23841.21970.092*
H22B0.58131.22181.13100.092*
H22C0.70101.25661.07530.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0516 (6)0.0463 (6)0.0779 (8)0.0086 (5)0.0334 (6)0.0049 (5)
O20.0569 (6)0.0490 (6)0.0512 (6)0.0015 (5)0.0083 (5)0.0068 (5)
N10.0382 (6)0.0435 (6)0.0450 (6)0.0038 (5)0.0145 (5)0.0012 (5)
N20.0369 (6)0.0407 (6)0.0487 (6)0.0002 (4)0.0167 (5)0.0025 (5)
C10.0419 (7)0.0408 (7)0.0450 (7)0.0035 (5)0.0169 (6)0.0073 (6)
C20.0490 (8)0.0510 (8)0.0648 (9)0.0061 (6)0.0313 (7)0.0131 (7)
C30.0616 (9)0.0541 (9)0.0633 (10)0.0170 (7)0.0360 (8)0.0089 (7)
C40.0619 (9)0.0415 (7)0.0558 (9)0.0115 (6)0.0233 (7)0.0014 (6)
C50.0430 (7)0.0392 (7)0.0494 (8)0.0038 (5)0.0155 (6)0.0042 (6)
C60.0351 (6)0.0379 (6)0.0377 (6)0.0056 (5)0.0119 (5)0.0059 (5)
C70.0339 (6)0.0393 (6)0.0367 (6)0.0026 (5)0.0105 (5)0.0040 (5)
C80.0379 (6)0.0390 (6)0.0401 (7)0.0000 (5)0.0143 (5)0.0037 (5)
C90.0329 (6)0.0404 (7)0.0426 (7)0.0004 (5)0.0159 (5)0.0038 (5)
C100.0415 (7)0.0391 (6)0.0425 (7)0.0025 (5)0.0163 (5)0.0012 (5)
C110.0409 (7)0.0379 (6)0.0478 (7)0.0011 (5)0.0183 (6)0.0006 (5)
C120.0453 (8)0.0456 (7)0.0636 (9)0.0032 (6)0.0156 (7)0.0091 (7)
C130.0622 (9)0.0455 (8)0.0635 (10)0.0025 (7)0.0235 (8)0.0146 (7)
C140.0593 (9)0.0464 (8)0.0671 (10)0.0065 (7)0.0316 (8)0.0072 (7)
C150.0438 (7)0.0482 (8)0.0584 (9)0.0067 (6)0.0204 (6)0.0013 (7)
C160.0326 (6)0.0402 (6)0.0428 (7)0.0004 (5)0.0153 (5)0.0025 (5)
C170.0450 (7)0.0404 (7)0.0491 (8)0.0013 (6)0.0074 (6)0.0064 (6)
C180.0491 (8)0.0343 (6)0.0588 (9)0.0006 (6)0.0122 (6)0.0003 (6)
C190.0354 (6)0.0454 (7)0.0443 (7)0.0029 (5)0.0138 (5)0.0025 (6)
C200.0443 (7)0.0460 (7)0.0448 (7)0.0063 (6)0.0116 (6)0.0055 (6)
C210.0412 (7)0.0382 (6)0.0457 (7)0.0041 (5)0.0153 (6)0.0028 (6)
C220.0650 (10)0.0555 (9)0.0642 (10)0.0023 (8)0.0194 (8)0.0144 (8)
Geometric parameters (Å, º) top
C1—O11.3467 (17)C12—C131.372 (2)
C1—C21.3931 (19)C12—H12A0.9300
C1—C61.4188 (17)C13—C141.388 (2)
C2—C31.374 (2)C13—H13A0.9300
C2—H2A0.9300C14—C151.374 (2)
C3—C41.388 (2)C14—H14A0.9300
C3—H3A0.9300C15—H15A0.9300
C4—C51.3791 (19)C16—C171.3928 (18)
C4—H4A0.9300C16—C211.4028 (18)
C5—C61.3970 (18)C17—C181.388 (2)
C5—H5A0.9300C17—H17A0.9300
C6—C71.4718 (16)C18—C191.3821 (19)
C7—N21.2924 (16)C18—H18A0.9300
C7—C81.5101 (17)C19—O21.3707 (16)
C8—C91.5129 (18)C19—C201.3907 (19)
C8—H8A0.9700C20—C211.3684 (19)
C8—H8B0.9700C20—H20A0.9300
C9—N11.2927 (16)C21—H21A0.9300
C9—C161.4751 (18)C22—O21.4135 (18)
C10—N11.4001 (17)C22—H22A0.9600
C10—C151.4095 (18)C22—H22B0.9600
C10—C111.4146 (19)C22—H22C0.9600
C11—C121.4003 (19)O1—H10.92 (2)
C11—N21.4053 (16)
O1—C1—C2117.71 (12)C11—C12—H12A119.1
O1—C1—C6122.46 (11)C12—C13—C14119.56 (14)
C2—C1—C6119.83 (13)C12—C13—H13A120.2
C3—C2—C1120.77 (13)C14—C13—H13A120.2
C3—C2—H2A119.6C15—C14—C13119.96 (13)
C1—C2—H2A119.6C15—C14—H14A120.0
C2—C3—C4120.44 (13)C13—C14—H14A120.0
C2—C3—H3A119.8C14—C15—C10121.72 (14)
C4—C3—H3A119.8C14—C15—H15A119.1
C5—C4—C3119.13 (14)C10—C15—H15A119.1
C5—C4—H4A120.4C17—C16—C21117.23 (12)
C3—C4—H4A120.4C17—C16—C9123.14 (12)
C4—C5—C6122.33 (13)C21—C16—C9119.63 (11)
C4—C5—H5A118.8C18—C17—C16121.75 (13)
C6—C5—H5A118.8C18—C17—H17A119.1
C5—C6—C1117.46 (11)C16—C17—H17A119.1
C5—C6—C7121.95 (11)C19—C18—C17119.37 (13)
C1—C6—C7120.54 (11)C19—C18—H18A120.3
N2—C7—C6118.71 (11)C17—C18—H18A120.3
N2—C7—C8119.07 (11)O2—C19—C18124.97 (12)
C6—C7—C8122.19 (11)O2—C19—C20115.11 (12)
C7—C8—C9105.54 (10)C18—C19—C20119.91 (13)
C7—C8—H8A110.6C21—C20—C19120.07 (13)
C9—C8—H8A110.6C21—C20—H20A120.0
C7—C8—H8B110.6C19—C20—H20A120.0
C9—C8—H8B110.6C20—C21—C16121.54 (12)
H8A—C8—H8B108.8C20—C21—H21A119.2
N1—C9—C16118.30 (12)C16—C21—H21A119.2
N1—C9—C8120.58 (12)O2—C22—H22A109.5
C16—C9—C8121.08 (11)O2—C22—H22B109.5
N1—C10—C15116.04 (12)H22A—C22—H22B109.5
N1—C10—C11125.82 (11)O2—C22—H22C109.5
C15—C10—C11117.85 (12)H22A—C22—H22C109.5
C12—C11—N2116.55 (12)H22B—C22—H22C109.5
C12—C11—C10118.96 (12)C9—N1—C10121.56 (11)
N2—C11—C10124.11 (12)C7—N2—C11122.42 (11)
C13—C12—C11121.76 (14)C1—O1—H1105.1 (13)
C13—C12—H12A119.1C19—O2—C22118.25 (12)
O1—C1—C2—C3178.92 (14)C13—C14—C15—C102.2 (2)
C6—C1—C2—C31.7 (2)N1—C10—C15—C14178.36 (13)
C1—C2—C3—C41.3 (2)C11—C10—C15—C144.2 (2)
C2—C3—C4—C50.4 (2)N1—C9—C16—C17163.12 (12)
C3—C4—C5—C61.8 (2)C8—C9—C16—C1719.07 (18)
C4—C5—C6—C11.4 (2)N1—C9—C16—C2116.64 (17)
C4—C5—C6—C7176.28 (13)C8—C9—C16—C21161.17 (11)
O1—C1—C6—C5179.68 (13)C21—C16—C17—C182.89 (19)
C2—C1—C6—C50.36 (19)C9—C16—C17—C18177.35 (12)
O1—C1—C6—C72.6 (2)C16—C17—C18—C190.6 (2)
C2—C1—C6—C7178.09 (12)C17—C18—C19—O2177.80 (12)
C5—C6—C7—N2174.04 (12)C17—C18—C19—C202.7 (2)
C1—C6—C7—N23.59 (18)O2—C19—C20—C21176.78 (12)
C5—C6—C7—C83.92 (19)C18—C19—C20—C213.64 (19)
C1—C6—C7—C8178.45 (11)C19—C20—C21—C161.3 (2)
N2—C7—C8—C973.70 (14)C17—C16—C21—C201.90 (19)
C6—C7—C8—C9104.25 (13)C9—C16—C21—C20178.32 (11)
C7—C8—C9—N171.22 (14)C16—C9—N1—C10174.75 (11)
C7—C8—C9—C16106.54 (12)C8—C9—N1—C103.08 (18)
N1—C10—C11—C12175.71 (13)C15—C10—N1—C9148.84 (12)
C15—C10—C11—C122.14 (19)C11—C10—N1—C937.48 (19)
N1—C10—C11—N23.1 (2)C6—C7—N2—C11171.94 (11)
C15—C10—C11—N2170.50 (12)C8—C7—N2—C116.09 (19)
N2—C11—C12—C13174.98 (13)C12—C11—N2—C7147.30 (13)
C10—C11—C12—C131.8 (2)C10—C11—N2—C739.91 (19)
C11—C12—C13—C143.8 (2)C18—C19—O2—C2212.9 (2)
C12—C13—C14—C151.8 (2)C20—C19—O2—C22167.51 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.92 (2)1.71 (2)2.5563 (17)151.5 (19)
C14—H14A···O2i0.932.533.406 (2)156
Symmetry code: (i) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC22H18N2O2
Mr342.38
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)9.8203 (7), 16.2920 (12), 11.0178 (8)
β (°) 105.203 (1)
V3)1701.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.33 × 0.30 × 0.27
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.897, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
9963, 4220, 3022
Rint0.017
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.116, 1.01
No. of reflections3928
No. of parameters239
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.92 (2)1.71 (2)2.5563 (17)151.5 (19)
C14—H14A···O2i0.932.533.406 (2)156
Symmetry code: (i) x+3/2, y1/2, z+3/2.
 

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