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The title compound, C14H8N2O4, was synthesized by reacting p-nitro­anthranilic acid and benzoyl chloride at ambient temperature. The structure is stabilized by an intra­molecular C—H...O hydrogen bond and an inter­molecular C—H...O hydrogen bond. Additionally, weak π–π stacking inter­actions [centroid–centroid distance 3.6 (17) Å] between adjacent mol­ecules further stabilize the crystal structure and form parallel layers along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046168/ww2096sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046168/ww2096Isup2.hkl
Contains datablock I

CCDC reference: 667287

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.171
  • Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 - C13 .. 5.52 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 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 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Recent work by the medicinal chemists had led to a number of drugs related uses being found for this class of heterocyclic compound. Fenton et al. have described plasma lipid altering characteristics of a series of 2-substituted-4H-3,1-benzoxazin-4-one as high density lipoprotein elevators for the treatment of patients suffering from hyperlipoproteinemia and associated diseases (Fenton et al., 1989). 2-Substituted-4H-3,1-benzoxazin-4-one base has been utilized as potent inhibitors of human leukocyte elastase (Krantz et al., 1990) and serine proteases (Gutschow et al., 1998). The National Cancer Institute, Washington, USA has also shown interest in 1-[3-(7-chloro-4-oxo-3,1-benzoxazin-4-yl) phenyl] methyl pyridinium chloride (NSC-341, 964) (Johnson & Pattison, 1986), evaluating its anti-neoplastic activity. Initial studies on 2-substituted-4H-3,1-benzoxazin-4-one showed good cytotoxic activity (Pavlidis & Perry, 1994) and herbicidal properties (Hamprecht et al., 2004). A variety of biological activities were associated with 2-Substituted-4H-3,1-benzoxazin-4-ones for example antifungal, antibacterial (Bouillant et al., 1983; Ponchet et al., 1984; Mayama et al., 1981; Hauteville et al., 1988; El-Din, 2000; Shalaby et al., 2000) and anti-elastase properties (Colson et al., 2005). They can be used for the treatment of obesity (Hodson et al., 2000) and also found to be novel specific puromycin-sensitive aminopeptidase inhibitors (Kakuta et al., 2001).

The 2-aryl-substituted-4H-3,1-benzoxazin-4-ones act as novel active substances for the cardiovascular system. They exhibit relaxing effect on smooth musculature in particular and markedly increase coronary flow through langendroff hearts (Ulrich, 1991). The promising therapeutic potential of this class of compounds prompted us to synthesize and biologically screen series of structural variants of 2-substituted-4H-3,1-benzoxazin-4-one. The title compound (I), is expected to possess some interesting biological activities; however present paper describes the X-ray diffraction studies that would be very help for us in molecular modeling and future drug design.

The title compound (I), was synthesized by employing (Fig. 3) Bain & Smalley methodology (Bain & Smalley, 1968); the reaction of p-nitroanthranilic acid with benzoylchloride in excess of pyridine gave title compound (I) in 90% yield.

All bond lengths in the title compound (I) show normal values (Allen et al., 1987). The title compound (I) is nearly planar with slight deviation [4.31 (13)°] of benzene ring from the mean plane of bezoxazine moiety. The one intramolecular C—H···O hydrogen bond generates the S(5) graph set motif, while one intermolecular C—H···O hydrogen bond keeps the molecules in parallel layers along ac plane in head to head fashion by two fold inversion axis (Bernstein et al., 1995). The additional ππ stacking interactions between adjacent molecules further stabilize the crystal structure along b axis. The centroid–centroid distances between the rings are Cg1–Cg3ii = 3.5757 (17) Å [symmetry code ii: 2 - x, -y, -z], where Cg1 and Cg3 are the centroids of the rings C1/O2/C2/N1/C8/C7 and C9/C10/C11/C12/C13/C14, respectively.

Related literature top

For related literature, see: Allen et al. (1987); Bain & Smalley (1968); Bernstein et al. (1995); Bouillant et al. (1983); Colson et al. (2005); El-Din (2000); Fenton et al. (1989); Francis et al. (2000); Gutschow et al. (1998); Hamprecht et al. (2004); Hauteville et al. (1988); Hodson et al. (2000); Johnson & Pattison (1986); Kakuta et al. (2001); Krantz et al. (1990); Mayama et al. (1981); Pavlidis & Perry (1994); Ponchet et al. (1984); Shalaby et al. (2000); Ulrich (1991); Uejima et al. (1993).

Experimental top

To a solution of p-nitroanthranilic acid (1.1 g, 6.04 mmol) in pyridine (25 ml) was added benzoylchloride (1.69 g, 12.08 mmol). The mixture was shaken for 5 min and placed at room temperature for a further 25 min., with occasional shaking. The reaction mixture was stirred into cold water (200 ml) and the precipitate was filtered off. The residue was washed free of pyridine with cold water (3x 60 ml) and dried. The title compound (I) was crystallized from ethanol in 90% yield (1.46 g).

Refinement top

All the rest of atoms were placed in calculated positions with a C—H distances in 0.93 Å and Uiso(H) values were constrained to be 1.5Ueq(C) of all the carrier atoms.

Structure description top

Recent work by the medicinal chemists had led to a number of drugs related uses being found for this class of heterocyclic compound. Fenton et al. have described plasma lipid altering characteristics of a series of 2-substituted-4H-3,1-benzoxazin-4-one as high density lipoprotein elevators for the treatment of patients suffering from hyperlipoproteinemia and associated diseases (Fenton et al., 1989). 2-Substituted-4H-3,1-benzoxazin-4-one base has been utilized as potent inhibitors of human leukocyte elastase (Krantz et al., 1990) and serine proteases (Gutschow et al., 1998). The National Cancer Institute, Washington, USA has also shown interest in 1-[3-(7-chloro-4-oxo-3,1-benzoxazin-4-yl) phenyl] methyl pyridinium chloride (NSC-341, 964) (Johnson & Pattison, 1986), evaluating its anti-neoplastic activity. Initial studies on 2-substituted-4H-3,1-benzoxazin-4-one showed good cytotoxic activity (Pavlidis & Perry, 1994) and herbicidal properties (Hamprecht et al., 2004). A variety of biological activities were associated with 2-Substituted-4H-3,1-benzoxazin-4-ones for example antifungal, antibacterial (Bouillant et al., 1983; Ponchet et al., 1984; Mayama et al., 1981; Hauteville et al., 1988; El-Din, 2000; Shalaby et al., 2000) and anti-elastase properties (Colson et al., 2005). They can be used for the treatment of obesity (Hodson et al., 2000) and also found to be novel specific puromycin-sensitive aminopeptidase inhibitors (Kakuta et al., 2001).

The 2-aryl-substituted-4H-3,1-benzoxazin-4-ones act as novel active substances for the cardiovascular system. They exhibit relaxing effect on smooth musculature in particular and markedly increase coronary flow through langendroff hearts (Ulrich, 1991). The promising therapeutic potential of this class of compounds prompted us to synthesize and biologically screen series of structural variants of 2-substituted-4H-3,1-benzoxazin-4-one. The title compound (I), is expected to possess some interesting biological activities; however present paper describes the X-ray diffraction studies that would be very help for us in molecular modeling and future drug design.

The title compound (I), was synthesized by employing (Fig. 3) Bain & Smalley methodology (Bain & Smalley, 1968); the reaction of p-nitroanthranilic acid with benzoylchloride in excess of pyridine gave title compound (I) in 90% yield.

All bond lengths in the title compound (I) show normal values (Allen et al., 1987). The title compound (I) is nearly planar with slight deviation [4.31 (13)°] of benzene ring from the mean plane of bezoxazine moiety. The one intramolecular C—H···O hydrogen bond generates the S(5) graph set motif, while one intermolecular C—H···O hydrogen bond keeps the molecules in parallel layers along ac plane in head to head fashion by two fold inversion axis (Bernstein et al., 1995). The additional ππ stacking interactions between adjacent molecules further stabilize the crystal structure along b axis. The centroid–centroid distances between the rings are Cg1–Cg3ii = 3.5757 (17) Å [symmetry code ii: 2 - x, -y, -z], where Cg1 and Cg3 are the centroids of the rings C1/O2/C2/N1/C8/C7 and C9/C10/C11/C12/C13/C14, respectively.

For related literature, see: Allen et al. (1987); Bain & Smalley (1968); Bernstein et al. (1995); Bouillant et al. (1983); Colson et al. (2005); El-Din (2000); Fenton et al. (1989); Francis et al. (2000); Gutschow et al. (1998); Hamprecht et al. (2004); Hauteville et al. (1988); Hodson et al. (2000); Johnson & Pattison (1986); Kakuta et al. (2001); Krantz et al. (1990); Mayama et al. (1981); Pavlidis & Perry (1994); Ponchet et al. (1984); Shalaby et al. (2000); Ulrich (1991); Uejima et al. (1993).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. A dashed line indicates the intramolecular hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of (I), viewed down the b axis.
[Figure 3] Fig. 3. The preparation of (I).
7-Nitro-2-phenyl-4H-3,1-benzoxazin-4-one top
Crystal data top
C14H8N2O4F(000) = 552
Mr = 268.22Dx = 1.470 Mg m3
Monoclinic, P21/cMelting point: 430 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.6403 (14) ÅCell parameters from 3298 reflections
b = 7.4693 (13) Åθ = 2.8–27.8°
c = 22.047 (4) ŵ = 0.11 mm1
β = 105.595 (6)°T = 293 K
V = 1211.9 (4) Å3Plate, yellow
Z = 40.45 × 0.42 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2109 independent reflections
Radiation source: fine-focus sealed tube1821 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.8°
ω scansh = 97
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.952, Tmax = 0.990l = 2624
5798 measured reflections
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0828P)2 + 0.9147P]
where P = (Fo2 + 2Fc2)/3
2109 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C14H8N2O4V = 1211.9 (4) Å3
Mr = 268.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.6403 (14) ŵ = 0.11 mm1
b = 7.4693 (13) ÅT = 293 K
c = 22.047 (4) Å0.45 × 0.42 × 0.09 mm
β = 105.595 (6)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2109 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1821 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.990Rint = 0.019
5798 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.171H-atom parameters constrained
S = 1.00Δρmax = 0.18 e Å3
2109 reflectionsΔρmin = 0.29 e Å3
181 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
O10.6749 (3)0.2424 (3)0.15791 (9)0.0724 (6)
O20.7645 (3)0.1864 (2)0.05594 (8)0.0574 (5)
O30.3710 (3)0.6371 (3)0.09118 (9)0.0771 (7)
O40.2699 (3)0.6007 (3)0.19100 (10)0.0854 (7)
N10.7048 (3)0.0810 (3)0.01017 (9)0.0538 (6)
N20.3523 (3)0.5488 (3)0.13872 (11)0.0608 (6)
C10.6737 (4)0.1380 (4)0.11668 (12)0.0546 (6)
C20.7748 (3)0.0731 (3)0.00586 (11)0.0482 (6)
C30.5316 (4)0.3121 (3)0.07507 (11)0.0520 (6)
H3A0.54500.38480.03990.062*
C40.4358 (3)0.3700 (3)0.13323 (11)0.0502 (6)
C50.4115 (3)0.2681 (4)0.18714 (11)0.0533 (6)
H5A0.34440.31140.22600.064*
C60.4892 (4)0.1012 (4)0.18178 (11)0.0551 (6)
H6A0.47600.03060.21750.066*
C70.5873 (3)0.0367 (3)0.12344 (11)0.0484 (6)
C80.6090 (3)0.1414 (3)0.06941 (11)0.0467 (6)
C90.8768 (3)0.1498 (3)0.05463 (12)0.0510 (6)
C100.9067 (3)0.0449 (4)0.10843 (12)0.0573 (7)
H10A0.86320.07190.10580.069*
C111.0012 (4)0.1145 (4)0.16582 (13)0.0664 (8)
H11A1.02040.04430.20190.080*
C121.0670 (4)0.2860 (5)0.17032 (15)0.0708 (9)
H12A1.13140.33130.20920.085*
C131.0377 (4)0.3911 (5)0.11741 (16)0.0761 (9)
H13A1.08200.50770.12060.091*
C140.9423 (4)0.3238 (4)0.05931 (14)0.0672 (8)
H14A0.92230.39520.02350.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0975 (16)0.0616 (12)0.0559 (11)0.0156 (11)0.0169 (10)0.0115 (10)
O20.0667 (11)0.0534 (10)0.0503 (10)0.0101 (8)0.0125 (8)0.0019 (8)
O30.1085 (17)0.0565 (12)0.0608 (12)0.0212 (11)0.0135 (11)0.0014 (10)
O40.1070 (17)0.0685 (13)0.0624 (13)0.0169 (12)0.0087 (12)0.0156 (11)
N10.0614 (13)0.0562 (13)0.0416 (11)0.0105 (10)0.0099 (9)0.0005 (9)
N20.0667 (14)0.0547 (13)0.0549 (13)0.0045 (11)0.0061 (11)0.0067 (11)
C10.0587 (15)0.0574 (15)0.0476 (14)0.0031 (12)0.0139 (11)0.0038 (12)
C20.0473 (13)0.0520 (14)0.0471 (13)0.0032 (11)0.0156 (10)0.0011 (11)
C30.0598 (15)0.0523 (14)0.0426 (13)0.0010 (12)0.0114 (11)0.0039 (11)
C40.0496 (13)0.0523 (14)0.0484 (13)0.0008 (11)0.0128 (11)0.0041 (11)
C50.0534 (14)0.0639 (16)0.0402 (13)0.0013 (12)0.0086 (10)0.0046 (11)
C60.0607 (15)0.0613 (16)0.0420 (13)0.0005 (12)0.0119 (11)0.0060 (11)
C70.0485 (13)0.0535 (14)0.0443 (13)0.0012 (11)0.0143 (10)0.0028 (10)
C80.0489 (13)0.0491 (13)0.0412 (12)0.0010 (10)0.0107 (10)0.0017 (10)
C90.0457 (13)0.0567 (15)0.0511 (14)0.0060 (11)0.0139 (11)0.0091 (11)
C100.0541 (14)0.0628 (16)0.0527 (14)0.0010 (12)0.0106 (12)0.0053 (12)
C110.0620 (17)0.077 (2)0.0539 (16)0.0014 (15)0.0058 (13)0.0085 (14)
C120.0580 (17)0.091 (2)0.0608 (18)0.0057 (15)0.0107 (13)0.0198 (16)
C130.0690 (19)0.0730 (19)0.088 (2)0.0243 (16)0.0233 (16)0.0246 (18)
C140.0728 (18)0.0660 (18)0.0656 (17)0.0172 (15)0.0236 (14)0.0066 (14)
Geometric parameters (Å, º) top
O1—C11.199 (3)C5—H5A0.9300
O2—C21.376 (3)C6—C71.389 (3)
O2—C11.380 (3)C6—H6A0.9300
O3—N21.214 (3)C7—C81.397 (3)
O4—N21.218 (3)C9—C141.386 (4)
N1—C21.262 (3)C9—C101.389 (4)
N1—C81.390 (3)C10—C111.379 (4)
N2—C41.471 (3)C10—H10A0.9300
C1—C71.452 (4)C11—C121.370 (5)
C2—C91.468 (3)C11—H11A0.9300
C3—C41.365 (3)C12—C131.374 (5)
C3—C81.397 (3)C12—H12A0.9300
C3—H3A0.9300C13—C141.387 (4)
C4—C51.381 (3)C13—H13A0.9300
C5—C61.372 (4)C14—H14A0.9300
C2—O2—C1121.5 (2)C6—C7—C1121.6 (2)
C2—N1—C8118.2 (2)C8—C7—C1118.0 (2)
O3—N2—O4123.7 (2)N1—C8—C3118.9 (2)
O3—N2—C4118.3 (2)N1—C8—C7122.1 (2)
O4—N2—C4118.0 (2)C3—C8—C7119.0 (2)
O1—C1—O2117.5 (2)C14—C9—C10119.5 (2)
O1—C1—C7127.0 (2)C14—C9—C2121.8 (2)
O2—C1—C7115.5 (2)C10—C9—C2118.7 (2)
N1—C2—O2124.7 (2)C11—C10—C9119.8 (3)
N1—C2—C9122.4 (2)C11—C10—H10A120.1
O2—C2—C9113.0 (2)C9—C10—H10A120.1
C4—C3—C8118.7 (2)C12—C11—C10120.7 (3)
C4—C3—H3A120.6C12—C11—H11A119.7
C8—C3—H3A120.6C10—C11—H11A119.7
C3—C4—C5123.2 (2)C11—C12—C13120.0 (3)
C3—C4—N2118.4 (2)C11—C12—H12A120.0
C5—C4—N2118.3 (2)C13—C12—H12A120.0
C6—C5—C4118.1 (2)C12—C13—C14120.2 (3)
C6—C5—H5A120.9C12—C13—H13A119.9
C4—C5—H5A120.9C14—C13—H13A119.9
C5—C6—C7120.5 (2)C9—C14—C13119.9 (3)
C5—C6—H6A119.7C9—C14—H14A120.1
C7—C6—H6A119.7C13—C14—H14A120.1
C6—C7—C8120.4 (2)
C2—O2—C1—O1178.1 (2)C2—N1—C8—C3179.6 (2)
C2—O2—C1—C71.5 (3)C2—N1—C8—C70.5 (4)
C8—N1—C2—O20.5 (4)C4—C3—C8—N1179.3 (2)
C8—N1—C2—C9179.3 (2)C4—C3—C8—C70.6 (4)
C1—O2—C2—N10.0 (4)C6—C7—C8—N1179.4 (2)
C1—O2—C2—C9179.9 (2)C1—C7—C8—N12.0 (4)
C8—C3—C4—C50.1 (4)C6—C7—C8—C30.5 (4)
C8—C3—C4—N2179.1 (2)C1—C7—C8—C3178.1 (2)
O3—N2—C4—C30.5 (4)N1—C2—C9—C14175.5 (3)
O4—N2—C4—C3178.7 (2)O2—C2—C9—C144.3 (4)
O3—N2—C4—C5178.7 (2)N1—C2—C9—C104.0 (4)
O4—N2—C4—C52.1 (4)O2—C2—C9—C10176.1 (2)
C3—C4—C5—C60.7 (4)C14—C9—C10—C110.1 (4)
N2—C4—C5—C6179.8 (2)C2—C9—C10—C11179.6 (2)
C4—C5—C6—C70.8 (4)C9—C10—C11—C120.4 (4)
C5—C6—C7—C80.3 (4)C10—C11—C12—C130.6 (5)
C5—C6—C7—C1178.8 (2)C11—C12—C13—C140.3 (5)
O1—C1—C7—C61.4 (4)C10—C9—C14—C130.4 (4)
O2—C1—C7—C6179.0 (2)C2—C9—C14—C13179.9 (3)
O1—C1—C7—C8177.2 (3)C12—C13—C14—C90.2 (5)
O2—C1—C7—C82.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O1i0.932.563.301 (3)137
C14—H14A···O20.932.412.738 (3)100
Symmetry code: (i) x+1, y1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC14H8N2O4
Mr268.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.6403 (14), 7.4693 (13), 22.047 (4)
β (°) 105.595 (6)
V3)1211.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.45 × 0.42 × 0.09
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.952, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
5798, 2109, 1821
Rint0.019
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.171, 1.00
No. of reflections2109
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.29

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O1i0.932.5563.301 (3)137
C14—H14A···O20.932.4122.738 (3)100
Symmetry code: (i) x+1, y1/2, z1/2.
 

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