Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C19H15FN2O3, was prepared by the reaction of (Z)-ethyl 3-amino-2-cyano-3-(4-fluoro­phen­yl)­acrylate and benzoyl chloride. In addition to an intra­molecular N—H...O hydrogen bond, the crystal packing shows the mol­ecules to be connected by inter­molecular C—H...O and C—H...N hydrogen bonds. The ethyl group is disordered over two positions, with site-occupancy factors of 0.75 and 0.25.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044145/im2031sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044145/im2031Isup2.hkl
Contains datablock I

CCDC reference: 663764

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.057
  • wR factor = 0.124
  • Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.38 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18' PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C16 ... 1.43 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 31 C7 -C15 -C16 -N2 94.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 32 C17 -C15 -C16 -N2 -80.00 7.00 1.555 1.555 1.555 1.555 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 10.00
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 2109 Count of symmetry unique reflns 2112 Completeness (_total/calc) 99.86% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound is useful as an inhibitor of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al. 2004; Creagh & Hubbell, 1992; Ibers & Hamilton, 1964). Recently, we obtained single crystals of this compound, and its crystal structure is reported here. The molecular conformation is stabilized by intramolecular C—H···O and N—H···O hydrogen bonds (Table 1). The crystal packing is governed by additional C—H···N and C—H···O interactions.

Related literature top

Several novel acrylate compounds are useful as inhibitors of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al., 2004; Creagh & Hubbell, 1992; Ibers & Hamilton, 1964).

Experimental top

To a solution of (Z)-ethyl 3-amino-2-cyano-3-(4-fluorophenyl)acrylate (1.17 g,0.0050 mol) in CH2Cl2 (18 ml), benzoyl chloride (2.11 g,0.015 mol) was added. Subsequently, Et3N (1.52 g,0.015 mol) was dropped into the solution under stirring. The reaction mixture was then heated to reflux and stirred for 4 h. Subsequently, it was cooled to room temperature, the reaction solution was filtered off and some white solid was separated. The organic phase was washed with water and then dried over Na2SO4. After removal of the solvent, a brown dope was obtained. After column chromatography using ethyl acetate/light petroleum (1:6) as the eluent, the pure E-isomer is separated from the mother liquid as colorless prismatic crystals. Small single crystals were grown from a solution of ethyl acetate/light petroleum (3:1) after 45 days, at room temperature.

Refinement top

The position of H1 was determined from the difference Fourier map and was refined without constraints. Methyl H atoms were placed in calculated positions with C—H=0.96 Å and the torsion angle was refined to fit the electron density; thermal parameters were refined as Uiso(H)=1.5Ueq(C). Other H atoms were placed in calculated positions with C—H = 0.96 Å (methylene) and 0.93 Å (aromatic C—H), and refined using a riding model, with Uiso(H)=1.2Ueq(C). In the absence of significant anomalous scattering, Friedel pairs were merged.

Structure description top

The title compound is useful as an inhibitor of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al. 2004; Creagh & Hubbell, 1992; Ibers & Hamilton, 1964). Recently, we obtained single crystals of this compound, and its crystal structure is reported here. The molecular conformation is stabilized by intramolecular C—H···O and N—H···O hydrogen bonds (Table 1). The crystal packing is governed by additional C—H···N and C—H···O interactions.

Several novel acrylate compounds are useful as inhibitors of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al., 2004; Creagh & Hubbell, 1992; Ibers & Hamilton, 1964).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% propability level and the atom-numbering scheme.
[Figure 2] Fig. 2. The packing of (I), viewed down the c axis showing one layer of molecules connected by intermolecular C(14)—H(14)···O(1) and C(5)—H(5)···N(2) hydrogen bonds.
(Z)-ethyl 3-(benzamido)-2-cyano-3-(4-fluorophenyl)acrylate top
Crystal data top
C19H15FN2O3F(000) = 704
Mr = 338.33Dx = 1.343 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2abCell parameters from 2229 reflections
a = 6.2149 (5) Åθ = 2.6–21.4°
b = 14.138 (1) ŵ = 0.10 mm1
c = 19.050 (1) ÅT = 292 K
V = 1673.8 (2) Å3Needle, colorless
Z = 40.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1634 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Graphite monochromatorθmax = 27.0°, θmin = 1.8°
phi and ω scansh = 77
15612 measured reflectionsk = 1418
2109 independent reflectionsl = 2424
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)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0453P)2 + 0.3759P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
2109 reflectionsΔρmax = 0.17 e Å3
250 parametersΔρmin = 0.17 e Å3
4 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (10)
Crystal data top
C19H15FN2O3V = 1673.8 (2) Å3
Mr = 338.33Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.2149 (5) ŵ = 0.10 mm1
b = 14.138 (1) ÅT = 292 K
c = 19.050 (1) Å0.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1634 reflections with I > 2σ(I)
15612 measured reflectionsRint = 0.052
2109 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124Δρmax = 0.17 e Å3
S = 1.11Δρmin = 0.17 e Å3
2109 reflectionsAbsolute structure: Flack (1983)
250 parametersAbsolute structure parameter: 0 (10)
4 restraints
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*/UeqOcc. (<1)
C10.5735 (7)0.8275 (3)0.24083 (18)0.0574 (10)
C20.7450 (7)0.8137 (2)0.19792 (18)0.0548 (9)
H20.85690.85740.19610.066*
C30.7488 (6)0.7328 (2)0.15683 (17)0.0480 (8)
H30.86500.72160.12720.058*
C40.5810 (5)0.6683 (2)0.15954 (14)0.0412 (7)
C50.4083 (6)0.6857 (3)0.20415 (17)0.0587 (10)
H50.29450.64310.20620.070*
C60.4053 (7)0.7653 (3)0.24518 (19)0.0664 (11)
H60.29090.77680.27550.080*
C70.5925 (6)0.5794 (2)0.11847 (15)0.0433 (8)
C80.2774 (6)0.6138 (3)0.04035 (17)0.0533 (9)
C90.1542 (6)0.5683 (3)0.01794 (16)0.0508 (9)
C100.2301 (8)0.4928 (3)0.05696 (19)0.0707 (11)
H100.36280.46590.04640.085*
C110.1081 (9)0.4574 (3)0.1117 (2)0.0879 (15)
H110.16090.40770.13870.106*
C120.0893 (9)0.4948 (4)0.1265 (2)0.0926 (18)
H120.17380.46910.16200.111*
C130.1612 (8)0.5702 (4)0.0887 (2)0.0806 (14)
H130.29380.59690.09970.097*
C140.0433 (6)0.6077 (3)0.03491 (19)0.0640 (11)
H140.09520.65940.00990.077*
C150.7524 (6)0.5153 (2)0.13150 (15)0.0459 (8)
C160.8881 (6)0.5289 (2)0.19117 (18)0.0472 (8)
C170.7806 (7)0.4278 (3)0.09120 (18)0.0570 (10)
C180.976 (2)0.2890 (7)0.0723 (5)0.072 (3)0.75 (2)
H18A1.00260.30040.02280.087*0.75 (2)
H18B0.84890.24990.07700.087*0.75 (2)
C191.1684 (18)0.2416 (9)0.1059 (6)0.087 (4)0.75 (2)
H19A1.29450.27950.09840.131*0.75 (2)
H19B1.18930.18030.08530.131*0.75 (2)
H19C1.14350.23480.15540.131*0.75 (2)
C18'1.081 (6)0.3096 (18)0.0732 (17)0.084 (10)0.25 (2)
H18C1.23060.32850.07350.101*0.25 (2)
H18D1.03320.30450.02480.101*0.25 (2)
C19'1.053 (9)0.214 (2)0.111 (2)0.131 (14)0.25 (2)
H19D1.11940.21750.15650.196*0.25 (2)
H19E1.12030.16520.08390.196*0.25 (2)
H19F0.90270.20050.11620.196*0.25 (2)
F10.5689 (5)0.90628 (18)0.28136 (12)0.0907 (9)
N10.4415 (5)0.5588 (2)0.06813 (15)0.0554 (8)
H10.471 (6)0.503 (3)0.0484 (19)0.066*
N20.9903 (6)0.5370 (2)0.24060 (17)0.0661 (9)
O10.2334 (5)0.69149 (19)0.06227 (14)0.0737 (8)
O20.6578 (5)0.39995 (18)0.04527 (14)0.0725 (8)
O30.9497 (5)0.3796 (2)0.11071 (14)0.0772 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.068 (3)0.051 (2)0.0531 (18)0.012 (2)0.000 (2)0.0122 (17)
C20.061 (2)0.0410 (19)0.062 (2)0.004 (2)0.004 (2)0.0069 (17)
C30.0492 (19)0.0437 (19)0.0510 (17)0.0010 (19)0.0071 (17)0.0026 (15)
C40.0406 (18)0.0435 (18)0.0396 (14)0.0007 (17)0.0026 (15)0.0003 (13)
C50.049 (2)0.067 (3)0.0600 (19)0.014 (2)0.0106 (18)0.0049 (19)
C60.054 (2)0.086 (3)0.059 (2)0.007 (3)0.017 (2)0.017 (2)
C70.0448 (18)0.0430 (18)0.0423 (15)0.0059 (17)0.0085 (15)0.0009 (14)
C80.056 (2)0.051 (2)0.0532 (18)0.004 (2)0.0010 (18)0.0007 (17)
C90.055 (2)0.054 (2)0.0434 (16)0.0096 (19)0.0018 (16)0.0066 (16)
C100.090 (3)0.060 (2)0.063 (2)0.003 (3)0.013 (2)0.0096 (19)
C110.121 (4)0.076 (3)0.067 (2)0.016 (3)0.027 (3)0.006 (2)
C120.104 (4)0.106 (4)0.068 (3)0.052 (4)0.037 (3)0.018 (3)
C130.063 (3)0.108 (4)0.071 (3)0.019 (3)0.018 (2)0.025 (3)
C140.059 (3)0.077 (3)0.0555 (19)0.009 (2)0.001 (2)0.014 (2)
C150.0551 (19)0.0372 (18)0.0452 (16)0.0031 (19)0.0041 (16)0.0007 (14)
C160.046 (2)0.0417 (19)0.0542 (18)0.0002 (17)0.0063 (17)0.0043 (16)
C170.078 (3)0.044 (2)0.0492 (18)0.002 (2)0.006 (2)0.0063 (17)
C180.086 (6)0.060 (5)0.071 (4)0.021 (5)0.019 (5)0.027 (3)
C190.113 (7)0.065 (6)0.083 (5)0.032 (5)0.023 (6)0.024 (5)
C18'0.065 (17)0.10 (2)0.086 (14)0.031 (17)0.020 (17)0.039 (16)
C19'0.13 (4)0.13 (3)0.13 (2)0.02 (3)0.00 (3)0.01 (2)
F10.104 (2)0.0759 (17)0.0920 (16)0.0136 (17)0.0071 (16)0.0396 (13)
N10.065 (2)0.0439 (17)0.0577 (16)0.0022 (17)0.0118 (16)0.0106 (14)
N20.062 (2)0.071 (2)0.0657 (18)0.001 (2)0.0089 (17)0.0033 (17)
O10.0789 (19)0.0590 (17)0.0833 (17)0.0130 (17)0.0195 (17)0.0171 (15)
O20.096 (2)0.0507 (16)0.0705 (16)0.0077 (16)0.0151 (17)0.0137 (13)
O30.098 (2)0.0618 (17)0.0722 (16)0.0301 (18)0.0121 (17)0.0125 (14)
Geometric parameters (Å, º) top
C1—F11.355 (4)C12—H120.9300
C1—C21.358 (5)C13—C141.367 (6)
C1—C61.369 (6)C13—H130.9300
C2—C31.387 (4)C14—H140.9300
C2—H20.9300C15—C161.428 (5)
C3—C41.386 (5)C15—C171.466 (5)
C3—H30.9300C16—N21.142 (4)
C4—C51.391 (5)C17—O21.226 (4)
C4—C71.483 (4)C17—O31.306 (5)
C5—C61.370 (5)C18—O31.486 (6)
C5—H50.9300C18—C191.511 (8)
C6—H60.9300C18—H18A0.9700
C7—C151.368 (5)C18—H18B0.9700
C7—N11.373 (4)C19—H19A0.9600
C8—O11.207 (4)C19—H19B0.9600
C8—N11.388 (5)C19—H19C0.9600
C8—C91.494 (5)C18'—O31.467 (10)
C9—C101.384 (5)C18'—C19'1.538 (11)
C9—C141.386 (5)C18'—H18C0.9700
C10—C111.384 (6)C18'—H18D0.9700
C10—H100.9300C19'—H19D0.9600
C11—C121.365 (7)C19'—H19E0.9600
C11—H110.9300C19'—H19F0.9600
C12—C131.362 (7)N1—H10.89 (4)
F1—C1—C2118.5 (4)C12—C13—C14121.6 (5)
F1—C1—C6118.5 (3)C12—C13—H13119.2
C2—C1—C6122.9 (3)C14—C13—H13119.2
C1—C2—C3118.2 (4)C13—C14—C9119.5 (4)
C1—C2—H2120.9C13—C14—H14120.2
C3—C2—H2120.9C9—C14—H14120.2
C4—C3—C2120.6 (3)C7—C15—C16118.9 (3)
C4—C3—H3119.7C7—C15—C17123.4 (3)
C2—C3—H3119.7C16—C15—C17117.4 (3)
C3—C4—C5119.2 (3)N2—C16—C15176.8 (4)
C3—C4—C7120.1 (3)O2—C17—O3122.5 (4)
C5—C4—C7120.6 (3)O2—C17—C15124.8 (4)
C6—C5—C4120.3 (4)O3—C17—C15112.7 (4)
C6—C5—H5119.9O3—C18—C19105.2 (7)
C4—C5—H5119.9O3—C18—H18A110.7
C1—C6—C5118.9 (3)C19—C18—H18A110.7
C1—C6—H6120.6O3—C18—H18B110.7
C5—C6—H6120.6C19—C18—H18B110.7
C15—C7—N1118.9 (3)H18A—C18—H18B108.8
C15—C7—C4120.1 (3)O3—C18'—C19'108 (3)
N1—C7—C4121.1 (3)O3—C18'—H18C110.2
O1—C8—N1123.0 (3)C19'—C18'—H18C110.2
O1—C8—C9122.2 (4)O3—C18'—H18D110.2
N1—C8—C9114.8 (3)C19'—C18'—H18D110.2
C10—C9—C14119.2 (4)H18C—C18'—H18D108.5
C10—C9—C8123.8 (4)C18'—C19'—H19D109.5
C14—C9—C8117.0 (4)C18'—C19'—H19E109.5
C11—C10—C9119.8 (4)H19D—C19'—H19E109.5
C11—C10—H10120.1C18'—C19'—H19F109.5
C9—C10—H10120.1H19D—C19'—H19F109.5
C12—C11—C10120.5 (5)H19E—C19'—H19F109.5
C12—C11—H11119.8C7—N1—C8130.5 (3)
C10—C11—H11119.8C7—N1—H1110 (2)
C13—C12—C11119.3 (4)C8—N1—H1119 (2)
C13—C12—H12120.3C17—O3—C18'131.2 (16)
C11—C12—H12120.3C17—O3—C18113.5 (4)
F1—C1—C2—C3179.7 (3)C10—C9—C14—C131.4 (5)
C6—C1—C2—C30.0 (6)C8—C9—C14—C13178.7 (3)
C1—C2—C3—C40.3 (5)N1—C7—C15—C16169.8 (3)
C2—C3—C4—C50.1 (5)C4—C7—C15—C168.7 (4)
C2—C3—C4—C7176.5 (3)N1—C7—C15—C174.2 (5)
C3—C4—C5—C60.4 (5)C4—C7—C15—C17177.2 (3)
C7—C4—C5—C6176.0 (3)C7—C15—C16—N294 (7)
F1—C1—C6—C5179.7 (4)C17—C15—C16—N280 (7)
C2—C1—C6—C50.5 (6)C7—C15—C17—O24.9 (6)
C4—C5—C6—C10.7 (6)C16—C15—C17—O2169.2 (3)
C3—C4—C7—C1561.6 (4)C7—C15—C17—O3176.9 (3)
C5—C4—C7—C15114.7 (4)C16—C15—C17—O38.9 (5)
C3—C4—C7—N1119.9 (4)C15—C7—N1—C8173.3 (3)
C5—C4—C7—N163.8 (4)C4—C7—N1—C88.2 (5)
O1—C8—C9—C10162.1 (4)O1—C8—N1—C75.7 (6)
N1—C8—C9—C1019.5 (5)C9—C8—N1—C7175.9 (3)
O1—C8—C9—C1415.1 (5)O2—C17—O3—C18'25.4 (19)
N1—C8—C9—C14163.3 (3)C15—C17—O3—C18'156.4 (19)
C14—C9—C10—C110.5 (6)O2—C17—O3—C180.3 (8)
C8—C9—C10—C11177.6 (4)C15—C17—O3—C18177.9 (7)
C9—C10—C11—C121.7 (7)C19'—C18'—O3—C17115 (4)
C10—C11—C12—C132.8 (7)C19'—C18'—O3—C1856 (4)
C11—C12—C13—C141.9 (7)C19—C18—O3—C17175.9 (11)
C12—C13—C14—C90.2 (6)C19—C18—O3—C18'48 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.89 (4)1.86 (4)2.653 (4)146 (3)
C14—H14···O1i0.932.563.202 (5)126
C5—H5···N2ii0.932.503.413 (5)167
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC19H15FN2O3
Mr338.33
Crystal system, space groupOrthorhombic, P212121
Temperature (K)292
a, b, c (Å)6.2149 (5), 14.138 (1), 19.050 (1)
V3)1673.8 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15612, 2109, 1634
Rint0.052
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.124, 1.11
No. of reflections2109
No. of parameters250
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.17
Absolute structureFlack (1983)
Absolute structure parameter0 (10)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.89 (4)1.86 (4)2.653 (4)146 (3)
C14—H14···O1i0.932.563.202 (5)126.1
C5—H5···N2ii0.932.503.413 (5)167.0
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds