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, C13H15N2+·C14H11O3, is a mol­ecular salt in which the conformation of the anion is stabilized by an intra­molecular O—H...O inter­action. The species are linked by an N—H...O bond and further hydrogen bonds lead to infinite one-dimensional chains along [010].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049331/hb2574sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049331/hb2574Isup2.hkl
Contains datablock I

CCDC reference: 667346

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.058
  • wR factor = 0.151
  • Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.62 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 5.56 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C2 .. 6.61 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT245_ALERT_2_C U(iso) H2A Smaller than U(eq) N2 by ... 0.01 AngSq PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ?
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 25.99 From the CIF: _reflns_number_total 2385 Count of symmetry unique reflns 2423 Completeness (_total/calc) 98.43% 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 ....... 67
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

This work continues our previous synthetic and structural studies of hydrogen bonding interactions between the 2-hydroxy-2,2-diphenylacetate anion and substituted pyridinium cations (Li, 2007).

The asymmetric unit of the title compound, (I), contains one 4,4'-methylene bis(benzenammonium) cation and one 2-hydroxy-2,2-diphenylacetate anion, in which these component ions are linked together through an N—H···O hydrogen bond (Table 1, Fig. 1). The dihedral angles between the aromatic ring planes in the cation and the anion are 83.87 (18)° and 75.48 (17)°, respectively. An intramolecular O–H···O hydrogen bond occurs within the benzylate anion and a S(5) ring (Bernstein et al., 1995) is generated. Moreover, adjacent ion pairs are further extended into an infinite one-dimensional chain along [010] by further intermolecular N—H···O hydrogen bonds (Fig. 2).

Related literature top

For related literature, see: Li (2007); Bernstein et al. (1995).

Experimental top

A 5-ml ethanol solution of 4,4'-methylene bis(benzenamine) (1.0 mmol, 0.20 g) added to a 20-ml hot aqueous solution of benzylic acid (1.0 mmol, 0.23 g) and the mixture was stirred for 15 minutes under the temperature of 373 K. Then the solution was filtered, and the filtrate was kept at the room temperature. After a week, colorless blades of (I) were obtained.

Refinement top

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. H atoms bonded to nitrogen atoms and hydroxyl group were located in a difference synthesis and refined isotropically with N—H = 0.90 (1) Å and O—H = 0.82 (1) Å, respectively. All the remaining H atoms were placed in calculated positions, with C—H = 0.93 and 0.97 Å for aromatic and methylene H atoms, respectively, and were refined as riding with Uiso = 1.2Ueq(C).

Structure description top

This work continues our previous synthetic and structural studies of hydrogen bonding interactions between the 2-hydroxy-2,2-diphenylacetate anion and substituted pyridinium cations (Li, 2007).

The asymmetric unit of the title compound, (I), contains one 4,4'-methylene bis(benzenammonium) cation and one 2-hydroxy-2,2-diphenylacetate anion, in which these component ions are linked together through an N—H···O hydrogen bond (Table 1, Fig. 1). The dihedral angles between the aromatic ring planes in the cation and the anion are 83.87 (18)° and 75.48 (17)°, respectively. An intramolecular O–H···O hydrogen bond occurs within the benzylate anion and a S(5) ring (Bernstein et al., 1995) is generated. Moreover, adjacent ion pairs are further extended into an infinite one-dimensional chain along [010] by further intermolecular N—H···O hydrogen bonds (Fig. 2).

For related literature, see: Li (2007); Bernstein et al. (1995).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. An infinite one dimensional hydrogen bonded chain along [010]. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.
4-(4-Aminobenzyl)anilinium 2-hydroxy-2,2-diphenylacetate top
Crystal data top
C13H15N2+·C14H11O3F(000) = 452
Mr = 426.50Dx = 1.250 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2500 reflections
a = 13.336 (6) Åθ = 2.3–28.2°
b = 6.477 (3) ŵ = 0.08 mm1
c = 14.454 (7) ÅT = 298 K
β = 114.777 (7)°Blade, colourless
V = 1133.6 (9) Å30.35 × 0.12 × 0.09 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer
2385 independent reflections
Radiation source: fine-focus sealed tube1701 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1614
Tmin = 0.972, Tmax = 0.993k = 76
5069 measured reflectionsl = 1217
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0779P)2 + 0.0728P]
where P = (Fo2 + 2Fc2)/3
2385 reflections(Δ/σ)max = 0.005
313 parametersΔρmax = 0.37 e Å3
67 restraintsΔρmin = 0.34 e Å3
Crystal data top
C13H15N2+·C14H11O3V = 1133.6 (9) Å3
Mr = 426.50Z = 2
Monoclinic, P21Mo Kα radiation
a = 13.336 (6) ŵ = 0.08 mm1
b = 6.477 (3) ÅT = 298 K
c = 14.454 (7) Å0.35 × 0.12 × 0.09 mm
β = 114.777 (7)°
Data collection top
Bruker SMART APEX CCD
diffractometer
2385 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
1701 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.993Rint = 0.034
5069 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05967 restraints
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.37 e Å3
2385 reflectionsΔρmin = 0.34 e Å3
313 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
N10.7443 (3)0.0297 (6)0.4427 (2)0.0852 (4)
H1A0.7667 (13)0.121 (3)0.4114 (13)0.0836 (5)*
H1B0.7345 (14)0.038 (3)0.4904 (11)0.0836 (5)*
N20.08804 (18)0.6545 (3)0.07426 (16)0.0424 (7)
H2A0.0770 (14)0.7807 (16)0.0951 (14)0.031 (7)*
H2B0.0346 (14)0.636 (5)0.0108 (9)0.067 (10)*
H2C0.0708 (13)0.558 (2)0.1107 (13)0.073 (11)*
O10.05811 (15)1.0586 (3)0.11769 (13)0.0446 (5)
O20.03234 (17)1.3555 (3)0.18013 (16)0.0609 (6)
O30.09565 (15)1.2283 (3)0.36568 (14)0.0504 (4)
H30.0516 (14)1.306 (2)0.3220 (13)0.0494 (5)*
C10.0580 (2)1.1684 (4)0.1886 (2)0.0372 (7)
C20.0943 (2)1.0716 (5)0.2953 (2)0.0456 (5)
C30.0175 (2)0.8989 (5)0.2980 (2)0.0427 (8)
C40.0720 (2)0.8274 (5)0.2139 (3)0.0551 (10)
H40.08880.88490.15010.066*
C50.1370 (3)0.6698 (6)0.2241 (3)0.0744 (12)
H50.19670.62080.16710.089*
C60.1138 (3)0.5862 (7)0.3177 (3)0.0817 (12)
H60.15770.48070.32410.098*
C70.0272 (3)0.6567 (6)0.4007 (3)0.0767 (11)
H70.01160.59950.46430.092*
C80.0380 (2)0.8128 (5)0.3916 (2)0.0557 (9)
H80.09690.86120.44960.067*
C90.2128 (2)0.9993 (5)0.32753 (19)0.0387 (8)
C100.2426 (2)0.7957 (5)0.3236 (2)0.0432 (8)
H100.18850.69380.30330.052*
C110.3508 (2)0.7417 (6)0.3492 (2)0.0549 (9)
H110.36940.60390.34730.066*
C120.4309 (3)0.8897 (6)0.3772 (2)0.0637 (11)
H120.50370.85380.39260.076*
C130.4033 (3)1.0900 (6)0.3823 (3)0.0747 (12)
H130.45791.19110.40220.090*
C140.2957 (3)1.1449 (6)0.3584 (3)0.0666 (11)
H140.27861.28260.36320.080*
C150.5325 (3)0.5414 (7)0.1174 (3)0.0720 (12)
H15A0.53310.48740.05500.086*
H15B0.57040.67330.13150.086*
C160.5942 (2)0.3939 (6)0.2040 (2)0.0518 (9)
C170.6351 (3)0.2125 (6)0.1885 (2)0.0648 (11)
H170.62730.17960.12320.078*
C180.6881 (3)0.0748 (6)0.2670 (3)0.0748 (12)
H180.71660.04740.25420.090*
C190.6987 (3)0.1173 (7)0.3634 (3)0.0815 (6)
C200.6607 (2)0.3063 (7)0.3806 (2)0.0693 (12)
H200.67080.34230.44620.083*
C210.6089 (3)0.4393 (6)0.3022 (3)0.0613 (11)
H210.58260.56400.31510.074*
C220.4140 (2)0.5740 (6)0.1020 (2)0.0548 (9)
C230.3468 (3)0.4093 (6)0.0959 (3)0.0828 (14)
H230.37430.27640.09840.099*
C240.2398 (3)0.4332 (5)0.0861 (3)0.0735 (14)
H240.19620.31880.08240.088*
C250.1999 (2)0.6279 (4)0.0821 (2)0.0410 (8)
C260.2638 (3)0.7928 (5)0.0868 (3)0.0631 (10)
H260.23590.92560.08340.076*
C270.3705 (3)0.7642 (6)0.0967 (3)0.0634 (10)
H270.41360.87920.09980.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0838 (5)0.0846 (5)0.0840 (5)0.0006 (5)0.0320 (5)0.0028 (5)
N20.0431 (12)0.0351 (12)0.0406 (12)0.0053 (11)0.0092 (10)0.0012 (11)
O10.0542 (10)0.0411 (11)0.0327 (9)0.0047 (10)0.0125 (8)0.0027 (9)
O20.0853 (13)0.0403 (12)0.0712 (11)0.0183 (11)0.0466 (10)0.0154 (10)
O30.0534 (5)0.0472 (5)0.0485 (5)0.0033 (5)0.0192 (5)0.0058 (5)
C10.0332 (13)0.0301 (14)0.0467 (14)0.0003 (12)0.0152 (11)0.0005 (12)
C20.0499 (7)0.0436 (8)0.0448 (7)0.0030 (7)0.0211 (7)0.0065 (7)
C30.0392 (13)0.0397 (16)0.0556 (15)0.0073 (12)0.0261 (11)0.0027 (13)
C40.0417 (15)0.055 (2)0.0672 (18)0.0041 (15)0.0218 (14)0.0059 (16)
C50.0455 (16)0.075 (3)0.105 (3)0.0162 (19)0.0339 (17)0.013 (2)
C60.0689 (18)0.065 (2)0.133 (3)0.0030 (19)0.0631 (17)0.013 (2)
C70.0730 (18)0.078 (2)0.101 (2)0.017 (2)0.0582 (16)0.037 (2)
C80.0512 (15)0.060 (2)0.0647 (17)0.0075 (16)0.0331 (13)0.0121 (16)
C90.0389 (14)0.0387 (15)0.0324 (13)0.0027 (12)0.0090 (11)0.0054 (12)
C100.0408 (14)0.0454 (18)0.0403 (13)0.0015 (14)0.0141 (11)0.0046 (13)
C110.0496 (16)0.0562 (19)0.0561 (16)0.0145 (16)0.0195 (13)0.0075 (17)
C120.0366 (16)0.080 (3)0.065 (2)0.0069 (18)0.0122 (15)0.0075 (19)
C130.0450 (17)0.071 (2)0.099 (3)0.0225 (18)0.0217 (17)0.021 (2)
C140.0548 (18)0.050 (2)0.090 (2)0.0086 (17)0.0255 (17)0.0165 (18)
C150.0590 (18)0.078 (2)0.079 (2)0.0088 (19)0.0286 (16)0.026 (2)
C160.0382 (14)0.069 (2)0.0492 (16)0.0012 (16)0.0192 (12)0.0042 (16)
C170.0620 (18)0.080 (3)0.0461 (16)0.0125 (19)0.0168 (15)0.0044 (18)
C180.069 (2)0.064 (2)0.083 (2)0.0182 (19)0.0236 (18)0.003 (2)
C190.0796 (8)0.0830 (8)0.0803 (8)0.0017 (8)0.0320 (8)0.0049 (8)
C200.0512 (18)0.109 (3)0.0409 (15)0.006 (2)0.0120 (14)0.0057 (18)
C210.0473 (16)0.073 (2)0.0655 (19)0.0008 (17)0.0260 (14)0.0143 (18)
C220.0481 (15)0.056 (2)0.0562 (17)0.0061 (16)0.0179 (13)0.0106 (17)
C230.058 (2)0.050 (2)0.128 (3)0.0112 (18)0.026 (2)0.008 (2)
C240.0470 (18)0.0326 (17)0.128 (3)0.0000 (15)0.024 (2)0.000 (2)
C250.0429 (14)0.0386 (16)0.0339 (13)0.0050 (13)0.0087 (12)0.0013 (12)
C260.0788 (19)0.0389 (18)0.088 (2)0.0061 (17)0.0508 (16)0.0031 (16)
C270.0634 (17)0.0506 (19)0.093 (2)0.0058 (17)0.0494 (15)0.0045 (18)
Geometric parameters (Å, º) top
N1—C191.416 (5)C11—H110.9300
N1—H1A0.872 (10)C12—C131.359 (6)
N1—H1B0.870 (10)C12—H120.9300
N2—C251.458 (4)C13—C141.375 (5)
N2—H2A0.904 (9)C13—H130.9300
N2—H2B0.903 (9)C14—H140.9300
N2—H2C0.905 (10)C15—C161.514 (5)
O1—C11.249 (3)C15—C221.515 (5)
O2—C11.251 (3)C15—H15A0.9700
O3—C21.432 (4)C15—H15B0.9700
O3—H30.827 (9)C16—C171.353 (5)
C1—C21.542 (4)C16—C211.381 (5)
C2—C91.522 (4)C17—C181.382 (5)
C2—C31.528 (4)C17—H170.9300
C3—C81.381 (4)C18—C191.368 (6)
C3—C41.379 (4)C18—H180.9300
C4—C51.387 (5)C19—C201.386 (6)
C4—H40.9300C20—C211.359 (5)
C5—C61.366 (6)C20—H200.9300
C5—H50.9300C21—H210.9300
C6—C71.349 (5)C22—C271.350 (5)
C6—H60.9300C22—C231.372 (5)
C7—C81.375 (5)C23—C241.382 (5)
C7—H70.9300C23—H230.9300
C8—H80.9300C24—C251.361 (4)
C9—C141.378 (4)C24—H240.9300
C9—C101.385 (4)C25—C261.350 (4)
C10—C111.376 (4)C26—C271.382 (5)
C10—H100.9300C26—H260.9300
C11—C121.364 (5)C27—H270.9300
C19—N1—H1A99.2 (14)C12—C13—C14120.7 (3)
C19—N1—H1B98.5 (15)C12—C13—H13119.6
H1A—N1—H1B161.9 (19)C14—C13—H13119.6
C25—N2—H2A112.6 (12)C9—C14—C13121.0 (3)
C25—N2—H2B114.1 (15)C9—C14—H14119.5
H2A—N2—H2B107 (2)C13—C14—H14119.5
C25—N2—H2C112.0 (12)C16—C15—C22112.4 (3)
H2A—N2—H2C108.2 (18)C16—C15—H15A109.1
H2B—N2—H2C102 (2)C22—C15—H15A109.1
C2—O3—H395.4 (14)C16—C15—H15B109.1
O2—C1—O1124.4 (3)C22—C15—H15B109.1
O2—C1—C2116.8 (3)H15A—C15—H15B107.9
O1—C1—C2118.8 (2)C17—C16—C21117.4 (3)
O3—C2—C9107.4 (2)C17—C16—C15121.9 (3)
O3—C2—C3108.0 (2)C21—C16—C15120.6 (3)
C9—C2—C3112.8 (2)C16—C17—C18121.9 (3)
O3—C2—C1109.1 (2)C16—C17—H17119.0
C9—C2—C1106.4 (2)C18—C17—H17119.0
C3—C2—C1113.0 (2)C19—C18—C17120.3 (4)
C8—C3—C4118.1 (3)C19—C18—H18119.8
C8—C3—C2117.4 (2)C17—C18—H18119.8
C4—C3—C2124.4 (3)C18—C19—C20118.0 (4)
C3—C4—C5120.1 (3)C18—C19—N1121.0 (4)
C3—C4—H4119.9C20—C19—N1120.9 (4)
C5—C4—H4119.9C21—C20—C19120.5 (3)
C6—C5—C4120.3 (3)C21—C20—H20119.8
C6—C5—H5119.8C19—C20—H20119.8
C4—C5—H5119.8C20—C21—C16121.7 (4)
C7—C6—C5120.0 (4)C20—C21—H21119.1
C7—C6—H6120.0C16—C21—H21119.1
C5—C6—H6120.0C27—C22—C23116.9 (3)
C6—C7—C8120.3 (4)C27—C22—C15122.2 (3)
C6—C7—H7119.9C23—C22—C15120.9 (3)
C8—C7—H7119.9C22—C23—C24122.5 (3)
C7—C8—C3121.1 (3)C22—C23—H23118.7
C7—C8—H8119.5C24—C23—H23118.7
C3—C8—H8119.5C25—C24—C23118.5 (3)
C14—C9—C10117.4 (3)C25—C24—H24120.7
C14—C9—C2118.5 (3)C23—C24—H24120.7
C10—C9—C2124.0 (3)C26—C25—C24120.2 (3)
C11—C10—C9121.2 (3)C26—C25—N2120.9 (3)
C11—C10—H10119.4C24—C25—N2118.9 (3)
C9—C10—H10119.4C25—C26—C27120.0 (3)
C12—C11—C10120.2 (3)C25—C26—H26120.0
C12—C11—H11119.9C27—C26—H26120.0
C10—C11—H11119.9C22—C27—C26121.8 (3)
C11—C12—C13119.4 (3)C22—C27—H27119.1
C11—C12—H12120.3C26—C27—H27119.1
C13—C12—H12120.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.83 (1)1.98 (2)2.586 (3)129 (2)
N2—H2C···O2i0.91 (1)1.85 (1)2.756 (3)178 (2)
N2—H2B···O1ii0.90 (1)1.82 (1)2.711 (3)170 (3)
N2—H2A···O10.90 (1)1.87 (1)2.759 (3)170 (2)
Symmetry codes: (i) x, y1, z; (ii) x, y1/2, z.

Experimental details

Crystal data
Chemical formulaC13H15N2+·C14H11O3
Mr426.50
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)13.336 (6), 6.477 (3), 14.454 (7)
β (°) 114.777 (7)
V3)1133.6 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.12 × 0.09
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.972, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
5069, 2385, 1701
Rint0.034
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.151, 1.06
No. of reflections2385
No. of parameters313
No. of restraints67
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.34

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.827 (9)1.984 (19)2.586 (3)129 (2)
N2—H2C···O2i0.905 (10)1.851 (11)2.756 (3)177.5 (18)
N2—H2B···O1ii0.903 (9)1.818 (11)2.711 (3)170 (3)
N2—H2A···O10.904 (9)1.865 (9)2.759 (3)169.6 (19)
Symmetry codes: (i) x, y1, z; (ii) x, y1/2, 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