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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2813
https://doi.org/10.1107/S1600536810040651

Benzoic acid–2-{(E)-[(E)-2-(2-pyridyl­methyl­­idene)hydrazin-1-yl­­idene]meth­yl}pyridine (2/1)

Hadi D. Arman,a Trupta Kaulguda and Edward R. T. Tiekinkb*

aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 9 October 2010; accepted 11 October 2010; online 20 October 2010)

The asymmetric unit of the title cocrystal, C12H10N4·2C7H6O2, comprises a single mol­ecule of benzoic acid and one half-mol­ecule of 2-pyridine­aldazine situated about a centre of inversion. The carboxyl group is coplanar with the benzene ring to which it is connected [O—C—C—C = −172.47 (12)°] and similarly, the 2-pyridine­aldazine mol­ecule is planar (r.m.s. deviation of the 16 non-H atoms = 0.017 Å). In the crystal, mol­ecules are connected into a non-planar three-mol­ecule aggregate [dihedral angle between the benzene and pyridyl ring connected by the hydrogen bond = 61.30 (7)°] with a twisted Z-shape. Layers of 2-pyridine­aldazine mol­ecules in the ab plane are sandwiched by benzoic acid mol­ecules being connected by O—H⋯N and C—H⋯O inter­actions, the latter involving the carbonyl O atom so that each benzoic acid mol­ecule links three different 2-pyridine­aldazine mol­ecules. Inter­digitated layers stack along the c axis.

Related literature

For related studies on co-crystal formation involving the isomeric n-pyridine­aldazines, see: Broker et al. (2008[Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879-887.]); Arman et al. (2010a[Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010a). Acta Cryst. E66, o2356.],b[Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010b). Acta Cryst. E66, o2629.]).

[Scheme 1]

Experimental

Crystal data

  • C12H10N4·2C7H6O2

  • Mr = 454.48

  • Triclinic, [P \overline 1]

  • a = 4.4509 (7) Å

  • b = 11.3635 (17) Å

  • c = 12.0612 (17) Å

  • α = 108.985 (6)°

  • β = 99.830 (9)°

  • γ = 97.849 (10)°

  • V = 556.16 (14) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 98 K

  • 0.40 × 0.29 × 0.12 mm
Data collection

  • Rigaku AFC12/SATURN724 diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.759, Tmax = 1.000

  • 2790 measured reflections

  • 1935 independent reflections

  • 1811 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.00

  • 1935 reflections

  • 158 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1o⋯N1 0.85 (2) 1.88 (2) 2.7269 (16) 177 (2)
C11—H11⋯O2i 0.95 2.54 3.1811 (19) 125
C12—H12⋯O2ii 0.95 2.59 3.4647 (19) 154
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y, z.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005[Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810040651/hg2725sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040651/hg2725Isup2.hkl

checkCIF report


Comment top

Co-crystallization experiments with the isomeric n-pyridinealdazines have led to the characterization of several co-crystals (Broker et al., 2008; Arman et al., 2010a; Arman et al., 2010b), and in continuation of these studies, the co-crystallization of benzoic acid and 2-pyridinealdazine was investigated. This lead to the isolation of the title 2/1 co-crystal, (I).

The asymmetric unit in (I) comprises a molecule of benzoic acid, Fig. 1, and half a molecule of 2-pyridinealdazine, with the latter disposed about a centre of inversion, Fig. 2. The constituents of (I) are connected by O—H···N hydrogen bonds, Table 1, to generate a centrosymmetric three molecule aggregate, Fig. 3. The benzoic acid molecule is planar as seen in the value of the O1—C1—C2—C3 torsion angle of -172.47 (12) °. Similarly, the 2-pyridinealdazine molecule is planar with the r.m.s. deviation of the 16 non-hydrogen atoms being 0.017 Å. However, the three molecule aggregate is not planar as the benzene ring forms a dihedral angle of 61.30 (7) ° with the pyridyl ring to which it is hydrogen bonded. Overall, when viewed normal to the plane through 2-pyridinealdazine, the aggregate has the shape of a twisted letter Z.

In the crystal packing, the 2-pyridinealdazine molecules pack in the ab plane with the benzoic acid molecules sandwiching these, Fig. 4. The connections are mediated by the aforementioned O—H···N hydrogen bond as well as C—H···O interactions formed by the carbonyl-O atom; each benzoic acid molecule links three distinct 2-pyridinealdazine molecules. Inter-digitated layers stack along the c axis.

Related literature top

For related studies on co-crystal formation involving the isomeric n-pyridinealdazines, see: Broker et al. (2008); Arman et al. (2010a,b).

Experimental top

Yellow crystals of (I) were isolated from the 2/1 co-crystallization of benzoic acid (Sigma Aldrich, 0.24 mmol) and 2-[(E)-[(E)-2-(pyridin-2-ylmethylidene)hydrazin-1-ylidene]methyl]pyridine (Sigma Aldrich, 0.12 mmol) in ethanol, m. pt. 351–353 K.

IR assignment (cm-1): 2600 (br) ν(O—H); 1691 ν(C=O); 1627 ν(C═N); 1469, 1451, 1416 ν(C–C(aromatic)); 1627 ν(C—N); 777 δ(C—H).

Refinement top

C-bound H-atoms were placed in calculated positions (C–H 0.95–0.99 Å) and were included in the refinement in the riding model approximation with Uiso(H) set to 1.2Ueq(C). The O-bound H-atom was located in a difference Fourier map and was refined with a distance restraint of O–H 0.84±0.01 Å, and with Uiso(H) = 1.5Ueq(O). In the final refinement a low angle reflection evidently effected by the beam stop was omitted, i.e. (0 1 1).

Structure description top

Co-crystallization experiments with the isomeric n-pyridinealdazines have led to the characterization of several co-crystals (Broker et al., 2008; Arman et al., 2010a; Arman et al., 2010b), and in continuation of these studies, the co-crystallization of benzoic acid and 2-pyridinealdazine was investigated. This lead to the isolation of the title 2/1 co-crystal, (I).

The asymmetric unit in (I) comprises a molecule of benzoic acid, Fig. 1, and half a molecule of 2-pyridinealdazine, with the latter disposed about a centre of inversion, Fig. 2. The constituents of (I) are connected by O—H···N hydrogen bonds, Table 1, to generate a centrosymmetric three molecule aggregate, Fig. 3. The benzoic acid molecule is planar as seen in the value of the O1—C1—C2—C3 torsion angle of -172.47 (12) °. Similarly, the 2-pyridinealdazine molecule is planar with the r.m.s. deviation of the 16 non-hydrogen atoms being 0.017 Å. However, the three molecule aggregate is not planar as the benzene ring forms a dihedral angle of 61.30 (7) ° with the pyridyl ring to which it is hydrogen bonded. Overall, when viewed normal to the plane through 2-pyridinealdazine, the aggregate has the shape of a twisted letter Z.

In the crystal packing, the 2-pyridinealdazine molecules pack in the ab plane with the benzoic acid molecules sandwiching these, Fig. 4. The connections are mediated by the aforementioned O—H···N hydrogen bond as well as C—H···O interactions formed by the carbonyl-O atom; each benzoic acid molecule links three distinct 2-pyridinealdazine molecules. Inter-digitated layers stack along the c axis.

For related studies on co-crystal formation involving the isomeric n-pyridinealdazines, see: Broker et al. (2008); Arman et al. (2010a,b).

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of benzoic acid found in the structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level
[Figure 2] Fig. 2. Molecular structure of 2-pyridinealdazine found in the structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. The molecule is disposed about a centre of inversion and i = 2 - x, 1 - y, 1 - z.
[Figure 3] Fig. 3. The three molecule aggregate in (I) highlighting the extended chair conformation. The O—H···N hydrogen bonds are shown as orange dashed lines.
[Figure 4] Fig. 4. A view of the supramolecular layer in (I) whereby 2-pyridinealdazine molecules are sandwiched by benzoic acid molecules. The O—H···N hydrogen bonds and C—H···O contacts are shown as orange and blue dashed lines, respectively.
[Figure 5] Fig. 5. A view in projection down the a axis showing the stacking of layers comprising three molecule aggregates along c. The O—H···N hydrogen bonds and C—H···O contacts are shown as orange and blue dashed lines, respectively.
Benzoic acid–2-{(E)-[(E)-2-(2-pyridylmethylidene)hydrazin-1- ylidene]methyl}pyridine (2/1) top
Crystal data top
C12H10N4·2C7H6O2Z = 1
Mr = 454.48F(000) = 238
Triclinic, P1Dx = 1.357 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.4509 (7) ÅCell parameters from 2619 reflections
b = 11.3635 (17) Åθ = 2.1–40.2°
c = 12.0612 (17) ŵ = 0.09 mm−1
α = 108.985 (6)°T = 98 K
β = 99.830 (9)°Block, yellow
γ = 97.849 (10)°0.40 × 0.29 × 0.12 mm
V = 556.16 (14) Å3
Data collection top
Rigaku AFC12K/SATURN724
diffractometer		1935 independent reflections
Radiation source: fine-focus sealed tube1811 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −5→4
Tmin = 0.759, Tmax = 1.000k = −13→13
2790 measured reflectionsl = −14→14
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0744P)2 + 0.1759P]
where P = (Fo2 + 2Fc2)/3
1935 reflections(Δ/σ)max < 0.001
158 parametersΔρmax = 0.20 e Å−3
1 restraintΔρmin = −0.23 e Å−3
Crystal data top
C12H10N4·2C7H6O2γ = 97.849 (10)°
Mr = 454.48V = 556.16 (14) Å3
Triclinic, P1Z = 1
a = 4.4509 (7) ÅMo Kα radiation
b = 11.3635 (17) ŵ = 0.09 mm−1
c = 12.0612 (17) ÅT = 98 K
α = 108.985 (6)°0.40 × 0.29 × 0.12 mm
β = 99.830 (9)°
Data collection top
Rigaku AFC12K/SATURN724
diffractometer		1935 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1811 reflections with I > 2σ(I)
Tmin = 0.759, Tmax = 1.000Rint = 0.022
2790 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0421 restraint
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.20 e Å−3
1935 reflectionsΔρmin = −0.23 e Å−3
158 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O10.6343 (3)0.67141 (10)0.18059 (9)0.0287 (3)
H1o0.584 (5)0.692 (2)0.2479 (12)0.050 (6)*
O20.7598 (3)0.88248 (10)0.23009 (9)0.0315 (3)
C10.7523 (3)0.77587 (13)0.16270 (12)0.0235 (3)
C20.8828 (3)0.74881 (14)0.05272 (12)0.0227 (3)
C31.0455 (3)0.85068 (14)0.03269 (13)0.0278 (4)
H31.07020.93490.08780.033*
C41.1716 (4)0.82926 (15)−0.06766 (14)0.0311 (4)
H41.28460.8987−0.08090.037*
C51.1331 (4)0.70640 (15)−0.14890 (13)0.0289 (4)
H51.21920.6919−0.21780.035*
C60.9695 (4)0.60477 (15)−0.12974 (13)0.0294 (4)
H60.94280.5208−0.18560.035*
C70.8444 (3)0.62603 (14)−0.02863 (13)0.0263 (3)
H70.73260.5564−0.01520.032*
N10.4834 (3)0.73022 (11)0.39929 (10)0.0214 (3)
N20.9261 (3)0.54922 (10)0.52702 (10)0.0211 (3)
C80.6169 (3)0.69350 (12)0.48783 (12)0.0190 (3)
C90.6033 (3)0.75148 (13)0.60760 (12)0.0219 (3)
H90.70020.72360.66830.026*
C100.4469 (3)0.85009 (13)0.63643 (12)0.0233 (3)
H100.43650.89180.71750.028*
C110.3052 (3)0.88738 (13)0.54546 (13)0.0231 (3)
H110.19320.95410.56270.028*
C120.3304 (3)0.82529 (13)0.42883 (13)0.0230 (3)
H120.23440.85150.36680.028*
C130.7833 (3)0.58938 (13)0.45006 (12)0.0209 (3)
H130.78460.55160.36740.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0405 (6)0.0251 (6)0.0230 (5)0.0084 (5)0.0124 (5)0.0085 (4)
O20.0457 (7)0.0254 (6)0.0247 (6)0.0126 (5)0.0110 (5)0.0070 (5)
C10.0261 (7)0.0244 (7)0.0208 (7)0.0084 (6)0.0028 (5)0.0093 (6)
C20.0231 (7)0.0261 (7)0.0200 (7)0.0083 (6)0.0018 (5)0.0098 (6)
C30.0333 (8)0.0248 (8)0.0231 (7)0.0064 (6)0.0035 (6)0.0070 (6)
C40.0336 (8)0.0315 (8)0.0299 (8)0.0025 (7)0.0065 (6)0.0151 (7)
C50.0302 (8)0.0372 (8)0.0238 (7)0.0118 (6)0.0087 (6)0.0135 (6)
C60.0349 (8)0.0277 (8)0.0262 (8)0.0103 (6)0.0091 (6)0.0075 (6)
C70.0314 (8)0.0236 (7)0.0259 (7)0.0084 (6)0.0081 (6)0.0098 (6)
N10.0212 (6)0.0202 (6)0.0235 (6)0.0037 (5)0.0055 (5)0.0088 (5)
N20.0200 (6)0.0203 (6)0.0242 (6)0.0063 (5)0.0077 (5)0.0073 (5)
C80.0165 (6)0.0182 (6)0.0232 (7)0.0018 (5)0.0060 (5)0.0087 (5)
C90.0205 (7)0.0234 (7)0.0231 (7)0.0037 (5)0.0059 (5)0.0100 (6)
C100.0251 (7)0.0223 (7)0.0230 (7)0.0036 (6)0.0100 (6)0.0069 (6)
C110.0214 (7)0.0183 (7)0.0312 (8)0.0052 (5)0.0092 (6)0.0091 (6)
C120.0220 (7)0.0217 (7)0.0272 (7)0.0050 (5)0.0040 (5)0.0117 (6)
C130.0194 (6)0.0204 (7)0.0237 (7)0.0036 (5)0.0076 (5)0.0078 (6)
Geometric parameters (Å, º) top
O1—C11.3292 (18)N1—C121.3381 (18)
O1—H1o0.846 (9)N1—C81.3449 (18)
O2—C11.2117 (17)N2—C131.2757 (18)
C1—C21.496 (2)N2—N2i1.408 (2)
C2—C71.388 (2)C8—C91.3949 (19)
C2—C31.391 (2)C8—C131.4698 (18)
C3—C41.384 (2)C9—C101.380 (2)
C3—H30.9500C9—H90.9500
C4—C51.388 (2)C10—C111.386 (2)
C4—H40.9500C10—H100.9500
C5—C61.385 (2)C11—C121.385 (2)
C5—H50.9500C11—H110.9500
C6—C71.390 (2)C12—H120.9500
C6—H60.9500C13—H130.9500
C7—H70.9500
C1—O1—H1o109.1 (15)C6—C7—H7120.0
O2—C1—O1123.44 (13)C12—N1—C8117.83 (12)
O2—C1—C2123.29 (14)C13—N2—N2i111.87 (13)
O1—C1—C2113.26 (12)N1—C8—C9122.45 (12)
C7—C2—C3119.91 (13)N1—C8—C13115.34 (12)
C7—C2—C1121.78 (14)C9—C8—C13122.20 (12)
C3—C2—C1118.31 (13)C10—C9—C8118.85 (13)
C4—C3—C2119.96 (14)C10—C9—H9120.6
C4—C3—H3120.0C8—C9—H9120.6
C2—C3—H3120.0C9—C10—C11119.04 (12)
C3—C4—C5120.05 (14)C9—C10—H10120.5
C3—C4—H4120.0C11—C10—H10120.5
C5—C4—H4120.0C10—C11—C12118.57 (12)
C6—C5—C4120.19 (14)C10—C11—H11120.7
C6—C5—H5119.9C12—C11—H11120.7
C4—C5—H5119.9N1—C12—C11123.25 (13)
C5—C6—C7119.84 (14)N1—C12—H12118.4
C5—C6—H6120.1C11—C12—H12118.4
C7—C6—H6120.1N2—C13—C8120.75 (12)
C2—C7—C6120.06 (14)N2—C13—H13119.6
C2—C7—H7120.0C8—C13—H13119.6
O2—C1—C2—C7−173.81 (14)C12—N1—C8—C9−0.65 (19)
O1—C1—C2—C77.72 (19)C12—N1—C8—C13−179.57 (11)
O2—C1—C2—C36.0 (2)N1—C8—C9—C100.1 (2)
O1—C1—C2—C3−172.47 (12)C13—C8—C9—C10178.93 (12)
C7—C2—C3—C4−0.7 (2)C8—C9—C10—C110.8 (2)
C1—C2—C3—C4179.52 (13)C9—C10—C11—C12−1.0 (2)
C2—C3—C4—C50.6 (2)C8—N1—C12—C110.4 (2)
C3—C4—C5—C6−0.2 (2)C10—C11—C12—N10.5 (2)
C4—C5—C6—C7−0.2 (2)N2i—N2—C13—C8−179.13 (12)
C3—C2—C7—C60.3 (2)N1—C8—C13—N2178.03 (12)
C1—C2—C7—C6−179.93 (13)C9—C8—C13—N2−0.9 (2)
C5—C6—C7—C20.2 (2)
Symmetry code: (i) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N10.85 (2)1.88 (2)2.7269 (16)177 (2)
C11—H11···O2ii0.952.543.1811 (19)125
C12—H12···O2iii0.952.593.4647 (19)154
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC12H10N4·2C7H6O2
Mr454.48
Crystal system, space groupTriclinic, P1
Temperature (K)98
a, b, c (Å)4.4509 (7), 11.3635 (17), 12.0612 (17)
α, β, γ (°)108.985 (6), 99.830 (9), 97.849 (10)
V (Å3)556.16 (14)
Z1
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.40 × 0.29 × 0.12
Data collection
DiffractometerRigaku AFC12K/SATURN724
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.759, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		2790, 1935, 1811
Rint0.022
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.00
No. of reflections1935
No. of parameters158
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.23

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N10.847 (16)1.881 (16)2.7269 (16)177 (2)
C11—H11···O2i0.952.543.1811 (19)125
C12—H12···O2ii0.952.593.4647 (19)154
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z.
 

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2813
https://doi.org/10.1107/S1600536810040651
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