PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1399–m1400.
Published online 2009 October 23. doi:  10.1107/S160053680904241X
PMCID: PMC2971359

catena-Poly[[(4-formyl­benzoato-κO 1)(isonicotinamide-κN 1)zinc(II)]-μ-4-formyl­benzoato-κ2 O 1:O 1′]

Abstract

In the title compound, [Zn(C8H5O3)2(C6H6N2O)]n, the ZnII ion is tetrahedrally coordinated by two formyl­benzoate (FB) and one isonicotinamide (INA) ligands while symmetry-related FB ligands bridge adjacent ZnII ions, forming polymeric chains along the b axis. The carboxyl­ate groups in the two FB ions are twisted away from the attached benzene ring by 9.07 (2) and 26.2 (2)°. The two benzene rings of the FB ions are oriented at a dihedral angle of 81.30 (5)°. In the crystal, adjacent polymeric chains inter­act via N—H(...)O and C—H(...)O hydrogen bonds, π–π contacts between the formyl­benzoate rings [centroid–centroid distance = 3.7736 (8) Å] and weak C—H(...)π inter­actions, forming a three-dimensional network.

Related literature

For general background to niacin, see: Krishnamachari (1974 [triangle]). For the crystal structure of N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 [triangle]). For related structures, see: Hökelek & Necefoğlu (1996 [triangle]); Hökelek et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1399-scheme1.jpg

Experimental

Crystal data

  • [Zn(C8H5O3)2(C6H6N2O)]
  • M r = 485.74
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1399-efi1.jpg
  • a = 13.3143 (2) Å
  • b = 6.7857 (1) Å
  • c = 21.3927 (3) Å
  • β = 91.458 (1)°
  • V = 1932.14 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.32 mm−1
  • T = 100 K
  • 0.22 × 0.12 × 0.08 mm

Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.829, T max = 0.903
  • 17841 measured reflections
  • 4812 independent reflections
  • 4086 reflections with I > 2σ(I)
  • R int = 0.072

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.080
  • S = 1.10
  • 4812 reflections
  • 297 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904241X/ci2939sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904241X/ci2939Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2009-FEF-03).

supplementary crystallographic information

Comment

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

In the crystal structure of the title compound, each ZnII ion is coordinated by two formylbenzoate (FB) and one isonicotinamide (INA) ligands (Fig. 1), while symmetry related FB ligands bridge the ZnII ions forming polymeric chains along the b axis (Fig.2). The structures of similar complexes of ZnII ion, [Zn2(C10H14N2O)2(C7H5O3)4].2H2O (Hökelek & Necefouglu, 1996) and [Zn(C9H10NO2)2(C6H6N2O)(H2O)2] (Hökelek et al., 2009) have also been reported.

The average Zn—O bond length (Table 1) is 1.9442 (11) Å and the Zn1 atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O3/C8/O4*) by 0.687 (5) Å and 0.703 (2) Å, respectively. The O1/C1/O2 and O3/C8/O4* carboxylate planes form dihedral angles of 9.07 (2)° and 26.2 (2)°, respectively, with benzene rings A(C2-C7) and B(C9-C14), while the angles between rings A, B and C (N1/C15-C19) are A/B = 81.30 (5), A/C = 63.17 (5) and B/C = 46.11 (5)°.

In the crystal structure, N—H···O and C—H···O hydrogen bonds (Table 2) link adjacent chains into a three-dimensional network. In addition, π–π contacts between symmetry related A(C2-C7) formylbenzoate rings at (x, y, z) and (5/2-x, -1/2+y, 1/2-z)/(5/2-x, 1/2+y, 1/2-z) with a centroid-to-centroid distance of 3.7736 (8) Å, and weak C—H···π interaction (Table 2) involving the B(C9-C14) ring stabilize the structure.

Experimental

The title compound was prepared by the reaction of ZnSO4.H2O (0.90 g, 5 mmol) in H2O (25 ml) and INA (1.22 g, 10 mmol) in H2O (40 ml) with sodium 4-formylbenzoate (1.72 g, 10 mmol) in H2O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving colourless single crystals.

Refinement

Atoms H21 and H22 (for methine) were located in a difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically with N-H = 0.86 Å (for NH2) and C-H = 0.93 Å for aromatic H atoms and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Part of a polymeric chain of the title compound.

Crystal data

[Zn(C8H5O3)2(C6H6N2O)]F(000) = 992
Mr = 485.74Dx = 1.670 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9448 reflections
a = 13.3143 (2) Åθ = 3.1–28.4°
b = 6.7857 (1) ŵ = 1.32 mm1
c = 21.3927 (3) ÅT = 100 K
β = 91.458 (1)°Needle, colourless
V = 1932.14 (5) Å30.22 × 0.12 × 0.08 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer4812 independent reflections
Radiation source: fine-focus sealed tube4086 reflections with I > 2σ(I)
graphiteRint = 0.072
[var phi] and ω scansθmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −17→14
Tmin = 0.829, Tmax = 0.903k = −8→9
17841 measured reflectionsl = −28→28

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.10w = 1/[σ2(Fo2) + (0.0394P)2 + 0.0092P] where P = (Fo2 + 2Fc2)/3
4812 reflections(Δ/σ)max = 0.001
297 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = −0.39 e Å3

Special details

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)

xyzUiso*/Ueq
Zn10.816160 (13)0.51300 (2)0.187880 (8)0.01058 (7)
O10.95052 (8)0.60767 (16)0.20123 (5)0.0149 (2)
O21.00643 (8)0.55706 (16)0.10502 (5)0.0149 (2)
O30.77863 (8)0.37932 (15)0.26575 (5)0.0134 (2)
O40.70741 (8)0.67550 (14)0.15404 (5)0.0137 (2)
O50.83582 (11)−0.07543 (19)−0.07713 (6)0.0312 (3)
O61.49773 (9)0.61367 (17)0.23858 (5)0.0199 (3)
O71.10801 (11)0.97953 (16)0.45862 (6)0.0236 (3)
N10.81632 (9)0.29546 (17)0.12295 (6)0.0112 (3)
N20.91501 (11)−0.28715 (18)−0.01158 (6)0.0182 (3)
H2A0.9269−0.3695−0.04100.022*
H2B0.9348−0.31250.02620.022*
C11.02044 (11)0.5821 (2)0.16202 (7)0.0110 (3)
C21.12564 (11)0.5862 (2)0.18971 (7)0.0109 (3)
C31.14051 (12)0.5879 (2)0.25423 (7)0.0126 (3)
H31.08570.58670.28030.015*
C41.23802 (12)0.5913 (2)0.27978 (7)0.0131 (3)
H41.24870.59060.32290.016*
C51.31866 (11)0.5957 (2)0.24033 (7)0.0122 (3)
C61.30379 (12)0.5942 (2)0.17551 (7)0.0143 (3)
H61.35850.59790.14940.017*
C71.20746 (12)0.5872 (2)0.15043 (7)0.0134 (3)
H71.19710.58320.10730.016*
C80.81930 (11)0.3293 (2)0.31722 (7)0.0115 (3)
C90.89783 (12)0.4527 (2)0.34954 (7)0.0114 (3)
C100.96360 (12)0.3649 (2)0.39317 (7)0.0149 (3)
H100.96030.22990.40040.018*
C111.03354 (13)0.4785 (2)0.42548 (8)0.0162 (3)
H111.07920.41880.45310.019*
C121.03609 (12)0.6823 (2)0.41700 (7)0.0140 (3)
C130.97104 (12)0.7698 (2)0.37288 (7)0.0138 (3)
H130.97300.90530.36660.017*
C140.90409 (12)0.6556 (2)0.33872 (7)0.0122 (3)
H140.86270.71380.30830.015*
C150.86757 (11)0.1289 (2)0.13520 (7)0.0125 (3)
H150.89240.10740.17570.015*
C160.88489 (13)−0.0119 (2)0.09003 (8)0.0139 (3)
H160.9213−0.12510.10000.017*
C170.84719 (12)0.0179 (2)0.02948 (8)0.0126 (3)
C180.79165 (12)0.1872 (2)0.01756 (7)0.0147 (3)
H180.76390.2097−0.02210.018*
C190.77770 (12)0.3220 (2)0.06473 (7)0.0136 (3)
H190.74040.43500.05610.016*
C200.86597 (12)−0.1204 (2)−0.02441 (7)0.0157 (3)
C211.42128 (13)0.6036 (2)0.26818 (8)0.0161 (3)
H211.4266 (13)0.600 (3)0.3157 (9)0.028 (5)*
C221.10601 (13)0.8010 (2)0.45686 (8)0.0188 (4)
H221.1561 (13)0.714 (3)0.4842 (9)0.020 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.01001 (11)0.01290 (10)0.00882 (11)0.00080 (6)−0.00023 (7)−0.00111 (6)
O10.0092 (6)0.0225 (6)0.0129 (5)−0.0007 (4)0.0003 (4)−0.0045 (4)
O20.0144 (6)0.0195 (5)0.0106 (5)0.0021 (5)−0.0019 (5)−0.0020 (4)
O30.0120 (6)0.0184 (5)0.0098 (5)−0.0013 (4)−0.0021 (4)0.0016 (4)
O40.0134 (6)0.0141 (5)0.0135 (5)0.0030 (4)−0.0013 (5)−0.0022 (4)
O50.0524 (9)0.0310 (7)0.0097 (6)0.0163 (7)−0.0092 (6)−0.0050 (5)
O60.0130 (6)0.0295 (6)0.0172 (6)−0.0013 (5)−0.0005 (5)0.0005 (5)
O70.0279 (8)0.0248 (6)0.0181 (7)−0.0107 (5)0.0007 (6)−0.0038 (5)
N10.0094 (7)0.0145 (6)0.0096 (6)−0.0011 (5)−0.0002 (5)0.0003 (5)
N20.0256 (8)0.0193 (6)0.0094 (6)0.0055 (6)−0.0018 (6)−0.0037 (5)
C10.0111 (8)0.0103 (6)0.0115 (7)0.0008 (6)−0.0008 (6)−0.0005 (6)
C20.0111 (8)0.0102 (6)0.0113 (7)0.0000 (6)−0.0016 (6)0.0001 (6)
C30.0128 (8)0.0145 (7)0.0106 (7)0.0009 (6)0.0017 (6)0.0001 (6)
C40.0164 (8)0.0143 (7)0.0085 (7)0.0000 (6)−0.0008 (6)−0.0002 (6)
C50.0121 (8)0.0110 (7)0.0135 (8)0.0003 (6)−0.0016 (6)0.0002 (6)
C60.0113 (8)0.0190 (7)0.0127 (7)−0.0008 (6)0.0028 (6)−0.0003 (6)
C70.0143 (8)0.0183 (7)0.0076 (7)0.0006 (6)−0.0008 (6)0.0006 (6)
C80.0096 (8)0.0138 (7)0.0113 (7)0.0029 (6)0.0015 (6)−0.0023 (6)
C90.0098 (8)0.0154 (7)0.0091 (7)−0.0002 (6)0.0015 (6)−0.0020 (6)
C100.0173 (9)0.0137 (7)0.0137 (8)0.0002 (6)−0.0001 (7)−0.0003 (6)
C110.0144 (9)0.0206 (8)0.0134 (8)0.0021 (6)−0.0043 (7)−0.0003 (6)
C120.0113 (8)0.0191 (7)0.0117 (7)−0.0021 (6)−0.0004 (6)−0.0029 (6)
C130.0149 (8)0.0136 (7)0.0129 (7)−0.0015 (6)0.0041 (6)−0.0024 (6)
C140.0111 (8)0.0164 (7)0.0090 (7)0.0020 (6)0.0012 (6)0.0004 (6)
C150.0116 (8)0.0171 (7)0.0087 (7)0.0004 (6)−0.0023 (6)0.0008 (6)
C160.0157 (9)0.0140 (7)0.0120 (8)0.0026 (6)−0.0017 (7)−0.0003 (5)
C170.0147 (8)0.0143 (7)0.0088 (8)−0.0022 (6)0.0006 (6)−0.0003 (5)
C180.0169 (9)0.0176 (7)0.0094 (7)−0.0006 (6)−0.0029 (6)0.0014 (6)
C190.0130 (8)0.0150 (7)0.0128 (7)0.0019 (6)−0.0011 (6)0.0029 (6)
C200.0180 (9)0.0185 (7)0.0106 (7)0.0001 (6)−0.0013 (7)−0.0024 (6)
C210.0173 (9)0.0171 (7)0.0139 (8)0.0003 (6)−0.0024 (7)−0.0003 (6)
C220.0174 (9)0.0260 (8)0.0131 (8)−0.0046 (7)0.0007 (7)−0.0018 (7)

Geometric parameters (Å, °)

Zn1—O11.9153 (11)C7—C61.378 (2)
Zn1—O31.9723 (11)C7—H70.93
Zn1—O41.9450 (10)C8—O4ii1.2669 (18)
Zn1—N12.0270 (12)C8—C91.495 (2)
O1—C11.2807 (18)C9—C101.397 (2)
O2—C11.2405 (18)C9—C141.3990 (19)
O3—C81.2611 (17)C10—H100.93
O4—C8i1.2669 (18)C11—C101.381 (2)
O5—C201.2261 (18)C11—H110.93
O6—C211.214 (2)C12—C111.395 (2)
O7—C221.2124 (19)C12—C131.397 (2)
N1—C151.3427 (18)C12—C221.484 (2)
N1—C191.3474 (18)C13—C141.377 (2)
N2—C201.332 (2)C13—H130.93
N2—H2A0.86C14—H140.93
N2—H2B0.86C15—H150.93
C2—C11.507 (2)C16—C151.382 (2)
C2—C31.390 (2)C16—C171.392 (2)
C2—C71.393 (2)C16—H160.93
C3—C41.396 (2)C18—C171.386 (2)
C3—H30.93C18—H180.93
C4—H40.93C19—C181.378 (2)
C5—C41.383 (2)C19—H190.93
C5—C61.396 (2)C20—C171.512 (2)
C5—C211.478 (2)C21—H211.018 (19)
C6—H60.93C22—H221.057 (17)
O1—Zn1—O3106.50 (4)C14—C9—C8121.23 (13)
O1—Zn1—O4123.30 (5)C9—C10—H10120.0
O1—Zn1—N1109.22 (5)C11—C10—C9119.95 (14)
O3—Zn1—N1104.39 (5)C11—C10—H10120.0
O4—Zn1—O3111.89 (5)C10—C11—C12120.45 (15)
O4—Zn1—N199.88 (5)C10—C11—H11119.8
C1—O1—Zn1123.27 (10)C12—C11—H11119.8
C8—O3—Zn1138.48 (10)C11—C12—C13119.50 (14)
C8i—O4—Zn1120.13 (10)C11—C12—C22118.70 (15)
C15—N1—Zn1119.26 (10)C13—C12—C22121.77 (14)
C15—N1—C19118.22 (13)C12—C13—H13120.0
C19—N1—Zn1121.95 (10)C14—C13—C12120.09 (14)
C20—N2—H2A120.0C14—C13—H13120.0
C20—N2—H2B120.0C9—C14—H14119.8
H2A—N2—H2B120.0C13—C14—C9120.42 (14)
O1—C1—C2115.07 (13)C13—C14—H14119.8
O2—C1—O1124.67 (14)N1—C15—C16122.57 (14)
O2—C1—C2120.25 (14)N1—C15—H15118.7
C3—C2—C1119.87 (14)C16—C15—H15118.7
C3—C2—C7120.36 (14)C15—C16—C17119.19 (14)
C7—C2—C1119.76 (13)C15—C16—H16120.4
C2—C3—C4119.77 (14)C17—C16—H16120.4
C2—C3—H3120.1C16—C17—C20123.82 (13)
C4—C3—H3120.1C18—C17—C16118.00 (14)
C3—C4—H4120.3C18—C17—C20118.16 (14)
C5—C4—C3119.36 (14)C17—C18—H18120.1
C5—C4—H4120.3C19—C18—C17119.77 (14)
C4—C5—C6120.90 (14)C19—C18—H18120.1
C4—C5—C21118.62 (14)N1—C19—C18122.20 (14)
C6—C5—C21120.48 (14)N1—C19—H19118.9
C5—C6—H6120.2C18—C19—H19118.9
C7—C6—C5119.60 (14)O5—C20—N2123.26 (15)
C7—C6—H6120.2O5—C20—C17119.35 (14)
C2—C7—H7120.0N2—C20—C17117.39 (13)
C6—C7—C2119.98 (14)O6—C21—C5124.78 (15)
C6—C7—H7120.0O6—C21—H21119.0 (11)
O3—C8—O4ii121.72 (14)C5—C21—H21116.3 (11)
O3—C8—C9122.19 (13)O7—C22—C12124.98 (17)
O4ii—C8—C9116.01 (13)O7—C22—H22121.9 (9)
C10—C9—C8119.27 (13)C12—C22—H22113.1 (9)
C10—C9—C14119.45 (14)
O3—Zn1—O1—C1132.27 (11)C21—C5—C4—C3178.69 (13)
O4—Zn1—O1—C1−96.44 (12)C4—C5—C6—C7−0.3 (2)
N1—Zn1—O1—C120.07 (13)C21—C5—C6—C7−179.85 (14)
O1—Zn1—O3—C8−6.56 (15)C4—C5—C21—O6−177.81 (15)
O4—Zn1—O3—C8−143.97 (14)C6—C5—C21—O61.7 (2)
N1—Zn1—O3—C8108.94 (15)C2—C7—C6—C51.5 (2)
O1—Zn1—O4—C8i−60.90 (13)O3—C8—C9—C10−158.23 (15)
O3—Zn1—O4—C8i68.17 (12)O3—C8—C9—C1424.3 (2)
N1—Zn1—O4—C8i178.16 (11)O4ii—C8—C9—C1024.8 (2)
O1—Zn1—N1—C1562.86 (12)O4ii—C8—C9—C14−152.61 (15)
O1—Zn1—N1—C19−108.32 (12)C8—C9—C10—C11−177.06 (15)
O3—Zn1—N1—C15−50.72 (12)C14—C9—C10—C110.4 (2)
O3—Zn1—N1—C19138.10 (12)C8—C9—C14—C13174.28 (14)
O4—Zn1—N1—C15−166.53 (11)C10—C9—C14—C13−3.2 (2)
O4—Zn1—N1—C1922.29 (13)C12—C11—C10—C92.9 (3)
Zn1—O1—C1—O225.4 (2)C13—C12—C11—C10−3.6 (3)
Zn1—O1—C1—C2−155.21 (9)C22—C12—C11—C10174.41 (16)
Zn1—O3—C8—O4ii−147.48 (12)C11—C12—C13—C140.9 (2)
Zn1—O3—C8—C935.8 (2)C22—C12—C13—C14−177.08 (15)
Zn1—N1—C15—C16−169.24 (12)C11—C12—C22—O7−171.97 (17)
C19—N1—C15—C162.3 (2)C13—C12—C22—O76.0 (3)
Zn1—N1—C19—C18169.38 (12)C12—C13—C14—C92.5 (2)
C15—N1—C19—C18−1.9 (2)C17—C16—C15—N1−0.7 (2)
C3—C2—C1—O19.2 (2)C15—C16—C17—C18−1.4 (2)
C3—C2—C1—O2−171.42 (14)C15—C16—C17—C20176.70 (15)
C7—C2—C1—O1−171.18 (13)C19—C18—C17—C161.7 (2)
C7—C2—C1—O28.2 (2)C19—C18—C17—C20−176.45 (14)
C1—C2—C3—C4179.87 (13)N1—C19—C18—C17−0.1 (2)
C7—C2—C3—C40.2 (2)N2—C20—C17—C165.3 (2)
C1—C2—C7—C6178.94 (14)N2—C20—C17—C18−176.65 (15)
C3—C2—C7—C6−1.4 (2)O5—C20—C17—C16−174.85 (17)
C2—C3—C4—C50.9 (2)O5—C20—C17—C183.2 (2)
C6—C5—C4—C3−0.8 (2)

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O2iii0.862.082.9242 (17)165
N2—H2B···O2iv0.862.112.9439 (17)163
C4—H4···O5v0.932.413.298 (2)160
C6—H6···O7vi0.932.503.223 (2)135
C15—H15···O6vi0.932.323.2049 (19)159
C16—H16···O2iv0.932.443.3541 (18)169
C3—H3···Cg10.932.733.6332 (17)163

Symmetry codes: (iii) −x+2, −y, −z; (iv) x, y−1, z; (v) x+1/2, −y+1/2, z+1/2; (vi) −x+5/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2939).

References

  • Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962–966.
  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009). Acta Cryst. E65, m651–m652. [PMC free article] [PubMed]
  • Hökelek, T. & Necefoğlu, H. (1996). Acta Cryst. C52, 1128–1131.
  • Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr.27, 108–111. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography