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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 May 29;65(Pt 6):o1410. doi: 10.1107/S160053680901914X

N′-(2-Hydr­oxy-3,5-diiodo­benzyl­idene)-2-methoxy­benzohydrazide

San-Jun Peng a,*, Fen Zhang b
PMCID: PMC2969706  PMID: 21583253

Abstract

The title compound, C15H12I2N2O3, was synthesized by the condensation of equimolar amounts of 3,5-diiodo­salicylaldehyde and 2-methoxy­benzohydrazide in a methanol solution. There are two independent mol­ecules, A and B, in the asymmetric unit. The dihedral angle between the two benzene rings is 30.2 (2)° for mol­ecule A and 21.7 (2)° for mol­ecule B. There are intra­molecular O—H⋯N and N—H⋯O hydrogen bonds in each mol­ecule. The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio.

Related literature

For background to Schiff bases and their complexes, see: Ali et al. (2005 ▶). For related structures, see: Yehye et al. (2008a ▶,b ▶); Jing et al. (2006 ▶); Ling et al. (2008 ▶).graphic file with name e-65-o1410-scheme1.jpg

Experimental

Crystal data

  • C15H12I2N2O3

  • M r = 522.07

  • Orthorhombic, Inline graphic

  • a = 16.073 (2) Å

  • b = 15.628 (2) Å

  • c = 13.284 (1) Å

  • V = 3336.8 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.78 mm−1

  • T = 298 K

  • 0.23 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.432, T max = 0.469

  • 26178 measured reflections

  • 7237 independent reflections

  • 4902 reflections with I > 2σ(I)

  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046

  • wR(F 2) = 0.101

  • S = 1.00

  • 7237 reflections

  • 407 parameters

  • 3 restraints

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

  • Δρmax = 0.78 e Å−3

  • Δρmin = −0.56 e Å−3

  • Absolute structure: Flack (1983 ▶), 3436 Friedel pairs

  • Flack parameter: 0.59 (3)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901914X/sj2624sup1.cif

e-65-o1410-sup1.cif (22KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901914X/sj2624Isup2.hkl

e-65-o1410-Isup2.hkl (354.1KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O4—H4⋯N3 0.82 1.90 2.577 (8) 139
O1—H1⋯N1 0.82 1.92 2.568 (8) 136
N2—H2⋯O3 0.90 (3) 1.91 (6) 2.613 (8) 134 (8)
N4—H4B⋯O6 0.89 (5) 1.98 (7) 2.629 (9) 128 (7)
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Acknowledgments

We acknowledge Changsha University of Science and Technology for research grants.

supplementary crystallographic information

Comment

Schiff bases such as hydrazides are known to act as versatile ligands in coordination chemistry (Ali et al., 2005). We report herein the crystal structure of the new title benzohydrazide derivative (I), Fig. 1.

Compound (I) consists two independent molecules, A and B in the asymmetric unit. The dihedral angles between the two benzene rings are 30.2 (2)° for A and 21.7 (2)° for B, respectively. All the bond lengths are comparable to those observed in other similar compounds (Yehye et al., 2008a,b; Jing et al., 2006); Ling et al., 2008). There are two intramolecular O–H···N and N–H···O hydrogen bonds (Table 1) in each molecule.

Experimental

2-Methoxybenzohydrazide (0.1 mmol, 16.6 mg) and 3,5-diiodosalicylaldehyde (0.1 mmol, 37.4 mg) were stirred at 318 K in methanol (10 ml) for 30 min. The filtrate was kept in air for a few days depositing colorless block-like crystals of (I).

Refinement

The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio. The number of Friedel pairs in the data set is 3436. Atoms H2 and H4B were located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å, and with Uiso set to 0.08 Å2. All H atoms bound to carbon and oxygen were refined using riding models with d(C–H) = 0.93–0.96 Å, d(O–H) = 0.82 Å, Uiso = 1.2Ueq(C) and 1.5Ueq(O and methyl C).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I), showing the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.

Crystal data

C15H12I2N2O3 F(000) = 1968
Mr = 522.07 Dx = 2.078 Mg m−3
Orthorhombic, Pna21 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n Cell parameters from 4242 reflections
a = 16.073 (2) Å θ = 2.3–24.5°
b = 15.628 (2) Å µ = 3.78 mm−1
c = 13.284 (1) Å T = 298 K
V = 3336.8 (6) Å3 Block, colorless
Z = 8 0.23 × 0.20 × 0.20 mm
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Data collection

Bruker SMART 1000 CCD area-detector diffractometer 7237 independent reflections
Radiation source: fine-focus sealed tube 4902 reflections with I > 2σ(I)
graphite Rint = 0.053
ω scans θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001) h = −20→20
Tmin = 0.432, Tmax = 0.469 k = −19→19
26178 measured reflections l = −16→16
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00 (Δ/σ)max < 0.001
7237 reflections Δρmax = 0.78 e Å−3
407 parameters Δρmin = −0.56 e Å−3
3 restraints Absolute structure: Flack (1983), 3436 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.59 (3)
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
I3 0.40540 (3) 0.37109 (4) 0.59648 (6) 0.0789 (2)
I4 0.75672 (4) 0.29448 (4) 0.71249 (6) 0.0744 (2)
O4 0.4652 (3) 0.5530 (4) 0.6664 (5) 0.0592 (16)
H4 0.4752 0.5974 0.6971 0.071*
O5 0.4563 (4) 0.7984 (3) 0.7103 (6) 0.0738 (18)
O6 0.7003 (4) 0.8732 (4) 0.7109 (6) 0.0745 (19)
N3 0.5663 (4) 0.6711 (4) 0.7246 (6) 0.0492 (17)
N4 0.5871 (4) 0.7542 (4) 0.7391 (6) 0.0552 (19)
C16 0.6078 (4) 0.5270 (5) 0.7135 (7) 0.0428 (18)
C17 0.5299 (5) 0.4972 (5) 0.6787 (6) 0.0430 (19)
C18 0.5183 (5) 0.4121 (5) 0.6577 (7) 0.052 (2)
C19 0.5820 (5) 0.3546 (5) 0.6660 (6) 0.048 (2)
H19 0.5740 0.2974 0.6493 0.057*
C20 0.6582 (5) 0.3831 (5) 0.6994 (6) 0.047 (2)
C21 0.6718 (5) 0.4676 (5) 0.7198 (7) 0.053 (2)
H21 0.7248 0.4856 0.7381 0.064*
C22 0.6248 (5) 0.6155 (5) 0.7341 (6) 0.047 (2)
H22 0.6777 0.6325 0.7541 0.057*
C23 0.5297 (5) 0.8171 (5) 0.7244 (6) 0.0452 (19)
C24 0.5589 (5) 0.9062 (5) 0.7306 (6) 0.0455 (19)
C25 0.6422 (5) 0.9340 (5) 0.7234 (7) 0.053 (2)
C26 0.6607 (7) 1.0209 (6) 0.7251 (8) 0.074 (3)
H26 0.7154 1.0391 0.7171 0.089*
C27 0.6000 (9) 1.0786 (6) 0.7381 (7) 0.085 (4)
H27 0.6137 1.1362 0.7431 0.102*
C28 0.5176 (8) 1.0543 (7) 0.7445 (7) 0.083 (3)
H28 0.4758 1.0950 0.7518 0.100*
C29 0.4986 (6) 0.9687 (6) 0.7397 (6) 0.061 (2)
H29 0.4430 0.9522 0.7428 0.073*
C30 0.7849 (5) 0.8953 (7) 0.6937 (8) 0.080 (3)
H30A 0.8055 0.9276 0.7499 0.119*
H30B 0.7890 0.9292 0.6336 0.119*
H30C 0.8173 0.8441 0.6860 0.119*
I1 0.81885 (3) 0.63308 (4) 0.55553 (6) 0.0747 (2)
I2 0.46921 (4) 0.71070 (4) 0.43332 (6) 0.0793 (2)
O1 0.7606 (3) 0.4525 (4) 0.4793 (5) 0.0549 (16)
H1 0.7425 0.4041 0.4890 0.082*
O2 0.7669 (3) 0.2033 (4) 0.4301 (7) 0.076 (2)
O3 0.5224 (3) 0.1360 (3) 0.4748 (5) 0.0639 (16)
N1 0.6578 (4) 0.3339 (4) 0.4300 (5) 0.0465 (16)
N2 0.6348 (4) 0.2499 (4) 0.4275 (6) 0.0540 (17)
C1 0.6177 (4) 0.4794 (5) 0.4342 (6) 0.0407 (18)
C2 0.6962 (5) 0.5073 (5) 0.4661 (6) 0.046 (2)
C3 0.7075 (4) 0.5914 (5) 0.4888 (6) 0.048 (2)
C4 0.6443 (5) 0.6517 (5) 0.4757 (6) 0.052 (2)
H4A 0.6537 0.7094 0.4883 0.063*
C5 0.5680 (5) 0.6235 (5) 0.4438 (7) 0.053 (2)
C6 0.5548 (5) 0.5392 (5) 0.4207 (6) 0.0451 (19)
H6 0.5035 0.5219 0.3958 0.054*
C7 0.6016 (5) 0.3892 (5) 0.4185 (7) 0.048 (2)
H7 0.5486 0.3717 0.3996 0.057*
C8 0.6933 (5) 0.1877 (5) 0.4350 (7) 0.0462 (19)
C9 0.6631 (5) 0.0984 (5) 0.4467 (6) 0.044 (2)
C10 0.5797 (5) 0.0735 (5) 0.4667 (6) 0.047 (2)
C11 0.5616 (6) −0.0131 (6) 0.4790 (7) 0.063 (2)
H11 0.5075 −0.0300 0.4938 0.075*
C12 0.6220 (8) −0.0729 (6) 0.4696 (8) 0.077 (3)
H12 0.6084 −0.1304 0.4766 0.093*
C13 0.7045 (7) −0.0501 (6) 0.4495 (7) 0.074 (3)
H13 0.7460 −0.0913 0.4437 0.089*
C14 0.7219 (6) 0.0346 (5) 0.4387 (6) 0.052 (2)
H14 0.7766 0.0503 0.4252 0.062*
C15 0.4365 (5) 0.1115 (6) 0.4888 (7) 0.066 (3)
H15A 0.4293 0.0880 0.5550 0.099*
H15B 0.4215 0.0694 0.4394 0.099*
H15C 0.4015 0.1609 0.4813 0.099*
H2 0.5807 (15) 0.237 (5) 0.435 (7) 0.080*
H4B 0.639 (2) 0.770 (5) 0.754 (7) 0.080*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
I3 0.0459 (3) 0.0612 (4) 0.1295 (6) −0.0160 (3) −0.0114 (4) −0.0033 (4)
I4 0.0618 (4) 0.0584 (4) 0.1029 (5) 0.0198 (3) −0.0071 (4) −0.0048 (4)
O4 0.034 (3) 0.054 (3) 0.089 (5) −0.002 (3) 0.003 (3) −0.001 (3)
O5 0.056 (4) 0.053 (4) 0.112 (5) 0.002 (3) 0.003 (4) 0.002 (4)
O6 0.048 (4) 0.067 (4) 0.108 (6) −0.011 (3) 0.003 (4) 0.010 (4)
N3 0.041 (4) 0.044 (4) 0.063 (5) −0.004 (3) 0.002 (4) −0.006 (4)
N4 0.045 (4) 0.038 (4) 0.083 (6) −0.001 (3) −0.012 (4) −0.012 (4)
C16 0.029 (4) 0.043 (4) 0.056 (5) 0.008 (3) −0.007 (4) 0.006 (4)
C17 0.045 (5) 0.042 (4) 0.042 (5) −0.003 (4) 0.009 (4) −0.003 (4)
C18 0.038 (4) 0.056 (5) 0.060 (6) −0.006 (4) 0.001 (4) 0.016 (5)
C19 0.057 (5) 0.040 (4) 0.047 (5) −0.009 (4) 0.009 (4) 0.008 (4)
C20 0.046 (4) 0.045 (5) 0.051 (5) 0.009 (4) 0.003 (4) −0.002 (4)
C21 0.039 (4) 0.056 (5) 0.064 (6) −0.009 (4) 0.013 (4) −0.005 (5)
C22 0.046 (5) 0.043 (5) 0.053 (6) −0.009 (4) −0.005 (4) −0.009 (4)
C23 0.042 (5) 0.053 (5) 0.041 (5) −0.006 (4) 0.004 (4) −0.003 (4)
C24 0.047 (4) 0.050 (5) 0.039 (5) −0.001 (4) 0.007 (4) 0.006 (4)
C25 0.056 (5) 0.054 (5) 0.048 (5) −0.002 (4) −0.005 (4) 0.006 (4)
C26 0.093 (7) 0.053 (6) 0.076 (7) −0.026 (6) −0.015 (6) 0.008 (6)
C27 0.152 (12) 0.038 (5) 0.065 (7) −0.015 (7) 0.019 (7) 0.002 (5)
C28 0.111 (9) 0.064 (7) 0.075 (8) 0.026 (6) 0.023 (7) 0.003 (5)
C29 0.079 (6) 0.056 (6) 0.047 (6) −0.003 (5) 0.005 (5) 0.003 (4)
C30 0.055 (6) 0.115 (8) 0.069 (7) −0.009 (6) 0.000 (5) 0.016 (6)
I1 0.0441 (3) 0.0585 (4) 0.1215 (6) −0.0146 (3) −0.0043 (3) −0.0101 (4)
I2 0.0761 (4) 0.0635 (4) 0.0985 (5) 0.0285 (3) −0.0265 (4) −0.0121 (4)
O1 0.031 (3) 0.045 (3) 0.088 (5) 0.004 (2) −0.002 (3) 0.000 (3)
O2 0.033 (3) 0.058 (4) 0.137 (6) 0.003 (3) 0.002 (4) −0.004 (4)
O3 0.045 (3) 0.051 (3) 0.096 (5) −0.003 (3) 0.005 (3) 0.000 (3)
N1 0.039 (4) 0.042 (4) 0.058 (4) 0.001 (3) −0.001 (3) −0.007 (4)
N2 0.041 (4) 0.039 (4) 0.082 (5) −0.007 (3) −0.004 (4) −0.003 (4)
C1 0.039 (4) 0.037 (4) 0.047 (5) −0.002 (3) 0.003 (4) −0.007 (4)
C2 0.035 (4) 0.050 (5) 0.052 (5) 0.002 (4) 0.007 (4) 0.005 (4)
C3 0.038 (4) 0.051 (5) 0.053 (5) −0.006 (4) 0.001 (4) −0.005 (4)
C4 0.059 (6) 0.033 (4) 0.065 (6) 0.001 (4) −0.004 (5) −0.009 (4)
C5 0.055 (5) 0.048 (5) 0.057 (6) 0.003 (4) −0.004 (4) 0.008 (5)
C6 0.040 (4) 0.061 (5) 0.035 (5) 0.008 (4) −0.013 (4) −0.004 (4)
C7 0.035 (4) 0.056 (5) 0.053 (5) −0.012 (4) −0.005 (4) 0.007 (4)
C8 0.043 (5) 0.037 (4) 0.058 (5) 0.002 (4) 0.007 (4) −0.008 (4)
C9 0.052 (5) 0.045 (4) 0.034 (5) 0.008 (4) 0.005 (4) 0.000 (4)
C10 0.062 (5) 0.043 (5) 0.035 (5) −0.013 (4) −0.007 (4) 0.003 (4)
C11 0.070 (6) 0.053 (6) 0.064 (6) −0.014 (5) −0.014 (5) 0.001 (5)
C12 0.127 (10) 0.038 (5) 0.068 (7) −0.007 (6) −0.009 (6) −0.002 (5)
C13 0.112 (9) 0.043 (5) 0.068 (7) 0.002 (6) −0.018 (6) 0.001 (5)
C14 0.061 (5) 0.043 (5) 0.051 (5) 0.004 (4) −0.001 (5) −0.008 (4)
C15 0.054 (5) 0.080 (6) 0.065 (6) −0.029 (5) −0.002 (5) −0.002 (5)
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Geometric parameters (Å, °)

I3—C18 2.090 (8) I1—C3 2.101 (7)
I4—C20 2.111 (7) I2—C5 2.098 (8)
O4—C17 1.367 (9) O1—C2 1.355 (8)
O4—H4 0.8200 O1—H1 0.8200
O5—C23 1.229 (9) O2—C8 1.210 (9)
O6—C25 1.342 (10) O3—C10 1.348 (10)
O6—C30 1.421 (10) O3—C15 1.445 (9)
N3—C22 1.287 (10) N1—C7 1.259 (10)
N3—N4 1.354 (8) N1—N2 1.364 (8)
N4—C23 1.362 (10) N2—C8 1.356 (9)
N4—H4B 0.89 (5) N2—H2 0.90 (3)
C16—C21 1.389 (10) C1—C6 1.389 (10)
C16—C17 1.414 (10) C1—C2 1.400 (10)
C16—C22 1.437 (10) C1—C7 1.448 (10)
C17—C18 1.371 (11) C2—C3 1.360 (10)
C18—C19 1.366 (11) C3—C4 1.396 (11)
C19—C20 1.377 (11) C4—C5 1.370 (11)
C19—H19 0.9300 C4—H4A 0.9300
C20—C21 1.365 (10) C5—C6 1.369 (10)
C21—H21 0.9300 C6—H6 0.9300
C22—H22 0.9300 C7—H7 0.9300
C23—C24 1.472 (11) C8—C9 1.485 (11)
C24—C29 1.382 (12) C9—C14 1.379 (10)
C24—C25 1.412 (11) C9—C10 1.421 (11)
C25—C26 1.390 (12) C10—C11 1.393 (11)
C26—C27 1.339 (15) C11—C12 1.353 (13)
C26—H26 0.9300 C11—H11 0.9300
C27—C28 1.381 (15) C12—C13 1.399 (14)
C27—H27 0.9300 C12—H12 0.9300
C28—C29 1.374 (12) C13—C14 1.360 (12)
C28—H28 0.9300 C13—H13 0.9300
C29—H29 0.9300 C14—H14 0.9300
C30—H30A 0.9600 C15—H15A 0.9600
C30—H30B 0.9600 C15—H15B 0.9600
C30—H30C 0.9600 C15—H15C 0.9600
C17—O4—H4 109.4 C2—O1—H1 109.5
C25—O6—C30 120.9 (7) C10—O3—C15 118.1 (6)
C22—N3—N4 116.9 (7) C7—N1—N2 117.7 (7)
N3—N4—C23 120.3 (7) C8—N2—N1 120.1 (6)
N3—N4—H4B 121 (6) C8—N2—H2 120 (6)
C23—N4—H4B 118 (6) N1—N2—H2 118 (6)
C21—C16—C17 117.1 (7) C6—C1—C2 119.0 (7)
C21—C16—C22 119.4 (7) C6—C1—C7 120.5 (7)
C17—C16—C22 123.3 (7) C2—C1—C7 120.5 (7)
O4—C17—C18 119.5 (7) O1—C2—C3 118.7 (7)
O4—C17—C16 120.1 (7) O1—C2—C1 122.0 (7)
C18—C17—C16 120.4 (7) C3—C2—C1 119.2 (7)
C19—C18—C17 121.3 (8) C2—C3—C4 121.8 (7)
C19—C18—I3 118.7 (7) C2—C3—I1 120.4 (6)
C17—C18—I3 119.6 (6) C4—C3—I1 117.6 (6)
C18—C19—C20 118.7 (8) C5—C4—C3 118.2 (8)
C18—C19—H19 120.7 C5—C4—H4A 120.9
C20—C19—H19 120.7 C3—C4—H4A 120.9
C21—C20—C19 121.3 (8) C6—C5—C4 121.2 (8)
C21—C20—I4 119.9 (6) C6—C5—I2 119.5 (6)
C19—C20—I4 118.8 (6) C4—C5—I2 119.3 (6)
C20—C21—C16 121.0 (8) C5—C6—C1 120.4 (7)
C20—C21—H21 119.5 C5—C6—H6 119.8
C16—C21—H21 119.5 C1—C6—H6 119.8
N3—C22—C16 119.5 (7) N1—C7—C1 121.5 (8)
N3—C22—H22 120.3 N1—C7—H7 119.2
C16—C22—H22 120.3 C1—C7—H7 119.2
O5—C23—N4 120.1 (7) O2—C8—N2 121.9 (7)
O5—C23—C24 122.6 (7) O2—C8—C9 121.0 (7)
N4—C23—C24 117.3 (7) N2—C8—C9 117.1 (7)
C29—C24—C25 117.0 (8) C14—C9—C10 117.6 (8)
C29—C24—C23 116.7 (7) C14—C9—C8 116.6 (7)
C25—C24—C23 126.2 (7) C10—C9—C8 125.9 (7)
O6—C25—C26 123.0 (8) O3—C10—C11 123.5 (8)
O6—C25—C24 116.7 (7) O3—C10—C9 117.4 (7)
C26—C25—C24 120.2 (9) C11—C10—C9 119.0 (8)
C27—C26—C25 120.3 (10) C12—C11—C10 120.7 (9)
C27—C26—H26 119.9 C12—C11—H11 119.7
C25—C26—H26 119.9 C10—C11—H11 119.7
C26—C27—C28 121.5 (9) C11—C12—C13 121.5 (9)
C26—C27—H27 119.3 C11—C12—H12 119.3
C28—C27—H27 119.3 C13—C12—H12 119.3
C29—C28—C27 118.6 (10) C14—C13—C12 117.5 (10)
C29—C28—H28 120.7 C14—C13—H13 121.2
C27—C28—H28 120.7 C12—C13—H13 121.2
C28—C29—C24 122.4 (9) C13—C14—C9 123.7 (9)
C28—C29—H29 118.8 C13—C14—H14 118.1
C24—C29—H29 118.8 C9—C14—H14 118.1
O6—C30—H30A 109.5 O3—C15—H15A 109.5
O6—C30—H30B 109.5 O3—C15—H15B 109.5
H30A—C30—H30B 109.5 H15A—C15—H15B 109.5
O6—C30—H30C 109.5 O3—C15—H15C 109.5
H30A—C30—H30C 109.5 H15A—C15—H15C 109.5
H30B—C30—H30C 109.5 H15B—C15—H15C 109.5
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O4—H4···N3 0.82 1.90 2.577 (8) 139
O1—H1···N1 0.82 1.92 2.568 (8) 136
N2—H2···O3 0.90 (3) 1.91 (6) 2.613 (8) 134 (8)
N4—H4B···O6 0.89 (5) 1.98 (7) 2.629 (9) 128 (7)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2624).

References

  1. Ali, H. M., Kamalul Aripin, N. F. & Ng, S. W. (2005). Acta Cryst. E61, m433–m434.
  2. Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  5. Jing, Z.-L., Zhao, Y.-L., Chen, X. & Yu, M. (2006). Acta Cryst. E62, o4087–o4088.
  6. Ling, C.-H., Chen, Y.-B., Huang, J.-A., Ji, C. & Liu, P. (2008). Acta Cryst. E64, o948. [DOI] [PMC free article] [PubMed]
  7. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  8. Yehye, W. A., Ariffin, A. & Ng, S. W. (2008a). Acta Cryst. E64, o960. [DOI] [PMC free article] [PubMed]
  9. Yehye, W. A., Ariffin, A. & Ng, S. W. (2008b). Acta Cryst. E64, o1452. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901914X/sj2624sup1.cif

e-65-o1410-sup1.cif (22KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901914X/sj2624Isup2.hkl

e-65-o1410-Isup2.hkl (354.1KB, hkl)

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

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

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