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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2864.
Published online 2009 October 28. doi:  10.1107/S1600536809043840
PMCID: PMC2971021
Copyright © De-Suo Yang 2009
N′-(5-Hydr­oxy-2-nitro­benzyl­idene)-2-methoxy­benzohydrazide
De-Suo Yanga*
aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721007, People’s Republic of China
Correspondence e-mail: desuoyang/at/yahoo.com.cn
Received October 19, 2009; Accepted October 23, 2009.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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Abstract
The asymmetric unit of the title compound, C15H13N3O5, contains two independent mol­ecules. Each mol­ecule displays an E configuration with respect to its C=N double bond. The dihedral angles between the two benzene rings are 11.1 (2) and 10.9 (2)° in the two mol­ecules. In the crystal structure, mol­ecules are linked through inter­molecular O—H(...)O hydrogen bonds, forming chains running along the a axis.
Related literature
For the biological and structural chemistry of hydrazone compounds, see: Avaji et al. (2009 [triangle]); Charkoudian et al. (2007 [triangle]); Cukurovali et al. (2006 [triangle]). For related structures, see: Yang (2008a [triangle],b [triangle],c [triangle],d [triangle],e, 2007a [triangle],b [triangle],c [triangle]); Yang & Guo (2006 [triangle]). For reference bond-length data, see: Allen et al. (1987 [triangle]).
An external file that holds a picture, illustration, etc. Object name is e-65-o2864-scheme1.jpg Object name is e-65-o2864-scheme1.jpg
Crystal data
  • C15H13N3O5
  • M r = 315.28
  • Triclinic, An external file that holds a picture, illustration, etc. Object name is e-65-o2864-efi1.jpg
  • a = 8.7540 (9) Å
  • b = 9.0529 (9) Å
  • c = 18.2159 (17) Å
  • α = 86.902 (5)°
  • β = 83.023 (5)°
  • γ = 82.509 (5)°
  • V = 1419.6 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.17 × 0.15 × 0.15 mm
Data collection
  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.981, T max = 0.983
  • 8779 measured reflections
  • 6066 independent reflections
  • 4236 reflections with I > 2σ(I)
  • R int = 0.017
Refinement
  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.123
  • S = 1.04
  • 6066 reflections
  • 425 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.26 e Å−3
Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.
​
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043840/wn2358sup1.cif
Click here to view.(23K, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043840/wn2358Isup2.hkl
Click here to view.(297K, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The author acknowledges Baoji University of Arts and Sciences for support.
supplementary crystallographic information
Comment
Hydrazone compounds have been of great interest for a long time. These compounds play an important role in biological and structural chemistry (Avaji et al., 2009; Charkoudian et al., 2007; Cukurovali et al., 2006). Recently, we have reported a few hydrazone compounds (Yang, 2008a,b,c,d,e, 2007a,b,c; Yang & Guo, 2006). As a further investigation in this area, the crystal structure of the new title hydrazone compound is reported.
The asymmetric unit of the title compound, Fig. 1, consists of two independent molecules. Each molecule displays an E configuration with respect to the C═N double bond. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 11.1 (2)°, and that between the C16—C21 and C24—C29 benzene rings is 10.9 (2)°. All the bond lengths are within normal ranges (Allen et al., 1987). The C7═N1 and C22═N4 bond lengths of 1.256 (2) and 1.260 (2) Å, respectively, conform to the values for double bonds. The bond length of 1.348 (2) Å between atoms C8 and N2, and that of 1.351 (2) Å between atoms C23 and N5, are intermediate between C—N single bonds and C═N double bonds, because of conjugation effects in the molecules.
In the crystal structure, molecules are linked through intermolecular O—H···O hydrogen bonds (Table 1), forming chains running along the a axis (Fig. 2).
Experimental
5-Hydroxy-2-nitrobenzaldehyde (0.1 mmol, 16.7 mg) and 2-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 5 days at room temperature.
Refinement
Nitrogen-bound atoms H2 and H5A were located in a difference Fourier map and refined isotropically, with N—H distances restrained to 0.90 (1) Å. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with O—H distances of 0.82 Å, C—H distances of 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and Cmethyl).
Figures
Fig. 1.
Fig. 1.
The structure of the asymmetric unit of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. Hydrogen bonds are shown as dashed (more ...)
Fig. 2.
Fig. 2.
Molecular packing, viewed along the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
Crystal data
C15H13N3O5Z = 4
Mr = 315.28F(000) = 656
Triclinic, P1Dx = 1.475 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7540 (9) ÅCell parameters from 2340 reflections
b = 9.0529 (9) Åθ = 2.5–25.3°
c = 18.2159 (17) ŵ = 0.11 mm−1
α = 86.902 (5)°T = 298 K
β = 83.023 (5)°Block, colorless
γ = 82.509 (5)°0.17 × 0.15 × 0.15 mm
V = 1419.6 (2) Å3
Data collection
Bruker SMART CCD diffractometer6066 independent reflections
Radiation source: fine-focus sealed tube4236 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→11
Tmin = 0.981, Tmax = 0.983k = −11→9
8779 measured reflectionsl = −23→23
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1933P] where P = (Fo2 + 2Fc2)/3
6066 reflections(Δ/σ)max = 0.001
425 parametersΔρmax = 0.23 e Å−3
2 restraintsΔρmin = −0.26 e Å−3
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
O10.43038 (17)0.56766 (15)0.20225 (9)0.0651 (4)
O20.51734 (15)0.97729 (14)0.11083 (7)0.0496 (3)
O30.04575 (17)0.86066 (17)−0.04665 (8)0.0648 (4)
O4−0.19271 (18)0.88756 (16)−0.06698 (8)0.0642 (4)
O5−0.22760 (16)0.36644 (15)0.16573 (7)0.0516 (4)
H5−0.17930.36390.20170.077*
O60.93551 (17)0.39747 (18)0.28075 (8)0.0630 (4)
O71.02232 (16)0.21547 (16)0.48449 (7)0.0548 (4)
O80.54241 (17)−0.09248 (17)0.43071 (8)0.0655 (4)
O90.30249 (18)−0.12659 (17)0.44316 (8)0.0662 (4)
O100.27735 (16)0.33708 (14)0.18156 (7)0.0489 (3)
H100.32490.40940.18140.073*
N10.20958 (17)0.68586 (16)0.12448 (8)0.0415 (4)
N20.32509 (17)0.76663 (16)0.13956 (9)0.0426 (4)
N3−0.08536 (19)0.82546 (17)−0.03512 (8)0.0426 (4)
N40.71155 (17)0.24869 (17)0.34137 (8)0.0405 (4)
N50.82807 (18)0.27753 (18)0.38088 (8)0.0437 (4)
N60.41209 (19)−0.06591 (17)0.41211 (8)0.0435 (4)
C1−0.02579 (19)0.67167 (19)0.07731 (9)0.0346 (4)
C2−0.1160 (2)0.70609 (19)0.01894 (9)0.0357 (4)
C3−0.2360 (2)0.6249 (2)0.00901 (10)0.0413 (4)
H3−0.29260.6485−0.03100.050*
C4−0.2708 (2)0.5109 (2)0.05763 (10)0.0433 (4)
H4−0.35050.45640.05070.052*
C5−0.1862 (2)0.47659 (19)0.11782 (9)0.0378 (4)
C6−0.06376 (19)0.55545 (19)0.12606 (9)0.0366 (4)
H6−0.00570.52960.16530.044*
C70.1012 (2)0.7541 (2)0.09190 (10)0.0398 (4)
H70.10110.85420.07730.048*
C80.4347 (2)0.6969 (2)0.17976 (10)0.0404 (4)
C90.56063 (19)0.7798 (2)0.19878 (10)0.0380 (4)
C100.6016 (2)0.9147 (2)0.16516 (10)0.0395 (4)
C110.7241 (2)0.9775 (2)0.18779 (11)0.0497 (5)
H110.75101.06730.16610.060*
C120.8050 (2)0.9064 (3)0.24229 (12)0.0584 (6)
H120.88650.94920.25730.070*
C130.7685 (2)0.7741 (3)0.27496 (12)0.0576 (6)
H130.82500.72670.31150.069*
C140.6473 (2)0.7120 (2)0.25317 (10)0.0479 (5)
H140.62240.62200.27540.058*
C150.5651 (2)1.1071 (2)0.07190 (12)0.0562 (5)
H15A0.55491.18700.10540.084*
H15B0.50111.13530.03300.084*
H15C0.67141.08660.05110.084*
C160.47579 (19)0.15649 (19)0.33463 (9)0.0350 (4)
C170.3836 (2)0.04192 (19)0.35190 (9)0.0352 (4)
C180.2637 (2)0.0237 (2)0.31102 (10)0.0404 (4)
H180.2052−0.05470.32310.048*
C190.2313 (2)0.1207 (2)0.25315 (10)0.0419 (4)
H190.15250.10710.22510.050*
C200.3170 (2)0.23981 (19)0.23648 (9)0.0373 (4)
C210.43944 (19)0.25484 (19)0.27658 (9)0.0365 (4)
H210.49830.33290.26410.044*
C220.6037 (2)0.1839 (2)0.37580 (10)0.0400 (4)
H220.60480.15440.42550.048*
C230.9387 (2)0.3552 (2)0.34549 (10)0.0413 (4)
C241.0637 (2)0.3942 (2)0.38721 (10)0.0420 (4)
C251.1028 (2)0.3282 (2)0.45480 (11)0.0451 (5)
C261.2213 (2)0.3780 (3)0.48783 (13)0.0611 (6)
H261.24810.33510.53280.073*
C271.2983 (3)0.4902 (3)0.45383 (16)0.0701 (7)
H271.37510.52460.47700.084*
C281.2647 (3)0.5530 (3)0.38670 (15)0.0669 (7)
H281.31990.62720.36370.080*
C291.1482 (2)0.5044 (2)0.35392 (12)0.0531 (5)
H291.12520.54640.30820.064*
C301.0611 (3)0.1437 (3)0.55204 (11)0.0626 (6)
H30A1.16980.10730.54720.094*
H30B1.00190.06170.56370.094*
H30C1.03800.21340.59090.094*
H20.331 (3)0.8598 (14)0.1214 (12)0.080*
H5A0.833 (3)0.243 (2)0.4276 (7)0.080*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
O10.0588 (9)0.0480 (9)0.0964 (12)−0.0217 (7)−0.0397 (8)0.0299 (8)
O20.0452 (8)0.0470 (8)0.0607 (9)−0.0190 (6)−0.0160 (6)0.0159 (6)
O30.0507 (9)0.0761 (11)0.0666 (10)−0.0205 (8)−0.0020 (7)0.0268 (8)
O40.0730 (10)0.0556 (9)0.0715 (10)−0.0181 (7)−0.0394 (8)0.0242 (7)
O50.0604 (9)0.0534 (8)0.0477 (8)−0.0284 (7)−0.0168 (7)0.0145 (6)
O60.0574 (9)0.0893 (11)0.0492 (9)−0.0331 (8)−0.0201 (7)0.0254 (8)
O70.0522 (8)0.0695 (10)0.0476 (8)−0.0127 (7)−0.0238 (7)0.0083 (7)
O80.0525 (9)0.0743 (10)0.0677 (10)−0.0008 (7)−0.0205 (8)0.0273 (8)
O90.0741 (11)0.0728 (10)0.0595 (9)−0.0395 (8)−0.0200 (8)0.0271 (8)
O100.0550 (9)0.0468 (8)0.0502 (8)−0.0150 (6)−0.0250 (6)0.0149 (6)
N10.0358 (8)0.0410 (9)0.0513 (9)−0.0146 (7)−0.0137 (7)0.0082 (7)
N20.0386 (8)0.0378 (8)0.0558 (10)−0.0144 (7)−0.0182 (7)0.0112 (7)
N30.0461 (9)0.0428 (9)0.0404 (9)−0.0097 (7)−0.0102 (7)0.0051 (7)
N40.0372 (8)0.0488 (9)0.0391 (8)−0.0115 (7)−0.0156 (7)0.0050 (7)
N50.0394 (9)0.0598 (10)0.0360 (8)−0.0171 (7)−0.0143 (7)0.0085 (7)
N60.0506 (10)0.0404 (9)0.0406 (9)−0.0082 (7)−0.0098 (7)0.0053 (7)
C10.0298 (9)0.0360 (9)0.0385 (9)−0.0057 (7)−0.0052 (7)0.0017 (7)
C20.0378 (9)0.0355 (9)0.0339 (9)−0.0055 (7)−0.0052 (7)0.0022 (7)
C30.0422 (10)0.0476 (11)0.0368 (10)−0.0089 (8)−0.0142 (8)0.0024 (8)
C40.0435 (11)0.0459 (11)0.0450 (11)−0.0171 (8)−0.0119 (8)0.0011 (8)
C50.0410 (10)0.0360 (9)0.0365 (9)−0.0083 (8)−0.0029 (8)0.0022 (7)
C60.0337 (9)0.0405 (10)0.0371 (9)−0.0076 (7)−0.0097 (7)0.0043 (7)
C70.0388 (10)0.0363 (10)0.0458 (10)−0.0105 (8)−0.0100 (8)0.0091 (8)
C80.0368 (10)0.0391 (10)0.0471 (11)−0.0101 (8)−0.0108 (8)0.0078 (8)
C90.0314 (9)0.0426 (10)0.0409 (10)−0.0061 (7)−0.0060 (7)−0.0028 (8)
C100.0325 (9)0.0446 (10)0.0422 (10)−0.0068 (8)−0.0044 (8)−0.0033 (8)
C110.0421 (11)0.0505 (12)0.0602 (13)−0.0177 (9)−0.0063 (9)−0.0070 (10)
C120.0470 (12)0.0711 (15)0.0638 (14)−0.0138 (11)−0.0193 (10)−0.0179 (12)
C130.0543 (13)0.0689 (15)0.0540 (13)−0.0043 (11)−0.0241 (10)−0.0102 (11)
C140.0476 (11)0.0512 (12)0.0459 (11)−0.0042 (9)−0.0124 (9)0.0013 (9)
C150.0533 (13)0.0510 (12)0.0652 (14)−0.0200 (10)−0.0035 (10)0.0141 (10)
C160.0319 (9)0.0398 (10)0.0327 (9)−0.0039 (7)−0.0040 (7)0.0022 (7)
C170.0369 (9)0.0353 (9)0.0331 (9)−0.0036 (7)−0.0058 (7)0.0025 (7)
C180.0431 (10)0.0391 (10)0.0417 (10)−0.0153 (8)−0.0075 (8)0.0032 (8)
C190.0421 (10)0.0451 (11)0.0421 (10)−0.0109 (8)−0.0149 (8)0.0007 (8)
C200.0386 (10)0.0392 (10)0.0341 (9)−0.0034 (8)−0.0080 (7)0.0040 (7)
C210.0350 (9)0.0379 (10)0.0383 (9)−0.0094 (7)−0.0081 (7)0.0050 (7)
C220.0385 (10)0.0479 (11)0.0351 (9)−0.0090 (8)−0.0116 (8)0.0084 (8)
C230.0371 (10)0.0455 (11)0.0426 (10)−0.0073 (8)−0.0096 (8)0.0045 (8)
C240.0312 (9)0.0459 (11)0.0498 (11)−0.0020 (8)−0.0087 (8)−0.0084 (9)
C250.0348 (10)0.0507 (11)0.0509 (12)−0.0012 (9)−0.0104 (8)−0.0107 (9)
C260.0478 (12)0.0715 (15)0.0688 (15)−0.0012 (11)−0.0264 (11)−0.0182 (12)
C270.0467 (13)0.0724 (16)0.099 (2)−0.0132 (12)−0.0231 (13)−0.0300 (15)
C280.0499 (13)0.0615 (15)0.0938 (19)−0.0185 (11)−0.0072 (13)−0.0183 (13)
C290.0434 (11)0.0504 (12)0.0667 (14)−0.0097 (9)−0.0041 (10)−0.0077 (10)
C300.0601 (14)0.0785 (16)0.0502 (12)0.0022 (12)−0.0255 (10)0.0047 (11)
Geometric parameters (Å, °)
O1—C81.223 (2)C9—C101.405 (3)
O2—C101.361 (2)C10—C111.391 (2)
O2—C151.423 (2)C11—C121.373 (3)
O3—N31.2217 (19)C11—H110.9300
O4—N31.2228 (19)C12—C131.367 (3)
O5—C51.346 (2)C12—H120.9300
O5—H50.8200C13—C141.371 (3)
O6—C231.223 (2)C13—H130.9300
O7—C251.366 (2)C14—H140.9300
O7—C301.418 (2)C15—H15A0.9600
O8—N61.220 (2)C15—H15B0.9600
O9—N61.231 (2)C15—H15C0.9600
O10—C201.344 (2)C16—C211.385 (2)
O10—H100.8200C16—C171.395 (2)
N1—C71.256 (2)C16—C221.475 (2)
N1—N21.3837 (19)C17—C181.390 (2)
N2—C81.348 (2)C18—C191.367 (2)
N2—H20.895 (10)C18—H180.9300
N3—C21.451 (2)C19—C201.393 (2)
N4—C221.260 (2)C19—H190.9300
N4—N51.3764 (19)C20—C211.393 (2)
N5—C231.351 (2)C21—H210.9300
N5—H5A0.895 (10)C22—H220.9300
N6—C171.451 (2)C23—C241.493 (2)
C1—C61.387 (2)C24—C291.388 (3)
C1—C21.399 (2)C24—C251.400 (3)
C1—C71.474 (2)C25—C261.394 (3)
C2—C31.392 (2)C26—C271.371 (3)
C3—C41.364 (2)C26—H260.9300
C3—H30.9300C27—C281.368 (3)
C4—C51.396 (2)C27—H270.9300
C4—H40.9300C28—C291.373 (3)
C5—C61.390 (2)C28—H280.9300
C6—H60.9300C29—H290.9300
C7—H70.9300C30—H30A0.9600
C8—C91.495 (2)C30—H30B0.9600
C9—C141.389 (3)C30—H30C0.9600
C10—O2—C15117.91 (15)C13—C14—C9121.9 (2)
C5—O5—H5109.5C13—C14—H14119.1
C25—O7—C30118.82 (15)C9—C14—H14119.1
C20—O10—H10109.5O2—C15—H15A109.5
C7—N1—N2117.33 (15)O2—C15—H15B109.5
C8—N2—N1117.45 (14)H15A—C15—H15B109.5
C8—N2—H2120.6 (15)O2—C15—H15C109.5
N1—N2—H2121.8 (15)H15A—C15—H15C109.5
O3—N3—O4122.64 (16)H15B—C15—H15C109.5
O3—N3—C2118.98 (15)C21—C16—C17117.22 (15)
O4—N3—C2118.38 (15)C21—C16—C22118.02 (16)
C22—N4—N5117.22 (15)C17—C16—C22124.70 (15)
C23—N5—N4117.46 (15)C18—C17—C16121.56 (15)
C23—N5—H5A121.0 (15)C18—C17—N6117.20 (15)
N4—N5—H5A121.5 (16)C16—C17—N6121.22 (15)
O8—N6—O9122.25 (16)C19—C18—C17120.27 (16)
O8—N6—C17119.37 (16)C19—C18—H18119.9
O9—N6—C17118.38 (15)C17—C18—H18119.9
C6—C1—C2117.02 (15)C18—C19—C20119.51 (16)
C6—C1—C7118.44 (15)C18—C19—H19120.2
C2—C1—C7124.49 (15)C20—C19—H19120.2
C3—C2—C1121.54 (16)O10—C20—C21122.29 (16)
C3—C2—N3117.21 (15)O10—C20—C19118.01 (15)
C1—C2—N3121.23 (15)C21—C20—C19119.70 (16)
C4—C3—C2120.29 (16)C16—C21—C20121.65 (16)
C4—C3—H3119.9C16—C21—H21119.2
C2—C3—H3119.9C20—C21—H21119.2
C3—C4—C5119.66 (16)N4—C22—C16117.72 (16)
C3—C4—H4120.2N4—C22—H22121.1
C5—C4—H4120.2C16—C22—H22121.1
O5—C5—C6122.68 (16)O6—C23—N5121.09 (16)
O5—C5—C4117.72 (16)O6—C23—C24119.70 (17)
C6—C5—C4119.59 (16)N5—C23—C24119.17 (16)
C1—C6—C5121.84 (16)C29—C24—C25118.61 (17)
C1—C6—H6119.1C29—C24—C23115.53 (17)
C5—C6—H6119.1C25—C24—C23125.85 (18)
N1—C7—C1118.35 (16)O7—C25—C26123.40 (19)
N1—C7—H7120.8O7—C25—C24117.22 (16)
C1—C7—H7120.8C26—C25—C24119.4 (2)
O1—C8—N2120.76 (16)C27—C26—C25119.8 (2)
O1—C8—C9119.55 (16)C27—C26—H26120.1
N2—C8—C9119.67 (15)C25—C26—H26120.1
C14—C9—C10118.09 (16)C28—C27—C26121.6 (2)
C14—C9—C8115.65 (16)C28—C27—H27119.2
C10—C9—C8126.22 (16)C26—C27—H27119.2
O2—C10—C11123.15 (17)C27—C28—C29118.8 (2)
O2—C10—C9117.06 (15)C27—C28—H28120.6
C11—C10—C9119.79 (17)C29—C28—H28120.6
C12—C11—C10119.68 (19)C28—C29—C24121.7 (2)
C12—C11—H11120.2C28—C29—H29119.1
C10—C11—H11120.2C24—C29—H29119.1
C13—C12—C11121.47 (19)O7—C30—H30A109.5
C13—C12—H12119.3O7—C30—H30B109.5
C11—C12—H12119.3H30A—C30—H30B109.5
C12—C13—C14119.1 (2)O7—C30—H30C109.5
C12—C13—H13120.5H30A—C30—H30C109.5
C14—C13—H13120.5H30B—C30—H30C109.5
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
O5—H5···O6i0.821.912.721 (2)169
O10—H10···O10.821.882.689 (2)168
Symmetry codes: (i) x−1, y, z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2358).
References
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