PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1829–o1830.
Published online 2008 August 23. doi:  10.1107/S1600536808026962
PMCID: PMC2960698

2-Hydr­oxy-N′-(2-methoxy­naphthyl­idene)benzohydrazide

Abstract

The title Schiff base compound, C19H16N2O3, prepared by the reaction of 2-meth­oxy-1-naphthyl­aldehyde and 2-hydroxy­benzohydrazide, crystallizes with two independent mol­ecules in the asymmetric unit. Each mol­ecule exists in a trans configuration with respect to the methyl­idene group. The naphthyl ring system make dihedral angles of 65.0 (2)° and 55.8 (2)° with the planes of the benzene rings. Intra­molecular N—H(...)O and O—H(...)O hydrogen bonds help to stabilize the mol­ecular conformations. In the crystal structure, mol­ecules are linked into one-dimensional chains parallel to the c axis by inter­molecular O—H(...)N and O—H(...)O hydrogen bonds.

Related literature

For the biological properties of hydrazones, see: Bedia et al. (2006 [triangle]); Rollas et al. (2002 [triangle]); Fun et al. (2008 [triangle]). For our previous reports on hydrazones, see: Qiu, Fang et al. (2006 [triangle]); Qiu, Luo et al. (2006a [triangle],b [triangle]); Qiu, Xu et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For related structures, see: Singh et al. (2007 [triangle]); Narayana et al. (2007 [triangle]); Cui et al. (2007 [triangle]); Diao et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1829-scheme1.jpg

Experimental

Crystal data

  • C19H16N2O3
  • M r = 320.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1829-efi1.jpg
  • a = 15.186 (3) Å
  • b = 9.059 (2) Å
  • c = 24.135 (3) Å
  • β = 108.331 (3)°
  • V = 3151.8 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 (2) K
  • 0.10 × 0.08 × 0.07 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.991, T max = 0.994
  • 17807 measured reflections
  • 6805 independent reflections
  • 4792 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.120
  • S = 1.03
  • 6805 reflections
  • 443 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026962/at2612sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026962/at2612Isup2.hkl

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

Acknowledgments

The author acknowledges the Education Office of Anhui Province (project No. KJ2008B178).

supplementary crystallographic information

Comment

Hyrazone compounds, which derived from the reaction of aldehydes with hydrazides, have been widely studied due to their excellent biological properties (Bedia et al., 2006; Rollas et al., 2002; Fun et al., 2008). Recently, we have reported a few Schiff hydrazone compounds (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006a,b; Qiu, Xu et al., 2006), we report herein the crystal structure of the title new compound, (I).

Compound (I) crystallizes with two independent molecules in the asymmetric unit (Fig. 1). Each molecule exists in a trans configuration with respect to the methylidene group. The naphthyl rings make dihedral angles of 65.0 (2)° and 55.8 (2)° with the planes of the benzene rings. The bond lengths and angles in (I) are found to have normal values (Allen et al., 1987) and comparable to the values in the similar compounds (Singh et al., 2007; Narayana et al., 2007; Cui et al., 2007; Diao et al., 2008). Intramolecular O–H···O and N–H···O hydrogen bonds (Table 1) help to stabilize the molecular conformations. In the crystal structure, molecules are linked into one-dimensional chains parallel to the c axis by intermolecular O–H···N and O–H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

The title compound was prepared by the Schiff base condensation of equimolar (0.5 mmol each) 2-methoxy-1-naphthylaldehyde and 2-hydroxybenzohydrazide in methanol (20 ml). Excess methanol was removed from the reaction mixture with distillation. The colourless solid was filtered and dried in air. Colourless block-shaped crystals suitable for X-ray diffraction were obtained from a methanol solution.

Refinement

The imino H atoms were located in a difference map and refined with N–H distances restrained to 0.90 (1) Å. The remaining H atoms were positioned geometrically [C–H = 0.93–0.96 Å, O–H = 0.82 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl and Ohydroxyl). Rotating group models were used for the methyl groups.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The crystal packing and hydrogen bonding of (I), viewed along the b axis.

Crystal data

C19H16N2O3F000 = 1344
Mr = 320.34Dx = 1.350 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5815 reflections
a = 15.186 (3) Åθ = 2.4–28.1º
b = 9.059 (2) ŵ = 0.09 mm1
c = 24.135 (3) ÅT = 298 (2) K
β = 108.331 (3)ºBlock, colourless
V = 3151.8 (10) Å30.10 × 0.08 × 0.07 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer6805 independent reflections
Radiation source: fine-focus sealed tube4792 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 298(2) Kθmax = 27.0º
ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −10→19
Tmin = 0.991, Tmax = 0.994k = −11→11
17807 measured reflectionsl = −30→30

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120  w = 1/[σ2(Fo2) + (0.0503P)2 + 0.6715P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
6805 reflectionsΔρmax = 0.20 e Å3
443 parametersΔρmin = −0.21 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
O10.43570 (8)0.65866 (12)0.40673 (6)0.0577 (3)
O20.24611 (8)0.06121 (13)0.35547 (5)0.0573 (3)
O30.15519 (9)0.28893 (15)0.47890 (6)0.0654 (4)
H30.15030.28490.51170.098*
O40.16698 (9)−0.14482 (14)0.15763 (6)0.0652 (4)
O50.23207 (9)0.34100 (14)0.09458 (6)0.0665 (4)
O60.26324 (9)0.11903 (14)0.25093 (5)0.0636 (3)
H60.26930.10340.28540.095*
N10.36544 (9)0.26155 (15)0.41827 (6)0.0483 (3)
N20.27814 (9)0.24269 (15)0.42336 (6)0.0466 (3)
N30.10594 (10)0.13486 (16)0.08670 (6)0.0521 (4)
N40.17195 (9)0.16834 (16)0.13899 (6)0.0490 (3)
C10.49640 (10)0.42352 (17)0.43517 (7)0.0413 (4)
C20.51078 (11)0.56729 (17)0.41994 (7)0.0442 (4)
C30.59831 (12)0.61341 (19)0.41810 (8)0.0530 (4)
H3A0.60720.71020.40820.064*
C40.66957 (12)0.5156 (2)0.43086 (8)0.0556 (5)
H40.72700.54690.42910.067*
C50.65964 (11)0.36863 (19)0.44667 (7)0.0483 (4)
C60.73541 (13)0.2690 (2)0.46050 (8)0.0613 (5)
H6A0.79260.30100.45860.074*
C70.72615 (15)0.1284 (2)0.47645 (9)0.0696 (5)
H70.77630.06400.48540.084*
C80.64025 (14)0.0810 (2)0.47939 (9)0.0699 (6)
H80.6341−0.01550.49080.084*
C90.56529 (13)0.1723 (2)0.46597 (8)0.0576 (5)
H90.50900.13660.46800.069*
C100.57139 (11)0.32084 (18)0.44889 (7)0.0439 (4)
C110.40275 (10)0.38697 (18)0.43631 (7)0.0434 (4)
H110.36980.45610.45040.052*
C120.22305 (11)0.13587 (17)0.39171 (7)0.0436 (4)
C130.13277 (10)0.11120 (17)0.40235 (7)0.0421 (4)
C140.10236 (11)0.18085 (18)0.44498 (7)0.0470 (4)
C150.01809 (12)0.1424 (2)0.45176 (8)0.0574 (5)
H15−0.00140.18900.48020.069*
C16−0.03670 (13)0.0369 (2)0.41726 (9)0.0644 (5)
H16−0.09290.01140.42250.077*
C17−0.00877 (13)−0.0316 (2)0.37477 (9)0.0654 (5)
H17−0.0464−0.10260.35090.078*
C180.07502 (12)0.00486 (19)0.36748 (8)0.0535 (4)
H180.0934−0.04250.33870.064*
C190.44208 (15)0.8020 (2)0.38459 (12)0.0814 (7)
H19A0.48920.85730.41290.122*
H19B0.38350.85150.37670.122*
H19C0.45790.79420.34920.122*
C200.02531 (11)−0.02550 (18)0.13957 (7)0.0456 (4)
C210.08806 (12)−0.12555 (18)0.17276 (8)0.0496 (4)
C220.06931 (13)−0.2047 (2)0.21794 (8)0.0573 (5)
H220.1128−0.27080.24050.069*
C23−0.01255 (13)−0.1841 (2)0.22840 (8)0.0568 (5)
H23−0.0247−0.23830.25790.068*
C24−0.07948 (11)−0.08342 (18)0.19611 (7)0.0476 (4)
C25−0.16522 (13)−0.0609 (2)0.20663 (8)0.0592 (5)
H25−0.1784−0.11420.23600.071*
C26−0.22817 (13)0.0369 (2)0.17457 (9)0.0642 (5)
H26−0.28430.04990.18190.077*
C27−0.20917 (13)0.1186 (2)0.13057 (9)0.0630 (5)
H27−0.25260.18600.10890.076*
C28−0.12729 (12)0.1001 (2)0.11913 (8)0.0546 (4)
H28−0.11540.15590.08990.066*
C29−0.06034 (11)−0.00243 (17)0.15091 (7)0.0442 (4)
C300.04095 (12)0.0481 (2)0.08884 (8)0.0521 (4)
H30−0.00330.02810.05310.063*
C310.23628 (12)0.27271 (18)0.13895 (8)0.0480 (4)
C320.31301 (12)0.29697 (18)0.19424 (8)0.0497 (4)
C330.32713 (12)0.22094 (19)0.24690 (8)0.0521 (4)
C340.40499 (14)0.2494 (2)0.29426 (9)0.0671 (5)
H340.41440.19740.32890.080*
C350.46828 (16)0.3539 (3)0.29042 (10)0.0822 (7)
H350.52070.37140.32230.099*
C360.45451 (17)0.4331 (3)0.23953 (11)0.0847 (7)
H360.49670.50560.23730.102*
C370.37807 (15)0.4044 (2)0.19212 (10)0.0672 (5)
H370.36940.45750.15780.081*
C380.23682 (15)−0.2434 (3)0.19098 (11)0.0880 (7)
H38A0.2578−0.21180.23100.132*
H38B0.2881−0.24360.17570.132*
H38C0.2116−0.34130.18870.132*
H20.2587 (14)0.302 (2)0.4481 (8)0.080*
H4A0.1781 (14)0.116 (2)0.1714 (6)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0480 (7)0.0460 (7)0.0824 (9)−0.0025 (5)0.0255 (6)0.0106 (6)
O20.0597 (8)0.0567 (7)0.0590 (8)−0.0150 (6)0.0236 (6)−0.0042 (6)
O30.0675 (8)0.0794 (9)0.0541 (8)−0.0345 (7)0.0264 (7)−0.0193 (7)
O40.0550 (7)0.0666 (8)0.0763 (9)0.0205 (6)0.0238 (7)0.0149 (7)
O50.0687 (8)0.0665 (8)0.0698 (9)0.0089 (7)0.0296 (7)0.0261 (7)
O60.0772 (9)0.0642 (8)0.0499 (7)−0.0102 (7)0.0206 (7)0.0054 (6)
N10.0416 (7)0.0511 (8)0.0539 (8)−0.0098 (6)0.0173 (6)0.0013 (7)
N20.0391 (7)0.0490 (8)0.0520 (8)−0.0114 (6)0.0147 (6)−0.0003 (6)
N30.0466 (8)0.0639 (9)0.0484 (8)0.0113 (7)0.0186 (7)0.0105 (7)
N40.0476 (8)0.0555 (9)0.0464 (8)0.0072 (7)0.0184 (7)0.0101 (7)
C10.0385 (8)0.0446 (8)0.0400 (8)−0.0099 (7)0.0111 (6)−0.0020 (7)
C20.0409 (8)0.0443 (9)0.0486 (9)−0.0065 (7)0.0157 (7)−0.0011 (7)
C30.0491 (10)0.0491 (10)0.0649 (11)−0.0122 (8)0.0236 (8)0.0033 (8)
C40.0408 (9)0.0646 (11)0.0652 (12)−0.0126 (8)0.0220 (8)0.0004 (9)
C50.0419 (9)0.0572 (10)0.0454 (9)−0.0044 (8)0.0133 (7)−0.0042 (8)
C60.0471 (10)0.0761 (13)0.0607 (12)0.0048 (9)0.0171 (9)−0.0025 (10)
C70.0623 (13)0.0728 (14)0.0696 (13)0.0173 (11)0.0147 (10)0.0008 (11)
C80.0721 (14)0.0506 (11)0.0779 (14)0.0060 (10)0.0107 (11)0.0091 (10)
C90.0511 (10)0.0521 (10)0.0656 (12)−0.0050 (8)0.0127 (9)0.0063 (9)
C100.0418 (9)0.0471 (9)0.0402 (9)−0.0058 (7)0.0094 (7)−0.0032 (7)
C110.0387 (8)0.0466 (9)0.0437 (9)−0.0078 (7)0.0114 (7)0.0038 (7)
C120.0473 (9)0.0400 (8)0.0396 (9)−0.0079 (7)0.0079 (7)0.0058 (7)
C130.0431 (8)0.0412 (8)0.0379 (8)−0.0087 (7)0.0068 (6)0.0089 (7)
C140.0487 (9)0.0484 (9)0.0398 (9)−0.0128 (7)0.0079 (7)0.0032 (7)
C150.0545 (10)0.0672 (12)0.0537 (11)−0.0150 (9)0.0216 (8)0.0020 (9)
C160.0521 (11)0.0772 (13)0.0647 (12)−0.0234 (10)0.0198 (9)0.0046 (10)
C170.0616 (12)0.0699 (12)0.0619 (12)−0.0324 (10)0.0155 (10)−0.0068 (10)
C180.0577 (11)0.0516 (10)0.0491 (10)−0.0160 (8)0.0138 (8)−0.0034 (8)
C190.0717 (14)0.0544 (12)0.123 (2)0.0039 (10)0.0378 (13)0.0286 (12)
C200.0449 (9)0.0469 (9)0.0435 (9)−0.0001 (7)0.0118 (7)−0.0018 (7)
C210.0484 (9)0.0473 (9)0.0519 (10)0.0037 (8)0.0139 (8)−0.0013 (8)
C220.0642 (12)0.0476 (10)0.0541 (11)0.0044 (8)0.0102 (9)0.0064 (8)
C230.0714 (12)0.0505 (10)0.0500 (10)−0.0098 (9)0.0212 (9)0.0014 (8)
C240.0513 (10)0.0445 (9)0.0467 (9)−0.0120 (7)0.0150 (8)−0.0108 (7)
C250.0604 (11)0.0633 (11)0.0596 (11)−0.0223 (10)0.0270 (9)−0.0171 (9)
C260.0452 (10)0.0747 (13)0.0742 (13)−0.0112 (10)0.0211 (10)−0.0234 (11)
C270.0462 (10)0.0645 (12)0.0744 (13)0.0003 (9)0.0133 (9)−0.0095 (10)
C280.0449 (10)0.0568 (10)0.0591 (11)−0.0014 (8)0.0117 (8)−0.0015 (9)
C290.0429 (9)0.0427 (8)0.0453 (9)−0.0057 (7)0.0113 (7)−0.0083 (7)
C300.0458 (9)0.0649 (11)0.0446 (9)0.0091 (9)0.0126 (7)0.0049 (8)
C310.0503 (10)0.0434 (9)0.0595 (11)0.0140 (8)0.0307 (8)0.0099 (8)
C320.0547 (10)0.0458 (9)0.0576 (10)0.0058 (8)0.0304 (8)−0.0035 (8)
C330.0587 (11)0.0502 (9)0.0544 (11)0.0022 (8)0.0281 (9)−0.0053 (8)
C340.0711 (13)0.0813 (14)0.0524 (11)−0.0015 (11)0.0246 (10)−0.0123 (10)
C350.0760 (15)0.1089 (19)0.0671 (14)−0.0206 (14)0.0304 (12)−0.0308 (13)
C360.0874 (16)0.0939 (17)0.0848 (17)−0.0348 (13)0.0443 (14)−0.0277 (14)
C370.0785 (14)0.0622 (12)0.0746 (14)−0.0090 (10)0.0436 (12)−0.0052 (10)
C380.0680 (14)0.0909 (16)0.1037 (19)0.0353 (12)0.0250 (13)0.0250 (14)

Geometric parameters (Å, °)

O1—C21.3631 (19)C15—H150.9300
O1—C191.419 (2)C16—C171.375 (3)
O2—C121.2401 (19)C16—H160.9300
O3—C141.3635 (19)C17—C181.378 (2)
O3—H30.8200C17—H170.9300
O4—C211.370 (2)C18—H180.9300
O4—C381.426 (2)C19—H19A0.9600
O5—C311.2208 (19)C19—H19B0.9600
O6—C331.365 (2)C19—H19C0.9600
O6—H60.8200C20—C211.375 (2)
N1—C111.283 (2)C20—C291.426 (2)
N1—N21.3801 (18)C20—C301.477 (2)
N2—C121.348 (2)C21—C221.407 (2)
N2—H20.918 (19)C22—C231.357 (3)
N3—C301.275 (2)C22—H220.9300
N3—N41.376 (2)C23—C241.405 (2)
N4—C311.360 (2)C23—H230.9300
N4—H4A0.895 (9)C24—C251.418 (2)
C1—C21.389 (2)C24—C291.419 (2)
C1—C101.426 (2)C25—C261.354 (3)
C1—C111.469 (2)C25—H250.9300
C2—C31.407 (2)C26—C271.397 (3)
C3—C41.357 (2)C26—H260.9300
C3—H3A0.9300C27—C281.366 (2)
C4—C51.406 (2)C27—H270.9300
C4—H40.9300C28—C291.412 (2)
C5—C61.417 (2)C28—H280.9300
C5—C101.425 (2)C30—H300.9300
C6—C71.351 (3)C31—C321.486 (3)
C6—H6A0.9300C32—C371.399 (3)
C7—C81.396 (3)C32—C331.401 (2)
C7—H70.9300C33—C341.386 (3)
C8—C91.361 (3)C34—C351.373 (3)
C8—H80.9300C34—H340.9300
C9—C101.419 (2)C35—C361.381 (3)
C9—H90.9300C35—H350.9300
C11—H110.9300C36—C371.374 (3)
C12—C131.489 (2)C36—H360.9300
C13—C181.393 (2)C37—H370.9300
C13—C141.403 (2)C38—H38A0.9600
C14—C151.385 (2)C38—H38B0.9600
C15—C161.365 (3)C38—H38C0.9600
C2—O1—C19119.52 (13)O1—C19—H19A109.5
C14—O3—H3109.5O1—C19—H19B109.5
C21—O4—C38119.16 (15)H19A—C19—H19B109.5
C33—O6—H6109.5O1—C19—H19C109.5
C11—N1—N2114.42 (14)H19A—C19—H19C109.5
C12—N2—N1118.72 (14)H19B—C19—H19C109.5
C12—N2—H2121.3 (13)C21—C20—C29119.43 (15)
N1—N2—H2120.0 (13)C21—C20—C30121.17 (15)
C30—N3—N4116.65 (14)C29—C20—C30119.14 (14)
C31—N4—N3117.96 (14)O4—C21—C20115.65 (15)
C31—N4—H4A119.5 (14)O4—C21—C22123.30 (15)
N3—N4—H4A122.0 (14)C20—C21—C22121.03 (16)
C2—C1—C10119.50 (14)C23—C22—C21119.64 (17)
C2—C1—C11116.74 (14)C23—C22—H22120.2
C10—C1—C11123.76 (14)C21—C22—H22120.2
O1—C2—C1116.21 (13)C22—C23—C24122.10 (16)
O1—C2—C3122.76 (14)C22—C23—H23119.0
C1—C2—C3121.02 (15)C24—C23—H23119.0
C4—C3—C2119.53 (16)C23—C24—C25122.61 (17)
C4—C3—H3A120.2C23—C24—C29118.35 (15)
C2—C3—H3A120.2C25—C24—C29119.03 (16)
C3—C4—C5122.26 (15)C26—C25—C24120.98 (18)
C3—C4—H4118.9C26—C25—H25119.5
C5—C4—H4118.9C24—C25—H25119.5
C4—C5—C6121.23 (16)C25—C26—C27120.25 (18)
C4—C5—C10118.70 (15)C25—C26—H26119.9
C6—C5—C10120.07 (16)C27—C26—H26119.9
C7—C6—C5121.20 (18)C28—C27—C26120.50 (19)
C7—C6—H6A119.4C28—C27—H27119.8
C5—C6—H6A119.4C26—C27—H27119.8
C6—C7—C8119.15 (18)C27—C28—C29121.10 (18)
C6—C7—H7120.4C27—C28—H28119.4
C8—C7—H7120.4C29—C28—H28119.4
C9—C8—C7121.74 (19)C28—C29—C24118.11 (15)
C9—C8—H8119.1C28—C29—C20122.44 (15)
C7—C8—H8119.1C24—C29—C20119.44 (15)
C8—C9—C10121.28 (17)N3—C30—C20129.77 (16)
C8—C9—H9119.4N3—C30—H30115.1
C10—C9—H9119.4C20—C30—H30115.1
C9—C10—C5116.55 (15)O5—C31—N4120.90 (17)
C9—C10—C1124.44 (15)O5—C31—C32121.51 (16)
C5—C10—C1118.99 (14)N4—C31—C32117.56 (15)
N1—C11—C1121.33 (15)C37—C32—C33117.81 (18)
N1—C11—H11119.3C37—C32—C31115.67 (17)
C1—C11—H11119.3C33—C32—C31126.49 (16)
O2—C12—N2121.91 (15)O6—C33—C34120.55 (17)
O2—C12—C13121.29 (14)O6—C33—C32119.19 (16)
N2—C12—C13116.80 (15)C34—C33—C32120.26 (17)
C18—C13—C14117.65 (15)C35—C34—C33120.4 (2)
C18—C13—C12116.01 (15)C35—C34—H34119.8
C14—C13—C12126.31 (14)C33—C34—H34119.8
O3—C14—C15120.06 (15)C34—C35—C36120.3 (2)
O3—C14—C13119.73 (14)C34—C35—H35119.8
C15—C14—C13120.20 (15)C36—C35—H35119.8
C16—C15—C14120.86 (18)C37—C36—C35119.6 (2)
C16—C15—H15119.6C37—C36—H36120.2
C14—C15—H15119.6C35—C36—H36120.2
C15—C16—C17119.94 (17)C36—C37—C32121.5 (2)
C15—C16—H16120.0C36—C37—H37119.2
C17—C16—H16120.0C32—C37—H37119.2
C16—C17—C18120.04 (17)O4—C38—H38A109.5
C16—C17—H17120.0O4—C38—H38B109.5
C18—C17—H17120.0H38A—C38—H38B109.5
C17—C18—C13121.31 (17)O4—C38—H38C109.5
C17—C18—H18119.3H38A—C38—H38C109.5
C13—C18—H18119.3H38B—C38—H38C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N3i0.822.243.0049 (18)155
O3—H3···O5i0.822.302.914 (2)133
O6—H6···O20.821.872.6683 (17)164
N2—H2···O30.918 (19)1.942 (16)2.6518 (18)132.7 (17)
N4—H4A···O60.895 (9)1.948 (16)2.6581 (19)135.0 (18)
N4—H4A···O40.895 (9)2.38 (2)2.877 (2)114.9 (16)

Symmetry codes: (i) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2612).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
  • Bedia, K.-K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem.41, 1253–1261. [PubMed]
  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cui, J., Yin, H. & Qiao, Y. (2007). Acta Cryst. E63, o3548.
  • Diao, Y.-P., Zhen, Y.-H., Han, X. & Deng, S. (2008). Acta Cryst. E64, o101. [PMC free article] [PubMed]
  • Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. [PMC free article] [PubMed]
  • Narayana, B., Siddaraju, B. P., Raju, C. R., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o3522.
  • Qiu, X.-Y., Fang, X.-N., Liu, W.-S. & Zhu, H.-L. (2006). Acta Cryst. E62, o2685–o2686.
  • Qiu, X.-Y., Luo, Z.-G., Yang, S.-L. & Liu, W.-S. (2006a). Acta Cryst. E62, o3531–o3532.
  • Qiu, X.-Y., Luo, Q.-Y., Yang, S.-L. & Liu, W.-S. (2006b). Acta Cryst. E62, o4291–o4292.
  • Qiu, X.-Y., Xu, H.-J., Liu, W.-S. & Zhu, H.-L. (2006). Acta Cryst. E62, o2304–o2305.
  • Rollas, S., Gülerman, N. & Erdeniz, H. (2002). Farmaco, 57, 171–174. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Singh, N. K., Singh, M., Srivastava, A. K., Shrivastav, A. & Sharma, R. K. (2007). Acta Cryst. E63, o4895.

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