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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1550.
Published online 2010 June 5. doi:  10.1107/S1600536810020477
PMCID: PMC3006911

N′-[1-(2-Hy­droxy­phen­yl)ethyl­idene]-2-meth­oxy­benzohydrazide

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C16H16N2O3, in which the dihedral angles between the two aromatic rings are 13.0 (3) and 6.4 (3)°. Intra­molecular O—H(...)N and N—H(...)O hydrogen bonds are observed in both mol­ecules, forming S(6) rings in all cases.

Related literature

For related structures, see: Lu et al. (2008a [triangle],b [triangle],c [triangle]); Xiao & Wei (2009 [triangle]); He (2008 [triangle]); Shi et al. (2007 [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-66-o1550-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O3
  • M r = 284.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1550-efi1.jpg
  • a = 11.5610 (12) Å
  • b = 10.8074 (11) Å
  • c = 22.544 (2) Å
  • β = 92.244 (5)°
  • V = 2814.6 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.20 × 0.17 × 0.17 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.981, T max = 0.984
  • 16351 measured reflections
  • 6065 independent reflections
  • 3390 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.146
  • S = 1.01
  • 6065 reflections
  • 391 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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 global, I. DOI: 10.1107/S1600536810020477/wn2390sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020477/wn2390Isup2.hkl

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

Acknowledgments

The authors thank the Scientific Research Foundation of Shaanxi University of Technology (project No. SLGQD0708) for financial support.

supplementary crystallographic information

Comment

Recently we have reported a number of Schiff bases derived from the condensation of aldehydes or ketones with benzohydrazides (Lu et al., 2008a,b,c) We report here the crystal structure of the new title Schiff base compound.

In the crystal structure of the title compound, Fig. 1, there are two independent molecules in the asymmetric unit. The bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Xiao & Wei, 2009; He, 2008; Shi et al., 2007). The dihedral angles between the two aromatic rings in molecules A and B are 13.0 (3) and 6.4 (3)°, respectively. Intramolecular O—H···N and N—H···O hydrogen bonds are observed in the molecules (Table 1).

Experimental

The title compound was prepared by the Schiff base condensation of 1-(2-hydroxyphenyl)ethanone (0.1 mol, 13.6 g) and 2-methoxybenzohydrazide (0.1 mol, 16.6 g) in 95% ethanol (70 ml). The excess ethanol was removed by distillation. The resulting colourless solid was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a 95% ethanol solution at room temperature.

Refinement

H2 attached to N2, and H4B attached to N4 were located in a difference map and refined with the N—H distance restrained to 0.90 (1) Å. The other H atoms were positioned geometrically (C—H = 0.93–0.96 Å and O—H = 0.82 Å) and refined using a riding model, with with Uiso(H) = xUeq(attached atom), where x = 1.5 for methyl H and hydroxyl H, 1.2 for all other carbon-bound H atoms. A rotating group model was used for the methyl and hydroxyl groups.

Figures

Fig. 1.
The molecular structure of the asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The dashed lines indicate hydrogen bonds.

Crystal data

C16H16N2O3F(000) = 1200
Mr = 284.31Dx = 1.342 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.5610 (12) ÅCell parameters from 3247 reflections
b = 10.8074 (11) Åθ = 2.5–24.5°
c = 22.544 (2) ŵ = 0.09 mm1
β = 92.244 (5)°T = 298 K
V = 2814.6 (5) Å3Block, colourless
Z = 80.20 × 0.17 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer6065 independent reflections
Radiation source: fine-focus sealed tube3390 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −14→14
Tmin = 0.981, Tmax = 0.984k = −13→13
16351 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0661P)2 + 0.2197P] where P = (Fo2 + 2Fc2)/3
6065 reflections(Δ/σ)max < 0.001
391 parametersΔρmax = 0.18 e Å3
2 restraintsΔρmin = −0.22 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
N10.32094 (13)0.29578 (16)0.92231 (7)0.0578 (4)
N20.34893 (13)0.35212 (17)0.97530 (7)0.0597 (4)
N30.16718 (12)0.07857 (14)0.00747 (7)0.0541 (4)
N40.17677 (13)0.16075 (15)0.05364 (7)0.0563 (4)
O10.17630 (13)0.27945 (15)0.83520 (7)0.0765 (5)
H10.20560.31110.86520.115*
O20.21621 (14)0.50002 (16)0.95829 (7)0.0969 (6)
O30.47037 (12)0.36530 (14)1.07416 (6)0.0750 (4)
O40.23773 (13)−0.12009 (15)−0.03935 (7)0.0826 (5)
H40.2346−0.0665−0.01370.124*
O50.31539 (14)0.04667 (16)0.10021 (7)0.0888 (5)
O60.11005 (11)0.36046 (13)0.10849 (6)0.0684 (4)
C10.33944 (15)0.14134 (19)0.85116 (8)0.0549 (5)
C20.24499 (17)0.1865 (2)0.81688 (9)0.0602 (5)
C30.2162 (2)0.1340 (2)0.76206 (10)0.0767 (6)
H30.15320.16450.73970.092*
C40.2791 (2)0.0384 (2)0.74065 (10)0.0797 (7)
H4A0.25830.00350.70410.096*
C50.3730 (2)−0.0064 (2)0.77297 (10)0.0780 (6)
H50.4165−0.07090.75810.094*
C60.40240 (18)0.0440 (2)0.82710 (10)0.0710 (6)
H60.46620.01270.84860.085*
C70.37168 (15)0.1933 (2)0.90977 (8)0.0563 (5)
C80.45543 (18)0.1287 (2)0.95166 (9)0.0759 (6)
H8A0.52210.18020.95900.114*
H8B0.47890.05190.93440.114*
H8C0.41900.11260.98840.114*
C90.29454 (16)0.4577 (2)0.98954 (9)0.0606 (5)
C100.33544 (15)0.52031 (19)1.04600 (8)0.0569 (5)
C110.41947 (15)0.4758 (2)1.08692 (8)0.0577 (5)
C120.44709 (18)0.5422 (2)1.13798 (9)0.0729 (6)
H120.50200.51151.16540.087*
C130.3940 (2)0.6530 (3)1.14833 (11)0.0827 (7)
H130.41270.69671.18290.099*
C140.3136 (2)0.6999 (2)1.10817 (12)0.0865 (7)
H140.27880.77591.11500.104*
C150.28485 (19)0.6335 (2)1.05760 (11)0.0733 (6)
H150.23000.66551.03050.088*
C160.56308 (19)0.3193 (3)1.11158 (10)0.0882 (8)
H16A0.62370.37991.11460.132*
H16B0.59260.24441.09500.132*
H16C0.53530.30261.15040.132*
C170.08689 (14)0.00942 (18)−0.08365 (8)0.0505 (5)
C180.15800 (15)−0.09596 (19)−0.08333 (9)0.0607 (5)
C190.14807 (18)−0.1806 (2)−0.12944 (11)0.0790 (7)
H190.1947−0.2508−0.12840.095*
C200.07172 (17)−0.1636 (2)−0.17628 (10)0.0748 (6)
H200.0673−0.2208−0.20710.090*
C210.00145 (18)−0.0615 (2)−0.17773 (10)0.0701 (6)
H21−0.0511−0.0493−0.20950.084*
C220.00875 (16)0.0225 (2)−0.13226 (9)0.0627 (5)
H22−0.04010.0909−0.13370.075*
C230.09365 (15)0.10144 (17)−0.03562 (8)0.0516 (5)
C240.01927 (17)0.2152 (2)−0.03747 (10)0.0704 (6)
H24A−0.03600.2105−0.00690.106*
H24B−0.02080.2209−0.07550.106*
H24C0.06700.2871−0.03130.106*
C250.25190 (16)0.1365 (2)0.09986 (9)0.0572 (5)
C260.25187 (15)0.22604 (17)0.15067 (8)0.0524 (5)
C270.18211 (15)0.33129 (18)0.15560 (9)0.0552 (5)
C280.18812 (18)0.4015 (2)0.20709 (10)0.0680 (6)
H280.14090.47060.21050.082*
C290.2635 (2)0.3694 (2)0.25311 (10)0.0747 (6)
H290.26640.41680.28760.090*
C300.33427 (19)0.2686 (2)0.24897 (10)0.0744 (6)
H300.38620.24830.28000.089*
C310.32742 (17)0.1977 (2)0.19816 (9)0.0640 (6)
H310.37490.12860.19560.077*
C320.0333 (2)0.4636 (2)0.11268 (11)0.0884 (7)
H32A−0.01630.45120.14530.133*
H32B−0.01290.47080.07650.133*
H32C0.07760.53790.11900.133*
H20.4078 (13)0.330 (2)1.0002 (8)0.080*
H4B0.1314 (15)0.2279 (14)0.0561 (9)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0546 (9)0.0627 (11)0.0555 (10)0.0014 (8)−0.0037 (8)0.0059 (8)
N20.0567 (10)0.0669 (11)0.0546 (10)0.0094 (9)−0.0078 (8)0.0061 (9)
N30.0520 (9)0.0543 (10)0.0559 (10)0.0033 (8)0.0014 (8)0.0039 (8)
N40.0548 (9)0.0540 (10)0.0599 (10)0.0068 (8)−0.0006 (8)0.0027 (9)
O10.0811 (10)0.0791 (11)0.0680 (10)0.0200 (9)−0.0146 (8)0.0047 (8)
O20.0924 (11)0.0879 (12)0.1065 (12)0.0312 (10)−0.0459 (10)−0.0091 (10)
O30.0696 (9)0.0887 (11)0.0652 (9)0.0255 (8)−0.0161 (7)0.0016 (8)
O40.0723 (9)0.0714 (10)0.1018 (12)0.0242 (8)−0.0265 (9)−0.0125 (9)
O50.0913 (11)0.0879 (11)0.0855 (11)0.0431 (10)−0.0196 (9)−0.0160 (9)
O60.0639 (8)0.0594 (9)0.0810 (10)0.0151 (7)−0.0093 (7)0.0014 (8)
C10.0500 (10)0.0588 (12)0.0562 (11)−0.0027 (9)0.0049 (9)0.0117 (10)
C20.0605 (12)0.0613 (13)0.0590 (13)0.0002 (11)0.0038 (10)0.0109 (10)
C30.0808 (15)0.0853 (17)0.0629 (14)0.0030 (14)−0.0124 (12)0.0035 (13)
C40.0867 (16)0.0848 (17)0.0674 (14)−0.0089 (14)−0.0005 (13)−0.0085 (13)
C50.0758 (15)0.0801 (16)0.0784 (15)0.0034 (13)0.0076 (13)−0.0091 (13)
C60.0620 (12)0.0771 (16)0.0738 (15)0.0055 (12)0.0013 (11)0.0023 (13)
C70.0484 (10)0.0649 (13)0.0557 (12)0.0010 (10)0.0036 (9)0.0140 (10)
C80.0722 (14)0.0903 (17)0.0645 (13)0.0219 (13)−0.0069 (11)0.0079 (12)
C90.0521 (11)0.0626 (13)0.0665 (13)0.0036 (10)−0.0057 (10)0.0109 (11)
C100.0504 (10)0.0592 (13)0.0611 (12)−0.0015 (10)0.0018 (9)0.0094 (10)
C110.0492 (11)0.0680 (14)0.0560 (12)−0.0017 (10)0.0051 (9)0.0073 (10)
C120.0639 (13)0.0939 (18)0.0607 (13)−0.0043 (13)−0.0005 (10)0.0002 (13)
C130.0853 (16)0.0885 (19)0.0746 (16)−0.0078 (15)0.0056 (13)−0.0140 (14)
C140.0950 (18)0.0719 (16)0.0931 (18)0.0080 (14)0.0084 (15)−0.0084 (15)
C150.0737 (14)0.0649 (15)0.0810 (16)0.0070 (12)−0.0010 (12)0.0020 (12)
C160.0708 (14)0.109 (2)0.0834 (16)0.0260 (14)−0.0206 (12)0.0132 (15)
C170.0426 (9)0.0536 (11)0.0557 (11)−0.0009 (9)0.0060 (8)0.0085 (9)
C180.0443 (10)0.0618 (13)0.0758 (14)0.0031 (10)−0.0020 (10)0.0009 (11)
C190.0604 (13)0.0698 (15)0.1064 (18)0.0114 (12)−0.0043 (13)−0.0211 (14)
C200.0588 (13)0.0823 (17)0.0833 (16)−0.0042 (12)0.0015 (12)−0.0186 (13)
C210.0653 (13)0.0808 (16)0.0640 (13)−0.0014 (12)−0.0014 (10)0.0029 (12)
C220.0615 (12)0.0649 (13)0.0615 (12)0.0060 (11)0.0022 (10)0.0097 (11)
C230.0459 (10)0.0524 (11)0.0569 (11)0.0018 (9)0.0082 (9)0.0099 (9)
C240.0713 (13)0.0676 (14)0.0717 (14)0.0174 (11)−0.0035 (11)0.0031 (11)
C250.0501 (11)0.0600 (13)0.0614 (12)0.0036 (10)−0.0003 (9)0.0036 (10)
C260.0461 (10)0.0505 (11)0.0605 (12)−0.0033 (9)0.0023 (9)0.0054 (10)
C270.0477 (10)0.0529 (12)0.0647 (12)−0.0042 (9)0.0003 (9)0.0055 (10)
C280.0673 (13)0.0553 (13)0.0815 (15)−0.0005 (11)0.0033 (12)−0.0061 (12)
C290.0824 (15)0.0703 (15)0.0708 (15)−0.0098 (13)−0.0035 (12)−0.0101 (12)
C300.0778 (14)0.0761 (16)0.0679 (14)−0.0004 (13)−0.0138 (11)0.0008 (13)
C310.0610 (12)0.0641 (13)0.0663 (13)0.0025 (10)−0.0038 (10)0.0064 (11)
C320.0823 (15)0.0685 (15)0.113 (2)0.0279 (13)−0.0103 (14)0.0000 (14)

Geometric parameters (Å, °)

N1—C71.290 (2)C12—H120.9300
N1—N21.368 (2)C13—C141.369 (3)
N2—C91.347 (3)C13—H130.9300
N2—H20.896 (9)C14—C151.377 (3)
N3—C231.289 (2)C14—H140.9300
N3—N41.370 (2)C15—H150.9300
N4—C251.356 (2)C16—H16A0.9600
N4—H4B0.899 (9)C16—H16B0.9600
O1—C21.355 (2)C16—H16C0.9600
O1—H10.8200C17—C221.400 (2)
O2—C91.215 (2)C17—C181.405 (3)
O3—C111.367 (2)C17—C231.470 (3)
O3—C161.427 (2)C18—C191.386 (3)
O4—C181.352 (2)C19—C201.362 (3)
O4—H40.8200C19—H190.9300
O5—C251.217 (2)C20—C211.370 (3)
O6—C271.361 (2)C20—H200.9300
O6—C321.430 (2)C21—C221.369 (3)
C1—C21.401 (3)C21—H210.9300
C1—C61.401 (3)C22—H220.9300
C1—C71.470 (3)C23—C241.500 (3)
C2—C31.388 (3)C24—H24A0.9600
C3—C41.363 (3)C24—H24B0.9600
C3—H30.9300C24—H24C0.9600
C4—C51.372 (3)C25—C261.499 (3)
C4—H4A0.9300C26—C311.389 (3)
C5—C61.367 (3)C26—C271.401 (3)
C5—H50.9300C27—C281.386 (3)
C6—H60.9300C28—C291.373 (3)
C7—C81.498 (3)C28—H280.9300
C8—H8A0.9600C29—C301.367 (3)
C8—H8B0.9600C29—H290.9300
C8—H8C0.9600C30—C311.378 (3)
C9—C101.502 (3)C30—H300.9300
C10—C151.386 (3)C31—H310.9300
C10—C111.399 (3)C32—H32A0.9600
C11—C121.383 (3)C32—H32B0.9600
C12—C131.370 (3)C32—H32C0.9600
C7—N1—N2118.64 (16)O3—C16—H16A109.5
C9—N2—N1119.21 (16)O3—C16—H16B109.5
C9—N2—H2115.1 (14)H16A—C16—H16B109.5
N1—N2—H2125.2 (14)O3—C16—H16C109.5
C23—N3—N4118.66 (15)H16A—C16—H16C109.5
C25—N4—N3119.30 (16)H16B—C16—H16C109.5
C25—N4—H4B117.8 (14)C22—C17—C18116.45 (18)
N3—N4—H4B122.7 (14)C22—C17—C23121.50 (17)
C2—O1—H1109.5C18—C17—C23122.05 (17)
C11—O3—C16119.98 (17)O4—C18—C19117.16 (18)
C18—O4—H4109.5O4—C18—C17122.82 (19)
C27—O6—C32119.43 (17)C19—C18—C17120.02 (19)
C2—C1—C6116.99 (19)C20—C19—C18121.6 (2)
C2—C1—C7121.85 (18)C20—C19—H19119.2
C6—C1—C7121.17 (18)C18—C19—H19119.2
O1—C2—C3116.81 (19)C19—C20—C21119.6 (2)
O1—C2—C1122.93 (19)C19—C20—H20120.2
C3—C2—C1120.2 (2)C21—C20—H20120.2
C4—C3—C2120.8 (2)C22—C21—C20119.8 (2)
C4—C3—H3119.6C22—C21—H21120.1
C2—C3—H3119.6C20—C21—H21120.1
C3—C4—C5120.1 (2)C21—C22—C17122.6 (2)
C3—C4—H4A119.9C21—C22—H22118.7
C5—C4—H4A119.9C17—C22—H22118.7
C6—C5—C4119.8 (2)N3—C23—C17116.08 (16)
C6—C5—H5120.1N3—C23—C24122.58 (18)
C4—C5—H5120.1C17—C23—C24121.34 (16)
C5—C6—C1122.0 (2)C23—C24—H24A109.5
C5—C6—H6119.0C23—C24—H24B109.5
C1—C6—H6119.0H24A—C24—H24B109.5
N1—C7—C1115.04 (17)C23—C24—H24C109.5
N1—C7—C8123.38 (19)H24A—C24—H24C109.5
C1—C7—C8121.56 (19)H24B—C24—H24C109.5
C7—C8—H8A109.5O5—C25—N4121.80 (19)
C7—C8—H8B109.5O5—C25—C26121.87 (17)
H8A—C8—H8B109.5N4—C25—C26116.32 (17)
C7—C8—H8C109.5C31—C26—C27117.67 (18)
H8A—C8—H8C109.5C31—C26—C25115.32 (17)
H8B—C8—H8C109.5C27—C26—C25126.98 (17)
O2—C9—N2121.67 (19)O6—C27—C28122.40 (18)
O2—C9—C10121.6 (2)O6—C27—C26117.57 (18)
N2—C9—C10116.69 (17)C28—C27—C26120.03 (18)
C15—C10—C11117.8 (2)C29—C28—C27120.3 (2)
C15—C10—C9115.91 (18)C29—C28—H28119.9
C11—C10—C9126.25 (19)C27—C28—H28119.9
O3—C11—C12122.77 (18)C30—C29—C28120.9 (2)
O3—C11—C10117.10 (18)C30—C29—H29119.6
C12—C11—C10120.1 (2)C28—C29—H29119.6
C13—C12—C11120.3 (2)C29—C30—C31119.0 (2)
C13—C12—H12119.8C29—C30—H30120.5
C11—C12—H12119.8C31—C30—H30120.5
C14—C13—C12120.6 (2)C30—C31—C26122.1 (2)
C14—C13—H13119.7C30—C31—H31118.9
C12—C13—H13119.7C26—C31—H31118.9
C13—C14—C15119.3 (2)O6—C32—H32A109.5
C13—C14—H14120.3O6—C32—H32B109.5
C15—C14—H14120.3H32A—C32—H32B109.5
C14—C15—C10121.8 (2)O6—C32—H32C109.5
C14—C15—H15119.1H32A—C32—H32C109.5
C10—C15—H15119.1H32B—C32—H32C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.822.535 (2)144
O4—H4···N30.821.822.541 (2)145
N2—H2···O30.90 (1)1.83 (2)2.591 (2)141 (2)
N4—H4B···O60.90 (1)1.88 (2)2.619 (2)138 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2390).

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