N′-(4-Hydroxy­benzyl­idene)-4-meth­oxybenzohydrazide

The title compound, C₁₅H₁₄N₂O₃, was prepared by the reaction of 4-hydroxy­benzaldehyde and 4-methoxy­benzohydrazide in methanol. The dihedral angle between the two benzene rings is 6.8 (1)°. The meth­oxy group is disordered over two orientations with occupancies of ca 0.63 and 0.37. In the major disorder component, the meth­oxy group is coplanar with the attached ring. In the crystal structure, the mol­ecules are linked into a three-dimensional framework by inter­molecular O—H...O and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.135
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5884
PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6]..      24.72 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        O3A
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C3     ..  C15A    ..       3.19 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C7     ..  C15     ..       3.19 Ang.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         26

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Schiff bases are readily synthesized by the reaction of aldehydes with primary amines (Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005; Habibi et al., 2007). We have reported a few Schiff bases and their complexes (Wei et al., 2008a,b; Wei et al., 2006; Wei & Wang, 2006; Zhu et al., 2007; Wang et al., 2006). In this paper, we report the crystal structure of a new Schiff base compound.

Bond lengths and angles in the title compound (Fig. 1) are comparable with those observed in other Schiff bases (Yehye et al., 2008; Odabaşoğlu et al., 2007; Yathirajan et al., 2007). The dihedral angle between the C1–C6 and C9–C14 phenyl rings is 6.8 (1)°, indicating that they are nearly coplanar. In the major disorder component, the methoxy group is coplanar with the attached ring [C15—O3—C12—C11 = -2.6 (6)°].

The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1). These hydrogen bonds link the molecules into a three-dimensional framework (Fig. 2).

Related literature

For the synthesis of Schiff bases, see: Akitsu & Einaga (2006); Butcher et al. (2005); Habibi et al. (2007); Pradeep (2005). For related Schiff base compounds, see: Wang et al. (2006); Wei et al. (2006, 2008a,b); Wei & Wang (2006); Zhu et al. (2007). For related structures, see: Odabaşoğlu et al. (2007); Yathirajan et al. (2007); Yehye et al. (2008).

S2. Experimental

4-Hydroxybenzaldehyde (1.0 mmol, 122.1 mg) and 4-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were added to methanol (30 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. After keeping the solution in air for 12 d, colourless needle-shaped crystals were formed.

S3. Refinement

H atoms were positioned geometrically (C–H = 0.93–0.96 Å, O–H = 0.82 Å, N–H = 0.86 Å) and refined as riding, with U_iso(H) = 1.2U_eq(C,N) and 1.5U_eq(O,C_methyl). The methoxy group is disordered over two sites with occupancies of 0.630 (2) and 0.370 (2). The corresponding C—O distances in both disorder components were restrained to be equal. The displacement parameters of atoms O3, O3A, C15 and C15A were restrained to an approximate isotropic behaviour. The low resolution is caused by weak diffraction of the crystal.

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compounnd, showing 30% probability displacement ellipsoids. Both disorder components are shown.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines. Only the major disorder component is shown.

N'-(4-Hydroxybenzylidene)-4-methoxybenzohydrazide

Crystal data

C15H14N2O3	F(000) = 1136
Mr = 270.28	Dx = 1.328 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2798 reflections
a = 12.342 (2) Å	θ = 2.4–24.1°
b = 7.854 (2) Å	µ = 0.09 mm^−1
c = 27.889 (3) Å	T = 296 K
V = 2703.4 (9) Å^3	Cut from needle, colourless
Z = 8	0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2308 independent reflections
Radiation source: fine-focus sealed tube	1591 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 24.7°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→12
Tmin = 0.979, Tmax = 0.981	k = −9→9
12214 measured reflections	l = −32→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0514P)^2 + 1.0313P] where P = (Fo^2 + 2Fc^2)/3
2308 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.24 e Å^−3
26 restraints	Δρmin = −0.24 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.91965 (15)	−0.0226 (3)	0.86782 (6)	0.0813 (6)
H1	0.9779	0.0115	0.8782	0.122*
O2	0.61634 (13)	0.0498 (2)	0.59539 (5)	0.0645 (5)
N1	0.76203 (15)	0.1620 (2)	0.65728 (6)	0.0591 (5)
N2	0.74642 (15)	0.2399 (2)	0.61337 (6)	0.0599 (5)
H2A	0.7848	0.3265	0.6051	0.072*
C1	0.86057 (18)	0.1561 (3)	0.73055 (8)	0.0588 (6)
C2	0.7901 (2)	0.0470 (3)	0.75378 (8)	0.0700 (7)
H2	0.7271	0.0123	0.7383	0.084*
C3	0.8111 (2)	−0.0109 (4)	0.79911 (8)	0.0752 (8)
H3	0.7623	−0.0838	0.8141	0.090*
C4	0.90430 (19)	0.0382 (3)	0.82278 (8)	0.0596 (6)
C5	0.9763 (2)	0.1447 (3)	0.80018 (8)	0.0653 (6)
H5	1.0401	0.1768	0.8155	0.078*
C6	0.9535 (2)	0.2038 (3)	0.75471 (8)	0.0701 (7)
H6	1.0020	0.2777	0.7399	0.084*
C7	0.8374 (2)	0.2223 (3)	0.68288 (8)	0.0673 (7)
H7	0.8792	0.3113	0.6709	0.081*
C8	0.67021 (18)	0.1775 (3)	0.58398 (7)	0.0546 (6)
C9	0.65325 (19)	0.2623 (3)	0.53725 (8)	0.0605 (6)
C10	0.5570 (2)	0.2357 (4)	0.51343 (10)	0.0882 (9)
H10	0.5031	0.1693	0.5274	0.106*
C11	0.5400 (3)	0.3083 (4)	0.46835 (11)	0.1097 (12)
H11	0.4747	0.2901	0.4525	0.132*
C12	0.6183 (4)	0.4056 (4)	0.44727 (10)	0.1047 (12)
C13	0.7138 (3)	0.4305 (4)	0.47006 (9)	0.0938 (10)
H13	0.7678	0.4953	0.4556	0.113*
C14	0.7314 (2)	0.3606 (3)	0.51443 (8)	0.0735 (7)
H14	0.7973	0.3795	0.5297	0.088*
O3	0.6249 (4)	0.4882 (5)	0.40185 (13)	0.0866 (14)	0.630 (7)
C15	0.5326 (4)	0.4557 (6)	0.37318 (19)	0.0891 (18)	0.630 (7)
H15A	0.5397	0.5142	0.3431	0.134*	0.630 (7)
H15B	0.4689	0.4953	0.3895	0.134*	0.630 (7)
H15C	0.5266	0.3355	0.3675	0.134*	0.630 (7)
O3A	0.5470 (5)	0.4517 (9)	0.40930 (19)	0.092 (2)	0.370 (7)
C15A	0.6242 (10)	0.5249 (18)	0.3782 (4)	0.123 (5)	0.370 (7)
H15D	0.5889	0.5632	0.3495	0.185*	0.370 (7)
H15E	0.6781	0.4416	0.3702	0.185*	0.370 (7)
H15F	0.6582	0.6199	0.3938	0.185*	0.370 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0866 (13)	0.0986 (14)	0.0586 (10)	−0.0037 (11)	−0.0139 (9)	0.0213 (10)
O2	0.0700 (10)	0.0642 (10)	0.0593 (9)	−0.0056 (9)	−0.0002 (8)	0.0010 (8)
N1	0.0716 (12)	0.0616 (12)	0.0440 (10)	−0.0018 (10)	−0.0069 (9)	0.0074 (9)
N2	0.0738 (12)	0.0587 (11)	0.0472 (10)	−0.0070 (10)	−0.0092 (10)	0.0078 (8)
C1	0.0698 (15)	0.0560 (13)	0.0507 (12)	−0.0037 (12)	−0.0085 (11)	0.0039 (11)
C2	0.0712 (16)	0.0746 (17)	0.0641 (14)	−0.0120 (14)	−0.0162 (12)	0.0100 (13)
C3	0.0751 (16)	0.0836 (19)	0.0668 (15)	−0.0157 (14)	−0.0104 (13)	0.0229 (14)
C4	0.0702 (15)	0.0594 (14)	0.0491 (13)	0.0066 (12)	−0.0070 (11)	0.0040 (11)
C5	0.0717 (15)	0.0651 (15)	0.0591 (14)	−0.0069 (13)	−0.0155 (12)	0.0025 (12)
C6	0.0786 (17)	0.0702 (17)	0.0615 (14)	−0.0191 (13)	−0.0114 (13)	0.0109 (12)
C7	0.0794 (17)	0.0673 (16)	0.0553 (14)	−0.0134 (13)	−0.0090 (12)	0.0096 (12)
C8	0.0612 (13)	0.0529 (13)	0.0498 (12)	0.0038 (11)	−0.0007 (11)	−0.0037 (10)
C9	0.0812 (17)	0.0507 (13)	0.0495 (12)	0.0051 (12)	−0.0145 (12)	−0.0050 (10)
C10	0.104 (2)	0.0766 (19)	0.0841 (19)	−0.0048 (16)	−0.0388 (17)	0.0022 (15)
C11	0.142 (3)	0.087 (2)	0.099 (2)	0.010 (2)	−0.075 (2)	−0.0072 (19)
C12	0.193 (4)	0.0605 (18)	0.0604 (18)	0.013 (2)	−0.040 (2)	−0.0018 (14)
C13	0.155 (3)	0.0744 (19)	0.0519 (15)	0.0010 (19)	−0.0118 (18)	0.0050 (13)
C14	0.103 (2)	0.0662 (16)	0.0512 (13)	−0.0025 (15)	−0.0111 (13)	0.0014 (12)
O3	0.105 (3)	0.090 (3)	0.064 (2)	−0.025 (2)	−0.024 (2)	0.0248 (19)
C15	0.115 (4)	0.090 (3)	0.063 (3)	0.003 (3)	−0.032 (3)	0.010 (2)
O3A	0.101 (5)	0.116 (5)	0.059 (4)	0.009 (4)	−0.019 (3)	0.019 (3)
C15A	0.137 (8)	0.137 (8)	0.095 (7)	−0.006 (6)	0.002 (7)	0.043 (6)

Geometric parameters (Å, º)

O1—C4	1.357 (2)	C9—C10	1.377 (3)
O1—H1	0.82	C9—C14	1.389 (3)
O2—C8	1.245 (3)	C10—C11	1.396 (4)
N1—C7	1.265 (3)	C10—H10	0.93
N1—N2	1.382 (2)	C11—C12	1.365 (5)
N2—C8	1.340 (3)	C11—H11	0.93
N2—H2A	0.86	C12—C13	1.354 (5)
C1—C6	1.382 (3)	C12—O3A	1.424 (6)
C1—C2	1.382 (3)	C12—O3	1.426 (4)
C1—C7	1.456 (3)	C13—C14	1.371 (3)
C2—C3	1.368 (3)	C13—H13	0.93
C2—H2	0.93	C14—H14	0.93
C3—C4	1.381 (3)	O3—C15	1.415 (5)
C3—H3	0.93	C15—H15A	0.96
C4—C5	1.373 (3)	C15—H15B	0.96
C5—C6	1.379 (3)	C15—H15C	0.96
C5—H5	0.93	O3A—C15A	1.412 (8)
C6—H6	0.93	C15A—H15D	0.96
C7—H7	0.93	C15A—H15E	0.96
C8—C9	1.479 (3)	C15A—H15F	0.96
C4—O1—H1	109.5	C9—C10—C11	120.1 (3)
C7—N1—N2	115.9 (2)	C9—C10—H10	120.0
C8—N2—N1	118.51 (19)	C11—C10—H10	120.0
C8—N2—H2A	120.7	C12—C11—C10	120.7 (3)
N1—N2—H2A	120.7	C12—C11—H11	119.6
C6—C1—C2	117.5 (2)	C10—C11—H11	119.6
C6—C1—C7	120.7 (2)	C13—C12—C11	119.7 (3)
C2—C1—C7	121.7 (2)	C13—C12—O3A	148.3 (4)
C3—C2—C1	121.3 (2)	C11—C12—O3A	91.4 (4)
C3—C2—H2	119.3	C13—C12—O3	107.6 (3)
C1—C2—H2	119.3	C11—C12—O3	132.7 (3)
C2—C3—C4	120.5 (2)	C12—C13—C14	120.2 (3)
C2—C3—H3	119.8	C12—C13—H13	119.9
C4—C3—H3	119.8	C14—C13—H13	119.9
O1—C4—C5	123.3 (2)	C13—C14—C9	121.8 (3)
O1—C4—C3	117.4 (2)	C13—C14—H14	119.1
C5—C4—C3	119.3 (2)	C9—C14—H14	119.1
C4—C5—C6	119.7 (2)	C15—O3—C12	111.9 (4)
C4—C5—H5	120.2	O3—C15—H15A	109.5
C6—C5—H5	120.2	O3—C15—H15B	109.5
C5—C6—C1	121.7 (2)	H15A—C15—H15B	109.5
C5—C6—H6	119.1	O3—C15—H15C	109.5
C1—C6—H6	119.1	H15A—C15—H15C	109.5
N1—C7—C1	121.7 (2)	H15B—C15—H15C	109.5
N1—C7—H7	119.1	C15A—O3A—C12	98.2 (8)
C1—C7—H7	119.1	O3A—C15A—H15D	109.5
O2—C8—N2	120.9 (2)	O3A—C15A—H15E	109.5
O2—C8—C9	120.8 (2)	H15D—C15A—H15E	109.5
N2—C8—C9	118.3 (2)	O3A—C15A—H15F	109.5
C10—C9—C14	117.5 (2)	H15D—C15A—H15F	109.5
C10—C9—C8	118.6 (2)	H15E—C15A—H15F	109.5
C14—C9—C8	123.8 (2)
C7—N1—N2—C8	177.7 (2)	N2—C8—C9—C14	23.2 (3)
C6—C1—C2—C3	0.4 (4)	C14—C9—C10—C11	−0.9 (4)
C7—C1—C2—C3	−178.2 (2)	C8—C9—C10—C11	−177.4 (2)
C1—C2—C3—C4	−0.3 (4)	C9—C10—C11—C12	0.2 (5)
C2—C3—C4—O1	179.4 (2)	C10—C11—C12—C13	0.8 (5)
C2—C3—C4—C5	−0.6 (4)	C10—C11—C12—O3A	−173.0 (4)
O1—C4—C5—C6	−178.6 (2)	C10—C11—C12—O3	177.2 (4)
C3—C4—C5—C6	1.4 (4)	C11—C12—C13—C14	−1.0 (5)
C4—C5—C6—C1	−1.3 (4)	O3A—C12—C13—C14	167.1 (6)
C2—C1—C6—C5	0.4 (4)	O3—C12—C13—C14	−178.3 (3)
C7—C1—C6—C5	179.0 (2)	C12—C13—C14—C9	0.3 (4)
N2—N1—C7—C1	178.0 (2)	C10—C9—C14—C13	0.6 (4)
C6—C1—C7—N1	169.3 (2)	C8—C9—C14—C13	176.9 (2)
C2—C1—C7—N1	−12.1 (4)	C13—C12—O3—C15	174.2 (4)
N1—N2—C8—O2	−1.7 (3)	C11—C12—O3—C15	−2.5 (7)
N1—N2—C8—C9	179.47 (18)	O3A—C12—O3—C15	−17.1 (5)
O2—C8—C9—C10	20.6 (3)	C13—C12—O3A—C15A	22.4 (11)
N2—C8—C9—C10	−160.5 (2)	C11—C12—O3A—C15A	−167.9 (7)
O2—C8—C9—C14	−155.7 (2)	O3—C12—O3A—C15A	1.4 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.86	2.15	3.007 (3)	172
O1—H1···O2^ii	0.82	1.88	2.696 (2)	170

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