4-Meth­oxy-N′-(2-methoxy­benzyl­idene)benzohydrazide

Zhang, X.

doi:10.1107/S1600536809019102

organic compounds

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Volume 65| Part 6| June 2009| Page o1388

doi:10.1107/S1600536809019102

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4-Methoxy-N′-(2-methoxybenzylidene)benzohydrazide

Xinyou Zhang ^a ^*

^aDepartment of Chemistry, Baicheng Normal College, Baicheng 137000, People's Republic of China
^*Correspondence e-mail: xinyou_zhang@126.com

(Received 10 May 2009; accepted 20 May 2009; online 23 May 2009)

In the title compound, C₁₆H₁₆N₂O₃, the two benzene rings are inclined to one another by 75.4 (2)°, and the molecule adopts an E configuration about the C=N bond. In the crystal structure, symmetry-related molecules are linked via intermolecular N—H⋯O hydrogen bonds, forming chains running parallel to the c axis.

Related literature

For related structures, see: Alhadi et al. (2008 ), Küçükgüzel et al. (2003 ); Mohd Lair et al. (2009a ,b ); Li et al. (2009 ); Zhang et al. (2009 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₃
M_r = 284.31
Monoclinic, P 2₁ /c
a = 12.705 (1) Å
b = 16.053 (2) Å
c = 7.718 (1) Å
β = 107.233 (2)°
V = 1503.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.983, T_max = 0.984
8570 measured reflections
3007 independent reflections
1574 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.123
S = 0.98
3007 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.898 (9)	1.985 (11)	2.859 (2)	164 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019102/su2114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019102/su2114Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds are readily synthesized by the reaction of aldehydes with hydrazides. Recently, a large number of such compounds have been reported on (Alhadi et al., 2008; Küçükgüzel et al., 2003; Li et al., 2009; Zhang et al., 2009). In continuation of work in this area we report herein on the crystal structure of the title compound, a new hydrazone compound synthesized from the reaction of equimolar quantities of 2-methoxybenzaldehyde with 4-methoxybenzohydrazide in methanol.

The molecule structure of the title compound is illustrated in Fig. 1. The molecule adopts an E configuration about the C═N bond. The dihedral angle involving the two benzene rings is 75.4 (2)°. All the bond lengths are within normal values (Allen et al., 1987) and are comparable with those observed in the similar compounds (Mohd Lair et al., 2009a,b).

In the crystal structure of the compound, symmetry related molecules are linked through intermolecular N–H···O and N–H···N hydrogen bonds, forming chains running along the c axis (Table 1 and Fig. 2).

Related literature top

For related structures, see: Alhadi et al. (2008), Küçükgüzel et al. (2003); Mohd Lair et al. (2009a,b); Li et al. (2009); Zhang et al. (2009). For reference structural data, see: Allen et al. (1987).

Experimental top

2-Methoxybenzaldehyde (1.0 mmol, 136.2 mg) and 4-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were mixed in a methanol solution, and the mixture was refluxed for 1 h. Colorless block-shaped crystals of the title compound were formed by slow evaporation of the solution in air.

Computing details top

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probabilty level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound, with hydrogen bonds shown as dashed lines (see Table 1 for details). H-atoms not involved in hydrogen bonding have been omitted for clarity.

4-Methoxy-N'-(2-methoxybenzylidene)benzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₃	F(000) = 600
M_r = 284.31	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1023 reflections
a = 12.705 (1) Å	θ = 2.5–24.6°
b = 16.053 (2) Å	µ = 0.09 mm⁻¹
c = 7.718 (1) Å	T = 298 K
β = 107.233 (2)°	Block, colorless
V = 1503.5 (3) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3007 independent reflections
Radiation source: fine-focus sealed tube	1574 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 26.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→13
T_min = 0.983, T_max = 0.984	k = −19→17
8570 measured reflections	l = −9→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0515P)²] where P = (F_o² + 2F_c²)/3
3007 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₃	V = 1503.5 (3) Å³
M_r = 284.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.705 (1) Å	µ = 0.09 mm⁻¹
b = 16.053 (2) Å	T = 298 K
c = 7.718 (1) Å	0.20 × 0.20 × 0.18 mm
β = 107.233 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3007 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1574 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.984	R_int = 0.050
8570 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.13 e Å⁻³
3007 reflections	Δρ_min = −0.19 e Å⁻³
195 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
N1	0.11626 (13)	0.25479 (11)	0.8800 (2)	0.0459 (5)
N2	0.20751 (14)	0.23123 (11)	0.8290 (2)	0.0464 (5)
O1	−0.00123 (13)	0.47737 (10)	0.7280 (2)	0.0698 (5)
O2	0.27806 (12)	0.16021 (9)	1.0915 (2)	0.0572 (4)
O3	0.62405 (13)	0.06696 (12)	0.6746 (2)	0.0832 (6)
C1	−0.03802 (17)	0.34548 (14)	0.8236 (3)	0.0484 (6)
C2	−0.07099 (18)	0.42835 (15)	0.7881 (3)	0.0532 (6)
C3	−0.1678 (2)	0.45577 (18)	0.8150 (3)	0.0689 (8)
H3	−0.1900	0.5108	0.7906	0.083*
C4	−0.2316 (2)	0.4011 (2)	0.8783 (3)	0.0777 (8)
H4	−0.2970	0.4199	0.8958	0.093*
C5	−0.2007 (2)	0.3201 (2)	0.9158 (4)	0.0782 (8)
H5	−0.2440	0.2838	0.9593	0.094*
C6	−0.10359 (18)	0.29291 (16)	0.8878 (3)	0.0629 (7)
H6	−0.0821	0.2378	0.9130	0.075*
C7	0.06430 (17)	0.31710 (14)	0.7935 (3)	0.0477 (6)
H7	0.0918	0.3448	0.7103	0.057*
C8	0.28308 (17)	0.18075 (13)	0.9401 (3)	0.0456 (5)
C9	0.37276 (17)	0.15184 (13)	0.8685 (3)	0.0467 (6)
C10	0.47380 (19)	0.13301 (16)	0.9881 (3)	0.0693 (7)
H10	0.4844	0.1393	1.1119	0.083*
C11	0.5597 (2)	0.10505 (18)	0.9289 (4)	0.0772 (8)
H11	0.6276	0.0932	1.0121	0.093*
C12	0.54480 (19)	0.09484 (15)	0.7470 (3)	0.0598 (7)
C13	0.44375 (19)	0.11214 (15)	0.6249 (3)	0.0620 (7)
H13	0.4330	0.1045	0.5014	0.074*
C14	0.35890 (17)	0.14068 (13)	0.6849 (3)	0.0527 (6)
H14	0.2912	0.1527	0.6013	0.063*
C15	0.7272 (2)	0.04266 (18)	0.7970 (4)	0.0888 (9)
H15A	0.7609	0.0897	0.8689	0.133*
H15B	0.7745	0.0226	0.7295	0.133*
H15C	0.7157	−0.0007	0.8750	0.133*
C16	−0.0288 (2)	0.56282 (15)	0.6910 (4)	0.0780 (8)
H16A	−0.0998	0.5670	0.6022	0.117*
H16B	0.0255	0.5890	0.6454	0.117*
H16C	−0.0309	0.5902	0.8006	0.117*
H2	0.2197 (19)	0.2603 (13)	0.737 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0431 (10)	0.0511 (12)	0.0482 (11)	0.0074 (9)	0.0208 (9)	0.0010 (9)
N2	0.0464 (10)	0.0510 (12)	0.0481 (12)	0.0108 (9)	0.0236 (9)	0.0054 (9)
O1	0.0741 (11)	0.0536 (11)	0.0878 (13)	0.0155 (9)	0.0333 (10)	0.0116 (9)
O2	0.0637 (10)	0.0662 (10)	0.0492 (9)	0.0145 (8)	0.0284 (8)	0.0100 (8)
O3	0.0635 (11)	0.1180 (15)	0.0804 (13)	0.0380 (10)	0.0401 (11)	0.0142 (11)
C1	0.0489 (13)	0.0565 (15)	0.0416 (13)	0.0076 (11)	0.0162 (11)	−0.0018 (11)
C2	0.0526 (14)	0.0630 (16)	0.0447 (14)	0.0127 (13)	0.0154 (11)	−0.0016 (11)
C3	0.0665 (17)	0.085 (2)	0.0557 (16)	0.0325 (15)	0.0195 (14)	0.0003 (13)
C4	0.0543 (16)	0.121 (3)	0.0627 (18)	0.0267 (17)	0.0252 (14)	0.0017 (17)
C5	0.0587 (16)	0.106 (2)	0.080 (2)	0.0090 (16)	0.0360 (15)	0.0130 (17)
C6	0.0578 (15)	0.0715 (17)	0.0648 (17)	0.0077 (13)	0.0266 (13)	0.0044 (13)
C7	0.0484 (13)	0.0530 (14)	0.0458 (13)	0.0035 (11)	0.0202 (11)	0.0012 (11)
C8	0.0450 (13)	0.0454 (13)	0.0493 (14)	0.0025 (11)	0.0182 (11)	−0.0011 (11)
C9	0.0451 (13)	0.0513 (14)	0.0454 (13)	0.0055 (10)	0.0162 (11)	−0.0009 (10)
C10	0.0563 (15)	0.106 (2)	0.0462 (15)	0.0222 (15)	0.0168 (13)	0.0041 (14)
C11	0.0512 (15)	0.120 (2)	0.0616 (18)	0.0299 (15)	0.0180 (13)	0.0122 (16)
C12	0.0540 (15)	0.0704 (17)	0.0627 (17)	0.0178 (12)	0.0292 (14)	0.0071 (13)
C13	0.0608 (15)	0.0799 (18)	0.0499 (15)	0.0157 (13)	0.0235 (13)	−0.0013 (12)
C14	0.0433 (13)	0.0639 (15)	0.0520 (15)	0.0104 (11)	0.0157 (11)	−0.0005 (12)
C15	0.0634 (18)	0.112 (2)	0.102 (2)	0.0400 (16)	0.0407 (17)	0.0286 (18)
C16	0.094 (2)	0.0503 (17)	0.085 (2)	0.0136 (14)	0.0189 (17)	0.0054 (14)

Geometric parameters (Å, º) top

N1—C7	1.273 (2)	C6—H6	0.9300
N1—N2	1.383 (2)	C7—H7	0.9300
N2—C8	1.351 (3)	C8—C9	1.481 (3)
N2—H2	0.898 (9)	C9—C10	1.375 (3)
O1—C2	1.365 (3)	C9—C14	1.387 (3)
O1—C16	1.424 (3)	C10—C11	1.378 (3)
O2—C8	1.234 (2)	C10—H10	0.9300
O3—C12	1.364 (2)	C11—C12	1.369 (3)
O3—C15	1.424 (3)	C11—H11	0.9300
C1—C6	1.377 (3)	C12—C13	1.377 (3)
C1—C2	1.397 (3)	C13—C14	1.372 (3)
C1—C7	1.460 (3)	C13—H13	0.9300
C2—C3	1.379 (3)	C14—H14	0.9300
C3—C4	1.378 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.366 (4)	C15—H15C	0.9600
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.384 (3)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600

C7—N1—N2	114.46 (17)	C10—C9—C14	117.94 (19)
C8—N2—N1	118.77 (17)	C10—C9—C8	119.13 (19)
C8—N2—H2	123.7 (15)	C14—C9—C8	122.9 (2)
N1—N2—H2	115.9 (15)	C9—C10—C11	121.5 (2)
C2—O1—C16	118.51 (18)	C9—C10—H10	119.2
C12—O3—C15	117.7 (2)	C11—C10—H10	119.2
C6—C1—C2	118.4 (2)	C12—C11—C10	119.8 (2)
C6—C1—C7	121.9 (2)	C12—C11—H11	120.1
C2—C1—C7	119.7 (2)	C10—C11—H11	120.1
O1—C2—C3	124.4 (2)	O3—C12—C11	124.4 (2)
O1—C2—C1	115.38 (19)	O3—C12—C13	115.9 (2)
C3—C2—C1	120.2 (2)	C11—C12—C13	119.7 (2)
C4—C3—C2	119.6 (3)	C14—C13—C12	120.2 (2)
C4—C3—H3	120.2	C14—C13—H13	119.9
C2—C3—H3	120.2	C12—C13—H13	119.9
C5—C4—C3	121.3 (2)	C13—C14—C9	120.9 (2)
C5—C4—H4	119.4	C13—C14—H14	119.6
C3—C4—H4	119.4	C9—C14—H14	119.6
C4—C5—C6	118.7 (3)	O3—C15—H15A	109.5
C4—C5—H5	120.6	O3—C15—H15B	109.5
C6—C5—H5	120.6	H15A—C15—H15B	109.5
C1—C6—C5	121.7 (2)	O3—C15—H15C	109.5
C1—C6—H6	119.2	H15A—C15—H15C	109.5
C5—C6—H6	119.2	H15B—C15—H15C	109.5
N1—C7—C1	120.65 (19)	O1—C16—H16A	109.5
N1—C7—H7	119.7	O1—C16—H16B	109.5
C1—C7—H7	119.7	H16A—C16—H16B	109.5
O2—C8—N2	122.35 (19)	O1—C16—H16C	109.5
O2—C8—C9	122.1 (2)	H16A—C16—H16C	109.5
N2—C8—C9	115.56 (19)	H16B—C16—H16C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	1.99 (1)	2.859 (2)	164 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₃
M_r	284.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.705 (1), 16.053 (2), 7.718 (1)
β (°)	107.233 (2)
V (Å³)	1503.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8570, 3007, 1574
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.123, 0.98
No. of reflections	3007
No. of parameters	195
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.19

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.898 (9)	1.985 (11)	2.859 (2)	164 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

References

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