4-Meth-oxy-N'-(2-methoxy-benzyl-idene)benzohydrazide.

In the title compound, C(16)H(16)N(2)O(3), the two benzene rings are inclined to one another by 75.4 (2)°, and the mol-ecule adopts an E configuration about the C=N bond. In the crystal structure, symmetry-related mol-ecules are linked via inter-molecular 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 = 284.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.123

S = 0.98

3007 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.19 e Å−3

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.

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

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

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

C16H16N2O3	F(000) = 600
Mr = 284.31	Dx = 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

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

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(Fo2) + (0.0515P)2] where P = (Fo2 + 2Fc2)/3
3007 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) .