N'-(3,4-Dimeth-oxy-benzyl-idene)benzo-hydrazide.

The crystal structure of the title Schiff base compound, C(16)H(16)N(2)O(3), is characterized by chains of mol-ecules linked by inter-molecular N-H⋯O hydrogen bonds running along the c axis. Further stabilization is provided by weak C-H⋯O contacts. The dihedral angle between the aromatic rings is 38.31 (7)°.

Related literature

For related structures see: Alhadi et al. (2009 ▶); Das & Pal (2004 ▶); Tamboura et al. (2009 ▶); Zhou et al. (2009 ▶).

Experimental

Crystal data

C16H16N2O3

M = 284.31

Monoclinic,

a = 12.612 (3) Å

b = 11.291 (2) Å

c = 9.892 (2) Å

β = 95.46 (3)°

V = 1402.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.5 × 0.4 × 0.15 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: numerical shape of crystal determined optically T min = 0.954, T max = 0.984

9840 measured reflections

3758 independent reflections

3054 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.131

S = 1.03

3758 reflections

200 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.24 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052128/bt5434sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052128/bt5434Isup2.hkl

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

C16H16N2O3	F(000) = 600
Mr = 284.31	Dx = 1.347 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3758 reflections
a = 12.612 (3) Å	θ = 2.4–29.2°
b = 11.291 (2) Å	µ = 0.09 mm−1
c = 9.892 (2) Å	T = 120 K
β = 95.46 (3)°	Plate, colorless
V = 1402.3 (5) Å3	0.5 × 0.4 × 0.15 mm
Z = 4

Stoe IPDS II diffractometer	3758 independent reflections
Radiation source: fine-focus sealed tube	3054 reflections with I > 2σ(I)
graphite	Rint = 0.052
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 2.4°
rotation method scans	h = −17→17
Absorption correction: numerical shape of crystal determined optically	k = −13→15
Tmin = 0.954, Tmax = 0.984	l = −13→13
9840 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.068P)2 + 0.4464P] where P = (Fo2 + 2Fc2)/3
3758 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.24 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
N2	0.77928 (9)	0.23464 (11)	0.31038 (12)	0.0204 (2)
O2	0.21028 (8)	0.00051 (9)	0.36444 (11)	0.0261 (2)
C10	0.84378 (10)	0.23202 (11)	0.20934 (13)	0.0184 (2)
N1	0.67552 (9)	0.19349 (11)	0.28696 (12)	0.0213 (2)
O1	0.30865 (8)	−0.00086 (9)	0.14959 (10)	0.0241 (2)
C2	0.46487 (10)	0.09658 (12)	0.26416 (13)	0.0205 (3)
H2	0.5013	0.0941	0.1867	0.025*
C11	0.95522 (10)	0.27473 (12)	0.24654 (13)	0.0185 (3)
C9	0.62290 (10)	0.19298 (12)	0.39172 (14)	0.0213 (3)
C1	0.51348 (10)	0.14808 (12)	0.38429 (14)	0.0205 (3)
C4	0.30798 (10)	0.05297 (12)	0.37871 (14)	0.0216 (3)
C3	0.36354 (10)	0.04990 (12)	0.26093 (14)	0.0208 (3)
C6	0.45799 (11)	0.15271 (13)	0.49842 (14)	0.0232 (3)
H6	0.4895	0.1871	0.5777	0.028*
C12	1.03648 (11)	0.21544 (13)	0.18854 (14)	0.0229 (3)
H12	1.0200	0.1524	0.1298	0.028*
C5	0.35478 (11)	0.10607 (13)	0.49557 (14)	0.0233 (3)
H5	0.3177	0.1108	0.5723	0.028*
C16	0.97968 (11)	0.37076 (13)	0.33195 (14)	0.0242 (3)
H16	0.9258	0.4113	0.3702	0.029*
C15	1.08551 (12)	0.40592 (14)	0.35984 (15)	0.0286 (3)
H15	1.1021	0.4706	0.4162	0.034*
C13	1.14179 (11)	0.24953 (13)	0.21765 (15)	0.0264 (3)
H13	1.1958	0.2089	0.1797	0.032*
C7	0.36427 (11)	−0.00915 (13)	0.03132 (14)	0.0246 (3)
H7A	0.3818	0.0689	0.0021	0.037*
H7B	0.3200	−0.0479	−0.0396	0.037*
H7C	0.4285	−0.0540	0.0518	0.037*
C14	1.16611 (11)	0.34472 (14)	0.30382 (15)	0.0278 (3)
H14	1.2367	0.3676	0.3241	0.033*
C8	0.14420 (12)	0.01622 (15)	0.47217 (16)	0.0305 (3)
H8A	0.1791	−0.0161	0.5545	0.046*
H8B	0.0776	−0.0238	0.4502	0.046*
H8C	0.1313	0.0992	0.4844	0.046*
O3	0.81626 (8)	0.19329 (9)	0.09466 (10)	0.0229 (2)
H9	0.6538 (15)	0.2201 (17)	0.4783 (19)	0.030 (5)*
H2A	0.8042 (16)	0.2565 (18)	0.392 (2)	0.036 (5)*

	U11	U22	U33	U12	U13	U23
N2	0.0185 (5)	0.0237 (6)	0.0189 (5)	−0.0038 (4)	0.0007 (4)	−0.0015 (4)
O2	0.0212 (5)	0.0279 (5)	0.0304 (5)	−0.0057 (4)	0.0089 (4)	−0.0066 (4)
C10	0.0200 (5)	0.0165 (6)	0.0187 (6)	0.0008 (4)	0.0010 (4)	0.0011 (5)
N1	0.0183 (5)	0.0223 (6)	0.0231 (5)	−0.0025 (4)	0.0001 (4)	−0.0003 (4)
O1	0.0200 (4)	0.0283 (5)	0.0240 (5)	−0.0045 (4)	0.0025 (4)	−0.0055 (4)
C2	0.0198 (6)	0.0214 (6)	0.0207 (6)	−0.0003 (5)	0.0032 (5)	−0.0005 (5)
C11	0.0194 (6)	0.0182 (6)	0.0177 (6)	−0.0011 (4)	0.0009 (4)	0.0031 (5)
C9	0.0202 (6)	0.0205 (6)	0.0230 (6)	−0.0016 (5)	0.0004 (5)	−0.0016 (5)
C1	0.0196 (6)	0.0188 (6)	0.0230 (6)	−0.0005 (5)	0.0014 (5)	−0.0004 (5)
C4	0.0194 (6)	0.0190 (6)	0.0267 (6)	−0.0009 (5)	0.0042 (5)	−0.0007 (5)
C3	0.0207 (6)	0.0193 (6)	0.0224 (6)	0.0000 (5)	0.0013 (5)	−0.0007 (5)
C6	0.0236 (6)	0.0233 (7)	0.0226 (6)	−0.0007 (5)	0.0013 (5)	−0.0021 (5)
C12	0.0229 (6)	0.0211 (6)	0.0248 (6)	0.0010 (5)	0.0023 (5)	−0.0004 (5)
C5	0.0231 (6)	0.0247 (7)	0.0230 (6)	0.0001 (5)	0.0067 (5)	−0.0013 (5)
C16	0.0240 (6)	0.0237 (7)	0.0252 (6)	−0.0021 (5)	0.0047 (5)	−0.0036 (5)
C15	0.0294 (7)	0.0306 (7)	0.0257 (7)	−0.0101 (6)	0.0025 (6)	−0.0053 (6)
C13	0.0215 (6)	0.0267 (7)	0.0315 (7)	0.0029 (5)	0.0041 (5)	0.0020 (6)
C7	0.0227 (6)	0.0274 (7)	0.0239 (6)	−0.0035 (5)	0.0029 (5)	−0.0044 (5)
C14	0.0196 (6)	0.0359 (8)	0.0274 (7)	−0.0068 (5)	−0.0004 (5)	0.0032 (6)
C8	0.0253 (7)	0.0340 (8)	0.0340 (8)	−0.0067 (6)	0.0127 (6)	−0.0073 (6)
O3	0.0236 (5)	0.0257 (5)	0.0188 (4)	−0.0011 (4)	−0.0005 (4)	−0.0013 (4)

N2—C10	1.3477 (18)	C4—C3	1.416 (2)
N2—N1	1.3872 (15)	C6—C5	1.4020 (19)
N2—H2A	0.87 (2)	C6—H6	0.9300
O2—C4	1.3624 (16)	C12—C13	1.3865 (19)
O2—C8	1.4250 (18)	C12—H12	0.9300
C10—O3	1.2344 (16)	C5—H5	0.9300
C10—C11	1.4983 (17)	C16—C15	1.3947 (19)
N1—C9	1.2826 (19)	C16—H16	0.9300
O1—C3	1.3695 (16)	C15—C14	1.387 (2)
O1—C7	1.4233 (17)	C15—H15	0.9300
C2—C3	1.3800 (18)	C13—C14	1.388 (2)
C2—C1	1.4098 (18)	C13—H13	0.9300
C2—H2	0.9300	C7—H7A	0.9600
C11—C16	1.3910 (19)	C7—H7B	0.9600
C11—C12	1.3927 (19)	C7—H7C	0.9600
C9—C1	1.4655 (18)	C14—H14	0.9300
C9—H9	0.957 (19)	C8—H8A	0.9600
C1—C6	1.385 (2)	C8—H8B	0.9600
C4—C5	1.3836 (19)	C8—H8C	0.9600
C10—N2—N1	119.69 (11)	C13—C12—C11	120.60 (13)
C10—N2—H2A	120.2 (13)	C13—C12—H12	119.7
N1—N2—H2A	119.9 (13)	C11—C12—H12	119.7
C4—O2—C8	117.13 (11)	C4—C5—C6	120.07 (13)
O3—C10—N2	123.54 (12)	C4—C5—H5	120.0
O3—C10—C11	120.99 (12)	C6—C5—H5	120.0
N2—C10—C11	115.41 (11)	C11—C16—C15	119.66 (13)
C9—N1—N2	114.77 (11)	C11—C16—H16	120.2
C3—O1—C7	115.95 (10)	C15—C16—H16	120.2
C3—C2—C1	120.30 (13)	C14—C15—C16	120.20 (14)
C3—C2—H2	119.9	C14—C15—H15	119.9
C1—C2—H2	119.9	C16—C15—H15	119.9
C16—C11—C12	119.70 (12)	C12—C13—C14	119.60 (14)
C16—C11—C10	123.28 (12)	C12—C13—H13	120.2
C12—C11—C10	117.00 (12)	C14—C13—H13	120.2
N1—C9—C1	121.22 (12)	O1—C7—H7A	109.5
N1—C9—H9	121.5 (11)	O1—C7—H7B	109.5
C1—C9—H9	117.2 (11)	H7A—C7—H7B	109.5
C6—C1—C2	119.33 (12)	O1—C7—H7C	109.5
C6—C1—C9	119.52 (12)	H7A—C7—H7C	109.5
C2—C1—C9	121.11 (12)	H7B—C7—H7C	109.5
O2—C4—C5	125.78 (13)	C15—C14—C13	120.23 (13)
O2—C4—C3	114.69 (12)	C15—C14—H14	119.9
C5—C4—C3	119.53 (12)	C13—C14—H14	119.9
O1—C3—C2	125.07 (13)	O2—C8—H8A	109.5
O1—C3—C4	114.84 (12)	O2—C8—H8B	109.5
C2—C3—C4	120.09 (12)	H8A—C8—H8B	109.5
C1—C6—C5	120.65 (13)	O2—C8—H8C	109.5
C1—C6—H6	119.7	H8A—C8—H8C	109.5
C5—C6—H6	119.7	H8B—C8—H8C	109.5
N1—N2—C10—O3	−0.8 (2)	O2—C4—C3—O1	2.59 (17)
N1—N2—C10—C11	−178.05 (11)	C5—C4—C3—O1	−177.78 (12)
C10—N2—N1—C9	175.87 (12)	O2—C4—C3—C2	−177.78 (13)
O3—C10—C11—C16	143.82 (14)	C5—C4—C3—C2	1.9 (2)
N2—C10—C11—C16	−38.82 (18)	C2—C1—C6—C5	0.5 (2)
O3—C10—C11—C12	−34.55 (18)	C9—C1—C6—C5	−177.44 (13)
N2—C10—C11—C12	142.80 (13)	C16—C11—C12—C13	1.5 (2)
N2—N1—C9—C1	−177.84 (12)	C10—C11—C12—C13	179.95 (12)
C3—C2—C1—C6	−0.8 (2)	O2—C4—C5—C6	177.36 (13)
C3—C2—C1—C9	177.03 (12)	C3—C4—C5—C6	−2.2 (2)
N1—C9—C1—C6	−177.81 (13)	C1—C6—C5—C4	1.1 (2)
N1—C9—C1—C2	4.3 (2)	C12—C11—C16—C15	−0.7 (2)
C8—O2—C4—C5	9.6 (2)	C10—C11—C16—C15	−179.04 (13)
C8—O2—C4—C3	−170.84 (13)	C11—C16—C15—C14	−0.6 (2)
C7—O1—C3—C2	2.7 (2)	C11—C12—C13—C14	−1.0 (2)
C7—O1—C3—C4	−177.68 (12)	C16—C15—C14—C13	1.2 (2)
C1—C2—C3—O1	179.27 (13)	C12—C13—C14—C15	−0.4 (2)
C1—C2—C3—C4	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O3i	0.957 (19)	2.455 (19)	3.2702 (18)	142.9 (15)
C7—H7B···O3ii	0.96	2.40	3.2434 (18)	146.
N2—H2A···O3i	0.87 (2)	2.07 (2)	2.9219 (16)	163.2 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O3i	0.957 (19)	2.455 (19)	3.2702 (18)	142.9 (15)
C7—H7B⋯O3ii	0.96	2.40	3.2434 (18)	146
N2—H2A⋯O3i	0.87 (2)	2.07 (2)	2.9219 (16)	163.2 (18)

Symmetry codes: (i) ; (ii) .