N′-(3,4-Dimeth­oxy­benzyl­idene)benzo­hydrazide

Hashemian, S.; Ghaeinee, V.; Notash, B.

doi:10.1107/S1600536810052128

organic compounds

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Volume 67| Part 1| January 2011| Page o171

https://doi.org/10.1107/S1600536810052128

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N′-(3,4-Dimethoxybenzylidene)benzohydrazide

Saeedeh Hashemian,^a ^* Vahideh Ghaeinee ^a and Behrouz Notash ^b

^aDepartment of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G.C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: sa_hashemian@yahoo.com

(Received 9 December 2010; accepted 12 December 2010; online 18 December 2010)

The crystal structure of the title Schiff base compound, C₁₆H₁₆N₂O₃, is characterized by chains of molecules linked by intermolecular 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_r = 284.31
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.131
S = 1.03
3758 reflections
200 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052128/bt5434Isup2.hkl

checkCIF report

Comment top

Schiff bases are important organic compounds. Metal complexes based on Schiff bases have received considerable attention because they can be utilized as a model of active centers in various complexes (Tamboura et al., 2009; Das & Pal, 2004).

We report here the crystal structure of N'-(3,4-dimethoxybenzylidene)-benzohydrazide. The title compound was synthesized from the reaction of 3,4-dimethoxy benzaldehyde and benzoylhydrazine in methanol. The asymmetric unit of the title compound is shown in Fig. 1. The bond lengths and angles are comparable to those observed for N'-(2,4-dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide (Alhadi et al., 2009) and N'-(3,4-dimethoxybenzylidene)acetohydrazide (Zhou et al., 2009). The crystal structure is characterized by chains of running along the c-axis. The molecules in a chain are linked by intermolecular N—H···O hydrogen bonds. Further stabilization is provided by weak C—H···O contacts.

Related literature top

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

Experimental top

To a methanol solution (20 ml) of benzoylhydrazine (1.0 mmol, 0.135 g), 3,4-dimethoxybenzaldehyde (1.0 mmol, 0.165 g), a few drops of acetic acid were added. The mixture was refluxed for 6 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and finally dried in air (m.p: 181–183 °C, yield: 81%). Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature.

Structure description top

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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. The molecular structure of N'-(3,4-dimethoxybenzylidene)benzohydrazide with displacement ellipsoids drawn at 50% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the a axis. The intermolecular N—H···O and C—H···O hydrogen bonds are shown as green dashed lines.

N'-(3,4-Dimethoxybenzylidene)benzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₃	F(000) = 600
M_r = 284.31	D_x = 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

Data collection top

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

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)] = 0.050	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(F_o²) + (0.068P)² + 0.4464P] where P = (F_o² + 2F_c²)/3
3758 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₃	V = 1402.3 (5) Å³
M_r = 284.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.612 (3) Å	µ = 0.09 mm⁻¹
b = 11.291 (2) Å	T = 120 K
c = 9.892 (2) Å	0.5 × 0.4 × 0.15 mm
β = 95.46 (3)°

Data collection top

Stoe IPDS II diffractometer	3758 independent reflections
Absorption correction: numerical shape of crystal determined optically	3054 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.984	R_int = 0.052
9840 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.36 e Å⁻³
3758 reflections	Δρ_min = −0.24 e Å⁻³
200 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₃
M_r	284.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	12.612 (3), 11.291 (2), 9.892 (2)
β (°)	95.46 (3)
V (Å³)	1402.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.5 × 0.4 × 0.15

Data collection
Diffractometer	Stoe IPDS II
Absorption correction	Numerical shape of crystal determined optically
T_min, T_max	0.954, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9840, 3758, 3054
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.131, 1.03
No. of reflections	3758
No. of parameters	200
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.24

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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)	146.2
N2—H2A···O3ⁱ	0.87 (2)	2.07 (2)	2.9219 (16)	163.2 (18)

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

Acknowledgements

We are grateful to the Islamic Azad University, Yazd Branch, for financial support.

References

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