Methyl (E)-3,5-dimeth­oxy-2-{[2-(4-meth­oxy­benzo­yl)hydrazin-1-yl­idene]meth­yl}benzoate

Naz, H.; Taha, M.; Rahman, A.A.; Ismail, N.H.; Yousuf, S.

doi:10.1107/S1600536812034782

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2671

doi:10.1107/S1600536812034782

Open

access

Methyl (E)-3,5-dimethoxy-2-{[2-(4-methoxybenzoyl)hydrazin-1-ylidene]methyl}benzoate

Humera Naz,^a,^b Muhammad Taha,^a Aqilah Abd Rahman,^a,^b Nor Hadiani Ismail ^a and Sammer Yousuf ^c ^*

^aAtta-ur-Rahman Research Institute for Natural Products Discovery (RiND), Universiti Tecknologi MARA, Puncak Alam 42300, Selangor, Malaysia, ^bFaculty of Pharmacy, Universiti Tecknologi MARA, Puncak Alam 42300, Selangor, Malaysia, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 28 July 2012; accepted 6 August 2012; online 11 August 2012)

In the title compound, C₁₉H₂₀N₂O₆, the azomethine [C=N = 1.269 (2) Å] double bond adopts an E conformation and the dihedral angle between the planes of the benzene rings is 17.41 (11)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(16) loops. The dimers are connected by C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (100).

Related literature

For the biological activity of benzohydraazides, see: Khan et al. (2011 ); Chahan et al. (2006 ). For a related structure, see: Zhang (2009 ).

Experimental

Crystal data

C₁₉H₂₀N₂O₆
M_r = 372.37
Triclinic, $[P \overline 1]$
a = 8.8468 (7) Å
b = 10.7392 (8) Å
c = 10.9764 (8) Å
α = 113.377 (2)°
β = 90.656 (2)°
γ = 104.695 (2)°
V = 918.52 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.28 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.972, T_max = 0.989
10426 measured reflections
3415 independent reflections
2224 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.114
S = 1.02
3415 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.84 (2)	2.13 (2)	2.969 (2)	172.3 (19)
C18—H18B⋯N2ⁱⁱ	0.96	2.62	3.501 (3)	153
C19—H19B⋯O5ⁱⁱⁱ	0.96	2.57	3.511 (3)	168
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+2; (iii) x, y, z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034782/hb6920sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034782/hb6920Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034782/hb6920Isup3.cml

checkCIF report

Comment top

Phenyl hydrazones represent a very important class of bioactive organic compounds and are reported to have antibacterial, anticancer, antifungal, herbicidal activities, anticonvulsant, antiproliferative, antioxidant and antidiabetic activities (e.g. Khan et al., 2011; Chahan et al., 2006). The title compound was prepared as a part of our ongoing research to synthesize libraries of different bioactive benzohydrazone. The structure of title compound (Fig. 1) is similar to that of the previously published 4-Methoxy-N'-(2-methoxybenzylidene)-benzohydrazide (Zhang, 2009) with the difference that 2-methoxy benzne ring is replaced by 3,5-dimethoxybenzoate moiety (C9–C14). The azomethine (C=N,1.269 (2) Å) double bond adopt an E conformation (Fig. 1). The benzene rings (C1–C6 and C9–C14) subtend a dihedral angle 17.41 (11)° between them and maximum deviation of 0.014 (2) Å for C6 atom from the root mean square plane of 4-methoxybenzene ring (C1–C6).

The crystal structure features N1—H1A···O5, C18—H18B···N2 and C19—H19B···O5 intrmolecular hydrogen bonds and inked to form chains (symmetry codes as in Table 2) arranged parallel to (100) in (Fig. 2).

Related literature top

For the biological activity of benzohydraazides, see: Khan et al. (2011); Chahan et al. (2006). For a related structure, see: Zhang (2009).

Experimental top

A mixture of 2 mmol of each 4-methoxybenzohydrazide and methyl 2-formyl-3,5-dimethoxybenzoate and catalytical amount of acetic acid was refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the solvent was evaporated by vacuum to afford the crude product (0.610 g, yield 82%), which was re-crystallized from methanol solution to yield colourless blocks of the title compound.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal packing of the title compound I. Only hydrogen atoms involved in hydrogen bonding are shown.

Methyl (E)-3,5-dimethoxy-2-{[2-(4-methoxybenzoyl)hydrazin-1- ylidene]methyl}benzoate top

Crystal data top

C₁₉H₂₀N₂O₆	Z = 2
M_r = 372.37	F(000) = 392
Triclinic, P1	D_x = 1.346 Mg m⁻³
a = 8.8468 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7392 (8) Å	Cell parameters from 1645 reflections
c = 10.9764 (8) Å	θ = 2.0–25.5°
α = 113.377 (2)°	µ = 0.10 mm⁻¹
β = 90.656 (2)°	T = 298 K
γ = 104.695 (2)°	Block, colorless
V = 918.52 (12) Å³	0.28 × 0.14 × 0.11 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3415 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scan	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.972, T_max = 0.989	k = −13→13
10426 measured reflections	l = −13→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0494P)² + 0.0289P] where P = (F_o² + 2F_c²)/3
3415 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₉H₂₀N₂O₆	γ = 104.695 (2)°
M_r = 372.37	V = 918.52 (12) Å³
Triclinic, P1	Z = 2
a = 8.8468 (7) Å	Mo Kα radiation
b = 10.7392 (8) Å	µ = 0.10 mm⁻¹
c = 10.9764 (8) Å	T = 298 K
α = 113.377 (2)°	0.28 × 0.14 × 0.11 mm
β = 90.656 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3415 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2224 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.989	R_int = 0.033
10426 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.16 e Å⁻³
3415 reflections	Δρ_min = −0.17 e Å⁻³
252 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
O1	0.6563 (2)	0.64890 (18)	1.46257 (16)	0.0820 (5)
O2	0.24378 (19)	0.62729 (15)	0.97724 (16)	0.0730 (5)
O3	0.17303 (18)	1.25061 (14)	1.10340 (13)	0.0614 (4)
O4	0.0119 (2)	1.17046 (16)	0.65074 (14)	0.0691 (5)
O5	0.40868 (17)	0.87627 (14)	0.73902 (14)	0.0564 (4)
O6	0.16475 (16)	0.73913 (14)	0.65091 (13)	0.0549 (4)
N1	0.3446 (2)	0.86420 (19)	1.08462 (18)	0.0507 (5)
N2	0.26850 (18)	0.88947 (17)	0.98968 (16)	0.0477 (4)
C1	0.4660 (3)	0.8228 (2)	1.3057 (2)	0.0636 (6)
H1B	0.4472	0.9098	1.3257	0.076*
C2	0.5451 (3)	0.8037 (2)	1.4035 (2)	0.0631 (6)
H2B	0.5770	0.8766	1.4884	0.076*
C3	0.5760 (2)	0.6779 (2)	1.3750 (2)	0.0537 (5)
C4	0.5221 (3)	0.5694 (2)	1.2506 (2)	0.0721 (7)
H4A	0.5402	0.4823	1.2311	0.087*
C5	0.4413 (3)	0.5890 (2)	1.1549 (2)	0.0603 (6)
H5A	0.4043	0.5142	1.0717	0.072*
C6	0.4143 (2)	0.7167 (2)	1.17971 (19)	0.0448 (5)
C7	0.3274 (2)	0.7306 (2)	1.0710 (2)	0.0488 (5)
C8	0.2808 (2)	1.0184 (2)	1.01728 (19)	0.0475 (5)
H8A	0.3342	1.0878	1.0990	0.057*
C9	0.2117 (2)	1.05887 (19)	0.92205 (18)	0.0410 (5)
C10	0.1566 (2)	1.17821 (19)	0.96804 (18)	0.0434 (5)
C11	0.0895 (2)	1.2190 (2)	0.88060 (19)	0.0491 (5)
H11A	0.0554	1.3001	0.9129	0.059*
C12	0.0739 (2)	1.1378 (2)	0.74496 (19)	0.0480 (5)
C13	0.1234 (2)	1.0168 (2)	0.69618 (19)	0.0493 (5)
H13A	0.1094	0.9611	0.6047	0.059*
C14	0.1937 (2)	0.97907 (19)	0.78374 (18)	0.0419 (5)
C15	0.2684 (3)	0.8614 (2)	0.72612 (18)	0.0442 (5)
C16	0.2293 (3)	0.6196 (2)	0.5973 (3)	0.0761 (7)
H16A	0.1461	0.5353	0.5470	0.114*
H16B	0.2788	0.6089	0.6694	0.114*
H16C	0.3058	0.6353	0.5398	0.114*
C17	−0.0109 (3)	1.3070 (2)	0.6920 (2)	0.0695 (7)
H17A	−0.0380	1.3215	0.6146	0.104*
H17B	0.0844	1.3775	0.7420	0.104*
H17C	−0.0945	1.3142	0.7471	0.104*
C18	0.0967 (3)	1.3593 (2)	1.1573 (2)	0.0617 (6)
H18A	0.1147	1.3988	1.2532	0.093*
H18B	−0.0145	1.3203	1.1282	0.093*
H18C	0.1383	1.4320	1.1268	0.093*
C19	0.7245 (3)	0.7605 (3)	1.5882 (3)	0.0943 (9)
H19A	0.7883	0.7292	1.6350	0.141*
H19B	0.6425	0.7883	1.6400	0.141*
H19C	0.7888	0.8396	1.5750	0.141*
H1A	0.412 (2)	0.936 (2)	1.141 (2)	0.054 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1044 (13)	0.1002 (13)	0.0638 (11)	0.0587 (11)	−0.0016 (10)	0.0388 (10)
O2	0.0884 (12)	0.0517 (9)	0.0698 (11)	0.0157 (9)	−0.0233 (9)	0.0191 (8)
O3	0.0889 (11)	0.0613 (9)	0.0364 (8)	0.0409 (8)	−0.0007 (7)	0.0109 (7)
O4	0.1052 (12)	0.0728 (10)	0.0478 (9)	0.0528 (9)	0.0012 (8)	0.0271 (8)
O5	0.0507 (9)	0.0559 (9)	0.0602 (9)	0.0234 (7)	0.0022 (7)	0.0164 (7)
O6	0.0585 (9)	0.0437 (8)	0.0583 (9)	0.0197 (7)	−0.0020 (7)	0.0138 (7)
N1	0.0596 (12)	0.0468 (11)	0.0467 (11)	0.0137 (10)	−0.0095 (9)	0.0216 (9)
N2	0.0520 (10)	0.0511 (11)	0.0444 (10)	0.0180 (8)	−0.0025 (8)	0.0225 (8)
C1	0.0948 (18)	0.0525 (13)	0.0532 (14)	0.0362 (13)	0.0017 (13)	0.0225 (11)
C2	0.0890 (17)	0.0623 (15)	0.0427 (13)	0.0324 (13)	0.0019 (12)	0.0200 (11)
C3	0.0572 (13)	0.0682 (15)	0.0521 (13)	0.0309 (12)	0.0097 (11)	0.0333 (12)
C4	0.0968 (19)	0.0615 (15)	0.0710 (17)	0.0434 (14)	−0.0009 (15)	0.0279 (13)
C5	0.0732 (15)	0.0511 (13)	0.0551 (14)	0.0251 (12)	−0.0022 (12)	0.0162 (11)
C6	0.0472 (12)	0.0476 (12)	0.0461 (12)	0.0172 (10)	0.0074 (10)	0.0235 (10)
C7	0.0529 (13)	0.0457 (13)	0.0476 (12)	0.0164 (11)	0.0014 (10)	0.0177 (10)
C8	0.0559 (13)	0.0474 (12)	0.0402 (11)	0.0182 (10)	−0.0031 (9)	0.0171 (9)
C9	0.0432 (11)	0.0439 (11)	0.0380 (11)	0.0144 (9)	−0.0002 (9)	0.0180 (9)
C10	0.0508 (12)	0.0436 (11)	0.0360 (11)	0.0180 (10)	0.0012 (9)	0.0138 (9)
C11	0.0607 (13)	0.0476 (12)	0.0467 (12)	0.0279 (10)	0.0057 (10)	0.0197 (10)
C12	0.0583 (13)	0.0541 (13)	0.0407 (12)	0.0250 (10)	0.0026 (10)	0.0233 (10)
C13	0.0610 (13)	0.0531 (13)	0.0361 (11)	0.0259 (11)	0.0017 (10)	0.0149 (9)
C14	0.0460 (11)	0.0426 (11)	0.0410 (11)	0.0179 (9)	0.0034 (9)	0.0178 (9)
C15	0.0536 (13)	0.0476 (12)	0.0347 (11)	0.0175 (11)	0.0005 (10)	0.0184 (9)
C16	0.0824 (17)	0.0435 (13)	0.0919 (18)	0.0268 (12)	0.0028 (15)	0.0121 (12)
C17	0.0943 (18)	0.0737 (16)	0.0675 (16)	0.0477 (14)	0.0140 (14)	0.0416 (13)
C18	0.0781 (16)	0.0566 (14)	0.0459 (13)	0.0327 (12)	0.0067 (11)	0.0082 (10)
C19	0.106 (2)	0.133 (3)	0.0602 (17)	0.065 (2)	−0.0023 (16)	0.0375 (17)

Geometric parameters (Å, º) top

O1—C3	1.364 (2)	C6—C7	1.488 (3)
O1—C19	1.416 (3)	C8—C9	1.461 (2)
O2—C7	1.224 (2)	C8—H8A	0.9300
O3—C10	1.362 (2)	C9—C10	1.394 (2)
O3—C18	1.425 (2)	C9—C14	1.399 (3)
O4—C12	1.366 (2)	C10—C11	1.385 (2)
O4—C17	1.422 (2)	C11—C12	1.378 (3)
O5—C15	1.209 (2)	C11—H11A	0.9300
O6—C15	1.326 (2)	C12—C13	1.382 (3)
O6—C16	1.450 (2)	C13—C14	1.377 (2)
N1—C7	1.350 (2)	C13—H13A	0.9300
N1—N2	1.383 (2)	C14—C15	1.494 (3)
N1—H1A	0.85 (2)	C16—H16A	0.9600
N2—C8	1.269 (2)	C16—H16B	0.9600
C1—C6	1.375 (3)	C16—H16C	0.9600
C1—C2	1.384 (3)	C17—H17A	0.9600
C1—H1B	0.9300	C17—H17B	0.9600
C2—C3	1.361 (3)	C17—H17C	0.9600
C2—H2B	0.9300	C18—H18A	0.9600
C3—C4	1.375 (3)	C18—H18B	0.9600
C4—C5	1.376 (3)	C18—H18C	0.9600
C4—H4A	0.9300	C19—H19A	0.9600
C5—C6	1.373 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600

C3—O1—C19	118.05 (19)	C12—C11—H11A	120.5
C10—O3—C18	118.26 (15)	C10—C11—H11A	120.5
C12—O4—C17	118.22 (16)	O4—C12—C11	123.46 (18)
C15—O6—C16	114.98 (16)	O4—C12—C13	115.72 (17)
C7—N1—N2	120.43 (18)	C11—C12—C13	120.82 (17)
C7—N1—H1A	124.2 (14)	C14—C13—C12	119.67 (18)
N2—N1—H1A	114.6 (14)	C14—C13—H13A	120.2
C8—N2—N1	115.63 (17)	C12—C13—H13A	120.2
C6—C1—C2	121.78 (19)	C13—C14—C9	121.17 (17)
C6—C1—H1B	119.1	C13—C14—C15	117.78 (17)
C2—C1—H1B	119.1	C9—C14—C15	120.59 (16)
C3—C2—C1	119.8 (2)	O5—C15—O6	123.04 (18)
C3—C2—H2B	120.1	O5—C15—C14	124.35 (18)
C1—C2—H2B	120.1	O6—C15—C14	112.46 (17)
C2—C3—O1	124.7 (2)	O6—C16—H16A	109.5
C2—C3—C4	119.3 (2)	O6—C16—H16B	109.5
O1—C3—C4	116.04 (19)	H16A—C16—H16B	109.5
C3—C4—C5	120.3 (2)	O6—C16—H16C	109.5
C3—C4—H4A	119.8	H16A—C16—H16C	109.5
C5—C4—H4A	119.8	H16B—C16—H16C	109.5
C6—C5—C4	121.4 (2)	O4—C17—H17A	109.5
C6—C5—H5A	119.3	O4—C17—H17B	109.5
C4—C5—H5A	119.3	H17A—C17—H17B	109.5
C5—C6—C1	117.35 (19)	O4—C17—H17C	109.5
C5—C6—C7	118.43 (18)	H17A—C17—H17C	109.5
C1—C6—C7	124.20 (18)	H17B—C17—H17C	109.5
O2—C7—N1	122.64 (19)	O3—C18—H18A	109.5
O2—C7—C6	121.79 (18)	O3—C18—H18B	109.5
N1—C7—C6	115.55 (18)	H18A—C18—H18B	109.5
N2—C8—C9	120.71 (18)	O3—C18—H18C	109.5
N2—C8—H8A	119.6	H18A—C18—H18C	109.5
C9—C8—H8A	119.6	H18B—C18—H18C	109.5
C10—C9—C14	117.63 (16)	O1—C19—H19A	109.5
C10—C9—C8	120.10 (17)	O1—C19—H19B	109.5
C14—C9—C8	122.24 (17)	H19A—C19—H19B	109.5
O3—C10—C11	122.77 (17)	O1—C19—H19C	109.5
O3—C10—C9	115.61 (16)	H19A—C19—H19C	109.5
C11—C10—C9	121.61 (17)	H19B—C19—H19C	109.5
C12—C11—C10	119.05 (18)

C7—N1—N2—C8	174.00 (18)	C14—C9—C10—O3	178.40 (17)
C6—C1—C2—C3	1.2 (4)	C8—C9—C10—O3	0.3 (3)
C1—C2—C3—O1	178.3 (2)	C14—C9—C10—C11	−1.4 (3)
C1—C2—C3—C4	−2.7 (3)	C8—C9—C10—C11	−179.51 (18)
C19—O1—C3—C2	−5.8 (3)	O3—C10—C11—C12	−178.44 (18)
C19—O1—C3—C4	175.3 (2)	C9—C10—C11—C12	1.4 (3)
C2—C3—C4—C5	1.7 (4)	C17—O4—C12—C11	11.9 (3)
O1—C3—C4—C5	−179.3 (2)	C17—O4—C12—C13	−167.25 (19)
C3—C4—C5—C6	0.9 (4)	C10—C11—C12—O4	−178.79 (19)
C4—C5—C6—C1	−2.4 (3)	C10—C11—C12—C13	0.4 (3)
C4—C5—C6—C7	179.4 (2)	O4—C12—C13—C14	177.21 (18)
C2—C1—C6—C5	1.4 (3)	C11—C12—C13—C14	−2.0 (3)
C2—C1—C6—C7	179.4 (2)	C12—C13—C14—C9	1.9 (3)
N2—N1—C7—O2	−1.1 (3)	C12—C13—C14—C15	−170.38 (18)
N2—N1—C7—C6	−179.71 (16)	C10—C9—C14—C13	−0.2 (3)
C5—C6—C7—O2	20.4 (3)	C8—C9—C14—C13	177.79 (18)
C1—C6—C7—O2	−157.6 (2)	C10—C9—C14—C15	171.85 (18)
C5—C6—C7—N1	−160.94 (19)	C8—C9—C14—C15	−10.1 (3)
C1—C6—C7—N1	21.0 (3)	C16—O6—C15—O5	7.0 (3)
N1—N2—C8—C9	177.12 (17)	C16—O6—C15—C14	−177.25 (18)
N2—C8—C9—C10	148.9 (2)	C13—C14—C15—O5	111.9 (2)
N2—C8—C9—C14	−29.1 (3)	C9—C14—C15—O5	−60.4 (3)
C18—O3—C10—C11	9.9 (3)	C13—C14—C15—O6	−63.8 (2)
C18—O3—C10—C9	−169.98 (18)	C9—C14—C15—O6	123.87 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.84 (2)	2.13 (2)	2.969 (2)	172.3 (19)
C18—H18B···N2ⁱⁱ	0.96	2.62	3.501 (3)	153
C19—H19B···O5ⁱⁱⁱ	0.96	2.57	3.511 (3)	168

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₂O₆
M_r	372.37
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.8468 (7), 10.7392 (8), 10.9764 (8)
α, β, γ (°)	113.377 (2), 90.656 (2), 104.695 (2)
V (Å³)	918.52 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.14 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.972, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	10426, 3415, 2224
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.114, 1.02
No. of reflections	3415
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.84 (2)	2.13 (2)	2.969 (2)	172.3 (19)
C18—H18B···N2ⁱⁱ	0.96	2.62	3.501 (3)	153
C19—H19B···O5ⁱⁱⁱ	0.96	2.57	3.511 (3)	168

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

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chahan, Z. H., Arif, M., Shafiq, Z., Yaqub, M. & Supuran, C. T. (2006). J. Enzyme Inhib. Med Chem., 21, 95–103. Web of Science PubMed Google Scholar
Khan, K. M., Shah, Z., Ahmad, V. U., Muhammad, K., Taha, M., Rahim, F., Jahun, H., Perveen, S. & Choudhary, M. I. (2011). Med. Chem. 7, 572–580. Web of Science CAS PubMed Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X. (2009). Acta Cryst. E65, o1388. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2671

doi:10.1107/S1600536812034782

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl (E)-3,5-dimeth­­oxy-2-{[2-(4-meth­­oxy­benzo­yl)hydrazin-1-yl­­idene]meth­yl}benzoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Methyl (E)-3,5-dimethoxy-2-{[2-(4-methoxybenzoyl)hydrazin-1-ylidene]methyl}benzoate