(E)-4-Meth­oxy-N′-(3,4,5-trimeth­oxy­benzyl­idene)benzohydrazide

Fun, H.-K.; Promdet, P.; Horkaew, J.; Chantrapromma, S.

doi:10.1107/S1600536812003534

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o562-o563

doi:10.1107/S1600536812003534

Open

access

(E)-4-Methoxy-N′-(3,4,5-trimethoxybenzylidene)benzohydrazide

Hoong-Kun Fun,^a ^*‡ Premrudee Promdet,^b Jirapa Horkaew ^b and Suchada Chantrapromma ^b §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 20 January 2012; accepted 26 January 2012; online 4 February 2012)

In the asymmetric unit of the title compound, C₁₈H₂₀N₂O₅, there are two crystallographic independent molecules. Both molecules are twisted; the dihedral angle between the two benzene rings is 7.2 (5)° in one molecule, whereas it is 85.9 (4)° in the other. Of the three methoxy groups in the 3,4,5-trimethoxyphenyl unit, two methoxy groups at meta positions are approximately coplanar with the benzene plane [C—O—C—C torsion angles of −2.3 (13)–4.8 (11)°], but the other methoxy, at the para position, is out of the plane [C—O—C—C of 72.8 (9)° in one molecule and −77.5 (9)° in the other]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds and weak C—H⋯O interactions into tapes along the b axis. C—H⋯π interactions are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Fun et al. (2011 ); Horkaew et al. (2011 ); Promdet et al. (2011 ). For background and applications of benzohydrazide derivatives, see: Angelusiu et al. (2010 ); Bedia et al. (2006 ); Loncle et al. (2004 ); Melnyk et al. (2006 ); Raj et al. (2007 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₅
M_r = 344.36
Monoclinic, P 2₁
a = 13.3344 (17) Å
b = 5.0484 (6) Å
c = 25.767 (3) Å
β = 98.250 (2)°
V = 1716.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 297 K
0.26 × 0.25 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.975, T_max = 0.990
12488 measured reflections
3361 independent reflections
2671 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.090
wR(F²) = 0.275
S = 1.05
3361 reflections
453 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9A–C14A and C9B–C14B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1Aⁱ	0.86	2.11	2.944 (13)	164
N1B—H1NB⋯O1Bⁱ	0.85	2.21	2.939 (9)	144
C8B—H8B⋯O1Bⁱ	0.93	2.52	3.287 (11)	140
C15B—H15D⋯O2Aⁱⁱ	0.96	2.60	3.498 (14)	156
C17B—H17D⋯O4Bⁱⁱⁱ	0.96	2.60	3.420 (10)	144
C16A—H16B⋯Cg1^iv	0.96	2.66	3.429 (10)	138
C16B—H16F⋯Cg2^iv	0.96	2.77	3.697 (10)	162
C18A—H18B⋯Cg1ⁱ	0.96	2.85	3.739 (10)	155
C18B—H18F⋯Cg2ⁱ	0.96	2.74	3.583 (10)	146
Symmetry codes: (i) x, y+1, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003534/is5059sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003534/is5059Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003534/is5059Isup3.cml

checkCIF report

Comment top

Benzohydrazide derivatives obtained from the reaction of aldehyde with hydrazine have been demonstrated to possess excellent biological properties such as antibacterial (Angelusiu et al., 2010) antifungal (Loncle et al., 2004), antimalarial (Melnyk et al., 2006) and antiproliferative (Raj et al., 2007) activities. The title benzohydrazide (I) is the condensation product of 4-methoxybenzohydrazide and 3,4,5-trimethoxybenzaldehyde which was synthesized in order to study and compare its biological properties with other related compounds (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011). (I) was screened for antioxidant activities and found to be inactive.

The title compound (Fig. 1) crystallized out with two crystallographically independent molecules A and B per asymmetric unit with the two molecules having slight differences in bond angles. The molecule exists in a trans-configuration with respect to the C8═N2 bond [1.243 (12) Å in molecule A and 1.290 (11) Å in molecule B] and the torsion angle N1–N2–C8–C9 = -174.4 (7)° for molecule A [-172.2 (6)° for molecule B]. Molecule A is less twisted than molecule B which is indicated by the dihedral angle between the two benzene rings being 7.2 (5)° in molecule A whereas it is 85.9 (4)° in molecule B. The middle bridge fragment (O1/C7/N1/N2/C8) of molecule A is also less twisted than that of molecule B with the dihedral angle between the mean planes of O1/C7/N1 and N1/N2/C8 being 8.3 (15)° in molecule A whereas it is 26.0 (11)° in molecule B. The methoxy group of 4-methoxyphenyl (at atom C4) is co-planar with its bound benzene ring [torsion angle C15–O2–C4–C5 = 1.16 (18)° and the r.m.s 0.0222 (9) Å in molecule A [-4.3 (15)° and r.m.s 0.0164 (9) Å in molecule B] for the eight non-H atoms. The three methoxy substituents of 3,4,5-trimethoxyphenyl unit have two different orientations in which the two methoxy groups at two meta-positions or at atoms C11 and C13 are co-planar with torsion angles C16–O3–C11–C10 = 4.8 (11)° and C18–O5–C13–C12 = 178.5 (7)°, whereas the third one at the para-position or at atom C12 is tilted out of plane with the torsion angle C17–O4–C12–C11 = 72.8 (9)° [the corresponding values are -2.3, 179.2 (8) and -77.5 (9)°, respectively, in molecule B]. Bond distances are of normal values (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011). In the crystal packing (Fig. 2), the molecules are linked by N—H···O hydrogen bonds and weak C—H···O interactions (Table 1) into tapes along the b axis. C—H···π weak interactions were presented (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2011); Horkaew et al. (2011); Promdet et al. (2011). For background and applications to benzohydrazide derivatives, see: Angelusiu et al. (2010); Bedia et al. (2006); Loncle et al. (2004); Melnyk et al. (2006); Raj et al. (2007).

Experimental top

The title compound (I) was prepared by dissolving 4-methoxybenzohydrazide (2 mmol, 0.30 g) in ethanol (10 ml). The solution of 3,4,5-trimethoxybenzaldehyde (2 mmol, 0.40 g) in ethanol (10 ml) was then added slowly to the reaction. The mixture was refluxed for around 6 hr. The solution was then cooled to room temperature and evaporated by reduced pressure. Colorless block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from methanol by slow evaporation of the solvent at room temperature after several days (m.p. 464-465 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed along the a axis, showing tapes running along the b axis. Hydrogen bonds were drawn as dashed lines.

(E)-4-Methoxy-N'-(3,4,5-trimethoxybenzylidene)benzohydrazide top

Crystal data top

C₁₈H₂₀N₂O₅	F(000) = 728
M_r = 344.36	D_x = 1.332 Mg m⁻³
Monoclinic, P2₁	Melting point = 464–465 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 13.3344 (17) Å	Cell parameters from 3361 reflections
b = 5.0484 (6) Å	θ = 1.6–25.0°
c = 25.767 (3) Å	µ = 0.10 mm⁻¹
β = 98.250 (2)°	T = 297 K
V = 1716.6 (4) Å³	Block, colorless
Z = 4	0.26 × 0.25 × 0.11 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3361 independent reflections
Radiation source: fine-focus sealed tube	2671 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.0°, θ_min = 1.6°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
T_min = 0.975, T_max = 0.990	l = −30→30
12488 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)] = 0.090	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.275	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1357P)² + 4.5571P] where P = (F_o² + 2F_c²)/3
3361 reflections	(Δ/σ)_max = 0.001
453 parameters	Δρ_max = 0.75 e Å⁻³
1 restraint	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₅	V = 1716.6 (4) Å³
M_r = 344.36	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 13.3344 (17) Å	µ = 0.10 mm⁻¹
b = 5.0484 (6) Å	T = 297 K
c = 25.767 (3) Å	0.26 × 0.25 × 0.11 mm
β = 98.250 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3361 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2671 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.990	R_int = 0.039
12488 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.090	1 restraint
wR(F²) = 0.275	H-atom parameters constrained
S = 1.05	Δρ_max = 0.75 e Å⁻³
3361 reflections	Δρ_min = −0.47 e Å⁻³
453 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1A	0.3343 (7)	−0.3991 (18)	0.6742 (3)	0.078 (2)
O2A	0.6531 (5)	0.112 (2)	0.5437 (3)	0.080 (3)
O3A	−0.0197 (4)	−0.2248 (13)	0.8547 (2)	0.0443 (14)
O4A	0.0405 (4)	0.0695 (13)	0.93724 (19)	0.0450 (14)
O5A	0.1905 (4)	0.4311 (15)	0.9377 (2)	0.0543 (17)
N1A	0.3208 (5)	0.0316 (19)	0.6969 (3)	0.055 (2)
H1NA	0.3373	0.1922	0.6909	0.066*
N2A	0.2568 (5)	−0.0252 (18)	0.7341 (3)	0.053 (2)
C1A	0.4361 (7)	−0.083 (2)	0.6382 (3)	0.053 (2)
C2A	0.4404 (8)	−0.243 (4)	0.5919 (4)	0.101 (4)
H2A	0.4008	−0.3925	0.5830	0.121*
C3A	0.5149 (8)	−0.139 (4)	0.5609 (4)	0.101 (4)
H3A	0.5156	−0.2111	0.5278	0.121*
C4A	0.5852 (6)	0.060 (3)	0.5768 (3)	0.063 (3)
C5A	0.5800 (7)	0.192 (3)	0.6231 (3)	0.065 (3)
H5A	0.6257	0.3269	0.6340	0.078*
C6A	0.5070 (7)	0.123 (3)	0.6530 (4)	0.077 (4)
H6A	0.5037	0.2148	0.6841	0.093*
C7A	0.3549 (8)	−0.1670 (18)	0.6713 (4)	0.054 (2)
C8A	0.2406 (7)	0.1708 (19)	0.7608 (3)	0.045 (2)
H8AA	0.2653	0.3358	0.7528	0.054*
C9A	0.1820 (6)	0.1442 (17)	0.8058 (3)	0.0377 (19)
C10A	0.1069 (5)	−0.0388 (17)	0.8060 (3)	0.0376 (18)
H10A	0.0892	−0.1480	0.7771	0.045*
C11A	0.0568 (5)	−0.0620 (15)	0.8494 (3)	0.0321 (16)
C12A	0.0869 (6)	0.1012 (18)	0.8933 (3)	0.0373 (18)
C13A	0.1640 (5)	0.2884 (17)	0.8925 (3)	0.0337 (17)
C14A	0.2105 (5)	0.3152 (17)	0.8482 (3)	0.0364 (18)
H14A	0.2597	0.4442	0.8466	0.044*
C15A	0.7253 (8)	0.309 (3)	0.5574 (4)	0.086 (4)
H15C	0.7754	0.3023	0.5342	0.129*
H15B	0.7573	0.2815	0.5928	0.129*
H15A	0.6929	0.4796	0.5547	0.129*
C16A	−0.0507 (6)	−0.413 (2)	0.8128 (3)	0.048 (2)
H16C	−0.0986	−0.5353	0.8237	0.072*
H16B	0.0075	−0.5075	0.8048	0.072*
H16A	−0.0817	−0.3192	0.7822	0.072*
C17A	−0.0268 (7)	0.284 (2)	0.9456 (4)	0.058 (3)
H17C	−0.0591	0.2464	0.9758	0.088*
H17B	−0.0775	0.3028	0.9153	0.088*
H17A	0.0112	0.4454	0.9512	0.088*
C18A	0.2695 (6)	0.619 (2)	0.9396 (4)	0.056 (3)
H18C	0.2762	0.7116	0.9724	0.085*
H18B	0.2542	0.7425	0.9113	0.085*
H18A	0.3319	0.5292	0.9364	0.085*
O1B	0.8368 (6)	−0.3520 (12)	0.6791 (3)	0.064 (2)
O2B	1.1551 (5)	0.082 (2)	0.5408 (2)	0.071 (2)
O3B	0.6942 (4)	−0.0861 (15)	0.9327 (2)	0.0526 (16)
O4B	0.5447 (4)	0.2633 (13)	0.93709 (19)	0.0432 (14)
O5B	0.4755 (4)	0.5755 (13)	0.8561 (2)	0.0453 (14)
N1B	0.8346 (5)	0.0774 (14)	0.7016 (2)	0.0397 (15)
H1NB	0.8270	0.2117	0.6812	0.048*
N2B	0.7795 (5)	0.0341 (15)	0.7419 (2)	0.0402 (16)
C1B	0.9427 (6)	−0.0541 (16)	0.6400 (3)	0.0367 (17)
C2B	0.9451 (7)	−0.1879 (19)	0.5939 (3)	0.051 (2)
H2B	0.8949	−0.3130	0.5839	0.061*
C3B	1.0160 (7)	−0.149 (2)	0.5623 (3)	0.053 (2)
H3B	1.0173	−0.2531	0.5326	0.064*
C4B	1.0878 (6)	0.052 (2)	0.5750 (3)	0.052 (2)
C5B	1.0874 (6)	0.195 (2)	0.6201 (3)	0.048 (2)
H5B	1.1358	0.3256	0.6293	0.058*
C6B	1.0139 (6)	0.143 (2)	0.6523 (3)	0.047 (2)
H6B	1.0129	0.2431	0.6825	0.056*
C7B	0.8691 (7)	−0.1257 (18)	0.6757 (3)	0.045 (2)
C8B	0.7321 (5)	0.241 (2)	0.7552 (3)	0.0399 (19)
H8B	0.7299	0.3951	0.7354	0.048*
C9B	0.6815 (5)	0.2261 (18)	0.8023 (3)	0.0395 (19)
C10B	0.7130 (5)	0.061 (2)	0.8438 (3)	0.0406 (19)
H10B	0.7669	−0.0535	0.8417	0.049*
C11B	0.6668 (5)	0.0605 (19)	0.8886 (3)	0.0392 (18)
C12B	0.5874 (5)	0.2440 (18)	0.8921 (3)	0.0340 (17)
C13B	0.5554 (5)	0.4060 (18)	0.8500 (3)	0.0348 (17)
C14B	0.6028 (5)	0.4086 (19)	0.8057 (3)	0.0399 (19)
H14B	0.5832	0.5282	0.7787	0.048*
C15B	1.2275 (8)	0.293 (3)	0.5513 (4)	0.086 (4)
H15D	1.2581	0.3281	0.5204	0.129*
H15E	1.2790	0.2425	0.5795	0.129*
H15F	1.1939	0.4499	0.5609	0.129*
C16B	0.7757 (6)	−0.263 (2)	0.9328 (4)	0.052 (2)
H16D	0.7973	−0.3246	0.9679	0.078*
H16E	0.8309	−0.1749	0.9199	0.078*
H16F	0.7544	−0.4118	0.9106	0.078*
C17B	0.4744 (7)	0.062 (2)	0.9456 (3)	0.059 (3)
H17D	0.4641	0.0629	0.9817	0.088*
H17E	0.5006	−0.1078	0.9372	0.088*
H17F	0.4111	0.0932	0.9237	0.088*
C18B	0.4404 (6)	0.746 (2)	0.8154 (3)	0.050 (2)
H18D	0.3865	0.8527	0.8252	0.075*
H18E	0.4158	0.6453	0.7846	0.075*
H18F	0.4947	0.8590	0.8082	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.111 (6)	0.058 (5)	0.076 (5)	−0.016 (5)	0.054 (4)	−0.001 (4)
O2A	0.064 (4)	0.122 (8)	0.058 (4)	−0.021 (5)	0.028 (3)	−0.003 (5)
O3A	0.047 (3)	0.042 (3)	0.046 (3)	−0.009 (3)	0.014 (3)	−0.004 (3)
O4A	0.060 (3)	0.045 (3)	0.036 (3)	0.007 (3)	0.023 (2)	0.011 (3)
O5A	0.058 (3)	0.061 (4)	0.045 (3)	−0.017 (4)	0.010 (3)	−0.010 (3)
N1A	0.055 (4)	0.064 (5)	0.053 (4)	−0.006 (4)	0.028 (3)	0.007 (4)
N2A	0.052 (4)	0.061 (6)	0.048 (4)	−0.005 (4)	0.017 (3)	−0.001 (4)
C1A	0.056 (5)	0.058 (6)	0.047 (5)	−0.007 (5)	0.017 (4)	−0.003 (5)
C2A	0.076 (5)	0.179 (12)	0.052 (4)	−0.006 (7)	0.025 (4)	−0.037 (7)
C3A	0.076 (5)	0.179 (12)	0.052 (4)	−0.006 (7)	0.025 (4)	−0.037 (7)
C4A	0.043 (4)	0.101 (9)	0.047 (5)	−0.002 (6)	0.009 (4)	−0.002 (6)
C5A	0.055 (5)	0.095 (9)	0.049 (5)	−0.002 (6)	0.015 (4)	−0.013 (6)
C6A	0.059 (6)	0.128 (12)	0.047 (5)	−0.001 (7)	0.014 (5)	−0.014 (7)
C7A	0.070 (6)	0.029 (5)	0.061 (5)	0.017 (5)	0.006 (5)	−0.016 (4)
C8A	0.057 (5)	0.047 (5)	0.034 (4)	0.007 (4)	0.014 (4)	0.000 (4)
C9A	0.038 (4)	0.042 (5)	0.036 (4)	0.007 (4)	0.014 (3)	−0.002 (4)
C10A	0.036 (4)	0.038 (5)	0.039 (4)	0.007 (4)	0.007 (3)	−0.002 (4)
C11A	0.035 (4)	0.022 (4)	0.039 (4)	0.005 (3)	0.008 (3)	0.006 (3)
C12A	0.043 (4)	0.034 (4)	0.036 (4)	0.010 (4)	0.009 (3)	0.005 (4)
C13A	0.030 (3)	0.034 (4)	0.037 (4)	0.009 (3)	0.005 (3)	−0.005 (4)
C14A	0.033 (4)	0.036 (5)	0.042 (4)	0.007 (4)	0.010 (3)	0.001 (4)
C15A	0.066 (6)	0.115 (12)	0.081 (7)	−0.029 (8)	0.023 (6)	0.027 (8)
C16A	0.048 (4)	0.044 (5)	0.050 (5)	−0.002 (5)	−0.002 (4)	−0.010 (5)
C17A	0.076 (6)	0.045 (6)	0.063 (5)	0.009 (5)	0.038 (5)	0.001 (5)
C18A	0.050 (5)	0.061 (6)	0.054 (5)	−0.009 (5)	−0.006 (4)	−0.015 (5)
O1B	0.100 (6)	0.023 (3)	0.076 (5)	−0.001 (3)	0.039 (4)	0.005 (3)
O2B	0.063 (4)	0.104 (6)	0.052 (3)	0.008 (5)	0.028 (3)	0.001 (5)
O3B	0.060 (3)	0.064 (4)	0.035 (3)	0.018 (4)	0.010 (3)	0.010 (3)
O4B	0.050 (3)	0.046 (3)	0.037 (3)	−0.001 (3)	0.018 (2)	0.000 (3)
O5B	0.049 (3)	0.044 (3)	0.045 (3)	0.021 (3)	0.013 (2)	0.004 (3)
N1B	0.056 (4)	0.030 (4)	0.037 (3)	0.010 (3)	0.020 (3)	0.001 (3)
N2B	0.042 (3)	0.040 (4)	0.041 (3)	−0.004 (3)	0.015 (3)	0.007 (3)
C1B	0.044 (4)	0.025 (4)	0.044 (4)	0.013 (3)	0.015 (3)	0.006 (3)
C2B	0.060 (5)	0.043 (5)	0.051 (5)	−0.008 (5)	0.012 (4)	−0.010 (4)
C3B	0.059 (5)	0.057 (6)	0.046 (5)	−0.001 (5)	0.021 (4)	−0.015 (4)
C4B	0.047 (4)	0.072 (7)	0.038 (4)	0.007 (5)	0.008 (3)	0.000 (5)
C5B	0.047 (5)	0.051 (6)	0.049 (5)	−0.002 (4)	0.014 (4)	0.002 (4)
C6B	0.047 (5)	0.051 (6)	0.043 (4)	0.003 (4)	0.013 (4)	−0.006 (4)
C7B	0.057 (5)	0.030 (5)	0.051 (5)	0.008 (4)	0.016 (4)	0.007 (4)
C8B	0.035 (4)	0.046 (5)	0.040 (4)	−0.003 (4)	0.011 (3)	−0.001 (4)
C9B	0.034 (4)	0.044 (5)	0.041 (4)	−0.005 (4)	0.008 (3)	−0.009 (4)
C10B	0.034 (4)	0.047 (5)	0.042 (4)	0.009 (4)	0.011 (3)	−0.009 (4)
C11B	0.039 (4)	0.038 (4)	0.040 (4)	0.006 (4)	0.004 (3)	−0.001 (4)
C12B	0.034 (4)	0.038 (4)	0.032 (4)	0.006 (4)	0.010 (3)	−0.002 (4)
C13B	0.030 (3)	0.040 (4)	0.037 (4)	0.001 (4)	0.013 (3)	−0.010 (4)
C14B	0.040 (4)	0.048 (5)	0.032 (4)	0.002 (4)	0.007 (3)	−0.003 (4)
C15B	0.061 (6)	0.124 (12)	0.081 (7)	−0.032 (8)	0.040 (6)	−0.035 (9)
C16B	0.052 (5)	0.038 (5)	0.063 (5)	0.012 (4)	0.004 (4)	0.010 (5)
C17B	0.072 (6)	0.060 (6)	0.053 (5)	−0.002 (6)	0.033 (5)	0.008 (6)
C18B	0.047 (5)	0.051 (5)	0.051 (5)	0.015 (5)	0.004 (4)	−0.009 (5)

Geometric parameters (Å, º) top

O1A—C7A	1.208 (13)	O1B—C7B	1.229 (11)
O2A—C4A	1.355 (10)	O2B—C4B	1.354 (9)
O2A—C15A	1.394 (15)	O2B—C15B	1.438 (15)
O3A—C11A	1.333 (9)	O3B—C11B	1.361 (10)
O3A—C16A	1.452 (10)	O3B—C16B	1.408 (10)
O4A—C12A	1.376 (8)	O4B—C12B	1.366 (8)
O4A—C17A	1.442 (11)	O4B—C17B	1.422 (11)
O5A—C13A	1.371 (9)	O5B—C18B	1.386 (11)
O5A—C18A	1.412 (11)	O5B—C13B	1.394 (9)
N1A—C7A	1.315 (12)	N1B—C7B	1.340 (11)
N1A—N2A	1.401 (9)	N1B—N2B	1.374 (8)
N1A—H1NA	0.8600	N1B—H1NB	0.8545
N2A—C8A	1.243 (12)	N2B—C8B	1.290 (11)
C1A—C6A	1.422 (17)	C1B—C2B	1.371 (11)
C1A—C2A	1.449 (16)	C1B—C6B	1.380 (12)
C1A—C7A	1.532 (13)	C1B—C7B	1.483 (11)
C2A—C3A	1.459 (18)	C2B—C3B	1.349 (11)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.39 (2)	C3B—C4B	1.402 (14)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.377 (14)	C4B—C5B	1.367 (12)
C5A—C6A	1.370 (13)	C5B—C6B	1.395 (11)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—H6A	0.9300	C6B—H6B	0.9300
C8A—C9A	1.493 (10)	C8B—C9B	1.474 (10)
C8A—H8AA	0.9300	C8B—H8B	0.9300
C9A—C10A	1.363 (11)	C9B—C10B	1.371 (12)
C9A—C14A	1.403 (11)	C9B—C14B	1.408 (11)
C10A—C11A	1.388 (10)	C10B—C11B	1.385 (10)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.409 (11)	C11B—C12B	1.420 (11)
C12A—C13A	1.398 (11)	C12B—C13B	1.376 (11)
C13A—C14A	1.381 (10)	C13B—C14B	1.382 (9)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15C	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15A	0.9600	C15B—H15F	0.9600
C16A—H16C	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16A	0.9600	C16B—H16F	0.9600
C17A—H17C	0.9600	C17B—H17D	0.9600
C17A—H17B	0.9600	C17B—H17E	0.9600
C17A—H17A	0.9600	C17B—H17F	0.9600
C18A—H18C	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18A	0.9600	C18B—H18F	0.9600

C4A—O2A—C15A	118.7 (9)	C4B—O2B—C15B	116.7 (8)
C11A—O3A—C16A	117.9 (6)	C11B—O3B—C16B	117.5 (6)
C12A—O4A—C17A	113.5 (6)	C12B—O4B—C17B	116.3 (7)
C13A—O5A—C18A	118.9 (6)	C18B—O5B—C13B	118.5 (6)
C7A—N1A—N2A	118.3 (9)	C7B—N1B—N2B	120.9 (7)
C7A—N1A—H1NA	120.8	C7B—N1B—H1NB	108.7
N2A—N1A—H1NA	120.8	N2B—N1B—H1NB	124.3
C8A—N2A—N1A	112.9 (8)	C8B—N2B—N1B	114.0 (7)
C6A—C1A—C2A	121.8 (9)	C2B—C1B—C6B	116.9 (7)
C6A—C1A—C7A	123.3 (8)	C2B—C1B—C7B	121.2 (8)
C2A—C1A—C7A	114.9 (10)	C6B—C1B—C7B	121.9 (8)
C1A—C2A—C3A	111.1 (15)	C3B—C2B—C1B	123.9 (9)
C1A—C2A—H2A	124.5	C3B—C2B—H2B	118.0
C3A—C2A—H2A	124.5	C1B—C2B—H2B	118.0
C4A—C3A—C2A	125.6 (11)	C2B—C3B—C4B	118.6 (8)
C4A—C3A—H3A	117.2	C2B—C3B—H3B	120.7
C2A—C3A—H3A	117.2	C4B—C3B—H3B	120.7
O2A—C4A—C5A	124.9 (11)	O2B—C4B—C5B	125.4 (10)
O2A—C4A—C3A	116.0 (9)	O2B—C4B—C3B	114.9 (8)
C5A—C4A—C3A	119.1 (9)	C5B—C4B—C3B	119.6 (8)
C6A—C5A—C4A	119.6 (11)	C4B—C5B—C6B	119.7 (9)
C6A—C5A—H5A	120.2	C4B—C5B—H5B	120.2
C4A—C5A—H5A	120.2	C6B—C5B—H5B	120.2
C5A—C6A—C1A	122.2 (10)	C1B—C6B—C5B	121.2 (8)
C5A—C6A—H6A	118.9	C1B—C6B—H6B	119.4
C1A—C6A—H6A	118.9	C5B—C6B—H6B	119.4
O1A—C7A—N1A	127.7 (10)	O1B—C7B—N1B	121.8 (8)
O1A—C7A—C1A	119.1 (9)	O1B—C7B—C1B	122.8 (8)
N1A—C7A—C1A	113.0 (9)	N1B—C7B—C1B	115.3 (8)
N2A—C8A—C9A	120.8 (8)	N2B—C8B—C9B	118.5 (8)
N2A—C8A—H8AA	119.6	N2B—C8B—H8B	120.7
C9A—C8A—H8AA	119.6	C9B—C8B—H8B	120.7
C10A—C9A—C14A	122.1 (7)	C10B—C9B—C14B	119.8 (7)
C10A—C9A—C8A	122.1 (7)	C10B—C9B—C8B	123.1 (7)
C14A—C9A—C8A	115.9 (7)	C14B—C9B—C8B	116.8 (8)
C9A—C10A—C11A	120.0 (7)	C9B—C10B—C11B	121.8 (7)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	119.1
C11A—C10A—H10A	120.0	C11B—C10B—H10B	119.1
O3A—C11A—C10A	126.8 (7)	O3B—C11B—C10B	126.8 (7)
O3A—C11A—C12A	114.4 (6)	O3B—C11B—C12B	114.5 (6)
C10A—C11A—C12A	118.8 (7)	C10B—C11B—C12B	118.4 (7)
O4A—C12A—C13A	120.6 (7)	O4B—C12B—C13B	120.5 (7)
O4A—C12A—C11A	118.8 (7)	O4B—C12B—C11B	120.4 (7)
C13A—C12A—C11A	120.6 (7)	C13B—C12B—C11B	119.2 (6)
O5A—C13A—C14A	123.9 (7)	C12B—C13B—C14B	122.0 (7)
O5A—C13A—C12A	116.4 (6)	C12B—C13B—O5B	115.6 (6)
C14A—C13A—C12A	119.7 (7)	C14B—C13B—O5B	122.4 (7)
C13A—C14A—C9A	118.7 (7)	C13B—C14B—C9B	118.5 (8)
C13A—C14A—H14A	120.6	C13B—C14B—H14B	120.7
C9A—C14A—H14A	120.6	C9B—C14B—H14B	120.7
O2A—C15A—H15C	109.5	O2B—C15B—H15D	109.5
O2A—C15A—H15B	109.5	O2B—C15B—H15E	109.5
H15C—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O2A—C15A—H15A	109.5	O2B—C15B—H15F	109.5
H15C—C15A—H15A	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15A	109.5	H15E—C15B—H15F	109.5
O3A—C16A—H16C	109.5	O3B—C16B—H16D	109.5
O3A—C16A—H16B	109.5	O3B—C16B—H16E	109.5
H16C—C16A—H16B	109.5	H16D—C16B—H16E	109.5
O3A—C16A—H16A	109.5	O3B—C16B—H16F	109.5
H16C—C16A—H16A	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16A	109.5	H16E—C16B—H16F	109.5
O4A—C17A—H17C	109.5	O4B—C17B—H17D	109.5
O4A—C17A—H17B	109.5	O4B—C17B—H17E	109.5
H17C—C17A—H17B	109.5	H17D—C17B—H17E	109.5
O4A—C17A—H17A	109.5	O4B—C17B—H17F	109.5
H17C—C17A—H17A	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17A	109.5	H17E—C17B—H17F	109.5
O5A—C18A—H18C	109.5	O5B—C18B—H18D	109.5
O5A—C18A—H18B	109.5	O5B—C18B—H18E	109.5
H18C—C18A—H18B	109.5	H18D—C18B—H18E	109.5
O5A—C18A—H18A	109.5	O5B—C18B—H18F	109.5
H18C—C18A—H18A	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18A	109.5	H18E—C18B—H18F	109.5

C7A—N1A—N2A—C8A	170.6 (9)	C7B—N1B—N2B—C8B	−165.1 (8)
C6A—C1A—C2A—C3A	−7.8 (19)	C6B—C1B—C2B—C3B	4.3 (14)
C7A—C1A—C2A—C3A	176.2 (11)	C7B—C1B—C2B—C3B	−173.6 (9)
C1A—C2A—C3A—C4A	10 (2)	C1B—C2B—C3B—C4B	−4.5 (15)
C15A—O2A—C4A—C5A	1.6 (18)	C15B—O2B—C4B—C5B	−4.3 (15)
C15A—O2A—C4A—C3A	−180.0 (12)	C15B—O2B—C4B—C3B	177.6 (9)
C2A—C3A—C4A—O2A	174.8 (15)	C2B—C3B—C4B—O2B	−178.8 (9)
C2A—C3A—C4A—C5A	−7 (2)	C2B—C3B—C4B—C5B	3.0 (14)
O2A—C4A—C5A—C6A	179.2 (12)	O2B—C4B—C5B—C6B	−179.6 (9)
C3A—C4A—C5A—C6A	0.9 (18)	C3B—C4B—C5B—C6B	−1.6 (14)
C4A—C5A—C6A—C1A	0.6 (18)	C2B—C1B—C6B—C5B	−2.6 (12)
C2A—C1A—C6A—C5A	3.4 (19)	C7B—C1B—C6B—C5B	175.2 (8)
C7A—C1A—C6A—C5A	179.0 (11)	C4B—C5B—C6B—C1B	1.4 (14)
N2A—N1A—C7A—O1A	3.5 (16)	N2B—N1B—C7B—O1B	15.2 (14)
N2A—N1A—C7A—C1A	−171.2 (7)	N2B—N1B—C7B—C1B	−169.2 (6)
C6A—C1A—C7A—O1A	−142.0 (12)	C2B—C1B—C7B—O1B	29.8 (14)
C2A—C1A—C7A—O1A	33.9 (15)	C6B—C1B—C7B—O1B	−148.0 (10)
C6A—C1A—C7A—N1A	33.2 (14)	C2B—C1B—C7B—N1B	−145.7 (9)
C2A—C1A—C7A—N1A	−150.8 (11)	C6B—C1B—C7B—N1B	36.5 (11)
N1A—N2A—C8A—C9A	−174.4 (7)	N1B—N2B—C8B—C9B	−172.2 (6)
N2A—C8A—C9A—C10A	−31.3 (13)	N2B—C8B—C9B—C10B	27.5 (12)
N2A—C8A—C9A—C14A	147.3 (9)	N2B—C8B—C9B—C14B	−158.0 (7)
C14A—C9A—C10A—C11A	−0.7 (12)	C14B—C9B—C10B—C11B	2.6 (13)
C8A—C9A—C10A—C11A	177.8 (7)	C8B—C9B—C10B—C11B	177.0 (8)
C16A—O3A—C11A—C10A	4.8 (11)	C16B—O3B—C11B—C10B	−2.3 (13)
C16A—O3A—C11A—C12A	−175.8 (7)	C16B—O3B—C11B—C12B	−177.2 (8)
C9A—C10A—C11A—O3A	177.8 (7)	C9B—C10B—C11B—O3B	−177.2 (8)
C9A—C10A—C11A—C12A	−1.7 (11)	C9B—C10B—C11B—C12B	−2.5 (13)
C17A—O4A—C12A—C13A	72.8 (9)	C17B—O4B—C12B—C13B	103.9 (10)
C17A—O4A—C12A—C11A	−108.5 (9)	C17B—O4B—C12B—C11B	−77.5 (9)
O3A—C11A—C12A—O4A	3.5 (10)	O3B—C11B—C12B—O4B	0.1 (12)
C10A—C11A—C12A—O4A	−177.0 (7)	C10B—C11B—C12B—O4B	−175.3 (8)
O3A—C11A—C12A—C13A	−177.7 (7)	O3B—C11B—C12B—C13B	178.6 (8)
C10A—C11A—C12A—C13A	1.8 (11)	C10B—C11B—C12B—C13B	3.3 (12)
C18A—O5A—C13A—C14A	0.3 (12)	O4B—C12B—C13B—C14B	174.1 (8)
C18A—O5A—C13A—C12A	178.5 (7)	C11B—C12B—C13B—C14B	−4.5 (13)
O4A—C12A—C13A—O5A	1.0 (11)	O4B—C12B—C13B—O5B	−3.0 (11)
C11A—C12A—C13A—O5A	−177.7 (7)	C11B—C12B—C13B—O5B	178.4 (7)
O4A—C12A—C13A—C14A	179.3 (7)	C18B—O5B—C13B—C12B	179.2 (8)
C11A—C12A—C13A—C14A	0.5 (11)	C18B—O5B—C13B—C14B	2.2 (12)
O5A—C13A—C14A—C9A	175.3 (7)	C12B—C13B—C14B—C9B	4.6 (12)
C12A—C13A—C14A—C9A	−2.9 (11)	O5B—C13B—C14B—C9B	−178.5 (7)
C10A—C9A—C14A—C13A	3.0 (12)	C10B—C9B—C14B—C13B	−3.6 (12)
C8A—C9A—C14A—C13A	−175.6 (7)	C8B—C9B—C14B—C13B	−178.2 (7)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C9A–C14A and C9B–C14B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Aⁱ	0.86	2.11	2.944 (13)	164
N1B—H1NB···O1Bⁱ	0.85	2.21	2.939 (9)	144
C8B—H8B···O1Bⁱ	0.93	2.52	3.287 (11)	140
C15B—H15D···O2Aⁱⁱ	0.96	2.60	3.498 (14)	156
C17B—H17D···O4Bⁱⁱⁱ	0.96	2.60	3.420 (10)	144
C16A—H16B···Cg1^iv	0.96	2.66	3.429 (10)	138
C16B—H16F···Cg2^iv	0.96	2.77	3.697 (10)	162
C18A—H18B···Cg1ⁱ	0.96	2.85	3.739 (10)	155
C18B—H18F···Cg2ⁱ	0.96	2.74	3.583 (10)	146

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₅
M_r	344.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	297
a, b, c (Å)	13.3344 (17), 5.0484 (6), 25.767 (3)
β (°)	98.250 (2)
V (Å³)	1716.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.26 × 0.25 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.975, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	12488, 3361, 2671
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.090, 0.275, 1.05
No. of reflections	3361
No. of parameters	453
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.47

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C9A–C14A and C9B–C14B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Aⁱ	0.86	2.11	2.944 (13)	164
N1B—H1NB···O1Bⁱ	0.85	2.21	2.939 (9)	144
C8B—H8B···O1Bⁱ	0.93	2.52	3.287 (11)	140
C15B—H15D···O2Aⁱⁱ	0.96	2.60	3.498 (14)	156
C17B—H17D···O4Bⁱⁱⁱ	0.96	2.60	3.420 (10)	144
C16A—H16B···Cg1^iv	0.96	2.66	3.429 (10)	138
C16B—H16F···Cg2^iv	0.96	2.77	3.697 (10)	162
C18A—H18B···Cg1ⁱ	0.96	2.85	3.739 (10)	155
C18B—H18F···Cg2ⁱ	0.96	2.74	3.583 (10)	146

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009. Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

The authors thank Prince of Songkla University and the Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. PP thanks the Development and Promotion of Science and Technology Talents Project for a fellowship. PP and JH thank the Crystal Materials Research Unit, Prince of Songkla University, for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Angelusiu, M. V., Barbuceanu, S.-F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055–2062. Web of Science CrossRef CAS PubMed Google Scholar
Bedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Horkaew, J. & Chantrapromma, S. (2011). Acta Cryst. E67, o2644–o2645. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o2985. Web of Science CSD CrossRef IUCr Journals Google Scholar
Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067–1071. Web of Science CrossRef PubMed CAS Google Scholar
Melnyk, P., Leroux, V., Sergheraert, C. & Grellier, P. (2006). Bioorg. Med. Chem. Lett. 16, 31–35. Web of Science CrossRef PubMed CAS Google Scholar
Promdet, P., Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3224. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425–429. PubMed CAS 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

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 3| March 2012| Pages o562-o563

doi:10.1107/S1600536812003534

Open

access