(E)-4-Meth­oxy-N′-(2,3,4-tri­meth­oxy­benzyl­idene)benzohydrazide monohydrate

Veeramanikandan, S.; Sherine, H.B.; Gunasekaran, B.; Chakkaravarthi, G.

doi:10.1107/S2414314616015261

organic compounds

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ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161526

doi:10.1107/S2414314616015261

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(E)-4-Methoxy-N′-(2,3,4-trimethoxybenzylidene)benzohydrazide monohydrate

S. Veeramanikandan,^a H. Benita Sherine,^a ^* B. Gunasekaran ^b and G. Chakkaravarthi ^c ^*

^aPG and Research Department of Chemistry, Periyar E.V. R. College (Autonomous), Trichy 620 023., India, ^bDepartment of Physics and Nanotechnology, SRM University, Kattankulathur, Tamil Nadu, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: beni2@rediffmail.com, chakkaravarthi_2005@yahoo.com,

Edited by M. Bolte, Goethe-Universität Frankfurt Germany (Received 20 September 2016; accepted 28 September 2016; online 30 September 2016)

The asymmetric unit of the title compound, C₁₈H₂₀N₂O₅·H₂O, consists of a benzohydrazide molecule which exists in an E conformation with respect to the C=N imine bond and a water molecule. The dihedral angle between the aromatic rings is 41.67 (9)°. The methoxy substituent of the 4-methoxyphenyl group is twisted at an angle of 6.8 (3)° out of the plane of the attached benzene ring. In the 2,4,5-trimethoxyphenyl unit, the para-methoxy group is coplanar with the ring [C—C—O—C = −1.5 (3)°], whereas the ortho- and meta-methoxy groups are twisted out of the plane of the ring [C—C—O—C = 75.4 (2) and −67.1 (2)°, respectively]. Two molecules are connected by two water molecules via O—H⋯O hydrogen bonds, generating an R₂²(8) ring motif. One of the water H atoms forms an additional hydrogen bond to an N atom. The water molecules act as an acceptor for an N—H⋯O hydrogen bond. As a result, a three-dimensional network is formed.

Keywords: crystal structure; hydrogen bonding; benzohydrazide.

CCDC reference: 1507058

Structure description

Benzohydrazide derivatives possess biological activities such as antifungal (Loncle et al., 2004 ), antimalarial (Melnyk et al., 2006 ) and antiproliferative (Raj et al., 2007 ). We report the synthesis and the crystal structure of the title compound (Fig. 1) whose geometric parameters are comparable with those of related structures (Fun et al., 2012 ; Horkaew et al., 2011 ). The dihedral angle between the planes of the C2–C7 and C10–C15 aromatic rings is 41.67 (9)°.

Figure 1
The molecular structure of the title compound, showing the atom labelling and 30% probability displacement ellipsoids.

The benzohydrazide molecule exists in an E conformation with respect to the C9=N2 imine bond [1.277 (2) Å] and the N1—N2—C9—C10 torsion angle is 179.79 (14)°. The methoxy substituent of 4-methoxyphenyl is twisted at an C7—C2—O1—C1 angle of 6.8 (3)°, with the attached benzene ring. The three methoxy groups of 2,4,5-trimethoxyphenyl unit have two different orientations: the para-methoxy group (at atom C13) is coplanar [C18—O5—C13—C12 = 178.49 (19)°] with the ring, whereas the ortho- and meta-methoxy groups (attached at atoms C11 and C12) are twisted out of the ring plane [C16—O3—C11—C10 = −108.9 (2)° and C17—O4—C12—C11 = 114.9 (2)°].

In the crystal (Fig. 2), the benzohydrazide and water molecules are linked by N—H⋯O hydrogen bonds and a C—H⋯O contact (Table 1). A pair of O—H⋯O (O6—H6A⋯O2ⁱ and O6—H6B⋯O2ⁱⁱ) hydrogen bonds generate an R₂²(8) ring motif and O—H⋯O (O6—H6B⋯O2ⁱⁱ) and O—H⋯N (O6—H6B⋯N2ⁱⁱ) hydrogen bonds generate a bifurcated R₁²(6) ring motif (Fig. 3 and Table 1). As a result, a three-dimensional network is formed (Fig. 2), which is additionally stabilized by C—H⋯π interactions.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.86 (1)	2.07 (1)	2.905 (2)	164 (2)
C9—H9⋯O6	0.93	2.45	3.258 (2)	146
O6—H6A⋯O2ⁱ	0.87 (1)	1.98 (1)	2.8204 (18)	163 (2)
O6—H6B⋯O2ⁱⁱ	0.86 (1)	2.11 (1)	2.914 (2)	156 (2)
O6—H6B⋯N2ⁱⁱ	0.86 (1)	2.54 (2)	3.1880 (19)	133 (2)
C1—H1C⋯Cg2ⁱⁱⁱ	0.96	2.95	3.900 (3)	171
C16—H16C⋯Cg1ⁱ	0.96	2.79	3.713 (2)	162
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
The crystal packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involving in hydrogen bonding have been omitted for clarity.

Figure 3
A partial view of the crystal packing, showing the various ring motifs.

Synthesis and crystallization

4-Methoxybenzohydrazide (0.001 mmol, 0.17 g) was dissolved in ethanol (10 ml). 2,3,4-trimethoxybenzaldehyde (0.001 mmol, 0.145 g) was added slowly followed by addition of concentrated HCl (0.2 mmol). The mixture was stirred continuously for 30 min at room temperature. The precipitate formed was filtered, then washed with petroleum ether (40–60%) and dried in a vacuum desiccator, and the crystals suitable for X-ray diffraction were harvested.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The reflection 100 was omitted during refinement due to being obscured by the beam stop.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₅·H₂O
M_r	362.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	16.1090 (9), 11.2205 (5), 10.7515 (5)
β (°)	104.888 (2)
V (Å³)	1878.11 (16)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.28 × 0.24

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.962, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	14944, 4685, 2334
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.145, 0.99
No. of reflections	4685
No. of parameters	249
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008 ), SHELXL2016 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1507058

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616015261/bt4029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616015261/bt4029Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616015261/bt4029Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

(E)-4-Methoxy-N'-(2,3,4-trimethoxybenzylidene)benzohydrazide monohydrate top

Crystal data top

C₁₈H₂₀N₂O₅·H₂O	F(000) = 768
M_r = 362.37	D_x = 1.282 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.1090 (9) Å	Cell parameters from 2417 reflections
b = 11.2205 (5) Å	θ = 2.1–28.3°
c = 10.7515 (5) Å	µ = 0.10 mm⁻¹
β = 104.888 (2)°	T = 295 K
V = 1878.11 (16) Å³	Block, colourless
Z = 4	0.30 × 0.28 × 0.24 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2334 reflections with I > 2σ(I)
ω and φ scan	R_int = 0.037
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θ_max = 28.4°, θ_min = 2.6°
T_min = 0.962, T_max = 0.986	h = −21→19
14944 measured reflections	k = −15→14
4685 independent reflections	l = −11→14

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0658P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
4685 reflections	Δρ_max = 0.18 e Å⁻³
249 parameters	Δρ_min = −0.21 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.24421 (17)	0.0490 (2)	−0.1222 (3)	0.0886 (8)
H1A	1.280361	0.069028	−0.177490	0.133*
H1B	1.193612	0.009106	−0.171245	0.133*
H1C	1.274869	−0.002702	−0.054730	0.133*
C2	1.16371 (12)	0.14659 (18)	0.00676 (19)	0.0545 (5)
C3	1.13670 (13)	0.25364 (18)	0.0479 (2)	0.0647 (6)
H3	1.158028	0.325170	0.025187	0.078*
C4	1.07928 (13)	0.25478 (17)	0.1212 (2)	0.0581 (5)
H4	1.061002	0.327246	0.146745	0.070*
C5	1.04751 (11)	0.14890 (16)	0.15839 (16)	0.0447 (4)
C6	1.07691 (12)	0.04319 (16)	0.11999 (17)	0.0471 (5)
H6	1.057605	−0.028326	0.146181	0.056*
C7	1.13406 (12)	0.04018 (17)	0.04393 (18)	0.0504 (5)
H7	1.152323	−0.032192	0.018120	0.060*
C8	0.98183 (12)	0.14453 (16)	0.23180 (17)	0.0474 (5)
C9	0.79901 (11)	0.31185 (16)	0.22430 (16)	0.0442 (4)
H9	0.803603	0.361590	0.157194	0.053*
C10	0.72665 (11)	0.32514 (15)	0.27982 (15)	0.0403 (4)
C11	0.66504 (12)	0.41359 (15)	0.23211 (16)	0.0437 (4)
C12	0.59547 (12)	0.42884 (16)	0.28314 (17)	0.0497 (5)
C13	0.58618 (12)	0.35767 (16)	0.38446 (17)	0.0506 (5)
C14	0.64630 (12)	0.26918 (16)	0.43072 (17)	0.0512 (5)
H14	0.640208	0.220152	0.497556	0.061*
C15	0.71445 (12)	0.25373 (16)	0.37852 (16)	0.0469 (5)
H15	0.753788	0.193422	0.410268	0.056*
C16	0.69663 (16)	0.6007 (2)	0.1529 (2)	0.0836 (8)
H16A	0.657851	0.639264	0.194522	0.125*
H16B	0.694892	0.640562	0.073201	0.125*
H16C	0.753916	0.604094	0.207760	0.125*
C17	0.45299 (16)	0.4792 (2)	0.1714 (3)	0.1005 (10)
H17A	0.447906	0.473042	0.080714	0.151*
H17B	0.411900	0.535857	0.186205	0.151*
H17C	0.442236	0.402774	0.204290	0.151*
C18	0.50355 (17)	0.3094 (2)	0.5323 (2)	0.0897 (8)
H18A	0.494895	0.228135	0.503843	0.135*
H18B	0.453681	0.337232	0.556795	0.135*
H18C	0.552753	0.314100	0.604811	0.135*
N2	0.85666 (10)	0.23302 (13)	0.26582 (14)	0.0473 (4)
N1	0.92169 (10)	0.23108 (14)	0.20414 (15)	0.0483 (4)
O1	1.22019 (10)	0.15475 (13)	−0.06744 (16)	0.0771 (5)
O2	0.97921 (8)	0.06501 (12)	0.31030 (13)	0.0609 (4)
O3	0.67178 (9)	0.47970 (11)	0.12780 (12)	0.0582 (4)
O4	0.53704 (9)	0.51746 (12)	0.23501 (15)	0.0699 (4)
O5	0.51735 (10)	0.38125 (13)	0.43079 (14)	0.0729 (4)
O6	0.89533 (9)	0.42585 (12)	0.02007 (13)	0.0578 (4)
H1	0.9222 (11)	0.2829 (13)	0.1455 (13)	0.051 (5)*
H6A	0.9271 (12)	0.4808 (15)	0.0652 (18)	0.076*
H6B	0.9070 (14)	0.417 (2)	−0.0528 (13)	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0936 (19)	0.0836 (18)	0.1047 (19)	0.0148 (14)	0.0550 (16)	0.0022 (15)
C2	0.0486 (11)	0.0563 (13)	0.0610 (12)	0.0044 (9)	0.0182 (10)	0.0093 (10)
C3	0.0633 (14)	0.0437 (11)	0.0948 (16)	0.0003 (10)	0.0341 (12)	0.0114 (11)
C4	0.0572 (12)	0.0415 (11)	0.0798 (14)	0.0042 (9)	0.0252 (11)	0.0023 (10)
C5	0.0427 (10)	0.0435 (10)	0.0459 (10)	0.0040 (8)	0.0076 (8)	0.0055 (8)
C6	0.0474 (11)	0.0412 (10)	0.0490 (10)	0.0014 (8)	0.0058 (9)	0.0077 (8)
C7	0.0517 (12)	0.0439 (11)	0.0533 (11)	0.0069 (9)	0.0092 (9)	0.0020 (9)
C8	0.0500 (11)	0.0440 (10)	0.0453 (10)	0.0018 (9)	0.0069 (9)	0.0025 (9)
C9	0.0482 (11)	0.0444 (10)	0.0370 (9)	−0.0022 (8)	0.0056 (8)	0.0016 (8)
C10	0.0429 (10)	0.0391 (9)	0.0359 (9)	−0.0022 (8)	0.0047 (7)	0.0006 (8)
C11	0.0525 (11)	0.0402 (10)	0.0356 (9)	0.0003 (8)	0.0066 (8)	0.0016 (8)
C12	0.0597 (13)	0.0402 (10)	0.0477 (10)	0.0121 (9)	0.0112 (9)	0.0041 (9)
C13	0.0547 (12)	0.0516 (11)	0.0477 (11)	0.0070 (9)	0.0169 (9)	−0.0020 (9)
C14	0.0599 (12)	0.0486 (11)	0.0447 (10)	0.0027 (9)	0.0129 (9)	0.0086 (9)
C15	0.0489 (11)	0.0436 (10)	0.0452 (10)	0.0045 (8)	0.0069 (8)	0.0059 (9)
C16	0.0892 (18)	0.0592 (14)	0.0907 (17)	−0.0149 (12)	0.0019 (14)	0.0268 (13)
C17	0.0813 (19)	0.099 (2)	0.103 (2)	0.0370 (15)	−0.0102 (16)	0.0022 (16)
C18	0.1019 (19)	0.0920 (18)	0.0959 (18)	0.0139 (16)	0.0632 (16)	0.0193 (15)
N2	0.0458 (9)	0.0488 (9)	0.0476 (8)	0.0028 (7)	0.0125 (7)	0.0042 (7)
N1	0.0503 (10)	0.0473 (9)	0.0489 (9)	0.0064 (7)	0.0155 (7)	0.0119 (8)
O1	0.0806 (11)	0.0649 (10)	0.1004 (12)	0.0059 (8)	0.0497 (9)	0.0103 (9)
O2	0.0664 (9)	0.0581 (8)	0.0600 (8)	0.0134 (7)	0.0195 (7)	0.0202 (7)
O3	0.0713 (9)	0.0526 (8)	0.0499 (8)	0.0039 (7)	0.0141 (6)	0.0169 (6)
O4	0.0737 (11)	0.0588 (9)	0.0795 (10)	0.0268 (8)	0.0236 (8)	0.0181 (7)
O5	0.0831 (11)	0.0767 (10)	0.0708 (9)	0.0247 (8)	0.0414 (8)	0.0134 (8)
O6	0.0684 (10)	0.0563 (9)	0.0507 (8)	−0.0118 (7)	0.0189 (7)	−0.0035 (7)

Geometric parameters (Å, º) top

C1—O1	1.422 (3)	C11—C12	1.379 (3)
C1—H1A	0.9600	C12—O4	1.376 (2)
C1—H1B	0.9600	C12—C13	1.389 (3)
C1—H1C	0.9600	C13—O5	1.353 (2)
C2—O1	1.359 (2)	C13—C14	1.387 (2)
C2—C7	1.383 (3)	C14—C15	1.366 (2)
C2—C3	1.388 (3)	C14—H14	0.9300
C3—C4	1.361 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—O3	1.422 (2)
C4—C5	1.392 (3)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.379 (2)	C16—H16C	0.9600
C5—C8	1.474 (3)	C17—O4	1.418 (3)
C6—C7	1.380 (3)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C7—H7	0.9300	C17—H17C	0.9600
C8—O2	1.236 (2)	C18—O5	1.420 (3)
C8—N1	1.350 (2)	C18—H18A	0.9600
C9—N2	1.277 (2)	C18—H18B	0.9600
C9—C10	1.447 (2)	C18—H18C	0.9600
C9—H9	0.9300	N2—N1	1.376 (2)
C10—C15	1.383 (2)	N1—H1	0.859 (9)
C10—C11	1.404 (2)	O6—H6A	0.865 (9)
C11—O3	1.372 (2)	O6—H6B	0.858 (9)

O1—C1—H1A	109.5	C11—C12—C13	120.19 (16)
O1—C1—H1B	109.5	O5—C13—C14	124.80 (18)
H1A—C1—H1B	109.5	O5—C13—C12	116.09 (16)
O1—C1—H1C	109.5	C14—C13—C12	119.11 (19)
H1A—C1—H1C	109.5	C15—C14—C13	120.29 (17)
H1B—C1—H1C	109.5	C15—C14—H14	119.9
O1—C2—C7	124.14 (18)	C13—C14—H14	119.9
O1—C2—C3	116.16 (18)	C14—C15—C10	121.95 (16)
C7—C2—C3	119.7 (2)	C14—C15—H15	119.0
C4—C3—C2	120.54 (19)	C10—C15—H15	119.0
C4—C3—H3	119.7	O3—C16—H16A	109.5
C2—C3—H3	119.7	O3—C16—H16B	109.5
C3—C4—C5	120.87 (18)	H16A—C16—H16B	109.5
C3—C4—H4	119.6	O3—C16—H16C	109.5
C5—C4—H4	119.6	H16A—C16—H16C	109.5
C6—C5—C4	117.90 (18)	H16B—C16—H16C	109.5
C6—C5—C8	118.71 (16)	O4—C17—H17A	109.5
C4—C5—C8	123.33 (17)	O4—C17—H17B	109.5
C5—C6—C7	122.08 (17)	H17A—C17—H17B	109.5
C5—C6—H6	119.0	O4—C17—H17C	109.5
C7—C6—H6	119.0	H17A—C17—H17C	109.5
C6—C7—C2	118.87 (18)	H17B—C17—H17C	109.5
C6—C7—H7	120.6	O5—C18—H18A	109.5
C2—C7—H7	120.6	O5—C18—H18B	109.5
O2—C8—N1	121.41 (19)	H18A—C18—H18B	109.5
O2—C8—C5	122.99 (17)	O5—C18—H18C	109.5
N1—C8—C5	115.55 (16)	H18A—C18—H18C	109.5
N2—C9—C10	121.17 (16)	H18B—C18—H18C	109.5
N2—C9—H9	119.4	C9—N2—N1	114.68 (15)
C10—C9—H9	119.4	C8—N1—N2	119.82 (16)
C15—C10—C11	117.60 (17)	C8—N1—H1	120.5 (12)
C15—C10—C9	123.02 (16)	N2—N1—H1	119.6 (12)
C11—C10—C9	119.39 (16)	C2—O1—C1	118.76 (17)
O3—C11—C12	120.08 (16)	C11—O3—C16	116.04 (15)
O3—C11—C10	118.94 (17)	C12—O4—C17	116.03 (16)
C12—C11—C10	120.84 (16)	C13—O5—C18	118.47 (17)
O4—C12—C11	119.17 (17)	H6A—O6—H6B	111 (2)
O4—C12—C13	120.61 (18)

O1—C2—C3—C4	179.10 (18)	C10—C11—C12—C13	1.1 (3)
C7—C2—C3—C4	−2.0 (3)	O4—C12—C13—O5	0.1 (3)
C2—C3—C4—C5	1.1 (3)	C11—C12—C13—O5	178.15 (16)
C3—C4—C5—C6	0.8 (3)	O4—C12—C13—C14	−179.95 (16)
C3—C4—C5—C8	−176.64 (17)	C11—C12—C13—C14	−1.9 (3)
C4—C5—C6—C7	−1.9 (3)	O5—C13—C14—C15	−178.97 (17)
C8—C5—C6—C7	175.68 (16)	C12—C13—C14—C15	1.1 (3)
C5—C6—C7—C2	1.0 (3)	C13—C14—C15—C10	0.6 (3)
O1—C2—C7—C6	179.75 (17)	C11—C10—C15—C14	−1.4 (2)
C3—C2—C7—C6	1.0 (3)	C9—C10—C15—C14	178.98 (16)
C6—C5—C8—O2	34.9 (2)	C10—C9—N2—N1	−179.79 (14)
C4—C5—C8—O2	−147.69 (19)	O2—C8—N1—N2	1.2 (3)
C6—C5—C8—N1	−142.51 (16)	C5—C8—N1—N2	178.68 (14)
C4—C5—C8—N1	34.9 (2)	C9—N2—N1—C8	−173.92 (15)
N2—C9—C10—C15	−0.9 (2)	C7—C2—O1—C1	6.8 (3)
N2—C9—C10—C11	179.46 (16)	C3—C2—O1—C1	−174.4 (2)
C15—C10—C11—O3	−175.04 (14)	C12—C11—O3—C16	75.4 (2)
C9—C10—C11—O3	4.6 (2)	C10—C11—O3—C16	−108.9 (2)
C15—C10—C11—C12	0.6 (2)	C11—C12—O4—C17	114.9 (2)
C9—C10—C11—C12	−179.80 (15)	C13—C12—O4—C17	−67.1 (2)
O3—C11—C12—O4	−5.3 (3)	C14—C13—O5—C18	−1.5 (3)
C10—C11—C12—O4	179.15 (15)	C12—C13—O5—C18	178.49 (19)
O3—C11—C12—C13	176.63 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.86 (1)	2.07 (1)	2.905 (2)	164 (2)
C9—H9···O6	0.93	2.45	3.258 (2)	146
O6—H6A···O2ⁱ	0.87 (1)	1.98 (1)	2.8204 (18)	163 (2)
O6—H6B···O2ⁱⁱ	0.86 (1)	2.11 (1)	2.914 (2)	156 (2)
O6—H6B···N2ⁱⁱ	0.86 (1)	2.54 (2)	3.1880 (19)	133 (2)
C1—H1C···Cg2ⁱⁱⁱ	0.96	2.95	3.900 (3)	171
C16—H16C···Cg1ⁱ	0.96	2.79	3.713 (2)	162

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

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Promdet, P., Horkaew, J. & Chantrapromma, S. (2012). Acta Cryst. E68, o562–o563. 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
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
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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