2-[(E)-(Morpholin-4-yl­imino)­meth­yl]-6-(morpholin-4-ylmeth­yl)phenol

Akkurt, M.; Jarrahpour, A.; Chermahini, M.M.; Aberi, M.; Büyükgüngör, O.

doi:10.1107/S160053681302566X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1571

doi:10.1107/S160053681302566X

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2-[(E)-(Morpholin-4-ylimino)methyl]-6-(morpholin-4-ylmethyl)phenol

Mehmet Akkurt,^a ^* Aliasghar Jarrahpour,^b Mehdi Mohammadi Chermahini,^b Mahdi Aberi ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 16 September 2013; accepted 17 September 2013; online 21 September 2013)

The title compound, C₁₆H₂₃N₃O₃, contains two morpholine rings, each of which adopts a chair conformation. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, leading to a S(6) ring. In the crystal, molecules are linked into zigzag chains along the c-axis direction by C—H⋯O and C—H⋯π interactions.

CCDC reference: 961399

Related literature

For background to Schiff bases and their applications, see: Dhar & Taploo (1982 ); Nelson et al. (2004 ); Silva et al. (2011 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₂₃N₃O₃
M_r = 305.37
Monoclinic, P 2₁ /c
a = 9.0074 (6) Å
b = 15.7781 (14) Å
c = 11.3083 (7) Å
β = 99.052 (5)°
V = 1587.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.51 × 0.32 × 0.09 mm

Data collection

STOE IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.961, T_max = 0.990
23637 measured reflections
3289 independent reflections
1955 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.123
S = 1.03
3289 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C6–C11 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.91	2.636 (2)	146
C13—H13A⋯O3ⁱ	0.97	2.55	3.416 (3)	149
C4—H4A⋯Cg3ⁱ	0.97	2.87	3.646 (3)	138
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 961399

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681302566X/tk5257sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302566X/tk5257Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681302566X/tk5257Isup3.cml

checkCIF report

Comment top

Schiff bases are formed by the condensation of a primary amine with a carbonyl compound (Dhar & Taploo, 1982). They are widely used for industrial purposes and also exhibit a broad range of biological activities (Silva et al., 2011). The morpholine moiety has been utilized extensively by the pharmaceutical industry in drug design, often because of the improvement in pharmacokinetic properties it can confer. The World Drug Index contains well over 100 drugs incorporating this structural feature, including its presence as a side-chain, scaffold, and within fused-ring systems. The biological utility of molecules containing the morpholine moiety is wide-ranging (Nelson et al., 2004). Therefore, Schiff base (I), which has the two morpholine rings, was synthesized and its X-ray structure is reported here.

The two morpholine rings (N1/O1/C1–C4 and N3/O3/C13–C16) of (I), Fig. 1, adopt a chair conformation with puckering parameters (Cremer & Pople, 1975) of Q_T = 0.564 (3) Å, θ = 180.0 (2)°, ϕ = 163 (33)° and Q_T = 0.553 (2) Å, θ = 4.6 (2)°, ϕ = 19 (3)°, respectively. The N1–C5–C6–C7, C5–C6–C7–O2, O2–C7–C8–C12 and C8–C12–N2–N3 torsion angles are -158.0 (2), 0.6 (3), -1.0 (3) and 179.97 (19)°, respectively.

An intramolecular O—H···N hydrogen bond (Table 1) stabilizes the molecular conformation of (I), forming a pseudo six-membered ring with a graph set motif S(6) (Bernstein et al., 1995). In the crystal structure, C—H···O hydrogen bonds link the molecules into infinite one-dimensional chains along [001], with a C(4) graph-set motif (Table 1, Fig. 2). Additional C—H···π interactions also assist in the stabilization of the chain.

Related literature top

For background to Schiff bases and their applications, see: Dhar & Taploo (1982); Nelson et al. (2004); Silva et al. (2011). For ring puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 2-hydroxy-3-(morpholinomethyl)benzaldehyde (1.0 mmol) and morpholin-4-amine (1.0 mmol) was refluxed in EtOH for 4 h. After cooling the solution, the precipitate formed was filtered and recrystallized from ethanol to give yellow crystals in 82% yield. M. pt: 407–409 K. IR (KBr) cm^-1: 1612 (C=N). ¹H-NMR (250 MHz, CDCl₃), δ (p.p.m.): 2.57, 3.15 (CH₂N, t, 8H, J=5 Hz), 3.66 (CH₂, s, 2H), 3.75, 3.88 (CH₂O, t, 8H, J=5 Hz), 6.84 (aromatic H, t, 1H, J=7.5 Hz), 7.23 (aromatic H, d, 2H, J=7.5 Hz), 7.80 (HC=N, s, 1H), 11.71 (OH, s, 1H). ¹³C-NMR (62.9 MHz, CDCl₃), δ (p.p.m): 51.8, 53.3 (CH₂N), 57.6 (CH₂), 66.2, 66.7 (CH₂O), 118.8–139.1 (aromatic carbons), 156.0 (C=N).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with the atom-labelling scheme and 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of (I) viewed down the a axis. Hydrogen bonds are indicated by broken lines. H atoms not participating in hydrogen bonding have been omitted for clarity.

2-[(E)-(Morpholin-4-ylimino)methyl]-6-(morpholin-4-ylmethyl)phenol top

Crystal data top

C₁₆H₂₃N₃O₃	F(000) = 656
M_r = 305.37	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17755 reflections
a = 9.0074 (6) Å	θ = 2.2–27.3°
b = 15.7781 (14) Å	µ = 0.09 mm⁻¹
c = 11.3083 (7) Å	T = 296 K
β = 99.052 (5)°	Shapeless, yellow
V = 1587.1 (2) Å³	0.51 × 0.32 × 0.09 mm
Z = 4

Data collection top

STOE IPDS 2 diffractometer	3289 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1955 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.089
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.2°
ω–scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
T_min = 0.961, T_max = 0.990	l = −14→14
23637 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.123	W = 1/[Σ²(FO²) + (0.0519P)²] WHERE P = (FO² + 2FC²)/3
S = 1.03	(Δ/σ)_max < 0.001
3289 reflections	Δρ_max = 0.13 e Å⁻³
199 parameters	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₆H₂₃N₃O₃	V = 1587.1 (2) Å³
M_r = 305.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0074 (6) Å	µ = 0.09 mm⁻¹
b = 15.7781 (14) Å	T = 296 K
c = 11.3083 (7) Å	0.51 × 0.32 × 0.09 mm
β = 99.052 (5)°

Data collection top

STOE IPDS 2 diffractometer	3289 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1955 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.990	R_int = 0.089
23637 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
3289 reflections	Δρ_min = −0.12 e Å⁻³
199 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.7886 (2)	0.05694 (15)	0.26574 (16)	0.0912 (9)
O2	0.46117 (17)	0.15800 (11)	0.73906 (12)	0.0586 (5)
O3	0.15802 (19)	0.22570 (11)	1.21636 (13)	0.0659 (6)
N1	0.7555 (2)	0.12192 (11)	0.49469 (14)	0.0497 (6)
N2	0.3995 (2)	0.13953 (12)	0.95782 (15)	0.0500 (6)
N3	0.2980 (2)	0.14585 (12)	1.03797 (14)	0.0514 (6)
C1	0.7095 (3)	0.03684 (16)	0.4572 (2)	0.0669 (9)
C2	0.8012 (4)	0.00352 (19)	0.3670 (2)	0.0838 (11)
C3	0.8362 (4)	0.1393 (2)	0.3018 (2)	0.0859 (13)
C4	0.7453 (3)	0.17607 (16)	0.38952 (19)	0.0614 (8)
C5	0.6625 (3)	0.15608 (18)	0.57868 (19)	0.0667 (9)
C6	0.7055 (3)	0.12328 (14)	0.70585 (18)	0.0523 (8)
C7	0.5991 (2)	0.12627 (13)	0.78287 (18)	0.0467 (7)
C8	0.6357 (2)	0.09994 (13)	0.90283 (18)	0.0452 (7)
C9	0.7809 (3)	0.07110 (14)	0.9425 (2)	0.0562 (8)
C10	0.8869 (3)	0.06887 (16)	0.8678 (2)	0.0629 (9)
C11	0.8489 (3)	0.09507 (15)	0.7501 (2)	0.0600 (9)
C12	0.5296 (3)	0.10624 (14)	0.98800 (18)	0.0501 (8)
C13	0.2093 (3)	0.22298 (16)	1.01350 (19)	0.0584 (9)
C14	0.0910 (3)	0.22850 (19)	1.0939 (2)	0.0691 (10)
C15	0.2348 (3)	0.14835 (18)	1.2391 (2)	0.0707 (10)
C16	0.3593 (3)	0.13650 (15)	1.16513 (18)	0.0566 (8)
H1A	0.60400	0.03710	0.42230	0.0800*
H1B	0.72160	−0.00030	0.52650	0.0800*
H2	0.40790	0.15670	0.79150	0.0880*
H2A	0.90580	−0.00040	0.40360	0.1010*
H2B	0.76680	−0.05290	0.34220	0.1010*
H3A	0.82770	0.17570	0.23190	0.1030*
H3B	0.94120	0.13770	0.33800	0.1030*
H4A	0.78230	0.23230	0.41320	0.0740*
H4B	0.64110	0.18110	0.35220	0.0740*
H5A	0.55830	0.14180	0.55030	0.0800*
H5B	0.67080	0.21740	0.57950	0.0800*
H9	0.80660	0.05290	1.02130	0.0670*
H10	0.98380	0.04990	0.89600	0.0750*
H11	0.92120	0.09370	0.69980	0.0720*
H12	0.55720	0.08570	1.06540	0.0600*
H13A	0.16130	0.22320	0.93050	0.0700*
H13B	0.27480	0.27200	1.02640	0.0700*
H14A	0.03510	0.28090	1.07820	0.0830*
H14B	0.02110	0.18170	1.07680	0.0830*
H15A	0.16360	0.10220	1.22240	0.0850*
H15B	0.27740	0.14560	1.32330	0.0850*
H16A	0.43750	0.17840	1.18800	0.0680*
H16B	0.40340	0.08060	1.17960	0.0680*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1117 (17)	0.1190 (17)	0.0446 (10)	0.0059 (13)	0.0173 (10)	−0.0190 (11)
O2	0.0528 (9)	0.0838 (11)	0.0411 (8)	0.0177 (8)	0.0129 (7)	0.0064 (8)
O3	0.0724 (12)	0.0822 (12)	0.0457 (9)	0.0009 (9)	0.0178 (8)	−0.0106 (8)
N1	0.0550 (11)	0.0584 (12)	0.0378 (9)	0.0049 (9)	0.0141 (8)	0.0022 (8)
N2	0.0553 (12)	0.0586 (11)	0.0379 (9)	−0.0038 (9)	0.0128 (8)	−0.0032 (8)
N3	0.0578 (11)	0.0657 (12)	0.0339 (9)	−0.0087 (10)	0.0168 (8)	−0.0046 (8)
C1	0.0723 (17)	0.0674 (16)	0.0628 (15)	−0.0028 (13)	0.0164 (13)	0.0056 (13)
C2	0.101 (2)	0.085 (2)	0.0652 (17)	0.0133 (17)	0.0121 (16)	−0.0203 (16)
C3	0.086 (2)	0.122 (3)	0.0555 (16)	−0.0115 (19)	0.0288 (15)	0.0107 (17)
C4	0.0664 (15)	0.0706 (16)	0.0480 (13)	−0.0028 (13)	0.0118 (11)	0.0105 (12)
C5	0.0764 (17)	0.0838 (17)	0.0434 (13)	0.0302 (14)	0.0202 (12)	0.0073 (12)
C6	0.0625 (15)	0.0575 (14)	0.0383 (11)	0.0173 (11)	0.0119 (10)	0.0016 (10)
C7	0.0533 (14)	0.0458 (12)	0.0409 (11)	0.0097 (10)	0.0070 (10)	−0.0036 (9)
C8	0.0555 (14)	0.0405 (11)	0.0396 (11)	0.0037 (10)	0.0075 (10)	−0.0008 (9)
C9	0.0722 (16)	0.0564 (14)	0.0390 (12)	0.0141 (12)	0.0053 (11)	0.0014 (10)
C10	0.0619 (16)	0.0742 (16)	0.0509 (14)	0.0248 (13)	0.0036 (12)	0.0025 (12)
C11	0.0608 (16)	0.0727 (16)	0.0494 (13)	0.0222 (12)	0.0177 (11)	0.0032 (12)
C12	0.0702 (17)	0.0460 (12)	0.0352 (11)	−0.0021 (11)	0.0122 (11)	−0.0006 (9)
C13	0.0563 (15)	0.0766 (17)	0.0433 (12)	0.0045 (12)	0.0110 (11)	0.0012 (12)
C14	0.0611 (16)	0.099 (2)	0.0503 (14)	−0.0016 (14)	0.0181 (12)	−0.0086 (14)
C15	0.094 (2)	0.0805 (18)	0.0419 (13)	−0.0078 (16)	0.0245 (13)	−0.0040 (13)
C16	0.0771 (16)	0.0586 (15)	0.0355 (11)	0.0008 (12)	0.0129 (11)	0.0013 (10)

Geometric parameters (Å, º) top

O1—C2	1.412 (3)	C15—C16	1.512 (4)
O1—C3	1.409 (4)	C1—H1A	0.9700
O2—C7	1.359 (2)	C1—H1B	0.9700
O3—C14	1.422 (3)	C2—H2A	0.9700
O3—C15	1.406 (3)	C2—H2B	0.9700
O2—H2	0.8200	C3—H3A	0.9700
N1—C1	1.449 (3)	C3—H3B	0.9700
N1—C5	1.465 (3)	C4—H4A	0.9700
N1—C4	1.456 (3)	C4—H4B	0.9700
N2—N3	1.389 (2)	C5—H5A	0.9700
N2—C12	1.281 (3)	C5—H5B	0.9700
N3—C16	1.464 (3)	C9—H9	0.9300
N3—C13	1.458 (3)	C10—H10	0.9300
C1—C2	1.505 (4)	C11—H11	0.9300
C3—C4	1.499 (4)	C12—H12	0.9300
C5—C6	1.520 (3)	C13—H13A	0.9700
C6—C7	1.394 (3)	C13—H13B	0.9700
C6—C11	1.383 (4)	C14—H14A	0.9700
C7—C8	1.407 (3)	C14—H14B	0.9700
C8—C12	1.463 (3)	C15—H15A	0.9700
C8—C9	1.391 (3)	C15—H15B	0.9700
C9—C10	1.371 (4)	C16—H16A	0.9700
C10—C11	1.384 (3)	C16—H16B	0.9700
C13—C14	1.508 (4)

C2—O1—C3	109.51 (19)	O1—C3—H3B	109.00
C14—O3—C15	109.05 (18)	C4—C3—H3A	109.00
C7—O2—H2	109.00	C4—C3—H3B	109.00
C1—N1—C5	111.37 (19)	H3A—C3—H3B	108.00
C4—N1—C5	110.18 (18)	N1—C4—H4A	110.00
C1—N1—C4	109.06 (17)	N1—C4—H4B	110.00
N3—N2—C12	121.63 (17)	C3—C4—H4A	110.00
N2—N3—C16	116.65 (18)	C3—C4—H4B	110.00
C13—N3—C16	112.40 (17)	H4A—C4—H4B	108.00
N2—N3—C13	109.48 (17)	N1—C5—H5A	109.00
N1—C1—C2	111.1 (2)	N1—C5—H5B	109.00
O1—C2—C1	111.0 (2)	C6—C5—H5A	109.00
O1—C3—C4	112.1 (3)	C6—C5—H5B	109.00
N1—C4—C3	110.0 (2)	H5A—C5—H5B	108.00
N1—C5—C6	113.7 (2)	C8—C9—H9	119.00
C5—C6—C7	118.8 (2)	C10—C9—H9	119.00
C5—C6—C11	122.4 (2)	C9—C10—H10	120.00
C7—C6—C11	118.66 (19)	C11—C10—H10	120.00
O2—C7—C8	121.49 (17)	C6—C11—H11	119.00
C6—C7—C8	120.84 (18)	C10—C11—H11	119.00
O2—C7—C6	117.64 (18)	N2—C12—H12	119.00
C7—C8—C9	118.25 (18)	C8—C12—H12	119.00
C9—C8—C12	119.24 (19)	N3—C13—H13A	110.00
C7—C8—C12	122.43 (18)	N3—C13—H13B	110.00
C8—C9—C10	121.4 (2)	C14—C13—H13A	109.00
C9—C10—C11	119.6 (2)	C14—C13—H13B	110.00
C6—C11—C10	121.3 (2)	H13A—C13—H13B	108.00
N2—C12—C8	121.17 (18)	O3—C14—H14A	109.00
N3—C13—C14	110.6 (2)	O3—C14—H14B	109.00
O3—C14—C13	110.7 (2)	C13—C14—H14A	110.00
O3—C15—C16	113.1 (2)	C13—C14—H14B	110.00
N3—C16—C15	109.4 (2)	H14A—C14—H14B	108.00
N1—C1—H1A	109.00	O3—C15—H15A	109.00
N1—C1—H1B	109.00	O3—C15—H15B	109.00
C2—C1—H1A	109.00	C16—C15—H15A	109.00
C2—C1—H1B	109.00	C16—C15—H15B	109.00
H1A—C1—H1B	108.00	H15A—C15—H15B	108.00
O1—C2—H2A	109.00	N3—C16—H16A	110.00
O1—C2—H2B	109.00	N3—C16—H16B	110.00
C1—C2—H2A	109.00	C15—C16—H16A	110.00
C1—C2—H2B	109.00	C15—C16—H16B	110.00
H2A—C2—H2B	108.00	H16A—C16—H16B	108.00
O1—C3—H3A	109.00

C2—O1—C3—C4	−59.1 (3)	N1—C5—C6—C7	−158.0 (2)
C3—O1—C2—C1	58.2 (3)	C5—C6—C11—C10	177.2 (2)
C14—O3—C15—C16	60.8 (3)	C11—C6—C7—O2	176.9 (2)
C15—O3—C14—C13	−61.0 (3)	C5—C6—C7—O2	0.6 (3)
C1—N1—C4—C3	−55.5 (3)	C7—C6—C11—C10	1.0 (3)
C4—N1—C1—C2	55.8 (3)	C11—C6—C7—C8	−1.0 (3)
C5—N1—C4—C3	−178.0 (2)	C5—C6—C7—C8	−177.3 (2)
C1—N1—C5—C6	78.8 (2)	O2—C7—C8—C9	−177.62 (19)
C4—N1—C5—C6	−160.1 (2)	O2—C7—C8—C12	−1.0 (3)
C5—N1—C1—C2	177.6 (2)	C6—C7—C8—C12	176.8 (2)
C12—N2—N3—C16	17.4 (3)	C6—C7—C8—C9	0.2 (3)
C12—N2—N3—C13	146.5 (2)	C7—C8—C12—N2	−2.9 (3)
N3—N2—C12—C8	−179.97 (19)	C12—C8—C9—C10	−176.1 (2)
C13—N3—C16—C15	50.3 (3)	C7—C8—C9—C10	0.6 (3)
N2—N3—C13—C14	176.21 (18)	C9—C8—C12—N2	173.7 (2)
C16—N3—C13—C14	−52.5 (3)	C8—C9—C10—C11	−0.6 (4)
N2—N3—C16—C15	177.92 (19)	C9—C10—C11—C6	−0.3 (4)
N1—C1—C2—O1	−58.0 (3)	N3—C13—C14—O3	57.5 (3)
O1—C3—C4—N1	58.4 (3)	O3—C15—C16—N3	−55.1 (3)
N1—C5—C6—C11	25.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C6–C11 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.91	2.636 (2)	146
C13—H13A···O3ⁱ	0.97	2.55	3.416 (3)	149
C4—H4A···Cg3ⁱ	0.97	2.87	3.646 (3)	138

Symmetry code: (i) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C6–C11 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.91	2.636 (2)	146
C13—H13A···O3ⁱ	0.97	2.55	3.416 (3)	149
C4—H4A···Cg3ⁱ	0.97	2.87	3.646 (3)	138

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

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