(E)-2-{[(Furan-2-ylmeth­yl)imino]­meth­yl}-4-nitro­phenol

Hijji, Y.; Azemati, S.; Butcher, R.J.; Jasinski, J.P.

doi:10.1107/S1600536814005583

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages o451-o452

doi:10.1107/S1600536814005583

Open

access

(E)-2-{[(Furan-2-ylmethyl)imino]methyl}-4-nitrophenol

Yousef Hijji,^a ‡ Samira Azemati,^a Ray J. Butcher ^b ^* and Jerry P. Jasinski ^c

^aChemistry Department, Morgan State University, 1700 East Cold Spring Lane, Baltimore, MD 21251, USA, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^cDepartment of Chemistry, Keene State College, Keene, NH 03410, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 26 February 2014; accepted 11 March 2014; online 15 March 2014)

In the title compound, C₁₂H₁₀N₂O₄, the furan-2-ylmethyl group is disordered over two sets of sites, with refined occupancies of 0.858 (3) and 0.143 (3). In the major component of disorder, the dihedral angle between the furan and benzene rings is 63.1 (2)° and for the minor component this value is 67.9 (6)°. The planes of the nitro group and the attached benzene ring form a dihedral angle of 4.34 (17)°. In the crystal, inversion-related molecules are linked by two pairs of weak C—H⋯O interactions, one involving the nitro group and the other involving the O—H group as an acceptor. As a result of these associations, ribbons are formed along [120]. A strong intramolecular O—H⋯N hydrogen bond is observed.

CCDC reference: 991243

Related literature

For the use of salicylidene compounds as anion sensors, see: Hijji et al. (2009 ) and for the use of related compounds as anion sensors, see: Hijji et al. (2004 ). For the bioactivity of metal complexes of structurally related salicylidene derivatives, see: Mandal et al. (2009a ,b ). For related structures, see: Song et al. (2008 ); Khalaji et al. (2011a ,b ).

Experimental

Crystal data

C₁₂H₁₀N₂O₄
M_r = 246.22
Triclinic, $[P \overline 1]$
a = 5.4427 (7) Å
b = 8.2488 (10) Å
c = 12.4701 (14) Å
α = 98.901 (9)°
β = 92.04 (1)°
γ = 91.69 (1)°
V = 552.41 (12) Å³
Z = 2
Cu Kα radiation
μ = 0.96 mm⁻¹
T = 123 K
0.34 × 0.26 × 0.17 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.912, T_max = 1.000
3400 measured reflections
2210 independent reflections
2047 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.122
S = 1.06
2210 reflections
186 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2	0.95 (3)	1.72 (3)	2.5784 (14)	148 (2)
C2—H2A⋯O1ⁱ	0.95	2.52	3.4548 (16)	169
C7—H7A⋯O3ⁱⁱ	0.95	2.54	3.4567 (16)	161
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 991243

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814005583/lh5694sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814005583/lh5694Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814005583/lh5694Isup3.cml

checkCIF report

Comment top

The title compound adopts an E configuration with respect to the C═N imine bond. Structurally related salicylidene derivatives have been used as anion sensors (Hijji, et al., 2004; Hijji et al., 2009) and their metal complexes have shown bioactivity (Mandal et al., 2009a,b). Similar structures have been previously reported (Song et al., 2008; Khalaji et al., 2011a,b).

The molecular structure of the title compound is shown in Fig. 1. The furan-2-ylmethyl group is disordered over two sets of sites with refined occupancies of 0.858 (3) and 0.142 (3). In the major component of disorder the dihedral angle between the furan and benzene rings is 63.1 (2)° and for the minor component this value is 67.9 (6)°. The nitro group and attached benzene ring form a dihedral angle of 4.34 (17)°. In the crystal, inversion related molecules are linked by two pairs of weak C—H···O interactions, one involves the nitro group while the other involves the O—H as an acceptor (Fig. 2). As a result of these associations ribbons are formed along [120]. A strong intramolecular O—H···N hydrogen bond is observed.

Experimental top

((E)-2-(((Furan-2-ylmethyl)imino)methyl)-4-nitrophenol was synthesized by mixing 2-methylfurylamine (0.29 g, 3mmol) with 5-nitro-2-hydroxybenzaldehyde. (0.32 g, 2 mmol) the mixture was mixed well and turned dark yellow. After mixing and grinding for 5 minutes the mixture was dissolved in 15 mL of diethyl ether and allowed to crystallize to give yellow crystals, 0.378g, 77% yield), m.p. (393-395 K). A sample was recrystallized from diethyl ether with slow evaporation to provide a crystal suitable for x-ray measurements.

Refinement top

H atoms were placed in geometrically idealized positions with a C—H distances of 0.95 and 0.99 Å Uĩso~(H) = 1.2U~eq~(C) and 0.96 Å for CH~3~ [Uĩso~(H) = 1.5U~eq~(C)]. The furan ring was refined as disordered over two conformations. Both components were constrained to have similar geometries with occupancies of 0.858 (3) and 0.142 (3). For the hydroxy group the H atom was refined isotropically.

Related literature top

For the use of salicylidene compounds as anion sensors, see: Hijji et al. (2009) and for the use of related compounds as anion sensors, see: Hijji et al. (2004). For the bioactivity of metal complexes of structurally related salicylidene derivatives, see: Mandal et al. (2009a,b). For related structures, see: Song et al. (2008); Khalaji et al. (2011a,b).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing ellipsoids at the 30% probabilty level (major component only). The dashed line indicates a hydrogen bond.
	Fig. 2. Packing diagram for the complex viewed along the c axis showing the repeating motif forming ribbons along [1 2 0]. N—H···O hydrogen bonds and C—H···O interactions shown by dashed lines.

(E)-2-{[(Furan-2-ylmethyl)imino]methyl}-4-nitrophenol top

Crystal data top

C₁₂H₁₀N₂O₄	Z = 2
M_r = 246.22	F(000) = 256
Triclinic, P1	D_x = 1.480 Mg m⁻³
a = 5.4427 (7) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.2488 (10) Å	Cell parameters from 2639 reflections
c = 12.4701 (14) Å	θ = 3.6–75.5°
α = 98.901 (9)°	µ = 0.96 mm⁻¹
β = 92.04 (1)°	T = 123 K
γ = 91.69 (1)°	Prism, pale yellow
V = 552.41 (12) Å³	0.34 × 0.26 × 0.17 mm

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	2047 reflections with I > 2σ(I)
Detector resolution: 10.5081 pixels mm^-1	R_int = 0.019
ω scans	θ_max = 75.6°, θ_min = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −6→6
T_min = 0.912, T_max = 1.000	k = −10→10
3400 measured reflections	l = −11→15
2210 independent 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0764P)² + 0.0922P] where P = (F_o² + 2F_c²)/3
2210 reflections	(Δ/σ)_max < 0.001
186 parameters	Δρ_max = 0.32 e Å⁻³
13 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₂H₁₀N₂O₄	γ = 91.69 (1)°
M_r = 246.22	V = 552.41 (12) Å³
Triclinic, P1	Z = 2
a = 5.4427 (7) Å	Cu Kα radiation
b = 8.2488 (10) Å	µ = 0.96 mm⁻¹
c = 12.4701 (14) Å	T = 123 K
α = 98.901 (9)°	0.34 × 0.26 × 0.17 mm
β = 92.04 (1)°

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	2210 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2047 reflections with I > 2σ(I)
T_min = 0.912, T_max = 1.000	R_int = 0.019
3400 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	13 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.32 e Å⁻³
2210 reflections	Δρ_min = −0.27 e Å⁻³
186 parameters

Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

¹H-NMR (400 MHz): d ppm (CDCl₃): 14.41(br. s 1H), 8.39 (t, J = 1.25 Hz, 1H) 8.255 (d, J = 2.85 Hz, 1H), 8.205 (dd, J = 8.25, 2.85 Hz, 1H), 7.44 ( dd, J = 1.75, 0.75 Hz, 1H), 7.01 ( d, J = 7.30 Hz, 1H), 6.395 (dd, J = 3.45, 1.85 Hz, 1H), 6.35 dt, J = 3.45, 0.75 Hz, 1 H), 4.84 (s, 2 H). ¹³C-NMR (100 MHz) d ppm (CDCl₃): 167.64, 164.96, 149.57, 143.12, 139.45, 128.23, 128.08, 118.46, 117.44, 110.05, 108.99, 54.01. Mass spec: M⁺ = 246.

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.24922 (16)	0.42490 (11)	0.60178 (7)	0.0282 (2)
H1O	0.352 (5)	0.424 (3)	0.665 (2)	0.082 (8)*
O2	0.51829 (18)	0.00193 (12)	0.16611 (7)	0.0345 (2)
O3	0.83082 (19)	−0.04412 (13)	0.26772 (8)	0.0406 (3)
N1	0.6361 (2)	0.02267 (13)	0.25331 (9)	0.0281 (2)
N2	0.6077 (2)	0.34958 (13)	0.72346 (8)	0.0281 (2)
C1	0.3478 (2)	0.33032 (14)	0.51862 (9)	0.0226 (2)
C2	0.2310 (2)	0.31430 (15)	0.41515 (10)	0.0244 (2)
H2A	0.0863	0.3727	0.4049	0.029*
C3	0.3249 (2)	0.21438 (14)	0.32834 (9)	0.0242 (2)
H3A	0.2450	0.2024	0.2585	0.029*
C4	0.5397 (2)	0.13099 (14)	0.34469 (9)	0.0233 (2)
C5	0.6607 (2)	0.14649 (14)	0.44537 (10)	0.0240 (2)
H5A	0.8072	0.0893	0.4542	0.029*
C6	0.5667 (2)	0.24627 (14)	0.53369 (9)	0.0222 (2)
C7	0.6911 (2)	0.26050 (14)	0.64088 (10)	0.0256 (3)
H7A	0.8368	0.2022	0.6491	0.031*
O4	0.6949 (2)	0.62761 (19)	0.92624 (12)	0.0322 (3)	0.858 (3)
C8	0.7459 (4)	0.3535 (3)	0.8281 (2)	0.0320 (5)	0.858 (3)
H8A	0.8813	0.2757	0.8180	0.038*	0.858 (3)
H8B	0.6350	0.3170	0.8816	0.038*	0.858 (3)
C9	0.8503 (5)	0.5208 (3)	0.8716 (3)	0.0253 (3)	0.858 (3)
C10	1.0759 (3)	0.5895 (2)	0.87026 (14)	0.0297 (4)	0.858 (3)
H10A	1.2147	0.5405	0.8362	0.036*	0.858 (3)
C11	1.0658 (4)	0.7526 (2)	0.93068 (14)	0.0318 (4)	0.858 (3)
H11A	1.1970	0.8325	0.9449	0.038*	0.858 (3)
C12	0.8342 (4)	0.76926 (19)	0.96289 (13)	0.0328 (4)	0.858 (3)
H12A	0.7744	0.8649	1.0049	0.039*	0.858 (3)
O4A	0.7528 (18)	0.6486 (14)	0.9445 (9)	0.0322 (3)	0.142 (3)
C8A	0.694 (3)	0.3590 (19)	0.8374 (16)	0.0320 (5)	0.142 (3)
H8A1	0.8057	0.2681	0.8444	0.038*	0.142 (3)
H8A2	0.5526	0.3481	0.8836	0.038*	0.142 (3)
C9A	0.827 (3)	0.519 (2)	0.8736 (17)	0.0253 (3)	0.142 (3)
C10A	1.0441 (18)	0.5434 (14)	0.8316 (9)	0.0297 (4)	0.142 (3)
H10B	1.1253	0.4736	0.7772	0.036*	0.142 (3)
C11A	1.1230 (19)	0.6970 (14)	0.8873 (9)	0.0318 (4)	0.142 (3)
H11B	1.2789	0.7477	0.8793	0.038*	0.142 (3)
C12A	0.950 (3)	0.7651 (13)	0.9539 (9)	0.0328 (4)	0.142 (3)
H12B	0.9601	0.8700	0.9981	0.039*	0.142 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0281 (4)	0.0311 (4)	0.0245 (4)	0.0086 (3)	0.0018 (3)	0.0001 (3)
O2	0.0409 (5)	0.0361 (5)	0.0247 (4)	0.0025 (4)	0.0013 (4)	−0.0014 (4)
O3	0.0365 (5)	0.0429 (6)	0.0409 (5)	0.0172 (4)	0.0048 (4)	−0.0024 (4)
N1	0.0291 (5)	0.0253 (5)	0.0298 (5)	0.0021 (4)	0.0052 (4)	0.0034 (4)
N2	0.0347 (5)	0.0247 (5)	0.0245 (5)	0.0003 (4)	−0.0056 (4)	0.0040 (4)
C1	0.0220 (5)	0.0210 (5)	0.0252 (5)	0.0008 (4)	0.0021 (4)	0.0048 (4)
C2	0.0205 (5)	0.0249 (5)	0.0283 (6)	0.0036 (4)	−0.0002 (4)	0.0059 (4)
C3	0.0243 (5)	0.0261 (5)	0.0229 (5)	−0.0002 (4)	−0.0010 (4)	0.0063 (4)
C4	0.0246 (5)	0.0203 (5)	0.0249 (6)	0.0009 (4)	0.0038 (4)	0.0027 (4)
C5	0.0212 (5)	0.0209 (5)	0.0308 (6)	0.0030 (4)	0.0016 (4)	0.0067 (4)
C6	0.0225 (5)	0.0202 (5)	0.0244 (5)	0.0003 (4)	−0.0007 (4)	0.0054 (4)
C7	0.0263 (5)	0.0211 (5)	0.0299 (6)	0.0011 (4)	−0.0047 (4)	0.0064 (4)
O4	0.0284 (7)	0.0340 (6)	0.0326 (7)	0.0038 (5)	0.0018 (5)	−0.0002 (5)
C8	0.0410 (13)	0.0279 (6)	0.0266 (8)	0.0046 (8)	−0.0087 (8)	0.0042 (5)
C9	0.0277 (8)	0.0287 (6)	0.0195 (5)	0.0067 (5)	−0.0021 (5)	0.0030 (4)
C10	0.0246 (7)	0.0411 (10)	0.0230 (8)	0.0050 (6)	0.0016 (6)	0.0032 (7)
C11	0.0386 (9)	0.0338 (9)	0.0222 (8)	−0.0078 (7)	−0.0049 (7)	0.0047 (6)
C12	0.0441 (10)	0.0261 (7)	0.0268 (7)	0.0069 (7)	−0.0003 (7)	−0.0011 (5)
O4A	0.0284 (7)	0.0340 (6)	0.0326 (7)	0.0038 (5)	0.0018 (5)	−0.0002 (5)
C8A	0.0410 (13)	0.0279 (6)	0.0266 (8)	0.0046 (8)	−0.0087 (8)	0.0042 (5)
C9A	0.0277 (8)	0.0287 (6)	0.0195 (5)	0.0067 (5)	−0.0021 (5)	0.0030 (4)
C10A	0.0246 (7)	0.0411 (10)	0.0230 (8)	0.0050 (6)	0.0016 (6)	0.0032 (7)
C11A	0.0386 (9)	0.0338 (9)	0.0222 (8)	−0.0078 (7)	−0.0049 (7)	0.0047 (6)
C12A	0.0441 (10)	0.0261 (7)	0.0268 (7)	0.0069 (7)	−0.0003 (7)	−0.0011 (5)

Geometric parameters (Å, º) top

O1—C1	1.3363 (14)	C8—C9	1.491 (3)
O1—H1O	0.95 (3)	C8—H8A	0.9900
O2—N1	1.2286 (15)	C8—H8B	0.9900
O3—N1	1.2289 (15)	C9—C10	1.339 (3)
N1—C4	1.4586 (15)	C10—C11	1.440 (3)
N2—C7	1.2747 (17)	C10—H10A	0.9500
N2—C8A	1.47 (2)	C11—C12	1.341 (3)
N2—C8	1.479 (3)	C11—H11A	0.9500
C1—C2	1.4036 (16)	C12—H12A	0.9500
C1—C6	1.4172 (16)	O4A—C9A	1.359 (14)
C2—C3	1.3788 (17)	O4A—C12A	1.410 (14)
C2—H2A	0.9500	C8A—C9A	1.483 (14)
C3—C4	1.3982 (17)	C8A—H8A1	0.9900
C3—H3A	0.9500	C8A—H8A2	0.9900
C4—C5	1.3830 (17)	C9A—C10A	1.333 (14)
C5—C6	1.3917 (17)	C10A—C11A	1.395 (12)
C5—H5A	0.9500	C10A—H10B	0.9500
C6—C7	1.4633 (16)	C11A—C12A	1.354 (13)
C7—H7A	0.9500	C11A—H11B	0.9500
O4—C9	1.362 (3)	C12A—H12B	0.9500
O4—C12	1.381 (2)

C1—O1—H1O	108.3 (17)	H8A—C8—H8B	107.9
O2—N1—O3	123.29 (11)	C10—C9—O4	111.09 (19)
O2—N1—C4	118.49 (10)	C10—C9—C8	132.3 (2)
O3—N1—C4	118.22 (11)	O4—C9—C8	116.55 (19)
C7—N2—C8A	127.0 (7)	C9—C10—C11	106.24 (16)
C7—N2—C8	116.83 (12)	C9—C10—H10A	126.9
O1—C1—C2	119.08 (10)	C11—C10—H10A	126.9
O1—C1—C6	120.99 (10)	C12—C11—C10	106.29 (14)
C2—C1—C6	119.92 (11)	C12—C11—H11A	126.9
C3—C2—C1	120.40 (11)	C10—C11—H11A	126.9
C3—C2—H2A	119.8	C11—C12—O4	110.34 (14)
C1—C2—H2A	119.8	C11—C12—H12A	124.8
C2—C3—C4	119.02 (11)	O4—C12—H12A	124.8
C2—C3—H3A	120.5	C9A—O4A—C12A	104.9 (10)
C4—C3—H3A	120.5	N2—C8A—C9A	109.4 (15)
C5—C4—C3	121.81 (11)	N2—C8A—H8A1	109.8
C5—C4—N1	119.21 (10)	C9A—C8A—H8A1	109.8
C3—C4—N1	118.97 (11)	N2—C8A—H8A2	109.8
C4—C5—C6	119.65 (11)	C9A—C8A—H8A2	109.8
C4—C5—H5A	120.2	H8A1—C8A—H8A2	108.2
C6—C5—H5A	120.2	C10A—C9A—O4A	114.2 (11)
C5—C6—C1	119.19 (11)	C10A—C9A—C8A	117.8 (13)
C5—C6—C7	119.90 (10)	O4A—C9A—C8A	128.0 (13)
C1—C6—C7	120.90 (11)	C9A—C10A—C11A	102.9 (10)
N2—C7—C6	121.28 (11)	C9A—C10A—H10B	128.6
N2—C7—H7A	119.4	C11A—C10A—H10B	128.6
C6—C7—H7A	119.4	C12A—C11A—C10A	111.8 (9)
C9—O4—C12	106.02 (16)	C12A—C11A—H11B	124.1
N2—C8—C9	112.0 (2)	C10A—C11A—H11B	124.1
N2—C8—H8A	109.2	C11A—C12A—O4A	106.0 (9)
C9—C8—H8A	109.2	C11A—C12A—H12B	127.0
N2—C8—H8B	109.2	O4A—C12A—H12B	127.0
C9—C8—H8B	109.2

O1—C1—C2—C3	−178.40 (10)	C8A—N2—C8—C9	−94 (3)
C6—C1—C2—C3	1.40 (18)	C12—O4—C9—C10	−1.4 (3)
C1—C2—C3—C4	−0.77 (18)	C12—O4—C9—C8	177.1 (3)
C2—C3—C4—C5	−0.24 (18)	N2—C8—C9—C10	−100.0 (4)
C2—C3—C4—N1	178.74 (10)	N2—C8—C9—O4	81.9 (3)
O2—N1—C4—C5	175.41 (10)	O4—C9—C10—C11	1.2 (3)
O3—N1—C4—C5	−4.15 (17)	C8—C9—C10—C11	−177.0 (4)
O2—N1—C4—C3	−3.60 (17)	C9—C10—C11—C12	−0.4 (2)
O3—N1—C4—C3	176.84 (11)	C10—C11—C12—O4	−0.44 (18)
C3—C4—C5—C6	0.62 (18)	C9—O4—C12—C11	1.1 (2)
N1—C4—C5—C6	−178.37 (10)	C7—N2—C8A—C9A	108.4 (12)
C4—C5—C6—C1	0.02 (17)	C8—N2—C8A—C9A	74 (3)
C4—C5—C6—C7	178.74 (10)	C12A—O4A—C9A—C10A	−4 (2)
O1—C1—C6—C5	178.78 (10)	C12A—O4A—C9A—C8A	177 (2)
C2—C1—C6—C5	−1.01 (17)	N2—C8A—C9A—C10A	−70 (2)
O1—C1—C6—C7	0.07 (17)	N2—C8A—C9A—O4A	109 (2)
C2—C1—C6—C7	−179.72 (10)	O4A—C9A—C10A—C11A	5 (2)
C8A—N2—C7—C6	171.7 (8)	C8A—C9A—C10A—C11A	−176.2 (18)
C8—N2—C7—C6	179.22 (13)	C9A—C10A—C11A—C12A	−4.2 (16)
C5—C6—C7—N2	−179.25 (11)	C10A—C11A—C12A—O4A	2.1 (13)
C1—C6—C7—N2	−0.55 (18)	C9A—O4A—C12A—C11A	0.9 (16)
C7—N2—C8—C9	116.69 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.95 (3)	1.72 (3)	2.5784 (14)	148 (2)
C2—H2A···O1ⁱ	0.95	2.52	3.4548 (16)	169
C7—H7A···O3ⁱⁱ	0.95	2.54	3.4567 (16)	161

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.95 (3)	1.72 (3)	2.5784 (14)	148 (2)
C2—H2A···O1ⁱ	0.95	2.52	3.4548 (16)	168.7
C7—H7A···O3ⁱⁱ	0.95	2.54	3.4567 (16)	161.0

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

Footnotes

‡Current Address: Department of Chemistry and Earth Sciences, Qatar University, PO Box 2713, Doha, Qatar.

Acknowledgements

RJB wishes to acknowledge the National Science Foundation MRI program (CHE0619278) for funds to purchase the diffractometer and the Howard University Nanoscience Facility for access to liquid nitrogen. YH would like to thank the Department of Chemistry and Earth Sciences at Qatar University for support.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Hijji, Y. M., Barare, B., Kennedy, A. P. & Butcher, R. (2009). Sens. Actuators B, 136, 297–302. Web of Science CrossRef CAS Google Scholar
Hijji, Y. M., Wairia, G., Edwards, A., Iwunze, M., Kennedy Sr, A. & Williams, R. (2004). Progress in Biomedical Optics and Imaging – Proceedings of SPIE, Vol. 5588, pp. 29, 214–223. Google Scholar
Khalaji, A. D., Maghsod, L., Rad, S., Grivani, G., Rezaei, M., Gotoh, K. & Ishida, H. (2011a). Chin. J. Chem. 29, 1613–1616. . Web of Science CSD CrossRef CAS Google Scholar
Khalaji, A. D., Rad, S. M., Grivani, G. & Das, D. (2011b). J. Therm. Anal. Calorim. 103, 747–751. Web of Science CrossRef CAS Google Scholar
Mandal, S., Rout, A. K., Ghosh, A., Pilet, G. & Bandyopadhyay, D. (2009a). Polyhedron, 28, 3858–3862. Web of Science CSD CrossRef CAS Google Scholar
Mandal, S., Rout, A. K., Pilet, G. & Bandyopadhyay, D. (2009b). Transition Met. Chem. 34, 719–724. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, Y., Xu, Z., Sun, Q., Su, B., Gao, Q., Liu, H. & Zhao, J. (2008). J. Coord. Chem. 61, 1212–1220. Web of Science CSD CrossRef CAS 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 70| Part 4| April 2014| Pages o451-o452

doi:10.1107/S1600536814005583

Open

access