2-Amino-N-(2-hydr­oxy-3-methoxy­benzyl­idene)aniline

Al-Douh, M.H.; Hamid, S.A.; Osman, H.; Kia, R.; Fun, H.-K.

doi:10.1107/S1600536808016292

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages o1201-o1202

doi:10.1107/S1600536808016292

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2-Amino-N-(2-hydroxy-3-methoxybenzylidene)aniline

Mohammed H. Al-Douh,^a Shafida A. Hamid,^a ‡ Hasnah Osman,^a Reza Kia ^b and Hoong-Kun Fun ^b ^*

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 24 May 2008; accepted 29 May 2008; online 7 June 2008)

In the title compound, C₁₄H₁₄N₂O₂, the dihedral angle between the two benzene rings is 9.67 (10)°. Two intramolecular O—H⋯N and N—H⋯N hydrogen bonds involving the hydroxy and amino groups generate S(6) and S(5) ring motifs, respectively. In the crystal structure, N—H⋯O hydrogen bonds link neighboring molecules. Molecules are also stacked in a head-to-tail fashion along the c axis through π–π interactions [centroid–centroid separation of 3.7357 (12) Å] and are further linked by weak intermolecular C—H⋯π interactions, giving a zigzag arrangement along the b axis.

Related literature

For related literature on hydrogen bond motifs, see: Bernstein et al. (1995 ). For values of bond lengths, see: Allen et al. (1987 ). For the biological activity of imines, see, for example: Singh & Dash (1988 ); More et al. (2001 ); Baseer et al. (2000 ); El-Masry et al. (2000 ); Kabeer et al. (2001 ); Kuz'min et al. (2000 ); Desai et al. (2001 ). For related structures, see, for example: Corden et al. (1996 ); Govindasamy et al. (1999 ). For synthesis, see: Al-Douh et al. (2006 , 2007 ). For related literature, see: Berger (2001 ); Elerman & Kabak (1997 ); Latif et al. (1983 ); Liu et al. (2006 ); Shah et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₂
M_r = 242.27
Monoclinic, P 2₁ /c
a = 13.2790 (6) Å
b = 14.4810 (6) Å
c = 6.1928 (3) Å
β = 103.116 (3)°
V = 1159.77 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100.0 (1) K
0.45 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.959, T_max = 0.996
19968 measured reflections
3402 independent reflections
2532 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.206
S = 1.06
3402 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.88	1.77	2.602 (2)	158
N2—H1N2⋯O1ⁱ	0.93 (3)	2.56 (3)	3.030 (3)	111 (2)
N2—H1N2⋯O2ⁱ	0.93 (3)	2.29 (3)	3.181 (3)	161 (3)
N2—H2N2⋯N1	0.87 (3)	2.23 (3)	2.759 (3)	119 (2)
C3—H3⋯Cg1ⁱⁱ	0.94 (3)	2.64 (3)	3.458 (2)	145 (2)
C11—H11⋯Cg2ⁱⁱⁱ	0.91 (3)	2.87 (3)	3.538 (2)	142 (2)
Symmetry codes: (i) -x, -y+2, -z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016292/sj2510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016292/sj2510Isup2.hkl

checkCIF report

Comment top

Imines are an important class of compounds and rank among the most versatile synthetic organic intermediates, which are important for the synthesis of biologically important compounds (Singh & Dash, 1988; More et al., 2001; Baseer et al., 2000; El-Masry et al., 2000; Kabeer et al., 2001; Kuz'min et al., 2000; Desai et al., 2001). Berger (2001) evaluated some bis-Schiff bases using 1138 and Sc-7 yeast assays, and a A2780 cytotoxicity test. They showed significant activity in a single dose test. The reactions of some phenolic aldehydes with o-phenylenediamine have been examined in some detail including the isolation of the title compound (Latif et al., 1983). Our group has been actively involved in synthesizing bis-Schiff bases and investigating their DNA binding ability using spectroscopic techniques employing calf thymus DNA (Shah et al., 2008). We have also obtained single crystals of benzimidazole and the bis-Schiff base derived from the title compound (I) and their structures are consistent with those reported earlier (Elerman & Kabak, 1997; Liu et al., 2006). However, the crystal structure of compound (I) was never reported and we present its structure here (Fig. 1).

The C1–C6 benzene ring is not coplanar with the phenylenediamine and makes a dihedral angle of 9.67 (10)° with C8–C13 benzene ring. Two intramolecular O1—H1O1···N1 and N2—H2N2···N1 hydrogen bonds generate S(6) and S(5) ring motifs, respectively (Bernstein et al., 1995). Bond lengths and angles in the title compound have normal values (Allen et al., 1987). The crystal is stabilized by intramolecular O—H···N and N—H···N and intermolecular N—H···O hydrogen bonds. Molecules (Fig. 2) are also arranged into zig-zag chains by C—H···π interactions along the b-axis (Table 1); Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 phenyl rings, respectively. In the crystal packing (Fig. 3), molecules are stacked along the c axis by π···π interactions with Cg1···Cg2 = 3.7357 (12) Å: symmetry codes x, y, -1 + z and x, y, 1 + z;

Related literature top

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For values of bond lengths and angles, see: Allen et al. (1987). For the biological activity of imines, see, for example: Singh & Dash (1988); More et al. (2001); Baseer et al. (2000); El-Masry et al. (2000); Kabeer et al. (2001); Kuz'min et al. (2000); Desai et al. (2001). For related structures, see, for example: Corden et al. (1996); Govindasamy et al. (1999). For synthesis, see: Al-Douh et al. (2006, 2007). For related literature, see: Berger (2001); Elerman & Kabak (1997); Latif et al. (1983); Liu et al. (2006); Shah et al. (2008).

Experimental top

The synthetic method has been described earlier (Al-Douh et al., 2006, 2007). Single crystals suitable for X-ray diffraction were obtained by evaporation of a n-hexane solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Intramolecular H bonds are drawn as dashed lines.
	Fig. 2. The crystal packing of (I) showing the zigzag stacking arrangement along the b axis. H bonds are drawn as dashed lines.
	Fig. 3. The crystal packing of (I), viewed along the c axis showing the molecular stacking. H bonds are drawn as dashed lines.

2-Amino-N-(2-hydroxy-3-methoxybenzylidene)aniline top

Crystal data top

C₁₄H₁₄N₂O₂	F(000) = 512
M_r = 242.27	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4220 reflections
a = 13.2790 (6) Å	θ = 2.8–29.4°
b = 14.4810 (6) Å	µ = 0.09 mm⁻¹
c = 6.1928 (3) Å	T = 100 K
β = 103.116 (3)°	Needle, yellow
V = 1159.77 (9) Å³	0.45 × 0.15 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3402 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −18→18
T_min = 0.959, T_max = 0.996	k = −20→20
19968 measured reflections	l = −8→8

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.206	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.099P)² + 1.0519P] where P = (F_o² + 2F_c²)/3
3402 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₂	V = 1159.77 (9) Å³
M_r = 242.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2790 (6) Å	µ = 0.09 mm⁻¹
b = 14.4810 (6) Å	T = 100 K
c = 6.1928 (3) Å	0.45 × 0.15 × 0.05 mm
β = 103.116 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3402 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2532 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.996	R_int = 0.052
19968 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.206	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.66 e Å⁻³
3402 reflections	Δρ_min = −0.31 e Å⁻³
194 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.12067 (11)	1.03082 (11)	0.3256 (2)	0.0223 (4)
H1O1	0.1550	1.0024	0.2388	0.027*
O2	0.07156 (12)	1.12650 (11)	0.6488 (3)	0.0227 (4)
N1	0.26011 (14)	0.97668 (12)	0.1182 (3)	0.0184 (4)
N2	0.10257 (15)	0.90586 (15)	−0.2092 (3)	0.0251 (4)
H1N2	0.058 (2)	0.909 (2)	−0.349 (5)	0.030*
H2N2	0.110 (2)	0.954 (2)	−0.124 (5)	0.030*
C1	0.20451 (16)	0.89186 (15)	−0.2205 (3)	0.0192 (4)
C2	0.22641 (18)	0.83919 (16)	−0.3939 (4)	0.0225 (4)
H2	0.165 (2)	0.8218 (19)	−0.497 (5)	0.027*
C3	0.32708 (19)	0.82255 (14)	−0.4076 (4)	0.0219 (5)
H3	0.339 (2)	0.7874 (19)	−0.528 (5)	0.026*
C4	0.40918 (18)	0.85597 (15)	−0.2452 (4)	0.0216 (4)
H4	0.477 (2)	0.8429 (19)	−0.253 (4)	0.026*
C5	0.38917 (17)	0.90701 (14)	−0.0713 (4)	0.0196 (4)
H5	0.447 (2)	0.9297 (18)	0.037 (5)	0.024*
C6	0.28785 (16)	0.92618 (14)	−0.0560 (3)	0.0168 (4)
C7	0.32762 (16)	1.02164 (14)	0.2604 (3)	0.0192 (4)
H7	0.403 (2)	1.0240 (18)	0.247 (4)	0.023*
C8	0.30011 (16)	1.07288 (14)	0.4405 (3)	0.0174 (4)
C9	0.37772 (17)	1.11996 (14)	0.5926 (4)	0.0195 (4)
H9	0.449 (2)	1.1215 (18)	0.569 (4)	0.023*
C10	0.35346 (17)	1.16977 (14)	0.7632 (4)	0.0196 (4)
H10	0.407 (2)	1.2018 (18)	0.862 (5)	0.024*
C11	0.25165 (17)	1.17414 (14)	0.7875 (3)	0.0189 (4)
H11	0.238 (2)	1.2072 (18)	0.902 (5)	0.023*
C12	0.17424 (16)	1.12778 (14)	0.6423 (3)	0.0177 (4)
C13	0.19759 (15)	1.07615 (14)	0.4659 (3)	0.0170 (4)
C14	0.04456 (18)	1.17522 (17)	0.8283 (4)	0.0263 (5)
H14A	0.0835	1.1510	0.9665	0.039*
H14B	−0.0280	1.1678	0.8209	0.039*
H14C	0.0600	1.2396	0.8181	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0173 (7)	0.0307 (8)	0.0180 (7)	−0.0022 (6)	0.0024 (6)	−0.0069 (6)
O2	0.0202 (8)	0.0294 (8)	0.0203 (7)	−0.0001 (6)	0.0081 (6)	−0.0067 (6)
N1	0.0189 (8)	0.0220 (9)	0.0144 (8)	0.0017 (7)	0.0042 (7)	0.0003 (6)
N2	0.0188 (9)	0.0345 (11)	0.0220 (10)	0.0020 (8)	0.0045 (8)	−0.0037 (8)
C1	0.0186 (10)	0.0229 (10)	0.0166 (9)	0.0026 (7)	0.0052 (8)	0.0020 (8)
C2	0.0253 (11)	0.0247 (10)	0.0156 (10)	−0.0014 (8)	0.0009 (8)	−0.0010 (8)
C3	0.0354 (12)	0.0175 (10)	0.0149 (9)	0.0024 (8)	0.0103 (9)	−0.0014 (7)
C4	0.0214 (10)	0.0217 (10)	0.0245 (11)	0.0023 (8)	0.0110 (9)	0.0031 (8)
C5	0.0182 (10)	0.0201 (9)	0.0196 (10)	−0.0015 (8)	0.0026 (8)	0.0005 (8)
C6	0.0219 (10)	0.0163 (9)	0.0126 (9)	0.0008 (7)	0.0045 (7)	0.0003 (7)
C7	0.0203 (10)	0.0207 (10)	0.0174 (10)	0.0007 (8)	0.0056 (8)	0.0022 (7)
C8	0.0200 (10)	0.0176 (9)	0.0154 (9)	0.0026 (7)	0.0054 (7)	0.0014 (7)
C9	0.0171 (10)	0.0220 (10)	0.0195 (10)	0.0003 (8)	0.0042 (8)	0.0032 (8)
C10	0.0205 (10)	0.0195 (9)	0.0168 (10)	−0.0020 (8)	0.0000 (8)	0.0002 (8)
C11	0.0258 (11)	0.0175 (9)	0.0139 (9)	0.0013 (8)	0.0055 (8)	−0.0014 (7)
C12	0.0165 (9)	0.0211 (9)	0.0161 (9)	0.0027 (7)	0.0049 (7)	0.0019 (7)
C13	0.0178 (10)	0.0188 (9)	0.0130 (9)	−0.0004 (7)	0.0003 (7)	0.0006 (7)
C14	0.0252 (11)	0.0362 (13)	0.0194 (11)	0.0023 (9)	0.0095 (9)	−0.0055 (9)

Geometric parameters (Å, º) top

O1—C13	1.351 (2)	C5—C6	1.398 (3)
O1—H1O1	0.8812	C5—H5	0.95 (3)
O2—C12	1.373 (2)	C7—C8	1.454 (3)
O2—C14	1.429 (3)	C7—H7	1.03 (3)
N1—C7	1.282 (3)	C8—C9	1.405 (3)
N1—C6	1.419 (3)	C8—C13	1.406 (3)
N2—C1	1.386 (3)	C9—C10	1.376 (3)
N2—H1N2	0.93 (3)	C9—H9	1.00 (3)
N2—H2N2	0.86 (3)	C10—C11	1.395 (3)
C1—C2	1.400 (3)	C10—H10	0.95 (3)
C1—C6	1.413 (3)	C11—C12	1.377 (3)
C2—C3	1.380 (3)	C11—H11	0.91 (3)
C2—H2	0.94 (3)	C12—C13	1.415 (3)
C3—C4	1.392 (3)	C14—H14A	0.9600
C3—H3	0.95 (3)	C14—H14B	0.9600
C4—C5	1.381 (3)	C14—H14C	0.9600
C4—H4	0.94 (3)

C13—O1—H1O1	101.4	C8—C7—H7	117.8 (15)
C12—O2—C14	116.25 (17)	C9—C8—C13	119.34 (18)
C7—N1—C6	121.47 (18)	C9—C8—C7	119.24 (19)
C1—N2—H1N2	112.5 (18)	C13—C8—C7	121.42 (19)
C1—N2—H2N2	100 (2)	C10—C9—C8	120.3 (2)
H1N2—N2—H2N2	119 (3)	C10—C9—H9	119.9 (15)
N2—C1—C2	119.6 (2)	C8—C9—H9	119.5 (15)
N2—C1—C6	121.74 (19)	C9—C10—C11	120.5 (2)
C2—C1—C6	118.64 (19)	C9—C10—H10	118.3 (16)
C3—C2—C1	121.0 (2)	C11—C10—H10	121.2 (16)
C3—C2—H2	127.5 (17)	C12—C11—C10	120.37 (19)
C1—C2—H2	111.4 (17)	C12—C11—H11	121.2 (17)
C2—C3—C4	120.38 (19)	C10—C11—H11	118.4 (17)
C2—C3—H3	118.6 (16)	O2—C12—C11	125.89 (18)
C4—C3—H3	121.0 (17)	O2—C12—C13	114.12 (18)
C5—C4—C3	119.5 (2)	C11—C12—C13	119.99 (19)
C5—C4—H4	120.7 (17)	O1—C13—C8	121.42 (18)
C3—C4—H4	119.9 (17)	O1—C13—C12	119.14 (18)
C4—C5—C6	121.2 (2)	C8—C13—C12	119.44 (18)
C4—C5—H5	117.7 (17)	O2—C14—H14A	109.5
C6—C5—H5	121.1 (16)	O2—C14—H14B	109.5
C5—C6—C1	119.32 (18)	H14A—C14—H14B	109.5
C5—C6—N1	124.99 (19)	O2—C14—H14C	109.5
C1—C6—N1	115.67 (18)	H14A—C14—H14C	109.5
N1—C7—C8	121.86 (19)	H14B—C14—H14C	109.5
N1—C7—H7	120.3 (15)

N2—C1—C2—C3	−178.8 (2)	C13—C8—C9—C10	−0.8 (3)
C6—C1—C2—C3	−1.4 (3)	C7—C8—C9—C10	179.32 (19)
C1—C2—C3—C4	1.7 (3)	C8—C9—C10—C11	0.0 (3)
C2—C3—C4—C5	−0.8 (3)	C9—C10—C11—C12	0.7 (3)
C3—C4—C5—C6	−0.4 (3)	C14—O2—C12—C11	−2.4 (3)
C4—C5—C6—C1	0.6 (3)	C14—O2—C12—C13	178.04 (18)
C4—C5—C6—N1	178.96 (19)	C10—C11—C12—O2	179.84 (19)
N2—C1—C6—C5	177.56 (19)	C10—C11—C12—C13	−0.7 (3)
C2—C1—C6—C5	0.2 (3)	C9—C8—C13—O1	−179.00 (18)
N2—C1—C6—N1	−0.9 (3)	C7—C8—C13—O1	0.9 (3)
C2—C1—C6—N1	−178.23 (19)	C9—C8—C13—C12	0.9 (3)
C7—N1—C6—C5	11.1 (3)	C7—C8—C13—C12	−179.28 (18)
C7—N1—C6—C1	−170.51 (19)	O2—C12—C13—O1	−0.7 (3)
C6—N1—C7—C8	−179.44 (18)	C11—C12—C13—O1	179.74 (18)
N1—C7—C8—C9	179.29 (19)	O2—C12—C13—C8	179.42 (17)
N1—C7—C8—C13	−0.6 (3)	C11—C12—C13—C8	−0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.88	1.77	2.602 (2)	158
N2—H1N2···O1ⁱ	0.93 (3)	2.56 (3)	3.030 (3)	111 (2)
N2—H1N2···O2ⁱ	0.93 (3)	2.29 (3)	3.181 (3)	161 (3)
N2—H2N2···N1	0.87 (3)	2.23 (3)	2.759 (3)	119 (2)
C3—H3···Cg1ⁱⁱ	0.94 (3)	2.64 (3)	3.458 (2)	145 (2)
C11—H11···Cg2ⁱⁱⁱ	0.91 (3)	2.87 (3)	3.538 (2)	142 (2)

Symmetry codes: (i) −x, −y+2, −z; (ii) x, −y+1/2, z−3/2; (iii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₂
M_r	242.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.2790 (6), 14.4810 (6), 6.1928 (3)
β (°)	103.116 (3)
V (Å³)	1159.77 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.959, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	19968, 3402, 2532
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.206, 1.06
No. of reflections	3402
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.31

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.8800	1.7700	2.602 (2)	158.00
N2—H1N2···O1ⁱ	0.93 (3)	2.56 (3)	3.030 (3)	111 (2)
N2—H1N2···O2ⁱ	0.93 (3)	2.29 (3)	3.181 (3)	161 (3)
N2—H2N2···N1	0.87 (3)	2.23 (3)	2.759 (3)	119 (2)
C3—H3···Cg1ⁱⁱ	0.94 (3)	2.64 (3)	3.458 (2)	145 (2)
C11—H11···Cg2ⁱⁱⁱ	0.91 (3)	2.87 (3)	3.538 (2)	142 (2)

Symmetry codes: (i) −x, −y+2, −z; (ii) x, −y+1/2, z−3/2; (iii) x, −y+3/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: shafida@usm.my.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for an IRPA short-term grant (No. 304/PKIMIA/638007) to conduct this work. MHA thanks the Yemen Government and Hadhramout University of Science and Technology (HUST) for financial scholarship support. HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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