2-[(2-Aza­niumyleth­yl)carbamo­yl]phenolate–phenol (1/1)

Yebedri, S.; Louhibi, S.; Bouacida, S.; Ourari, A.; Roisnel, T.

doi:10.1107/S1600536813005849

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o497

doi:10.1107/S1600536813005849

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2-[(2-Azaniumylethyl)carbamoyl]phenolate–phenol (1/1)

Sihem Yebedri,^a Samira Louhibi,^a Sofiane Bouacida,^b ^* Ali Ourari ^c and Thierry Roisnel ^d

^aLaboratoire de Chimie Inorganiue et d'Environment, Université def Tlemcen, BP 119, Tlemcen 13 000, Algeria, ^bUnité de Recherche de Cimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 , Algeria, ^cLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas, Sétif 19000, Algeria, and ^dCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 25 February 2013; accepted 28 February 2013; online 6 March 2013)

In the title 1:1 adduct, C₉H₁₂N₂O₂·C₆H₆O, the dihedral angle between the benzene ring and the salicylic amide group is 6.68 (6)°. The conformation of the amide group is supported by two intramolecular N—H⋯O hydrogen bonds, which close S(6) and S(7) rings. In the crystal, the components are linked by O—H⋯O and N—H⋯O hydrogen bonds, generating (100) sheets.

Related literature

For background to salicylic amides as ligands, see: Koch (2001 ); Hancock & Martell (1989 ).

Experimental

Crystal data

C₉H₁₂N₂O₂·C₆H₆O
M_r = 274.31
Monoclinic, P 2₁ /c
a = 12.6494 (4) Å
b = 13.2145 (6) Å
c = 8.5445 (4) Å
β = 100.637 (2)°
V = 1403.72 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.58 × 0.52 × 0.38 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2011 ) T_min = 0.860, T_max = 0.966
12244 measured reflections
3208 independent reflections
2649 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.03
3208 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.82	1.87	2.6696 (13)	166
N1—H1N⋯O2	0.86	1.93	2.6490 (13)	140
N2—H2A⋯O1	0.89	2.21	2.8995 (14)	134
N2—H2A⋯O3	0.89	2.56	3.0547 (13)	116
N2—H2B⋯O2ⁱⁱ	0.89	1.93	2.7506 (13)	152
N2—H2C⋯O2ⁱⁱⁱ	0.89	1.81	2.6939 (13)	174
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813005849/hb7050sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005849/hb7050Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813005849/hb7050Isup3.cml

checkCIF report

Comment top

Salicylic amide with its diverse amidic forms namely ethylelenediamine or other amines were found to be as good chelating agents currently applied in coordination chemistry (Koch, 2001; Hancock et al., 1989).

The molecule structure of (I), is illustrated in Fig. 1. In the title structure the phenol molecule is cocrystalized with ethylenediamine Salicylic amide The crystal packing can be described by layers parallel to (100) planes (Fig. 2). It features intermolecular O—H···O and N—H···O hydrogen bonds (Fig. 2, Table 1). These interactions link the molecules within the layers and also link the layers together.

Related literature top

For background to salicylic amides as ligands, see: Koch (2001); Hancock & Martell (1989).

Experimental top

0.06 g (1 mmol) ethylenediamine was dissolved in 20 ml of methanol. To this methanolic solution 0.214 g (1 mmol) of phenyl salicylate were added in one portion. This mixture was stirred for one hour at room temperature, and then 0.172 g (1 mmol) of 2-hydroxynaphtaldehyde were also added and heated to 60 °C for 4 h. The solid obtained was recovered by filtration after reducing of its volume on vaccum with rotating evaporator to obtain colourless prisms.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Alternating layers of (I) viewed via b axis showing hydrogen bonds as dashed lines [O—H···O and N—H···O interactions].

2-[(2-Azaniumylethyl)carbamoyl]phenolate–phenol (1/1) top

Crystal data top

C₉H₁₂N₂O₂·C₆H₆O	F(000) = 584
M_r = 274.31	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4306 reflections
a = 12.6494 (4) Å	θ = 2.9–27.4°
b = 13.2145 (6) Å	µ = 0.09 mm⁻¹
c = 8.5445 (4) Å	T = 150 K
β = 100.637 (2)°	Prism, colorless
V = 1403.72 (10) Å³	0.58 × 0.52 × 0.38 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2649 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
CCD rotation images, thin slices scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −16→16
T_min = 0.860, T_max = 0.966	k = −12→17
12244 measured reflections	l = −11→11
3208 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0448P)² + 0.4498P] where P = (F_o² + 2F_c²)/3
3208 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₉H₁₂N₂O₂·C₆H₆O	V = 1403.72 (10) Å³
M_r = 274.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6494 (4) Å	µ = 0.09 mm⁻¹
b = 13.2145 (6) Å	T = 150 K
c = 8.5445 (4) Å	0.58 × 0.52 × 0.38 mm
β = 100.637 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3208 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2011)	2649 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.966	R_int = 0.035
12244 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.27 e Å⁻³
3208 reflections	Δρ_min = −0.21 e Å⁻³
181 parameters

Special details top

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
O2	0.59307 (7)	0.65808 (6)	0.29145 (10)	0.0207 (2)
O3	0.56158 (7)	0.34524 (7)	0.37386 (11)	0.0260 (2)
N1	0.47865 (8)	0.48940 (8)	0.27880 (12)	0.0195 (2)
H1N	0.4845	0.5532	0.2627	0.023*
N2	0.43633 (8)	0.32203 (8)	0.03416 (11)	0.0186 (2)
H2A	0.5036	0.3421	0.0701	0.022*
H2B	0.4287	0.306	−0.0684	0.022*
H2C	0.4219	0.2681	0.0891	0.022*
C7	0.67497 (10)	0.60303 (9)	0.36441 (13)	0.0192 (3)
C8	0.77747 (11)	0.64776 (10)	0.40959 (17)	0.0290 (3)
H8	0.7869	0.7148	0.3819	0.035*
C9	0.86393 (11)	0.59533 (11)	0.49331 (19)	0.0338 (3)
H9	0.9302	0.6274	0.5215	0.041*
C10	0.85282 (11)	0.49477 (11)	0.53593 (17)	0.0302 (3)
H10	0.9106	0.4599	0.595	0.036*
C11	0.75500 (10)	0.44784 (10)	0.48917 (14)	0.0227 (3)
H11	0.7478	0.3803	0.5162	0.027*
C12	0.66564 (10)	0.49853 (9)	0.40198 (13)	0.0183 (3)
C13	0.56553 (10)	0.43867 (9)	0.35241 (13)	0.0186 (3)
C14	0.37497 (10)	0.44126 (9)	0.22499 (14)	0.0201 (3)
H14A	0.3182	0.4889	0.2346	0.024*
H14B	0.3681	0.3839	0.2933	0.024*
C15	0.36081 (10)	0.40533 (9)	0.05392 (14)	0.0202 (3)
H15A	0.2875	0.382	0.0195	0.024*
H15B	0.3726	0.4617	−0.0135	0.024*
O1	0.65559 (7)	0.32899 (7)	−0.02109 (12)	0.0300 (2)
H1	0.6334	0.2758	−0.0644	0.045*
C1	0.76300 (10)	0.33979 (9)	−0.02608 (15)	0.0212 (3)
C2	0.82529 (11)	0.39958 (10)	0.08869 (16)	0.0272 (3)
H2	0.7942	0.4332	0.1645	0.033*
C3	0.93442 (12)	0.40858 (11)	0.08896 (19)	0.0368 (4)
H3	0.9769	0.4482	0.1659	0.044*
C4	0.98085 (12)	0.35932 (12)	−0.0238 (2)	0.0418 (4)
H4	1.0544	0.3648	−0.0217	0.05*
C5	0.91760 (12)	0.30184 (11)	−0.1397 (2)	0.0374 (4)
H5	0.9485	0.2695	−0.2168	0.045*
C6	0.80857 (11)	0.29210 (10)	−0.14187 (16)	0.0265 (3)
H6	0.766	0.2538	−0.2206	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0266 (5)	0.0161 (4)	0.0188 (4)	0.0027 (3)	0.0023 (3)	0.0004 (3)
O3	0.0273 (5)	0.0163 (4)	0.0321 (5)	0.0016 (4)	−0.0003 (4)	0.0016 (4)
N1	0.0217 (5)	0.0143 (5)	0.0213 (5)	0.0006 (4)	0.0008 (4)	−0.0005 (4)
N2	0.0217 (5)	0.0175 (5)	0.0163 (5)	−0.0020 (4)	0.0026 (4)	−0.0013 (4)
C7	0.0242 (6)	0.0188 (6)	0.0148 (5)	0.0032 (5)	0.0042 (4)	−0.0022 (4)
C8	0.0284 (7)	0.0205 (7)	0.0378 (8)	−0.0028 (5)	0.0052 (6)	−0.0014 (5)
C9	0.0219 (7)	0.0310 (8)	0.0462 (9)	−0.0034 (6)	−0.0001 (6)	−0.0067 (6)
C10	0.0250 (7)	0.0284 (7)	0.0332 (7)	0.0060 (6)	−0.0050 (5)	−0.0052 (6)
C11	0.0274 (7)	0.0189 (6)	0.0203 (6)	0.0038 (5)	0.0009 (5)	−0.0030 (5)
C12	0.0222 (6)	0.0177 (6)	0.0150 (5)	0.0014 (5)	0.0030 (4)	−0.0028 (4)
C13	0.0240 (6)	0.0168 (6)	0.0147 (5)	0.0023 (5)	0.0029 (4)	−0.0021 (4)
C14	0.0201 (6)	0.0192 (6)	0.0209 (6)	0.0014 (5)	0.0033 (5)	−0.0013 (5)
C15	0.0211 (6)	0.0177 (6)	0.0203 (6)	0.0018 (5)	0.0004 (4)	0.0015 (5)
O1	0.0244 (5)	0.0233 (5)	0.0436 (6)	−0.0046 (4)	0.0096 (4)	−0.0114 (4)
C1	0.0237 (6)	0.0157 (6)	0.0240 (6)	−0.0004 (5)	0.0033 (5)	0.0034 (5)
C2	0.0358 (8)	0.0214 (6)	0.0235 (6)	−0.0041 (6)	0.0030 (5)	0.0011 (5)
C3	0.0340 (8)	0.0288 (8)	0.0420 (8)	−0.0099 (6)	−0.0076 (6)	0.0050 (6)
C4	0.0240 (7)	0.0311 (8)	0.0709 (11)	−0.0010 (6)	0.0101 (7)	0.0105 (8)
C5	0.0388 (8)	0.0247 (7)	0.0543 (10)	0.0025 (6)	0.0232 (7)	0.0029 (7)
C6	0.0338 (7)	0.0192 (6)	0.0272 (7)	−0.0009 (5)	0.0074 (5)	−0.0004 (5)

Geometric parameters (Å, º) top

O2—C7	1.3239 (15)	C12—C13	1.4868 (17)
O3—C13	1.2505 (15)	C14—C15	1.5158 (16)
N1—C13	1.3408 (16)	C14—H14A	0.97
N1—C14	1.4537 (15)	C14—H14B	0.97
N1—H1N	0.86	C15—H15A	0.97
N2—C15	1.4874 (16)	C15—H15B	0.97
N2—H2A	0.8899	O1—C1	1.3747 (15)
N2—H2B	0.8897	O1—H1	0.8195
N2—H2C	0.8904	C1—C6	1.3852 (18)
C7—C8	1.4123 (18)	C1—C2	1.3862 (18)
C7—C12	1.4276 (17)	C2—C3	1.385 (2)
C8—C9	1.378 (2)	C2—H2	0.93
C8—H8	0.93	C3—C4	1.381 (2)
C9—C10	1.392 (2)	C3—H3	0.93
C9—H9	0.93	C4—C5	1.380 (2)
C10—C11	1.3758 (19)	C4—H4	0.93
C10—H10	0.93	C5—C6	1.382 (2)
C11—C12	1.4037 (17)	C5—H5	0.93
C11—H11	0.93	C6—H6	0.93

C13—N1—C14	122.89 (10)	N1—C14—H14A	109.1
C13—N1—H1N	118.6	C15—C14—H14A	109.1
C14—N1—H1N	118.5	N1—C14—H14B	109.1
C15—N2—H2A	109.5	C15—C14—H14B	109.1
C15—N2—H2B	109.4	H14A—C14—H14B	107.9
H2A—N2—H2B	109.5	N2—C15—C14	112.16 (10)
C15—N2—H2C	109.5	N2—C15—H15A	109.2
H2A—N2—H2C	109.5	C14—C15—H15A	109.2
H2B—N2—H2C	109.4	N2—C15—H15B	109.2
O2—C7—C8	119.86 (11)	C14—C15—H15B	109.2
O2—C7—C12	123.18 (11)	H15A—C15—H15B	107.9
C8—C7—C12	116.95 (11)	C1—O1—H1	109.5
C9—C8—C7	122.14 (13)	O1—C1—C6	121.26 (12)
C9—C8—H8	118.9	O1—C1—C2	118.24 (12)
C7—C8—H8	118.9	C6—C1—C2	120.50 (12)
C8—C9—C10	120.46 (13)	C3—C2—C1	119.09 (13)
C8—C9—H9	119.8	C3—C2—H2	120.5
C10—C9—H9	119.8	C1—C2—H2	120.5
C11—C10—C9	118.90 (13)	C4—C3—C2	120.70 (14)
C11—C10—H10	120.5	C4—C3—H3	119.6
C9—C10—H10	120.5	C2—C3—H3	119.6
C10—C11—C12	122.14 (12)	C5—C4—C3	119.69 (14)
C10—C11—H11	118.9	C5—C4—H4	120.2
C12—C11—H11	118.9	C3—C4—H4	120.2
C11—C12—C7	119.27 (11)	C4—C5—C6	120.38 (14)
C11—C12—C13	117.22 (11)	C4—C5—H5	119.8
C7—C12—C13	123.50 (11)	C6—C5—H5	119.8
O3—C13—N1	120.72 (11)	C5—C6—C1	119.60 (13)
O3—C13—C12	122.58 (11)	C5—C6—H6	120.2
N1—C13—C12	116.68 (11)	C1—C6—H6	120.2
N1—C14—C15	112.41 (10)

O2—C7—C8—C9	176.44 (12)	C7—C12—C13—O3	173.39 (11)
C12—C7—C8—C9	−3.24 (19)	C11—C12—C13—N1	175.56 (10)
C7—C8—C9—C10	0.3 (2)	C7—C12—C13—N1	−4.97 (16)
C8—C9—C10—C11	1.8 (2)	C13—N1—C14—C15	−92.17 (13)
C9—C10—C11—C12	−1.0 (2)	N1—C14—C15—N2	66.25 (13)
C10—C11—C12—C7	−2.00 (18)	O1—C1—C2—C3	177.79 (12)
C10—C11—C12—C13	177.50 (11)	C6—C1—C2—C3	−1.91 (19)
O2—C7—C12—C11	−175.68 (11)	C1—C2—C3—C4	0.4 (2)
C8—C7—C12—C11	3.98 (16)	C2—C3—C4—C5	1.1 (2)
O2—C7—C12—C13	4.86 (17)	C3—C4—C5—C6	−1.0 (2)
C8—C7—C12—C13	−175.47 (11)	C4—C5—C6—C1	−0.5 (2)
C14—N1—C13—O3	2.23 (17)	O1—C1—C6—C5	−177.71 (12)
C14—N1—C13—C12	−179.37 (10)	C2—C1—C6—C5	1.98 (19)
C11—C12—C13—O3	−6.08 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.82	1.87	2.6696 (13)	166
N1—H1N···O2	0.86	1.93	2.6490 (13)	140
N2—H2A···O1	0.89	2.21	2.8995 (14)	134
N2—H2A···O3	0.89	2.56	3.0547 (13)	116
N2—H2B···O2ⁱⁱ	0.89	1.93	2.7506 (13)	152
N2—H2C···O2ⁱⁱⁱ	0.89	1.81	2.6939 (13)	174

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

Experimental details

Crystal data
Chemical formula	C₉H₁₂N₂O₂·C₆H₆O
M_r	274.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	12.6494 (4), 13.2145 (6), 8.5445 (4)
β (°)	100.637 (2)
V (Å³)	1403.72 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.58 × 0.52 × 0.38

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2011)
T_min, T_max	0.860, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	12244, 3208, 2649
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.03
No. of reflections	3208
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.82	1.87	2.6696 (13)	166
N1—H1N···O2	0.86	1.93	2.6490 (13)	140
N2—H2A···O1	0.89	2.21	2.8995 (14)	134
N2—H2A···O3	0.89	2.56	3.0547 (13)	116
N2—H2B···O2ⁱⁱ	0.89	1.93	2.7506 (13)	152
N2—H2C···O2ⁱⁱⁱ	0.89	1.81	2.6939 (13)	174

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

Acknowledgements

Thanks are due to MESRS and ATRST (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et la direction générale de la recherche - Algeria) for financial support.

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