3-[(E)-(Pyridin-3-yl­imino)­meth­yl]phenol

Tahir, M.N.; Ali, A.; Umar, M.N.; Hussain, I.; Shad, H.A.

doi:10.1107/S1600536812025822

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2072

https://doi.org/10.1107/S1600536812025822

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3-[(E)-(Pyridin-3-ylimino)methyl]phenol

M. Nawaz Tahir,^a ^* Akbar Ali,^b M. Naveed Umar,^b Ishtiaq Hussain ^c and Hazoor Ahmad Shad ^d

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, University of Malakand, Pakistan, ^cDepartment of Chemistry, University of Sargodha, Pakistan, and ^dDepartment of Chemistry, Government Post Graduate College, Gojra, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 1 June 2012; accepted 6 June 2012; online 13 June 2012)

Two independent molecules are present in the asymmetric unit of the title compound, C₁₂H₁₀N₂O, in which the 3-hydroxybenzaldehyde and the pyridin-3-amine units are almost planar [r.m.s. deviations of 0.0236 and 0.0116Å, respectively, in one molecule and 0.0245 and 0.0162Å, respectively, in the other] and are oriented at dihedral angles of 7.21 (7) and 14.77 (7)°. In the crystal, molecules of the same type form inversion dimers via pairs of O—H⋯N hydrogen bonds, forming R₂²(20) ring motifs. There exist π–π interactions between the benzene and pyridine rings of molecules of the same type with centroid–centroid distances of 3.7127 (10) and 3.8439 (10) Å.

Related literature

For a related structure, see: Wiebcke & Mootz (1982 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₁₀N₂O
M_r = 198.22
Triclinic, $[P \overline 1]$
a = 5.7768 (5) Å
b = 12.1450 (11) Å
c = 14.8194 (13) Å
α = 78.207 (4)°
β = 89.641 (3)°
γ = 77.601 (4)°
V = 993.26 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.957, T_max = 0.966
14798 measured reflections
3876 independent reflections
2704 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.118
S = 1.04
3876 reflections
261 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.82	2.00	2.810 (2)	172
O2—H2A⋯N4ⁱⁱ	0.82	1.99	2.8058 (12)	174
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025822/rk2365sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025822/rk2365Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025822/rk2365Isup3.cml

checkCIF report

Comment top

In the crystal structure, (Fig. 1), of title compound, two molecules in the asymmetric unit are present, which differ slightly from each other geometrically. In one molecule, the 3-hydroxybenzaldehyde group A (C1–C7/O1) and the pyridin-3-amine moiety B (C8–C12/N1/N2) are planar with r.m.s. deviation of 0.0236Å and 0.0116Å, respectively. The dihedral angle between A/B is 14.78 (7)°. In second molecule, the similar groups C (C13–C19/O2) and D (C20–C24/N3/N4) are also planar with r.m.s. deviation of 0.0245Å and 0.0162Å, respectively and the dihedral angle between C/D is 7.21 (7)°. Both molecules are dimerized with themselves due to intermolecular H-bonding of O—H···N type (Table 1, Fig. 2) and form R₂²(20) ring motif (Bernstein et al., 1995). There exist π···π interaction between Cg1···Cg2ⁱⁱⁱ and Cg2···Cg1ⁱⁱⁱ at a distance of 3.8439 (11)Å. Similarly, there exist π···π interaction between Cg3···Cg4^iv and Cg4···Cg3^iv at a distance of 3.7126 (10)Å. Cg1, Cg2, Cg3 and Cg4 are the centroids of (C8–C12/N2), (C1–C6), (C20–C24/N4) and (C13–C18) rings, respectively. Symmetry codes: (iii) = -x, -y, -z; (iv) = -x, -y, -z+1.

The structure of related compounds - trans-N-benzylidene-3-pyridinamine has been published by Wiebcke & Mootz, 1982.

Related literature top

For a related structure, see: Wiebcke & Mootz (1982). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

The title compound has been synthesized as a derivative. Equimolar quantities of 3-hydroxybenzaldehyde and pyridin-3-amine were refluxed in methanol along with few drops of acetic acid as catalyst for 30 min resulting in colourless solution. The solution was kept at room temperature which affoarded colourless prisms after three days.

Structure description top

The structure of related compounds - trans-N-benzylidene-3-pyridinamine has been published by Wiebcke & Mootz, 1982.

For a related structure, see: Wiebcke & Mootz (1982). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are shown as small circles of arbitrary radii.
	Fig. 2. The partial packing which shows that molecules form dimers. Symmetry codes: (i) = -x+1, -y, -z; (ii) = -x+1, -y, -z+1.

3-[(E)-(Pyridin-3-ylimino)methyl]phenol top

Crystal data top

C₁₂H₁₀N₂O	Z = 4
M_r = 198.22	F(000) = 416
Triclinic, P1	D_x = 1.326 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7768 (5) Å	Cell parameters from 2704 reflections
b = 12.1450 (11) Å	θ = 1.8–26.0°
c = 14.8194 (13) Å	µ = 0.09 mm⁻¹
α = 78.207 (4)°	T = 296 K
β = 89.641 (3)°	Prism, colourless
γ = 77.601 (4)°	0.30 × 0.25 × 0.20 mm
V = 993.26 (15) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3876 independent reflections
Radiation source: fine-focus sealed tube	2704 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 1.8°
ω–scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
T_min = 0.957, T_max = 0.966	l = −18→18
14798 measured 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0494P)² + 0.1521P] where P = (F_o² + 2F_c²)/3
3876 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₂H₁₀N₂O	γ = 77.601 (4)°
M_r = 198.22	V = 993.26 (15) Å³
Triclinic, P1	Z = 4
a = 5.7768 (5) Å	Mo Kα radiation
b = 12.1450 (11) Å	µ = 0.09 mm⁻¹
c = 14.8194 (13) Å	T = 296 K
α = 78.207 (4)°	0.30 × 0.25 × 0.20 mm
β = 89.641 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3876 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2704 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.966	R_int = 0.029
14798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	Δρ_max = 0.12 e Å⁻³
3876 reflections	Δρ_min = −0.16 e Å⁻³
261 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.3002 (3)	−0.38329 (11)	0.13058 (10)	0.0720 (6)
N1	0.1603 (3)	0.05071 (12)	0.10067 (9)	0.0500 (5)
N2	0.4028 (3)	0.29991 (13)	0.00539 (10)	0.0566 (6)
C1	0.1241 (3)	−0.29847 (16)	0.15019 (12)	0.0525 (6)
C2	0.1340 (3)	−0.18383 (14)	0.12760 (11)	0.0470 (6)
C3	−0.0509 (3)	−0.09881 (15)	0.14672 (11)	0.0453 (6)
C4	−0.2498 (3)	−0.13042 (17)	0.18808 (12)	0.0562 (7)
C5	−0.2555 (3)	−0.24564 (19)	0.21309 (13)	0.0622 (8)
C6	−0.0716 (3)	−0.32902 (17)	0.19536 (12)	0.0603 (7)
C7	−0.0320 (3)	0.02167 (15)	0.12514 (11)	0.0478 (6)
C8	0.1768 (3)	0.16709 (14)	0.08358 (11)	0.0450 (5)
C9	0.0388 (3)	0.25436 (16)	0.12042 (12)	0.0574 (7)
C10	0.0867 (4)	0.36199 (16)	0.09900 (13)	0.0642 (7)
C11	0.2672 (3)	0.38158 (16)	0.04216 (13)	0.0609 (7)
C12	0.3563 (3)	0.19524 (15)	0.02750 (12)	0.0506 (6)
O2	−0.01543 (13)	0.39654 (6)	0.38845 (7)	0.0683 (5)
N3	0.19245 (12)	−0.03508 (6)	0.39821 (6)	0.0500 (5)
N4	0.64794 (12)	−0.29360 (6)	0.47831 (6)	0.0537 (5)
C13	−0.12229 (13)	0.31831 (6)	0.36181 (7)	0.0512 (6)
C14	−0.02002 (12)	0.20228 (6)	0.37886 (6)	0.0467 (6)
C15	−0.1372 (3)	0.12369 (15)	0.35433 (11)	0.0451 (6)
C16	−0.3621 (3)	0.16340 (18)	0.31206 (12)	0.0573 (7)
C17	−0.4595 (3)	0.28010 (19)	0.29175 (13)	0.0638 (7)
C18	−0.3421 (3)	0.35724 (17)	0.31563 (12)	0.0598 (7)
C19	−0.0232 (3)	0.00155 (15)	0.37155 (11)	0.0480 (6)
C20	0.3013 (3)	−0.15308 (14)	0.41181 (11)	0.0436 (5)
C21	0.2182 (3)	−0.23740 (15)	0.37925 (12)	0.0516 (6)
C22	0.3527 (3)	−0.34747 (15)	0.39586 (12)	0.0553 (7)
C23	0.5661 (3)	−0.37225 (15)	0.44406 (12)	0.0547 (6)
C24	0.5160 (3)	−0.18691 (15)	0.46091 (12)	0.0491 (6)
H1	0.38859	−0.35466	0.09392	0.1080*
H2	0.26668	−0.16302	0.09910	0.0564*
H4	−0.37822	−0.07438	0.19884	0.0674*
H5	−0.38665	−0.26689	0.24252	0.0747*
H6	−0.07728	−0.40633	0.21353	0.0723*
H7	−0.16522	0.07872	0.12950	0.0574*
H9	−0.08377	0.23995	0.15891	0.0689*
H10	−0.00331	0.42169	0.12306	0.0771*
H11	0.29688	0.45537	0.02849	0.0732*
H12	0.45151	0.13687	0.00348	0.0606*
H2A	0.09555	0.36277	0.42494	0.1024*
H14	0.13035	0.17617	0.40734	0.0560*
H16	−0.44634	0.11167	0.29759	0.0688*
H17	−0.60742	0.30686	0.26131	0.0765*
H18	−0.40970	0.43573	0.30089	0.0717*
H19	−0.11186	−0.05113	0.36265	0.0576*
H21	0.07331	−0.21935	0.34665	0.0620*
H22	0.29991	−0.40511	0.37463	0.0663*
H23	0.65766	−0.44690	0.45330	0.0656*
H24	0.57225	−0.13110	0.48342	0.0589*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0813 (10)	0.0476 (8)	0.0915 (11)	−0.0207 (7)	0.0199 (8)	−0.0179 (7)
N1	0.0536 (9)	0.0454 (9)	0.0502 (9)	−0.0099 (7)	0.0086 (7)	−0.0094 (7)
N2	0.0648 (9)	0.0486 (10)	0.0605 (10)	−0.0178 (8)	0.0029 (7)	−0.0147 (8)
C1	0.0600 (11)	0.0510 (11)	0.0503 (11)	−0.0189 (9)	0.0007 (8)	−0.0123 (9)
C2	0.0508 (10)	0.0507 (11)	0.0430 (10)	−0.0191 (8)	0.0057 (7)	−0.0093 (8)
C3	0.0466 (9)	0.0554 (11)	0.0358 (9)	−0.0146 (8)	−0.0006 (7)	−0.0099 (8)
C4	0.0474 (10)	0.0757 (14)	0.0498 (11)	−0.0184 (9)	0.0040 (8)	−0.0180 (10)
C5	0.0592 (12)	0.0834 (16)	0.0531 (12)	−0.0352 (11)	0.0082 (9)	−0.0145 (10)
C6	0.0728 (13)	0.0638 (13)	0.0529 (12)	−0.0372 (11)	0.0017 (9)	−0.0083 (9)
C7	0.0481 (10)	0.0534 (11)	0.0406 (10)	−0.0049 (8)	0.0003 (8)	−0.0132 (8)
C8	0.0507 (9)	0.0424 (10)	0.0400 (9)	−0.0059 (8)	−0.0024 (7)	−0.0087 (8)
C9	0.0662 (12)	0.0530 (12)	0.0500 (11)	−0.0053 (9)	0.0103 (9)	−0.0120 (9)
C10	0.0836 (14)	0.0471 (12)	0.0605 (12)	−0.0029 (10)	0.0044 (10)	−0.0198 (10)
C11	0.0778 (13)	0.0447 (11)	0.0613 (12)	−0.0143 (10)	−0.0061 (10)	−0.0120 (9)
C12	0.0550 (10)	0.0472 (11)	0.0514 (11)	−0.0103 (8)	0.0046 (8)	−0.0156 (8)
O2	0.0658 (8)	0.0451 (8)	0.0890 (10)	−0.0024 (6)	−0.0092 (7)	−0.0127 (7)
N3	0.0533 (9)	0.0449 (9)	0.0511 (9)	−0.0079 (7)	−0.0042 (7)	−0.0112 (7)
N4	0.0559 (9)	0.0460 (9)	0.0565 (9)	−0.0070 (7)	0.0029 (7)	−0.0089 (7)
C13	0.0488 (10)	0.0517 (11)	0.0492 (10)	−0.0036 (8)	0.0047 (8)	−0.0096 (8)
C14	0.0430 (9)	0.0482 (11)	0.0441 (10)	−0.0014 (8)	−0.0026 (7)	−0.0075 (8)
C15	0.0454 (9)	0.0539 (11)	0.0352 (9)	−0.0067 (8)	0.0054 (7)	−0.0121 (8)
C16	0.0438 (10)	0.0779 (14)	0.0521 (11)	−0.0082 (9)	0.0017 (8)	−0.0230 (10)
C17	0.0444 (10)	0.0849 (16)	0.0539 (12)	0.0083 (10)	−0.0056 (8)	−0.0191 (11)
C18	0.0546 (11)	0.0592 (12)	0.0540 (11)	0.0103 (9)	0.0030 (9)	−0.0092 (10)
C19	0.0526 (10)	0.0538 (11)	0.0422 (10)	−0.0158 (8)	0.0053 (8)	−0.0159 (8)
C20	0.0506 (9)	0.0428 (10)	0.0385 (9)	−0.0111 (8)	0.0044 (7)	−0.0100 (8)
C21	0.0586 (10)	0.0509 (11)	0.0470 (10)	−0.0135 (9)	−0.0027 (8)	−0.0122 (8)
C22	0.0721 (12)	0.0460 (11)	0.0512 (11)	−0.0168 (9)	0.0018 (9)	−0.0140 (9)
C23	0.0675 (12)	0.0404 (10)	0.0540 (11)	−0.0093 (9)	0.0101 (9)	−0.0075 (8)
C24	0.0526 (10)	0.0442 (10)	0.0521 (11)	−0.0122 (8)	0.0020 (8)	−0.0122 (8)

Geometric parameters (Å, º) top

O1—C1	1.360 (2)	C6—H6	0.9300
O1—H1	0.8200	C7—H7	0.9300
O2—C13	1.3594 (11)	C9—H9	0.9300
O2—H2A	0.8200	C10—H10	0.9300
N1—C7	1.265 (2)	C11—H11	0.9300
N1—C8	1.408 (2)	C12—H12	0.9300
N2—C11	1.333 (2)	C13—C14	1.3775 (11)
N2—C12	1.331 (2)	C13—C18	1.388 (2)
N3—C20	1.4094 (19)	C14—C15	1.3870 (19)
N3—C19	1.2658 (19)	C15—C16	1.389 (3)
N4—C23	1.3374 (19)	C15—C19	1.459 (3)
N4—C24	1.330 (2)	C16—C17	1.379 (3)
C1—C6	1.390 (3)	C17—C18	1.369 (3)
C1—C2	1.377 (3)	C20—C21	1.389 (2)
C2—C3	1.389 (2)	C20—C24	1.381 (2)
C3—C4	1.388 (3)	C21—C22	1.369 (3)
C3—C7	1.460 (3)	C22—C23	1.373 (3)
C4—C5	1.380 (3)	C14—H14	0.9300
C5—C6	1.366 (3)	C16—H16	0.9300
C8—C12	1.381 (2)	C17—H17	0.9300
C8—C9	1.388 (3)	C18—H18	0.9300
C9—C10	1.368 (3)	C19—H19	0.9300
C10—C11	1.366 (3)	C21—H21	0.9300
C2—H2	0.9300	C22—H22	0.9300
C4—H4	0.9300	C23—H23	0.9300
C5—H5	0.9300	C24—H24	0.9300

C1—O1—H1	109.00	C10—C11—H11	118.00
C13—O2—H2A	109.00	C8—C12—H12	118.00
C7—N1—C8	120.93 (16)	N2—C12—H12	118.00
C11—N2—C12	116.56 (16)	O2—C13—C18	118.56 (11)
C19—N3—C20	121.28 (12)	C14—C13—C18	119.06 (11)
C23—N4—C24	116.83 (12)	O2—C13—C14	122.38 (8)
C2—C1—C6	119.03 (17)	C13—C14—C15	121.21 (10)
O1—C1—C6	118.63 (17)	C14—C15—C19	120.14 (14)
O1—C1—C2	122.33 (16)	C16—C15—C19	120.83 (17)
C1—C2—C3	121.07 (16)	C14—C15—C16	119.02 (16)
C2—C3—C7	119.93 (16)	C15—C16—C17	119.49 (18)
C2—C3—C4	119.13 (17)	C16—C17—C18	121.11 (17)
C4—C3—C7	120.93 (17)	C13—C18—C17	119.99 (17)
C3—C4—C5	119.48 (18)	N3—C19—C15	122.14 (15)
C4—C5—C6	121.09 (17)	N3—C20—C24	115.98 (14)
C1—C6—C5	120.09 (19)	C21—C20—C24	117.11 (16)
N1—C7—C3	121.91 (16)	N3—C20—C21	126.89 (15)
C9—C8—C12	117.15 (16)	C20—C21—C22	119.00 (16)
N1—C8—C12	116.06 (15)	C21—C22—C23	119.57 (17)
N1—C8—C9	126.72 (16)	N4—C23—C22	122.80 (16)
C8—C9—C10	118.67 (17)	N4—C24—C20	124.66 (16)
C9—C10—C11	119.83 (18)	C13—C14—H14	119.00
N2—C11—C10	123.09 (18)	C15—C14—H14	119.00
N2—C12—C8	124.68 (17)	C15—C16—H16	120.00
C3—C2—H2	119.00	C17—C16—H16	120.00
C1—C2—H2	119.00	C16—C17—H17	119.00
C3—C4—H4	120.00	C18—C17—H17	119.00
C5—C4—H4	120.00	C13—C18—H18	120.00
C4—C5—H5	119.00	C17—C18—H18	120.00
C6—C5—H5	119.00	N3—C19—H19	119.00
C1—C6—H6	120.00	C15—C19—H19	119.00
C5—C6—H6	120.00	C20—C21—H21	120.00
N1—C7—H7	119.00	C22—C21—H21	121.00
C3—C7—H7	119.00	C21—C22—H22	120.00
C8—C9—H9	121.00	C23—C22—H22	120.00
C10—C9—H9	121.00	N4—C23—H23	119.00
C11—C10—H10	120.00	C22—C23—H23	119.00
C9—C10—H10	120.00	N4—C24—H24	118.00
N2—C11—H11	118.00	C20—C24—H24	118.00

C8—N1—C7—C3	−177.57 (15)	C12—C8—C9—C10	0.4 (3)
C7—N1—C8—C9	25.4 (3)	C9—C8—C12—N2	−1.2 (3)
C7—N1—C8—C12	−157.68 (16)	N1—C8—C12—N2	−178.40 (16)
C12—N2—C11—C10	−0.7 (3)	C8—C9—C10—C11	0.2 (3)
C11—N2—C12—C8	1.3 (3)	C9—C10—C11—N2	0.0 (3)
C20—N3—C19—C15	−178.07 (14)	O2—C13—C14—C15	177.30 (11)
C19—N3—C20—C21	16.4 (2)	C18—C13—C14—C15	−2.84 (17)
C19—N3—C20—C24	−165.28 (15)	O2—C13—C18—C17	−176.90 (14)
C23—N4—C24—C20	1.1 (2)	C14—C13—C18—C17	3.2 (2)
C24—N4—C23—C22	−2.3 (2)	C13—C14—C15—C16	−0.2 (2)
C6—C1—C2—C3	−2.0 (3)	C13—C14—C15—C19	178.83 (12)
O1—C1—C6—C5	−177.63 (17)	C14—C15—C16—C17	2.8 (2)
O1—C1—C2—C3	178.60 (16)	C19—C15—C16—C17	−176.18 (16)
C2—C1—C6—C5	2.9 (3)	C14—C15—C19—N3	−8.8 (2)
C1—C2—C3—C4	−0.9 (3)	C16—C15—C19—N3	170.20 (15)
C1—C2—C3—C7	177.73 (16)	C15—C16—C17—C18	−2.5 (3)
C2—C3—C7—N1	−9.6 (2)	C16—C17—C18—C13	−0.6 (3)
C4—C3—C7—N1	169.05 (16)	N3—C20—C21—C22	177.27 (15)
C2—C3—C4—C5	2.9 (3)	C24—C20—C21—C22	−1.0 (2)
C7—C3—C4—C5	−175.76 (16)	N3—C20—C24—N4	−177.97 (14)
C3—C4—C5—C6	−2.0 (3)	C21—C20—C24—N4	0.5 (3)
C4—C5—C6—C1	−1.0 (3)	C20—C21—C22—C23	−0.1 (3)
N1—C8—C9—C10	177.26 (17)	C21—C22—C23—N4	1.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.82	2.00	2.810 (2)	172
O2—H2A···N4ⁱⁱ	0.82	1.99	2.8058 (12)	174

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂O
M_r	198.22
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.7768 (5), 12.1450 (11), 14.8194 (13)
α, β, γ (°)	78.207 (4), 89.641 (3), 77.601 (4)
V (Å³)	993.26 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.957, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	14798, 3876, 2704
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.118, 1.04
No. of reflections	3876
No. of parameters	261
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.82	2.00	2.810 (2)	172
O2—H2A···N4ⁱⁱ	0.82	1.99	2.8058 (12)	174

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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