2-{[4-(Phenyldiazenyl)phenyl]iminomethyl}phenol

Fun, H.-K.; Kia, R.; Schiffers, S.; Moghadam, M.; Raithby, P.R.

doi:10.1107/S1600536808027244

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1856-o1857

doi:10.1107/S1600536808027244

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2-{[4-(Phenyldiazenyl)phenyl]iminomethyl}phenol

Hoong-Kun Fun,^a ^* Reza Kia,^a ‡ Stefanie Schiffers,^b Majid Moghadam ^c and Paul R. Raithby ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bChemistry Department, University of Bath, Claverton Down, Bath BA2 7AY, UK, and ^cChemistry Department, University of Isfahan, Isfahan 81746-73441, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 22 August 2008; accepted 23 August 2008; online 30 August 2008)

The molecule of the title compound, C₁₉H₁₅N₃O, is approximately planar and displays a trans configuration with respect to the C=N and N=N double bonds. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. The dihedral angles between the hydroxyphenyl ring and the phenyl and benzene rings are 4.31 (8) and 6.60 (8)°, respectively. The dihedral angle between the phenyl and benzene rings linked by the azo group is 2.70 (8)°. The imino group is coplanar with the hydroxyphenyl ring, as shown by the C—C—C—N torsion angle of −1.8 (2)°. The azo group is disordered over two position with refined site-occupancy factors of ca 0.87/0.13. In the crystal structure, molecules are linked together by intermolecular C—H⋯O interactions along the c axis and also are packed as one-dimensional extended chains down the b axis.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Vani & Vijayan (1977 ); Revannasiddaiah et al. (1997 ). For background to the applications, see, for example: Liu et al. (1990 ); Ikeda & Tsutsumi (1995 ); Evans et al. (1980 ); Griffiths & Allen et al. (1980 ); Flamingi & Monti (1985 ); Leaver et al. (1980 ).

Experimental

Crystal data

C₁₉H₁₅N₃O
M_r = 301.34
Monoclinic, P 2₁ /c
a = 26.0537 (10) Å
b = 4.5475 (2) Å
c = 12.0423 (4) Å
β = 90.600 (2)°
V = 1426.68 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100.0 (1) K
0.52 × 0.20 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.955, T_max = 0.995
35506 measured reflections
4662 independent reflections
3356 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.212
S = 1.08
4662 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	1.01 (3)	1.66 (2)	2.5853 (18)	150 (2)
C5—H5A⋯O1ⁱ	0.93	2.59	3.386 (2)	144
Symmetry code: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536808027244/at2620sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027244/at2620Isup2.hkl

checkCIF report

Comment top

Azobenzene and its derivatives have attracted much attention for their high potential in industrial applications, such as liquid crystals, light-driven switches and image-storage devices (Liu et al., 1990; Ikeda & Tsutsumi, 1995). In addition, azo compounds represent the dominant class of synthetic colourant employed in the textile, printing, agrochemical and pharmaceutical industries. As a result of the presence of the stable chromophoric azo group (N═N) which is capabale of linking different aromatic systems with electron-donating and/or electron-withdrawing groups, dyes can be designed to resist chemical or photochemical degradation processes (Evans et al., 1980; Griffiths & Allen, 1980; Leaver et al., 1980; Flamingi & Monti, 1985).

In the title compound (I) (Fig. 1), the molecule adopts a trans configuration with respect to the C═N and N═N double bonds. The bond lengths and angles are within the normal ranges (Allen et al., 1987). An intramolecular O—H···N hydrogen bond generates a S(6) ring motif (Bernstein et al., 1995). The dihedral angles between the hydroxyphenyl ring and the two phenyl rings are 4.31 (8) and 6.60 (8)°, respectively. The dihedral angle between the two phenyl rings joined by the azo group is 2.70 (8)°. The azo group is disordered over two position and the refined site-occupancy factors of the disordered parts are 0.869 (3)/0.131 (3). The imino group is coplanar with the hydroxyohenyl ring as it can be shown by the C1—C6—C7—N1 torsion angle of -1.8 (2)°. In the crystal structure, molecules are linked together by intermolecular C—H···O interactions (Table 1) along the c axis and also are packed as 1-D extended chains down the b axis (Fig. 2).

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Vani & Vijayan (1977); Revannasiddaiah et al. (1997). For background to the applications, see, for example: Liu et al. (1990); Ikeda & Tsutsumi (1995); Evans et al. (1980); Griffiths & Allen et al. (1980); Flamingi & Monti (1985); Leaver et al. (1980).

Experimental top

The title compound was synthesized by mixing equimolar amount of the p-phenylazo aniline and salicylaldehyde in ethanol under reflux condition for 1 h. Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol 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 (I), showing 50% probability displacement ellipsoids. Intramolecular hydrogen bond is shown as a dashed line. Open bonds indicate the minor disordered component.
	Fig. 2. The crystal packing of the major component of (I), viewed down the b-axis, showing stacking of molecules. Intramolecular and intermolecular interactions are shown as dashed lines.
	Fig. 3. The crystal structure of the major component of (I), showing 1-D extended chains along the b-axis. Intramolecular and intermolecular interactions are shown as dashed lines.

2-{[4-(Phenyldiazenyl)phenyl]iminomethyl}phenol top

Crystal data top

C₁₉H₁₅N₃O	F(000) = 632
M_r = 301.34	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4872 reflections
a = 26.0537 (10) Å	θ = 3.1–31.1°
b = 4.5475 (2) Å	µ = 0.09 mm⁻¹
c = 12.0423 (4) Å	T = 100 K
β = 90.600 (2)°	Plate, yellow
V = 1426.68 (10) Å³	0.52 × 0.20 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4662 independent reflections
Radiation source: fine-focus sealed tube	3356 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 31.4°, θ_min = 0.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −38→38
T_min = 0.955, T_max = 0.995	k = −6→6
35506 measured reflections	l = −17→17

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.1093P)² + 0.6819P] where P = (F_o² + 2F_c²)/3
4662 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₉H₁₅N₃O	V = 1426.68 (10) Å³
M_r = 301.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 26.0537 (10) Å	µ = 0.09 mm⁻¹
b = 4.5475 (2) Å	T = 100 K
c = 12.0423 (4) Å	0.52 × 0.20 × 0.06 mm
β = 90.600 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4662 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3356 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.995	R_int = 0.053
35506 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.88 e Å⁻³
4662 reflections	Δρ_min = −0.53 e Å⁻³
220 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	Occ. (<1)
O1	0.34931 (5)	−0.2401 (3)	0.48842 (10)	0.0256 (3)
N1	0.31269 (5)	0.0728 (3)	0.64837 (11)	0.0163 (3)
N2A	0.16497 (6)	0.9300 (4)	0.75288 (13)	0.0178 (4)	0.869 (3)
N3A	0.16275 (6)	1.0337 (4)	0.85014 (13)	0.0181 (4)	0.869 (3)
N2B	0.1809 (4)	0.924 (3)	0.8304 (9)	0.0178 (4)	0.131 (3)
N3B	0.1469 (5)	1.036 (3)	0.7639 (9)	0.0181 (4)	0.131 (3)
C1	0.38180 (6)	−0.3582 (4)	0.56362 (13)	0.0188 (3)
C2	0.41797 (7)	−0.5647 (4)	0.52832 (14)	0.0226 (4)
H2A	0.4196	−0.6172	0.4538	0.027*
C3	0.45127 (7)	−0.6905 (4)	0.60503 (15)	0.0240 (4)
H3A	0.4757	−0.8247	0.5811	0.029*
C4	0.44882 (6)	−0.6195 (4)	0.71718 (14)	0.0225 (4)
H4A	0.4709	−0.7086	0.7681	0.027*
C5	0.41316 (6)	−0.4151 (4)	0.75211 (14)	0.0202 (3)
H5A	0.4115	−0.3668	0.8270	0.024*
C6	0.37947 (6)	−0.2794 (3)	0.67662 (13)	0.0164 (3)
C7	0.34330 (6)	−0.0621 (4)	0.71608 (13)	0.0169 (3)
H7A	0.3421	−0.0191	0.7915	0.020*
C8	0.27744 (6)	0.2872 (3)	0.68533 (13)	0.0165 (3)
C9	0.24374 (6)	0.3987 (4)	0.60503 (14)	0.0197 (3)
H9A	0.2457	0.3306	0.5324	0.024*
C10	0.20753 (6)	0.6087 (4)	0.63155 (15)	0.0227 (4)
H10A	0.1852	0.6789	0.5770	0.027*
C11	0.20438 (6)	0.7148 (4)	0.73884 (15)	0.0224 (4)
C12	0.23831 (7)	0.6073 (4)	0.82083 (15)	0.0236 (4)
H12A	0.2365	0.6783	0.8931	0.028*
C13	0.27454 (6)	0.3952 (4)	0.79410 (13)	0.0199 (3)
H13A	0.2969	0.3248	0.8485	0.024*
C14	0.12253 (7)	1.2474 (4)	0.86184 (16)	0.0252 (4)
C15	0.08839 (7)	1.3377 (4)	0.77750 (16)	0.0270 (4)
H15A	0.0908	1.2591	0.7065	0.032*
C16	0.05072 (7)	1.5467 (4)	0.80128 (15)	0.0256 (4)
H16A	0.0279	1.6082	0.7460	0.031*
C17	0.04748 (6)	1.6621 (4)	0.90783 (15)	0.0230 (4)
H17A	0.0222	1.7995	0.9242	0.028*
C18	0.08194 (7)	1.5724 (4)	0.98979 (15)	0.0254 (4)
H18A	0.0798	1.6515	1.0608	0.031*
C19	0.11925 (7)	1.3670 (4)	0.96659 (16)	0.0263 (4)
H19A	0.1423	1.3090	1.0219	0.032*
H1O1	0.3277 (10)	−0.093 (6)	0.530 (2)	0.051 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0321 (7)	0.0284 (7)	0.0164 (5)	0.0085 (5)	0.0000 (5)	−0.0010 (5)
N1	0.0171 (6)	0.0130 (6)	0.0188 (6)	−0.0002 (5)	0.0030 (5)	−0.0009 (5)
N2A	0.0183 (8)	0.0145 (8)	0.0206 (7)	0.0000 (6)	0.0030 (6)	−0.0009 (6)
N3A	0.0181 (8)	0.0152 (8)	0.0212 (7)	0.0002 (6)	0.0036 (6)	−0.0018 (6)
N2B	0.0183 (8)	0.0145 (8)	0.0206 (7)	0.0000 (6)	0.0030 (6)	−0.0009 (6)
N3B	0.0181 (8)	0.0152 (8)	0.0212 (7)	0.0002 (6)	0.0036 (6)	−0.0018 (6)
C1	0.0203 (7)	0.0171 (8)	0.0190 (7)	0.0001 (6)	0.0032 (6)	0.0003 (6)
C2	0.0263 (8)	0.0204 (8)	0.0213 (7)	0.0027 (7)	0.0077 (6)	−0.0029 (6)
C3	0.0218 (8)	0.0180 (8)	0.0323 (9)	0.0036 (6)	0.0085 (6)	−0.0017 (7)
C4	0.0192 (8)	0.0198 (8)	0.0284 (8)	0.0008 (6)	−0.0002 (6)	0.0014 (6)
C5	0.0205 (7)	0.0189 (8)	0.0213 (7)	−0.0007 (6)	−0.0004 (6)	−0.0010 (6)
C6	0.0154 (7)	0.0146 (7)	0.0192 (7)	−0.0014 (5)	0.0031 (5)	−0.0004 (6)
C7	0.0178 (7)	0.0158 (7)	0.0172 (7)	−0.0015 (6)	0.0021 (5)	−0.0011 (6)
C8	0.0156 (7)	0.0130 (7)	0.0210 (7)	−0.0012 (5)	0.0044 (5)	−0.0013 (6)
C9	0.0190 (7)	0.0159 (8)	0.0241 (8)	0.0005 (6)	0.0015 (6)	0.0007 (6)
C10	0.0198 (8)	0.0162 (8)	0.0322 (9)	0.0007 (6)	0.0006 (6)	0.0029 (7)
C11	0.0186 (7)	0.0136 (8)	0.0353 (9)	−0.0004 (6)	0.0089 (6)	−0.0003 (7)
C12	0.0274 (8)	0.0186 (8)	0.0249 (8)	−0.0044 (7)	0.0096 (6)	−0.0049 (6)
C13	0.0215 (8)	0.0184 (8)	0.0200 (7)	−0.0014 (6)	0.0058 (6)	−0.0026 (6)
C14	0.0194 (8)	0.0139 (8)	0.0426 (10)	−0.0005 (6)	0.0083 (7)	0.0010 (7)
C15	0.0304 (9)	0.0222 (9)	0.0286 (9)	−0.0042 (7)	0.0081 (7)	−0.0068 (7)
C16	0.0235 (8)	0.0243 (9)	0.0289 (8)	−0.0010 (7)	0.0002 (7)	−0.0009 (7)
C17	0.0195 (8)	0.0185 (8)	0.0310 (9)	0.0039 (6)	0.0065 (6)	−0.0006 (7)
C18	0.0278 (9)	0.0217 (9)	0.0268 (8)	−0.0008 (7)	0.0027 (6)	0.0013 (7)
C19	0.0215 (8)	0.0198 (9)	0.0376 (10)	−0.0002 (6)	0.0002 (7)	0.0062 (7)

Geometric parameters (Å, º) top

O1—C1	1.345 (2)	C8—C9	1.395 (2)
O1—H1O1	1.01 (3)	C8—C13	1.402 (2)
N1—C7	1.290 (2)	C9—C10	1.382 (2)
N1—C8	1.4146 (19)	C9—H9A	0.9300
N2A—N3A	1.264 (2)	C10—C11	1.383 (2)
N2A—C11	1.430 (2)	C10—H10A	0.9300
N3A—C14	1.437 (2)	C11—C12	1.406 (3)
N2B—N3B	1.292 (17)	C12—C13	1.390 (2)
N2B—C11	1.584 (12)	C12—H12A	0.9300
N3B—C14	1.655 (12)	C13—H13A	0.9300
C1—C2	1.400 (2)	C14—C19	1.377 (3)
C1—C6	1.409 (2)	C14—C15	1.404 (3)
C2—C3	1.384 (3)	C15—C16	1.398 (2)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.391 (2)	C16—C17	1.390 (2)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.383 (2)	C17—C18	1.388 (3)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.400 (2)	C18—C19	1.379 (2)
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.449 (2)	C19—H19A	0.9300
C7—H7A	0.9300

C1—O1—H1O1	106.4 (15)	C9—C10—H10A	119.9
C7—N1—C8	121.88 (13)	C10—C11—C12	119.47 (15)
N3A—N2A—C11	113.87 (16)	C10—C11—N2A	113.52 (16)
N2A—N3A—C14	112.55 (17)	C12—C11—N2A	127.01 (16)
N3B—N2B—C11	94.1 (9)	C10—C11—N2B	152.5 (4)
N2B—N3B—C14	93.0 (9)	C12—C11—N2B	88.0 (4)
O1—C1—C2	118.98 (14)	N2A—C11—N2B	39.1 (4)
O1—C1—C6	121.03 (14)	C13—C12—C11	120.14 (15)
C2—C1—C6	119.99 (15)	C13—C12—H12A	119.9
C3—C2—C1	119.58 (15)	C11—C12—H12A	119.9
C3—C2—H2A	120.2	C12—C13—C8	120.20 (16)
C1—C2—H2A	120.2	C12—C13—H13A	119.9
C2—C3—C4	121.16 (15)	C8—C13—H13A	119.9
C2—C3—H3A	119.4	C19—C14—C15	120.13 (16)
C4—C3—H3A	119.4	C19—C14—N3A	114.16 (16)
C5—C4—C3	119.28 (16)	C15—C14—N3A	125.71 (17)
C5—C4—H4A	120.4	C19—C14—N3B	155.6 (5)
C3—C4—H4A	120.4	C15—C14—N3B	84.2 (4)
C4—C5—C6	121.14 (15)	N3A—C14—N3B	41.5 (4)
C4—C5—H5A	119.4	C16—C15—C14	119.43 (17)
C6—C5—H5A	119.4	C16—C15—H15A	120.3
C5—C6—C1	118.81 (14)	C14—C15—H15A	120.3
C5—C6—C7	119.53 (14)	C17—C16—C15	119.70 (17)
C1—C6—C7	121.66 (14)	C17—C16—H16A	120.2
N1—C7—C6	121.13 (14)	C15—C16—H16A	120.2
N1—C7—H7A	119.4	C18—C17—C16	120.02 (16)
C6—C7—H7A	119.4	C18—C17—H17A	120.0
C9—C8—C13	118.75 (14)	C16—C17—H17A	120.0
C9—C8—N1	116.01 (14)	C19—C18—C17	120.46 (17)
C13—C8—N1	125.24 (14)	C19—C18—H18A	119.8
C10—C9—C8	121.15 (15)	C17—C18—H18A	119.8
C10—C9—H9A	119.4	C14—C19—C18	120.25 (17)
C8—C9—H9A	119.4	C14—C19—H19A	119.9
C11—C10—C9	120.29 (16)	C18—C19—H19A	119.9
C11—C10—H10A	119.9

C11—N2A—N3A—C14	−179.52 (13)	N3A—N2A—C11—N2B	−0.3 (6)
C11—N2B—N3B—C14	179.1 (5)	N3B—N2B—C11—C10	3.7 (14)
O1—C1—C2—C3	−179.29 (16)	N3B—N2B—C11—C12	−178.6 (7)
C6—C1—C2—C3	0.0 (3)	N3B—N2B—C11—N2A	−0.4 (5)
C1—C2—C3—C4	1.3 (3)	C10—C11—C12—C13	−0.2 (3)
C2—C3—C4—C5	−1.4 (3)	N2A—C11—C12—C13	179.56 (16)
C3—C4—C5—C6	0.2 (3)	N2B—C11—C12—C13	−179.0 (4)
C4—C5—C6—C1	1.1 (2)	C11—C12—C13—C8	−0.1 (2)
C4—C5—C6—C7	−178.82 (15)	C9—C8—C13—C12	0.6 (2)
O1—C1—C6—C5	178.15 (15)	N1—C8—C13—C12	179.81 (14)
C2—C1—C6—C5	−1.2 (2)	N2A—N3A—C14—C19	−179.48 (15)
O1—C1—C6—C7	−2.0 (2)	N2A—N3A—C14—C15	0.2 (3)
C2—C1—C6—C7	178.71 (15)	N2A—N3A—C14—N3B	−0.7 (6)
C8—N1—C7—C6	−179.47 (13)	N2B—N3B—C14—C19	2.8 (15)
C5—C6—C7—N1	178.11 (15)	N2B—N3B—C14—C15	−179.1 (8)
C1—C6—C7—N1	−1.8 (2)	N2B—N3B—C14—N3A	0.1 (5)
C7—N1—C8—C9	−174.95 (15)	C19—C14—C15—C16	−0.8 (3)
C7—N1—C8—C13	5.8 (2)	N3A—C14—C15—C16	179.45 (16)
C13—C8—C9—C10	−0.9 (2)	N3B—C14—C15—C16	−179.9 (4)
N1—C8—C9—C10	179.83 (14)	C14—C15—C16—C17	−0.1 (3)
C8—C9—C10—C11	0.6 (3)	C15—C16—C17—C18	0.8 (3)
C9—C10—C11—C12	0.0 (3)	C16—C17—C18—C19	−0.6 (3)
C9—C10—C11—N2A	−179.87 (15)	C15—C14—C19—C18	1.0 (3)
C9—C10—C11—N2B	177.3 (9)	N3A—C14—C19—C18	−179.21 (15)
N3A—N2A—C11—C10	−178.25 (15)	N3B—C14—C19—C18	178.8 (10)
N3A—N2A—C11—C12	1.9 (3)	C17—C18—C19—C14	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	1.01 (3)	1.66 (2)	2.5853 (18)	150 (2)
C5—H5A···O1ⁱ	0.93	2.59	3.386 (2)	144

Symmetry code: (i) x, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₃O
M_r	301.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	26.0537 (10), 4.5475 (2), 12.0423 (4)
β (°)	90.600 (2)
V (Å³)	1426.68 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.52 × 0.20 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.955, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	35506, 4662, 3356
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.733

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.212, 1.08
No. of reflections	4662
No. of parameters	220
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.53

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	1.01 (3)	1.66 (2)	2.5853 (18)	150 (2)
C5—H5A···O1ⁱ	0.9300	2.5900	3.386 (2)	144.00

Symmetry code: (i) x, −y−1/2, z+1/2.

Footnotes

‡Additional correspondance author, e-mail: zsrkk@yahoo.com. First post-doctoral position: Chemistry Department, University of Bath, Claverton Down, Bath BA2 7AY, UK.

Acknowledgements

HKF and RK thanks the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia and the University of Bath for the award of post-doctoral research fellowships.

References

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