6-[(2,4-Di­methyl­anilino)methyl­idene]-2-hy­droxy­cyclo­hexa-2,4-dienone

Shujah, S.; Ali, S.; Zia-ur-Rehman; Tahir, M.N.; Meetsma, A.

doi:10.1107/S1600536813012233

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o871

doi:10.1107/S1600536813012233

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6-[(2,4-Dimethylanilino)methylidene]-2-hydroxycyclohexa-2,4-dienone

Shaukat Shujah,^a ^* Saqib Ali,^b Zia-ur-Rehman,^b M. Nawaz Tahir ^c and Auke Meetsma ^d

^aDepartment of Chemistry, Kohat University of Science & Technology, Kohat 26000, Kohat, Pakistan, ^bDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^dCrystal Structure Center, Chemical Physics, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen, The Netherlands
^*Correspondence e-mail: shaukat.shujah@yahoo.com

(Received 2 May 2013; accepted 5 May 2013; online 11 May 2013)

In the title compound, C₁₅H₁₅NO₂, the dihedral angle between the aromatic rings is 5.86 (6)°, and an intramolecular N—H⋯O hydrogen bond generates an S(6) motif, which helps to stabilize the enamine–keto tautomer. An intramolecular O—H⋯O hydrogen bond also occurs. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R₂²(10) loops. A C—H⋯O interaction links the dimers into [010] chains and aromatic π–π stacking [centroid–centroid separation = 3.6131 (9) Å] also occurs.

Related literature

For a related structure and background to Schiff bases, see: Shuja et al. (2007 ). For further structural aspects, see: Blagus & Kaitner (2011 ).

Experimental

Crystal data

C₁₅H₁₅NO₂
M_r = 241.28
Triclinic, $[P \overline 1]$
a = 7.6731 (8) Å
b = 8.4348 (9) Å
c = 10.5806 (12) Å
α = 80.6107 (18)°
β = 75.8216 (19)°
γ = 63.3573 (16)°
V = 592.31 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.53 × 0.48 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.943, T_max = 0.974
4681 measured reflections
2363 independent reflections
2148 reflections with I > 2σ(I)
R_int = 0.009

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.123
S = 1.09
2363 reflections
223 parameters
All H-atom parameters refined
Δρ_max = 0.29 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—H21⋯O2	0.85 (2)	2.340 (17)	2.7674 (12)	111.3 (12)
O1—H21⋯O2ⁱ	0.85 (2)	2.00 (2)	2.7320 (13)	143.4 (15)
N1—H31⋯O2	1.00 (2)	1.72 (2)	2.5873 (12)	142.7 (18)
C13—H13⋯O1ⁱⁱ	0.980 (14)	2.557 (14)	3.3069 (14)	133.3 (13)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y-1, z.

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLUTO (Meetsma, 2006 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813012233/hb7078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012233/hb7078Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012233/hb7078Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of Schiff bases (Shuja et al. 2007), here we report the synthesis and structure of title compound, (I), (Fig. 1). In the molecular structure of (I) the bond distances C7–O2 [1.298 (13) Å] and C1–N1 [1.311 (14) Å] indicate keto-amino tautomeric form. This is further confirmed by a formation of strong intramolecular hydrogen bond N–H···O [N···O = 2.587 (12) Å] resulting in an S(6) ring. The C8–N1–C1–C2 torsion angle is 179.91 (12). The C1–N1 bond length [1.311 (14) Å] is smaller than the N1–C8 bond length [1.417 (14) Å]. The C1–C2 bond length [1.416 (16) Å] indicate a double-bond character and the short C5–C6 bond distance [1.372 (16) Å] of benzene core suggests the presence of quinoid effect (Blagus et al., 2011). The molecules are connected by π–π interactions and O–H···O hydrogen bonds forming a two dimensional network (Fig. 2)

Related literature top

For a related structure and background to Schiff bases, see: Shuja et al. (2007). For further structural aspects, see: Blagus & Kaitner (2011).

Experimental top

An ethanolic solution (50 ml) of 2,4-dimethylaniline (2.5 mmol, 0.30 g) was added dropwise with constant stirring to a hot ethanolic solution (50 ml) of 2,3-dihydroxybenzaldehyde (2.5 mmol, 0.34 g) in a round bottomed flask equipped with a water condenser. The reaction mixture was kept under reflux for 2 h, cooled and kept at room temperature for 48 h. Red blocks of (I) were obtained on slow evaporation of the solvent.

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus (Bruker, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLUTO (Meetsma, 2006) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular stucture of (I), with displacement ellipsoids drawn at the 50% probability level. The intramolecular N—H···O hydrogen bond is shown as dashed lines.
	Fig. 2. Schiff base molecules connected by π–π interactions and O—H···O hydrogen bonds.

6-[(2,4-Dimethylanilino)methylidene]-2-hydroxycyclohexa-2,4-dienone top

Crystal data top

C₁₅H₁₅NO₂	Z = 2
M_r = 241.28	F(000) = 256
Triclinic, P1	The final unit cell was obtained from the xyz centroids of 3645 reflections after integration using the SAINTPLUS software package (Bruker, 2000).
Hall symbol: -P 1	D_x = 1.353 Mg m⁻³
a = 7.6731 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4348 (9) Å	Cell parameters from 3645 reflections
c = 10.5806 (12) Å	θ = 2.7–29.6°
α = 80.6107 (18)°	µ = 0.09 mm⁻¹
β = 75.8216 (19)°	T = 100 K
γ = 63.3573 (16)°	Block, red
V = 592.31 (11) Å³	0.53 × 0.48 × 0.29 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2363 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2148 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	R_int = 0.009
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θ_max = 26.4°, θ_min = 2.7°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −10→10
T_min = 0.943, T_max = 0.974	l = −13→13
4681 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	All H-atom parameters refined
S = 1.09	w = 1/[σ²(F_o²) + (0.0825P)² + 0.0862P] where P = (F_o² + 2F_c²)/3
2363 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₅H₁₅NO₂	γ = 63.3573 (16)°
M_r = 241.28	V = 592.31 (11) Å³
Triclinic, P1	Z = 2
a = 7.6731 (8) Å	Mo Kα radiation
b = 8.4348 (9) Å	µ = 0.09 mm⁻¹
c = 10.5806 (12) Å	T = 100 K
α = 80.6107 (18)°	0.53 × 0.48 × 0.29 mm
β = 75.8216 (19)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2363 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	2148 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.974	R_int = 0.009
4681 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.123	All H-atom parameters refined
S = 1.09	Δρ_max = 0.29 e Å⁻³
2363 reflections	Δρ_min = −0.27 e Å⁻³
223 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.14548 (13)	0.99696 (10)	0.64979 (8)	0.0261 (3)
O2	0.14914 (11)	0.77675 (9)	0.48083 (7)	0.0213 (2)
N1	0.23552 (13)	0.45820 (12)	0.42735 (8)	0.0179 (3)
C1	0.29515 (15)	0.40370 (14)	0.53911 (10)	0.0198 (3)
C2	0.28631 (15)	0.52113 (14)	0.62454 (10)	0.0180 (3)
C3	0.35444 (16)	0.45246 (14)	0.74426 (10)	0.0214 (3)
C4	0.35457 (16)	0.56226 (14)	0.82597 (10)	0.0217 (3)
C5	0.28454 (16)	0.74722 (14)	0.79198 (10)	0.0209 (3)
C6	0.21286 (16)	0.81822 (14)	0.67902 (10)	0.0195 (3)
C7	0.21212 (15)	0.70814 (14)	0.58908 (10)	0.0178 (3)
C8	0.23908 (15)	0.35066 (13)	0.33599 (10)	0.0173 (3)
C9	0.18384 (15)	0.43224 (13)	0.21664 (10)	0.0182 (3)
C10	0.18940 (16)	0.32622 (14)	0.12556 (10)	0.0194 (3)
C11	0.24356 (16)	0.14426 (14)	0.15117 (10)	0.0203 (3)
C12	0.29389 (16)	0.06799 (14)	0.27204 (11)	0.0215 (3)
C13	0.29397 (16)	0.16855 (14)	0.36332 (10)	0.0201 (3)
C14	0.11771 (17)	0.62921 (14)	0.18686 (10)	0.0220 (3)
C15	0.24119 (18)	0.03446 (15)	0.05288 (12)	0.0250 (3)
H1	0.351 (2)	0.273 (2)	0.5651 (14)	0.034 (4)*
H3	0.400 (2)	0.323 (2)	0.7672 (15)	0.042 (4)*
H4	0.401 (2)	0.5179 (18)	0.9075 (14)	0.027 (3)*
H5	0.286 (2)	0.8279 (19)	0.8468 (14)	0.031 (4)*
H10	0.1540 (19)	0.3814 (17)	0.0398 (13)	0.024 (3)*
H12	0.326 (2)	−0.062 (2)	0.2955 (14)	0.036 (4)*
H13	0.328 (2)	0.1118 (18)	0.4479 (13)	0.026 (3)*
H14	0.218 (2)	0.6672 (19)	0.1967 (14)	0.037 (4)*
H14'	0.096 (2)	0.6606 (19)	0.0969 (14)	0.033 (4)*
H14"	−0.010 (2)	0.6970 (19)	0.2456 (14)	0.033 (4)*
H15	0.251 (3)	0.088 (2)	−0.0373 (18)	0.049 (5)*
H15'	0.353 (2)	−0.084 (2)	0.0470 (16)	0.047 (4)*
H15"	0.122 (3)	0.016 (2)	0.0749 (16)	0.046 (4)*
H21	0.076 (3)	1.025 (2)	0.5909 (19)	0.052 (5)*
H31	0.187 (3)	0.590 (3)	0.412 (2)	0.088 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0360 (5)	0.0169 (4)	0.0268 (4)	−0.0088 (3)	−0.0143 (4)	−0.0005 (3)
O2	0.0259 (4)	0.0177 (4)	0.0188 (4)	−0.0070 (3)	−0.0078 (3)	0.0007 (3)
N1	0.0187 (5)	0.0161 (4)	0.0183 (4)	−0.0068 (3)	−0.0035 (3)	−0.0018 (3)
C1	0.0189 (5)	0.0172 (5)	0.0211 (5)	−0.0060 (4)	−0.0037 (4)	−0.0011 (4)
C2	0.0169 (5)	0.0176 (5)	0.0178 (5)	−0.0058 (4)	−0.0031 (4)	−0.0015 (4)
C3	0.0210 (5)	0.0194 (5)	0.0207 (5)	−0.0057 (4)	−0.0053 (4)	−0.0002 (4)
C4	0.0188 (5)	0.0251 (5)	0.0185 (5)	−0.0061 (4)	−0.0057 (4)	−0.0009 (4)
C5	0.0201 (5)	0.0239 (5)	0.0191 (5)	−0.0086 (4)	−0.0034 (4)	−0.0051 (4)
C6	0.0190 (5)	0.0173 (5)	0.0211 (5)	−0.0069 (4)	−0.0028 (4)	−0.0028 (4)
C7	0.0157 (5)	0.0193 (5)	0.0169 (5)	−0.0066 (4)	−0.0026 (4)	−0.0009 (4)
C8	0.0156 (5)	0.0175 (5)	0.0188 (5)	−0.0070 (4)	−0.0025 (4)	−0.0029 (4)
C9	0.0167 (5)	0.0170 (5)	0.0200 (5)	−0.0067 (4)	−0.0030 (4)	−0.0014 (4)
C10	0.0192 (5)	0.0206 (5)	0.0187 (5)	−0.0083 (4)	−0.0043 (4)	−0.0014 (4)
C11	0.0180 (5)	0.0200 (5)	0.0233 (5)	−0.0081 (4)	−0.0021 (4)	−0.0055 (4)
C12	0.0206 (5)	0.0169 (5)	0.0259 (5)	−0.0073 (4)	−0.0045 (4)	−0.0010 (4)
C13	0.0204 (5)	0.0177 (5)	0.0215 (5)	−0.0074 (4)	−0.0053 (4)	0.0001 (4)
C14	0.0283 (6)	0.0172 (5)	0.0204 (5)	−0.0084 (4)	−0.0083 (4)	0.0002 (4)
C15	0.0275 (6)	0.0221 (5)	0.0272 (6)	−0.0102 (5)	−0.0064 (4)	−0.0061 (4)

Geometric parameters (Å, º) top

O1—C6	1.3649 (13)	C10—C11	1.3961 (15)
O2—C7	1.2978 (13)	C11—C12	1.3961 (16)
O1—H21	0.85 (2)	C11—C15	1.5094 (17)
N1—C1	1.3107 (14)	C12—C13	1.3857 (16)
N1—C8	1.4174 (14)	C1—H1	1.005 (15)
N1—H31	1.00 (2)	C3—H3	0.993 (15)
C1—C2	1.4158 (16)	C4—H4	0.968 (15)
C2—C3	1.4237 (15)	C5—H5	0.969 (15)
C2—C7	1.4350 (15)	C10—H10	0.992 (14)
C3—C4	1.3666 (16)	C12—H12	1.012 (15)
C4—C5	1.4184 (15)	C13—H13	0.980 (14)
C5—C6	1.3721 (16)	C14—H14	0.988 (17)
C6—C7	1.4365 (16)	C14—H14'	0.980 (15)
C8—C9	1.4018 (15)	C14—H14"	0.994 (15)
C8—C13	1.3982 (15)	C15—H15	0.987 (18)
C9—C14	1.5061 (15)	C15—H15'	0.982 (16)
C9—C10	1.3989 (15)	C15—H15"	0.96 (2)

O1···O2	2.7674 (12)	C4···H14^iv	2.938 (16)
O1···C13ⁱ	3.3069 (14)	C4···H14'^vi	3.059 (15)
O1···O2ⁱⁱ	2.7320 (13)	C5···H15"ⁱⁱⁱ	2.98 (2)
O1···C14ⁱⁱ	3.3713 (14)	C7···H31	2.35 (2)
O2···O1ⁱⁱ	2.7320 (13)	C12···H3^vii	3.096 (15)
O2···C12ⁱ	3.4092 (14)	C13···H21^v	2.99 (2)
O2···O1	2.7674 (12)	C13···H1	2.635 (15)
O2···N1	2.5873 (12)	C14···H31	2.50 (2)
O2···C13ⁱⁱⁱ	3.2538 (16)	C15···H5^viii	2.871 (15)
O1···H13ⁱ	2.557 (14)	H1···C13	2.635 (15)
O1···H14"ⁱⁱ	2.633 (14)	H1···H3	2.39 (2)
O2···H31	1.72 (2)	H1···H13	2.07 (2)
O2···H12ⁱ	2.649 (16)	H3···H1	2.39 (2)
O2···H21	2.340 (17)	H3···C12^vii	3.096 (15)
O2···H21ⁱⁱ	1.999 (19)	H3···H12^vii	2.31 (2)
N1···O2	2.5873 (12)	H5···C15^ix	2.871 (15)
N1···H14	2.762 (14)	H5···H15^ix	2.57 (2)
N1···H14"	2.900 (15)	H5···H15'^ix	2.59 (2)
C1···C2^iv	3.5296 (18)	H10···C4^x	3.015 (14)
C1···C7^iv	3.4250 (18)	H10···H14'	2.35 (2)
C2···C9ⁱⁱⁱ	3.4592 (18)	H10···H15	2.46 (2)
C2···C1^iv	3.5296 (18)	H10···H10^xi	2.55 (2)
C2···C2^iv	3.5848 (17)	H12···O2^v	2.649 (16)
C4···C9^iv	3.4797 (19)	H12···H3^vii	2.31 (2)
C4···C8^iv	3.4962 (18)	H13···O1^v	2.557 (14)
C5···C13^iv	3.5694 (19)	H13···C1	2.675 (14)
C5···C8^iv	3.3332 (18)	H13···H1	2.07 (2)
C6···C12ⁱⁱⁱ	3.4839 (19)	H13···H21^v	2.46 (3)
C6···C11ⁱⁱⁱ	3.4209 (19)	H14···N1	2.762 (14)
C7···C12ⁱⁱⁱ	3.5121 (18)	H14···H31	2.25 (3)
C7···C13ⁱⁱⁱ	3.4649 (19)	H14···C4^iv	2.938 (16)
C7···C1^iv	3.4250 (18)	H14'···C4^x	3.059 (15)
C7···C8ⁱⁱⁱ	3.5955 (18)	H14'···H10	2.35 (2)
C8···C5^iv	3.3332 (18)	H14"···N1	2.900 (15)
C8···C4^iv	3.4962 (18)	H14"···H31	2.40 (3)
C8···C7ⁱⁱⁱ	3.5955 (18)	H14"···O1ⁱⁱ	2.633 (14)
C9···C2ⁱⁱⁱ	3.4592 (18)	H14"···C1ⁱⁱⁱ	3.048 (16)
C9···C4^iv	3.4797 (19)	H15···H5^viii	2.57 (2)
C11···C6ⁱⁱⁱ	3.4209 (19)	H15···H10	2.46 (2)
C12···C7ⁱⁱⁱ	3.5121 (18)	H15'···H5^viii	2.59 (2)
C12···O2^v	3.4092 (14)	H15"···C5ⁱⁱⁱ	2.98 (2)
C12···C6ⁱⁱⁱ	3.4839 (19)	H21···O2	2.340 (17)
C13···C5^iv	3.5694 (19)	H21···C13ⁱ	2.99 (2)
C13···C7ⁱⁱⁱ	3.4649 (19)	H21···H13ⁱ	2.46 (3)
C13···O2ⁱⁱⁱ	3.2538 (16)	H21···O2ⁱⁱ	2.00 (2)
C13···O1^v	3.3069 (14)	H31···O2	1.72 (2)
C14···O1ⁱⁱ	3.3713 (14)	H31···C7	2.35 (2)
C1···H14"ⁱⁱⁱ	3.048 (16)	H31···C14	2.50 (2)
C1···H13	2.675 (14)	H31···H14	2.25 (3)
C4···H10^vi	3.015 (14)	H31···H14"	2.40 (3)

C6—O1—H21	108.2 (11)	C8—C13—C12	119.90 (10)
C1—N1—C8	126.62 (9)	N1—C1—H1	118.8 (9)
C1—N1—H31	110.9 (13)	C2—C1—H1	118.4 (9)
C8—N1—H31	122.5 (12)	C2—C3—H3	118.1 (9)
N1—C1—C2	122.78 (10)	C4—C3—H3	121.0 (9)
C1—C2—C3	119.73 (10)	C3—C4—H4	122.0 (8)
C1—C2—C7	119.92 (10)	C5—C4—H4	118.2 (8)
C3—C2—C7	120.35 (10)	C4—C5—H5	121.7 (9)
C2—C3—C4	120.82 (10)	C6—C5—H5	117.5 (9)
C3—C4—C5	119.78 (10)	C9—C10—H10	119.3 (8)
C4—C5—C6	120.82 (10)	C11—C10—H10	118.6 (8)
O1—C6—C5	119.25 (10)	C11—C12—H12	119.8 (9)
O1—C6—C7	119.23 (10)	C13—C12—H12	118.9 (9)
C5—C6—C7	121.50 (10)	C8—C13—H13	120.6 (8)
C2—C7—C6	116.70 (10)	C12—C13—H13	119.5 (8)
O2—C7—C2	122.55 (10)	C9—C14—H14	111.6 (8)
O2—C7—C6	120.74 (9)	C9—C14—H14'	109.8 (9)
N1—C8—C13	121.55 (9)	C9—C14—H14"	110.7 (8)
N1—C8—C9	118.11 (9)	H14—C14—H14'	108.3 (13)
C9—C8—C13	120.34 (10)	H14—C14—H14"	108.7 (13)
C8—C9—C10	118.30 (9)	H14'—C14—H14"	107.6 (13)
C8—C9—C14	121.27 (9)	C11—C15—H15	113.3 (11)
C10—C9—C14	120.43 (9)	C11—C15—H15'	113.3 (10)
C9—C10—C11	122.16 (10)	C11—C15—H15"	111.1 (10)
C10—C11—C15	120.97 (10)	H15—C15—H15'	104.2 (14)
C10—C11—C12	118.03 (10)	H15—C15—H15"	107.9 (18)
C12—C11—C15	120.97 (10)	H15'—C15—H15"	106.4 (14)
C11—C12—C13	121.25 (10)

C8—N1—C1—C2	179.91 (12)	O1—C6—C7—C2	179.47 (11)
C1—N1—C8—C9	−174.84 (12)	C5—C6—C7—O2	−177.99 (12)
C1—N1—C8—C13	5.77 (19)	C5—C6—C7—C2	1.19 (18)
N1—C1—C2—C3	−179.77 (12)	N1—C8—C9—C10	179.26 (11)
N1—C1—C2—C7	−0.87 (19)	N1—C8—C9—C14	−1.44 (18)
C1—C2—C3—C4	177.46 (12)	C13—C8—C9—C10	−1.34 (18)
C7—C2—C3—C4	−1.44 (19)	C13—C8—C9—C14	177.96 (12)
C1—C2—C7—O2	0.84 (19)	N1—C8—C13—C12	179.40 (12)
C1—C2—C7—C6	−178.32 (11)	C9—C8—C13—C12	0.0 (2)
C3—C2—C7—O2	179.74 (12)	C8—C9—C10—C11	1.45 (19)
C3—C2—C7—C6	0.58 (18)	C14—C9—C10—C11	−177.87 (12)
C2—C3—C4—C5	0.53 (19)	C9—C10—C11—C12	−0.20 (19)
C3—C4—C5—C6	1.26 (19)	C9—C10—C11—C15	177.81 (12)
C4—C5—C6—O1	179.58 (12)	C10—C11—C12—C13	−1.2 (2)
C4—C5—C6—C7	−2.1 (2)	C15—C11—C12—C13	−179.20 (12)
O1—C6—C7—O2	0.29 (18)	C11—C12—C13—C8	1.3 (2)

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) x, y−1, z; (vi) x, y, z+1; (vii) −x+1, −y, −z+1; (viii) x, y−1, z−1; (ix) x, y+1, z+1; (x) x, y, z−1; (xi) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H21···O2	0.85 (2)	2.340 (17)	2.7674 (12)	111.3 (12)
O1—H21···O2ⁱⁱ	0.85 (2)	2.00 (2)	2.7320 (13)	143.4 (15)
N1—H31···O2	1.00 (2)	1.72 (2)	2.5873 (12)	142.7 (18)
C13—H13···O1^v	0.980 (14)	2.557 (14)	3.3069 (14)	133.3 (13)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₂
M_r	241.28
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.6731 (8), 8.4348 (9), 10.5806 (12)
α, β, γ (°)	80.6107 (18), 75.8216 (19), 63.3573 (16)
V (Å³)	592.31 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.53 × 0.48 × 0.29

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.943, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	4681, 2363, 2148
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.123, 1.09
No. of reflections	2363
No. of parameters	223
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

Computer programs: SMART (Bruker, 2006), SAINT-Plus (Bruker, 2006), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), PLUTO (Meetsma, 2006) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H21···O2	0.85 (2)	2.340 (17)	2.7674 (12)	111.3 (12)
O1—H21···O2ⁱ	0.85 (2)	2.00 (2)	2.7320 (13)	143.4 (15)
N1—H31···O2	1.00 (2)	1.72 (2)	2.5873 (12)	142.7 (18)
C13—H13···O1ⁱⁱ	0.980 (14)	2.557 (14)	3.3069 (14)	133.3 (13)

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

Acknowledgements

SS thanks the HEC (Higher Education Commission), Islamabad, for a fellowship (PIN No. 042–111889-PS2–104).

References

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