2-[(E)-N-(Adamantan-1-yl)carbox­imidoyl]-6-eth­oxy­phenol

Shaheen, M.A.; Tahir, M.N.; Irfan, R.M.; Iqbal, S.; Zaneb, M.

doi:10.1107/S1600536812033594

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2588

https://doi.org/10.1107/S1600536812033594

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2-[(E)-N-(Adamantan-1-yl)carboximidoyl]-6-ethoxyphenol

Muhammad Ashraf Shaheen,^a M. Nawaz Tahir,^b ^* Rana Muhammad Irfan,^a Shahid Iqbal ^a and Mahreen Zaneb ^a

^aUniversity of Sargodha, Department of Chemistry, Sargodha, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 24 July 2012; accepted 25 July 2012; online 28 July 2012)

In the title compound, C₁₉H₂₅NO₂, the 3-ethoxy-2-hydroxybenzaldehyde group is almost planar (r.m.s. deviation = 0.029 Å). An intramolecular O—H⋯N hydrogen bond generates an S(6) ring. There are no intermolecular hydrogen bonds.

Related literature

For a related structure, see: Fernandez et al. (2001 ).

Experimental

Crystal data

C₁₉H₂₅NO₂
M_r = 299.40
Monoclinic, P 2₁ /c
a = 18.9892 (16) Å
b = 6.7660 (5) Å
c = 13.0072 (10) Å
β = 95.958 (3)°
V = 1662.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.35 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.975, T_max = 0.985
8977 measured reflections
3006 independent reflections
2074 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.158
S = 1.05
3006 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.593 (2)	148

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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/S1600536812033594/hb6914sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812033594/hb6914Isup2.hkl

checkCIF report

Comment top

The title compound (Fig. 1) has been synthesized as a derivative for the complexation and other studies.

The crystal structures of N-(1-adamantyl)salicylaldamine (Fernandez et al. 2001) has been published which is related to the title compound.

In the title compound the 3-adamantylamine the bond lengths and bond angles have normal values. The 3-ethoxy-2-hydroxybenzaldehyde group is planar with r.m.s. deviation of 0.0292 Å. There exist strong intramolecular H-bonding of O—H···N type (Table 1, Fig. 1) and S(6) ring motif is formed. There does not exist any intermolecular H-bonding.

Related literature top

For a related structure, see: Fernandez et al. (2001).

Experimental top

Equimolar quantities of 3-adamantylamine and 3-ethoxy-2-hydroxybenzaldehyde were refluxed in ethanol for 2 h and yellow prisms of (I) were obtained after 72 h by the slow evaporation of the solvent at room temperature.

Structure description top

The title compound (Fig. 1) has been synthesized as a derivative for the complexation and other studies.

The crystal structures of N-(1-adamantyl)salicylaldamine (Fernandez et al. 2001) has been published which is related to the title compound.

For a related structure, see: Fernandez et al. (2001).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 displacement ellipsoids drawn at the 50% probability level. The dotted line represents the intramolecular hydrogen bond.

2-[(E)-N-(Adamantan-1-yl)carboximidoyl]-6-ethoxyphenol top

Crystal data top

C₁₉H₂₅NO₂	F(000) = 648
M_r = 299.40	D_x = 1.196 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2074 reflections
a = 18.9892 (16) Å	θ = 2.2–25.3°
b = 6.7660 (5) Å	µ = 0.08 mm⁻¹
c = 13.0072 (10) Å	T = 296 K
β = 95.958 (3)°	Prism, yellow
V = 1662.2 (2) Å³	0.35 × 0.28 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3006 independent reflections
Radiation source: fine-focus sealed tube	2074 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.2°
ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→7
T_min = 0.975, T_max = 0.985	l = −15→14
8977 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0682P)² + 0.6627P] where P = (F_o² + 2F_c²)/3
3006 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₉H₂₅NO₂	V = 1662.2 (2) Å³
M_r = 299.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.9892 (16) Å	µ = 0.08 mm⁻¹
b = 6.7660 (5) Å	T = 296 K
c = 13.0072 (10) Å	0.35 × 0.28 × 0.25 mm
β = 95.958 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3006 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2074 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.985	R_int = 0.028
8977 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
3006 reflections	Δρ_min = −0.17 e Å⁻³
201 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	0.18741 (9)	−0.1124 (2)	0.42066 (12)	0.0557 (6)
O2	0.10146 (9)	−0.0658 (2)	0.56419 (12)	0.0616 (6)
N1	0.25760 (9)	0.0401 (3)	0.27943 (13)	0.0460 (6)
C1	0.30814 (11)	0.0164 (3)	0.20220 (15)	0.0426 (7)
C2	0.30683 (15)	0.1799 (4)	0.12148 (19)	0.0643 (9)
C3	0.36170 (16)	0.1346 (4)	0.0448 (2)	0.0716 (10)
C4	0.43359 (16)	0.1258 (5)	0.1053 (3)	0.0863 (12)
C5	0.43686 (15)	−0.0407 (5)	0.1834 (2)	0.0802 (11)
C6	0.38174 (13)	0.0023 (5)	0.2599 (2)	0.0710 (10)
C7	0.29071 (14)	−0.1797 (4)	0.1462 (2)	0.0646 (9)
C8	0.34638 (15)	−0.2240 (4)	0.0709 (2)	0.0688 (10)
C9	0.41789 (16)	−0.2344 (4)	0.1310 (3)	0.0820 (11)
C10	0.34335 (16)	−0.0602 (4)	−0.0073 (2)	0.0746 (10)
C11	0.22809 (11)	0.2044 (3)	0.29534 (16)	0.0445 (7)
C12	0.18045 (11)	0.2304 (3)	0.37448 (15)	0.0408 (6)
C13	0.16242 (11)	0.0702 (3)	0.43468 (16)	0.0415 (7)
C14	0.11691 (11)	0.0998 (3)	0.51114 (16)	0.0453 (7)
C15	0.09234 (12)	0.2874 (3)	0.52875 (18)	0.0551 (8)
C16	0.11149 (13)	0.4469 (3)	0.47037 (19)	0.0580 (8)
C17	0.15451 (12)	0.4186 (3)	0.39414 (17)	0.0497 (7)
C18	0.05855 (13)	−0.0432 (4)	0.64640 (18)	0.0596 (8)
C19	0.05370 (18)	−0.2399 (4)	0.6973 (2)	0.0825 (11)
H1	0.21393	−0.11002	0.37479	0.0835*
H2A	0.31785	0.30560	0.15522	0.0772*
H2B	0.25991	0.18906	0.08441	0.0772*
H3	0.36090	0.23963	−0.00722	0.0857*
H4A	0.44339	0.25035	0.14086	0.1035*
H4B	0.46944	0.10551	0.05839	0.1035*
H5	0.48437	−0.04838	0.22057	0.0964*
H6A	0.38278	−0.10251	0.31092	0.0851*
H6B	0.39340	0.12553	0.29582	0.0851*
H7A	0.24405	−0.17209	0.10823	0.0775*
H7B	0.29033	−0.28569	0.19639	0.0775*
H8	0.33547	−0.35033	0.03600	0.0825*
H9A	0.45306	−0.26720	0.08468	0.0984*
H9B	0.41810	−0.33803	0.18250	0.0984*
H10A	0.29614	−0.05317	−0.04361	0.0895*
H10B	0.37638	−0.08758	−0.05763	0.0895*
H11	0.23744	0.31231	0.25458	0.0534*
H15	0.06262	0.30738	0.58030	0.0662*
H16	0.09494	0.57293	0.48333	0.0695*
H17	0.16675	0.52549	0.35474	0.0597*
H18A	0.01173	0.00252	0.61999	0.0716*
H18B	0.07941	0.05308	0.69578	0.0716*
H19A	0.10031	−0.29447	0.71201	0.1236*
H19B	0.02528	−0.32722	0.65201	0.1236*
H19C	0.03238	−0.22430	0.76057	0.1236*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0775 (12)	0.0295 (8)	0.0652 (10)	0.0063 (7)	0.0323 (8)	0.0032 (7)
O2	0.0801 (12)	0.0453 (9)	0.0655 (10)	−0.0012 (8)	0.0373 (9)	0.0021 (8)
N1	0.0572 (11)	0.0347 (10)	0.0476 (10)	0.0018 (8)	0.0123 (9)	0.0019 (8)
C1	0.0505 (12)	0.0363 (11)	0.0421 (11)	0.0029 (9)	0.0099 (9)	0.0011 (9)
C2	0.0833 (18)	0.0520 (14)	0.0615 (15)	0.0105 (13)	0.0257 (13)	0.0061 (12)
C3	0.093 (2)	0.0592 (17)	0.0673 (16)	0.0058 (14)	0.0314 (15)	0.0138 (14)
C4	0.082 (2)	0.081 (2)	0.103 (2)	−0.0267 (17)	0.0432 (18)	−0.0229 (19)
C5	0.0530 (16)	0.104 (2)	0.0823 (19)	0.0053 (16)	0.0004 (14)	−0.0090 (19)
C6	0.0649 (16)	0.088 (2)	0.0594 (15)	0.0051 (15)	0.0026 (13)	−0.0030 (14)
C7	0.0686 (16)	0.0498 (14)	0.0779 (17)	−0.0026 (12)	0.0194 (14)	−0.0106 (13)
C8	0.0762 (18)	0.0523 (15)	0.0799 (18)	0.0004 (13)	0.0184 (15)	−0.0162 (14)
C9	0.0751 (19)	0.075 (2)	0.099 (2)	0.0268 (16)	0.0233 (17)	0.0066 (17)
C10	0.0787 (18)	0.087 (2)	0.0590 (15)	0.0130 (16)	0.0114 (14)	−0.0144 (15)
C11	0.0547 (13)	0.0335 (11)	0.0460 (12)	−0.0028 (10)	0.0087 (10)	0.0035 (9)
C12	0.0473 (12)	0.0320 (10)	0.0435 (11)	−0.0008 (9)	0.0062 (9)	−0.0002 (9)
C13	0.0476 (12)	0.0297 (10)	0.0472 (12)	0.0010 (9)	0.0053 (9)	−0.0039 (9)
C14	0.0510 (13)	0.0377 (12)	0.0485 (12)	−0.0017 (10)	0.0112 (10)	−0.0014 (10)
C15	0.0586 (14)	0.0498 (14)	0.0596 (14)	0.0061 (11)	0.0185 (11)	−0.0095 (12)
C16	0.0674 (15)	0.0353 (12)	0.0726 (16)	0.0121 (11)	0.0140 (13)	−0.0067 (11)
C17	0.0615 (14)	0.0308 (11)	0.0574 (13)	0.0039 (10)	0.0084 (11)	0.0023 (10)
C18	0.0660 (15)	0.0659 (16)	0.0503 (13)	−0.0106 (12)	0.0216 (12)	−0.0087 (12)
C19	0.108 (2)	0.081 (2)	0.0640 (17)	−0.0329 (17)	0.0350 (16)	−0.0010 (15)

Geometric parameters (Å, º) top

O1—C13	1.343 (2)	C18—C19	1.494 (4)
O2—C14	1.364 (3)	C2—H2A	0.9700
O2—C18	1.418 (3)	C2—H2B	0.9700
O1—H1	0.8200	C3—H3	0.9800
N1—C11	1.272 (3)	C4—H4A	0.9700
N1—C1	1.468 (3)	C4—H4B	0.9700
C1—C2	1.524 (3)	C5—H5	0.9800
C1—C6	1.519 (3)	C6—H6A	0.9700
C1—C7	1.533 (3)	C6—H6B	0.9700
C2—C3	1.546 (4)	C7—H7A	0.9700
C3—C4	1.505 (4)	C7—H7B	0.9700
C3—C10	1.506 (4)	C8—H8	0.9800
C4—C5	1.514 (5)	C9—H9A	0.9700
C5—C9	1.504 (4)	C9—H9B	0.9700
C5—C6	1.545 (4)	C10—H10A	0.9700
C7—C8	1.543 (4)	C10—H10B	0.9700
C8—C10	1.501 (4)	C11—H11	0.9300
C8—C9	1.497 (4)	C15—H15	0.9300
C11—C12	1.450 (3)	C16—H16	0.9300
C12—C17	1.398 (3)	C17—H17	0.9300
C12—C13	1.400 (3)	C18—H18A	0.9700
C13—C14	1.398 (3)	C18—H18B	0.9700
C14—C15	1.380 (3)	C19—H19A	0.9600
C15—C16	1.390 (3)	C19—H19B	0.9600
C16—C17	1.362 (3)	C19—H19C	0.9600

C14—O2—C18	117.61 (17)	C5—C4—H4A	110.00
C13—O1—H1	109.00	C5—C4—H4B	110.00
C1—N1—C11	122.50 (19)	H4A—C4—H4B	108.00
N1—C1—C2	115.28 (19)	C4—C5—H5	110.00
N1—C1—C7	107.18 (18)	C6—C5—H5	110.00
C2—C1—C6	109.5 (2)	C9—C5—H5	110.00
N1—C1—C6	107.58 (17)	C1—C6—H6A	110.00
C6—C1—C7	108.8 (2)	C1—C6—H6B	110.00
C2—C1—C7	108.28 (18)	C5—C6—H6A	110.00
C1—C2—C3	109.7 (2)	C5—C6—H6B	110.00
C2—C3—C10	108.9 (2)	H6A—C6—H6B	108.00
C4—C3—C10	110.8 (2)	C1—C7—H7A	110.00
C2—C3—C4	107.8 (2)	C1—C7—H7B	110.00
C3—C4—C5	110.6 (3)	C8—C7—H7A	110.00
C4—C5—C6	108.0 (3)	C8—C7—H7B	110.00
C4—C5—C9	110.7 (3)	H7A—C7—H7B	108.00
C6—C5—C9	108.0 (3)	C7—C8—H8	110.00
C1—C6—C5	110.1 (2)	C9—C8—H8	110.00
C1—C7—C8	110.0 (2)	C10—C8—H8	110.00
C7—C8—C9	108.8 (2)	C5—C9—H9A	109.00
C9—C8—C10	111.0 (2)	C5—C9—H9B	109.00
C7—C8—C10	107.8 (2)	C8—C9—H9A	109.00
C5—C9—C8	111.0 (2)	C8—C9—H9B	109.00
C3—C10—C8	110.5 (2)	H9A—C9—H9B	108.00
N1—C11—C12	122.66 (19)	C3—C10—H10A	110.00
C11—C12—C17	119.86 (19)	C3—C10—H10B	110.00
C13—C12—C17	119.43 (19)	C8—C10—H10A	110.00
C11—C12—C13	120.66 (18)	C8—C10—H10B	110.00
O1—C13—C14	118.80 (18)	H10A—C10—H10B	108.00
C12—C13—C14	119.47 (19)	N1—C11—H11	119.00
O1—C13—C12	121.73 (19)	C12—C11—H11	119.00
O2—C14—C15	125.29 (19)	C14—C15—H15	120.00
C13—C14—C15	119.64 (19)	C16—C15—H15	120.00
O2—C14—C13	115.06 (18)	C15—C16—H16	120.00
C14—C15—C16	120.8 (2)	C17—C16—H16	120.00
C15—C16—C17	120.0 (2)	C12—C17—H17	120.00
C12—C17—C16	120.69 (19)	C16—C17—H17	120.00
O2—C18—C19	107.8 (2)	O2—C18—H18A	110.00
C1—C2—H2A	110.00	O2—C18—H18B	110.00
C1—C2—H2B	110.00	C19—C18—H18A	110.00
C3—C2—H2A	110.00	C19—C18—H18B	110.00
C3—C2—H2B	110.00	H18A—C18—H18B	108.00
H2A—C2—H2B	108.00	C18—C19—H19A	109.00
C2—C3—H3	110.00	C18—C19—H19B	109.00
C4—C3—H3	110.00	C18—C19—H19C	109.00
C10—C3—H3	110.00	H19A—C19—H19B	109.00
C3—C4—H4A	109.00	H19A—C19—H19C	109.00
C3—C4—H4B	110.00	H19B—C19—H19C	109.00

C18—O2—C14—C13	176.74 (19)	C9—C5—C6—C1	−60.4 (3)
C18—O2—C14—C15	−2.2 (3)	C4—C5—C9—C8	−56.4 (3)
C14—O2—C18—C19	−175.7 (2)	C6—C5—C9—C8	61.6 (3)
C11—N1—C1—C2	−17.3 (3)	C1—C7—C8—C9	59.1 (3)
C11—N1—C1—C6	105.2 (2)	C1—C7—C8—C10	−61.3 (3)
C11—N1—C1—C7	−137.9 (2)	C7—C8—C9—C5	−61.3 (3)
C1—N1—C11—C12	−177.34 (18)	C10—C8—C9—C5	57.1 (3)
N1—C1—C2—C3	−179.26 (19)	C7—C8—C10—C3	61.8 (3)
C6—C1—C2—C3	59.3 (3)	C9—C8—C10—C3	−57.2 (3)
C7—C1—C2—C3	−59.3 (3)	N1—C11—C12—C13	−2.8 (3)
N1—C1—C6—C5	175.2 (2)	N1—C11—C12—C17	174.5 (2)
C2—C1—C6—C5	−58.8 (3)	C11—C12—C13—O1	−1.0 (3)
C7—C1—C6—C5	59.4 (3)	C11—C12—C13—C14	179.38 (19)
N1—C1—C7—C8	−174.59 (19)	C17—C12—C13—O1	−178.3 (2)
C2—C1—C7—C8	60.5 (3)	C17—C12—C13—C14	2.1 (3)
C6—C1—C7—C8	−58.5 (2)	C11—C12—C17—C16	−177.9 (2)
C1—C2—C3—C4	−60.5 (3)	C13—C12—C17—C16	−0.6 (3)
C1—C2—C3—C10	59.8 (3)	O1—C13—C14—O2	−0.9 (3)
C2—C3—C4—C5	62.6 (3)	O1—C13—C14—C15	178.1 (2)
C10—C3—C4—C5	−56.5 (3)	C12—C13—C14—O2	178.77 (18)
C2—C3—C10—C8	−61.5 (3)	C12—C13—C14—C15	−2.3 (3)
C4—C3—C10—C8	57.0 (3)	O2—C14—C15—C16	179.8 (2)
C3—C4—C5—C6	−62.0 (3)	C13—C14—C15—C16	0.9 (3)
C3—C4—C5—C9	56.1 (3)	C14—C15—C16—C17	0.6 (4)
C4—C5—C6—C1	59.3 (3)	C15—C16—C17—C12	−0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.593 (2)	148

Experimental details

Crystal data
Chemical formula	C₁₉H₂₅NO₂
M_r	299.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.9892 (16), 6.7660 (5), 13.0072 (10)
β (°)	95.958 (3)
V (Å³)	1662.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.28 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.975, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	8977, 3006, 2074
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.158, 1.05
No. of reflections	3006
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.17

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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···N1	0.82	1.86	2.593 (2)	148

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. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fernandez, J. M., del Rio-Portilla, G. F., Quiroz-Garcia, B., Toscano, R. A. & Salcedo, R. (2001). J. Mol. Struct. 561, 197–207. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar