2-(Naphthalene-2-sulfonamido)-3-phenyl­propanoic acid

Mubashar-ur-Rehman, H.; Arshad, M.N.; Asiri, A.M.; Khan, I.U.; Bilal, M.

doi:10.1107/S1600536813000081

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o194

doi:10.1107/S1600536813000081

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2-(Naphthalene-2-sulfonamido)-3-phenylpropanoic acid

Hafiz Mubashar-ur-Rehman,^a ^* Muhammad Nadeem Arshad,^b ^* Abdullah M. Asiri,^c,^b Islam Ullah Khan ^a and Muhammad Bilal ^d

^aDepartment of Chemistry, Materials Chemistry Laboratory, GC University, Lahore 54000, Pakistan, ^bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^dDepartment of Chemistry, University of Engineering & Technology, Lahore 54000, Pakistan
^*Correspondence e-mail: malikg781@yahoo.com, mnachemist@hotmail.com

(Received 23 December 2012; accepted 2 January 2013; online 9 January 2013)

In the title compound, C₁₉H₁₇NO₄S, the phenyl ring and the naphthalene ring system are oriented at a dihedral angle of 4.12 (2)° and the molecule adopts a U-shaped conformation. The C_c—C—N—S (c = carboxy) torsion angle is 90.98 (15)°. In the crystal, molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds, resulting in (100) chains incorporating centrosymmetric R²₂(14) and R²₂(10) loops. Weak aromatic π–π stacking is also observed [centroid–centroid separations = 3.963 (2) and 3.932 (2) Å].

Related literature

For the synthesis and related structures, see: Arshad et al. (2012 ); Khan et al. (2012 ).

Experimental

Crystal data

C₁₉H₁₇NO₄S
M_r = 355.40
Monoclinic, P 2₁ /n
a = 8.0694 (2) Å
b = 15.2168 (4) Å
c = 14.0996 (3) Å
β = 92.505 (2)°
V = 1729.64 (7) Å³
Z = 4
Cu Kα radiation
μ = 1.87 mm⁻¹
T = 296 K
0.29 × 0.10 × 0.09 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.784, T_max = 1.000
13588 measured reflections
3486 independent reflections
2813 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.118
S = 1.03
3486 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.80 (2)	2.18 (2)	2.964 (2)	164 (2)
O4—H1O⋯O2ⁱⁱ	0.88 (3)	1.90 (3)	2.772 (2)	174 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012 ) and X-SEED (Barbour, 2001 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000081/hb7020sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000081/hb7020Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000081/hb7020Isup3.cml

checkCIF report

Comment top

In countinuation of our studies of the synthesis of sulfonamide derivatives of amino acids (Khan et al., 2012) & (Arshad et al., 2012) we now report the crystal structure of title compound.

In the structure of molecule the naphthalene and benzene rings are almost parallel, since the dihedral angle is as small as 4.12 (2)°. The sulfur (S1) atom as usual adopted the distorted tetrahedral geometry with O1-S1-O2 angle of 118.96 (9)°. The O—H···O type intermolecular hudrogen bonding connects the molecules to form inversion dimers and resulting in fourteen R²₂(14) membered ring motifs. On the othe other hand, these dimers connected through another N—H···O type link to give ten R²₂(10) membered ring motif and generates a long chain along the a axis direction (Table. 1, Fig. 2). The presence of π-π stacking interactions between aromatic rings is also observed: Cg1-Cg2 (Cg1: C1-C6; Cg2: C5-C10) with distances of 3.963 (2) Å (1 - x, 1 - y, 2 - z) and Cg2-Cg2 with distances of 3.932 (2) Å (1 - x, 1 -y , 2 - z).

Related literature top

For the synthesis and related structures, see: Arshad et al. (2012); Khan et al. (2012).

Experimental top

The title compound was synthesised following the literature method (Arshad et al., 2012) and recrystallized from methanol solution as colourless prisms by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).

Figures top

	Fig. 1. The molecular structure of C₁₉H₁₇NO₄S with 50% probability of thermal ellipsoids.
	Fig. 2. A perspective view showing O—H···O and N—H···O hydrogen bonds, drawn using dashed lines.

2-(Naphthalene-2-sulfonamido)-3-phenylpropanoic acid top

Crystal data top

C₁₉H₁₇NO₄S	F(000) = 744
M_r = 355.40	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 5975 reflections
a = 8.0694 (2) Å	θ = 3.1–74.6°
b = 15.2168 (4) Å	µ = 1.87 mm⁻¹
c = 14.0996 (3) Å	T = 296 K
β = 92.505 (2)°	Prismatic, colorless
V = 1729.64 (7) Å³	0.29 × 0.10 × 0.09 mm
Z = 4

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer	3486 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2813 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.026
ω scans	θ_max = 74.7°, θ_min = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −9→9
T_min = 0.784, T_max = 1.000	k = −18→18
13588 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0591P)² + 0.4657P] where P = (F_o² + 2F_c²)/3
3486 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₉H₁₇NO₄S	V = 1729.64 (7) Å³
M_r = 355.40	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 8.0694 (2) Å	µ = 1.87 mm⁻¹
b = 15.2168 (4) Å	T = 296 K
c = 14.0996 (3) Å	0.29 × 0.10 × 0.09 mm
β = 92.505 (2)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer	3486 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2813 reflections with I > 2σ(I)
T_min = 0.784, T_max = 1.000	R_int = 0.026
13588 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.28 e Å⁻³
3486 reflections	Δρ_min = −0.37 e Å⁻³
232 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.31495 (6)	0.52701 (3)	0.68873 (3)	0.05113 (16)
O1	0.4041 (2)	0.60690 (9)	0.70303 (11)	0.0687 (4)
O2	0.14144 (17)	0.53082 (11)	0.66184 (11)	0.0707 (4)
O3	0.24930 (18)	0.47490 (10)	0.41829 (10)	0.0647 (4)
O4	0.05674 (17)	0.39149 (11)	0.48022 (11)	0.0671 (4)
N1	0.40035 (19)	0.47399 (10)	0.60505 (10)	0.0470 (4)
C1	0.3324 (2)	0.46054 (13)	0.79139 (13)	0.0521 (4)
C2	0.1937 (3)	0.41529 (18)	0.81402 (16)	0.0749 (6)
H2	0.0955	0.4223	0.7778	0.090*
C3	0.1997 (4)	0.3582 (2)	0.8920 (2)	0.1020 (10)
H3	0.1058	0.3263	0.9066	0.122*
C4	0.3406 (4)	0.3492 (2)	0.9463 (2)	0.0980 (9)
H4	0.3416	0.3119	0.9985	0.118*
C5	0.4860 (3)	0.39491 (16)	0.92563 (15)	0.0706 (6)
C6	0.4857 (2)	0.45189 (13)	0.84526 (13)	0.0524 (4)
C7	0.6347 (3)	0.49537 (16)	0.82581 (15)	0.0623 (5)
H7	0.6387	0.5319	0.7731	0.075*
C8	0.7732 (3)	0.4843 (2)	0.88355 (19)	0.0839 (8)
H8	0.8705	0.5135	0.8697	0.101*
C9	0.7708 (4)	0.4296 (2)	0.9636 (2)	0.0969 (9)
H9	0.8656	0.4234	1.0030	0.116*
C10	0.6320 (4)	0.3866 (2)	0.98330 (18)	0.0909 (9)
H10	0.6320	0.3502	1.0363	0.109*
C11	0.3160 (2)	0.39725 (12)	0.56401 (12)	0.0454 (4)
H11	0.2472	0.3704	0.6117	0.054*
C12	0.4398 (2)	0.32926 (13)	0.53018 (13)	0.0535 (4)
H12A	0.3793	0.2812	0.4996	0.064*
H12B	0.5084	0.3561	0.4834	0.064*
C13	0.5497 (2)	0.29330 (12)	0.61016 (13)	0.0516 (4)
C14	0.4856 (4)	0.23896 (18)	0.6765 (2)	0.0874 (8)
H14	0.3741	0.2234	0.6713	0.105*
C15	0.5838 (5)	0.2070 (2)	0.7509 (2)	0.1202 (12)
H15	0.5374	0.1712	0.7961	0.144*
C16	0.7457 (5)	0.2268 (2)	0.7590 (2)	0.1056 (11)
H16	0.8113	0.2041	0.8091	0.127*
C17	0.8139 (3)	0.28037 (19)	0.6937 (2)	0.0895 (9)
H17	0.9262	0.2943	0.6992	0.107*
C18	0.7150 (3)	0.31431 (15)	0.61838 (17)	0.0665 (5)
H18	0.7613	0.3511	0.5739	0.080*
C19	0.2050 (2)	0.42710 (13)	0.47926 (13)	0.0491 (4)
H1N	0.499 (3)	0.4785 (14)	0.6034 (16)	0.059*
H1O	−0.004 (3)	0.4135 (16)	0.4325 (18)	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0438 (3)	0.0605 (3)	0.0478 (3)	0.00944 (19)	−0.01179 (18)	−0.00627 (19)
O1	0.0815 (10)	0.0540 (8)	0.0685 (9)	0.0020 (7)	−0.0201 (8)	−0.0057 (7)
O2	0.0465 (8)	0.0973 (11)	0.0667 (9)	0.0235 (7)	−0.0148 (6)	−0.0138 (8)
O3	0.0578 (9)	0.0813 (10)	0.0536 (8)	−0.0026 (7)	−0.0119 (6)	0.0181 (7)
O4	0.0452 (8)	0.0972 (11)	0.0578 (8)	−0.0087 (7)	−0.0101 (6)	0.0008 (8)
N1	0.0368 (7)	0.0587 (9)	0.0449 (8)	−0.0018 (7)	−0.0044 (6)	−0.0024 (6)
C1	0.0458 (10)	0.0687 (12)	0.0417 (9)	−0.0002 (8)	−0.0003 (7)	−0.0060 (8)
C2	0.0590 (13)	0.1014 (18)	0.0645 (13)	−0.0162 (12)	0.0052 (10)	−0.0047 (12)
C3	0.097 (2)	0.123 (2)	0.0877 (19)	−0.0394 (19)	0.0219 (17)	0.0136 (18)
C4	0.120 (3)	0.106 (2)	0.0686 (16)	−0.0131 (19)	0.0126 (16)	0.0233 (15)
C5	0.0856 (16)	0.0774 (14)	0.0485 (11)	0.0091 (12)	−0.0012 (10)	0.0035 (10)
C6	0.0518 (11)	0.0639 (11)	0.0412 (9)	0.0067 (8)	−0.0035 (7)	−0.0039 (8)
C7	0.0483 (11)	0.0830 (14)	0.0547 (11)	0.0030 (10)	−0.0083 (9)	0.0009 (10)
C8	0.0529 (14)	0.117 (2)	0.0803 (16)	0.0082 (13)	−0.0203 (12)	−0.0049 (15)
C9	0.085 (2)	0.127 (2)	0.0751 (17)	0.0339 (19)	−0.0363 (15)	−0.0053 (16)
C10	0.112 (2)	0.102 (2)	0.0563 (13)	0.0313 (18)	−0.0201 (14)	0.0092 (13)
C11	0.0428 (9)	0.0535 (10)	0.0394 (8)	−0.0005 (7)	−0.0033 (7)	0.0017 (7)
C12	0.0599 (11)	0.0562 (10)	0.0439 (9)	0.0092 (9)	−0.0029 (8)	0.0030 (8)
C13	0.0578 (11)	0.0459 (9)	0.0503 (10)	0.0072 (8)	−0.0056 (8)	0.0027 (8)
C14	0.0871 (18)	0.0854 (17)	0.0880 (17)	−0.0149 (14)	−0.0151 (14)	0.0390 (14)
C15	0.137 (3)	0.119 (3)	0.102 (2)	−0.004 (2)	−0.026 (2)	0.065 (2)
C16	0.136 (3)	0.093 (2)	0.0835 (19)	0.028 (2)	−0.0475 (19)	0.0104 (16)
C17	0.0658 (16)	0.0867 (18)	0.113 (2)	0.0183 (13)	−0.0335 (15)	−0.0249 (17)
C18	0.0580 (12)	0.0615 (12)	0.0798 (14)	0.0071 (10)	−0.0015 (10)	−0.0006 (11)
C19	0.0409 (9)	0.0603 (11)	0.0456 (9)	0.0028 (8)	−0.0032 (7)	−0.0083 (8)

Geometric parameters (Å, º) top

S1—O1	1.4226 (15)	C8—C9	1.404 (4)
S1—O2	1.4356 (14)	C8—H8	0.9300
S1—N1	1.6090 (16)	C9—C10	1.337 (4)
S1—C1	1.766 (2)	C9—H9	0.9300
O3—C19	1.193 (2)	C10—H10	0.9300
O4—C19	1.314 (2)	C11—C12	1.529 (2)
O4—H1O	0.88 (3)	C11—C19	1.531 (2)
N1—C11	1.459 (2)	C11—H11	0.9800
N1—H1N	0.80 (2)	C12—C13	1.507 (2)
C1—C2	1.364 (3)	C12—H12A	0.9700
C1—C6	1.430 (3)	C12—H12B	0.9700
C2—C3	1.401 (4)	C13—C14	1.367 (3)
C2—H2	0.9300	C13—C18	1.372 (3)
C3—C4	1.350 (4)	C14—C15	1.376 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.405 (4)	C15—C16	1.340 (5)
C4—H4	0.9300	C15—H15	0.9300
C5—C10	1.408 (4)	C16—C17	1.364 (5)
C5—C6	1.427 (3)	C16—H16	0.9300
C6—C7	1.410 (3)	C17—C18	1.399 (3)
C7—C8	1.364 (3)	C17—H17	0.9300
C7—H7	0.9300	C18—H18	0.9300

O1—S1—O2	118.96 (9)	C9—C10—C5	121.6 (2)
O1—S1—N1	107.60 (9)	C9—C10—H10	119.2
O2—S1—N1	105.70 (8)	C5—C10—H10	119.2
O1—S1—C1	110.58 (9)	N1—C11—C12	111.45 (15)
O2—S1—C1	106.34 (10)	N1—C11—C19	108.61 (14)
N1—S1—C1	107.01 (9)	C12—C11—C19	108.98 (14)
C19—O4—H1O	108.0 (16)	N1—C11—H11	109.3
C11—N1—S1	119.01 (12)	C12—C11—H11	109.3
C11—N1—H1N	120.3 (16)	C19—C11—H11	109.3
S1—N1—H1N	115.9 (16)	C13—C12—C11	112.56 (15)
C2—C1—C6	122.0 (2)	C13—C12—H12A	109.1
C2—C1—S1	116.37 (16)	C11—C12—H12A	109.1
C6—C1—S1	121.61 (15)	C13—C12—H12B	109.1
C1—C2—C3	119.8 (2)	C11—C12—H12B	109.1
C1—C2—H2	120.1	H12A—C12—H12B	107.8
C3—C2—H2	120.1	C14—C13—C18	118.6 (2)
C4—C3—C2	120.5 (3)	C14—C13—C12	120.2 (2)
C4—C3—H3	119.8	C18—C13—C12	121.15 (19)
C2—C3—H3	119.8	C13—C14—C15	120.8 (3)
C3—C4—C5	121.5 (3)	C13—C14—H14	119.6
C3—C4—H4	119.2	C15—C14—H14	119.6
C5—C4—H4	119.2	C16—C15—C14	120.8 (3)
C4—C5—C10	121.4 (2)	C16—C15—H15	119.6
C4—C5—C6	119.5 (2)	C14—C15—H15	119.6
C10—C5—C6	119.1 (2)	C15—C16—C17	119.8 (3)
C7—C6—C5	117.90 (19)	C15—C16—H16	120.1
C7—C6—C1	125.40 (18)	C17—C16—H16	120.1
C5—C6—C1	116.69 (19)	C16—C17—C18	120.0 (3)
C8—C7—C6	120.6 (2)	C16—C17—H17	120.0
C8—C7—H7	119.7	C18—C17—H17	120.0
C6—C7—H7	119.7	C13—C18—C17	119.9 (2)
C7—C8—C9	120.9 (3)	C13—C18—H18	120.0
C7—C8—H8	119.5	C17—C18—H18	120.0
C9—C8—H8	119.5	O3—C19—O4	124.08 (17)
C10—C9—C8	119.9 (2)	O3—C19—C11	124.07 (16)
C10—C9—H9	120.0	O4—C19—C11	111.81 (17)
C8—C9—H9	120.0

O1—S1—N1—C11	−168.97 (13)	C1—C6—C7—C8	178.1 (2)
O2—S1—N1—C11	−40.88 (15)	C6—C7—C8—C9	−0.1 (4)
C1—S1—N1—C11	72.17 (15)	C7—C8—C9—C10	1.0 (5)
O1—S1—C1—C2	141.61 (17)	C8—C9—C10—C5	−0.4 (5)
O2—S1—C1—C2	11.1 (2)	C4—C5—C10—C9	179.7 (3)
N1—S1—C1—C2	−101.49 (18)	C6—C5—C10—C9	−1.1 (4)
O1—S1—C1—C6	−41.01 (18)	S1—N1—C11—C12	−148.96 (13)
O2—S1—C1—C6	−171.48 (15)	S1—N1—C11—C19	90.98 (15)
N1—S1—C1—C6	75.89 (17)	N1—C11—C12—C13	62.6 (2)
C6—C1—C2—C3	−0.1 (4)	C19—C11—C12—C13	−177.57 (16)
S1—C1—C2—C3	177.2 (2)	C11—C12—C13—C14	70.3 (3)
C1—C2—C3—C4	1.5 (5)	C11—C12—C13—C18	−109.5 (2)
C2—C3—C4—C5	−1.3 (5)	C18—C13—C14—C15	1.0 (4)
C3—C4—C5—C10	178.9 (3)	C12—C13—C14—C15	−178.8 (3)
C3—C4—C5—C6	−0.3 (4)	C13—C14—C15—C16	−1.5 (6)
C4—C5—C6—C7	−178.9 (2)	C14—C15—C16—C17	1.0 (6)
C10—C5—C6—C7	1.9 (3)	C15—C16—C17—C18	−0.1 (5)
C4—C5—C6—C1	1.6 (3)	C14—C13—C18—C17	−0.1 (3)
C10—C5—C6—C1	−177.6 (2)	C12—C13—C18—C17	179.6 (2)
C2—C1—C6—C7	179.1 (2)	C16—C17—C18—C13	−0.3 (4)
S1—C1—C6—C7	1.9 (3)	N1—C11—C19—O3	47.5 (2)
C2—C1—C6—C5	−1.4 (3)	C12—C11—C19—O3	−74.1 (2)
S1—C1—C6—C5	−178.65 (15)	N1—C11—C19—O4	−134.51 (16)
C5—C6—C7—C8	−1.4 (3)	C12—C11—C19—O4	103.90 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.80 (2)	2.18 (2)	2.964 (2)	164 (2)
O4—H1O···O2ⁱⁱ	0.88 (3)	1.90 (3)	2.772 (2)	174 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₄S
M_r	355.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.0694 (2), 15.2168 (4), 14.0996 (3)
β (°)	92.505 (2)
V (Å³)	1729.64 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.87
Crystal size (mm)	0.29 × 0.10 × 0.09

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.784, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13588, 3486, 2813
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.03
No. of reflections	3486
No. of parameters	232
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.37

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.80 (2)	2.18 (2)	2.964 (2)	164 (2)
O4—H1O···O2ⁱⁱ	0.88 (3)	1.90 (3)	2.772 (2)	174 (2)

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

Acknowledgements

The authors thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via Research Group Track grant No. 3-102/428.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
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