4-(5-Chloro­penta­namido)­benzene­sulfonamide

Türkmen, H.; Yalçın, Ş.P.; Akkurt, M.; Durgun, M.

doi:10.1107/S1600536812048118

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3475-o3476

doi:10.1107/S1600536812048118

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4-(5-Chloropentanamido)benzenesulfonamide

Hasan Türkmen,^a Şerife Pınar Yalçın,^b,^c Mehmet Akkurt ^d ^* and Mustafa Durgun ^a

^aDepartment of Chemistry, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey, ^bDepartment of Physics, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey, ^cCentral Research Lab, Harran University, Osmanbey Campus, 63300 Şanlıurfa, Turkey, and ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 20 November 2012; accepted 22 November 2012; online 28 November 2012)

The molecular conformation of the title compound, C₁₁H₁₅ClN₂O₃S, is stabilized by a C—H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by two pairs of inversion-related N—H⋯O hydrogen bonds, generating R₂²(8) and R₂²(20) ring motifs, resulting in chains running along [0-11]. These chains are connected by N—H⋯O hydrogen bonds along [100], forming layers parallel to (011). There are also C—H⋯π interactions between the layers, which consolidate the three-dimensional structure.

Related literature

Sulfonamides represent an important class of biologically active compounds. For their action as inhibitors of carbonic anhydrase enzyme, their antibacterial properties in chemotherapy, as antithyroid drugs, and for their antimicrobial properties, see: Maren (1987 ); Supuran (2008 ); Turkmen et al. (2005 , 2011 ); Rami et al. (2011 ). For their antiviral properties, such as HIV protease inhibitors, see: De Clercq (2001 ) and as inhibitors of cysteine protease enzyme, see: Danial & Korsmeyer (2004 ). For related structures, see: Yalçın et al. (2012 ); Akkurt et al. (2010a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₁H₁₅ClN₂O₃S
M_r = 290.77
Triclinic, $[P \overline 1]$
a = 8.4872 (1) Å
b = 8.7730 (2) Å
c = 10.4572 (3) Å
α = 73.711 (4)°
β = 85.281 (4)°
γ = 63.393 (3)°
V = 667.37 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 294 K
0.24 × 0.15 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.901, T_max = 0.949
20164 measured reflections
4036 independent reflections
2815 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.169
S = 1.05
4036 reflections
172 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3	0.93	2.25	2.809 (4)	118
N1—H1NA⋯O3ⁱ	0.87 (2)	1.99 (3)	2.865 (3)	176 (3)
N1—H1NB⋯O1ⁱⁱ	0.87 (3)	2.11 (2)	2.963 (3)	166 (4)
N2—H2N⋯O2ⁱⁱⁱ	0.88 (3)	2.17 (3)	3.021 (4)	166 (3)
C10—H10A⋯Cg1^iv	0.97	2.96	3.771 (3)	142
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y, -z+2; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812048118/su2531sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048118/su2531Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048118/su2531Isup3.cml

checkCIF report

Comment top

Sulfonamides represent an important class of biologically active compounds, with inhibitors of carbonic anhydrase enzyme, antibacterial properties in chemotherapy, antithyroid drugs, antimicrobial properties, (Maren, 1987; Rami et al., 2011; Supuran, 2008; Turkmen et al., 2005, 2011). Sulfonamides are also antiviral agents, such as as HIV protease inhibitors (De Clercq, 2001), and inhibitors of cysteine protease enzyme (Danial & Korsmeyer, 2004). The design and development of new sulfanilamide derivatives can help determine any structural requirements for improved biological activity. In this study, we have prepared and determined the crystal structure of the title compound.

In the 5-chloropentanamide moiety of the title compound, Fig. 1, the N2—C7—C8—C9, Cl1—C11—C10—C9 and O3—C7—C8—C9 torsion angles are 165.7 (2), 63.2 (3) and -16.5 (3) °, respectively. The bond lengths and bond angles are within the normal range and are comparable to those reported previously for the isomer 4-(3-chloro-2,2-dimethylpropanoylamino)-benzenesulfonamide (Yalçın et al., 2012) and other related compounds (Akkurt et al., 2010a,b).

A C—H···O hydrogen bond stabilizes the molecular conformation of the title molecule, forming a S(6) ring motif (Bernstein et al., 1995; Table 1). In the crystal, neighbouring molecules are linked by two pairs of intermolecular N—H···O hydrogen bonds (Table 1 & Fig. 2), forming inversion dimers with R²₂(8) and R²₂(20) ring motifs, into chains running along [0 -1 1]. These chains are connected by N—H···O hydrogen bonds along the [100] direction, forming layers parallel to the (011) plane. C—H···π interactions between these layers further help in stabilizing the supramolecular structure (Table 1).

Related literature top

Sulfonamides represent an important class of biologically active compounds. For their action as inhibitors of carbonic anhydrase enzyme, their antibacterial properties in chemotherapy, as antithyroid drugs, and for their antimicrobial properties, see: Maren (1987); Supuran (2008); Turkmen et al. (2005, 2011); Rami et al. (2011). For their antiviral properties, such as HIV protease inhibitors, see: De Clercq (2001) and as inhibitors of cysteine protease enzyme, see: Danial & Korsmeyer (2004). For related structures, see: Yalçın et al. (2012); Akkurt et al. (2010a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by a nucleophilic acyl substitution reaction of sulfanilamide with 5-chloropentanoylchloride. To a solution of 3.00 g (17.42 mmol) of sulfanilamide in 50.0 ml of THF, 4.41 ml (34.84 mmol) of NEM [N-ethylmaleimide] was added. A solution of 4.47 ml (34.84 mmol) of 5-chloropentanoylchloride in 20 ml of THF was added with stirring. A white precipitate of NEM.HCl salt was immediately observed. The reaction mixture was stirred at room temperature for 24 h, the progress of which was monitored by TLC (dichloromethane/methanol 6/1 v/v). The precipitate was filtered out and the filtrate collected was evaporated in vacuo to leave a residue. The residue was dissolved in ethyl acetate. The organic extract was washed with 3 M hydrochloric acid, then with saturated sodium bicarbonate solution and finally with brine. The extract was dried (MgSO₄) and concentrated by evaporation in vacuo to give a residue. Recrystallization (ethanol) afforded 3.80 g (75%) the title compound as a white solid [M.p. 458–461 K]. Crystals suitable for X-ray diffraction were grown by slow evaporation of a solution in ethanol/chloroform/dichloromethane (4/3/3 v/v).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The view of the molecular structure of the title molecule, with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial view along the a axis of the crystal packing of the title compound, showing the inversion dimers formed by N—H···O hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted for clarity.

4-(5-Chloropentanamido)benzenesulfonamide top

Crystal data top

C₁₁H₁₅ClN₂O₃S	Z = 2
M_r = 290.77	F(000) = 304
Triclinic, P1	D_x = 1.447 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4872 (1) Å	Cell parameters from 3036 reflections
b = 8.7730 (2) Å	θ = 2.7–30.5°
c = 10.4572 (3) Å	µ = 0.44 mm⁻¹
α = 73.711 (4)°	T = 294 K
β = 85.281 (4)°	Needle, pale yellow
γ = 63.393 (3)°	0.24 × 0.15 × 0.12 mm
V = 667.37 (3) Å³

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	4036 independent reflections
Radiation source: Sealed Tube	2815 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.068
Detector resolution: 10.0000 pixels mm^-1	θ_max = 30.5°, θ_min = 2.7°
dtprofit.ref scans	h = −12→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→12
T_min = 0.901, T_max = 0.949	l = −14→14
20164 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0677P)² + 0.2759P] where P = (F_o² + 2F_c²)/3
4036 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.42 e Å⁻³
3 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₁H₁₅ClN₂O₃S	γ = 63.393 (3)°
M_r = 290.77	V = 667.37 (3) Å³
Triclinic, P1	Z = 2
a = 8.4872 (1) Å	Mo Kα radiation
b = 8.7730 (2) Å	µ = 0.44 mm⁻¹
c = 10.4572 (3) Å	T = 294 K
α = 73.711 (4)°	0.24 × 0.15 × 0.12 mm
β = 85.281 (4)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	4036 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2815 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.949	R_int = 0.068
20164 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	3 restraints
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.42 e Å⁻³
4036 reflections	Δρ_min = −0.35 e Å⁻³
172 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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Cl1	0.72069 (11)	0.61911 (12)	−0.09175 (8)	0.0692 (3)
S1	−0.03920 (8)	0.03480 (8)	0.77585 (6)	0.0419 (2)
O1	0.0449 (2)	−0.1257 (2)	0.88113 (18)	0.0500 (6)
O2	−0.1417 (3)	0.0370 (3)	0.6723 (2)	0.0572 (7)
O3	0.3519 (2)	0.4839 (2)	0.35111 (19)	0.0552 (6)
N1	−0.1676 (3)	0.1842 (3)	0.8443 (2)	0.0535 (8)
N2	0.5163 (3)	0.2301 (3)	0.5050 (2)	0.0416 (6)
C1	0.1271 (3)	0.0902 (3)	0.6970 (2)	0.0398 (7)
C2	0.2959 (3)	0.0145 (3)	0.7555 (2)	0.0426 (7)
C3	0.4213 (3)	0.0629 (3)	0.6908 (2)	0.0434 (7)
C4	0.3823 (3)	0.1871 (3)	0.5670 (2)	0.0385 (7)
C5	0.2142 (4)	0.2581 (4)	0.5068 (3)	0.0586 (9)
C6	0.0901 (4)	0.2088 (4)	0.5723 (3)	0.0611 (10)
C7	0.4969 (3)	0.3716 (3)	0.4010 (2)	0.0389 (7)
C8	0.6648 (3)	0.3843 (3)	0.3549 (3)	0.0424 (7)
C9	0.6398 (3)	0.5164 (4)	0.2196 (3)	0.0479 (8)
C10	0.8041 (4)	0.5387 (4)	0.1751 (3)	0.0481 (8)
C11	0.7774 (5)	0.6762 (4)	0.0441 (3)	0.0614 (11)
H1NA	−0.226 (4)	0.288 (2)	0.788 (3)	0.0830*
H2	0.32410	−0.06880	0.83840	0.0510*
H1NB	−0.123 (4)	0.179 (5)	0.918 (2)	0.0830*
H2N	0.623 (2)	0.165 (4)	0.542 (3)	0.0830*
H3	0.53400	0.01160	0.73060	0.0520*
H5	0.18640	0.33860	0.42260	0.0700*
H6	−0.02150	0.25670	0.53150	0.0730*
H8A	0.75400	0.26840	0.35040	0.0510*
H8B	0.70720	0.41920	0.41990	0.0510*
H9A	0.60360	0.47760	0.15390	0.0570*
H9B	0.54550	0.63050	0.22290	0.0570*
H10A	0.84370	0.57130	0.24300	0.0580*
H10B	0.89650	0.42580	0.16730	0.0580*
H11A	0.88480	0.69000	0.02530	0.0740*
H11B	0.68420	0.78900	0.05110	0.0740*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0689 (5)	0.0792 (6)	0.0525 (4)	−0.0331 (4)	0.0030 (4)	−0.0072 (4)
S1	0.0379 (3)	0.0438 (3)	0.0432 (3)	−0.0228 (3)	−0.0011 (2)	−0.0018 (2)
O1	0.0490 (10)	0.0413 (9)	0.0534 (10)	−0.0225 (8)	−0.0011 (8)	0.0015 (8)
O2	0.0533 (11)	0.0741 (13)	0.0549 (11)	−0.0404 (10)	−0.0057 (9)	−0.0101 (10)
O3	0.0387 (10)	0.0531 (11)	0.0557 (11)	−0.0175 (9)	−0.0005 (8)	0.0077 (9)
N1	0.0487 (14)	0.0476 (13)	0.0476 (13)	−0.0144 (11)	0.0006 (11)	−0.0003 (10)
N2	0.0343 (10)	0.0437 (11)	0.0411 (11)	−0.0180 (9)	−0.0022 (8)	−0.0009 (9)
C1	0.0373 (12)	0.0411 (12)	0.0416 (12)	−0.0213 (10)	−0.0008 (10)	−0.0047 (10)
C2	0.0409 (13)	0.0424 (12)	0.0399 (12)	−0.0211 (11)	−0.0056 (10)	0.0023 (10)
C3	0.0342 (12)	0.0422 (12)	0.0455 (13)	−0.0153 (10)	−0.0078 (10)	0.0000 (10)
C4	0.0357 (12)	0.0432 (12)	0.0378 (11)	−0.0203 (10)	0.0003 (9)	−0.0076 (10)
C5	0.0488 (15)	0.0720 (18)	0.0456 (14)	−0.0362 (14)	−0.0149 (12)	0.0185 (13)
C6	0.0435 (15)	0.077 (2)	0.0528 (15)	−0.0348 (15)	−0.0160 (12)	0.0159 (14)
C7	0.0376 (12)	0.0420 (12)	0.0365 (11)	−0.0177 (10)	0.0035 (10)	−0.0101 (10)
C8	0.0365 (12)	0.0432 (12)	0.0464 (13)	−0.0186 (10)	0.0051 (10)	−0.0100 (10)
C9	0.0426 (14)	0.0565 (15)	0.0474 (14)	−0.0287 (12)	0.0048 (11)	−0.0076 (12)
C10	0.0458 (14)	0.0527 (15)	0.0517 (14)	−0.0292 (12)	0.0095 (12)	−0.0126 (12)
C11	0.0676 (19)	0.0628 (18)	0.0634 (18)	−0.0410 (16)	0.0158 (15)	−0.0143 (15)

Geometric parameters (Å, º) top

Cl1—C11	1.797 (4)	C7—C8	1.508 (4)
S1—O1	1.4365 (18)	C8—C9	1.516 (4)
S1—O2	1.435 (2)	C9—C10	1.512 (5)
S1—N1	1.593 (2)	C10—C11	1.504 (4)
S1—C1	1.763 (3)	C2—H2	0.9300
O3—C7	1.220 (3)	C3—H3	0.9300
N2—C4	1.408 (4)	C5—H5	0.9300
N2—C7	1.356 (3)	C6—H6	0.9300
N1—H1NA	0.87 (2)	C8—H8A	0.9700
N1—H1NB	0.87 (3)	C8—H8B	0.9700
N2—H2N	0.88 (3)	C9—H9A	0.9700
C1—C2	1.390 (4)	C9—H9B	0.9700
C1—C6	1.377 (4)	C10—H10A	0.9700
C2—C3	1.377 (4)	C10—H10B	0.9700
C3—C4	1.389 (3)	C11—H11A	0.9700
C4—C5	1.397 (4)	C11—H11B	0.9700
C5—C6	1.374 (5)

O1—S1—O2	118.85 (13)	C1—C2—H2	120.00
O1—S1—N1	106.87 (11)	C3—C2—H2	120.00
O1—S1—C1	107.57 (11)	C2—C3—H3	120.00
O2—S1—N1	107.06 (14)	C4—C3—H3	119.00
O2—S1—C1	106.58 (13)	C4—C5—H5	120.00
N1—S1—C1	109.75 (13)	C6—C5—H5	120.00
C4—N2—C7	127.3 (2)	C1—C6—H6	119.00
S1—N1—H1NB	114 (3)	C5—C6—H6	119.00
H1NA—N1—H1NB	119 (3)	C7—C8—H8A	109.00
S1—N1—H1NA	114.0 (18)	C7—C8—H8B	109.00
C7—N2—H2N	115.5 (19)	C9—C8—H8A	109.00
C4—N2—H2N	116.9 (18)	C9—C8—H8B	109.00
S1—C1—C6	119.1 (2)	H8A—C8—H8B	108.00
S1—C1—C2	121.99 (17)	C8—C9—H9A	109.00
C2—C1—C6	118.9 (3)	C8—C9—H9B	109.00
C1—C2—C3	120.0 (2)	C10—C9—H9A	109.00
C2—C3—C4	121.1 (2)	C10—C9—H9B	109.00
C3—C4—C5	118.6 (3)	H9A—C9—H9B	108.00
N2—C4—C5	122.8 (2)	C9—C10—H10A	109.00
N2—C4—C3	118.6 (2)	C9—C10—H10B	109.00
C4—C5—C6	119.8 (3)	C11—C10—H10A	109.00
C1—C6—C5	121.5 (3)	C11—C10—H10B	109.00
O3—C7—C8	122.4 (2)	H10A—C10—H10B	108.00
N2—C7—C8	115.8 (2)	Cl1—C11—H11A	109.00
O3—C7—N2	121.8 (3)	Cl1—C11—H11B	109.00
C7—C8—C9	112.6 (2)	C10—C11—H11A	109.00
C8—C9—C10	113.4 (2)	C10—C11—H11B	109.00
C9—C10—C11	113.6 (3)	H11A—C11—H11B	108.00
Cl1—C11—C10	112.5 (3)

O1—S1—C1—C2	−15.8 (2)	C6—C1—C2—C3	2.2 (4)
O2—S1—C1—C2	−144.3 (2)	C1—C2—C3—C4	0.0 (4)
N1—S1—C1—C2	100.2 (2)	C2—C3—C4—N2	−179.4 (2)
O1—S1—C1—C6	162.6 (2)	C2—C3—C4—C5	−2.2 (4)
O2—S1—C1—C6	34.2 (3)	N2—C4—C5—C6	179.2 (3)
N1—S1—C1—C6	−81.5 (2)	C3—C4—C5—C6	2.1 (4)
C7—N2—C4—C3	−164.6 (2)	C4—C5—C6—C1	0.1 (5)
C7—N2—C4—C5	18.3 (4)	O3—C7—C8—C9	−16.5 (3)
C4—N2—C7—O3	2.2 (4)	N2—C7—C8—C9	165.7 (2)
C4—N2—C7—C8	180.0 (2)	C7—C8—C9—C10	176.7 (2)
S1—C1—C2—C3	−179.42 (18)	C8—C9—C10—C11	−177.1 (3)
S1—C1—C6—C5	179.3 (2)	C9—C10—C11—Cl1	−63.2 (3)
C2—C1—C6—C5	−2.2 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.93	2.25	2.809 (4)	118
N1—H1NA···O3ⁱ	0.87 (2)	1.99 (3)	2.865 (3)	176 (3)
N1—H1NB···O1ⁱⁱ	0.87 (3)	2.11 (2)	2.963 (3)	166 (4)
N2—H2N···O2ⁱⁱⁱ	0.88 (3)	2.17 (3)	3.021 (4)	166 (3)
C10—H10A···Cg1^iv	0.97	2.96	3.771 (3)	142

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅ClN₂O₃S
M_r	290.77
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.4872 (1), 8.7730 (2), 10.4572 (3)
α, β, γ (°)	73.711 (4), 85.281 (4), 63.393 (3)
V (Å³)	667.37 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.24 × 0.15 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.901, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	20164, 4036, 2815
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.169, 1.05
No. of reflections	4036
No. of parameters	172
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.35

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.93	2.25	2.809 (4)	118
N1—H1NA···O3ⁱ	0.87 (2)	1.99 (3)	2.865 (3)	176 (3)
N1—H1NB···O1ⁱⁱ	0.87 (3)	2.11 (2)	2.963 (3)	166 (4)
N2—H2N···O2ⁱⁱⁱ	0.88 (3)	2.17 (3)	3.021 (4)	166 (3)
C10—H10A···Cg1^iv	0.97	2.96	3.771 (3)	142

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

Acknowledgements

The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK Project Nos. 295 and 1136).

References

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Volume 68| Part 12| December 2012| Pages o3475-o3476

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