N-(2-Benzoyl-4-chloro­phen­yl)-4-chloro­benzene­sulfonamide

Valkonen, A.; Gawinecki, R.; Janota, H.; Ośmiałowski, B.; Kolehmainen, E.

doi:10.1107/S1600536808007435

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o737

doi:10.1107/S1600536808007435

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N-(2-Benzoyl-4-chlorophenyl)-4-chlorobenzenesulfonamide

Arto Valkonen,^a ^* Ryszard Gawinecki,^b Henryk Janota,^b Borys Ośmiałowski ^b and Erkki Kolehmainen ^a

^aDepartment of Chemistry, University of Jyväskylä, PO Box 35, FIN-40014 Jyväskylä, Finland, and ^bDepartment of Chemistry, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland
^*Correspondence e-mail: arto.valkonen@jyu.fi

(Received 28 February 2008; accepted 18 March 2008; online 29 March 2008)

The title compound, C₁₉H₁₃Cl₂NO₃S, is an N-arylsulfonyl derivative of 2-amino-5-chlorobenzophenone. The compound is biologically active and shows potential to be utilized as an inhibitor of CCR2 and CCR9 receptor functions. In the crystal structure, there is an intramolecular N—H⋯O hydrogen bond between the amide and carbonyl groups. The benzoyl and 4-chlorophenyl groups form intramolecular and intermolecular face-to-face contacts, with a dihedral angle of 10.6 (1)° between their mean planes in both cases, and centroid–centroid separations of 4.00 (1) and 4.25 (1) Å for the intra- and intermolecular interactions, respectively.

Related literature

For related literature, see: Basak et al. (2008 ); Fleming et al. (2003 ); Kolehmainen et al. (2003 ); Sternbach et al. (1962 ).

Experimental

Crystal data

C₁₉H₁₃Cl₂NO₃S
M_r = 406.26
Monoclinic, P 2₁ /n
a = 8.2307 (1) Å
b = 18.5014 (3) Å
c = 12.1364 (2) Å
β = 105.211 (1)°
V = 1783.38 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 173 (2) K
0.25 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: none
13987 measured reflections
4401 independent reflections
3534 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.084
S = 1.05
4401 reflections
238 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.865 (15)	2.20 (2)	2.798 (2)	126.1 (18)

Data collection: COLLECT (Bruker, 2004 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ) and Mercury (Macrae et al., 2006 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007435/bi2286sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007435/bi2286Isup2.hkl

checkCIF report

Comment top

The title compound was originally prepared to study its molecular structure by spectroscopy (Kolehmainen et al., 2003). The compound has a sulfone group showing strong electron acceptor capability and two S=O double bonds with ineffective conjugation properties with other double bonds. The compound has also shown a potential to be utilized as inhibitor of CCR2 (Basak et al., 2008) and CCR9 (Fleming et al., 2003) receptor functions. This potent antagonist can possibly be utilized in pharmaceutical compositions for treatment of CCR2 and CCR9 related diseases.

In the crystal, there is an intramolecular N—H···O hydrogen bond between the amide and carbonyl groups (Fig. 1). The benzoyl and 4-chlorophenyl groups form intramolecular (Fig. 2) and intermolecular face-to-face contacts (Fig. 3), with a dihedral angle of 10.6 (1)° between their mean planes in both cases, and a centroid-centroid separation of 4.00 (1) and 4.25 (1)Å for the intra- and intermolecular interactions, respectively.

Related literature top

For related literature, see: Basak et al. (2008); Fleming et al. (2003); Kolehmainen et al. (2003); Sternbach et al. (1962).

Experimental top

The title compound was obtained by condensation of 2-amino-5-chlorobenzophenone and 4-chlorobenzenesulfonyl chloride according to a previously described method (Sternbach et al., 1962). The reaction product was purified by crystallization from ethanol. The spectroscopic characterization (NMR, IR) has previously been reported by us (Kolehmainen et al., 2003). The single-crystal suitable for X-ray determination was obtained by extremely slow evaporation of a CDCl₃ solution in a NMR tube.

Computing details top

Data collection: COLLECT (Bruker, 2004); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented by circles of arbitrary size
	Fig. 2. Molecular conformation with selected geometric parameters
	Fig. 3. Packing viewed along the a-axis showing the stack-like architecture

N-(2-Benzoyl-4-chlorophenyl)-4-chlorobenzenesulfonamide top

Crystal data top

C₁₉H₁₃Cl₂NO₃S	F(000) = 832
M_r = 406.26	D_x = 1.513 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 31954 reflections
a = 8.2307 (1) Å	θ = 0.4–28.3°
b = 18.5014 (3) Å	µ = 0.50 mm⁻¹
c = 12.1364 (2) Å	T = 173 K
β = 105.211 (1)°	Block, yellow
V = 1783.38 (5) Å³	0.25 × 0.25 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3534 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 28.3°, θ_min = 2.1°
ϕ and ω scans	h = −10→10
13987 measured reflections	k = −24→24
4401 independent reflections	l = −14→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0187P)² + 1.5712P] where P = (F_o² + 2F_c²)/3
4401 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₉H₁₃Cl₂NO₃S	V = 1783.38 (5) Å³
M_r = 406.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2307 (1) Å	µ = 0.50 mm⁻¹
b = 18.5014 (3) Å	T = 173 K
c = 12.1364 (2) Å	0.25 × 0.25 × 0.15 mm
β = 105.211 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3534 reflections with I > 2σ(I)
13987 measured reflections	R_int = 0.044
4401 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.32 e Å⁻³
4401 reflections	Δρ_min = −0.31 e Å⁻³
238 parameters

Special details top

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
Cl1	0.44574 (7)	0.01345 (3)	0.80411 (4)	0.03185 (13)
S1	0.95358 (6)	0.13899 (3)	0.46317 (4)	0.02381 (11)
Cl2	0.64457 (7)	0.44781 (3)	0.45821 (5)	0.03514 (13)
O1	0.47941 (18)	0.13671 (8)	0.33815 (11)	0.0301 (3)
O3	1.00797 (18)	0.13033 (8)	0.36105 (13)	0.0331 (3)
O2	1.06708 (17)	0.12706 (8)	0.57308 (12)	0.0310 (3)
N1	0.7971 (2)	0.08200 (9)	0.44914 (14)	0.0239 (3)
H1	0.729 (2)	0.0856 (12)	0.3815 (14)	0.029*
C4	0.7144 (3)	0.01218 (10)	0.71469 (17)	0.0270 (4)
H4	0.7690	−0.0164	0.7787	0.032*
C15	0.7816 (2)	0.25730 (11)	0.35920 (17)	0.0261 (4)
H15	0.7689	0.2312	0.2900	0.031*
C7	0.4749 (2)	0.15092 (10)	0.43573 (16)	0.0220 (4)
C6	0.4742 (2)	0.08317 (10)	0.61488 (16)	0.0231 (4)
H6	0.3652	0.1018	0.6107	0.028*
C1	0.5564 (2)	0.10128 (10)	0.53194 (16)	0.0215 (4)
C14	0.8692 (2)	0.22691 (10)	0.46257 (16)	0.0227 (4)
C10	0.2063 (3)	0.31757 (12)	0.3887 (2)	0.0358 (5)
H10	0.1250	0.3397	0.3278	0.043*
C17	0.7328 (2)	0.36241 (10)	0.45946 (17)	0.0246 (4)
C18	0.8210 (3)	0.33297 (11)	0.56290 (17)	0.0279 (4)
H18	0.8345	0.3594	0.6318	0.033*
C16	0.7129 (3)	0.32578 (11)	0.35766 (17)	0.0268 (4)
H16	0.6530	0.3472	0.2876	0.032*
C2	0.7158 (2)	0.07170 (10)	0.53854 (16)	0.0220 (4)
C8	0.3942 (2)	0.21889 (10)	0.46066 (16)	0.0222 (4)
C19	0.8891 (2)	0.26433 (11)	0.56418 (17)	0.0261 (4)
H19	0.9491	0.2431	0.6343	0.031*
C9	0.2776 (3)	0.25261 (11)	0.37109 (17)	0.0280 (4)
H9	0.2473	0.2307	0.2977	0.034*
C3	0.7952 (2)	0.02892 (10)	0.63138 (17)	0.0262 (4)
H3	0.9055	0.0111	0.6376	0.031*
C5	0.5527 (2)	0.03774 (10)	0.70344 (16)	0.0232 (4)
C13	0.4391 (3)	0.25198 (11)	0.56727 (17)	0.0266 (4)
H13	0.5174	0.2291	0.6290	0.032*
C11	0.2525 (3)	0.35055 (11)	0.4944 (2)	0.0362 (5)
H11	0.2036	0.3955	0.5058	0.043*
C12	0.3699 (3)	0.31836 (11)	0.58384 (19)	0.0334 (5)
H12	0.4030	0.3415	0.6562	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0399 (3)	0.0286 (3)	0.0302 (3)	−0.0016 (2)	0.0148 (2)	0.0021 (2)
S1	0.0222 (2)	0.0227 (2)	0.0275 (3)	0.00388 (18)	0.00828 (19)	0.00123 (19)
Cl2	0.0431 (3)	0.0224 (2)	0.0419 (3)	0.0072 (2)	0.0147 (2)	−0.0016 (2)
O1	0.0341 (8)	0.0324 (8)	0.0215 (7)	0.0044 (6)	0.0029 (6)	−0.0029 (6)
O3	0.0374 (8)	0.0304 (8)	0.0375 (8)	0.0066 (6)	0.0202 (7)	0.0006 (6)
O2	0.0221 (7)	0.0336 (8)	0.0349 (8)	0.0041 (6)	0.0031 (6)	0.0044 (6)
N1	0.0255 (8)	0.0219 (8)	0.0239 (9)	−0.0003 (7)	0.0058 (7)	−0.0030 (7)
C4	0.0304 (10)	0.0195 (9)	0.0283 (10)	0.0012 (8)	0.0029 (8)	0.0045 (8)
C15	0.0321 (11)	0.0250 (10)	0.0210 (10)	0.0016 (8)	0.0064 (8)	−0.0016 (8)
C7	0.0191 (9)	0.0223 (9)	0.0229 (10)	−0.0021 (7)	0.0024 (7)	−0.0010 (7)
C6	0.0217 (9)	0.0202 (9)	0.0267 (10)	0.0005 (7)	0.0050 (8)	−0.0016 (8)
C1	0.0227 (9)	0.0169 (9)	0.0223 (9)	−0.0004 (7)	0.0013 (7)	−0.0017 (7)
C14	0.0226 (9)	0.0223 (9)	0.0243 (10)	0.0010 (7)	0.0079 (8)	0.0013 (7)
C10	0.0364 (12)	0.0279 (11)	0.0399 (13)	0.0081 (9)	0.0042 (10)	0.0105 (10)
C17	0.0255 (10)	0.0184 (9)	0.0312 (11)	0.0003 (7)	0.0099 (8)	−0.0014 (8)
C18	0.0327 (11)	0.0268 (10)	0.0242 (10)	−0.0010 (8)	0.0075 (8)	−0.0051 (8)
C16	0.0299 (10)	0.0258 (10)	0.0234 (10)	0.0030 (8)	0.0047 (8)	0.0017 (8)
C2	0.0243 (9)	0.0179 (9)	0.0232 (9)	0.0003 (7)	0.0051 (7)	−0.0014 (7)
C8	0.0201 (9)	0.0205 (9)	0.0255 (10)	−0.0004 (7)	0.0051 (7)	0.0038 (7)
C19	0.0265 (10)	0.0276 (10)	0.0222 (10)	−0.0007 (8)	0.0031 (8)	0.0004 (8)
C9	0.0309 (11)	0.0253 (10)	0.0251 (10)	0.0009 (8)	0.0027 (8)	0.0052 (8)
C3	0.0235 (10)	0.0200 (9)	0.0336 (11)	0.0025 (7)	0.0046 (8)	0.0010 (8)
C5	0.0292 (10)	0.0181 (9)	0.0223 (9)	−0.0034 (8)	0.0067 (8)	−0.0016 (7)
C13	0.0303 (10)	0.0253 (10)	0.0230 (10)	−0.0003 (8)	0.0051 (8)	0.0017 (8)
C11	0.0416 (13)	0.0198 (10)	0.0519 (14)	0.0049 (9)	0.0205 (11)	0.0053 (10)
C12	0.0439 (13)	0.0251 (10)	0.0350 (12)	−0.0047 (9)	0.0168 (10)	−0.0043 (9)

Geometric parameters (Å, º) top

Cl1—C5	1.742 (2)	C14—C19	1.386 (3)
S1—O2	1.4307 (15)	C10—C9	1.379 (3)
S1—O3	1.4329 (15)	C10—C11	1.381 (3)
S1—N1	1.6383 (17)	C10—H10	0.950
S1—C14	1.7679 (19)	C17—C16	1.381 (3)
Cl2—C17	1.7374 (19)	C17—C18	1.386 (3)
O1—C7	1.223 (2)	C18—C19	1.387 (3)
N1—C2	1.429 (2)	C18—H18	0.950
N1—H1	0.865 (15)	C16—H16	0.950
C4—C3	1.384 (3)	C2—C3	1.392 (3)
C4—C5	1.385 (3)	C8—C13	1.391 (3)
C4—H4	0.950	C8—C9	1.394 (3)
C15—C16	1.386 (3)	C19—H19	0.950
C15—C14	1.391 (3)	C9—H9	0.950
C15—H15	0.950	C3—H3	0.950
C7—C8	1.490 (3)	C13—C12	1.391 (3)
C7—C1	1.499 (3)	C13—H13	0.950
C6—C5	1.384 (3)	C11—C12	1.384 (3)
C6—C1	1.393 (3)	C11—H11	0.950
C6—H6	0.950	C12—H12	0.950
C1—C2	1.404 (3)

O2—S1—O3	120.89 (9)	C17—C18—C19	118.95 (18)
O2—S1—N1	107.51 (9)	C17—C18—H18	120.5
O3—S1—N1	104.68 (9)	C19—C18—H18	120.5
O2—S1—C14	107.79 (9)	C17—C16—C15	118.98 (18)
O3—S1—C14	108.11 (9)	C17—C16—H16	120.5
N1—S1—C14	107.13 (9)	C15—C16—H16	120.5
C2—N1—S1	121.25 (13)	C3—C2—C1	120.09 (18)
C2—N1—H1	114.7 (15)	C3—C2—N1	118.44 (17)
S1—N1—H1	110.0 (15)	C1—C2—N1	121.43 (17)
C3—C4—C5	119.05 (18)	C13—C8—C9	119.28 (18)
C3—C4—H4	120.5	C13—C8—C7	122.45 (17)
C5—C4—H4	120.5	C9—C8—C7	118.12 (17)
C16—C15—C14	119.66 (18)	C14—C19—C18	119.64 (18)
C16—C15—H15	120.2	C14—C19—H19	120.2
C14—C15—H15	120.2	C18—C19—H19	120.2
O1—C7—C8	120.44 (17)	C10—C9—C8	120.21 (19)
O1—C7—C1	120.10 (17)	C10—C9—H9	119.9
C8—C7—C1	119.43 (16)	C8—C9—H9	119.9
C5—C6—C1	119.39 (17)	C4—C3—C2	120.33 (18)
C5—C6—H6	120.3	C4—C3—H3	119.8
C1—C6—H6	120.3	C2—C3—H3	119.8
C6—C1—C2	119.26 (17)	C6—C5—C4	121.67 (18)
C6—C1—C7	120.47 (17)	C6—C5—Cl1	118.85 (15)
C2—C1—C7	120.26 (17)	C4—C5—Cl1	119.48 (15)
C19—C14—C15	120.85 (18)	C12—C13—C8	120.28 (19)
C19—C14—S1	120.09 (15)	C12—C13—H13	119.9
C15—C14—S1	119.06 (15)	C8—C13—H13	119.9
C9—C10—C11	120.3 (2)	C10—C11—C12	120.3 (2)
C9—C10—H10	119.9	C10—C11—H11	119.9
C11—C10—H10	119.9	C12—C11—H11	119.9
C16—C17—C18	121.92 (18)	C11—C12—C13	119.7 (2)
C16—C17—Cl2	119.17 (15)	C11—C12—H12	120.2
C18—C17—Cl2	118.92 (15)	C13—C12—H12	120.2

O2—S1—N1—C2	46.32 (17)	C7—C1—C2—N1	−6.2 (3)
O3—S1—N1—C2	176.05 (14)	S1—N1—C2—C3	−78.1 (2)
C14—S1—N1—C2	−69.30 (16)	S1—N1—C2—C1	104.42 (19)
C5—C6—C1—C2	1.4 (3)	O1—C7—C8—C13	−154.24 (19)
C5—C6—C1—C7	−179.43 (17)	C1—C7—C8—C13	23.5 (3)
O1—C7—C1—C6	−136.12 (19)	O1—C7—C8—C9	21.4 (3)
C8—C7—C1—C6	46.2 (2)	C1—C7—C8—C9	−160.91 (17)
O1—C7—C1—C2	43.0 (3)	C15—C14—C19—C18	0.0 (3)
C8—C7—C1—C2	−134.72 (18)	S1—C14—C19—C18	−179.36 (15)
C16—C15—C14—C19	−0.2 (3)	C17—C18—C19—C14	0.6 (3)
C16—C15—C14—S1	179.15 (15)	C11—C10—C9—C8	1.5 (3)
O2—S1—C14—C19	−13.39 (18)	C13—C8—C9—C10	−0.8 (3)
O3—S1—C14—C19	−145.63 (16)	C7—C8—C9—C10	−176.61 (19)
N1—S1—C14—C19	102.04 (17)	C5—C4—C3—C2	0.9 (3)
O2—S1—C14—C15	167.28 (15)	C1—C2—C3—C4	3.3 (3)
O3—S1—C14—C15	35.04 (18)	N1—C2—C3—C4	−174.15 (17)
N1—S1—C14—C15	−77.28 (17)	C1—C6—C5—C4	2.9 (3)
C16—C17—C18—C19	−0.9 (3)	C1—C6—C5—Cl1	−178.11 (14)
Cl2—C17—C18—C19	178.95 (15)	C3—C4—C5—C6	−4.0 (3)
C18—C17—C16—C15	0.7 (3)	C3—C4—C5—Cl1	176.93 (15)
Cl2—C17—C16—C15	−179.17 (15)	C9—C8—C13—C12	−0.7 (3)
C14—C15—C16—C17	−0.1 (3)	C7—C8—C13—C12	174.83 (18)
C6—C1—C2—C3	−4.5 (3)	C9—C10—C11—C12	−0.5 (3)
C7—C1—C2—C3	176.37 (17)	C10—C11—C12—C13	−1.1 (3)
C6—C1—C2—N1	172.92 (17)	C8—C13—C12—C11	1.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.87 (2)	2.97 (2)	3.6519 (17)	138 (2)
N1—H1···O1	0.87 (2)	2.20 (2)	2.798 (2)	126 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃Cl₂NO₃S
M_r	406.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	8.2307 (1), 18.5014 (3), 12.1364 (2)
β (°)	105.211 (1)
V (Å³)	1783.38 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.25 × 0.25 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13987, 4401, 3534
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.084, 1.05
No. of reflections	4401
No. of parameters	238
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.31

Computer programs: COLLECT (Bruker, 2004), DENZO-SMN (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.865 (15)	2.20 (2)	2.798 (2)	126.1 (18)

References

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Volume 64| Part 4| April 2008| Page o737

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