(RS)-2-Oxo-4-(1-phenyl­ethyl­amino)-1,2-dihydro­quinoline-3-carb­oxy­lic acid

Shishkina, S.V.; Ukrainets, I.V.; Mospanova, E.V.

doi:10.1107/S1600536811043297

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3054

doi:10.1107/S1600536811043297

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(RS)-2-Oxo-4-(1-phenylethylamino)-1,2-dihydroquinoline-3-carboxylic acid

Svitlana V. Shishkina,^a ^* Igor V. Ukrainets ^b and Elena V. Mospanova ^b

^aSTC `Institute for Single Crystals', National Academy of Sciences of Ukraine, 60 Lenina avenue, Kharkiv 61001, Ukraine, and ^bNational University of Pharmacy, 4 Blyukhera avenue, Kharkiv 61002, Ukraine
^*Correspondence e-mail: sveta@xray.isc.kharkov.com

(Received 14 September 2011; accepted 19 October 2011; online 29 October 2011)

The molecular structure of the title compound, C₁₈H₁₆N₂O₃, does not differ in the crystals of the racemic mixture, (I), and the pure enantiomer, (II). In their crystal structures, inversion dimers occur in (I) via N—H⋯O hydrogen bonds and infinite chains in (II) also via N—H⋯O hydrogen bonds.

Related literature

For the S and R enantiomers, see: Ukrainets et al. (2010 ). For bond lengths in related structures, see: Bürgi & Dunitz (1994 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₃
M_r = 308.33
Monoclinic, P 2₁ /n
a = 14.612 (2) Å
b = 5.9750 (6) Å
c = 18.014 (2) Å
β = 110.814 (14)°
V = 1470.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur 3 diffractometer
10943 measured reflections
2541 independent reflections
1174 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.033
S = 0.66
2541 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	1.038 (17)	1.794 (17)	2.8291 (15)	174.5 (14)
N2—H2N⋯O2	0.926 (14)	1.738 (14)	2.5849 (17)	150.4 (12)
O3—H3O⋯O1	0.943 (19)	1.59 (2)	2.4712 (15)	154.1 (18)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043297/jj2104sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043297/jj2104Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811043297/jj2104Isup3.cml

checkCIF report

Comment top

In the title compound, (I), the racemate of 2-oxo-4-(1-phenylethylamino)-1,2- dihydroquinoline-3-carboxylic acid reveals high analgesic activity. Compared to its pure S and R enantiomers, they are completely inactive (Ukrainets et al., 2010). In this paper we compare the molecular and crystal structure of the racemate (I) with a previously studied structure of the pure enantiomer (II). In the title compound (Fig. 1) the formation of two strong N2—H···O2 and O3—H···O1 intramolecular hydrogen bonds (Table 1) contributes to the coplanarity of the heterocycle, carboxyl, carbonyl groups and N2 atom all to be within 0.02 Å. As a result a significant redistribution of the electron density occurs in the quinolone fragment: the O3—C10 and C8—C9 bonds are shortened (Table 1) as compared with their mean values of 1.362 Å and 1.455 Å (Bürgi & Dunitz, 1994). The O1—C9, O2—C10, and C7—C8 bonds are elongated (mean values are 1.210 Å for a Csp²= O bond and 1.418 Å for a Csp²= Csp² bond). The substituent at the amino group has a sp- conformation. The C6—C7 bond (C11/N2/C7/C6 torsion angle = -1.6 (2)%A) is twisted slghtly allowing the methyl group to be ap- oriented relative to the C7—N2 bond (C7/N2/C11/C12 torsion angle = 171.3 (1)%A). The phenyl substituent is in a -sc-conformation relative to the C7—N2 bond and is twisted toward the N2—C11 bond (C7/N2/C11/C13 and N2/C11/C13/C18 torsion angles = -67.3 (2) %A and 36.3 (2) %A, respectively). The crystal structure of (I), therefore, differs significantly from that of (II). In the pure enantiomer (II) infinite chains (Fig. 2) result from the formation of an N1—H···O2 intermolecular hydrogen bond (Ukrainets et al., 2010). In the racemte, (I), centrosymmetric dimers (Fig. 3) are formed by a N1—H1N···O1 intermolecular hydrogen bond (Table 2). This allows for Cg1—Cg1 π—π stacking interactions to be observed [centroid–centroid distance = 3.894 (1)Åⁱ; i = 1-x, 2-y, -z; Cg1 = N1/C1/C6-C9].

Related literature top

For the pure S and R enantiomers, see: Ukrainets et al. (2010). For related bond lengths, see: Bürgi & Dunitz (1994).

Experimental top

2-Oxo-4-(1-phenylethylamino)-1,2-dihydroquinoline-3-carboxylic acid was synthesized using the published method (Ukrainets et al., 2010). Yield 75%. M.p. 225–227° C.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2005); cell refinement: CrysAlis PRO (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound with atomic numbering. All atoms are shown with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The packing of the pure enantiomer (II) in crystal phase. Hydrogen bonds are shown by dashed lines.
	Fig. 3. The packing of the title racemate (I) in crystal phase. Hydrogen bonds are shown by dashed lines.

(RS)-2-Oxo-4-(1-phenylethylamino)-1,2-dihydroquinoline-3-carboxylic acid top

Crystal data top

C₁₈H₁₆N₂O₃	F(000) = 648
M_r = 308.33	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 498–500 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.612 (2) Å	Cell parameters from 1534 reflections
b = 5.9750 (6) Å	θ = 3.0–32.0°
c = 18.014 (2) Å	µ = 0.10 mm⁻¹
β = 110.814 (14)°	T = 293 K
V = 1470.0 (3) Å³	Needle, colourless
Z = 4	0.30 × 0.10 × 0.05 mm

Data collection top

Oxford Diffraction Xcalibur 3 diffractometer	1174 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.068
Graphite monochromator	θ_max = 25.0°, θ_min = 3.0°
Detector resolution: 16.1827 pixels mm^-1	h = −17→17
ω scans	k = −7→7
10943 measured reflections	l = −20→21
2541 independent 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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F²) = 0.033	H atoms treated by a mixture of independent and constrained refinement
S = 0.66	w = 1/[σ²(F_o²) + (0.0067P)²] where P = (F_o² + 2F_c²)/3
2541 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.10 e Å⁻³
0 restraints	Δρ_min = −0.10 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₃	V = 1470.0 (3) Å³
M_r = 308.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.612 (2) Å	µ = 0.10 mm⁻¹
b = 5.9750 (6) Å	T = 293 K
c = 18.014 (2) Å	0.30 × 0.10 × 0.05 mm
β = 110.814 (14)°

Data collection top

Oxford Diffraction Xcalibur 3 diffractometer	1174 reflections with I > 2σ(I)
10943 measured reflections	R_int = 0.068
2541 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.033	H atoms treated by a mixture of independent and constrained refinement
S = 0.66	Δρ_max = 0.10 e Å⁻³
2541 reflections	Δρ_min = −0.10 e Å⁻³
221 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
N1	0.54636 (9)	0.7456 (2)	−0.03766 (8)	0.0393 (3)
H1N	0.4891 (13)	0.631 (2)	−0.0545 (9)	0.116 (7)*
N2	0.77647 (10)	1.19200 (19)	0.02901 (9)	0.0456 (4)
H2N	0.8164 (9)	1.153 (2)	0.0800 (9)	0.058 (5)*
O1	0.61318 (7)	0.55549 (16)	0.07595 (6)	0.0498 (3)
O2	0.84379 (7)	0.97876 (16)	0.16236 (6)	0.0615 (3)
O3	0.76182 (8)	0.6926 (2)	0.18244 (7)	0.0613 (4)
H3O	0.7056 (15)	0.610 (3)	0.1530 (12)	0.138 (9)*
C1	0.54064 (10)	0.9229 (2)	−0.08811 (8)	0.0350 (4)
C2	0.45947 (10)	0.9355 (2)	−0.15744 (9)	0.0447 (4)
H2	0.4131	0.8214	−0.1703	0.054*
C3	0.44735 (11)	1.1146 (2)	−0.20685 (9)	0.0485 (4)
H3	0.3921	1.1251	−0.2527	0.058*
C4	0.51788 (11)	1.2804 (2)	−0.18817 (9)	0.0490 (4)
H4	0.5097	1.4034	−0.2216	0.059*
C5	0.59936 (10)	1.2656 (2)	−0.12129 (9)	0.0448 (4)
H5	0.6463	1.3781	−0.1104	0.054*
C6	0.61435 (10)	1.0856 (2)	−0.06863 (8)	0.0340 (4)
C7	0.69759 (10)	1.0588 (2)	0.00556 (8)	0.0344 (4)
C8	0.69570 (10)	0.8825 (2)	0.05766 (9)	0.0351 (4)
C9	0.61762 (11)	0.7222 (2)	0.03378 (10)	0.0378 (4)
C10	0.77197 (12)	0.8569 (3)	0.13643 (10)	0.0472 (4)
C11	0.80766 (10)	1.3854 (2)	−0.00571 (9)	0.0424 (4)
H11	0.7558	1.4987	−0.0191	0.051*
C12	0.89830 (10)	1.4790 (2)	0.05891 (8)	0.0595 (5)
H12C	0.9503	1.3712	0.0714	0.089*
H12B	0.8833	1.5102	0.1056	0.089*
H12A	0.9183	1.6145	0.0404	0.089*
C13	0.83092 (10)	1.3343 (2)	−0.07889 (9)	0.0379 (4)
C14	0.81570 (10)	1.4954 (2)	−0.13665 (10)	0.0498 (4)
H14	0.7851	1.6288	−0.1324	0.060*
C15	0.84497 (12)	1.4625 (3)	−0.20070 (10)	0.0609 (5)
H15	0.8341	1.5733	−0.2392	0.073*
C16	0.88995 (12)	1.2670 (3)	−0.20764 (11)	0.0664 (5)
H16	0.9103	1.2443	−0.2504	0.080*
C17	0.90463 (12)	1.1050 (3)	−0.15065 (12)	0.0642 (5)
H17	0.9351	0.9718	−0.1552	0.077*
C18	0.87513 (11)	1.1362 (2)	−0.08708 (10)	0.0513 (4)
H18	0.8849	1.0236	−0.0494	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0343 (8)	0.0428 (8)	0.0359 (10)	−0.0088 (7)	0.0063 (7)	0.0011 (6)
N2	0.0365 (9)	0.0539 (9)	0.0423 (11)	−0.0131 (7)	0.0091 (8)	0.0010 (7)
O1	0.0443 (7)	0.0459 (6)	0.0516 (8)	−0.0080 (5)	0.0075 (6)	0.0116 (6)
O2	0.0469 (8)	0.0690 (7)	0.0517 (8)	−0.0163 (6)	−0.0031 (6)	0.0055 (6)
O3	0.0458 (8)	0.0709 (8)	0.0538 (10)	−0.0083 (7)	0.0011 (7)	0.0206 (7)
C1	0.0342 (10)	0.0403 (10)	0.0311 (11)	−0.0008 (8)	0.0122 (8)	−0.0026 (8)
C2	0.0367 (11)	0.0486 (10)	0.0443 (12)	−0.0072 (7)	0.0090 (9)	−0.0016 (8)
C3	0.0385 (10)	0.0665 (11)	0.0356 (12)	−0.0035 (9)	0.0071 (8)	0.0007 (9)
C4	0.0402 (10)	0.0580 (11)	0.0468 (13)	0.0002 (9)	0.0133 (9)	0.0142 (8)
C5	0.0330 (10)	0.0503 (10)	0.0497 (13)	−0.0089 (8)	0.0132 (9)	0.0036 (8)
C6	0.0306 (9)	0.0414 (10)	0.0305 (11)	−0.0022 (8)	0.0113 (8)	−0.0044 (7)
C7	0.0276 (10)	0.0399 (9)	0.0373 (11)	−0.0021 (8)	0.0135 (8)	−0.0065 (8)
C8	0.0259 (9)	0.0428 (10)	0.0334 (11)	−0.0028 (7)	0.0066 (8)	−0.0019 (8)
C9	0.0356 (10)	0.0367 (10)	0.0415 (12)	0.0008 (8)	0.0143 (9)	−0.0011 (8)
C10	0.0426 (12)	0.0479 (12)	0.0490 (13)	−0.0006 (9)	0.0137 (10)	0.0017 (9)
C11	0.0357 (10)	0.0423 (9)	0.0499 (12)	−0.0100 (8)	0.0163 (9)	−0.0049 (8)
C12	0.0563 (11)	0.0621 (11)	0.0569 (13)	−0.0238 (9)	0.0161 (9)	−0.0139 (9)
C13	0.0334 (10)	0.0371 (10)	0.0440 (12)	−0.0090 (7)	0.0145 (8)	−0.0046 (8)
C14	0.0458 (11)	0.0454 (11)	0.0590 (13)	−0.0042 (7)	0.0195 (10)	−0.0003 (9)
C15	0.0609 (13)	0.0689 (13)	0.0548 (14)	−0.0091 (10)	0.0230 (10)	0.0084 (10)
C16	0.0680 (14)	0.0798 (15)	0.0593 (14)	−0.0109 (11)	0.0323 (11)	−0.0136 (11)
C17	0.0672 (13)	0.0517 (11)	0.0828 (16)	0.0006 (9)	0.0377 (12)	−0.0127 (11)
C18	0.0563 (12)	0.0433 (11)	0.0597 (13)	−0.0006 (9)	0.0273 (10)	0.0019 (9)

Geometric parameters (Å, º) top

N1—C9	1.3444 (17)	C7—C8	1.4177 (16)
N1—C1	1.3788 (16)	C8—C9	1.4334 (17)
N1—H1N	1.038 (17)	C8—C10	1.4679 (18)
N2—C7	1.3395 (15)	C11—C13	1.5051 (17)
N2—C11	1.4619 (16)	C11—C12	1.5251 (16)
N2—H2N	0.926 (14)	C11—H11	0.9800
O1—C9	1.2684 (15)	C12—H12C	0.9600
O2—C10	1.2252 (15)	C12—H12B	0.9600
O3—C10	1.3268 (17)	C12—H12A	0.9600
O3—H3O	0.943 (19)	C13—C14	1.3760 (16)
C1—C2	1.3854 (16)	C13—C18	1.3812 (16)
C1—C6	1.4000 (15)	C14—C15	1.3796 (19)
C2—C3	1.3626 (16)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.3675 (19)
C3—C4	1.3825 (17)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.3712 (19)
C4—C5	1.3629 (19)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.3721 (19)
C5—C6	1.3986 (17)	C17—H17	0.9300
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.4614 (17)

C9—N1—C1	123.76 (14)	O2—C10—O3	118.18 (16)
C9—N1—H1N	118.7 (9)	O2—C10—C8	124.05 (15)
C1—N1—H1N	117.3 (8)	O3—C10—C8	117.77 (14)
C7—N2—C11	134.34 (14)	N2—C11—C13	114.59 (12)
C7—N2—H2N	109.4 (8)	N2—C11—C12	106.35 (12)
C11—N2—H2N	116.2 (8)	C13—C11—C12	109.74 (12)
C10—O3—H3O	107.6 (12)	N2—C11—H11	108.7
N1—C1—C2	117.90 (14)	C13—C11—H11	108.7
N1—C1—C6	120.48 (14)	C12—C11—H11	108.7
C2—C1—C6	121.61 (14)	C11—C12—H12C	109.5
C3—C2—C1	120.16 (14)	C11—C12—H12B	109.5
C3—C2—H2	119.9	H12C—C12—H12B	109.5
C1—C2—H2	119.9	C11—C12—H12A	109.5
C2—C3—C4	119.44 (15)	H12C—C12—H12A	109.5
C2—C3—H3	120.3	H12B—C12—H12A	109.5
C4—C3—H3	120.3	C14—C13—C18	118.34 (14)
C5—C4—C3	120.65 (14)	C14—C13—C11	119.62 (14)
C5—C4—H4	119.7	C18—C13—C11	121.81 (14)
C3—C4—H4	119.7	C13—C14—C15	121.19 (15)
C4—C5—C6	121.79 (14)	C13—C14—H14	119.4
C4—C5—H5	119.1	C15—C14—H14	119.4
C6—C5—H5	119.1	C16—C15—C14	120.00 (16)
C5—C6—C1	116.28 (13)	C16—C15—H15	120.0
C5—C6—C7	125.69 (14)	C14—C15—H15	120.0
C1—C6—C7	117.98 (13)	C15—C16—C17	119.13 (17)
N2—C7—C8	116.72 (13)	C15—C16—H16	120.4
N2—C7—C6	124.51 (14)	C17—C16—H16	120.4
C8—C7—C6	118.77 (13)	C16—C17—C18	121.14 (16)
C7—C8—C9	119.89 (14)	C16—C17—H17	119.4
C7—C8—C10	122.05 (14)	C18—C17—H17	119.4
C9—C8—C10	118.06 (14)	C17—C18—C13	120.19 (14)
O1—C9—N1	117.89 (13)	C17—C18—H18	119.9
O1—C9—C8	123.34 (15)	C13—C18—H18	119.9
N1—C9—C8	118.75 (15)

C9—N1—C1—C2	−175.26 (14)	C1—N1—C9—C8	−3.8 (2)
C9—N1—C1—C6	3.8 (2)	C7—C8—C9—O1	177.18 (13)
N1—C1—C2—C3	175.92 (13)	C10—C8—C9—O1	−2.7 (2)
C6—C1—C2—C3	−3.2 (2)	C7—C8—C9—N1	−1.2 (2)
C1—C2—C3—C4	1.6 (2)	C10—C8—C9—N1	178.91 (13)
C2—C3—C4—C5	0.4 (2)	C7—C8—C10—O2	−2.3 (2)
C3—C4—C5—C6	−0.9 (2)	C9—C8—C10—O2	177.57 (14)
C4—C5—C6—C1	−0.5 (2)	C7—C8—C10—O3	177.13 (13)
C4—C5—C6—C7	−177.97 (14)	C9—C8—C10—O3	−3.0 (2)
N1—C1—C6—C5	−176.49 (13)	C7—N2—C11—C13	−67.3 (2)
C2—C1—C6—C5	2.57 (19)	C7—N2—C11—C12	171.26 (14)
N1—C1—C6—C7	1.15 (19)	N2—C11—C13—C14	149.27 (13)
C2—C1—C6—C7	−179.79 (13)	C12—C11—C13—C14	−91.19 (15)
C11—N2—C7—C8	179.24 (15)	N2—C11—C13—C18	−36.34 (18)
C11—N2—C7—C6	−1.6 (2)	C12—C11—C13—C18	83.21 (15)
C5—C6—C7—N2	−7.6 (2)	C18—C13—C14—C15	−1.0 (2)
C1—C6—C7—N2	175.04 (13)	C11—C13—C14—C15	173.62 (14)
C5—C6—C7—C8	171.59 (13)	C13—C14—C15—C16	0.0 (2)
C1—C6—C7—C8	−5.81 (18)	C14—C15—C16—C17	0.5 (2)
N2—C7—C8—C9	−174.91 (12)	C15—C16—C17—C18	−0.1 (3)
C6—C7—C8—C9	5.87 (19)	C16—C17—C18—C13	−0.8 (3)
N2—C7—C8—C10	4.98 (19)	C14—C13—C18—C17	1.4 (2)
C6—C7—C8—C10	−174.23 (13)	C11—C13—C18—C17	−173.10 (15)
C1—N1—C9—O1	177.72 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	1.038 (17)	1.794 (17)	2.8291 (15)	174.5 (14)
N2—H2N···O2	0.926 (14)	1.738 (14)	2.5849 (17)	150.4 (12)
O3—H3O···O1	0.943 (19)	1.59 (2)	2.4712 (15)	154.1 (18)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₃
M_r	308.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.612 (2), 5.9750 (6), 18.014 (2)
β (°)	110.814 (14)
V (Å³)	1470.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur 3 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10943, 2541, 1174
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.033, 0.66
No. of reflections	2541
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.10

Computer programs: CrysAlis PRO (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

O1—C9	1.2684 (15)	C7—C8	1.4177 (16)
O2—C10	1.2252 (15)	C8—C9	1.4334 (17)
O3—C10	1.3268 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	1.038 (17)	1.794 (17)	2.8291 (15)	174.5 (14)
N2—H2N···O2	0.926 (14)	1.738 (14)	2.5849 (17)	150.4 (12)
O3—H3O···O1	0.943 (19)	1.59 (2)	2.4712 (15)	154.1 (18)

Symmetry code: (i) −x+1, −y+1, −z.

References

Bürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767–784. Weinheim: VCH. Google Scholar
Oxford Diffraction (2005). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ukrainets, I. V., Mospanova, E. V., Davidenko, A. A. & Shishkina, S. V. (2010). Khim. Geterotsikl. Soedin. pp. 1690–1701. Google Scholar

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Volume 67| Part 11| November 2011| Page o3054

doi:10.1107/S1600536811043297

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