(4R*,5R*)-2-(4-Meth­oxy­phen­yl)-1,3-dioxolane-4,5-dicarboxamide

Lv, C.-L.; Chen, J.-H.; Zhang, Y.-Z.; Lu, D.-Q.; OuYang, P.-K.

doi:10.1107/S1600536812002401

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o558

doi:10.1107/S1600536812002401

Open

access

(4R,5R)-2-(4-Methoxyphenyl)-1,3-dioxolane-4,5-dicarboxamide

Chun-Lei Lv,^a,^c,^b Jian-Hui Chen,^b Yu-Zhe Zhang,^a,^b Ding-Qiang Lu ^a ^* and Ping-Kai OuYang ^a

^aSchool of Pharmaceutical Science, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, ^bXinchang Pharmaceutical Factory, Zhejiang Medicine Co. Ltd, Xinchang 312500, People's Republic of China, and ^cCollege of Materials Science and, Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: ludingqiang@126.com

(Received 9 January 2012; accepted 19 January 2012; online 4 February 2012)

In the title compound, C₁₂H₁₄N₂O₅, the five-membered 1,3-dioxolane ring has a twisted conformation. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a two-dimensional network lying parallel to the ab plane. There are also C—H⋯π interactions present in the crystal structure.

Related literature

For the importantce of (2S,3S)-diethyl-2,3-O-alkyltartrate analogues in the synthesis of platinum complexes with antitumor activity, see: Kim et al. (1994 ), and for their importance as intermediates in organic synthesis, see: Pandey et al. (1997 ). For the synthesis of the title compound, see: Ates-Alagoz & Buyukbingol (2001 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₄N₂O₅
M_r = 266.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9620 (14) Å
b = 10.727 (2) Å
c = 16.932 (3) Å
V = 1264.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.978, T_max = 0.989
2615 measured reflections
2297 independent reflections
1939 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.135
S = 1.00
2297 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.21	3.063 (3)	174
N1—H1B⋯O5ⁱⁱ	0.86	2.22	2.994 (4)	149
N2—H2A⋯O4ⁱⁱⁱ	0.86	2.13	2.984 (4)	169
C7—H7A⋯O4^iv	0.93	2.57	3.491 (4)	170
C9—H9A⋯Cg2^v	0.98	2.83	3.737 (3)	154
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x, y+1, z; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002401/su2367sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002401/su2367Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002401/su2367Isup3.cml

checkCIF report

Comment top

Antitumor platinum drugs are some of the most effective anticancer agents currently available. (2S,3S)-Diethyl-2,3-O-alkyltartrate analogues are starting materials for the synthesis of platinum complexes with antitumor activity (Kim et al., 1994), and are also important intermediates in organic synthesis (Pandey et al., 1997). As part of our studies of the synthesis and characterization of such compounds, we herein report on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are within normal ranges. The five-membered 1,3-dioxolane ring (O2,O3,C8-C10) has a twisted conformation on bond O2-C8.

In the crystal, intermolecular N—H···O and C—H···O hydrogen bonds link the molecules to form two-dimensional networks lieing parallel to the ab plane (Table 1 and Fig 2). There are also C-H···π interactions present in the crystal structure (Table 1).

Related literature top

For the importantce of (2S,3S)-diethyl-2,3-O-alkyltartrate analogues in the synthesis of platinum complexes with antitumor activity, see: Kim et al. (1994), and for their importance as intermediates in organic synthesis, see: Pandey et al. (1997). For the synthesis of the title compound, see: Ates-Alagoz & Buyukbingol (2001). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was synthesized according to the published procedure (Ates-Alagoz & Buyukbingol, 2001). A mixture of (2S,3S)-diethyltartrate (500 mg, 2.43 mmol), 4-methoxybenzaldehyde (331 mg, 2.43 mmol), anhydrous copper(II) sulfate (776 mg, 2.86 mmol), and one drop of methane sulfonic acid in anhydrous toluene (8 ml) was stirred at room temperature for 8 h. Anhydrous Magnesium sulfate (30 mg) was added to the reaction mixture, which was then stirred for a further 20 min. Then a colourless precipitate was obtained by evaporation and dried in vacuo (Yield 83%). The obtained colourless product (654 mg, 2 mmol) was dissolved in 40 ml anhydrous ethanol, then a current of dry ammonia (dried by calcium cholride) was passed into the reaction mixture at room temperature for 4 h. The reaction mixture was then filtered and the resulting product was evaporated to dryness. Pure compound was obtained by crystallization from ethanol. Block-like yellow crystals of the title compound, suitable for X-ray diffraction, were obatined by slow evaporation of a solution in methanol after four weeks.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing diagram of the title compound viewed along the a axis, with the N-H···O and C-H···O hydrogen bonds shown as dashed lines.

(4R*,5R*)-2-(4-Methoxyphenyl)-1,3-dioxolane-4,5-dicarboxamide top

Crystal data top

C₁₂H₁₄N₂O₅	F(000) = 560
M_r = 266.25	D_x = 1.399 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.9620 (14) Å	θ = 9–12°
b = 10.727 (2) Å	µ = 0.11 mm⁻¹
c = 16.932 (3) Å	T = 293 K
V = 1264.5 (4) Å³	Block, yellow
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.3°, θ_min = 2.3°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.978, T_max = 0.989	l = −20→20
2615 measured reflections	3 standard reflections every 200 reflections
2297 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.098P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2297 reflections	Δρ_max = 0.16 e Å⁻³
173 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (5)

Crystal data top

C₁₂H₁₄N₂O₅	V = 1264.5 (4) Å³
M_r = 266.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.9620 (14) Å	µ = 0.11 mm⁻¹
b = 10.727 (2) Å	T = 293 K
c = 16.932 (3) Å	0.20 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1939 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.035
T_min = 0.978, T_max = 0.989	3 standard reflections every 200 reflections
2615 measured reflections	intensity decay: 1%
2297 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
2297 reflections	Δρ_min = −0.16 e Å⁻³
173 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
O1	0.7648 (3)	0.69904 (17)	0.91700 (13)	0.0480 (5)
N1	0.6002 (4)	−0.0645 (2)	0.84147 (17)	0.0547 (7)
H1A	0.6483	−0.1329	0.8591	0.066*
H1B	0.6746	−0.0050	0.8266	0.066*
C1	0.9569 (4)	0.7107 (3)	0.9441 (2)	0.0572 (8)
H1C	0.9933	0.7970	0.9441	0.086*
H1D	1.0410	0.6649	0.9098	0.086*
H1E	0.9665	0.6781	0.9968	0.086*
O2	0.4731 (3)	0.17224 (15)	0.81276 (11)	0.0394 (5)
C2	0.6867 (4)	0.5817 (2)	0.91351 (15)	0.0369 (6)
N2	−0.0220 (4)	0.2673 (2)	0.76177 (16)	0.0544 (7)
H2A	−0.1036	0.2865	0.7256	0.065*
H2B	0.0432	0.3249	0.7848	0.065*
O3	0.2168 (3)	0.23134 (17)	0.88371 (11)	0.0417 (5)
C3	0.7876 (4)	0.4738 (3)	0.93091 (17)	0.0436 (7)
H3A	0.9146	0.4776	0.9477	0.052*
O4	0.2966 (3)	−0.13078 (18)	0.85712 (14)	0.0524 (6)
C4	0.6951 (4)	0.3598 (3)	0.92277 (17)	0.0440 (7)
H4A	0.7617	0.2870	0.9348	0.053*
O5	−0.0843 (3)	0.0617 (2)	0.75178 (15)	0.0587 (6)
C5	0.5076 (4)	0.3515 (2)	0.89740 (15)	0.0383 (6)
C6	0.4100 (4)	0.4611 (3)	0.88108 (18)	0.0439 (7)
H6A	0.2829	0.4574	0.8643	0.053*
C7	0.4980 (4)	0.5755 (3)	0.88927 (17)	0.0449 (6)
H7A	0.4302	0.6482	0.8785	0.054*
C8	0.4199 (4)	0.2252 (3)	0.88635 (16)	0.0394 (6)
H8A	0.4601	0.1701	0.9294	0.047*
C9	0.3416 (4)	0.0725 (2)	0.80307 (15)	0.0358 (6)
H9A	0.3170	0.0612	0.7465	0.043*
C10	0.1557 (4)	0.1216 (2)	0.84279 (16)	0.0389 (6)
H10A	0.1077	0.0600	0.8807	0.047*
C11	0.4124 (4)	−0.0509 (2)	0.83725 (17)	0.0404 (7)
C12	0.0032 (4)	0.1493 (2)	0.78190 (16)	0.0413 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0442 (11)	0.0306 (10)	0.0693 (13)	−0.0077 (9)	−0.0037 (9)	−0.0019 (9)
N1	0.0415 (14)	0.0295 (12)	0.093 (2)	−0.0034 (11)	−0.0067 (13)	0.0148 (14)
C1	0.0528 (19)	0.0486 (17)	0.070 (2)	−0.0190 (15)	−0.0076 (16)	0.0023 (16)
O2	0.0413 (11)	0.0243 (9)	0.0527 (10)	−0.0038 (8)	0.0054 (8)	0.0005 (8)
C2	0.0417 (15)	0.0281 (12)	0.0409 (13)	−0.0032 (12)	0.0013 (12)	−0.0011 (11)
N2	0.0564 (16)	0.0378 (13)	0.0689 (16)	0.0055 (12)	−0.0172 (14)	−0.0031 (12)
O3	0.0378 (10)	0.0356 (10)	0.0516 (11)	−0.0051 (8)	0.0018 (8)	−0.0084 (8)
C3	0.0383 (15)	0.0389 (15)	0.0537 (16)	−0.0010 (13)	−0.0111 (13)	0.0007 (12)
O4	0.0461 (12)	0.0288 (10)	0.0824 (14)	−0.0100 (9)	−0.0044 (11)	0.0089 (10)
C4	0.0453 (16)	0.0313 (14)	0.0554 (16)	0.0033 (13)	−0.0119 (13)	0.0029 (12)
O5	0.0483 (11)	0.0446 (12)	0.0833 (16)	−0.0088 (11)	−0.0161 (11)	−0.0066 (11)
C5	0.0448 (15)	0.0303 (12)	0.0398 (13)	−0.0030 (13)	−0.0042 (12)	0.0002 (10)
C6	0.0374 (14)	0.0341 (14)	0.0601 (17)	−0.0025 (12)	−0.0069 (13)	−0.0002 (12)
C7	0.0414 (15)	0.0285 (12)	0.0647 (17)	0.0025 (13)	−0.0014 (15)	0.0017 (12)
C8	0.0439 (15)	0.0314 (13)	0.0428 (14)	−0.0021 (12)	−0.0029 (12)	0.0058 (12)
C9	0.0380 (13)	0.0281 (12)	0.0413 (13)	−0.0038 (12)	−0.0020 (12)	0.0024 (11)
C10	0.0408 (15)	0.0274 (13)	0.0484 (14)	−0.0065 (11)	0.0033 (13)	0.0015 (11)
C11	0.0412 (15)	0.0261 (13)	0.0541 (16)	−0.0052 (12)	−0.0042 (13)	−0.0018 (11)
C12	0.0329 (12)	0.0352 (14)	0.0557 (16)	−0.0010 (13)	0.0008 (13)	−0.0032 (12)

Geometric parameters (Å, º) top

O1—C2	1.373 (3)	C3—C4	1.388 (4)
O1—C1	1.420 (4)	C3—H3A	0.9300
N1—C11	1.317 (4)	O4—C11	1.224 (3)
N1—H1A	0.8600	C4—C5	1.378 (4)
N1—H1B	0.8600	C4—H4A	0.9300
C1—H1C	0.9600	O5—C12	1.230 (3)
C1—H1D	0.9600	C5—C6	1.386 (4)
C1—H1E	0.9600	C5—C8	1.498 (4)
O2—C9	1.417 (3)	C6—C7	1.378 (4)
O2—C8	1.419 (3)	C6—H6A	0.9300
C2—C7	1.378 (4)	C7—H7A	0.9300
C2—C3	1.386 (4)	C8—H8A	0.9800
N2—C12	1.323 (4)	C9—C11	1.527 (4)
N2—H2A	0.8600	C9—C10	1.551 (4)
N2—H2B	0.8600	C9—H9A	0.9800
O3—C8	1.416 (3)	C10—C12	1.509 (4)
O3—C10	1.430 (3)	C10—H10A	0.9800

C2—O1—C1	117.9 (2)	C5—C6—H6A	119.4
C11—N1—H1A	120.0	C6—C7—C2	119.8 (3)
C11—N1—H1B	120.0	C6—C7—H7A	120.1
H1A—N1—H1B	120.0	C2—C7—H7A	120.1
O1—C1—H1C	109.5	O3—C8—O2	104.6 (2)
O1—C1—H1D	109.5	O3—C8—C5	111.7 (2)
H1C—C1—H1D	109.5	O2—C8—C5	111.4 (2)
O1—C1—H1E	109.5	O3—C8—H8A	109.7
H1C—C1—H1E	109.5	O2—C8—H8A	109.7
H1D—C1—H1E	109.5	C5—C8—H8A	109.7
C9—O2—C8	103.63 (19)	O2—C9—C11	113.7 (2)
O1—C2—C7	115.7 (2)	O2—C9—C10	103.43 (19)
O1—C2—C3	123.8 (2)	C11—C9—C10	113.6 (2)
C7—C2—C3	120.4 (3)	O2—C9—H9A	108.6
C12—N2—H2A	120.0	C11—C9—H9A	108.6
C12—N2—H2B	120.0	C10—C9—H9A	108.6
H2A—N2—H2B	120.0	O3—C10—C12	112.2 (2)
C8—O3—C10	105.9 (2)	O3—C10—C9	104.0 (2)
C2—C3—C4	118.6 (3)	C12—C10—C9	110.9 (2)
C2—C3—H3A	120.7	O3—C10—H10A	109.9
C4—C3—H3A	120.7	C12—C10—H10A	109.9
C5—C4—C3	121.8 (3)	C9—C10—H10A	109.9
C5—C4—H4A	119.1	O4—C11—N1	124.1 (3)
C3—C4—H4A	119.1	O4—C11—C9	119.9 (2)
C4—C5—C6	118.2 (3)	N1—C11—C9	115.9 (2)
C4—C5—C8	118.9 (2)	O5—C12—N2	123.9 (3)
C6—C5—C8	122.9 (2)	O5—C12—C10	118.8 (2)
C7—C6—C5	121.2 (3)	N2—C12—C10	117.2 (2)
C7—C6—H6A	119.4

C1—O1—C2—C7	178.0 (3)	C4—C5—C8—O2	−81.2 (3)
C1—O1—C2—C3	−3.5 (4)	C6—C5—C8—O2	96.9 (3)
O1—C2—C3—C4	−177.9 (3)	C8—O2—C9—C11	−90.3 (3)
C7—C2—C3—C4	0.5 (4)	C8—O2—C9—C10	33.4 (2)
C2—C3—C4—C5	0.5 (4)	C8—O3—C10—C12	−135.0 (2)
C3—C4—C5—C6	−1.1 (4)	C8—O3—C10—C9	−15.0 (3)
C3—C4—C5—C8	177.2 (3)	O2—C9—C10—O3	−11.4 (3)
C4—C5—C6—C7	0.5 (4)	C11—C9—C10—O3	112.3 (2)
C8—C5—C6—C7	−177.6 (3)	O2—C9—C10—C12	109.4 (2)
C5—C6—C7—C2	0.5 (4)	C11—C9—C10—C12	−126.9 (2)
O1—C2—C7—C6	177.5 (3)	O2—C9—C11—O4	155.4 (3)
C3—C2—C7—C6	−1.0 (4)	C10—C9—C11—O4	37.5 (4)
C10—O3—C8—O2	36.7 (3)	O2—C9—C11—N1	−26.2 (4)
C10—O3—C8—C5	157.3 (2)	C10—C9—C11—N1	−144.1 (3)
C9—O2—C8—O3	−44.4 (2)	O3—C10—C12—O5	−168.2 (3)
C9—O2—C8—C5	−165.1 (2)	C9—C10—C12—O5	76.0 (3)
C4—C5—C8—O3	162.3 (2)	O3—C10—C12—N2	14.7 (4)
C6—C5—C8—O3	−19.6 (4)	C9—C10—C12—N2	−101.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.21	3.063 (3)	174
N1—H1B···O5ⁱⁱ	0.86	2.22	2.994 (4)	149
N2—H2A···O4ⁱⁱⁱ	0.86	2.13	2.984 (4)	169
C7—H7A···O4^iv	0.93	2.57	3.491 (4)	170
C9—H9A···Cg2^v	0.98	2.83	3.737 (3)	154

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) −x, y+1/2, −z+3/2; (iv) x, y+1, z; (v) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₂O₅
M_r	266.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.9620 (14), 10.727 (2), 16.932 (3)
V (Å³)	1264.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.978, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	2615, 2297, 1939
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.135, 1.00
No. of reflections	2297
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.21	3.063 (3)	174
N1—H1B···O5ⁱⁱ	0.86	2.22	2.994 (4)	149
N2—H2A···O4ⁱⁱⁱ	0.86	2.13	2.984 (4)	169
C7—H7A···O4^iv	0.93	2.57	3.491 (4)	170
C9—H9A···Cg2^v	0.98	2.83	3.737 (3)	154

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) −x, y+1/2, −z+3/2; (iv) x, y+1, z; (v) −x+1, y−1/2, −z+3/2.

Acknowledgements

The authors thank Liu Bo Nian from Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for their support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Ates-Alagoz, Z. & Buyukbingol, E. (2001). Heterocycl. Commun. 7, 455–460. CAS Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Kim, D. K., Kim, G., Gam, J. S., Cho, Y. B. & Park, J. G. (1994). J. Med. Chem. 37, 1471–1485. CrossRef CAS PubMed Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Pandey, G., Hajra, S., Ghorai, M. K. & Kumar, K. R. (1997). J. Org. Chem. 62, 5966–5973. CSD CrossRef CAS Web of Science 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o558

doi:10.1107/S1600536812002401

Open

access