(4S,5S)-2-(2-Bromo-phen-yl)-1,3-dioxolane-4,5-dicarboxamide.

The asymmetric unit of the title compound, C(11)H(11)BrN(2)O(4), contains two crystallographically independent mol-ecules in which the bromo-phenyl rings are oriented at dihedral angles of 39.28 (3)°. The dioxolane rings adopt envelope conformations. Intra-molecular N-H⋯O hydrogen bonds result in the formation of four five-membered rings, having planar and envelope conformations. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link mol-ecules into chains along the b axis, forming R(2) (2)(8) ring motifs.

Related literature

For the use of similar compounds in the synthesis of platinum based anti-tumour agents and in organic syntheses, see: Kim et al. (1994 ▶); Pandey et al. (1997 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H11BrN2O4

M = 315.12

Monoclinic,

a = 9.4150 (19) Å

b = 14.458 (3) Å

c = 9.6170 (19) Å

β = 111.14 (3)°

V = 1221.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.38 mm−1

T = 294 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.552, T max = 0.729

4504 measured reflections

4256 independent reflections

2669 reflections with I > 2σ(I)

R int = 0.061

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.181

S = 1.00

4256 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.82 e Å−3

Absolute structure: Flack (1983 ▶), 1758 Friedel pairs

Flack parameter: 0.00 (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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010009/hk2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010009/hk2643Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H11BrN2O4	F(000) = 632
Mr = 315.12	Dx = 1.714 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 9.4150 (19) Å	θ = 10–13°
b = 14.458 (3) Å	µ = 3.38 mm−1
c = 9.6170 (19) Å	T = 294 K
β = 111.14 (3)°	Block, colorless
V = 1221.0 (5) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2669 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
graphite	θmax = 26.0°, θmin = 2.3°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −10→17
Tmin = 0.552, Tmax = 0.729	l = −11→11
4504 measured reflections	3 standard reflections every 120 min
4256 independent reflections	intensity decay: 1%

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)] = 0.063	H-atom parameters constrained
wR(F2) = 0.181	w = 1/[σ2(Fo2) + (0.1P)2 + 1.54P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4256 reflections	Δρmax = 0.54 e Å−3
325 parameters	Δρmin = −0.82 e Å−3
0 restraints	Absolute structure: Flack (1983), 1758 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (2)

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.

	x	y	z	Uiso*/Ueq
Br1	0.02596 (15)	0.99788 (7)	0.97303 (14)	0.0608 (5)
Br2	0.51991 (15)	0.59675 (7)	0.96846 (14)	0.0584 (4)
O1	0.2071 (7)	0.8476 (4)	1.2310 (7)	0.0342 (15)
O2	0.3547 (9)	0.7557 (5)	1.1503 (8)	0.045 (2)
O3	0.5492 (8)	0.9264 (5)	1.5118 (7)	0.0425 (17)
O4	0.5063 (11)	0.6732 (6)	1.5238 (9)	0.072 (3)
O5	0.1786 (8)	0.3598 (6)	0.8478 (8)	0.0402 (19)
O6	0.3262 (6)	0.4292 (4)	0.7424 (6)	0.0289 (14)
O7	−0.0743 (8)	0.2608 (5)	0.5162 (8)	0.051 (2)
O8	−0.0128 (9)	0.5151 (6)	0.4748 (10)	0.077 (3)
N1	0.3494 (10)	1.0032 (7)	1.3501 (9)	0.054 (2)
H1A	0.3872	1.0569	1.3798	0.065*
H1B	0.2618	0.9983	1.2798	0.065*
N2	0.3894 (12)	0.6010 (7)	1.3088 (9)	0.065 (3)
H2A	0.3936	0.5487	1.3527	0.078*
H2B	0.3480	0.6046	1.2133	0.078*
N3	0.1299 (12)	0.2007 (8)	0.6938 (12)	0.083 (4)
H3B	0.1123	0.1461	0.6557	0.100*
H3C	0.2075	0.2103	0.7737	0.100*
N4	0.2056 (10)	0.5835 (6)	0.5937 (10)	0.058 (3)
H4B	0.1804	0.6354	0.5475	0.070*
H4C	0.2946	0.5768	0.6609	0.070*
C1	−0.1253 (13)	0.8539 (9)	0.7843 (12)	0.054 (3)
H1C	−0.1973	0.8994	0.7406	0.065*
C2	−0.1452 (15)	0.7645 (9)	0.7283 (14)	0.063 (3)
H2C	−0.2335	0.7490	0.6491	0.076*
C3	−0.0347 (14)	0.6989 (9)	0.7897 (12)	0.060 (3)
H3A	−0.0477	0.6397	0.7492	0.072*
C4	0.0952 (12)	0.7193 (8)	0.9104 (12)	0.045 (3)
H4A	0.1685	0.6738	0.9501	0.055*
C5	0.1177 (10)	0.8071 (7)	0.9733 (10)	0.032 (2)
C6	0.0023 (11)	0.8736 (7)	0.9049 (11)	0.041 (2)
C7	0.2506 (12)	0.8300 (7)	1.1051 (11)	0.042 (3)
H7A	0.3017	0.8846	1.0846	0.051*
C8	0.4385 (13)	0.7664 (7)	1.3091 (12)	0.043 (3)
H8A	0.5406	0.7913	1.3284	0.051*
C9	0.3383 (11)	0.8363 (7)	1.3586 (10)	0.033 (2)
H9A	0.3110	0.8091	1.4389	0.040*
C10	0.4257 (11)	0.9281 (7)	1.4125 (10)	0.035 (2)
C11	0.4458 (12)	0.6747 (7)	1.3868 (11)	0.040 (2)
C12	0.6632 (12)	0.4664 (8)	1.1863 (12)	0.047 (3)
H12A	0.7377	0.5119	1.2195	0.057*
C13	0.6768 (12)	0.3799 (8)	1.2638 (11)	0.047 (3)
H13A	0.7629	0.3679	1.3475	0.056*
C14	0.5657 (12)	0.3166 (9)	1.2157 (12)	0.050 (3)
H14A	0.5721	0.2619	1.2687	0.060*
C15	0.4429 (12)	0.3328 (7)	1.0882 (11)	0.042 (2)
H15A	0.3687	0.2872	1.0542	0.051*
C16	0.4242 (11)	0.4149 (7)	1.0072 (10)	0.038 (2)
C17	0.5378 (11)	0.4786 (7)	1.0634 (10)	0.038 (2)
C18	0.2854 (10)	0.4319 (7)	0.8716 (10)	0.035 (2)
H18A	0.2392	0.4915	0.8789	0.042*
C19	0.0858 (10)	0.3643 (7)	0.6949 (11)	0.033 (2)
H19A	−0.0053	0.4007	0.6842	0.040*
C20	0.1849 (12)	0.4189 (7)	0.6234 (10)	0.041 (3)
H20A	0.1984	0.3824	0.5433	0.049*
C21	0.0373 (12)	0.2699 (7)	0.6293 (12)	0.041 (3)
C22	0.1035 (12)	0.5114 (7)	0.5599 (10)	0.039 (2)

	U11	U22	U33	U12	U13	U23
Br1	0.0828 (10)	0.0392 (9)	0.0483 (8)	0.0150 (7)	0.0090 (7)	0.0055 (7)
Br2	0.0742 (9)	0.0320 (8)	0.0488 (8)	−0.0102 (7)	−0.0022 (7)	0.0053 (7)
O1	0.041 (3)	0.031 (4)	0.028 (4)	0.001 (3)	0.009 (3)	−0.002 (3)
O2	0.070 (5)	0.033 (5)	0.028 (4)	0.010 (4)	0.011 (4)	−0.001 (3)
O3	0.061 (4)	0.026 (4)	0.031 (4)	−0.005 (3)	0.006 (3)	0.001 (3)
O4	0.113 (7)	0.032 (5)	0.035 (4)	0.013 (4)	−0.016 (4)	−0.006 (4)
O5	0.048 (4)	0.043 (5)	0.023 (4)	−0.007 (4)	0.005 (3)	0.000 (3)
O6	0.034 (3)	0.031 (4)	0.014 (3)	0.007 (3)	−0.001 (2)	0.000 (3)
O7	0.060 (4)	0.034 (5)	0.032 (4)	−0.001 (3)	−0.016 (3)	−0.005 (3)
O8	0.073 (5)	0.043 (6)	0.068 (6)	−0.003 (4)	−0.031 (5)	0.019 (4)
N1	0.063 (5)	0.030 (5)	0.045 (5)	−0.002 (5)	−0.010 (4)	−0.011 (5)
N2	0.121 (8)	0.030 (5)	0.024 (5)	−0.022 (6)	0.001 (5)	0.002 (5)
N3	0.091 (7)	0.033 (6)	0.071 (7)	0.008 (6)	−0.038 (6)	−0.003 (6)
N4	0.054 (5)	0.042 (7)	0.056 (6)	−0.003 (5)	−0.007 (4)	0.023 (5)
C1	0.060 (5)	0.062 (6)	0.035 (5)	0.007 (5)	0.012 (4)	0.007 (5)
C2	0.071 (6)	0.059 (6)	0.046 (6)	−0.016 (5)	0.006 (5)	0.006 (5)
C3	0.086 (6)	0.048 (6)	0.040 (5)	−0.012 (5)	0.015 (4)	−0.010 (5)
C4	0.062 (5)	0.032 (5)	0.037 (5)	−0.003 (4)	0.012 (4)	0.001 (4)
C5	0.034 (4)	0.033 (5)	0.029 (4)	−0.007 (4)	0.012 (3)	0.006 (4)
C6	0.054 (5)	0.038 (5)	0.030 (5)	0.006 (4)	0.015 (4)	0.008 (4)
C7	0.067 (7)	0.018 (6)	0.038 (6)	0.004 (5)	0.016 (5)	0.001 (5)
C8	0.064 (7)	0.015 (6)	0.033 (6)	0.001 (5)	−0.002 (5)	−0.003 (5)
C9	0.052 (6)	0.027 (6)	0.022 (5)	0.004 (4)	0.015 (4)	0.007 (4)
C10	0.052 (6)	0.033 (7)	0.019 (5)	0.004 (5)	0.010 (4)	0.002 (4)
C11	0.058 (6)	0.024 (6)	0.025 (5)	0.007 (5)	0.000 (4)	−0.005 (4)
C12	0.053 (5)	0.044 (6)	0.040 (5)	0.002 (4)	0.009 (4)	−0.003 (4)
C13	0.052 (5)	0.049 (6)	0.030 (5)	0.008 (4)	0.004 (4)	0.001 (4)
C14	0.058 (5)	0.050 (6)	0.034 (5)	0.004 (4)	0.008 (4)	0.007 (4)
C15	0.062 (5)	0.025 (5)	0.031 (5)	0.001 (4)	0.007 (4)	−0.003 (4)
C16	0.058 (5)	0.027 (5)	0.023 (4)	0.004 (4)	0.009 (4)	−0.003 (4)
C17	0.055 (5)	0.021 (5)	0.031 (5)	0.003 (4)	0.006 (4)	−0.004 (4)
C18	0.049 (5)	0.031 (6)	0.022 (5)	−0.006 (5)	0.009 (4)	−0.003 (4)
C19	0.033 (5)	0.025 (6)	0.036 (6)	−0.005 (4)	0.008 (4)	−0.007 (5)
C20	0.071 (7)	0.021 (6)	0.024 (5)	0.020 (5)	0.009 (5)	0.000 (4)
C21	0.048 (6)	0.028 (6)	0.038 (6)	−0.001 (5)	0.003 (5)	0.007 (5)
C22	0.059 (6)	0.030 (7)	0.019 (5)	0.003 (5)	0.002 (4)	0.005 (4)

Br1—C6	1.897 (11)	C2—H2C	0.9300
Br2—C17	1.915 (10)	C3—C4	1.381 (15)
O1—C9	1.402 (11)	C3—H3A	0.9300
O1—C7	1.434 (11)	C4—C5	1.389 (15)
O2—C7	1.414 (12)	C4—H4A	0.9300
O2—C8	1.453 (12)	C5—C6	1.422 (13)
O3—C10	1.210 (11)	C5—C7	1.462 (14)
O4—C11	1.232 (12)	C7—H7A	0.9800
O5—C18	1.409 (11)	C8—C11	1.511 (14)
O5—C19	1.416 (11)	C8—C9	1.568 (14)
O6—C20	1.416 (11)	C8—H8A	0.9800
O6—C18	1.427 (11)	C9—C10	1.549 (14)
O7—C21	1.217 (11)	C9—H9A	0.9800
O8—C22	1.107 (11)	C12—C17	1.348 (13)
N1—C10	1.321 (12)	C12—C13	1.437 (16)
N1—H1A	0.8600	C12—H12A	0.9300
N1—H1B	0.8600	C13—C14	1.341 (15)
N2—C11	1.301 (13)	C13—H13A	0.9300
N2—H2A	0.8600	C14—C15	1.369 (14)
N2—H2B	0.8600	C14—H14A	0.9300
N3—C21	1.324 (13)	C15—C16	1.395 (14)
N3—H3B	0.8600	C15—H15A	0.9300
N3—H3C	0.8600	C16—C17	1.367 (14)
N4—C22	1.375 (13)	C16—C18	1.497 (12)
N4—H4B	0.8600	C18—H18A	0.9800
N4—H4C	0.8600	C19—C21	1.504 (14)
C1—C6	1.366 (14)	C19—C20	1.559 (15)
C1—C2	1.386 (18)	C19—H19A	0.9800
C1—H1C	0.9300	C20—C22	1.552 (13)
C2—C3	1.374 (17)	C20—H20A	0.9800
C9—O1—C7	106.8 (7)	C10—C9—H9A	109.8
C7—O2—C8	107.2 (8)	C8—C9—H9A	109.8
C18—O5—C19	105.7 (7)	O3—C10—N1	125.8 (9)
C20—O6—C18	103.7 (7)	O3—C10—C9	119.4 (8)
C10—N1—H1A	120.0	N1—C10—C9	114.6 (8)
C10—N1—H1B	120.0	O4—C11—N2	122.5 (10)
H1A—N1—H1B	120.0	O4—C11—C8	117.7 (9)
C11—N2—H2A	120.0	N2—C11—C8	119.8 (9)
C11—N2—H2B	120.0	C17—C12—C13	117.1 (10)
H2A—N2—H2B	120.0	C17—C12—H12A	121.5
C21—N3—H3B	120.0	C13—C12—H12A	121.5
C21—N3—H3C	120.0	C14—C13—C12	120.2 (10)
H3B—N3—H3C	120.0	C14—C13—H13A	119.9
C22—N4—H4B	120.0	C12—C13—H13A	119.9
C22—N4—H4C	120.0	C13—C14—C15	119.6 (11)
H4B—N4—H4C	120.0	C13—C14—H14A	120.2
C6—C1—C2	118.7 (12)	C15—C14—H14A	120.2
C6—C1—H1C	120.7	C14—C15—C16	122.8 (11)
C2—C1—H1C	120.7	C14—C15—H15A	118.6
C3—C2—C1	120.1 (12)	C16—C15—H15A	118.6
C3—C2—H2C	120.0	C17—C16—C15	115.4 (9)
C1—C2—H2C	120.0	C17—C16—C18	123.1 (9)
C2—C3—C4	121.2 (12)	C15—C16—C18	121.4 (9)
C2—C3—H3A	119.4	C12—C17—C16	124.8 (10)
C4—C3—H3A	119.4	C12—C17—Br2	115.7 (8)
C3—C4—C5	120.7 (11)	C16—C17—Br2	119.4 (7)
C3—C4—H4A	119.6	O5—C18—O6	103.9 (7)
C5—C4—H4A	119.6	O5—C18—C16	111.5 (8)
C4—C5—C6	116.5 (9)	O6—C18—C16	109.3 (8)
C4—C5—C7	122.2 (9)	O5—C18—H18A	110.7
C6—C5—C7	121.3 (9)	O6—C18—H18A	110.7
C1—C6—C5	122.8 (11)	C16—C18—H18A	110.7
C1—C6—Br1	116.7 (8)	O5—C19—C21	112.0 (9)
C5—C6—Br1	120.4 (8)	O5—C19—C20	103.8 (7)
O2—C7—O1	104.7 (8)	C21—C19—C20	114.5 (9)
O2—C7—C5	112.1 (8)	O5—C19—H19A	108.8
O1—C7—C5	110.9 (8)	C21—C19—H19A	108.8
O2—C7—H7A	109.7	C20—C19—H19A	108.8
O1—C7—H7A	109.7	O6—C20—C22	114.5 (8)
C5—C7—H7A	109.7	O6—C20—C19	103.5 (7)
O2—C8—C11	109.7 (8)	C22—C20—C19	108.8 (8)
O2—C8—C9	103.3 (8)	O6—C20—H20A	110.0
C11—C8—C9	109.9 (9)	C22—C20—H20A	110.0
O2—C8—H8A	111.2	C19—C20—H20A	110.0
C11—C8—H8A	111.2	O7—C21—N3	123.2 (10)
C9—C8—H8A	111.2	O7—C21—C19	120.4 (9)
O1—C9—C10	112.7 (8)	N3—C21—C19	116.1 (9)
O1—C9—C8	104.3 (7)	O8—C22—N4	124.0 (10)
C10—C9—C8	110.4 (8)	O8—C22—C20	123.2 (10)
O1—C9—H9A	109.8	N4—C22—C20	110.9 (8)
C6—C1—C2—C3	−2.9 (18)	C17—C12—C13—C14	−1.8 (16)
C1—C2—C3—C4	2.1 (19)	C12—C13—C14—C15	3.3 (17)
C2—C3—C4—C5	0.0 (19)	C13—C14—C15—C16	−2.5 (18)
C3—C4—C5—C6	−1.2 (15)	C14—C15—C16—C17	0.3 (16)
C3—C4—C5—C7	177.3 (10)	C14—C15—C16—C18	−177.5 (10)
C2—C1—C6—C5	1.7 (16)	C13—C12—C17—C16	−0.5 (17)
C2—C1—C6—Br1	178.3 (9)	C13—C12—C17—Br2	177.4 (8)
C4—C5—C6—C1	0.4 (15)	C15—C16—C17—C12	1.2 (16)
C7—C5—C6—C1	−178.2 (10)	C18—C16—C17—C12	179.0 (10)
C4—C5—C6—Br1	−176.1 (8)	C15—C16—C17—Br2	−176.6 (7)
C7—C5—C6—Br1	5.3 (13)	C18—C16—C17—Br2	1.2 (14)
C8—O2—C7—O1	−33.6 (10)	C19—O5—C18—O6	−40.6 (9)
C8—O2—C7—C5	−153.9 (9)	C19—O5—C18—C16	−158.2 (8)
C9—O1—C7—O2	38.4 (9)	C20—O6—C18—O5	44.5 (8)
C9—O1—C7—C5	159.5 (8)	C20—O6—C18—C16	163.6 (8)
C4—C5—C7—O2	4.6 (14)	C17—C16—C18—O5	−173.1 (9)
C6—C5—C7—O2	−176.9 (8)	C15—C16—C18—O5	4.5 (14)
C4—C5—C7—O1	−111.9 (10)	C17—C16—C18—O6	72.7 (12)
C6—C5—C7—O1	66.6 (11)	C15—C16—C18—O6	−109.7 (10)
C7—O2—C8—C11	133.8 (9)	C18—O5—C19—C21	144.8 (9)
C7—O2—C8—C9	16.6 (10)	C18—O5—C19—C20	20.7 (10)
C7—O1—C9—C10	92.9 (9)	C18—O6—C20—C22	88.1 (9)
C7—O1—C9—C8	−26.9 (9)	C18—O6—C20—C19	−30.1 (9)
O2—C8—C9—O1	6.4 (10)	O5—C19—C20—O6	6.1 (9)
C11—C8—C9—O1	−110.6 (8)	C21—C19—C20—O6	−116.3 (8)
O2—C8—C9—C10	−114.9 (9)	O5—C19—C20—C22	−116.0 (8)
C11—C8—C9—C10	128.1 (9)	C21—C19—C20—C22	121.6 (9)
O1—C9—C10—O3	−172.2 (8)	O5—C19—C21—O7	158.6 (10)
C8—C9—C10—O3	−56.0 (11)	C20—C19—C21—O7	−83.5 (13)
O1—C9—C10—N1	12.7 (12)	O5—C19—C21—N3	−27.2 (14)
C8—C9—C10—N1	128.9 (9)	C20—C19—C21—N3	90.7 (13)
O2—C8—C11—O4	−176.2 (9)	O6—C20—C22—O8	−173.5 (11)
C9—C8—C11—O4	−63.3 (13)	C19—C20—C22—O8	−58.3 (14)
O2—C8—C11—N2	3.9 (15)	O6—C20—C22—N4	21.5 (12)
C9—C8—C11—N2	116.9 (11)	C19—C20—C22—N4	136.7 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.86	2.25	2.657 (12)	109
N2—H2B···O2	0.86	2.27	2.660 (12)	107
N3—H3B···O8i	0.86	2.28	3.123 (14)	167
N3—H3C···O5	0.86	2.32	2.684 (14)	106
N4—H4B···O7ii	0.86	2.05	2.876 (11)	160
N4—H4C···O6	0.86	2.26	2.672 (11)	110

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1	0.86	2.25	2.657 (12)	109
N2—H2B⋯O2	0.86	2.27	2.660 (12)	107
N3—H3B⋯O8i	0.86	2.28	3.123 (14)	167
N3—H3C⋯O5	0.86	2.32	2.684 (14)	106
N4—H4B⋯O7ii	0.86	2.05	2.876 (11)	160
N4—H4C⋯O6	0.86	2.26	2.672 (11)	110

Symmetry codes: (i) ; (ii) .