Methyl 2-amino-4-(3-chloro-prop-oxy)-5-methoxy-benzoate.

The asymmetric unit of the title compound, C(12)H(16)ClNO(4), contains two crystallographically independent mol-ecules. The benzene rings of the two independent mol-ecules are oriented at a dihedral angle of 88.50 (3)°. Intra-molecular N-H⋯O hydrogen bonds involving the methoxybenzoate carbonyl group in each molecule result in the formation of two planar, six-membered rings, oriented at dihedral angles of 1.39 (3) and 0.68 (3)° with respect to the adjacent benzene rings. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis.

Related literature

For general background to quinazoline derivatives, see: Knesl et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H16ClNO4

M = 273.71

Triclinic,

a = 8.1080 (16) Å

b = 9.818 (2) Å

c = 17.739 (3) Å

α = 82.07 (2)°

β = 83.41 (2)°

γ = 89.37 (3)°

V = 1389.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 294 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.921, T max = 0.973

5297 measured reflections

4919 independent reflections

2591 reflections with I > 2σ(I)

R int = 0.041

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

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.157

S = 1.01

4919 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

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/S1600536809011374/hk2651sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011374/hk2651Isup2.hkl

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

C12H16ClNO4	Z = 4
Mr = 273.71	F(000) = 576
Triclinic, P1	Dx = 1.309 Mg m−3
Hall symbol: -P 1	Melting point: 377 K
a = 8.1080 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.818 (2) Å	Cell parameters from 25 reflections
c = 17.739 (3) Å	θ = 9–13°
α = 82.07 (2)°	µ = 0.28 mm−1
β = 83.41 (2)°	T = 294 K
γ = 89.37 (3)°	Block, colorless
V = 1389.3 (5) Å3	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	2591 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
graphite	θmax = 25.3°, θmin = 1.2°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.921, Tmax = 0.973	l = −20→20
5297 measured reflections	3 standard reflections every 120 min
4919 independent reflections	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
4919 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	−0.15324 (14)	0.65740 (12)	0.56167 (7)	0.0986 (4)
Cl2	0.35436 (14)	0.80677 (12)	0.56017 (6)	0.0970 (4)
O1	−0.0021 (3)	0.9054 (2)	0.70177 (14)	0.0748 (7)
O2	0.2315 (3)	1.0836 (2)	0.66023 (13)	0.0713 (7)
O3	0.5434 (3)	0.8244 (3)	0.94591 (14)	0.0784 (7)
O4	0.6278 (3)	1.0083 (3)	0.85978 (14)	0.0764 (7)
O5	0.4986 (3)	0.4748 (2)	0.69292 (14)	0.0743 (7)
O6	0.7348 (3)	0.3139 (2)	0.65050 (13)	0.0713 (7)
O7	1.1359 (3)	0.2938 (2)	0.84821 (13)	0.0771 (8)
O8	1.0455 (3)	0.4302 (3)	0.93563 (13)	0.0753 (7)
N1	0.2572 (4)	0.7010 (3)	0.92623 (18)	0.0916 (10)
H1A	0.3373	0.6986	0.9542	0.110*
H1B	0.1770	0.6425	0.9381	0.110*
N2	0.7544 (4)	0.5646 (3)	0.91837 (16)	0.0812 (10)
H2C	0.8342	0.5523	0.9466	0.097*
H2D	0.6729	0.6173	0.9303	0.097*
C1	−0.1746 (5)	0.8327 (4)	0.5747 (2)	0.0916 (13)
H1C	−0.0664	0.8770	0.5646	0.110*
H1D	−0.2447	0.8784	0.5383	0.110*
C2	−0.2507 (4)	0.8486 (4)	0.6564 (3)	0.0880 (13)
H2A	−0.2840	0.9436	0.6574	0.106*
H2B	−0.3503	0.7924	0.6685	0.106*
C3	−0.1379 (4)	0.8095 (4)	0.7191 (2)	0.0764 (11)
H3A	−0.1966	0.8168	0.7691	0.092*
H3B	−0.0983	0.7160	0.7184	0.092*
C4	0.1200 (4)	0.8952 (3)	0.7498 (2)	0.0599 (9)
C5	0.1262 (4)	0.8003 (4)	0.8155 (2)	0.0660 (9)
H5A	0.0414	0.7356	0.8294	0.079*
C6	0.2574 (4)	0.7991 (3)	0.8619 (2)	0.0591 (9)
C7	0.3857 (4)	0.8969 (3)	0.84021 (18)	0.0552 (8)
C8	0.3773 (4)	0.9923 (3)	0.77157 (18)	0.0536 (8)
H8A	0.4628	1.0561	0.7566	0.064*
C9	0.2495 (4)	0.9941 (3)	0.72703 (19)	0.0553 (8)
C10	0.3629 (5)	1.1770 (4)	0.6326 (2)	0.0895 (13)
H10A	0.3364	1.2330	0.5868	0.134*
H10B	0.4630	1.1269	0.6213	0.134*
H10C	0.3786	1.2345	0.6708	0.134*
C11	0.5223 (4)	0.9032 (3)	0.88748 (19)	0.0562 (8)
C12	0.7633 (5)	1.0256 (4)	0.9052 (2)	0.0924 (13)
H12A	0.8318	1.1018	0.8807	0.139*
H12B	0.8288	0.9434	0.9093	0.139*
H12C	0.7185	1.0429	0.9554	0.139*
C13	0.3339 (5)	0.6258 (4)	0.5663 (2)	0.0937 (14)
H13A	0.2670	0.6044	0.5275	0.112*
H13B	0.4427	0.5856	0.5564	0.112*
C14	0.2526 (4)	0.5629 (4)	0.6458 (3)	0.0914 (13)
H14A	0.1515	0.6130	0.6580	0.110*
H14B	0.2214	0.4686	0.6434	0.110*
C15	0.3612 (4)	0.5635 (4)	0.7106 (2)	0.0767 (11)
H15A	0.4001	0.6559	0.7126	0.092*
H15B	0.2997	0.5290	0.7595	0.092*
C16	0.6215 (4)	0.4591 (3)	0.7408 (2)	0.0581 (9)
C17	0.7518 (4)	0.3703 (3)	0.71711 (18)	0.0546 (8)
C18	0.8796 (4)	0.3485 (3)	0.76205 (17)	0.0516 (8)
H18A	0.9653	0.2904	0.7476	0.062*
C19	0.8872 (4)	0.4108 (3)	0.83011 (17)	0.0485 (7)
C20	0.7570 (4)	0.4991 (3)	0.85342 (19)	0.0575 (8)
C21	0.6255 (4)	0.5203 (3)	0.8067 (2)	0.0618 (9)
H21A	0.5385	0.5774	0.8208	0.074*
C22	0.8708 (5)	0.2353 (4)	0.6222 (2)	0.0900 (13)
H22A	0.8456	0.2011	0.5766	0.135*
H22B	0.8905	0.1595	0.6604	0.135*
H22C	0.9682	0.2925	0.6104	0.135*
C23	1.0255 (4)	0.3818 (3)	0.87674 (18)	0.0523 (8)
C24	1.2755 (5)	0.2593 (4)	0.8929 (2)	0.0937 (14)
H24A	1.3482	0.1968	0.8683	0.141*
H24B	1.2343	0.2169	0.9435	0.141*
H24C	1.3356	0.3416	0.8962	0.141*

	U11	U22	U33	U12	U13	U23
Cl1	0.0972 (8)	0.1075 (9)	0.0950 (8)	0.0024 (6)	−0.0306 (6)	−0.0116 (6)
Cl2	0.1009 (8)	0.1059 (9)	0.0894 (8)	0.0022 (6)	−0.0347 (6)	−0.0126 (6)
O1	0.0498 (14)	0.0805 (17)	0.0951 (19)	−0.0060 (12)	−0.0240 (13)	−0.0026 (14)
O2	0.0595 (15)	0.0726 (16)	0.0808 (17)	−0.0087 (12)	−0.0293 (13)	0.0114 (13)
O3	0.0785 (17)	0.0769 (17)	0.0805 (18)	0.0031 (13)	−0.0326 (14)	0.0056 (14)
O4	0.0662 (16)	0.0832 (18)	0.0821 (17)	−0.0119 (14)	−0.0315 (13)	0.0007 (14)
O5	0.0503 (14)	0.0827 (16)	0.0981 (19)	0.0173 (12)	−0.0337 (13)	−0.0217 (14)
O6	0.0619 (15)	0.0820 (17)	0.0800 (17)	0.0160 (12)	−0.0338 (13)	−0.0268 (14)
O7	0.0794 (17)	0.0878 (18)	0.0771 (17)	0.0366 (14)	−0.0420 (14)	−0.0324 (14)
O8	0.0732 (16)	0.0944 (19)	0.0674 (16)	0.0184 (13)	−0.0250 (13)	−0.0315 (14)
N1	0.090 (2)	0.090 (2)	0.089 (2)	−0.0231 (19)	−0.0257 (19)	0.021 (2)
N2	0.083 (2)	0.097 (2)	0.072 (2)	0.0380 (18)	−0.0256 (17)	−0.0295 (18)
C1	0.077 (3)	0.104 (3)	0.092 (3)	−0.018 (2)	−0.038 (2)	0.017 (3)
C2	0.051 (2)	0.087 (3)	0.127 (4)	−0.0035 (19)	−0.026 (2)	−0.006 (3)
C3	0.052 (2)	0.093 (3)	0.086 (3)	−0.016 (2)	−0.0068 (19)	−0.017 (2)
C4	0.0443 (19)	0.067 (2)	0.071 (2)	0.0045 (16)	−0.0116 (17)	−0.0129 (19)
C5	0.059 (2)	0.063 (2)	0.076 (3)	−0.0071 (17)	−0.0097 (19)	−0.0052 (19)
C6	0.055 (2)	0.056 (2)	0.065 (2)	0.0012 (16)	−0.0076 (17)	−0.0035 (17)
C7	0.0506 (19)	0.055 (2)	0.061 (2)	0.0074 (16)	−0.0110 (16)	−0.0096 (17)
C8	0.0398 (17)	0.059 (2)	0.063 (2)	0.0000 (14)	−0.0102 (15)	−0.0059 (17)
C9	0.0496 (19)	0.053 (2)	0.064 (2)	0.0042 (15)	−0.0119 (16)	−0.0044 (16)
C10	0.087 (3)	0.084 (3)	0.092 (3)	−0.022 (2)	−0.033 (2)	0.027 (2)
C11	0.057 (2)	0.055 (2)	0.057 (2)	0.0072 (17)	−0.0102 (17)	−0.0104 (17)
C12	0.075 (3)	0.100 (3)	0.106 (3)	−0.013 (2)	−0.041 (2)	−0.003 (3)
C13	0.089 (3)	0.115 (3)	0.095 (3)	0.047 (3)	−0.051 (3)	−0.045 (3)
C14	0.054 (2)	0.087 (3)	0.140 (4)	0.011 (2)	−0.039 (3)	−0.018 (3)
C15	0.045 (2)	0.091 (3)	0.092 (3)	0.0118 (19)	−0.0162 (19)	0.000 (2)
C16	0.0459 (18)	0.060 (2)	0.071 (2)	0.0022 (15)	−0.0211 (17)	−0.0046 (18)
C17	0.0503 (19)	0.058 (2)	0.059 (2)	0.0051 (15)	−0.0188 (16)	−0.0122 (16)
C18	0.0455 (17)	0.0504 (19)	0.060 (2)	0.0031 (14)	−0.0135 (15)	−0.0041 (16)
C19	0.0481 (18)	0.0469 (18)	0.0492 (19)	0.0014 (14)	−0.0075 (14)	−0.0008 (14)
C20	0.060 (2)	0.057 (2)	0.055 (2)	0.0044 (16)	−0.0116 (17)	−0.0024 (16)
C21	0.0463 (19)	0.065 (2)	0.073 (2)	0.0118 (16)	−0.0070 (17)	−0.0062 (18)
C22	0.094 (3)	0.103 (3)	0.089 (3)	0.031 (2)	−0.046 (2)	−0.043 (2)
C23	0.057 (2)	0.0484 (19)	0.053 (2)	0.0024 (15)	−0.0117 (16)	−0.0073 (16)
C24	0.087 (3)	0.109 (3)	0.099 (3)	0.049 (2)	−0.053 (2)	−0.031 (3)

Cl1—C1	1.772 (4)	C6—C7	1.407 (4)
Cl2—C13	1.773 (4)	C7—C8	1.438 (4)
O1—C4	1.373 (4)	C7—C11	1.471 (4)
O1—C3	1.434 (4)	C8—C9	1.372 (4)
O2—C9	1.395 (4)	C8—H8A	0.9300
O2—C10	1.412 (4)	C10—H10A	0.9600
O3—C11	1.232 (4)	C10—H10B	0.9600
O4—C11	1.350 (4)	C10—H10C	0.9600
O4—C12	1.459 (4)	C12—H12A	0.9600
O5—C16	1.376 (3)	C12—H12B	0.9600
O5—C15	1.439 (4)	C12—H12C	0.9600
O6—C17	1.394 (3)	C13—C14	1.536 (6)
O6—C22	1.423 (4)	C13—H13A	0.9700
O7—C23	1.342 (4)	C13—H13B	0.9700
O7—C24	1.466 (4)	C14—C15	1.527 (5)
O8—C23	1.233 (3)	C14—H14A	0.9700
N1—C6	1.388 (4)	C14—H14B	0.9700
N1—H1A	0.8600	C15—H15A	0.9700
N1—H1B	0.8600	C15—H15B	0.9700
N2—C20	1.392 (4)	C16—C21	1.389 (4)
N2—H2C	0.8600	C16—C17	1.425 (4)
N2—H2D	0.8600	C17—C18	1.376 (4)
C1—C2	1.537 (5)	C18—C19	1.434 (4)
C1—H1C	0.9700	C18—H18A	0.9300
C1—H1D	0.9700	C19—C20	1.420 (4)
C2—C3	1.525 (5)	C19—C23	1.471 (4)
C2—H2A	0.9700	C20—C21	1.420 (4)
C2—H2B	0.9700	C21—H21A	0.9300
C3—H3A	0.9700	C22—H22A	0.9600
C3—H3B	0.9700	C22—H22B	0.9600
C4—C5	1.393 (5)	C22—H22C	0.9600
C4—C9	1.423 (4)	C24—H24A	0.9600
C5—C6	1.417 (4)	C24—H24B	0.9600
C5—H5A	0.9300	C24—H24C	0.9600
C4—O1—C3	118.2 (3)	O4—C12—H12A	109.5
C9—O2—C10	117.0 (2)	O4—C12—H12B	109.5
C11—O4—C12	115.7 (3)	H12A—C12—H12B	109.5
C16—O5—C15	118.5 (3)	O4—C12—H12C	109.5
C17—O6—C22	116.5 (2)	H12A—C12—H12C	109.5
C23—O7—C24	115.1 (3)	H12B—C12—H12C	109.5
C6—N1—H1A	120.0	C14—C13—Cl2	111.2 (3)
C6—N1—H1B	120.0	C14—C13—H13A	109.4
H1A—N1—H1B	120.0	Cl2—C13—H13A	109.4
C20—N2—H2C	120.0	C14—C13—H13B	109.4
C20—N2—H2D	120.0	Cl2—C13—H13B	109.4
H2C—N2—H2D	120.0	H13A—C13—H13B	108.0
C2—C1—Cl1	111.6 (3)	C15—C14—C13	114.9 (3)
C2—C1—H1C	109.3	C15—C14—H14A	108.5
Cl1—C1—H1C	109.3	C13—C14—H14A	108.5
C2—C1—H1D	109.3	C15—C14—H14B	108.5
Cl1—C1—H1D	109.3	C13—C14—H14B	108.5
H1C—C1—H1D	108.0	H14A—C14—H14B	107.5
C3—C2—C1	115.5 (3)	O5—C15—C14	105.4 (3)
C3—C2—H2A	108.4	O5—C15—H15A	110.7
C1—C2—H2A	108.4	C14—C15—H15A	110.7
C3—C2—H2B	108.4	O5—C15—H15B	110.7
C1—C2—H2B	108.4	C14—C15—H15B	110.7
H2A—C2—H2B	107.5	H15A—C15—H15B	108.8
O1—C3—C2	105.3 (3)	O5—C16—C21	125.9 (3)
O1—C3—H3A	110.7	O5—C16—C17	113.5 (3)
C2—C3—H3A	110.7	C21—C16—C17	120.6 (3)
O1—C3—H3B	110.7	C18—C17—O6	126.9 (3)
C2—C3—H3B	110.7	C18—C17—C16	117.2 (3)
H3A—C3—H3B	108.8	O6—C17—C16	115.9 (3)
O1—C4—C5	126.5 (3)	C17—C18—C19	123.3 (3)
O1—C4—C9	113.7 (3)	C17—C18—H18A	118.4
C5—C4—C9	119.8 (3)	C19—C18—H18A	118.4
C4—C5—C6	122.2 (3)	C20—C19—C18	119.2 (3)
C4—C5—H5A	118.9	C20—C19—C23	119.8 (3)
C6—C5—H5A	118.9	C18—C19—C23	120.9 (3)
N1—C6—C7	122.1 (3)	N2—C20—C19	123.2 (3)
N1—C6—C5	119.4 (3)	N2—C20—C21	119.9 (3)
C7—C6—C5	118.5 (3)	C19—C20—C21	116.9 (3)
C6—C7—C8	118.1 (3)	C16—C21—C20	122.7 (3)
C6—C7—C11	120.8 (3)	C16—C21—H21A	118.6
C8—C7—C11	121.0 (3)	C20—C21—H21A	118.6
C9—C8—C7	123.3 (3)	O6—C22—H22A	109.5
C9—C8—H8A	118.3	O6—C22—H22B	109.5
C7—C8—H8A	118.3	H22A—C22—H22B	109.5
C8—C9—O2	126.8 (3)	O6—C22—H22C	109.5
C8—C9—C4	118.0 (3)	H22A—C22—H22C	109.5
O2—C9—C4	115.2 (3)	H22B—C22—H22C	109.5
O2—C10—H10A	109.5	O8—C23—O7	120.9 (3)
O2—C10—H10B	109.5	O8—C23—C19	126.5 (3)
H10A—C10—H10B	109.5	O7—C23—C19	112.6 (3)
O2—C10—H10C	109.5	O7—C24—H24A	109.5
H10A—C10—H10C	109.5	O7—C24—H24B	109.5
H10B—C10—H10C	109.5	H24A—C24—H24B	109.5
O3—C11—O4	121.7 (3)	O7—C24—H24C	109.5
O3—C11—C7	126.1 (3)	H24A—C24—H24C	109.5
O4—C11—C7	112.1 (3)	H24B—C24—H24C	109.5
Cl1—C1—C2—C3	71.5 (4)	Cl2—C13—C14—C15	−70.8 (4)
C4—O1—C3—C2	179.4 (3)	C16—O5—C15—C14	177.8 (3)
C1—C2—C3—O1	63.9 (4)	C13—C14—C15—O5	−64.7 (4)
C3—O1—C4—C5	−0.5 (5)	C15—O5—C16—C21	0.9 (5)
C3—O1—C4—C9	179.3 (3)	C15—O5—C16—C17	−179.3 (3)
O1—C4—C5—C6	−179.4 (3)	C22—O6—C17—C18	−6.1 (5)
C9—C4—C5—C6	0.8 (5)	C22—O6—C17—C16	174.4 (3)
C4—C5—C6—N1	−179.4 (3)	O5—C16—C17—C18	−179.7 (3)
C4—C5—C6—C7	−0.4 (5)	C21—C16—C17—C18	0.1 (5)
N1—C6—C7—C8	178.5 (3)	O5—C16—C17—O6	−0.2 (4)
C5—C6—C7—C8	−0.4 (5)	C21—C16—C17—O6	179.6 (3)
N1—C6—C7—C11	−3.0 (5)	O6—C17—C18—C19	−179.8 (3)
C5—C6—C7—C11	178.1 (3)	C16—C17—C18—C19	−0.4 (5)
C6—C7—C8—C9	1.0 (5)	C17—C18—C19—C20	0.4 (5)
C11—C7—C8—C9	−177.5 (3)	C17—C18—C19—C23	178.9 (3)
C7—C8—C9—O2	179.5 (3)	C18—C19—C20—N2	−179.7 (3)
C7—C8—C9—C4	−0.7 (5)	C23—C19—C20—N2	1.8 (5)
C10—O2—C9—C8	4.2 (5)	C18—C19—C20—C21	0.0 (4)
C10—O2—C9—C4	−175.7 (3)	C23—C19—C20—C21	−178.6 (3)
O1—C4—C9—C8	179.9 (3)	O5—C16—C21—C20	−180.0 (3)
C5—C4—C9—C8	−0.2 (5)	C17—C16—C21—C20	0.2 (5)
O1—C4—C9—O2	−0.2 (4)	N2—C20—C21—C16	179.4 (3)
C5—C4—C9—O2	179.6 (3)	C19—C20—C21—C16	−0.2 (5)
C12—O4—C11—O3	−2.5 (5)	C24—O7—C23—O8	1.3 (5)
C12—O4—C11—C7	177.5 (3)	C24—O7—C23—C19	−179.1 (3)
C6—C7—C11—O3	3.5 (5)	C20—C19—C23—O8	−2.1 (5)
C8—C7—C11—O3	−177.9 (3)	C18—C19—C23—O8	179.3 (3)
C6—C7—C11—O4	−176.4 (3)	C20—C19—C23—O7	178.4 (3)
C8—C7—C11—O4	2.1 (4)	C18—C19—C23—O7	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.86	2.07	2.709 (4)	131
N1—H1B···O8i	0.86	2.36	3.155 (4)	154
N2—H2C···O8	0.86	2.09	2.719 (4)	130
N2—H2C···O8ii	0.86	2.43	3.216 (4)	152
N2—H2D···O3	0.86	2.31	3.119 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.86	2.07	2.709 (4)	131
N1—H1B⋯O8i	0.86	2.36	3.155 (4)	154
N2—H2C⋯O8	0.86	2.09	2.719 (4)	130
N2—H2C⋯O8ii	0.86	2.43	3.216 (4)	152
N2—H2D⋯O3	0.86	2.31	3.119 (4)	156

Symmetry codes: (i) ; (ii) .