Ethyl 4-(2,4-difluoro-phen-yl)-6-methyl-2-oxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

In the title compound, C(14)H(14)F(2)N(2)O(3), the dihydro-pyrimidin-one ring adopts a flattened boat conformation. The difluoro-phenyl group is disordered over two orientations with occupancies of 0.544 (3) and 0.456 (3). The methoxy-carbonyl group is disordered over two positions with occupancies of 0.580 (8) and 0.420 (8). In the crystal, mol-ecules are linked into centrosymmetric dimers by paired N-H⋯O hydrogen bonds and the dimers are linked into a ribbon-like structure along [100] by further N-H⋯O hydrogen bonds.

Related literature

For general background and pharmaceutical applications of pyrimidinones, see: Kalluraya & Rai (2003 ▶); Atwal (1990 ▶); Sadanandam et al. (1992 ▶); Steele et al. (1998 ▶); Manjula et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H14F2N2O3

M = 296.27

Triclinic,

a = 7.5176 (1) Å

b = 8.0483 (1) Å

c = 11.9323 (2) Å

α = 90.147 (1)°

β = 100.839 (1)°

γ = 108.421 (1)°

V = 671.25 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.43 × 0.32 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.949, T max = 0.985

17515 measured reflections

3075 independent reflections

2703 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.173

S = 1.08

3075 reflections

266 parameters

45 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015918/ci2792sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015918/ci2792Isup2.hkl

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

C14H14F2N2O3	Z = 2
Mr = 296.27	F(000) = 308
Triclinic, P1	Dx = 1.466 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5176 (1) Å	Cell parameters from 7927 reflections
b = 8.0483 (1) Å	θ = 2.7–34.4°
c = 11.9323 (2) Å	µ = 0.12 mm−1
α = 90.147 (1)°	T = 100 K
β = 100.839 (1)°	Plate, colourless
γ = 108.421 (1)°	0.43 × 0.32 × 0.13 mm
V = 671.25 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	3075 independent reflections
Radiation source: fine-focus sealed tube	2703 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.949, Tmax = 0.985	k = −10→10
17515 measured reflections	l = −15→15

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.8775P] where P = (Fo2 + 2Fc2)/3
3075 reflections	(Δ/σ)max = 0.001
266 parameters	Δρmax = 0.66 e Å−3
45 restraints	Δρmin = −0.84 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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	Occ. (<1)
F1A	0.7550 (6)	0.3028 (5)	0.3410 (3)	0.0598 (8)	0.544 (3)
F1B	0.8268 (7)	0.8571 (6)	0.2813 (4)	0.0598 (8)	0.456 (3)
O1	0.3876 (2)	0.1588 (2)	0.01956 (16)	0.0352 (4)
O2	1.2723 (2)	0.5461 (2)	0.14780 (15)	0.0298 (4)
O3	1.1456 (2)	0.7375 (2)	0.20789 (18)	0.0428 (5)
N1	0.5906 (2)	0.4172 (2)	0.10712 (14)	0.0207 (4)
N2	0.7014 (2)	0.1862 (2)	0.07956 (16)	0.0234 (4)
F2A	0.7967 (7)	0.7696 (9)	0.6102 (3)	0.0959 (19)	0.544 (3)
C1A	0.7750 (7)	0.4770 (8)	0.3704 (4)	0.0279 (8)	0.544 (3)
C2A	0.7792 (9)	0.5355 (13)	0.4811 (5)	0.0557 (19)	0.544 (3)
H2AA	0.7719	0.4586	0.5394	0.067*	0.544 (3)
C3A	0.7941 (12)	0.7054 (15)	0.5035 (6)	0.061 (2)	0.544 (3)
C4A	0.8048 (8)	0.8278 (10)	0.4216 (5)	0.0520 (16)	0.544 (3)
H4AA	0.8131	0.9433	0.4381	0.062*	0.544 (3)
C5A	0.8022 (7)	0.7640 (8)	0.3129 (5)	0.0332 (10)	0.544 (3)
H5AA	0.8107	0.8423	0.2554	0.040*	0.544 (3)
C6A	0.788 (3)	0.5949 (12)	0.2835 (7)	0.0180 (17)	0.544 (3)
F2B	0.7660 (6)	0.6163 (6)	0.6323 (2)	0.0479 (11)	0.456 (3)
C1B	0.8051 (8)	0.7153 (9)	0.3476 (5)	0.0279 (8)	0.456 (3)
C2B	0.8046 (11)	0.7414 (8)	0.4604 (6)	0.0255 (14)	0.456 (3)
H2BA	0.8265	0.8519	0.4945	0.031*	0.456 (3)
C3B	0.7694 (10)	0.5921 (9)	0.5204 (5)	0.0275 (13)	0.456 (3)
C4B	0.7384 (11)	0.4271 (8)	0.4734 (5)	0.0345 (14)	0.456 (3)
H4BA	0.7125	0.3326	0.5193	0.041*	0.456 (3)
C5B	0.7443 (9)	0.3954 (11)	0.3573 (5)	0.0332 (10)	0.456 (3)
H5BA	0.7301	0.2853	0.3256	0.040*	0.456 (3)
C6B	0.774 (3)	0.5502 (15)	0.2934 (11)	0.025 (3)	0.456 (3)
C7	0.7793 (3)	0.5371 (3)	0.16198 (16)	0.0182 (4)
H7A	0.7995	0.6433	0.1195	0.022*	0.580 (8)
H7B	0.7985	0.6385	0.1178	0.022*	0.420 (8)
C8	0.5505 (3)	0.2516 (3)	0.06653 (18)	0.0234 (4)
C9	0.8906 (3)	0.2904 (3)	0.11002 (16)	0.0197 (4)
C10	0.9344 (3)	0.4608 (3)	0.14452 (15)	0.0179 (4)
C11	1.1330 (3)	0.5786 (3)	0.16561 (16)	0.0198 (4)
C12	1.3361 (4)	0.8646 (4)	0.2385 (3)	0.0541 (9)
H12A	1.3717	0.9251	0.1718	0.065*	0.580 (8)
H12B	1.4283	0.8057	0.2670	0.065*	0.580 (8)
H12C	1.4223	0.8259	0.2019	0.065*	0.420 (8)
H12D	1.3332	0.9763	0.2093	0.065*	0.420 (8)
C13A	1.3350 (6)	0.9926 (6)	0.3285 (4)	0.0367 (13)	0.580 (8)
H13A	1.4629	1.0700	0.3559	0.055*	0.580 (8)
H13B	1.2866	0.9305	0.3908	0.055*	0.580 (8)
H13C	1.2546	1.0599	0.2970	0.055*	0.580 (8)
C13B	1.4024 (9)	0.8870 (8)	0.3480 (5)	0.0355 (17)	0.420 (8)
H13D	1.4307	0.7841	0.3750	0.053*	0.420 (8)
H13E	1.3085	0.9070	0.3861	0.053*	0.420 (8)
H13F	1.5170	0.9866	0.3640	0.053*	0.420 (8)
C14	1.0280 (3)	0.1943 (3)	0.09888 (19)	0.0242 (4)
H14A	1.1389	0.2365	0.1591	0.036*
H14B	1.0657	0.2138	0.0262	0.036*
H14C	0.9676	0.0710	0.1042	0.036*
H1N1	0.493 (4)	0.458 (4)	0.105 (2)	0.034 (7)*
H1N2	0.674 (4)	0.081 (4)	0.052 (2)	0.035 (7)*

	U11	U22	U33	U12	U13	U23
F1A	0.078 (2)	0.0668 (19)	0.0584 (16)	0.0393 (16)	0.0423 (15)	0.0248 (14)
F1B	0.078 (2)	0.0668 (19)	0.0584 (16)	0.0393 (16)	0.0423 (15)	0.0248 (14)
O1	0.0139 (7)	0.0315 (8)	0.0586 (11)	0.0057 (6)	0.0059 (7)	−0.0174 (8)
O2	0.0166 (7)	0.0307 (8)	0.0447 (9)	0.0085 (6)	0.0107 (6)	0.0018 (7)
O3	0.0160 (8)	0.0346 (9)	0.0721 (13)	−0.0006 (7)	0.0104 (8)	−0.0262 (9)
N1	0.0141 (8)	0.0243 (9)	0.0253 (8)	0.0088 (7)	0.0032 (6)	−0.0036 (7)
N2	0.0160 (8)	0.0206 (8)	0.0350 (10)	0.0063 (7)	0.0081 (7)	−0.0045 (7)
F2A	0.081 (3)	0.165 (5)	0.0359 (19)	0.034 (3)	0.0086 (18)	−0.043 (3)
C1A	0.0253 (17)	0.047 (2)	0.0141 (15)	0.0144 (16)	0.0068 (12)	0.0079 (16)
C2A	0.039 (3)	0.102 (6)	0.023 (3)	0.018 (4)	0.008 (2)	0.002 (4)
C3A	0.039 (3)	0.112 (7)	0.026 (4)	0.018 (5)	0.003 (3)	−0.023 (4)
C4A	0.030 (3)	0.071 (4)	0.049 (3)	0.012 (3)	0.002 (2)	−0.039 (3)
C5A	0.0261 (18)	0.051 (3)	0.0162 (16)	0.0024 (17)	0.0063 (13)	−0.0106 (19)
C6A	0.010 (3)	0.031 (5)	0.012 (2)	0.004 (4)	0.0039 (16)	−0.003 (2)
F2B	0.079 (3)	0.073 (3)	0.0113 (13)	0.051 (2)	0.0125 (14)	0.0029 (15)
C1B	0.0253 (17)	0.047 (2)	0.0141 (15)	0.0144 (16)	0.0068 (12)	0.0079 (16)
C2B	0.040 (3)	0.017 (2)	0.025 (3)	0.019 (2)	0.002 (3)	−0.002 (2)
C3B	0.041 (3)	0.036 (3)	0.015 (3)	0.023 (3)	0.008 (2)	0.005 (2)
C4B	0.058 (4)	0.028 (3)	0.028 (3)	0.023 (3)	0.016 (3)	0.011 (2)
C5B	0.0261 (18)	0.051 (3)	0.0162 (16)	0.0024 (17)	0.0063 (13)	−0.0106 (19)
C6B	0.016 (4)	0.025 (5)	0.036 (5)	0.008 (5)	0.005 (3)	−0.005 (3)
C7	0.0150 (9)	0.0218 (9)	0.0189 (9)	0.0073 (7)	0.0039 (7)	−0.0009 (7)
C8	0.0159 (9)	0.0252 (10)	0.0304 (10)	0.0067 (8)	0.0080 (8)	−0.0038 (8)
C9	0.0156 (9)	0.0262 (10)	0.0196 (9)	0.0084 (8)	0.0062 (7)	0.0020 (7)
C10	0.0144 (9)	0.0250 (10)	0.0159 (8)	0.0081 (7)	0.0043 (7)	0.0012 (7)
C11	0.0173 (9)	0.0269 (10)	0.0162 (8)	0.0082 (8)	0.0041 (7)	0.0013 (7)
C12	0.0205 (12)	0.0508 (17)	0.078 (2)	−0.0088 (11)	0.0148 (13)	−0.0355 (15)
C13A	0.033 (2)	0.028 (2)	0.042 (2)	0.0054 (17)	−0.0014 (18)	−0.0057 (17)
C13B	0.032 (3)	0.035 (3)	0.034 (3)	0.007 (2)	−0.001 (2)	−0.006 (2)
C14	0.0198 (10)	0.0261 (10)	0.0308 (11)	0.0112 (8)	0.0085 (8)	0.0002 (8)

F1A—C1A	1.398 (6)	C3B—C4B	1.373 (8)
F1B—C1B	1.375 (7)	C4B—C5B	1.418 (8)
O1—C8	1.238 (3)	C4B—H4BA	0.93
O2—C11	1.211 (2)	C5B—C6B	1.441 (12)
O3—C11	1.342 (3)	C5B—H5BA	0.93
O3—C12	1.451 (3)	C6B—C7	1.579 (12)
N1—C8	1.337 (3)	C7—C10	1.524 (3)
N1—C7	1.468 (2)	C7—H7A	0.98
N1—H1N1	0.89 (3)	C7—H7B	0.96
N2—C8	1.379 (3)	C9—C10	1.349 (3)
N2—C9	1.382 (3)	C9—C14	1.496 (3)
N2—H1N2	0.86 (3)	C10—C11	1.467 (3)
F2A—C3A	1.367 (7)	C12—C13B	1.299 (7)
C1A—C2A	1.392 (8)	C12—C13A	1.490 (5)
C1A—C6A	1.404 (9)	C12—H12A	0.97
C2A—C3A	1.358 (11)	C12—H12B	0.97
C2A—H2AA	0.93	C12—H12C	0.97
C3A—C4A	1.384 (11)	C12—H12D	0.97
C4A—C5A	1.388 (7)	C13A—H12D	1.4259
C4A—H4AA	0.93	C13A—H13A	0.96
C5A—C6A	1.371 (11)	C13A—H13B	0.96
C5A—H5AA	0.93	C13A—H13C	0.96
C6A—C7	1.505 (8)	C13B—H13D	0.96
F2B—C3B	1.355 (6)	C13B—H13E	0.96
C1B—C2B	1.362 (8)	C13B—H13F	0.96
C1B—C6B	1.409 (12)	C14—H14A	0.96
C2B—C3B	1.378 (7)	C14—H14B	0.96
C2B—H2BA	0.93	C14—H14C	0.96
C11—O3—C12	116.68 (18)	C10—C7—H7B	104.8
C8—N1—C7	126.65 (17)	C6B—C7—H7B	121.4
C8—N1—H1N1	117.3 (18)	O1—C8—N1	123.06 (19)
C7—N1—H1N1	115.9 (18)	O1—C8—N2	120.41 (19)
C8—N2—C9	123.28 (18)	N1—C8—N2	116.53 (18)
C8—N2—H1N2	115 (2)	C10—C9—N2	119.93 (18)
C9—N2—H1N2	120 (2)	C10—C9—C14	126.95 (18)
C2A—C1A—F1A	122.6 (6)	N2—C9—C14	113.12 (17)
C2A—C1A—C6A	119.6 (7)	C9—C10—C11	120.89 (17)
F1A—C1A—C6A	117.9 (5)	C9—C10—C7	121.08 (17)
C3A—C2A—C1A	119.6 (6)	C11—C10—C7	118.04 (17)
C3A—C2A—H2AA	120.2	O2—C11—O3	121.61 (18)
C1A—C2A—H2AA	120.2	O2—C11—C10	127.53 (19)
C2A—C3A—F2A	122.2 (8)	O3—C11—C10	110.85 (16)
C2A—C3A—C4A	123.8 (6)	C13B—C12—O3	113.2 (4)
F2A—C3A—C4A	114.0 (8)	C13B—C12—C13A	46.9 (3)
C3A—C4A—C5A	114.5 (6)	O3—C12—C13A	108.3 (3)
C3A—C4A—H4AA	122.7	C13B—C12—H12A	135.7
C5A—C4A—H4AA	122.7	O3—C12—H12A	110.0
C6A—C5A—C4A	125.2 (7)	C13A—C12—H12A	110.0
C6A—C5A—H5AA	117.4	C13B—C12—H12B	64.7
C4A—C5A—H5AA	117.4	O3—C12—H12B	110.0
C5A—C6A—C1A	117.2 (6)	C13A—C12—H12B	110.0
C5A—C6A—C7	121.1 (7)	H12A—C12—H12B	108.4
C1A—C6A—C7	121.6 (7)	C13B—C12—H12C	108.9
C2B—C1B—F1B	118.1 (6)	O3—C12—H12C	108.9
C2B—C1B—C6B	124.0 (7)	C13A—C12—H12C	141.9
F1B—C1B—C6B	117.9 (6)	H12A—C12—H12C	63.9
C1B—C2B—C3B	115.2 (5)	H12B—C12—H12C	48.0
C1B—C2B—H2BA	122.4	C13B—C12—H12D	109.0
C3B—C2B—H2BA	122.4	O3—C12—H12D	109.0
F2B—C3B—C4B	120.2 (5)	C13A—C12—H12D	67.0
F2B—C3B—C2B	115.7 (6)	H12A—C12—H12D	46.1
C4B—C3B—C2B	124.1 (5)	H12B—C12—H12D	139.4
C3B—C4B—C5B	122.4 (6)	H12C—C12—H12D	107.8
C3B—C4B—H4BA	118.8	C12—C13A—H13A	109.5
C5B—C4B—H4BA	118.8	H12D—C13A—H13A	100.8
C4B—C5B—C6B	113.6 (8)	C12—C13A—H13B	109.5
C4B—C5B—H5BA	123.2	H12D—C13A—H13B	143.5
C6B—C5B—H5BA	123.2	C12—C13A—H13C	109.5
C1B—C6B—C5B	120.6 (9)	H12D—C13A—H13C	77.8
C1B—C6B—C7	119.2 (7)	C12—C13B—H13D	109.5
C5B—C6B—C7	120.1 (8)	C12—C13B—H13E	109.5
N1—C7—C6A	113.1 (6)	H13D—C13B—H13E	109.5
N1—C7—C10	109.82 (15)	C12—C13B—H13F	109.5
C6A—C7—C10	115.3 (7)	H13D—C13B—H13F	109.5
N1—C7—C6B	105.6 (8)	H13E—C13B—H13F	109.5
C10—C7—C6B	110.0 (8)	C9—C14—H14A	109.5
N1—C7—H7A	105.9	C9—C14—H14B	109.5
C6A—C7—H7A	105.9	H14A—C14—H14B	109.5
C10—C7—H7A	105.9	C9—C14—H14C	109.5
C6B—C7—H7A	119.3	H14A—C14—H14C	109.5
N1—C7—H7B	104.8	H14B—C14—H14C	109.5
C6A—C7—H7B	108.1
F1A—C1A—C2A—C3A	−178.4 (6)	C5A—C6A—C7—C6B	−168 (8)
C6A—C1A—C2A—C3A	0.7 (12)	C1A—C6A—C7—C6B	10 (5)
C1A—C2A—C3A—F2A	179.2 (6)	C1B—C6B—C7—N1	−120.8 (15)
C1A—C2A—C3A—C4A	0.3 (12)	C5B—C6B—C7—N1	60.9 (18)
C2A—C3A—C4A—C5A	−1.0 (11)	C1B—C6B—C7—C6A	5(5)
F2A—C3A—C4A—C5A	−180.0 (5)	C5B—C6B—C7—C6A	−173 (8)
C3A—C4A—C5A—C6A	0.8 (12)	C1B—C6B—C7—C10	120.7 (15)
C4A—C5A—C6A—C1A	0.1 (18)	C5B—C6B—C7—C10	−57.6 (18)
C4A—C5A—C6A—C7	177.7 (8)	C7—N1—C8—O1	−178.9 (2)
C2A—C1A—C6A—C5A	−0.9 (17)	C7—N1—C8—N2	1.3 (3)
F1A—C1A—C6A—C5A	178.2 (9)	C9—N2—C8—O1	166.8 (2)
C2A—C1A—C6A—C7	−178.4 (9)	C9—N2—C8—N1	−13.3 (3)
F1A—C1A—C6A—C7	0.6 (17)	C8—N2—C9—C10	9.5 (3)
F1B—C1B—C2B—C3B	175.8 (6)	C8—N2—C9—C14	−169.96 (19)
C6B—C1B—C2B—C3B	−0.7 (16)	N2—C9—C10—C11	−173.48 (17)
C1B—C2B—C3B—F2B	−179.1 (5)	C14—C9—C10—C11	6.0 (3)
C1B—C2B—C3B—C4B	0.7 (12)	N2—C9—C10—C7	6.1 (3)
F2B—C3B—C4B—C5B	−178.7 (6)	C14—C9—C10—C7	−174.45 (18)
C2B—C3B—C4B—C5B	1.5 (12)	N1—C7—C10—C9	−15.5 (2)
C3B—C4B—C5B—C6B	−3.4 (14)	C6A—C7—C10—C9	113.7 (5)
C2B—C1B—C6B—C5B	−1(3)	C6B—C7—C10—C9	100.3 (6)
F1B—C1B—C6B—C5B	−178.0 (13)	N1—C7—C10—C11	164.14 (16)
C2B—C1B—C6B—C7	−179.8 (10)	C6A—C7—C10—C11	−66.7 (5)
F1B—C1B—C6B—C7	4(2)	C6B—C7—C10—C11	−80.1 (6)
C4B—C5B—C6B—C1B	3(2)	C12—O3—C11—O2	−4.1 (3)
C4B—C5B—C6B—C7	−178.4 (12)	C12—O3—C11—C10	176.8 (2)
C8—N1—C7—C6A	−118.4 (5)	C9—C10—C11—O2	6.0 (3)
C8—N1—C7—C10	12.0 (3)	C7—C10—C11—O2	−173.63 (19)
C8—N1—C7—C6B	−106.5 (7)	C9—C10—C11—O3	−174.99 (18)
C5A—C6A—C7—N1	−109.7 (12)	C7—C10—C11—O3	5.4 (2)
C1A—C6A—C7—N1	67.8 (15)	C11—O3—C12—C13B	−104.0 (4)
C5A—C6A—C7—C10	122.8 (12)	C11—O3—C12—C13A	−154.2 (3)
C1A—C6A—C7—C10	−59.7 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.89 (3)	2.14 (3)	3.007 (2)	165 (2)
N2—H1N2···O1ii	0.86 (3)	1.99 (3)	2.840 (2)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.89 (3)	2.14 (3)	3.007 (2)	165 (2)
N2—H1N2⋯O1ii	0.86 (3)	1.99 (3)	2.840 (2)	177 (3)

Symmetry codes: (i) ; (ii) .