p-Tolyl-methanaminium cyclo-hexane-1,2-diyl phosphate.

In the title mol-ecular salt, C(8)H(12)N(+)·C(6)H(10)O(4)P(-), the cation and anion are connected by N-H⋯O hydrogen bonds. The C atoms of the cyclo-hexane ring are disordered over two sets of sites in a 0.51 (4):0.49 (4) occupancy ratio to generate two superimposed chair conformations. One of the terminal phosphate O atoms is also disordered in a 0.62 (2):0.38 (2) ratio.

Related literature

For a related structure and background to organic phosphates, see: Gowda et al. (2010 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C8H12N+·C6H10O4P−

M = 299.30

Triclinic,

a = 5.9642 (6) Å

b = 9.6077 (10) Å

c = 13.7070 (15) Å

α = 78.326 (6)°

β = 82.549 (7)°

γ = 84.900 (6)°

V = 761.11 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 298 K

0.22 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.959, T max = 0.972

9372 measured reflections

3112 independent reflections

1549 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.177

S = 0.99

3112 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044326/hb5717sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044326/hb5717Isup2.hkl

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

C8H12N+·C6H10O4P−	Z = 2
Mr = 299.30	F(000) = 320
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9642 (6) Å	Cell parameters from 1420 reflections
b = 9.6077 (10) Å	θ = 2.4–19.6°
c = 13.7070 (15) Å	µ = 0.19 mm−1
α = 78.326 (6)°	T = 298 K
β = 82.549 (7)°	Block, colourless
γ = 84.900 (6)°	0.22 × 0.20 × 0.15 mm
V = 761.11 (14) Å3

Bruker APEXII CCD diffractometer	3112 independent reflections
Radiation source: fine-focus sealed tube	1549 reflections with I > 2σ(I)
graphite	Rint = 0.070
φ and ω scans	θmax = 27.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −7→6
Tmin = 0.959, Tmax = 0.972	k = −12→12
9372 measured reflections	l = −17→17

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) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0845P)2] where P = (Fo2 + 2Fc2)/3
3112 reflections	(Δ/σ)max = 0.002
217 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 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	Occ. (<1)
C1	0.1252 (8)	0.4020 (5)	0.8217 (3)	0.0796 (14)
H1A	−0.0022	0.4646	0.8385	0.119*
H1B	0.2040	0.3678	0.8796	0.119*
H1C	0.0731	0.3228	0.7999	0.119*
C2	0.2837 (6)	0.4820 (4)	0.7383 (3)	0.0494 (10)
C3	0.2204 (6)	0.6086 (4)	0.6806 (3)	0.0473 (10)
H3	0.0751	0.6492	0.6943	0.057*
C4	0.3634 (6)	0.6791 (4)	0.6024 (3)	0.0456 (10)
H4	0.3141	0.7655	0.5647	0.055*
C5	0.5811 (6)	0.6207 (4)	0.5803 (3)	0.0388 (9)
C6	0.6472 (6)	0.4933 (4)	0.6386 (3)	0.0533 (11)
H6	0.7928	0.4529	0.6257	0.064*
C7	0.5009 (7)	0.4247 (4)	0.7160 (3)	0.0567 (11)
H7	0.5492	0.3382	0.7539	0.068*
C8	0.7453 (6)	0.6848 (4)	0.4931 (3)	0.0519 (10)
H8A	0.8979	0.6640	0.5118	0.062*
H8B	0.7349	0.6389	0.4371	0.062*
C9	0.5555 (16)	0.0572 (10)	0.1899 (7)	0.0359 (17)	0.511 (5)
H9	0.6268	0.0962	0.2381	0.043*	0.511 (5)
C10	0.3502 (14)	0.1493 (9)	0.1592 (7)	0.0414 (17)	0.511 (5)
H10	0.2784	0.1120	0.1103	0.050*	0.511 (5)
C12	0.595 (3)	0.298 (2)	0.0267 (13)	0.071 (4)	0.511 (5)
H12A	0.6495	0.3920	0.0012	0.085*	0.511 (5)
H12B	0.5233	0.2705	−0.0255	0.085*	0.511 (5)
C13	0.802 (3)	0.189 (3)	0.0537 (14)	0.071 (4)	0.511 (5)
H13A	0.9034	0.1825	−0.0068	0.085*	0.511 (5)
H13B	0.8849	0.2224	0.0997	0.085*	0.511 (5)
C9A	0.4735 (15)	0.0466 (11)	0.1512 (7)	0.0359 (17)	0.489 (5)
H9A	0.3655	0.0470	0.1030	0.043*	0.489 (5)
C10A	0.4392 (14)	0.1751 (10)	0.1959 (7)	0.0414 (17)	0.489 (5)
H10A	0.5531	0.1797	0.2405	0.050*	0.489 (5)
C12A	0.683 (3)	0.302 (2)	0.0589 (14)	0.071 (4)	0.489 (5)
H12C	0.6978	0.3842	0.0048	0.085*	0.489 (5)
H12D	0.7896	0.3070	0.1057	0.085*	0.489 (5)
C13A	0.736 (3)	0.168 (3)	0.0176 (15)	0.071 (4)	0.489 (5)
H13C	0.8870	0.1693	−0.0183	0.085*	0.489 (5)
H13D	0.6291	0.1636	−0.0292	0.085*	0.489 (5)
C11	0.4260 (7)	0.3024 (4)	0.1158 (3)	0.0682 (13)
H11A	0.2961	0.3656	0.0968	0.082*
H11B	0.4924	0.3382	0.1660	0.082*
C14	0.7203 (6)	0.0391 (4)	0.1023 (3)	0.0541 (11)
H14A	0.6492	0.0002	0.0549	0.065*
H14B	0.8474	−0.0252	0.1234	0.065*
N1	0.7087 (6)	0.8402 (4)	0.4595 (3)	0.0508 (9)
O1	0.4388 (4)	−0.0703 (2)	0.23999 (19)	0.0548 (8)
O2	0.2054 (4)	0.1419 (3)	0.2529 (2)	0.0667 (9)
O3	0.2813 (4)	−0.0294 (3)	0.41168 (19)	0.0606 (8)
O4	0.001 (9)	−0.072 (10)	0.3026 (15)	0.089 (12)	0.62 (14)
O4A	0.051 (6)	−0.119 (3)	0.299 (2)	0.054 (6)	0.38 (14)
P1	0.22204 (15)	−0.01973 (11)	0.30949 (8)	0.0446 (4)
H3N	0.720 (6)	0.884 (4)	0.512 (3)	0.048 (12)*
H2N	0.552 (10)	0.869 (5)	0.440 (4)	0.12 (2)*
H1N	0.816 (9)	0.861 (5)	0.405 (4)	0.089 (16)*

	U11	U22	U33	U12	U13	U23
C1	0.067 (3)	0.085 (3)	0.073 (3)	−0.026 (2)	0.009 (3)	0.015 (3)
C2	0.044 (2)	0.053 (2)	0.050 (2)	−0.0162 (18)	0.0016 (19)	−0.007 (2)
C3	0.031 (2)	0.054 (2)	0.053 (2)	−0.0035 (16)	0.0041 (18)	−0.005 (2)
C4	0.037 (2)	0.042 (2)	0.053 (2)	−0.0010 (16)	0.0000 (18)	−0.0012 (18)
C5	0.0311 (19)	0.043 (2)	0.043 (2)	−0.0065 (15)	0.0013 (17)	−0.0117 (18)
C6	0.037 (2)	0.055 (3)	0.068 (3)	0.0015 (18)	0.000 (2)	−0.015 (2)
C7	0.060 (3)	0.041 (2)	0.066 (3)	0.0009 (19)	−0.009 (2)	−0.003 (2)
C8	0.042 (2)	0.062 (3)	0.051 (3)	−0.0062 (18)	0.0028 (19)	−0.013 (2)
C9	0.032 (5)	0.039 (3)	0.033 (6)	−0.005 (4)	−0.002 (3)	0.001 (4)
C10	0.024 (4)	0.045 (4)	0.049 (5)	−0.005 (3)	−0.002 (3)	0.005 (3)
C12	0.068 (12)	0.067 (4)	0.060 (11)	−0.009 (8)	0.005 (6)	0.022 (7)
C13	0.037 (9)	0.082 (8)	0.076 (12)	−0.013 (6)	0.013 (6)	0.017 (9)
C9A	0.032 (5)	0.039 (3)	0.033 (6)	−0.005 (4)	−0.002 (3)	0.001 (4)
C10A	0.024 (4)	0.045 (4)	0.049 (5)	−0.005 (3)	−0.002 (3)	0.005 (3)
C12A	0.068 (12)	0.067 (4)	0.060 (11)	−0.009 (8)	0.005 (6)	0.022 (7)
C13A	0.037 (9)	0.082 (8)	0.076 (12)	−0.013 (6)	0.013 (6)	0.017 (9)
C11	0.072 (3)	0.046 (2)	0.071 (3)	0.004 (2)	0.012 (2)	0.009 (2)
C14	0.043 (2)	0.063 (3)	0.047 (2)	0.0031 (18)	0.0098 (19)	−0.002 (2)
N1	0.036 (2)	0.074 (3)	0.041 (2)	−0.0198 (17)	0.0038 (18)	−0.005 (2)
O1	0.0565 (17)	0.0393 (15)	0.0598 (17)	−0.0088 (12)	0.0209 (13)	−0.0036 (13)
O2	0.0441 (17)	0.0680 (18)	0.0662 (19)	0.0195 (13)	0.0250 (14)	0.0087 (15)
O3	0.0517 (18)	0.086 (2)	0.0418 (17)	−0.0123 (14)	−0.0052 (13)	−0.0030 (14)
O4	0.047 (11)	0.17 (3)	0.047 (6)	−0.058 (16)	−0.005 (5)	0.007 (8)
O4A	0.028 (8)	0.068 (17)	0.071 (11)	−0.025 (6)	0.007 (6)	−0.023 (9)
P1	0.0272 (5)	0.0603 (7)	0.0411 (7)	−0.0103 (4)	0.0019 (4)	0.0019 (5)

C1—C2	1.511 (5)	C13—C14	1.55 (2)
C1—H1A	0.9600	C13—H13A	0.9700
C1—H1B	0.9600	C13—H13B	0.9700
C1—H1C	0.9600	C9A—C10A	1.474 (17)
C2—C3	1.362 (5)	C9A—O1	1.486 (10)
C2—C7	1.383 (5)	C9A—C14	1.538 (10)
C3—C4	1.381 (5)	C9A—H9A	0.9800
C3—H3	0.9300	C10A—C11	1.473 (10)
C4—C5	1.390 (5)	C10A—O2	1.534 (8)
C4—H4	0.9300	C10A—H10A	0.9800
C5—C6	1.376 (5)	C12A—C13A	1.50 (4)
C5—C8	1.507 (5)	C12A—C11	1.628 (19)
C6—C7	1.378 (5)	C12A—H12C	0.9700
C6—H6	0.9300	C12A—H12D	0.9700
C7—H7	0.9300	C13A—C14	1.52 (2)
C8—N1	1.476 (5)	C13A—H13C	0.9700
C8—H8A	0.9700	C13A—H13D	0.9700
C8—H8B	0.9700	C11—H11A	0.9700
C9—O1	1.464 (9)	C11—H11B	0.9700
C9—C14	1.478 (9)	C14—H14A	0.9700
C9—C10	1.500 (16)	C14—H14B	0.9700
C9—H9	0.9800	N1—H3N	0.92 (4)
C10—O2	1.445 (8)	N1—H2N	1.00 (6)
C10—C11	1.555 (9)	N1—H1N	0.92 (5)
C10—H10	0.9800	O1—P1	1.603 (2)
C12—C11	1.48 (2)	O2—P1	1.590 (3)
C12—C13	1.58 (3)	O3—P1	1.471 (3)
C12—H12A	0.9700	O4—P1	1.471 (17)
C12—H12B	0.9700	O4A—P1	1.50 (3)
C2—C1—H1A	109.5	O2—C10A—H10A	112.8
C2—C1—H1B	109.5	C13A—C12A—C11	109.5 (12)
H1A—C1—H1B	109.5	C13A—C12A—H12C	109.8
C2—C1—H1C	109.5	C11—C12A—H12C	109.8
H1A—C1—H1C	109.5	C13A—C12A—H12D	109.8
H1B—C1—H1C	109.5	C11—C12A—H12D	109.8
C3—C2—C7	117.3 (3)	H12C—C12A—H12D	108.2
C3—C2—C1	122.7 (4)	C12A—C13A—C14	110.0 (14)
C7—C2—C1	119.9 (4)	C12A—C13A—H13C	109.7
C2—C3—C4	122.6 (3)	C14—C13A—H13C	109.7
C2—C3—H3	118.7	C12A—C13A—H13D	109.7
C4—C3—H3	118.7	C14—C13A—H13D	109.7
C3—C4—C5	119.8 (3)	H13C—C13A—H13D	108.2
C3—C4—H4	120.1	C10A—C11—C12	114.1 (9)
C5—C4—H4	120.1	C10A—C11—C10	32.9 (4)
C6—C5—C4	118.0 (3)	C12—C11—C10	108.7 (9)
C6—C5—C8	118.0 (3)	C10A—C11—C12A	101.9 (8)
C4—C5—C8	123.9 (3)	C12—C11—C12A	26.9 (7)
C5—C6—C7	121.0 (4)	C10—C11—C12A	112.1 (9)
C5—C6—H6	119.5	C10A—C11—H11A	129.8
C7—C6—H6	119.5	C12—C11—H11A	109.9
C6—C7—C2	121.3 (4)	C10—C11—H11A	109.9
C6—C7—H7	119.4	C12A—C11—H11A	128.1
C2—C7—H7	119.4	C10A—C11—H11B	78.0
N1—C8—C5	114.7 (3)	C12—C11—H11B	109.9
N1—C8—H8A	108.6	C10—C11—H11B	109.9
C5—C8—H8A	108.6	C12A—C11—H11B	84.3
N1—C8—H8B	108.6	H11A—C11—H11B	108.3
C5—C8—H8B	108.6	C9—C14—C13A	115.1 (10)
H8A—C8—H8B	107.6	C9—C14—C9A	30.4 (3)
O1—C9—C14	115.2 (7)	C13A—C14—C9A	105.0 (9)
O1—C9—C10	97.5 (6)	C9—C14—C13	106.8 (9)
C14—C9—C10	111.7 (7)	C13A—C14—C13	27.7 (7)
O1—C9—H9	110.6	C9A—C14—C13	111.9 (9)
C14—C9—H9	110.6	C9—C14—H14A	110.4
C10—C9—H9	110.6	C13A—C14—H14A	82.9
O2—C10—C9	102.6 (7)	C9A—C14—H14A	80.9
O2—C10—C11	112.0 (6)	C13—C14—H14A	110.4
C9—C10—C11	107.8 (6)	C9—C14—H14B	110.4
O2—C10—H10	111.4	C13A—C14—H14B	125.1
C9—C10—H10	111.4	C9A—C14—H14B	129.5
C11—C10—H10	111.4	C13—C14—H14B	110.4
C11—C12—C13	111.2 (12)	H14A—C14—H14B	108.6
C11—C12—H12A	109.4	C8—N1—H3N	109 (2)
C13—C12—H12A	109.4	C8—N1—H2N	112 (3)
C11—C12—H12B	109.4	H3N—N1—H2N	105 (4)
C13—C12—H12B	109.4	C8—N1—H1N	104 (3)
H12A—C12—H12B	108.0	H3N—N1—H1N	116 (4)
C14—C13—C12	111.1 (10)	H2N—N1—H1N	111 (4)
C14—C13—H13A	109.4	C9—O1—C9A	31.2 (3)
C12—C13—H13A	109.4	C9—O1—P1	107.3 (4)
C14—C13—H13B	109.4	C9A—O1—P1	106.5 (4)
C12—C13—H13B	109.4	C10—O2—C10A	33.4 (4)
H13A—C13—H13B	108.0	C10—O2—P1	106.6 (4)
C10A—C9A—O1	102.8 (7)	C10A—O2—P1	107.4 (4)
C10A—C9A—C14	107.4 (7)	O4—P1—O3	115.7 (8)
O1—C9A—C14	110.5 (7)	O4—P1—O4A	20 (3)
C10A—C9A—H9A	111.9	O3—P1—O4A	115.4 (12)
O1—C9A—H9A	111.9	O4—P1—O2	104 (3)
C14—C9A—H9A	111.9	O3—P1—O2	110.38 (16)
C9A—C10A—C11	109.4 (8)	O4A—P1—O2	120.3 (14)
C9A—C10A—O2	96.3 (6)	O4—P1—O1	118 (3)
C11—C10A—O2	111.6 (6)	O3—P1—O1	109.49 (16)
C9A—C10A—H10A	112.8	O4A—P1—O1	101.8 (11)
C11—C10A—H10A	112.8	O2—P1—O1	96.79 (13)
C7—C2—C3—C4	0.1 (6)	C10—C9—C14—C13	63.4 (10)
C1—C2—C3—C4	−177.9 (4)	C12A—C13A—C14—C9	30.4 (14)
C2—C3—C4—C5	0.1 (6)	C12A—C13A—C14—C9A	61.0 (13)
C3—C4—C5—C6	−0.5 (5)	C12A—C13A—C14—C13	−48 (3)
C3—C4—C5—C8	176.4 (3)	C10A—C9A—C14—C9	49.1 (12)
C4—C5—C6—C7	0.8 (6)	O1—C9A—C14—C9	−62.3 (11)
C8—C5—C6—C7	−176.3 (3)	C10A—C9A—C14—C13A	−65.2 (11)
C5—C6—C7—C2	−0.7 (6)	O1—C9A—C14—C13A	−176.6 (8)
C3—C2—C7—C6	0.2 (6)	C10A—C9A—C14—C13	−36.9 (11)
C1—C2—C7—C6	178.2 (4)	O1—C9A—C14—C13	−148.2 (7)
C6—C5—C8—N1	−156.8 (3)	C12—C13—C14—C9	−55.5 (15)
C4—C5—C8—N1	26.3 (5)	C12—C13—C14—C13A	57 (3)
O1—C9—C10—O2	53.9 (7)	C12—C13—C14—C9A	−23.7 (16)
C14—C9—C10—O2	174.9 (5)	C14—C9—O1—C9A	−70.4 (12)
O1—C9—C10—C11	172.2 (5)	C10—C9—O1—C9A	47.9 (12)
C14—C9—C10—C11	−66.8 (9)	C14—C9—O1—P1	−163.7 (5)
C11—C12—C13—C14	54.8 (18)	C10—C9—O1—P1	−45.4 (7)
O1—C9A—C10A—C11	−169.5 (5)	C10A—C9A—O1—C9	−53.4 (12)
C14—C9A—C10A—C11	73.9 (9)	C14—C9A—O1—C9	60.9 (11)
O1—C9A—C10A—O2	−53.9 (7)	C10A—C9A—O1—P1	43.0 (7)
C14—C9A—C10A—O2	−170.5 (6)	C14—C9A—O1—P1	157.4 (5)
C11—C12A—C13A—C14	−61.2 (15)	C9—C10—O2—C10A	54.3 (10)
C9A—C10A—C11—C12	−42.3 (11)	C11—C10—O2—C10A	−61.0 (10)
O2—C10A—C11—C12	−147.6 (8)	C9—C10—O2—P1	−42.3 (7)
C9A—C10A—C11—C10	45.1 (9)	C11—C10—O2—P1	−157.6 (5)
O2—C10A—C11—C10	−60.2 (8)	C9A—C10A—O2—C10	−46.7 (10)
C9A—C10A—C11—C12A	−67.5 (10)	C11—C10A—O2—C10	67.1 (10)
O2—C10A—C11—C12A	−172.8 (8)	C9A—C10A—O2—P1	47.2 (7)
C13—C12—C11—C10A	−21.1 (16)	C11—C10A—O2—P1	161.0 (5)
C13—C12—C11—C10	−56.1 (15)	C10—O2—P1—O4	−108 (3)
C13—C12—C11—C12A	46 (3)	C10A—O2—P1—O4	−143 (3)
O2—C10—C11—C10A	67.5 (10)	C10—O2—P1—O3	127.1 (4)
C9—C10—C11—C10A	−44.6 (9)	C10A—O2—P1—O3	92.1 (5)
O2—C10—C11—C12	173.3 (6)	C10—O2—P1—O4A	−94.5 (13)
C9—C10—C11—C12	61.2 (10)	C10A—O2—P1—O4A	−129.5 (13)
O2—C10—C11—C12A	144.8 (7)	C10—O2—P1—O1	13.4 (4)
C9—C10—C11—C12A	32.7 (11)	C10A—O2—P1—O1	−21.6 (5)
C13A—C12A—C11—C10A	61.4 (15)	C9—O1—P1—O4	131 (3)
C13A—C12A—C11—C12	−59 (3)	C9A—O1—P1—O4	98 (3)
C13A—C12A—C11—C10	28.6 (16)	C9—O1—P1—O3	−93.8 (4)
O1—C9—C14—C13A	145.1 (7)	C9A—O1—P1—O3	−126.4 (4)
C10—C9—C14—C13A	35.1 (11)	C9—O1—P1—O4A	143.6 (15)
O1—C9—C14—C9A	68.6 (12)	C9A—O1—P1—O4A	111.0 (15)
C10—C9—C14—C9A	−41.4 (11)	C9—O1—P1—O2	20.7 (5)
O1—C9—C14—C13	173.4 (7)	C9A—O1—P1—O2	−11.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3N···O3i	0.92 (4)	1.90 (4)	2.788 (5)	161 (3)
N1—H2N···O3ii	1.00 (6)	1.86 (6)	2.834 (5)	164 (4)
N1—H1N···O4iii	0.92 (5)	1.72 (6)	2.63 (2)	171 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H3N⋯O3i	0.92 (4)	1.90 (4)	2.788 (5)	161 (3)
N1—H2N⋯O3ii	1.00 (6)	1.86 (6)	2.834 (5)	164 (4)
N1—H1N⋯O4iii	0.92 (5)	1.72 (6)	2.63 (2)	171 (5)

Symmetry codes: (i) ; (ii) ; (iii) .