2-[(2-Carboxyphenyl)disulfanyl]benzoate (1,5-dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1H-pyrazol-4-yl)ammonium.

In the title molecular salt, C(11)H(14)N(3)O(+)·C(14)H(9)O(4)S(2) (-), one of the carboxylic groups of the 2,2'-dithio-dibenzoic acid is deprotonated and the exocyclic amino N atom of the 4-amino-anti-pyrine is protonated. In the anion, the dihedral angle between the two benzene rings is 73.51 (5)° and in the cation the dihedral angle between the phenyl ring and the five-membered ring is 65.79 (9)°. In the crystal structure, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds connect the anions and cations into chains along [010].

Related literature

For mol­ecular recognition by intermolecular non-covalent interactions, see Rebek (1990 ▶); Remenar et al. (2003 ▶). For the properties and applications of 4-amino­anti­pyrine and its derivatives, see Wang et al. (2008b ▶); Ismail et al. (1997 ▶); Selvakumar et al. (2007 ▶); Meffin et al. (1977 ▶). For the structures and properties of 2,2′-dithio­dibenzoic acid-based metal complexes and cocrystals, see Basiuk et al. (1999 ▶); Murugavel et al. (2001 ▶); Broker et al. (2007 ▶; 2008 ▶); Meng et al. (2008 ▶); Wang et al, (2008a ▶, 2009 ▶).

Experimental

Crystal data

C11H14N3O+·C14H9O4S2 −

M = 509.58

Triclinic,

a = 9.661 (3) Å

b = 10.283 (4) Å

c = 13.829 (7) Å

α = 99.872 (7)°

β = 91.929 (7)°

γ = 115.244 (5)°

V = 1215.5 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.30 × 0.28 × 0.22 mm

Data collection

Brucker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.926, T max = 0.945

6173 measured reflections

4227 independent reflections

3634 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.06

4227 reflections

320 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036952/lh2900sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036952/lh2900Isup2.hkl

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

C11H14N3O+·C14H9O4S2−	Z = 2
Mr = 509.58	F(000) = 532
Triclinic, P1	Dx = 1.392 Mg m−3
a = 9.661 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.283 (4) Å	Cell parameters from 4106 reflections
c = 13.829 (7) Å	θ = 2.4–27.8°
α = 99.872 (7)°	µ = 0.26 mm−1
β = 91.929 (7)°	T = 296 K
γ = 115.244 (5)°	Block, yellow
V = 1215.5 (9) Å3	0.30 × 0.28 × 0.22 mm

Brucker APEXII CCD area-detector diffractometer	4227 independent reflections
Radiation source: fine-focus sealed tube	3634 reflections with I > 2σ(I)
graphite	Rint = 0.012
phi and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.926, Tmax = 0.945	k = −5→12
6173 measured reflections	l = −16→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.3886P] where P = (Fo2 + 2Fc2)/3
4227 reflections	(Δ/σ)max < 0.001
320 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
S1	0.79625 (6)	0.30246 (6)	0.41198 (4)	0.04987 (15)
S2	0.77232 (6)	0.46456 (5)	0.35447 (3)	0.04581 (14)
O2	0.87236 (18)	0.12722 (17)	0.49915 (11)	0.0596 (4)
O3	0.78833 (18)	0.04135 (19)	0.63321 (12)	0.0653 (4)
O4	0.78550 (16)	0.67278 (14)	0.25767 (10)	0.0518 (3)
O5	0.6376 (2)	0.65050 (16)	0.12387 (11)	0.0703 (5)
H5	0.6937	0.7388	0.1319	0.105*
C12	0.6718 (2)	0.17200 (19)	0.56767 (12)	0.0379 (4)
C13	0.6661 (2)	0.26280 (19)	0.50372 (12)	0.0385 (4)
C14	0.5566 (2)	0.3168 (2)	0.51215 (14)	0.0450 (4)
H14	0.5522	0.3773	0.4705	0.054*
C15	0.4543 (2)	0.2822 (2)	0.58140 (15)	0.0516 (5)
H15	0.3816	0.3192	0.5859	0.062*
C16	0.4590 (2)	0.1929 (2)	0.64402 (15)	0.0523 (5)
H16	0.3897	0.1693	0.6906	0.063*
C17	0.5674 (2)	0.1390 (2)	0.63682 (14)	0.0452 (4)
H17	0.5708	0.0791	0.6793	0.054*
C18	0.7866 (2)	0.1099 (2)	0.56449 (14)	0.0435 (4)
C19	0.5772 (2)	0.44117 (19)	0.19213 (12)	0.0411 (4)
C20	0.6068 (2)	0.36948 (19)	0.26285 (12)	0.0399 (4)
C21	0.5030 (2)	0.2243 (2)	0.26044 (14)	0.0504 (5)
H21	0.5192	0.1761	0.3076	0.060*
C22	0.3767 (3)	0.1507 (2)	0.18949 (16)	0.0577 (5)
H22	0.3083	0.0542	0.1899	0.069*
C23	0.3508 (3)	0.2184 (2)	0.11810 (16)	0.0591 (5)
H23	0.2675	0.1673	0.0690	0.071*
C24	0.4498 (3)	0.3629 (2)	0.12028 (14)	0.0537 (5)
H24	0.4314	0.4095	0.0728	0.064*
C25	0.6773 (2)	0.5980 (2)	0.19429 (13)	0.0432 (4)
O1	0.7722 (2)	−0.07506 (15)	0.13515 (11)	0.0708 (5)
N1	1.0500 (2)	0.28242 (17)	0.21502 (13)	0.0522 (4)
N2	0.9294 (2)	0.17231 (17)	0.14899 (12)	0.0544 (4)
N3	0.95999 (18)	−0.01942 (17)	0.33782 (11)	0.0420 (4)
H3A	1.0521	−0.0163	0.3517	0.063*
H3B	0.8939	−0.1104	0.3082	0.063*
H3C	0.9266	0.0071	0.3936	0.063*
C1	0.8789 (2)	0.0433 (2)	0.18279 (14)	0.0479 (5)
C2	0.9719 (2)	0.07944 (19)	0.27335 (13)	0.0381 (4)
C3	1.0727 (2)	0.2242 (2)	0.29096 (14)	0.0451 (4)
C4	1.1063 (3)	0.4359 (2)	0.2109 (2)	0.0746 (7)
H4A	1.0228	0.4630	0.2147	0.112*
H4B	1.1488	0.4519	0.1499	0.112*
H4C	1.1847	0.4947	0.2654	0.112*
C5	0.8733 (2)	0.1957 (2)	0.05991 (14)	0.0473 (5)
C6	0.9637 (3)	0.2291 (3)	−0.01490 (19)	0.0736 (7)
H6	1.0623	0.2347	−0.0089	0.088*
C7	0.9072 (4)	0.2545 (3)	−0.09933 (19)	0.0868 (9)
H7	0.9685	0.2780	−0.1501	0.104*
C8	0.7649 (4)	0.2455 (3)	−0.10844 (19)	0.0796 (8)
H8	0.7295	0.2661	−0.1646	0.096*
C9	0.6711 (4)	0.2065 (3)	−0.0363 (2)	0.0816 (8)
H9	0.5709	0.1966	−0.0449	0.098*
C10	0.7251 (3)	0.1817 (3)	0.04980 (17)	0.0643 (6)
H10	0.6623	0.1562	0.0996	0.077*
C11	1.1906 (3)	0.3128 (3)	0.37761 (18)	0.0691 (6)
H11A	1.2875	0.3677	0.3551	0.104*
H11B	1.2017	0.2486	0.4169	0.104*
H11C	1.1586	0.3793	0.4168	0.104*

	U11	U22	U33	U12	U13	U23
S1	0.0581 (3)	0.0600 (3)	0.0518 (3)	0.0376 (3)	0.0180 (2)	0.0287 (2)
S2	0.0526 (3)	0.0423 (3)	0.0456 (3)	0.0208 (2)	0.0031 (2)	0.0176 (2)
O2	0.0725 (10)	0.0751 (10)	0.0613 (9)	0.0521 (8)	0.0246 (8)	0.0331 (8)
O3	0.0657 (9)	0.0869 (11)	0.0742 (10)	0.0483 (9)	0.0208 (8)	0.0522 (9)
O4	0.0579 (8)	0.0390 (7)	0.0534 (8)	0.0144 (6)	−0.0025 (7)	0.0175 (6)
O5	0.1014 (13)	0.0418 (8)	0.0523 (8)	0.0151 (8)	−0.0180 (8)	0.0205 (7)
C12	0.0403 (9)	0.0369 (9)	0.0357 (9)	0.0164 (8)	−0.0008 (7)	0.0082 (7)
C13	0.0435 (9)	0.0384 (9)	0.0352 (9)	0.0197 (8)	0.0010 (7)	0.0081 (7)
C14	0.0530 (11)	0.0489 (11)	0.0423 (10)	0.0299 (9)	0.0030 (8)	0.0128 (8)
C15	0.0510 (11)	0.0622 (13)	0.0517 (11)	0.0343 (10)	0.0082 (9)	0.0115 (10)
C16	0.0507 (11)	0.0627 (13)	0.0483 (11)	0.0273 (10)	0.0135 (9)	0.0159 (10)
C17	0.0496 (11)	0.0457 (10)	0.0424 (10)	0.0204 (9)	0.0045 (8)	0.0158 (8)
C18	0.0467 (10)	0.0448 (10)	0.0442 (10)	0.0230 (9)	0.0022 (8)	0.0148 (8)
C19	0.0538 (11)	0.0369 (9)	0.0336 (9)	0.0197 (8)	0.0073 (8)	0.0099 (7)
C20	0.0527 (10)	0.0356 (9)	0.0341 (9)	0.0210 (8)	0.0085 (8)	0.0092 (7)
C21	0.0682 (13)	0.0366 (10)	0.0459 (10)	0.0204 (9)	0.0075 (9)	0.0143 (8)
C22	0.0692 (14)	0.0354 (10)	0.0555 (12)	0.0116 (10)	0.0069 (10)	0.0074 (9)
C23	0.0633 (13)	0.0485 (12)	0.0496 (12)	0.0130 (10)	−0.0064 (10)	0.0035 (10)
C24	0.0676 (13)	0.0500 (12)	0.0406 (10)	0.0222 (10)	−0.0005 (9)	0.0134 (9)
C25	0.0579 (12)	0.0404 (10)	0.0343 (9)	0.0219 (9)	0.0082 (9)	0.0136 (8)
O1	0.0899 (11)	0.0384 (8)	0.0604 (9)	0.0052 (8)	−0.0302 (8)	0.0196 (7)
N1	0.0551 (10)	0.0353 (8)	0.0576 (10)	0.0109 (7)	−0.0019 (8)	0.0138 (7)
N2	0.0644 (11)	0.0375 (9)	0.0512 (9)	0.0111 (8)	−0.0097 (8)	0.0177 (7)
N3	0.0460 (8)	0.0442 (8)	0.0392 (8)	0.0217 (7)	0.0008 (6)	0.0134 (7)
C1	0.0586 (12)	0.0371 (10)	0.0438 (10)	0.0152 (9)	−0.0030 (9)	0.0153 (8)
C2	0.0412 (9)	0.0383 (9)	0.0375 (9)	0.0188 (8)	0.0030 (7)	0.0110 (7)
C3	0.0457 (10)	0.0430 (10)	0.0463 (10)	0.0194 (9)	0.0020 (8)	0.0096 (8)
C4	0.0852 (17)	0.0384 (12)	0.0888 (18)	0.0133 (11)	0.0020 (14)	0.0231 (12)
C5	0.0616 (12)	0.0379 (10)	0.0455 (10)	0.0216 (9)	0.0034 (9)	0.0175 (8)
C6	0.0665 (15)	0.0874 (18)	0.0727 (16)	0.0297 (13)	0.0191 (12)	0.0403 (14)
C7	0.104 (2)	0.086 (2)	0.0589 (15)	0.0217 (17)	0.0183 (15)	0.0382 (14)
C8	0.119 (2)	0.0490 (13)	0.0605 (15)	0.0255 (14)	−0.0183 (15)	0.0213 (11)
C9	0.094 (2)	0.0870 (19)	0.0804 (18)	0.0587 (17)	−0.0129 (15)	0.0139 (15)
C10	0.0746 (15)	0.0760 (16)	0.0574 (13)	0.0460 (13)	0.0114 (11)	0.0161 (11)
C11	0.0650 (14)	0.0538 (13)	0.0676 (15)	0.0113 (11)	−0.0175 (12)	0.0049 (11)

S1—C13	1.7901 (19)	O1—C1	1.260 (2)
S1—S2	2.0580 (9)	N1—C3	1.350 (2)
S2—C20	1.796 (2)	N1—N2	1.387 (2)
O2—C18	1.231 (2)	N1—C4	1.446 (3)
O3—C18	1.280 (2)	N2—C1	1.376 (2)
O4—C25	1.214 (2)	N2—C5	1.427 (2)
O5—C25	1.311 (2)	N3—C2	1.435 (2)
O5—H5	0.8200	N3—H3A	0.8900
C12—C17	1.390 (3)	N3—H3B	0.8900
C12—C13	1.407 (2)	N3—H3C	0.8900
C12—C18	1.496 (3)	C1—C2	1.412 (3)
C13—C14	1.389 (3)	C2—C3	1.359 (3)
C14—C15	1.379 (3)	C3—C11	1.487 (3)
C14—H14	0.9300	C4—H4A	0.9600
C15—C16	1.378 (3)	C4—H4B	0.9600
C15—H15	0.9300	C4—H4C	0.9600
C16—C17	1.377 (3)	C5—C6	1.370 (3)
C16—H16	0.9300	C5—C10	1.377 (3)
C17—H17	0.9300	C6—C7	1.383 (4)
C19—C24	1.396 (3)	C6—H6	0.9300
C19—C20	1.410 (2)	C7—C8	1.337 (4)
C19—C25	1.479 (3)	C7—H7	0.9300
C20—C21	1.393 (3)	C8—C9	1.365 (4)
C21—C22	1.379 (3)	C8—H8	0.9300
C21—H21	0.9300	C9—C10	1.390 (3)
C22—C23	1.375 (3)	C9—H9	0.9300
C22—H22	0.9300	C10—H10	0.9300
C23—C24	1.376 (3)	C11—H11A	0.9600
C23—H23	0.9300	C11—H11B	0.9600
C24—H24	0.9300	C11—H11C	0.9600
C13—S1—S2	105.53 (6)	C1—N2—N1	109.44 (15)
C20—S2—S1	105.13 (6)	C1—N2—C5	127.62 (16)
C25—O5—H5	109.5	N1—N2—C5	122.93 (15)
C17—C12—C13	118.95 (17)	C2—N3—H3A	109.5
C17—C12—C18	118.54 (16)	C2—N3—H3B	109.5
C13—C12—C18	122.51 (16)	H3A—N3—H3B	109.5
C14—C13—C12	118.82 (16)	C2—N3—H3C	109.5
C14—C13—S1	121.61 (14)	H3A—N3—H3C	109.5
C12—C13—S1	119.55 (13)	H3B—N3—H3C	109.5
C15—C14—C13	121.01 (17)	O1—C1—N2	122.29 (17)
C15—C14—H14	119.5	O1—C1—C2	132.74 (17)
C13—C14—H14	119.5	N2—C1—C2	104.97 (16)
C16—C15—C14	120.43 (18)	C3—C2—C1	109.02 (16)
C16—C15—H15	119.8	C3—C2—N3	125.26 (16)
C14—C15—H15	119.8	C1—C2—N3	125.71 (16)
C17—C16—C15	119.23 (18)	N1—C3—C2	108.82 (16)
C17—C16—H16	120.4	N1—C3—C11	122.47 (18)
C15—C16—H16	120.4	C2—C3—C11	128.71 (18)
C16—C17—C12	121.57 (18)	N1—C4—H4A	109.5
C16—C17—H17	119.2	N1—C4—H4B	109.5
C12—C17—H17	119.2	H4A—C4—H4B	109.5
O2—C18—O3	124.23 (18)	N1—C4—H4C	109.5
O2—C18—C12	120.14 (16)	H4A—C4—H4C	109.5
O3—C18—C12	115.62 (17)	H4B—C4—H4C	109.5
C24—C19—C20	119.15 (17)	C6—C5—C10	120.4 (2)
C24—C19—C25	119.83 (16)	C6—C5—N2	121.0 (2)
C20—C19—C25	121.01 (16)	C10—C5—N2	118.60 (19)
C21—C20—C19	118.20 (17)	C5—C6—C7	119.6 (3)
C21—C20—S2	121.18 (14)	C5—C6—H6	120.2
C19—C20—S2	120.61 (14)	C7—C6—H6	120.2
C22—C21—C20	121.23 (18)	C8—C7—C6	120.4 (3)
C22—C21—H21	119.4	C8—C7—H7	119.8
C20—C21—H21	119.4	C6—C7—H7	119.8
C23—C22—C21	120.71 (19)	C7—C8—C9	120.8 (2)
C23—C22—H22	119.6	C7—C8—H8	119.6
C21—C22—H22	119.6	C9—C8—H8	119.6
C22—C23—C24	119.10 (19)	C8—C9—C10	120.1 (3)
C22—C23—H23	120.4	C8—C9—H9	119.9
C24—C23—H23	120.4	C10—C9—H9	119.9
C23—C24—C19	121.53 (19)	C5—C10—C9	118.6 (2)
C23—C24—H24	119.2	C5—C10—H10	120.7
C19—C24—H24	119.2	C9—C10—H10	120.7
O4—C25—O5	122.76 (17)	C3—C11—H11A	109.5
O4—C25—C19	122.53 (16)	C3—C11—H11B	109.5
O5—C25—C19	114.70 (17)	H11A—C11—H11B	109.5
C3—N1—N2	107.74 (15)	C3—C11—H11C	109.5
C3—N1—C4	128.07 (19)	H11A—C11—H11C	109.5
N2—N1—C4	122.29 (18)	H11B—C11—H11C	109.5
C13—S1—S2—C20	−83.01 (9)	C20—C19—C25—O5	179.46 (17)
C17—C12—C13—C14	0.2 (3)	C3—N1—N2—C1	−1.6 (2)
C18—C12—C13—C14	−179.47 (17)	C4—N1—N2—C1	−167.0 (2)
C17—C12—C13—S1	−178.34 (13)	C3—N1—N2—C5	179.52 (19)
C18—C12—C13—S1	2.0 (2)	C4—N1—N2—C5	14.1 (3)
S2—S1—C13—C14	11.17 (17)	N1—N2—C1—O1	−178.3 (2)
S2—S1—C13—C12	−170.30 (13)	C5—N2—C1—O1	0.6 (4)
C12—C13—C14—C15	−0.3 (3)	N1—N2—C1—C2	1.1 (2)
S1—C13—C14—C15	178.23 (15)	C5—N2—C1—C2	179.9 (2)
C13—C14—C15—C16	0.1 (3)	O1—C1—C2—C3	179.0 (2)
C14—C15—C16—C17	0.2 (3)	N2—C1—C2—C3	−0.2 (2)
C15—C16—C17—C12	−0.3 (3)	O1—C1—C2—N3	−2.3 (4)
C13—C12—C17—C16	0.0 (3)	N2—C1—C2—N3	178.49 (17)
C18—C12—C17—C16	179.76 (18)	N2—N1—C3—C2	1.4 (2)
C17—C12—C18—O2	174.18 (18)	C4—N1—C3—C2	165.8 (2)
C13—C12—C18—O2	−6.1 (3)	N2—N1—C3—C11	−177.9 (2)
C17—C12—C18—O3	−6.3 (3)	C4—N1—C3—C11	−13.6 (3)
C13—C12—C18—O3	173.36 (17)	C1—C2—C3—N1	−0.8 (2)
C24—C19—C20—C21	−2.7 (3)	N3—C2—C3—N1	−179.45 (17)
C25—C19—C20—C21	176.19 (17)	C1—C2—C3—C11	178.5 (2)
C24—C19—C20—S2	178.30 (15)	N3—C2—C3—C11	−0.2 (3)
C25—C19—C20—S2	−2.9 (2)	C1—N2—C5—C6	−113.0 (3)
S1—S2—C20—C21	16.17 (17)	N1—N2—C5—C6	65.7 (3)
S1—S2—C20—C19	−164.81 (13)	C1—N2—C5—C10	66.0 (3)
C19—C20—C21—C22	1.6 (3)	N1—N2—C5—C10	−115.3 (2)
S2—C20—C21—C22	−179.32 (16)	C10—C5—C6—C7	2.5 (4)
C20—C21—C22—C23	0.8 (3)	N2—C5—C6—C7	−178.5 (2)
C21—C22—C23—C24	−2.3 (4)	C5—C6—C7—C8	−0.5 (4)
C22—C23—C24—C19	1.2 (3)	C6—C7—C8—C9	−2.2 (4)
C20—C19—C24—C23	1.3 (3)	C7—C8—C9—C10	2.8 (4)
C25—C19—C24—C23	−177.6 (2)	C6—C5—C10—C9	−1.9 (4)
C24—C19—C25—O4	176.68 (19)	N2—C5—C10—C9	179.1 (2)
C20—C19—C25—O4	−2.2 (3)	C8—C9—C10—C5	−0.7 (4)
C24—C19—C25—O5	−1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1i	0.82	1.72	2.527 (2)	166
N3—H3A···O3ii	0.89	1.68	2.561 (2)	170
N3—H3B···O4iii	0.89	2.00	2.865 (2)	165
N3—H3C···O2	0.89	1.98	2.834 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1i	0.82	1.72	2.527 (2)	166
N3—H3A⋯O3ii	0.89	1.68	2.561 (2)	170
N3—H3B⋯O4iii	0.89	2.00	2.865 (2)	165
N3—H3C⋯O2	0.89	1.98	2.834 (2)	161

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