5-Amino-1-phenyl-3-trifluoro-methyl-1H-pyrazole-4-carboxylic acid.

In the title compound, C(11)H(8)F(3)N(3)O(2), there are two mol-ecules in the asymmetric unit wherein the phenyl rings make dihedral angles of 65.3 (2) and 85.6 (2)° with the pyrazole rings. In the crystal, pairs of mol-ecules are held together by O-H⋯O hydrogen bonds between the carboxyl groups, forming a centrosymmetric dimer with an R(2) (2)(8) motif. Intra-molecular N-H⋯O inter-actions are also present.

Related literature

For general background, see: Caruso & Rossi (2004 ▶); Maggio et al., (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H8F3N3O2

M = 271.20

Monoclinic,

a = 9.757 (3) Å

b = 10.740 (3) Å

c = 21.277 (6) Å

β = 93.716 (3)°

V = 2225 (1) Å3

Z = 8

Mo Kα radiation

μ = 0.15 mm−1

T = 125 K

0.30 × 0.18 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.957, T max = 0.993

20692 measured reflections

3772 independent reflections

2737 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.01

3772 reflections

368 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032188/bx2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032188/bx2218Isup2.hkl

Additional supplementary materials: crystallographic informan class="Chemical">tion; 3D view; checkCIF report

C11H8F3N3O2	F(000) = 1104
Mr = 271.20	Dx = 1.619 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3829 reflections
a = 9.757 (3) Å	θ = 2.2–22.3°
b = 10.740 (3) Å	µ = 0.15 mm−1
c = 21.277 (6) Å	T = 125 K
β = 93.716 (3)°	Flat needle, pale yellow
V = 2225 (1) Å3	0.30 × 0.18 × 0.05 mm
Z = 8

Bruker APEXII CCD diffractometer	3772 independent reflections
Radiation source: fine-focus sealed tube	2737 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 24.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→11
Tmin = 0.957, Tmax = 0.993	k = −12→12
20692 measured reflections	l = −25→24

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0233P)2 + 1.9621P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3772 reflections	Δρmax = 0.43 e Å−3
368 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0099 (12)

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
F1	1.0029 (2)	0.57631 (18)	0.86748 (8)	0.0449 (5)
F2	0.88145 (19)	0.61681 (17)	0.94547 (8)	0.0402 (5)
F3	1.03719 (18)	0.74508 (17)	0.91981 (8)	0.0410 (5)
F51	0.5059 (2)	0.47366 (17)	0.12944 (8)	0.0417 (5)
F52	0.62681 (18)	0.41822 (16)	0.05332 (8)	0.0380 (5)
F53	0.43613 (17)	0.32665 (16)	0.06739 (7)	0.0361 (5)
O1	0.8071 (2)	0.8727 (2)	0.96933 (9)	0.0323 (5)
O2	0.6443 (2)	0.98989 (19)	0.91963 (9)	0.0295 (5)
O51	0.6194 (2)	0.1440 (2)	0.01774 (9)	0.0312 (5)
O52	0.7542 (2)	0.00154 (19)	0.06715 (9)	0.0343 (5)
N1	0.7329 (2)	0.7741 (2)	0.76427 (10)	0.0268 (6)
N2	0.8258 (2)	0.6935 (2)	0.79385 (10)	0.0283 (6)
N3	0.5911 (3)	0.9467 (2)	0.78704 (13)	0.0301 (6)
N51	0.7186 (2)	0.2162 (2)	0.22548 (10)	0.0263 (6)
N52	0.6454 (3)	0.3151 (2)	0.19957 (10)	0.0274 (6)
N53	0.8148 (3)	0.0243 (3)	0.19747 (13)	0.0334 (7)
C1	0.6874 (3)	0.7528 (3)	0.70017 (12)	0.0280 (7)
C2	0.6161 (3)	0.6448 (3)	0.68442 (13)	0.0307 (7)
H2	0.5971	0.5859	0.7160	0.037*
C3	0.5730 (3)	0.6233 (3)	0.62231 (13)	0.0340 (8)
H3	0.5244	0.5491	0.6111	0.041*
C4	0.6001 (3)	0.7086 (3)	0.57672 (14)	0.0385 (8)
H4	0.5702	0.6932	0.5340	0.046*
C5	0.6705 (4)	0.8163 (3)	0.59258 (14)	0.0412 (8)
H5	0.6886	0.8751	0.5608	0.049*
C6	0.7154 (3)	0.8395 (3)	0.65493 (13)	0.0350 (8)
H6	0.7643	0.9135	0.6661	0.042*
C7	0.8382 (3)	0.7328 (3)	0.85250 (13)	0.0269 (7)
C8	0.7540 (3)	0.8365 (3)	0.86272 (12)	0.0258 (7)
C9	0.6881 (3)	0.8604 (3)	0.80423 (12)	0.0253 (6)
C10	0.7303 (3)	0.9061 (3)	0.91922 (13)	0.0265 (7)
C11	0.9388 (3)	0.6684 (3)	0.89644 (14)	0.0333 (7)
C51	0.7711 (3)	0.2189 (3)	0.28986 (12)	0.0258 (7)
C52	0.6897 (3)	0.1791 (3)	0.33664 (13)	0.0303 (7)
H52	0.5997	0.1485	0.3264	0.036*
C53	0.7412 (3)	0.1847 (3)	0.39859 (14)	0.0341 (7)
H53	0.6865	0.1572	0.4313	0.041*
C54	0.8717 (3)	0.2301 (3)	0.41322 (13)	0.0344 (8)
H54	0.9060	0.2352	0.4560	0.041*
C55	0.9524 (3)	0.2681 (3)	0.36596 (14)	0.0343 (7)
H55	1.0429	0.2976	0.3761	0.041*
C56	0.9021 (3)	0.2632 (3)	0.30386 (14)	0.0319 (7)
H56	0.9570	0.2901	0.2712	0.038*
C57	0.6225 (3)	0.2847 (3)	0.13997 (12)	0.0253 (6)
C58	0.6793 (3)	0.1676 (3)	0.12543 (12)	0.0256 (7)
C59	0.7408 (3)	0.1272 (3)	0.18279 (12)	0.0262 (7)
C60	0.6867 (3)	0.0985 (3)	0.06813 (13)	0.0277 (7)
C61	0.5484 (3)	0.3755 (3)	0.09757 (13)	0.0286 (7)
H1	0.792 (4)	0.918 (4)	1.004 (2)	0.076 (14)*
H30	0.597 (4)	0.987 (4)	0.748 (2)	0.066 (12)*
H31	0.579 (4)	1.000 (3)	0.8190 (17)	0.047 (10)*
H51	0.628 (4)	0.087 (4)	−0.0156 (19)	0.067 (12)*
H530	0.830 (3)	0.001 (3)	0.2381 (17)	0.041 (9)*
H531	0.807 (4)	−0.029 (3)	0.1682 (18)	0.047 (11)*

	U11	U22	U33	U12	U13	U23
F1	0.0527 (12)	0.0511 (12)	0.0302 (10)	0.0212 (10)	−0.0019 (8)	−0.0080 (8)
F2	0.0541 (12)	0.0421 (11)	0.0240 (9)	0.0044 (9)	0.0002 (8)	0.0061 (8)
F3	0.0383 (11)	0.0534 (12)	0.0302 (10)	−0.0014 (9)	−0.0061 (8)	−0.0047 (8)
F51	0.0600 (12)	0.0355 (11)	0.0290 (10)	0.0142 (9)	−0.0017 (9)	−0.0026 (8)
F52	0.0473 (11)	0.0392 (11)	0.0280 (9)	−0.0021 (9)	0.0055 (8)	0.0098 (8)
F53	0.0368 (10)	0.0450 (11)	0.0255 (9)	0.0005 (8)	−0.0054 (8)	0.0025 (8)
O1	0.0468 (13)	0.0355 (13)	0.0141 (10)	0.0050 (10)	−0.0018 (9)	−0.0034 (9)
O2	0.0381 (12)	0.0312 (12)	0.0191 (10)	0.0040 (10)	0.0009 (8)	−0.0016 (8)
O51	0.0446 (13)	0.0341 (12)	0.0145 (10)	0.0059 (10)	−0.0013 (9)	−0.0016 (9)
O52	0.0547 (14)	0.0304 (12)	0.0171 (10)	0.0095 (11)	−0.0016 (9)	−0.0027 (8)
N1	0.0323 (14)	0.0339 (14)	0.0140 (11)	0.0015 (11)	−0.0012 (10)	−0.0020 (10)
N2	0.0310 (14)	0.0353 (15)	0.0184 (12)	0.0013 (11)	−0.0004 (10)	−0.0021 (10)
N3	0.0386 (15)	0.0329 (15)	0.0187 (13)	0.0037 (12)	0.0008 (11)	−0.0015 (12)
N51	0.0364 (14)	0.0264 (13)	0.0158 (12)	0.0009 (11)	−0.0012 (10)	−0.0018 (10)
N52	0.0363 (14)	0.0285 (14)	0.0169 (12)	0.0022 (11)	−0.0016 (10)	−0.0004 (10)
N53	0.0501 (17)	0.0324 (16)	0.0170 (14)	0.0067 (13)	−0.0026 (12)	−0.0009 (12)
C1	0.0320 (16)	0.0357 (18)	0.0162 (14)	0.0050 (14)	0.0012 (12)	−0.0017 (12)
C2	0.0316 (16)	0.0389 (19)	0.0212 (15)	0.0045 (14)	−0.0010 (12)	−0.0017 (13)
C3	0.0328 (17)	0.042 (2)	0.0268 (16)	0.0037 (15)	−0.0016 (13)	−0.0096 (14)
C4	0.0422 (19)	0.051 (2)	0.0219 (16)	0.0123 (16)	−0.0039 (14)	−0.0082 (15)
C5	0.052 (2)	0.050 (2)	0.0224 (16)	0.0114 (17)	0.0047 (14)	0.0059 (15)
C6	0.0403 (18)	0.0407 (19)	0.0243 (16)	0.0009 (15)	0.0036 (13)	−0.0014 (14)
C7	0.0329 (16)	0.0304 (17)	0.0172 (14)	−0.0030 (13)	0.0007 (12)	0.0010 (12)
C8	0.0346 (16)	0.0274 (16)	0.0153 (14)	−0.0040 (13)	0.0015 (12)	−0.0009 (12)
C9	0.0300 (16)	0.0262 (16)	0.0200 (14)	−0.0032 (13)	0.0029 (12)	−0.0019 (12)
C10	0.0352 (17)	0.0258 (16)	0.0183 (14)	−0.0067 (14)	0.0000 (12)	0.0012 (12)
C11	0.0389 (18)	0.0370 (18)	0.0236 (16)	0.0012 (15)	−0.0002 (13)	−0.0021 (14)
C51	0.0333 (16)	0.0267 (16)	0.0169 (14)	0.0001 (13)	−0.0028 (12)	−0.0021 (12)
C52	0.0317 (16)	0.0367 (18)	0.0227 (15)	0.0003 (14)	0.0030 (12)	0.0007 (13)
C53	0.0415 (19)	0.0408 (19)	0.0205 (15)	0.0057 (15)	0.0055 (13)	0.0016 (13)
C54	0.0443 (19)	0.0393 (19)	0.0185 (15)	0.0069 (15)	−0.0074 (13)	−0.0042 (13)
C55	0.0364 (18)	0.0350 (19)	0.0307 (17)	−0.0008 (14)	−0.0047 (14)	−0.0044 (14)
C56	0.0370 (18)	0.0348 (18)	0.0242 (16)	−0.0050 (14)	0.0049 (13)	−0.0027 (13)
C57	0.0336 (16)	0.0254 (16)	0.0168 (14)	−0.0027 (13)	0.0006 (12)	−0.0002 (12)
C58	0.0360 (17)	0.0243 (16)	0.0164 (14)	−0.0035 (13)	0.0021 (12)	−0.0008 (11)
C59	0.0318 (16)	0.0280 (17)	0.0191 (14)	−0.0014 (13)	0.0036 (12)	−0.0015 (12)
C60	0.0362 (17)	0.0297 (18)	0.0170 (15)	−0.0045 (14)	0.0001 (12)	−0.0013 (12)
C61	0.0359 (17)	0.0289 (17)	0.0209 (15)	0.0004 (13)	0.0015 (13)	−0.0048 (12)

F1—C11	1.341 (3)	C2—C3	1.380 (4)
F2—C11	1.336 (3)	C2—H2	0.9500
F3—C11	1.336 (4)	C3—C4	1.372 (5)
F51—C61	1.335 (3)	C3—H3	0.9500
F52—C61	1.333 (3)	C4—C5	1.376 (5)
F53—C61	1.340 (3)	C4—H4	0.9500
O1—C10	1.313 (3)	C5—C6	1.392 (4)
O1—H1	0.91 (4)	C5—H5	0.9500
O2—C10	1.231 (3)	C6—H6	0.9500
O51—C60	1.315 (3)	C7—C8	1.410 (4)
O51—H51	0.94 (4)	C7—C11	1.482 (4)
O52—C60	1.232 (4)	C8—C9	1.387 (4)
N1—C9	1.350 (4)	C8—C10	1.447 (4)
N1—N2	1.376 (3)	C51—C56	1.379 (4)
N1—C1	1.425 (3)	C51—C52	1.380 (4)
N2—C7	1.316 (4)	C52—C53	1.381 (4)
N3—C9	1.358 (4)	C52—H52	0.9500
N3—H30	0.95 (4)	C53—C54	1.381 (5)
N3—H31	0.90 (4)	C53—H53	0.9500
N51—C59	1.346 (4)	C54—C55	1.378 (4)
N51—N52	1.376 (3)	C54—H54	0.9500
N51—C51	1.431 (3)	C55—C56	1.380 (4)
N52—C57	1.315 (3)	C55—H55	0.9500
N53—C59	1.346 (4)	C56—H56	0.9500
N53—H530	0.90 (3)	C57—C58	1.416 (4)
N53—H531	0.85 (4)	C57—C61	1.484 (4)
C1—C6	1.379 (4)	C58—C59	1.393 (4)
C1—C2	1.383 (4)	C58—C60	1.433 (4)
C10—O1—H1	114 (3)	O2—C10—C8	121.9 (3)
C60—O51—H51	108 (2)	O1—C10—C8	114.9 (3)
C9—N1—N2	112.0 (2)	F2—C11—F3	107.0 (2)
C9—N1—C1	128.2 (2)	F2—C11—F1	106.6 (2)
N2—N1—C1	119.5 (2)	F3—C11—F1	106.3 (2)
C7—N2—N1	104.4 (2)	F2—C11—C7	113.1 (3)
C9—N3—H30	118 (2)	F3—C11—C7	112.2 (3)
C9—N3—H31	110 (2)	F1—C11—C7	111.3 (2)
H30—N3—H31	114 (3)	C56—C51—C52	121.3 (3)
C59—N51—N52	112.3 (2)	C56—C51—N51	118.9 (3)
C59—N51—C51	126.7 (2)	C52—C51—N51	119.8 (3)
N52—N51—C51	120.8 (2)	C51—C52—C53	119.0 (3)
C57—N52—N51	104.2 (2)	C51—C52—H52	120.5
C59—N53—H530	120 (2)	C53—C52—H52	120.5
C59—N53—H531	111 (2)	C54—C53—C52	120.2 (3)
H530—N53—H531	121 (3)	C54—C53—H53	119.9
C6—C1—C2	121.1 (3)	C52—C53—H53	119.9
C6—C1—N1	119.8 (3)	C55—C54—C53	120.2 (3)
C2—C1—N1	119.1 (3)	C55—C54—H54	119.9
C3—C2—C1	119.3 (3)	C53—C54—H54	119.9
C3—C2—H2	120.3	C54—C55—C56	120.2 (3)
C1—C2—H2	120.3	C54—C55—H55	119.9
C4—C3—C2	120.3 (3)	C56—C55—H55	119.9
C4—C3—H3	119.9	C51—C56—C55	119.2 (3)
C2—C3—H3	119.9	C51—C56—H56	120.4
C3—C4—C5	120.3 (3)	C55—C56—H56	120.4
C3—C4—H4	119.9	N52—C57—C58	112.8 (2)
C5—C4—H4	119.9	N52—C57—C61	117.9 (2)
C4—C5—C6	120.3 (3)	C58—C57—C61	129.2 (2)
C4—C5—H5	119.8	C59—C58—C57	103.7 (2)
C6—C5—H5	119.8	C59—C58—C60	122.8 (3)
C1—C6—C5	118.7 (3)	C57—C58—C60	133.5 (3)
C1—C6—H6	120.6	N51—C59—N53	122.3 (3)
C5—C6—H6	120.6	N51—C59—C58	107.0 (2)
N2—C7—C8	112.4 (2)	N53—C59—C58	130.7 (3)
N2—C7—C11	117.7 (3)	O52—C60—O51	122.6 (3)
C8—C7—C11	129.8 (3)	O52—C60—C58	120.5 (3)
C9—C8—C7	104.4 (2)	O51—C60—C58	116.8 (3)
C9—C8—C10	124.1 (3)	F52—C61—F51	107.4 (2)
C7—C8—C10	131.5 (3)	F52—C61—F53	106.6 (2)
N1—C9—N3	123.2 (3)	F51—C61—F53	106.3 (2)
N1—C9—C8	106.7 (2)	F52—C61—C57	112.1 (2)
N3—C9—C8	130.0 (3)	F51—C61—C57	111.5 (2)
O2—C10—O1	123.2 (3)	F53—C61—C57	112.7 (2)
C9—N1—N2—C7	−0.7 (3)	N2—C7—C11—F1	−0.1 (4)
C1—N1—N2—C7	−175.4 (2)	C8—C7—C11—F1	−177.2 (3)
C59—N51—N52—C57	0.2 (3)	C59—N51—C51—C56	83.1 (4)
C51—N51—N52—C57	175.8 (2)	N52—N51—C51—C56	−91.7 (3)
C9—N1—C1—C6	69.0 (4)	C59—N51—C51—C52	−97.9 (4)
N2—N1—C1—C6	−117.2 (3)	N52—N51—C51—C52	87.3 (3)
C9—N1—C1—C2	−111.3 (3)	C56—C51—C52—C53	0.3 (5)
N2—N1—C1—C2	62.5 (4)	N51—C51—C52—C53	−178.7 (3)
C6—C1—C2—C3	0.3 (4)	C51—C52—C53—C54	0.4 (5)
N1—C1—C2—C3	−179.4 (3)	C52—C53—C54—C55	−1.2 (5)
C1—C2—C3—C4	−0.3 (4)	C53—C54—C55—C56	1.3 (5)
C2—C3—C4—C5	0.0 (5)	C52—C51—C56—C55	−0.1 (5)
C3—C4—C5—C6	0.3 (5)	N51—C51—C56—C55	178.9 (3)
C2—C1—C6—C5	0.0 (5)	C54—C55—C56—C51	−0.6 (5)
N1—C1—C6—C5	179.6 (3)	N51—N52—C57—C58	−0.2 (3)
C4—C5—C6—C1	−0.3 (5)	N51—N52—C57—C61	−177.9 (2)
N1—N2—C7—C8	0.9 (3)	N52—C57—C58—C59	0.1 (3)
N1—N2—C7—C11	−176.6 (2)	C61—C57—C58—C59	177.5 (3)
N2—C7—C8—C9	−0.8 (3)	N52—C57—C58—C60	−176.8 (3)
C11—C7—C8—C9	176.3 (3)	C61—C57—C58—C60	0.6 (5)
N2—C7—C8—C10	177.1 (3)	N52—N51—C59—N53	177.5 (3)
C11—C7—C8—C10	−5.7 (5)	C51—N51—C59—N53	2.2 (5)
N2—N1—C9—N3	−176.8 (3)	N52—N51—C59—C58	−0.2 (3)
C1—N1—C9—N3	−2.6 (5)	C51—N51—C59—C58	−175.4 (3)
N2—N1—C9—C8	0.2 (3)	C57—C58—C59—N51	0.1 (3)
C1—N1—C9—C8	174.3 (3)	C60—C58—C59—N51	177.4 (3)
C7—C8—C9—N1	0.4 (3)	C57—C58—C59—N53	−177.3 (3)
C10—C8—C9—N1	−177.8 (3)	C60—C58—C59—N53	0.0 (5)
C7—C8—C9—N3	177.0 (3)	C59—C58—C60—O52	−3.2 (5)
C10—C8—C9—N3	−1.1 (5)	C57—C58—C60—O52	173.2 (3)
C9—C8—C10—O2	2.9 (5)	C59—C58—C60—O51	177.1 (3)
C7—C8—C10—O2	−174.7 (3)	C57—C58—C60—O51	−6.4 (5)
C9—C8—C10—O1	−177.2 (3)	N52—C57—C61—F52	115.3 (3)
C7—C8—C10—O1	5.2 (5)	C58—C57—C61—F52	−62.0 (4)
N2—C7—C11—F2	−120.1 (3)	N52—C57—C61—F51	−5.1 (4)
C8—C7—C11—F2	62.9 (4)	C58—C57—C61—F51	177.6 (3)
N2—C7—C11—F3	118.8 (3)	N52—C57—C61—F53	−124.5 (3)
C8—C7—C11—F3	−58.2 (4)	C58—C57—C61—F53	58.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N53—H531···O52	0.85 (4)	2.20 (4)	2.808 (3)	128 (3)
O51—H51···O2i	0.94 (4)	1.75 (4)	2.687 (3)	177 (4)
N3—H31···O2	0.90 (4)	2.20 (4)	2.873 (3)	132 (3)
O1—H1···O52ii	0.91 (4)	1.67 (4)	2.580 (3)	176 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N53—H531⋯O52	0.85 (4)	2.20 (4)	2.808 (3)	128 (3)
O51—H51⋯O2i	0.94 (4)	1.75 (4)	2.687 (3)	177 (4)
N3—H31⋯O2	0.90 (4)	2.20 (4)	2.873 (3)	132 (3)
O1—H1⋯O52ii	0.91 (4)	1.67 (4)	2.580 (3)	176 (4)

Symmetry codes: (i) ; (ii) .