l-Lysinium trifluoro-acetate.

Ions of the title compound, C(6)H(15)N(2)O(2) (+)·C(2)F(3)O(2) (-), a new organic nonlinear optical crystal, are linked by N-H⋯O hydrogen-bonding inter-actions. Both the amino groups of the l-lysinium cation are protonated. A three-dimensional network of hydrogen bonds is observed, forming a closed ring. Inter-molecular N-H⋯O hydrogen bonds involving l-lysinium cations and trifluoro-acetate anions link the ions into extended chains which run parallel to the [010] direction. The F atoms of the trifluoro-acetate anion are disordered over two sites with site occupancies of 0.423 (18) and 0.577 (18). The asymmetric unit consists of two cations and two anions.

Related literature

For related literature, see: Babu, Sethuraman, Gopalakrishnan & Ramasamy (2006 ▶); Babu, Sethuraman, Vijayan et al. (2006 ▶); Chandra et al. (1998 ▶); Debrus et al. (2005 ▶); Drozd & Marchewka (2006 ▶); Kurtz & Perry (1968 ▶); Marchewka et al. (2003 ▶); Prasad & Vijayan (1993 ▶); Pratap et al. (2000 ▶); Suresh et al. (1994 ▶); Xu et al. (1983 ▶); Yokotani et al. (1989 ▶).

Experimental

Crystal data

C6H15N2O2 +·C2F3O2 −

M = 260.22

Monoclinic,

a = 5.6985 (2) Å

b = 23.5430 (8) Å

c = 8.5007 (3) Å

β = 91.630 (2)°

V = 1139.99 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 293 (2) K

0.35 × 0.29 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.95, T max = 0.98

8405 measured reflections

2674 independent reflections

2470 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.06

2674 reflections

340 parameters

43 restraints

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2000 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068791/gw2034sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068791/gw2034Isup2.hkl

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

C6H15N2O2+·C2F3O2–	F000 = 544
Mr = 260.22	Dx = 1.516 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3919 reflections
a = 5.6985 (2) Å	θ = 3.0–27.3º
b = 23.5430 (8) Å	µ = 0.15 mm−1
c = 8.5007 (3) Å	T = 293 (2) K
β = 91.630 (2)º	Prism, colourless
V = 1139.99 (7) Å3	0.35 × 0.29 × 0.12 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2674 independent reflections
Radiation source: fine-focus sealed tube	2470 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 293(2) K	θmax = 27.5º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(APEX2; Bruker, 2005)	h = −5→7
Tmin = 0.95, Tmax = 0.98	k = −30→25
8405 measured reflections	l = −11→10

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0705P)2 + 0.3205P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2674 reflections	Δρmax = 0.44 e Å−3
340 parameters	Δρmin = −0.23 e Å−3
43 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (4)

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	Occ. (<1)
C1	0.2035 (7)	0.19654 (15)	0.9377 (4)	0.0386 (7)
H1A	0.0417	0.2088	0.9236	0.046*
H1B	0.2078	0.1557	0.9233	0.046*
C2	0.3517 (7)	0.22473 (15)	0.8138 (4)	0.0394 (8)
H2A	0.2868	0.2149	0.7106	0.047*
H2B	0.5091	0.2091	0.8218	0.047*
C3	0.3684 (6)	0.28929 (15)	0.8256 (4)	0.0340 (7)
H3A	0.4339	0.2994	0.9284	0.041*
H3B	0.4753	0.3029	0.7473	0.041*
C4	0.1328 (6)	0.31898 (14)	0.8015 (4)	0.0320 (7)
H4A	0.0210	0.3020	0.8715	0.038*
H4B	0.0763	0.3124	0.6944	0.038*
C5	0.1405 (5)	0.38324 (12)	0.8314 (3)	0.0260 (6)
H5	0.1926	0.3898	0.9408	0.031*
C6	−0.1062 (5)	0.40846 (13)	0.8071 (4)	0.0274 (6)
C7	0.8434 (7)	0.56316 (15)	0.4189 (4)	0.0417 (8)
H7A	1.0015	0.5512	0.3955	0.050*
H7B	0.8324	0.6036	0.3988	0.050*
C8	0.6728 (7)	0.53266 (16)	0.3112 (4)	0.0415 (8)
H8A	0.7097	0.5418	0.2034	0.050*
H8B	0.5164	0.5470	0.3296	0.050*
C9	0.6694 (6)	0.46783 (15)	0.3289 (4)	0.0348 (7)
H9A	0.6187	0.4584	0.4337	0.042*
H9B	0.5552	0.4522	0.2540	0.042*
C10	0.9055 (6)	0.44005 (14)	0.3031 (4)	0.0337 (7)
H10A	1.0215	0.4572	0.3741	0.040*
H10B	0.9523	0.4478	0.1964	0.040*
C11	0.9066 (5)	0.37617 (13)	0.3288 (3)	0.0266 (6)
H11	0.8574	0.3684	0.4362	0.032*
C12	1.1556 (5)	0.35209 (13)	0.3097 (4)	0.0278 (6)
C13	0.2120 (7)	0.5547 (2)	0.9656 (5)	0.0490 (9)
C14	0.3551 (6)	0.56626 (15)	0.8184 (5)	0.0399 (8)
C15	0.1624 (6)	0.69327 (14)	0.6885 (4)	0.0332 (7)
C16	0.3002 (6)	0.69936 (14)	0.5366 (4)	0.0463 (9)
F1	0.2737 (7)	0.50496 (14)	1.0285 (4)	0.0803 (10)
F2	−0.0167 (5)	0.5514 (2)	0.9324 (3)	0.0847 (11)
F3	0.2391 (8)	0.59289 (17)	1.0789 (4)	0.0907 (12)
N1	0.3086 (4)	0.41146 (12)	0.7262 (3)	0.0286 (5)
H1C	0.4547	0.4054	0.7622	0.043*
H1D	0.2802	0.4486	0.7238	0.043*
H1E	0.2917	0.3973	0.6295	0.043*
N2	0.2873 (5)	0.21051 (13)	1.0996 (3)	0.0344 (6)
H2C	0.4418	0.2052	1.1077	0.052*
H2D	0.2162	0.1881	1.1678	0.052*
H2E	0.2544	0.2466	1.1204	0.052*
N3	0.7381 (4)	0.34760 (12)	0.2158 (3)	0.0299 (5)
H3C	0.5918	0.3535	0.2461	0.045*
H3D	0.7672	0.3105	0.2144	0.045*
H3E	0.7550	0.3619	0.1199	0.045*
N4	0.8017 (6)	0.55253 (14)	0.5879 (4)	0.0403 (7)
H4C	0.6511	0.5587	0.6072	0.060*
H4D	0.8906	0.5759	0.6465	0.060*
H4E	0.8383	0.5167	0.6113	0.060*
O1	0.3110 (5)	0.53384 (12)	0.7075 (4)	0.0461 (6)
O2	0.4978 (6)	0.60529 (15)	0.8282 (5)	0.0703 (10)
O3	0.0036 (5)	0.65772 (12)	0.6844 (4)	0.0475 (7)
O4	0.2218 (5)	0.72643 (11)	0.7963 (3)	0.0406 (6)
O5	1.3033 (4)	0.36431 (13)	0.4147 (3)	0.0441 (6)
O6	1.1940 (4)	0.32512 (12)	0.1873 (3)	0.0418 (6)
O7	−0.1433 (4)	0.43812 (12)	0.6875 (3)	0.0411 (6)
O8	−0.2560 (4)	0.39525 (12)	0.9057 (3)	0.0401 (6)
F4	0.240 (3)	0.6636 (6)	0.4230 (12)	0.090 (4)	0.423 (18)
F5	0.5288 (10)	0.6952 (6)	0.5549 (13)	0.069 (3)	0.423 (18)
F6	0.263 (2)	0.7512 (4)	0.4766 (16)	0.084 (3)	0.423 (18)
F4'	0.3461 (18)	0.6491 (2)	0.4707 (10)	0.078 (2)	0.577 (18)
F5'	0.5098 (11)	0.7221 (5)	0.5632 (9)	0.074 (2)	0.577 (18)
F6'	0.1885 (16)	0.7293 (6)	0.4287 (9)	0.092 (3)	0.577 (18)

	U11	U22	U33	U12	U13	U23
C1	0.049 (2)	0.0265 (16)	0.0408 (18)	−0.0012 (14)	0.0043 (15)	0.0011 (14)
C2	0.054 (2)	0.0284 (17)	0.0366 (17)	0.0102 (15)	0.0107 (15)	0.0013 (13)
C3	0.0359 (17)	0.0298 (16)	0.0368 (16)	0.0041 (13)	0.0077 (13)	0.0052 (13)
C4	0.0374 (17)	0.0214 (14)	0.0371 (16)	−0.0017 (12)	−0.0037 (12)	0.0021 (12)
C5	0.0241 (13)	0.0260 (15)	0.0277 (13)	−0.0013 (10)	−0.0030 (10)	0.0025 (11)
C6	0.0241 (13)	0.0240 (14)	0.0337 (15)	−0.0008 (10)	−0.0033 (11)	−0.0007 (12)
C7	0.054 (2)	0.0270 (17)	0.0443 (19)	−0.0018 (15)	0.0063 (15)	0.0009 (14)
C8	0.056 (2)	0.0327 (18)	0.0352 (17)	0.0103 (16)	−0.0063 (15)	0.0015 (13)
C9	0.0388 (17)	0.0270 (15)	0.0382 (16)	0.0024 (13)	−0.0057 (13)	−0.0033 (13)
C10	0.0402 (17)	0.0253 (16)	0.0358 (16)	−0.0003 (13)	0.0046 (13)	−0.0020 (13)
C11	0.0270 (13)	0.0271 (15)	0.0260 (13)	0.0023 (11)	0.0037 (10)	0.0009 (11)
C12	0.0258 (13)	0.0253 (14)	0.0325 (15)	0.0023 (11)	0.0054 (11)	0.0018 (11)
C13	0.052 (2)	0.050 (2)	0.044 (2)	0.0021 (18)	−0.0073 (16)	−0.0040 (18)
C14	0.0298 (16)	0.0286 (18)	0.061 (2)	0.0016 (13)	−0.0010 (14)	0.0052 (16)
C15	0.0340 (16)	0.0242 (15)	0.0417 (18)	0.0024 (13)	0.0043 (13)	−0.0025 (13)
C16	0.050 (2)	0.050 (2)	0.0390 (19)	−0.0059 (17)	0.0059 (16)	0.0046 (17)
F1	0.111 (3)	0.065 (2)	0.0658 (19)	0.0023 (18)	0.0032 (17)	0.0254 (16)
F2	0.0436 (13)	0.150 (3)	0.0610 (16)	−0.0034 (19)	0.0068 (12)	0.009 (2)
F3	0.116 (3)	0.095 (3)	0.0607 (18)	0.012 (2)	−0.0090 (19)	−0.0309 (19)
N1	0.0241 (11)	0.0268 (13)	0.0349 (13)	0.0002 (10)	−0.0007 (10)	0.0027 (10)
N2	0.0363 (15)	0.0318 (15)	0.0356 (14)	0.0077 (11)	0.0082 (11)	0.0073 (11)
N3	0.0240 (11)	0.0253 (12)	0.0404 (14)	0.0009 (10)	0.0021 (10)	0.0007 (10)
N4	0.0505 (17)	0.0314 (15)	0.0386 (15)	0.0006 (13)	−0.0038 (12)	−0.0031 (12)
O1	0.0524 (15)	0.0326 (14)	0.0534 (16)	0.0008 (11)	0.0057 (12)	0.0023 (12)
O2	0.0528 (18)	0.0406 (17)	0.117 (3)	−0.0165 (14)	0.0025 (19)	0.0017 (19)
O3	0.0430 (14)	0.0419 (15)	0.0583 (16)	−0.0118 (11)	0.0129 (12)	−0.0149 (13)
O4	0.0426 (13)	0.0324 (13)	0.0471 (14)	−0.0041 (10)	0.0063 (11)	−0.0083 (11)
O5	0.0300 (12)	0.0520 (16)	0.0497 (15)	0.0023 (11)	−0.0063 (10)	−0.0119 (12)
O6	0.0397 (13)	0.0486 (15)	0.0372 (12)	0.0141 (11)	0.0048 (10)	−0.0094 (11)
O7	0.0385 (13)	0.0448 (15)	0.0396 (13)	0.0084 (11)	−0.0048 (10)	0.0129 (11)
O8	0.0269 (11)	0.0480 (15)	0.0454 (13)	0.0013 (10)	0.0009 (9)	0.0113 (12)
F4	0.096 (5)	0.103 (6)	0.070 (5)	−0.027 (4)	0.016 (4)	−0.021 (4)
F5	0.055 (4)	0.088 (5)	0.066 (4)	0.017 (3)	0.016 (3)	0.017 (4)
F6	0.102 (5)	0.078 (5)	0.071 (5)	0.002 (4)	0.016 (4)	0.030 (4)
F4'	0.100 (4)	0.075 (3)	0.063 (3)	0.020 (3)	0.037 (3)	−0.010 (3)
F5'	0.061 (3)	0.094 (5)	0.068 (3)	−0.027 (3)	0.023 (2)	−0.007 (3)
F6'	0.095 (4)	0.117 (5)	0.064 (3)	0.023 (4)	−0.004 (3)	0.036 (3)

C1—N2	1.481 (5)	C11—C12	1.541 (4)
C1—C2	1.521 (5)	C11—H11	0.9800
C1—H1A	0.9700	C12—O5	1.243 (4)
C1—H1B	0.9700	C12—O6	1.244 (4)
C2—C3	1.526 (5)	C13—F3	1.324 (5)
C2—H2A	0.9700	C13—F2	1.328 (5)
C2—H2B	0.9700	C13—F1	1.330 (5)
C3—C4	1.522 (5)	C13—C14	1.537 (6)
C3—H3A	0.9700	C14—O2	1.228 (5)
C3—H3B	0.9700	C14—O1	1.234 (5)
C4—C5	1.534 (4)	C15—O3	1.232 (4)
C4—H4A	0.9700	C15—O4	1.243 (4)
C4—H4B	0.9700	C15—C16	1.537 (5)
C5—N1	1.486 (4)	C16—F6'	1.308 (5)
C5—C6	1.535 (4)	C16—F5	1.312 (5)
C5—H5	0.9800	C16—F4	1.319 (5)
C6—O7	1.247 (4)	C16—F5'	1.323 (5)
C6—O8	1.253 (4)	C16—F6	1.337 (5)
C7—N4	1.484 (5)	C16—F4'	1.338 (5)
C7—C8	1.500 (5)	N1—H1C	0.8900
C7—H7A	0.9700	N1—H1D	0.8900
C7—H7B	0.9700	N1—H1E	0.8900
C8—C9	1.534 (5)	N2—H2C	0.8900
C8—H8A	0.9700	N2—H2D	0.8900
C8—H8B	0.9700	N2—H2E	0.8900
C9—C10	1.518 (5)	N3—H3C	0.8900
C9—H9A	0.9700	N3—H3D	0.8900
C9—H9B	0.9700	N3—H3E	0.8900
C10—C11	1.520 (5)	N4—H4C	0.8900
C10—H10A	0.9700	N4—H4D	0.8900
C10—H10B	0.9700	N4—H4E	0.8900
C11—N3	1.498 (4)
N2—C1—C2	112.0 (3)	C12—C11—H11	108.6
N2—C1—H1A	109.2	O5—C12—O6	126.0 (3)
C2—C1—H1A	109.2	O5—C12—C11	116.5 (3)
N2—C1—H1B	109.2	O6—C12—C11	117.4 (3)
C2—C1—H1B	109.2	F3—C13—F2	106.7 (4)
H1A—C1—H1B	107.9	F3—C13—F1	106.3 (4)
C1—C2—C3	115.1 (3)	F2—C13—F1	106.3 (4)
C1—C2—H2A	108.5	F3—C13—C14	114.7 (4)
C3—C2—H2A	108.5	F2—C13—C14	112.2 (3)
C1—C2—H2B	108.5	F1—C13—C14	110.0 (4)
C3—C2—H2B	108.5	O2—C14—O1	129.4 (4)
H2A—C2—H2B	107.5	O2—C14—C13	116.3 (4)
C4—C3—C2	113.3 (3)	O1—C14—C13	114.3 (3)
C4—C3—H3A	108.9	O3—C15—O4	129.2 (3)
C2—C3—H3A	108.9	O3—C15—C16	115.6 (3)
C4—C3—H3B	108.9	O4—C15—C16	115.2 (3)
C2—C3—H3B	108.9	F6'—C16—F5	125.8 (6)
H3A—C3—H3B	107.7	F6'—C16—F4	73.7 (7)
C3—C4—C5	114.2 (3)	F5—C16—F4	106.1 (7)
C3—C4—H4A	108.7	F6'—C16—F5'	108.7 (6)
C5—C4—H4A	108.7	F5—C16—F5'	28.5 (5)
C3—C4—H4B	108.7	F4—C16—F5'	126.8 (6)
C5—C4—H4B	108.7	F6'—C16—F6	34.0 (5)
H4A—C4—H4B	107.6	F5—C16—F6	105.1 (7)
N1—C5—C4	110.9 (2)	F4—C16—F6	105.5 (8)
N1—C5—C6	110.5 (2)	F5'—C16—F6	80.1 (7)
C4—C5—C6	109.7 (2)	F6'—C16—F4'	106.3 (6)
N1—C5—H5	108.6	F5—C16—F4'	77.2 (6)
C4—C5—H5	108.6	F4—C16—F4'	34.9 (6)
C6—C5—H5	108.6	F5'—C16—F4'	104.1 (6)
O7—C6—O8	125.6 (3)	F6—C16—F4'	132.7 (6)
O7—C6—C5	117.4 (3)	F6'—C16—C15	112.9 (4)
O8—C6—C5	116.9 (3)	F5—C16—C15	115.0 (5)
N4—C7—C8	113.0 (3)	F4—C16—C15	115.2 (5)
N4—C7—H7A	109.0	F5'—C16—C15	112.0 (4)
C8—C7—H7A	109.0	F6—C16—C15	109.0 (5)
N4—C7—H7B	109.0	F4'—C16—C15	112.3 (4)
C8—C7—H7B	109.0	C5—N1—H1C	109.5
H7A—C7—H7B	107.8	C5—N1—H1D	109.5
C7—C8—C9	115.2 (3)	H1C—N1—H1D	109.5
C7—C8—H8A	108.5	C5—N1—H1E	109.5
C9—C8—H8A	108.5	H1C—N1—H1E	109.5
C7—C8—H8B	108.5	H1D—N1—H1E	109.5
C9—C8—H8B	108.5	C1—N2—H2C	109.5
H8A—C8—H8B	107.5	C1—N2—H2D	109.5
C10—C9—C8	113.6 (3)	H2C—N2—H2D	109.5
C10—C9—H9A	108.8	C1—N2—H2E	109.5
C8—C9—H9A	108.8	H2C—N2—H2E	109.5
C10—C9—H9B	108.8	H2D—N2—H2E	109.5
C8—C9—H9B	108.8	C11—N3—H3C	109.5
H9A—C9—H9B	107.7	C11—N3—H3D	109.5
C9—C10—C11	113.9 (3)	H3C—N3—H3D	109.5
C9—C10—H10A	108.8	C11—N3—H3E	109.5
C11—C10—H10A	108.8	H3C—N3—H3E	109.5
C9—C10—H10B	108.8	H3D—N3—H3E	109.5
C11—C10—H10B	108.8	C7—N4—H4C	109.5
H10A—C10—H10B	107.7	C7—N4—H4D	109.5
N3—C11—C10	110.6 (3)	H4C—N4—H4D	109.5
N3—C11—C12	110.0 (2)	C7—N4—H4E	109.5
C10—C11—C12	110.4 (3)	H4C—N4—H4E	109.5
N3—C11—H11	108.6	H4D—N4—H4E	109.5
C10—C11—H11	108.6
N2—C1—C2—C3	−56.8 (4)	F3—C13—C14—O2	8.0 (5)
C1—C2—C3—C4	−62.9 (4)	F2—C13—C14—O2	130.0 (4)
C2—C3—C4—C5	173.4 (3)	F1—C13—C14—O2	−111.8 (4)
C3—C4—C5—N1	58.8 (3)	F3—C13—C14—O1	−173.0 (4)
C3—C4—C5—C6	−178.8 (3)	F2—C13—C14—O1	−51.0 (5)
N1—C5—C6—O7	14.6 (4)	F1—C13—C14—O1	67.2 (4)
C4—C5—C6—O7	−108.0 (3)	O3—C15—C16—F6'	78.6 (8)
N1—C5—C6—O8	−168.6 (3)	O4—C15—C16—F6'	−98.9 (8)
C4—C5—C6—O8	68.8 (4)	O3—C15—C16—F5	−127.4 (8)
N4—C7—C8—C9	−58.7 (4)	O4—C15—C16—F5	55.0 (9)
C7—C8—C9—C10	−58.1 (4)	O3—C15—C16—F4	−3.5 (11)
C8—C9—C10—C11	177.0 (3)	O4—C15—C16—F4	178.9 (10)
C9—C10—C11—N3	61.2 (3)	O3—C15—C16—F5'	−158.3 (7)
C9—C10—C11—C12	−176.7 (3)	O4—C15—C16—F5'	24.1 (8)
N3—C11—C12—O5	−167.2 (3)	O3—C15—C16—F6	114.9 (9)
C10—C11—C12—O5	70.4 (4)	O4—C15—C16—F6	−62.7 (9)
N3—C11—C12—O6	16.8 (4)	O3—C15—C16—F4'	−41.6 (7)
C10—C11—C12—O6	−105.6 (3)	O4—C15—C16—F4'	140.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4E···O7i	0.89	1.96	2.838 (4)	168
N4—H4D···O1i	0.89	2.63	3.080 (4)	112
N4—H4D···F2i	0.89	2.54	3.079 (4)	120
N4—H4D···O3i	0.89	2.05	2.842 (4)	147
N3—H3E···O8ii	0.89	1.98	2.866 (4)	172
N3—H3D···O4iii	0.89	1.98	2.864 (4)	171
N3—H3C···O6iv	0.89	2.40	3.148 (4)	142
N3—H3C···O5iv	0.89	2.23	3.064 (4)	157
N2—H2E···O6v	0.89	1.97	2.853 (4)	174
N2—H2D···O3vi	0.89	1.94	2.800 (4)	163
N2—H2C···O4vii	0.89	2.12	2.934 (4)	151
N1—H1E···O5iv	0.89	1.99	2.870 (4)	172
N1—H1C···O7i	0.89	2.52	3.212 (4)	136
N1—H1C···O8i	0.89	2.04	2.901 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4E⋯O7i	0.89	1.96	2.838 (4)	168
N4—H4D⋯O1i	0.89	2.63	3.080 (4)	112
N4—H4D⋯F2i	0.89	2.54	3.079 (4)	120
N4—H4D⋯O3i	0.89	2.05	2.842 (4)	147
N3—H3E⋯O8ii	0.89	1.98	2.866 (4)	172
N3—H3D⋯O4iii	0.89	1.98	2.864 (4)	171
N3—H3C⋯O6iv	0.89	2.40	3.148 (4)	142
N3—H3C⋯O5iv	0.89	2.23	3.064 (4)	157
N2—H2E⋯O6v	0.89	1.97	2.853 (4)	174
N2—H2D⋯O3vi	0.89	1.94	2.800 (4)	163
N2—H2C⋯O4vii	0.89	2.12	2.934 (4)	151
N1—H1E⋯O5iv	0.89	1.99	2.870 (4)	172
N1—H1C⋯O7i	0.89	2.52	3.212 (4)	136
N1—H1C⋯O8i	0.89	2.04	2.901 (4)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .