The desoxazoline asidiacyclamide analogue cyclo(Gly-Thr-D-Val-Thz-Ile-Thr-D-Val-Thz) acetonitrile monosolvate.

THE TITLE PEPTIDE [SYSTEMATIC NAME: 4-(butan-2-yl)-7,20-bis-(1-hy-droxy-eth-yl)-10,23-bis-(propan-2-yl)-12,25-dithia-3,6,9,16,19,22,27,28-octa-aza-tricyclo-[22.2.1.1(11,14)]octa-cosa-1(26),11(28),13,24(27)-tetra-ene-2,5,8,15,18,21-hexone acetonitrile monosolvate], C(32)H(48)N(8)O(8)S(2)·CH(3)CN, an analogue of ascidiacyclamide (ASC) [cyclo(-Ile-Oxz-D-Val-Thz-)(2)], lies about a twofold rotation axis, so that the glycine (Gly) and isoleucine (Ile) residues are each disordered over two sites with equal occupancies. The acetonitrile mol-ecule is also located on a twofold axis passing through the C and N atoms. In the peptide, the thia-zole rings are faced to each other with a dihedral angle of 9.63 (15)° and intra-molecular N-H⋯O and O-H⋯O hydrogen bonds are observed. A bifurcated N-H⋯(O,O) hydrogen bond links the peptide mol-ecules into a layer parallel to the ab plane.

Related literature

For general background to ascidiacyclamide, see: Hamamoto et al. (1983 ▶); Shioiri et al. (1987 ▶); Ishida et al. (1988 ▶); Degnan et al. (1989 ▶); Doi et al. (1999 ▶); Haberhauer & Rominger (2003 ▶). For related structures, see: Schmitz et al. (1989 ▶); n class="Chemical">Asano, Doi et al. (2001 ▶); Asano, Taniguchi et al. (2001 ▶); Asano et al. (2002 ▶, 2003 ▶, 2005 ▶).

Experimental

Crystal data

C32H48N8O8S2·C2H3N

M = 777.96

Orthorhombic,

a = 18.2019 (9) Å

b = 10.4667 (5) Å

c = 11.0695 (6) Å

V = 2108.89 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 200 K

0.40 × 0.40 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.909, T max = 0.982

24275 measured reflections

4669 independent reflections

4359 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.213

S = 1.09

4669 reflections

269 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −1.42 e Å−3

Absolute structure: Flack (1983 ▶), 2016 Friedel pairs

Flack parameter: 0.11 (13)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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 datablock(s) global, I. DOI: 10.1107/S1600536811051543/is5015sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051543/is5015Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051543/is5015Isup3.mol

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

C32H48N8O8S2·C2H3N	F(000) = 828
Mr = 777.96	Dx = 1.225 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 8940 reflections
a = 18.2019 (9) Å	θ = 2.2–25.5°
b = 10.4667 (5) Å	µ = 0.18 mm−1
c = 11.0695 (6) Å	T = 200 K
V = 2108.89 (18) Å3	Plate, colourless
Z = 2	0.40 × 0.40 × 0.10 mm

Bruker SMART APEX CCD area-detector diffractometer	4669 independent reflections
Radiation source: MacScience, M18XCE rotating anode	4359 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 8.366 pixels mm-1	θmax = 27.1°, θmin = 1.8°
ω–scan	h = −23→23
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.909, Tmax = 0.982	l = −14→14
24275 measured reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.1468P)2 + 0.6849P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.075	(Δ/σ)max = 0.017
wR(F2) = 0.213	Δρmax = 0.92 e Å−3
S = 1.09	Δρmin = −1.42 e Å−3
4669 reflections	Absolute structure: Flack (1983), 2016 Friedel pairs
269 parameters	Flack parameter: 0.11 (13)
0 restraints

Geometry. Thz-Thz plane angle = 9.54 °, S(Thz)···S(Thz) = 4.303 A (mercury)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5000	0.5000	0.2003 (14)	0.108 (3)
C2	0.5000	0.5000	0.3182 (14)	0.130 (4)
H2A	0.4497	0.5116	0.3477	0.195*	0.50
H2B	0.5309	0.5700	0.3477	0.195*	0.50
H2C	0.5194	0.4184	0.3477	0.195*	0.50
N1	0.5000	0.5000	0.0925 (9)	0.107 (3)
N11	0.51634 (15)	0.8447 (3)	0.0697 (3)	0.0418 (6)
H11	0.4732	0.8769	0.0505	0.050*
C11	0.572 (3)	0.812 (4)	−0.024 (4)	0.045 (6)	0.50
H11A	0.5480	0.8033	−0.1035	0.054*	0.50
H11B	0.5956	0.7293	−0.0035	0.054*	0.50
C11'	0.564 (2)	0.827 (5)	−0.038 (4)	0.044 (6)	0.50
H11C	0.5836	0.7382	−0.0345	0.053*	0.50
C12'	0.5197 (4)	0.8380 (9)	−0.1579 (7)	0.0539 (18)	0.50
H12	0.4950	0.9233	−0.1568	0.065*	0.50
C13'	0.5723 (5)	0.8385 (12)	−0.2662 (7)	0.070 (2)	0.50
H13A	0.6090	0.9060	−0.2554	0.106*	0.50
H13B	0.5444	0.8543	−0.3404	0.106*	0.50
H13C	0.5970	0.7555	−0.2718	0.106*	0.50
C14'	0.4574 (6)	0.7354 (11)	−0.1663 (12)	0.081 (3)	0.50
H14A	0.4481	0.6952	−0.0868	0.097*	0.50
H14B	0.4111	0.7733	−0.1966	0.097*	0.50
C15'	0.4887 (8)	0.6390 (16)	−0.2562 (14)	0.116 (5)	0.50
H15A	0.4527	0.5710	−0.2701	0.174*	0.50
H15B	0.5339	0.6020	−0.2234	0.174*	0.50
H15C	0.4995	0.6822	−0.3327	0.174*	0.50
C16	0.62923 (19)	0.9158 (3)	−0.0285 (3)	0.0467 (8)
O16	0.61582 (14)	1.0319 (3)	−0.0393 (2)	0.0525 (6)
N21	0.69723 (16)	0.8697 (3)	−0.0161 (3)	0.0505 (7)
H21	0.7022	0.7861	−0.0176	0.061*
C21	0.76449 (19)	0.9454 (4)	0.0001 (3)	0.0482 (8)
H21A	0.8056	0.8822	0.0049	0.058*
C22	0.7838 (2)	1.0347 (4)	−0.1057 (3)	0.0564 (9)
H22A	0.8356	1.0632	−0.0929	0.068*
O22	0.73999 (17)	1.1466 (3)	−0.1100 (3)	0.0661 (8)
H22	0.6964	1.1278	−0.0921	0.099*
C23	0.7822 (3)	0.9632 (6)	−0.2260 (4)	0.0814 (15)
H23A	0.7948	1.0222	−0.2916	0.122*
H23B	0.7329	0.9285	−0.2397	0.122*
H23C	0.8179	0.8932	−0.2240	0.122*
C24	0.76604 (19)	1.0189 (4)	0.1201 (3)	0.0459 (7)
O24	0.80873 (17)	1.1097 (3)	0.1328 (2)	0.0615 (7)
N31	0.27760 (14)	1.0230 (3)	0.2096 (2)	0.0403 (6)
H31	0.3012	1.0958	0.2006	0.048*
C31	0.28693 (17)	0.9514 (3)	0.3208 (3)	0.0390 (6)
H31A	0.2578	0.8710	0.3114	0.047*
C32	0.2561 (2)	1.0205 (4)	0.4338 (3)	0.0504 (8)
H32	0.2707	0.9700	0.5066	0.061*
C33	0.2876 (3)	1.1554 (5)	0.4473 (4)	0.0688 (12)
H33A	0.3413	1.1509	0.4503	0.103*
H33B	0.2691	1.1939	0.5221	0.103*
H33C	0.2724	1.2076	0.3782	0.103*
C34	0.1722 (3)	1.0227 (7)	0.4279 (5)	0.0808 (16)
H34A	0.1537	0.9354	0.4181	0.121*
H34B	0.1565	1.0749	0.3591	0.121*
H34C	0.1526	1.0593	0.5028	0.121*
C43	0.36703 (17)	0.9114 (3)	0.3314 (3)	0.0377 (6)
N41	0.40907 (14)	0.8932 (2)	0.2387 (2)	0.0380 (5)
C41	0.47758 (17)	0.8488 (3)	0.2747 (3)	0.0396 (6)
C42	0.4862 (2)	0.8312 (3)	0.3948 (3)	0.0457 (7)
H42	0.5295	0.8002	0.4325	0.055*
S42	0.40690 (5)	0.87335 (9)	0.46931 (7)	0.0496 (3)
C44	0.53543 (17)	0.8225 (3)	0.1831 (3)	0.0406 (7)
O44	0.59620 (14)	0.7815 (2)	0.2133 (2)	0.0506 (6)

	U11	U22	U33	U12	U13	U23
C1	0.114 (7)	0.077 (6)	0.133 (10)	−0.045 (5)	0.000	0.000
C2	0.148 (11)	0.073 (6)	0.168 (13)	0.009 (6)	0.000	0.000
N1	0.116 (6)	0.098 (5)	0.106 (6)	−0.056 (5)	0.000	0.000
N11	0.0380 (13)	0.0362 (13)	0.0512 (14)	−0.0033 (10)	0.0115 (11)	−0.0055 (11)
C11	0.052 (15)	0.038 (10)	0.044 (7)	−0.010 (8)	0.007 (7)	−0.014 (7)
C11'	0.033 (5)	0.044 (11)	0.056 (13)	−0.003 (6)	0.010 (7)	−0.010 (7)
C12'	0.038 (3)	0.066 (5)	0.058 (4)	0.000 (3)	0.001 (3)	−0.015 (4)
C13'	0.061 (4)	0.108 (7)	0.042 (4)	0.002 (5)	0.002 (3)	−0.020 (4)
C14'	0.072 (6)	0.079 (6)	0.092 (8)	−0.014 (5)	0.003 (5)	−0.019 (6)
C15'	0.098 (9)	0.125 (11)	0.125 (10)	−0.022 (9)	−0.025 (8)	−0.055 (10)
C16	0.0473 (17)	0.0529 (18)	0.0400 (15)	−0.0156 (15)	0.0093 (14)	−0.0128 (14)
O16	0.0527 (13)	0.0491 (13)	0.0558 (14)	−0.0133 (11)	0.0054 (11)	0.0011 (11)
N21	0.0476 (15)	0.0455 (15)	0.0582 (16)	−0.0079 (12)	0.0158 (13)	−0.0106 (14)
C21	0.0416 (16)	0.0538 (18)	0.0493 (19)	−0.0067 (14)	0.0093 (13)	−0.0060 (15)
C22	0.0501 (18)	0.074 (2)	0.0449 (18)	−0.0171 (19)	0.0121 (15)	−0.0031 (17)
O22	0.0568 (15)	0.0703 (18)	0.0714 (18)	−0.0174 (14)	0.0051 (13)	0.0133 (15)
C23	0.084 (3)	0.112 (4)	0.048 (2)	−0.028 (3)	0.016 (2)	−0.011 (3)
C24	0.0427 (16)	0.0491 (17)	0.0461 (17)	−0.0031 (14)	0.0028 (13)	0.0028 (14)
O24	0.0681 (16)	0.0656 (17)	0.0508 (13)	−0.0296 (14)	0.0026 (13)	−0.0035 (13)
N31	0.0395 (12)	0.0372 (12)	0.0444 (13)	−0.0020 (11)	−0.0003 (11)	−0.0003 (10)
C31	0.0369 (14)	0.0423 (15)	0.0378 (14)	−0.0009 (12)	0.0027 (11)	−0.0025 (12)
C32	0.0476 (17)	0.061 (2)	0.0428 (16)	0.0097 (16)	0.0065 (14)	−0.0050 (15)
C33	0.081 (3)	0.063 (2)	0.062 (2)	0.006 (2)	0.014 (2)	−0.026 (2)
C34	0.053 (2)	0.118 (4)	0.071 (3)	0.021 (3)	0.009 (2)	−0.022 (3)
C43	0.0417 (15)	0.0330 (13)	0.0383 (14)	0.0008 (11)	0.0043 (12)	0.0015 (11)
N41	0.0410 (12)	0.0297 (10)	0.0432 (12)	0.0017 (10)	0.0068 (11)	0.0010 (10)
C41	0.0384 (14)	0.0285 (12)	0.0518 (17)	0.0003 (11)	0.0065 (13)	0.0025 (12)
C42	0.0450 (17)	0.0422 (16)	0.0499 (18)	0.0029 (14)	0.0035 (14)	0.0072 (14)
S42	0.0482 (4)	0.0615 (5)	0.0391 (4)	0.0057 (4)	0.0043 (3)	0.0082 (4)
C44	0.0408 (15)	0.0242 (11)	0.0568 (18)	−0.0015 (11)	0.0103 (14)	−0.0020 (12)
O44	0.0434 (12)	0.0416 (11)	0.0669 (16)	0.0063 (10)	0.0086 (12)	0.0024 (11)

C1—N1	1.193 (15)	C21—H21A	1.0000
C1—C2	1.305 (19)	C22—O22	1.417 (6)
C2—H2A	0.9800	C22—C23	1.528 (6)
C2—H2B	0.9800	C22—H22A	1.0000
C2—H2C	0.9800	O22—H22	0.84
N11—C44	1.324 (5)	C23—H23A	0.9800
N11—C11'	1.49 (4)	C23—H23B	0.9800
N11—C11	1.49 (5)	C23—H23C	0.9800
N11—H11	0.8800	C24—O24	1.236 (5)
C11—C16	1.51 (5)	C24—N31i	1.344 (4)
C11—H11A	0.9900	N31—C24i	1.344 (4)
C11—H11B	0.9900	N31—C31	1.451 (4)
C11'—C16	1.51 (5)	N31—H31	0.8800
C11'—C12'	1.55 (4)	C31—C43	1.521 (4)
C11'—H11C	1.0000	C31—C32	1.550 (4)
C12'—C13'	1.534 (11)	C31—H31A	1.0000
C12'—C14'	1.565 (13)	C32—C34	1.529 (6)
C12'—H12	1.0000	C32—C33	1.531 (6)
C13'—H13A	0.9800	C32—H32	1.0000
C13'—H13B	0.9800	C33—H33A	0.9800
C13'—H13C	0.9800	C33—H33B	0.9800
C14'—C15'	1.527 (18)	C33—H33C	0.9800
C14'—H14A	0.9900	C34—H34A	0.9800
C14'—H14B	0.9900	C34—H34B	0.9800
C15'—H15A	0.9800	C34—H34C	0.9800
C15'—H15B	0.9800	C43—N41	1.294 (4)
C15'—H15C	0.9800	C43—S42	1.736 (3)
C16—O16	1.245 (5)	N41—C41	1.389 (4)
C16—N21	1.336 (5)	C41—C42	1.351 (5)
N21—C21	1.469 (4)	C41—C44	1.487 (4)
N21—H21	0.8800	C42—S42	1.719 (4)
C21—C24	1.535 (5)	C42—H42	0.9500
C21—C22	1.538 (5)	C44—O44	1.233 (4)
N1—C1—C2	180.000 (3)	C24—C21—H21A	105.8
C1—C2—H2A	109.5	C22—C21—H21A	105.8
C1—C2—H2B	109.5	O22—C22—C23	111.4 (4)
H2A—C2—H2B	109.5	O22—C22—C21	113.5 (3)
C1—C2—H2C	109.5	C23—C22—C21	111.2 (4)
H2A—C2—H2C	109.5	O22—C22—H22A	106.7
H2B—C2—H2C	109.5	C23—C22—H22A	106.7
C44—N11—C11'	126.0 (16)	C21—C22—H22A	106.7
C44—N11—C11	116.1 (17)	C22—O22—H22	109
C44—N11—H11	122.0	C22—C23—H23A	109.5
C11'—N11—H11	111.9	C22—C23—H23B	109.5
C11—N11—H11	122.0	H23A—C23—H23B	109.5
N11—C11—C16	109 (3)	C22—C23—H23C	109.5
N11—C11—H11A	109.8	H23A—C23—H23C	109.5
C16—C11—H11A	109.8	H23B—C23—H23C	109.5
N11—C11—H11B	109.8	O24—C24—N31i	122.6 (3)
C16—C11—H11B	109.8	O24—C24—C21	119.7 (3)
H11A—C11—H11B	108.3	N31i—C24—C21	117.6 (3)
N11—C11'—C16	109 (3)	C24i—N31—C31	121.7 (3)
N11—C11'—C12'	112 (3)	C24i—N31—H31	119.1
C16—C11'—C12'	115 (3)	C31—N31—H31	119.1
N11—C11'—H11C	106.7	N31—C31—C43	108.7 (2)
C16—C11'—H11C	106.7	N31—C31—C32	113.6 (3)
C12'—C11'—H11C	106.7	C43—C31—C32	114.4 (3)
C13'—C12'—C11'	110.0 (18)	N31—C31—H31A	106.5
C13'—C12'—C14'	114.1 (8)	C43—C31—H31A	106.5
C11'—C12'—C14'	112.2 (19)	C32—C31—H31A	106.5
C13'—C12'—H12	106.7	C34—C32—C33	111.3 (4)
C11'—C12'—H12	106.7	C34—C32—C31	109.6 (3)
C14'—C12'—H12	106.7	C33—C32—C31	111.9 (3)
C12'—C13'—H13A	109.5	C34—C32—H32	108.0
C12'—C13'—H13B	109.5	C33—C32—H32	108.0
H13A—C13'—H13B	109.5	C31—C32—H32	108.0
C12'—C13'—H13C	109.5	C32—C33—H33A	109.5
H13A—C13'—H13C	109.5	C32—C33—H33B	109.5
H13B—C13'—H13C	109.5	H33A—C33—H33B	109.5
C15'—C14'—C12'	102.8 (9)	C32—C33—H33C	109.5
C15'—C14'—H14A	111.2	H33A—C33—H33C	109.5
C12'—C14'—H14A	111.2	H33B—C33—H33C	109.5
C15'—C14'—H14B	111.2	C32—C34—H34A	109.5
C12'—C14'—H14B	111.2	C32—C34—H34B	109.5
H14A—C14'—H14B	109.1	H34A—C34—H34B	109.5
C14'—C15'—H15A	109.5	C32—C34—H34C	109.5
C14'—C15'—H15B	109.5	H34A—C34—H34C	109.5
H15A—C15'—H15B	109.5	H34B—C34—H34C	109.5
C14'—C15'—H15C	109.5	N41—C43—C31	123.1 (3)
H15A—C15'—H15C	109.5	N41—C43—S42	114.6 (2)
H15B—C15'—H15C	109.5	C31—C43—S42	122.1 (2)
O16—C16—N21	123.0 (3)	C43—N41—C41	110.6 (3)
O16—C16—C11	124.9 (17)	C42—C41—N41	115.6 (3)
N21—C16—C11	112.1 (17)	C42—C41—C44	124.3 (3)
O16—C16—C11'	115.9 (18)	N41—C41—C44	120.1 (3)
N21—C16—C11'	121.0 (18)	C41—C42—S42	109.9 (3)
C16—N21—C21	126.2 (3)	C41—C42—H42	125.1
C16—N21—H21	116.9	S42—C42—H42	125.1
C21—N21—H21	116.9	C42—S42—C43	89.31 (16)
N21—C21—C24	113.0 (3)	O44—C44—N11	123.6 (3)
N21—C21—C22	115.1 (3)	O44—C44—C41	121.0 (3)
C24—C21—C22	110.5 (3)	N11—C44—C41	115.4 (3)
N21—C21—H21A	105.8
C44—N11—C11—C16	−79 (3)	C22—C21—C24—O24	−31.0 (5)
C11'—N11—C11—C16	83 (20)	N21—C21—C24—N31i	21.2 (5)
C44—N11—C11'—C16	−62 (3)	C22—C21—C24—N31i	151.9 (3)
C11—N11—C11'—C16	−82 (19)	C24i—N31—C31—C43	117.0 (3)
C44—N11—C11'—C12'	169.4 (14)	C24i—N31—C31—C32	−114.4 (4)
C11—N11—C11'—C12'	149 (22)	N31—C31—C32—C34	70.0 (5)
N11—C11'—C12'—C13'	172 (2)	C43—C31—C32—C34	−164.4 (4)
C16—C11'—C12'—C13'	47 (3)	N31—C31—C32—C33	−54.0 (4)
N11—C11'—C12'—C14'	−60 (3)	C43—C31—C32—C33	71.6 (4)
C16—C11'—C12'—C14'	175 (2)	N31—C31—C43—N41	−27.9 (4)
C13'—C12'—C14'—C15'	21.2 (13)	C32—C31—C43—N41	−156.0 (3)
C11'—C12'—C14'—C15'	−105 (2)	N31—C31—C43—S42	157.8 (2)
N11—C11—C16—O16	−52 (3)	C32—C31—C43—S42	29.6 (4)
N11—C11—C16—N21	126 (2)	C31—C43—N41—C41	−175.8 (3)
N11—C11—C16—C11'	−83 (19)	S42—C43—N41—C41	−1.0 (3)
N11—C11'—C16—O16	−69 (3)	C43—N41—C41—C42	1.3 (4)
C12'—C11'—C16—O16	57 (3)	C43—N41—C41—C44	−179.3 (3)
N11—C11'—C16—N21	114 (2)	N41—C41—C42—S42	−0.9 (4)
C12'—C11'—C16—N21	−119 (2)	C44—C41—C42—S42	179.7 (2)
N11—C11'—C16—C11	82 (18)	C41—C42—S42—C43	0.3 (3)
C12'—C11'—C16—C11	−151 (21)	N41—C43—S42—C42	0.4 (3)
O16—C16—N21—C21	7.0 (6)	C31—C43—S42—C42	175.2 (3)
C11—C16—N21—C21	−171.0 (18)	C11'—N11—C44—O44	−1(2)
C11'—C16—N21—C21	−176.9 (19)	C11—N11—C44—O44	3(2)
C16—N21—C21—C24	65.8 (5)	C11'—N11—C44—C41	179 (2)
C16—N21—C21—C22	−62.5 (5)	C11—N11—C44—C41	−177 (2)
N21—C21—C22—O22	76.3 (4)	C42—C41—C44—O44	0.3 (5)
C24—C21—C22—O22	−53.2 (4)	N41—C41—C44—O44	−179.1 (3)
N21—C21—C22—C23	−50.3 (5)	C42—C41—C44—N11	179.5 (3)
C24—C21—C22—C23	−179.8 (4)	N41—C41—C44—N11	0.1 (4)
N21—C21—C24—O24	−161.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O22—H22···O16	0.84	1.87	2.674 (4)	160
N11—H11···O16i	0.88	2.12	2.984 (3)	166
N21—H21···O22ii	0.88	2.29	2.953 (4)	132
N21—H21···O24ii	0.88	2.25	3.013 (4)	145
N31—H31···O44i	0.88	2.27	3.074 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O22—H22⋯O16	0.84	1.87	2.674 (4)	160
N11—H11⋯O16i	0.88	2.12	2.984 (3)	166
N21—H21⋯O22ii	0.88	2.29	2.953 (4)	132
N21—H21⋯O24ii	0.88	2.25	3.013 (4)	145
N31—H31⋯O44i	0.88	2.27	3.074 (3)	152

Symmetry codes: (i) ; (ii) .