2,4,5-Trichloro-anilinium perchlorate 18-crown-6 clathrate.

In the title compound, C(6)H(5)Cl(3)N(+)·ClO(4) (-)·C(12)H(24)O(6), the perchlorate anion is disordered over two orientations in a 0.666 (17):0.334 (17) ratio. The ammonium group of the organic cation inserts into the crown ether ring and forms three bifurcated N-H⋯(O,O) hydrogen bonds to generate a supra-molecular complex. The macrocycle has approximate D(3d) local symmetry.

Related literature

For background to mol­ecular ferroelectric materials, see: Fu et al. (2011 ▶).

Experimental

Crystal data

C6H5Cl3N+·ClO4 −·C12H24O6

M = 561.22

Triclinic,

a = 9.4961 (19) Å

b = 11.783 (2) Å

c = 11.852 (2) Å

α = 97.86 (3)°

β = 90.39 (3)°

γ = 105.26 (3)°

V = 1266.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.52 mm−1

T = 298 K

0.10 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 (2 × 2 bin mode) diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

11310 measured reflections

4713 independent reflections

3562 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.152

S = 1.03

4713 reflections

346 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006162/hb6625sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006162/hb6625Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006162/hb6625Isup3.cml

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

C6H5Cl3N+·ClO4−·C12H24O6	Z = 2
Mr = 561.22	F(000) = 584
Triclinic, P1	Dx = 1.472 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4961 (19) Å	Cell parameters from 4713 reflections
b = 11.783 (2) Å	θ = 3.1–26.5°
c = 11.852 (2) Å	µ = 0.52 mm−1
α = 97.86 (3)°	T = 298 K
β = 90.39 (3)°	Block, colourless
γ = 105.26 (3)°	0.10 × 0.05 × 0.05 mm
V = 1266.1 (4) Å3

Rigaku Mercury2 (2x2 bin mode) diffractometer	4713 independent reflections
Radiation source: fine-focus sealed tube	3562 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 13.6612 pixels mm-1	θmax = 25.5°, θmin = 3.1°
CCD profile fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.910, Tmax = 1.000	l = −14→14
11310 measured reflections

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.070P)2 + 0.575P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4713 reflections	Δρmax = 0.57 e Å−3
346 parameters	Δρmin = −0.28 e Å−3
18 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: 0.019 (2)

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)
Cl1	0.30933 (8)	0.67394 (7)	0.38541 (7)	0.0584 (3)
N1	0.5852 (2)	0.7317 (2)	0.25875 (17)	0.0421 (5)
H1C	0.6761	0.7384	0.2370	0.063*
H1D	0.5358	0.7570	0.2078	0.063*
H1E	0.5417	0.6559	0.2637	0.063*
Cl2	0.60060 (12)	1.00366 (8)	0.72283 (6)	0.0763 (3)
C18	0.5882 (3)	0.8037 (2)	0.3703 (2)	0.0366 (6)
Cl3	0.86985 (10)	1.06897 (8)	0.56512 (8)	0.0800 (3)
C13	0.4666 (3)	0.7804 (2)	0.4375 (2)	0.0408 (6)
C15	0.5973 (4)	0.9285 (3)	0.5859 (2)	0.0492 (7)
C16	0.7156 (3)	0.9555 (3)	0.5175 (2)	0.0489 (7)
O3	0.5578 (2)	0.53489 (19)	0.78658 (19)	0.0616 (6)
O1	0.1138 (2)	0.2827 (2)	0.7236 (2)	0.0636 (6)
C17	0.7111 (3)	0.8924 (2)	0.4094 (2)	0.0458 (6)
H17A	0.7908	0.9100	0.3635	0.055*
C14	0.4716 (3)	0.8432 (2)	0.5456 (2)	0.0467 (7)
H14A	0.3908	0.8279	0.5906	0.056*
O2	0.3401 (3)	0.43429 (19)	0.61331 (18)	0.0643 (6)
O4	0.6757 (3)	0.3898 (2)	0.90636 (19)	0.0747 (7)
O6	0.2005 (3)	0.1902 (2)	0.9069 (2)	0.0697 (6)
O5	0.4919 (3)	0.1617 (2)	0.93064 (19)	0.0773 (7)
C1	0.0241 (4)	0.2633 (4)	0.8172 (3)	0.0762 (11)
H1A	−0.0777	0.2451	0.7919	0.091*
H1B	0.0459	0.3346	0.8730	0.091*
C9	0.5364 (5)	0.5924 (3)	0.6920 (3)	0.0813 (12)
H9A	0.5927	0.5699	0.6289	0.098*
H9B	0.5691	0.6780	0.7131	0.098*
C10	0.3801 (5)	0.5564 (3)	0.6579 (3)	0.0776 (11)
H10A	0.3230	0.5705	0.7234	0.093*
H10B	0.3611	0.6027	0.6007	0.093*
C6	0.6873 (5)	0.3373 (4)	1.0053 (3)	0.0837 (12)
H6A	0.6265	0.3631	1.0634	0.100*
H6B	0.7877	0.3616	1.0352	0.100*
C8	0.7075 (4)	0.5679 (3)	0.8253 (4)	0.0799 (11)
H8A	0.7437	0.6538	0.8398	0.096*
H8B	0.7656	0.5379	0.7674	0.096*
C7	0.7188 (4)	0.5178 (4)	0.9294 (4)	0.0877 (13)
H7A	0.8187	0.5450	0.9605	0.105*
H7B	0.6565	0.5448	0.9856	0.105*
C2	0.0499 (4)	0.1641 (4)	0.8693 (3)	0.0841 (13)
H2A	−0.0118	0.1507	0.9337	0.101*
H2B	0.0249	0.0922	0.8142	0.101*
C3	0.2348 (6)	0.1026 (4)	0.9654 (4)	0.0952 (14)
H3A	0.2244	0.0297	0.9131	0.114*
H3B	0.1678	0.0855	1.0261	0.114*
C11	0.1938 (5)	0.3922 (4)	0.5702 (4)	0.0843 (12)
H11A	0.1828	0.3183	0.5193	0.101*
H11B	0.1721	0.4495	0.5261	0.101*
C12	0.0878 (4)	0.3719 (4)	0.6604 (4)	0.0899 (13)
H12A	0.0972	0.4455	0.7115	0.108*
H12B	−0.0107	0.3460	0.6265	0.108*
C5	0.6391 (5)	0.2059 (4)	0.9751 (3)	0.0909 (13)
H5A	0.7031	0.1814	0.9190	0.109*
H5B	0.6493	0.1700	1.0426	0.109*
C4	0.3898 (7)	0.1477 (5)	1.0147 (4)	0.1070 (17)
H4A	0.4008	0.2236	1.0625	0.128*
H4B	0.4087	0.0923	1.0625	0.128*
Cl4	0.0719 (14)	0.7626 (15)	0.7497 (13)	0.128 (4)	0.334 (17)
O10	0.040 (2)	0.7880 (19)	0.8570 (11)	0.121 (7)	0.334 (17)
O9	0.053 (3)	0.653 (2)	0.703 (3)	0.152 (7)	0.334 (17)
O8	0.2286 (19)	0.797 (2)	0.7517 (18)	0.116 (6)	0.334 (17)
O7	−0.056 (2)	0.790 (2)	0.6899 (19)	0.143 (7)	0.334 (17)
Cl4'	0.0736 (4)	0.7704 (3)	0.7438 (2)	0.0580 (11)	0.666 (17)
O10'	0.0532 (11)	0.7151 (19)	0.8447 (12)	0.190 (7)	0.666 (17)
O8'	−0.0154 (17)	0.8368 (11)	0.7385 (16)	0.194 (6)	0.666 (17)
O7'	0.0428 (16)	0.6824 (13)	0.6488 (9)	0.170 (5)	0.666 (17)
O9'	0.2038 (16)	0.8551 (14)	0.7353 (12)	0.192 (7)	0.666 (17)

	U11	U22	U33	U12	U13	U23
Cl1	0.0438 (4)	0.0646 (5)	0.0609 (5)	0.0076 (3)	0.0091 (3)	0.0018 (4)
N1	0.0388 (11)	0.0521 (13)	0.0324 (11)	0.0092 (10)	0.0006 (9)	0.0014 (9)
Cl2	0.1349 (9)	0.0625 (5)	0.0344 (4)	0.0375 (5)	0.0029 (4)	−0.0051 (3)
C18	0.0411 (14)	0.0425 (14)	0.0288 (12)	0.0160 (11)	0.0007 (10)	0.0040 (10)
Cl3	0.0662 (6)	0.0702 (6)	0.0860 (7)	0.0096 (4)	−0.0143 (5)	−0.0312 (5)
C13	0.0474 (15)	0.0392 (14)	0.0388 (14)	0.0152 (12)	0.0034 (11)	0.0084 (11)
C15	0.080 (2)	0.0444 (16)	0.0293 (13)	0.0286 (15)	−0.0014 (13)	0.0032 (11)
C16	0.0540 (17)	0.0456 (16)	0.0457 (16)	0.0170 (13)	−0.0099 (13)	−0.0055 (12)
O3	0.0480 (12)	0.0607 (13)	0.0674 (14)	0.0004 (10)	0.0010 (10)	0.0068 (11)
O1	0.0443 (12)	0.0651 (14)	0.0767 (15)	0.0104 (10)	0.0073 (11)	0.0020 (11)
C17	0.0441 (15)	0.0490 (16)	0.0422 (15)	0.0127 (12)	0.0014 (12)	−0.0010 (12)
C14	0.0670 (18)	0.0451 (16)	0.0352 (14)	0.0247 (14)	0.0150 (13)	0.0108 (12)
O2	0.0764 (15)	0.0543 (13)	0.0599 (13)	0.0113 (11)	−0.0039 (11)	0.0126 (10)
O4	0.0741 (16)	0.0865 (18)	0.0550 (14)	0.0184 (13)	−0.0222 (12)	−0.0125 (12)
O6	0.0624 (14)	0.0651 (15)	0.0746 (15)	0.0004 (11)	0.0200 (12)	0.0182 (12)
O5	0.103 (2)	0.0890 (18)	0.0466 (13)	0.0389 (15)	−0.0023 (13)	0.0064 (12)
C1	0.0423 (18)	0.092 (3)	0.079 (2)	0.0084 (18)	0.0038 (17)	−0.022 (2)
C9	0.113 (3)	0.052 (2)	0.065 (2)	−0.005 (2)	0.015 (2)	0.0152 (17)
C10	0.121 (3)	0.051 (2)	0.060 (2)	0.021 (2)	−0.015 (2)	0.0118 (16)
C6	0.088 (3)	0.106 (3)	0.056 (2)	0.042 (2)	−0.0287 (19)	−0.019 (2)
C8	0.056 (2)	0.065 (2)	0.097 (3)	−0.0067 (17)	−0.0035 (19)	−0.020 (2)
C7	0.071 (2)	0.089 (3)	0.081 (3)	0.006 (2)	−0.030 (2)	−0.033 (2)
C2	0.064 (2)	0.094 (3)	0.065 (2)	−0.024 (2)	0.0227 (18)	−0.004 (2)
C3	0.130 (4)	0.076 (3)	0.076 (3)	0.011 (3)	0.031 (3)	0.031 (2)
C11	0.088 (3)	0.081 (3)	0.086 (3)	0.018 (2)	−0.025 (2)	0.027 (2)
C12	0.058 (2)	0.076 (3)	0.139 (4)	0.023 (2)	−0.024 (2)	0.020 (3)
C5	0.111 (3)	0.103 (3)	0.067 (2)	0.054 (3)	−0.031 (2)	−0.008 (2)
C4	0.151 (5)	0.135 (4)	0.061 (3)	0.072 (4)	0.016 (3)	0.035 (3)
Cl4	0.090 (6)	0.144 (8)	0.143 (8)	0.028 (6)	−0.025 (6)	0.004 (7)
O10	0.135 (11)	0.177 (15)	0.031 (6)	0.018 (10)	0.037 (6)	−0.010 (8)
O9	0.148 (11)	0.102 (10)	0.203 (17)	0.057 (9)	−0.002 (13)	−0.030 (12)
O8	0.058 (6)	0.188 (15)	0.089 (7)	0.017 (9)	0.016 (5)	0.010 (10)
O7	0.117 (9)	0.173 (15)	0.138 (11)	0.020 (10)	−0.047 (9)	0.060 (10)
Cl4'	0.0618 (17)	0.0635 (16)	0.0419 (15)	0.0072 (12)	0.0088 (11)	0.0024 (10)
O10'	0.089 (5)	0.337 (18)	0.144 (9)	−0.002 (8)	−0.019 (5)	0.153 (11)
O8'	0.194 (12)	0.141 (8)	0.264 (15)	0.093 (8)	−0.029 (10)	−0.008 (8)
O7'	0.235 (10)	0.144 (9)	0.114 (6)	0.056 (7)	−0.074 (6)	−0.049 (6)
O9'	0.149 (10)	0.187 (11)	0.152 (9)	−0.087 (8)	0.067 (8)	−0.022 (8)

Cl1—C13	1.724 (3)	C10—H10A	0.9700
N1—C18	1.466 (3)	C10—H10B	0.9700
N1—H1C	0.8900	C6—C5	1.486 (6)
N1—H1D	0.8900	C6—H6A	0.9700
N1—H1E	0.8900	C6—H6B	0.9700
Cl2—C15	1.735 (3)	C8—C7	1.454 (6)
C18—C17	1.374 (4)	C8—H8A	0.9700
C18—C13	1.395 (4)	C8—H8B	0.9700
Cl3—C16	1.733 (3)	C7—H7A	0.9700
C13—C14	1.383 (4)	C7—H7B	0.9700
C15—C14	1.376 (4)	C2—H2A	0.9700
C15—C16	1.383 (4)	C2—H2B	0.9700
C16—C17	1.385 (4)	C3—C4	1.511 (7)
O3—C8	1.425 (4)	C3—H3A	0.9700
O3—C9	1.427 (4)	C3—H3B	0.9700
O1—C1	1.409 (4)	C11—C12	1.473 (6)
O1—C12	1.441 (4)	C11—H11A	0.9700
C17—H17A	0.9300	C11—H11B	0.9700
C14—H14A	0.9300	C12—H12A	0.9700
O2—C11	1.412 (4)	C12—H12B	0.9700
O2—C10	1.413 (4)	C5—H5A	0.9700
O4—C6	1.415 (5)	C5—H5B	0.9700
O4—C7	1.442 (5)	C4—H4A	0.9700
O6—C3	1.422 (5)	C4—H4B	0.9700
O6—C2	1.436 (4)	Cl4—O9	1.30 (2)
O5—C4	1.391 (5)	Cl4—O10	1.322 (19)
O5—C5	1.426 (5)	Cl4—O8	1.43 (2)
C1—C2	1.468 (6)	Cl4—O7	1.53 (2)
C1—H1A	0.9700	Cl4'—O8'	1.300 (13)
C1—H1B	0.9700	Cl4'—O9'	1.384 (11)
C9—C10	1.470 (6)	Cl4'—O7'	1.395 (10)
C9—H9A	0.9700	Cl4'—O10'	1.428 (12)
C9—H9B	0.9700
C18—N1—H1C	109.5	O3—C8—H8B	110.0
C18—N1—H1D	109.5	C7—C8—H8B	110.0
H1C—N1—H1D	109.5	H8A—C8—H8B	108.4
C18—N1—H1E	109.5	O4—C7—C8	110.2 (3)
H1C—N1—H1E	109.5	O4—C7—H7A	109.6
H1D—N1—H1E	109.5	C8—C7—H7A	109.6
C17—C18—C13	120.2 (2)	O4—C7—H7B	109.6
C17—C18—N1	120.1 (2)	C8—C7—H7B	109.6
C13—C18—N1	119.7 (2)	H7A—C7—H7B	108.1
C14—C13—C18	120.1 (3)	O6—C2—C1	110.1 (3)
C14—C13—Cl1	119.9 (2)	O6—C2—H2A	109.6
C18—C13—Cl1	120.1 (2)	C1—C2—H2A	109.6
C14—C15—C16	120.6 (2)	O6—C2—H2B	109.6
C14—C15—Cl2	118.0 (2)	C1—C2—H2B	109.6
C16—C15—Cl2	121.3 (2)	H2A—C2—H2B	108.2
C15—C16—C17	120.1 (3)	O6—C3—C4	109.4 (3)
C15—C16—Cl3	120.7 (2)	O6—C3—H3A	109.8
C17—C16—Cl3	119.2 (2)	C4—C3—H3A	109.8
C8—O3—C9	111.4 (3)	O6—C3—H3B	109.8
C1—O1—C12	114.0 (3)	C4—C3—H3B	109.8
C18—C17—C16	119.5 (3)	H3A—C3—H3B	108.2
C18—C17—H17A	120.2	O2—C11—C12	113.0 (3)
C16—C17—H17A	120.2	O2—C11—H11A	109.0
C15—C14—C13	119.3 (3)	C12—C11—H11A	109.0
C15—C14—H14A	120.3	O2—C11—H11B	109.0
C13—C14—H14A	120.3	C12—C11—H11B	109.0
C11—O2—C10	113.4 (3)	H11A—C11—H11B	107.8
C6—O4—C7	112.1 (3)	O1—C12—C11	109.9 (3)
C3—O6—C2	114.4 (3)	O1—C12—H12A	109.7
C4—O5—C5	113.4 (3)	C11—C12—H12A	109.7
O1—C1—C2	109.6 (3)	O1—C12—H12B	109.7
O1—C1—H1A	109.7	C11—C12—H12B	109.7
C2—C1—H1A	109.7	H12A—C12—H12B	108.2
O1—C1—H1B	109.7	O5—C5—C6	113.9 (3)
C2—C1—H1B	109.7	O5—C5—H5A	108.8
H1A—C1—H1B	108.2	C6—C5—H5A	108.8
O3—C9—C10	108.6 (3)	O5—C5—H5B	108.8
O3—C9—H9A	110.0	C6—C5—H5B	108.8
C10—C9—H9A	110.0	H5A—C5—H5B	107.7
O3—C9—H9B	110.0	O5—C4—C3	112.3 (4)
C10—C9—H9B	110.0	O5—C4—H4A	109.1
H9A—C9—H9B	108.3	C3—C4—H4A	109.1
O2—C10—C9	108.7 (3)	O5—C4—H4B	109.1
O2—C10—H10A	109.9	C3—C4—H4B	109.1
C9—C10—H10A	109.9	H4A—C4—H4B	107.9
O2—C10—H10B	109.9	O9—Cl4—O10	121.0 (19)
C9—C10—H10B	109.9	O9—Cl4—O8	97.3 (18)
H10A—C10—H10B	108.3	O10—Cl4—O8	104.3 (15)
O4—C6—C5	108.9 (3)	O9—Cl4—O7	98.8 (15)
O4—C6—H6A	109.9	O10—Cl4—O7	99.6 (15)
C5—C6—H6A	109.9	O8—Cl4—O7	138.5 (15)
O4—C6—H6B	109.9	O8'—Cl4'—O9'	98.7 (13)
C5—C6—H6B	109.9	O8'—Cl4'—O7'	108.0 (8)
H6A—C6—H6B	108.3	O9'—Cl4'—O7'	111.9 (9)
O3—C8—C7	108.5 (3)	O8'—Cl4'—O10'	110.5 (9)
O3—C8—H8A	110.0	O9'—Cl4'—O10'	118.0 (10)
C7—C8—H8A	110.0	O7'—Cl4'—O10'	109.0 (8)
C17—C18—C13—C14	−2.6 (4)	C8—O3—C9—C10	−178.9 (3)
N1—C18—C13—C14	176.2 (2)	C11—O2—C10—C9	−175.8 (3)
C17—C18—C13—Cl1	176.8 (2)	O3—C9—C10—O2	−67.2 (4)
N1—C18—C13—Cl1	−4.4 (3)	C7—O4—C6—C5	179.2 (3)
C14—C15—C16—C17	−3.1 (4)	C9—O3—C8—C7	173.2 (3)
Cl2—C15—C16—C17	178.7 (2)	C6—O4—C7—C8	179.2 (3)
C14—C15—C16—Cl3	176.1 (2)	O3—C8—C7—O4	64.0 (4)
Cl2—C15—C16—Cl3	−2.1 (3)	C3—O6—C2—C1	176.1 (3)
C13—C18—C17—C16	2.4 (4)	O1—C1—C2—O6	59.2 (4)
N1—C18—C17—C16	−176.4 (2)	C2—O6—C3—C4	−172.0 (3)
C15—C16—C17—C18	0.4 (4)	C10—O2—C11—C12	−77.7 (4)
Cl3—C16—C17—C18	−178.8 (2)	C1—O1—C12—C11	175.7 (3)
C16—C15—C14—C13	2.9 (4)	O2—C11—C12—O1	−61.4 (4)
Cl2—C15—C14—C13	−178.8 (2)	C4—O5—C5—C6	−83.1 (4)
C18—C13—C14—C15	−0.1 (4)	O4—C6—C5—O5	−59.9 (5)
Cl1—C13—C14—C15	−179.5 (2)	C5—O5—C4—C3	179.2 (3)
C12—O1—C1—C2	175.0 (3)	O6—C3—C4—O5	−65.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1i	0.89	2.13	2.916 (3)	147
N1—H1C···O6i	0.89	2.21	2.899 (3)	134
N1—H1D···O5i	0.89	2.06	2.896 (3)	156
N1—H1D···O4i	0.89	2.52	3.052 (3)	119
N1—H1E···O3i	0.89	2.19	3.046 (3)	161
N1—H1E···O2i	0.89	2.35	2.856 (3)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1i	0.89	2.13	2.916 (3)	147
N1—H1C⋯O6i	0.89	2.21	2.899 (3)	134
N1—H1D⋯O5i	0.89	2.06	2.896 (3)	156
N1—H1D⋯O4i	0.89	2.52	3.052 (3)	119
N1—H1E⋯O3i	0.89	2.19	3.046 (3)	161
N1—H1E⋯O2i	0.89	2.35	2.856 (3)	116

Symmetry code: (i) .