Bis(n-do-decyl-ammonium) bis-(chlor-anil-ato)di-ethano-lcuprate(II).

In the title compound, (C12H25NH3)2[Cu(C6Cl2O4)2(C2H5OH)2], the Cu(II) atom lies on a crystallographic inversion center and is coordinated in a distorted octa-hedral geometry by four O atoms of two chloranilate ligands and two O atoms of two ethanol mol-ecules which are trans to each other in the axial positions. In the crystal, the Cu(II) mononuclear dianions are linked by O-H⋯O hydrogen bonds into a tape along the a-axis direction. The tapes are linked through N-H⋯O hydrogen bonds between the dianion and the n-do-decyl-ammonium cation, forming a two-dimensional network parallel to the ab plane.

Related literature

For metal complexes of chloranilic acid, see: Kawata & Kitagawa (2002 ▶); Kawata et al. (2000 ▶); Luo et al. (2004 ▶); Abrahams et al. (2011 ▶); Nagayoshi et al. (2003 ▶); Nishimura et al. (2013 ▶).

Experimental

Crystal data

(C12H28N)2[Cu(C6Cl2O4)2(C2H6O)2]

M = 942.34

Triclinic,

a = 9.2192 (15) Å

b = 9.4791 (13) Å

c = 15.162 (3) Å

α = 76.894 (9)°

β = 89.133 (10)°

γ = 63.110 (6)°

V = 1145.1 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.76 mm−1

T = 100 K

0.40 × 0.30 × 0.05 mm

Data collection

Rigaku Saturn724 diffractometer

Absorption correction: multi-scan (REQAB; Rigaku, 1998 ▶) T min = 0.868, T max = 0.962

17151 measured reflections

5207 independent reflections

4796 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.079

S = 1.09

5207 reflections

275 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.92 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku, 2010 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536814001202/is5334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001202/is5334Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

(C12H28N)2[Cu(C6Cl2O4)2(C2H6O)2]	Z = 1
Mr = 942.34	F(000) = 499.00
Triclinic, P1	Dx = 1.366 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 9.2192 (15) Å	Cell parameters from 3320 reflections
b = 9.4791 (13) Å	θ = 3.1–27.5°
c = 15.162 (3) Å	µ = 0.76 mm−1
α = 76.894 (9)°	T = 100 K
β = 89.133 (10)°	Platelet, violet
γ = 63.110 (6)°	0.40 × 0.30 × 0.05 mm
V = 1145.1 (4) Å3

Rigaku Saturn724 diffractometer	4796 reflections with F2 > 2.0σ(F2)
Detector resolution: 7.111 pixels mm-1	Rint = 0.025
ω scans	θmax = 27.5°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −11→11
Tmin = 0.868, Tmax = 0.962	k = −12→12
17151 measured reflections	l = −19→19
5207 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.037P)2 + 0.6543P] where P = (Fo2 + 2Fc2)/3
5207 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.92 e Å−3
0 restraints	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	1.0000	0.01636 (8)
Cl1	0.53483 (4)	−0.04086 (4)	1.14542 (2)	0.01736 (8)
Cl2	−0.00556 (4)	0.55604 (4)	0.85100 (2)	0.01622 (8)
O1	0.52991 (12)	0.28029 (12)	1.05403 (7)	0.0178 (2)
O2	0.29500 (12)	0.53156 (12)	0.94162 (7)	0.0165 (2)
O3	−0.00228 (12)	0.23827 (12)	0.94210 (7)	0.0169 (2)
O4	0.22249 (13)	−0.00706 (13)	1.06624 (7)	0.0198 (2)
O5	0.66424 (15)	0.42290 (16)	0.87749 (8)	0.0302 (3)
N1	0.12545 (15)	−0.08274 (16)	0.90253 (9)	0.0157 (2)
C1	0.40568 (16)	0.26123 (17)	1.03371 (9)	0.0135 (3)
C2	0.27283 (16)	0.40582 (16)	0.96559 (9)	0.0135 (3)
C3	0.13943 (16)	0.39417 (17)	0.93232 (9)	0.0139 (3)
C4	0.11687 (16)	0.25682 (16)	0.96583 (9)	0.0135 (3)
C5	0.24721 (16)	0.11209 (16)	1.03867 (9)	0.0139 (3)
C6	0.38592 (17)	0.12498 (17)	1.06779 (9)	0.0141 (3)
C7	0.6455 (2)	0.3845 (2)	0.79473 (12)	0.0291 (4)
H7A	0.6655	0.2697	0.8072	0.035*
H7B	0.7267	0.3966	0.7543	0.035*
C8	0.4764 (2)	0.4956 (3)	0.74834 (13)	0.0372 (4)
H8A	0.4575	0.6090	0.7352	0.045*
H8B	0.3963	0.4826	0.7882	0.045*
H8C	0.4648	0.4678	0.6913	0.045*
C9	0.08326 (18)	−0.09264 (18)	0.80967 (10)	0.0191 (3)
H9A	−0.0364	−0.0289	0.7937	0.023*
H9B	0.1153	−0.2077	0.8105	0.023*
C10	0.16933 (18)	−0.02718 (18)	0.73788 (10)	0.0190 (3)
H10A	0.1583	−0.0583	0.6812	0.023*
H10B	0.2873	−0.0805	0.7590	0.023*
C11	0.10505 (18)	0.15795 (18)	0.71583 (10)	0.0192 (3)
H11A	−0.0115	0.2123	0.6917	0.023*
H11B	0.1121	0.1906	0.7726	0.023*
C12	0.20052 (18)	0.21605 (19)	0.64636 (10)	0.0198 (3)
H12A	0.3173	0.1602	0.6704	0.024*
H12B	0.1925	0.1840	0.5896	0.024*
C13	0.13993 (19)	0.40005 (19)	0.62405 (11)	0.0220 (3)
H13A	0.1439	0.4327	0.6812	0.026*
H13B	0.0244	0.4558	0.5979	0.026*
C14	0.23900 (19)	0.45781 (19)	0.55735 (11)	0.0212 (3)
H14A	0.3548	0.4015	0.5832	0.025*
H14B	0.2340	0.4264	0.4999	0.025*
C15	0.17839 (19)	0.64171 (19)	0.53626 (11)	0.0222 (3)
H15A	0.1724	0.6741	0.5944	0.027*
H15B	0.0662	0.6972	0.5051	0.027*
C16	0.28427 (19)	0.70182 (19)	0.47717 (11)	0.0236 (3)
H16A	0.2956	0.6647	0.4203	0.028*
H16B	0.3948	0.6522	0.5098	0.028*
C17	0.2144 (2)	0.88713 (19)	0.45306 (11)	0.0243 (3)
H17A	0.1068	0.9357	0.4173	0.029*
H17B	0.1959	0.9241	0.5102	0.029*
C18	0.3209 (2)	0.9526 (2)	0.39921 (12)	0.0273 (4)
H18A	0.3426	0.9137	0.3427	0.033*
H18B	0.4272	0.9083	0.4356	0.033*
C19	0.2427 (2)	1.1383 (2)	0.37427 (13)	0.0307 (4)
H19A	0.1422	1.1817	0.3327	0.037*
H19B	0.2100	1.1772	0.4302	0.037*
C20	0.3529 (3)	1.2073 (2)	0.32906 (15)	0.0389 (5)
H20A	0.3835	1.1722	0.2726	0.047*
H20B	0.4516	1.1675	0.3703	0.047*
H20C	0.2946	1.3268	0.3151	0.047*
H1	0.769 (3)	0.374 (3)	0.8970 (16)	0.044 (6)*
H2	0.235 (3)	−0.131 (2)	0.9169 (13)	0.021 (5)*
H3	0.088 (2)	0.020 (2)	0.9063 (12)	0.020 (4)*
H4	0.082 (2)	−0.129 (2)	0.9432 (14)	0.025 (5)*

	U11	U22	U33	U12	U13	U23
Cu1	0.01280 (12)	0.01202 (12)	0.02484 (14)	−0.00770 (10)	−0.00397 (9)	−0.00092 (10)
Cl1	0.01591 (16)	0.01415 (16)	0.01890 (16)	−0.00615 (13)	−0.00402 (12)	0.00037 (12)
Cl2	0.01428 (15)	0.01421 (16)	0.01823 (16)	−0.00668 (12)	−0.00354 (12)	0.00018 (12)
O1	0.0131 (5)	0.0140 (5)	0.0256 (6)	−0.0073 (4)	−0.0046 (4)	−0.0007 (4)
O2	0.0147 (5)	0.0131 (5)	0.0222 (5)	−0.0083 (4)	−0.0027 (4)	−0.0008 (4)
O3	0.0140 (5)	0.0160 (5)	0.0223 (5)	−0.0092 (4)	−0.0012 (4)	−0.0024 (4)
O4	0.0184 (5)	0.0163 (5)	0.0257 (6)	−0.0116 (5)	−0.0023 (4)	0.0013 (5)
O5	0.0188 (6)	0.0397 (7)	0.0288 (7)	−0.0085 (6)	−0.0005 (5)	−0.0129 (6)
N1	0.0147 (6)	0.0150 (6)	0.0187 (6)	−0.0089 (5)	0.0003 (5)	−0.0017 (5)
C1	0.0107 (6)	0.0137 (7)	0.0164 (7)	−0.0055 (5)	0.0006 (5)	−0.0045 (5)
C2	0.0121 (6)	0.0126 (7)	0.0164 (7)	−0.0059 (5)	0.0020 (5)	−0.0041 (5)
C3	0.0112 (6)	0.0131 (7)	0.0157 (7)	−0.0046 (5)	−0.0007 (5)	−0.0024 (5)
C4	0.0115 (6)	0.0136 (7)	0.0159 (7)	−0.0058 (5)	0.0019 (5)	−0.0046 (5)
C5	0.0131 (7)	0.0134 (7)	0.0153 (7)	−0.0065 (6)	0.0021 (5)	−0.0032 (5)
C6	0.0128 (6)	0.0126 (6)	0.0146 (6)	−0.0046 (5)	−0.0019 (5)	−0.0015 (5)
C7	0.0311 (9)	0.0265 (9)	0.0253 (8)	−0.0106 (8)	−0.0011 (7)	−0.0038 (7)
C8	0.0294 (10)	0.0532 (12)	0.0259 (9)	−0.0172 (9)	−0.0008 (7)	−0.0082 (9)
C9	0.0191 (7)	0.0196 (7)	0.0211 (7)	−0.0118 (6)	−0.0029 (6)	−0.0032 (6)
C10	0.0194 (7)	0.0191 (7)	0.0184 (7)	−0.0091 (6)	0.0018 (6)	−0.0040 (6)
C11	0.0185 (7)	0.0187 (7)	0.0190 (7)	−0.0090 (6)	0.0017 (6)	−0.0009 (6)
C12	0.0192 (7)	0.0216 (8)	0.0168 (7)	−0.0093 (6)	0.0010 (6)	−0.0014 (6)
C13	0.0196 (7)	0.0219 (8)	0.0231 (8)	−0.0100 (6)	0.0042 (6)	−0.0020 (6)
C14	0.0209 (8)	0.0220 (8)	0.0197 (7)	−0.0104 (6)	0.0026 (6)	−0.0022 (6)
C15	0.0180 (7)	0.0215 (8)	0.0241 (8)	−0.0084 (6)	0.0030 (6)	−0.0017 (6)
C16	0.0211 (8)	0.0207 (8)	0.0253 (8)	−0.0085 (6)	0.0053 (6)	−0.0012 (6)
C17	0.0221 (8)	0.0215 (8)	0.0249 (8)	−0.0083 (7)	0.0062 (6)	−0.0016 (6)
C18	0.0256 (8)	0.0215 (8)	0.0305 (9)	−0.0092 (7)	0.0098 (7)	−0.0027 (7)
C19	0.0348 (10)	0.0216 (9)	0.0308 (9)	−0.0105 (8)	0.0100 (8)	−0.0033 (7)
C20	0.0473 (12)	0.0270 (10)	0.0437 (11)	−0.0195 (9)	0.0166 (9)	−0.0067 (8)

Cu1—O1i	1.9489 (11)	C10—C11	1.530 (2)
Cu1—O1	1.9489 (10)	C10—H10A	0.9900
Cu1—O2i	1.9657 (10)	C10—H10B	0.9900
Cu1—O2	1.9657 (10)	C11—C12	1.528 (2)
Cu1—O5i	2.4097 (13)	C11—H11A	0.9900
Cu1—O5	2.4097 (13)	C11—H11B	0.9900
Cl1—C6	1.7317 (14)	C12—C13	1.525 (2)
Cl2—C3	1.7315 (14)	C12—H12A	0.9900
O1—C1	1.2893 (17)	C12—H12B	0.9900
O2—C2	1.2713 (17)	C13—C14	1.526 (2)
O3—C4	1.2579 (17)	C13—H13A	0.9900
O4—C5	1.2322 (17)	C13—H13B	0.9900
O5—C7	1.417 (2)	C14—C15	1.525 (2)
O5—H1	0.88 (3)	C14—H14A	0.9900
N1—C9	1.5005 (19)	C14—H14B	0.9900
N1—H2	0.90 (2)	C15—C16	1.525 (2)
N1—H3	0.89 (2)	C15—H15A	0.9900
N1—H4	0.87 (2)	C15—H15B	0.9900
C1—C6	1.370 (2)	C16—C17	1.525 (2)
C1—C2	1.5242 (19)	C16—H16A	0.9900
C2—C3	1.3950 (19)	C16—H16B	0.9900
C3—C4	1.3922 (19)	C17—C18	1.521 (2)
C4—C5	1.5517 (19)	C17—H17A	0.9900
C5—C6	1.4241 (19)	C17—H17B	0.9900
C7—C8	1.499 (2)	C18—C19	1.524 (2)
C7—H7A	0.9900	C18—H18A	0.9900
C7—H7B	0.9900	C18—H18B	0.9900
C8—H8A	0.9800	C19—C20	1.518 (3)
C8—H8B	0.9800	C19—H19A	0.9900
C8—H8C	0.9800	C19—H19B	0.9900
C9—C10	1.521 (2)	C20—H20A	0.9800
C9—H9A	0.9900	C20—H20B	0.9800
C9—H9B	0.9900	C20—H20C	0.9800
O1i—Cu1—O1	180.00 (6)	C11—C10—H10A	108.6
O1i—Cu1—O2i	84.09 (4)	C9—C10—H10B	108.6
O1—Cu1—O2i	95.91 (4)	C11—C10—H10B	108.6
O1i—Cu1—O2	95.91 (4)	H10A—C10—H10B	107.6
O1—Cu1—O2	84.09 (4)	C12—C11—C10	112.43 (12)
O2i—Cu1—O2	179.999 (1)	C12—C11—H11A	109.1
O1i—Cu1—O5i	94.24 (5)	C10—C11—H11A	109.1
O1—Cu1—O5i	85.76 (5)	C12—C11—H11B	109.1
O2i—Cu1—O5i	96.70 (4)	C10—C11—H11B	109.1
O2—Cu1—O5i	83.30 (4)	H11A—C11—H11B	107.9
O1i—Cu1—O5	85.76 (5)	C13—C12—C11	113.42 (12)
O1—Cu1—O5	94.24 (5)	C13—C12—H12A	108.9
O2i—Cu1—O5	83.30 (4)	C11—C12—H12A	108.9
O2—Cu1—O5	96.70 (4)	C13—C12—H12B	108.9
O5i—Cu1—O5	179.999 (1)	C11—C12—H12B	108.9
C1—O1—Cu1	112.48 (9)	H12A—C12—H12B	107.7
C2—O2—Cu1	112.47 (9)	C12—C13—C14	113.58 (13)
C7—O5—Cu1	136.61 (11)	C12—C13—H13A	108.9
C7—O5—H1	108.8 (16)	C14—C13—H13A	108.9
Cu1—O5—H1	110.5 (15)	C12—C13—H13B	108.9
C9—N1—H2	111.6 (12)	C14—C13—H13B	108.9
C9—N1—H3	111.9 (12)	H13A—C13—H13B	107.7
H2—N1—H3	106.3 (17)	C15—C14—C13	113.12 (13)
C9—N1—H4	110.2 (13)	C15—C14—H14A	109.0
H2—N1—H4	109.3 (17)	C13—C14—H14A	109.0
H3—N1—H4	107.4 (17)	C15—C14—H14B	109.0
O1—C1—C6	125.59 (13)	C13—C14—H14B	109.0
O1—C1—C2	115.10 (12)	H14A—C14—H14B	107.8
C6—C1—C2	119.31 (12)	C14—C15—C16	114.58 (13)
O2—C2—C3	124.12 (13)	C14—C15—H15A	108.6
O2—C2—C1	115.58 (12)	C16—C15—H15A	108.6
C3—C2—C1	120.29 (12)	C14—C15—H15B	108.6
C4—C3—C2	121.21 (13)	C16—C15—H15B	108.6
C4—C3—Cl2	119.01 (10)	H15A—C15—H15B	107.6
C2—C3—Cl2	119.74 (11)	C15—C16—C17	113.00 (13)
O3—C4—C3	125.49 (13)	C15—C16—H16A	109.0
O3—C4—C5	115.72 (12)	C17—C16—H16A	109.0
C3—C4—C5	118.79 (12)	C15—C16—H16B	109.0
O4—C5—C6	124.97 (13)	C17—C16—H16B	109.0
O4—C5—C4	116.59 (12)	H16A—C16—H16B	107.8
C6—C5—C4	118.43 (12)	C18—C17—C16	115.02 (13)
C1—C6—C5	121.74 (12)	C18—C17—H17A	108.5
C1—C6—Cl1	120.25 (11)	C16—C17—H17A	108.5
C5—C6—Cl1	117.98 (10)	C18—C17—H17B	108.5
O5—C7—C8	110.19 (15)	C16—C17—H17B	108.5
O5—C7—H7A	109.6	H17A—C17—H17B	107.5
C8—C7—H7A	109.6	C17—C18—C19	112.76 (14)
O5—C7—H7B	109.6	C17—C18—H18A	109.0
C8—C7—H7B	109.6	C19—C18—H18A	109.0
H7A—C7—H7B	108.1	C17—C18—H18B	109.0
C7—C8—H8A	109.5	C19—C18—H18B	109.0
C7—C8—H8B	109.5	H18A—C18—H18B	107.8
H8A—C8—H8B	109.5	C20—C19—C18	114.12 (15)
C7—C8—H8C	109.5	C20—C19—H19A	108.7
H8A—C8—H8C	109.5	C18—C19—H19A	108.7
H8B—C8—H8C	109.5	C20—C19—H19B	108.7
N1—C9—C10	111.53 (12)	C18—C19—H19B	108.7
N1—C9—H9A	109.3	H19A—C19—H19B	107.6
C10—C9—H9A	109.3	C19—C20—H20A	109.5
N1—C9—H9B	109.3	C19—C20—H20B	109.5
C10—C9—H9B	109.3	H20A—C20—H20B	109.5
H9A—C9—H9B	108.0	C19—C20—H20C	109.5
C9—C10—C11	114.68 (12)	H20A—C20—H20C	109.5
C9—C10—H10A	108.6	H20B—C20—H20C	109.5
O2i—Cu1—O1—C1	175.55 (10)	C2—C3—C4—C5	−2.5 (2)
O2—Cu1—O1—C1	−4.45 (10)	Cl2—C3—C4—C5	179.98 (9)
O5i—Cu1—O1—C1	79.23 (10)	O3—C4—C5—O4	0.18 (18)
O5—Cu1—O1—C1	−100.77 (10)	C3—C4—C5—O4	−179.84 (13)
O1i—Cu1—O2—C2	−178.08 (10)	O3—C4—C5—C6	179.43 (12)
O1—Cu1—O2—C2	1.92 (10)	C3—C4—C5—C6	−0.59 (19)
O5i—Cu1—O2—C2	−84.49 (10)	O1—C1—C6—C5	−177.45 (13)
O5—Cu1—O2—C2	95.51 (10)	C2—C1—C6—C5	2.4 (2)
O1i—Cu1—O5—C7	−104.22 (16)	O1—C1—C6—Cl1	0.2 (2)
O1—Cu1—O5—C7	75.77 (16)	C2—C1—C6—Cl1	−179.89 (10)
O2i—Cu1—O5—C7	171.24 (16)	O4—C5—C6—C1	179.66 (14)
O2—Cu1—O5—C7	−8.76 (16)	C4—C5—C6—C1	0.5 (2)
Cu1—O1—C1—C6	−174.25 (12)	O4—C5—C6—Cl1	1.9 (2)
Cu1—O1—C1—C2	5.85 (15)	C4—C5—C6—Cl1	−177.24 (9)
Cu1—O2—C2—C3	−178.16 (11)	Cu1—O5—C7—C8	39.7 (2)
Cu1—O2—C2—C1	0.64 (15)	N1—C9—C10—C11	−70.83 (16)
O1—C1—C2—O2	−4.48 (18)	C9—C10—C11—C12	177.58 (12)
C6—C1—C2—O2	175.61 (13)	C10—C11—C12—C13	−179.36 (12)
O1—C1—C2—C3	174.36 (13)	C11—C12—C13—C14	177.86 (13)
C6—C1—C2—C3	−5.5 (2)	C12—C13—C14—C15	−179.44 (13)
O2—C2—C3—C4	−175.74 (13)	C13—C14—C15—C16	174.36 (14)
C1—C2—C3—C4	5.5 (2)	C14—C15—C16—C17	176.68 (14)
O2—C2—C3—Cl2	1.7 (2)	C15—C16—C17—C18	176.30 (14)
C1—C2—C3—Cl2	−176.99 (10)	C16—C17—C18—C19	178.04 (15)
C2—C3—C4—O3	177.46 (13)	C17—C18—C19—C20	174.00 (16)
Cl2—C3—C4—O3	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O3ii	0.88 (3)	1.94 (3)	2.8145 (16)	172 (3)
N1—H2···O1iii	0.91 (3)	1.97 (2)	2.8562 (16)	167 (3)
N1—H3···O3	0.89 (3)	2.05 (3)	2.928 (2)	168.3 (17)
N1—H4···O3iv	0.87 (3)	2.12 (3)	2.9784 (19)	171 (3)
N1—H4···O4iv	0.87 (3)	2.50 (3)	2.9842 (19)	116.2 (13)

Table 1

Selected bond lengths (Å)

Cu1—O1	1.9489 (10)
Cu1—O2	1.9657 (10)
Cu1—O5	2.4097 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯O3i	0.88 (3)	1.94 (3)	2.8145 (16)	172 (3)
N1—H2⋯O1ii	0.91 (3)	1.97 (2)	2.8562 (16)	167 (3)
N1—H3⋯O3	0.89 (3)	2.05 (3)	2.928 (2)	168.3 (17)
N1—H4⋯O3iii	0.87 (3)	2.12 (3)	2.9784 (19)	171 (3)
N1—H4⋯O4iii	0.87 (3)	2.50 (3)	2.9842 (19)	116.2 (13)

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