2,2'-(Piperazine-1,4-di-yl)diethanaminium dibenzoate.

The asymmetric unit of the title salt C(8)H(22)N(4) (2+)·2C(7)H(5)O(2) (-), comprises two independent pairs of half a 2,2'-(piperazine-1,4-di-yl)diethanaminium dication plus a benzoate anion. The dications are symmetrical and lie across crystallographic centres of inversion. The crystal structure was refined as a two-component pseudo-merohedral twin using the twin law 001 0-10 100 [he domain fractions are 0.8645 (8) and 0.1355 (8)]. The anions and cations are linked by N-H⋯O hydrogen bonds and weak N-H⋯O inter-molecular inter-actions to form infinite two-dimensional networks parallel to [101]. The conformation adopted by the cation in the crystal structure is very similar to that adopted by the same cation in the structures of the 2-hy-droxy-benzoate [Cukrowski et al. (2012 ▶). Acta Cryst, E68, o2387], the nitrate and the tetra-hydrogen penta-borate salts.

Related literature

For the structures of the 2-hy­droxy­benzoate, the nitrate and the tetra­hydrogen penta­borate salts of the 1,4-di(2-ammonio­eth­yl)piperazine cation, see: Cukrowski et al. (2012 ▶); Junk & Smith (2005 ▶); Jiang et al. (2009 ▶), respectively.

Experimental

Crystal data

C8H22N4 2+·2C7H5O2 −

M = 416.52

Monoclinic,

a = 19.5300 (4) Å

b = 6.6694 (2) Å

c = 19.6178 (4) Å

β = 115.989 (1)°

V = 2296.89 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 180 K

0.28 × 0.23 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.910, T max = 0.991

20137 measured reflections

5194 independent reflections

3970 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.02

5194 reflections

290 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶), SCALEPACK and SORTAV (Blessing, 1995 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶), POV-RAY (Cason, 2004 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030115/jj2134sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030115/jj2134Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030115/jj2134Isup3.cml

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

C8H22N42+·2C7H5O2−	F(000) = 896
Mr = 416.52	Dx = 1.204 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 12295 reflections
a = 19.5300 (4) Å	θ = 1.0–27.5°
b = 6.6694 (2) Å	µ = 0.08 mm−1
c = 19.6178 (4) Å	T = 180 K
β = 115.989 (1)°	Block, yellow
V = 2296.89 (10) Å3	0.28 × 0.23 × 0.12 mm
Z = 4

Nonius KappaCCD diffractometer	5194 independent reflections
Radiation source: fine-focus sealed tube	3970 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Thin slice ω and φ scans	θmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −25→22
Tmin = 0.910, Tmax = 0.991	k = −7→8
20137 measured reflections	l = −25→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0702P)2] where P = (Fo2 + 2Fc2)/3
5194 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
N1	0.19472 (7)	0.2447 (2)	0.19552 (7)	0.0375 (3)
H1A	0.1776 (9)	0.374 (3)	0.2008 (8)	0.045*
H1B	0.2431 (9)	0.223 (2)	0.2302 (9)	0.045*
H1C	0.1652 (9)	0.142 (3)	0.2002 (8)	0.045*
C2	0.19529 (8)	0.2437 (3)	0.12037 (8)	0.0491 (4)
H2A	0.2127	0.1110	0.1116	0.059*
H2B	0.2319	0.3457	0.1198	0.059*
C3	0.11811 (9)	0.2872 (3)	0.05773 (8)	0.0512 (4)
H3A	0.0994	0.4156	0.0686	0.061*
H3B	0.1226	0.3034	0.0097	0.061*
N4	0.06208 (7)	0.12951 (18)	0.04783 (6)	0.0418 (3)
C5	−0.01461 (8)	0.2057 (2)	0.00103 (8)	0.0458 (4)
H5A	−0.0182	0.2489	−0.0487	0.055*
H5B	−0.0242	0.3241	0.0260	0.055*
C6	0.07429 (8)	−0.0487 (2)	0.01107 (8)	0.0483 (4)
H6A	0.1254	−0.1048	0.0430	0.058*
H6B	0.0726	−0.0106	−0.0384	0.058*
C7	0.46941 (7)	0.2132 (2)	0.30262 (7)	0.0347 (3)
C8	0.51949 (8)	0.3595 (3)	0.30237 (8)	0.0470 (4)
H8	0.5013	0.4909	0.2852	0.056*
C9	0.59622 (9)	0.3155 (3)	0.32714 (9)	0.0583 (5)
H9	0.6304	0.4175	0.3276	0.070*
C10	0.62302 (9)	0.1248 (3)	0.35110 (9)	0.0566 (5)
H10	0.6755	0.0952	0.3680	0.068*
C11	0.57335 (9)	−0.0231 (3)	0.35052 (8)	0.0512 (4)
H11	0.5915	−0.1552	0.3664	0.061*
C12	0.49691 (8)	0.0210 (2)	0.32676 (8)	0.0415 (3)
H12	0.4631	−0.0809	0.3270	0.050*
C13	0.38687 (7)	0.2669 (2)	0.27915 (7)	0.0340 (3)
O14	0.36433 (5)	0.43634 (15)	0.25215 (5)	0.0429 (2)
O15	0.34467 (5)	0.13526 (15)	0.28820 (6)	0.0435 (3)
N1'	0.18677 (7)	0.8130 (2)	0.69616 (7)	0.0387 (3)
H1'A	0.2019 (9)	0.704 (3)	0.6812 (9)	0.046*
H1'B	0.2193 (9)	0.845 (2)	0.7439 (10)	0.046*
H1'C	0.1828 (9)	0.917 (3)	0.6640 (9)	0.046*
C2'	0.11280 (9)	0.7645 (3)	0.69548 (8)	0.0490 (4)
H2'A	0.0946	0.8814	0.7141	0.059*
H2'B	0.1193	0.6506	0.7301	0.059*
C3'	0.05450 (8)	0.7108 (3)	0.61682 (8)	0.0484 (4)
H3'A	0.0703	0.5854	0.6006	0.058*
H3'B	0.0049	0.6857	0.6177	0.058*
N4'	0.04519 (6)	0.86872 (18)	0.56193 (6)	0.0409 (3)
C5'	0.00761 (8)	1.0480 (2)	0.57298 (8)	0.0458 (4)
H5'A	0.0379	1.1020	0.6246	0.055*
H5'B	−0.0434	1.0114	0.5683	0.055*
C6'	0.00043 (8)	0.7944 (2)	0.48472 (8)	0.0441 (4)
H6'A	−0.0507	0.7539	0.4785	0.053*
H6'B	0.0256	0.6747	0.4762	0.053*
C7'	0.19900 (7)	0.3513 (2)	0.53125 (7)	0.0351 (3)
C8'	0.17823 (8)	0.5420 (2)	0.50088 (8)	0.0425 (3)
H8'	0.1815	0.6515	0.5332	0.051*
C9'	0.15272 (9)	0.5741 (3)	0.42383 (9)	0.0515 (4)
H9'	0.1377	0.7044	0.4032	0.062*
C10'	0.14927 (9)	0.4151 (3)	0.37717 (9)	0.0533 (4)
H10'	0.1315	0.4365	0.3243	0.064*
C11'	0.17134 (9)	0.2262 (3)	0.40677 (8)	0.0518 (4)
H11'	0.1699	0.1181	0.3746	0.062*
C12'	0.19571 (8)	0.1943 (2)	0.48389 (8)	0.0440 (3)
H12'	0.2102	0.0634	0.5043	0.053*
C13'	0.22236 (7)	0.3122 (2)	0.61444 (7)	0.0355 (3)
O14'	0.23245 (6)	0.46100 (17)	0.65735 (5)	0.0521 (3)
O15'	0.23097 (6)	0.13489 (16)	0.63648 (6)	0.0478 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0311 (6)	0.0325 (7)	0.0436 (6)	−0.0018 (5)	0.0115 (5)	−0.0006 (5)
C2	0.0417 (8)	0.0570 (10)	0.0495 (8)	−0.0097 (7)	0.0207 (6)	−0.0086 (7)
C3	0.0576 (9)	0.0497 (10)	0.0432 (8)	−0.0072 (8)	0.0193 (7)	0.0004 (7)
N4	0.0427 (7)	0.0410 (7)	0.0360 (6)	−0.0020 (5)	0.0119 (5)	−0.0013 (5)
C5	0.0519 (9)	0.0402 (8)	0.0360 (7)	0.0059 (7)	0.0107 (6)	−0.0001 (6)
C6	0.0448 (8)	0.0519 (10)	0.0428 (7)	0.0073 (7)	0.0144 (6)	−0.0012 (7)
C7	0.0362 (7)	0.0386 (8)	0.0291 (6)	0.0007 (6)	0.0141 (5)	−0.0019 (5)
C8	0.0428 (8)	0.0523 (10)	0.0458 (8)	−0.0024 (7)	0.0195 (6)	0.0051 (7)
C9	0.0424 (9)	0.0790 (14)	0.0564 (9)	−0.0083 (9)	0.0242 (7)	0.0073 (8)
C10	0.0378 (8)	0.0872 (14)	0.0471 (8)	0.0120 (9)	0.0209 (6)	0.0019 (8)
C11	0.0468 (8)	0.0586 (11)	0.0473 (8)	0.0164 (8)	0.0198 (6)	0.0009 (7)
C12	0.0405 (8)	0.0430 (9)	0.0401 (7)	0.0045 (6)	0.0169 (6)	−0.0012 (6)
C13	0.0375 (7)	0.0331 (8)	0.0299 (6)	0.0004 (6)	0.0133 (5)	−0.0028 (5)
O14	0.0447 (5)	0.0350 (6)	0.0472 (5)	0.0067 (4)	0.0184 (4)	0.0049 (4)
O15	0.0346 (5)	0.0389 (6)	0.0540 (6)	−0.0003 (4)	0.0167 (4)	0.0055 (4)
N1'	0.0444 (7)	0.0342 (7)	0.0334 (6)	−0.0010 (5)	0.0132 (5)	0.0019 (5)
C2'	0.0499 (9)	0.0546 (10)	0.0447 (8)	−0.0003 (7)	0.0227 (7)	0.0058 (7)
C3'	0.0402 (8)	0.0472 (10)	0.0529 (9)	−0.0060 (7)	0.0159 (6)	0.0023 (7)
N4'	0.0353 (6)	0.0389 (7)	0.0423 (6)	−0.0011 (5)	0.0113 (5)	−0.0021 (5)
C5'	0.0419 (8)	0.0485 (9)	0.0432 (8)	−0.0010 (7)	0.0152 (6)	−0.0082 (7)
C6'	0.0376 (7)	0.0406 (9)	0.0476 (8)	−0.0017 (6)	0.0127 (6)	−0.0088 (6)
C7'	0.0308 (6)	0.0379 (8)	0.0375 (7)	−0.0013 (6)	0.0159 (5)	0.0026 (6)
C8'	0.0444 (8)	0.0390 (9)	0.0466 (8)	0.0006 (6)	0.0223 (6)	0.0053 (6)
C9'	0.0560 (9)	0.0530 (10)	0.0492 (8)	0.0069 (8)	0.0265 (7)	0.0185 (8)
C10'	0.0478 (8)	0.0758 (13)	0.0375 (7)	0.0002 (8)	0.0198 (6)	0.0123 (8)
C11'	0.0554 (9)	0.0616 (11)	0.0402 (8)	−0.0002 (8)	0.0226 (7)	−0.0054 (7)
C12'	0.0472 (8)	0.0404 (8)	0.0425 (8)	0.0024 (7)	0.0179 (6)	0.0008 (6)
C13'	0.0312 (7)	0.0365 (8)	0.0388 (7)	0.0026 (6)	0.0154 (5)	0.0036 (6)
O14'	0.0690 (7)	0.0428 (7)	0.0385 (5)	0.0114 (5)	0.0181 (5)	−0.0018 (5)
O15'	0.0582 (7)	0.0390 (6)	0.0432 (5)	−0.0003 (5)	0.0195 (5)	0.0086 (4)

N1—C2	1.4792 (19)	N1'—C2'	1.475 (2)
N1—H1A	0.945 (18)	N1'—H1'A	0.882 (19)
N1—H1B	0.902 (16)	N1'—H1'B	0.897 (17)
N1—H1C	0.925 (18)	N1'—H1'C	0.916 (18)
C2—C3	1.498 (2)	C2'—C3'	1.505 (2)
C2—H2A	0.9900	C2'—H2'A	0.9900
C2—H2B	0.9900	C2'—H2'B	0.9900
C3—N4	1.468 (2)	C3'—N4'	1.460 (2)
C3—H3A	0.9900	C3'—H3'A	0.9900
C3—H3B	0.9900	C3'—H3'B	0.9900
N4—C5	1.4625 (19)	N4'—C6'	1.4640 (18)
N4—C6	1.463 (2)	N4'—C5'	1.468 (2)
C5—C6i	1.506 (2)	C5'—C6'ii	1.502 (2)
C5—H5A	0.9900	C5'—H5'A	0.9900
C5—H5B	0.9900	C5'—H5'B	0.9900
C6—C5i	1.506 (2)	C6'—C5'ii	1.502 (2)
C6—H6A	0.9900	C6'—H6'A	0.9900
C6—H6B	0.9900	C6'—H6'B	0.9900
C7—C8	1.383 (2)	C7'—C12'	1.383 (2)
C7—C12	1.390 (2)	C7'—C8'	1.388 (2)
C7—C13	1.5127 (18)	C7'—C13'	1.5125 (18)
C8—C9	1.389 (2)	C8'—C9'	1.385 (2)
C8—H8	0.9500	C8'—H8'	0.9500
C9—C10	1.378 (3)	C9'—C10'	1.383 (3)
C9—H9	0.9500	C9'—H9'	0.9500
C10—C11	1.380 (3)	C10'—C11'	1.375 (3)
C10—H10	0.9500	C10'—H10'	0.9500
C11—C12	1.387 (2)	C11'—C12'	1.389 (2)
C11—H11	0.9500	C11'—H11'	0.9500
C12—H12	0.9500	C12'—H12'	0.9500
C13—O14	1.2436 (17)	C13'—O15'	1.2447 (17)
C13—O15	1.2690 (17)	C13'—O14'	1.2599 (17)
C2—N1—H1A	105.8 (9)	C2'—N1'—H1'A	106.7 (11)
C2—N1—H1B	106.8 (9)	C2'—N1'—H1'B	107.8 (10)
H1A—N1—H1B	111.6 (14)	H1'A—N1'—H1'B	110.8 (14)
C2—N1—H1C	111.9 (10)	C2'—N1'—H1'C	111.8 (10)
H1A—N1—H1C	113.4 (14)	H1'A—N1'—H1'C	109.5 (14)
H1B—N1—H1C	107.2 (14)	H1'B—N1'—H1'C	110.2 (15)
N1—C2—C3	111.87 (13)	N1'—C2'—C3'	111.07 (12)
N1—C2—H2A	109.2	N1'—C2'—H2'A	109.4
C3—C2—H2A	109.2	C3'—C2'—H2'A	109.4
N1—C2—H2B	109.2	N1'—C2'—H2'B	109.4
C3—C2—H2B	109.2	C3'—C2'—H2'B	109.4
H2A—C2—H2B	107.9	H2'A—C2'—H2'B	108.0
N4—C3—C2	113.21 (13)	N4'—C3'—C2'	112.22 (13)
N4—C3—H3A	108.9	N4'—C3'—H3'A	109.2
C2—C3—H3A	108.9	C2'—C3'—H3'A	109.2
N4—C3—H3B	108.9	N4'—C3'—H3'B	109.2
C2—C3—H3B	108.9	C2'—C3'—H3'B	109.2
H3A—C3—H3B	107.8	H3'A—C3'—H3'B	107.9
C5—N4—C6	108.42 (11)	C3'—N4'—C6'	110.11 (12)
C5—N4—C3	109.47 (12)	C3'—N4'—C5'	112.79 (12)
C6—N4—C3	111.96 (12)	C6'—N4'—C5'	108.54 (11)
N4—C5—C6i	111.48 (13)	N4'—C5'—C6'ii	110.65 (12)
N4—C5—H5A	109.3	N4'—C5'—H5'A	109.5
C6i—C5—H5A	109.3	C6'ii—C5'—H5'A	109.5
N4—C5—H5B	109.3	N4'—C5'—H5'B	109.5
C6i—C5—H5B	109.3	C6'ii—C5'—H5'B	109.5
H5A—C5—H5B	108.0	H5'A—C5'—H5'B	108.1
N4—C6—C5i	111.13 (12)	N4'—C6'—C5'ii	111.14 (12)
N4—C6—H6A	109.4	N4'—C6'—H6'A	109.4
C5i—C6—H6A	109.4	C5'ii—C6'—H6'A	109.4
N4—C6—H6B	109.4	N4'—C6'—H6'B	109.4
C5i—C6—H6B	109.4	C5'ii—C6'—H6'B	109.4
H6A—C6—H6B	108.0	H6'A—C6'—H6'B	108.0
C8—C7—C12	118.90 (13)	C12'—C7'—C8'	119.15 (12)
C8—C7—C13	119.50 (13)	C12'—C7'—C13'	119.82 (13)
C12—C7—C13	121.57 (12)	C8'—C7'—C13'	120.99 (13)
C7—C8—C9	120.39 (16)	C9'—C8'—C7'	120.50 (14)
C7—C8—H8	119.8	C9'—C8'—H8'	119.7
C9—C8—H8	119.8	C7'—C8'—H8'	119.7
C10—C9—C8	120.31 (16)	C10'—C9'—C8'	119.60 (15)
C10—C9—H9	119.8	C10'—C9'—H9'	120.2
C8—C9—H9	119.8	C8'—C9'—H9'	120.2
C9—C10—C11	119.78 (15)	C11'—C10'—C9'	120.50 (14)
C9—C10—H10	120.1	C11'—C10'—H10'	119.7
C11—C10—H10	120.1	C9'—C10'—H10'	119.7
C10—C11—C12	120.04 (16)	C10'—C11'—C12'	119.65 (16)
C10—C11—H11	120.0	C10'—C11'—H11'	120.2
C12—C11—H11	120.0	C12'—C11'—H11'	120.2
C11—C12—C7	120.57 (14)	C7'—C12'—C11'	120.56 (15)
C11—C12—H12	119.7	C7'—C12'—H12'	119.7
C7—C12—H12	119.7	C11'—C12'—H12'	119.7
O14—C13—O15	123.91 (12)	O15'—C13'—O14'	123.96 (12)
O14—C13—C7	118.44 (12)	O15'—C13'—C7'	118.02 (12)
O15—C13—C7	117.65 (12)	O14'—C13'—C7'	118.01 (12)
N1—C2—C3—N4	−66.32 (18)	N1'—C2'—C3'—N4'	−56.03 (18)
C2—C3—N4—C5	164.89 (13)	C2'—C3'—N4'—C6'	168.40 (13)
C2—C3—N4—C6	−74.84 (16)	C2'—C3'—N4'—C5'	−70.19 (16)
C6—N4—C5—C6i	57.36 (17)	C3'—N4'—C5'—C6'ii	179.90 (11)
C3—N4—C5—C6i	179.76 (12)	C6'—N4'—C5'—C6'ii	−57.80 (16)
C5—N4—C6—C5i	−57.14 (17)	C3'—N4'—C6'—C5'ii	−177.99 (12)
C3—N4—C6—C5i	−178.01 (11)	C5'—N4'—C6'—C5'ii	58.10 (16)
C12—C7—C8—C9	−1.1 (2)	C12'—C7'—C8'—C9'	1.6 (2)
C13—C7—C8—C9	176.94 (13)	C13'—C7'—C8'—C9'	−176.24 (13)
C7—C8—C9—C10	1.0 (2)	C7'—C8'—C9'—C10'	−1.2 (2)
C8—C9—C10—C11	−0.1 (2)	C8'—C9'—C10'—C11'	−0.3 (2)
C9—C10—C11—C12	−0.8 (2)	C9'—C10'—C11'—C12'	1.4 (2)
C10—C11—C12—C7	0.7 (2)	C8'—C7'—C12'—C11'	−0.5 (2)
C8—C7—C12—C11	0.28 (19)	C13'—C7'—C12'—C11'	177.32 (13)
C13—C7—C12—C11	−177.74 (12)	C10'—C11'—C12'—C7'	−0.9 (2)
C8—C7—C13—O14	7.89 (17)	C12'—C7'—C13'—O15'	−6.79 (19)
C12—C7—C13—O14	−174.10 (12)	C8'—C7'—C13'—O15'	171.02 (13)
C8—C7—C13—O15	−172.22 (12)	C12'—C7'—C13'—O14'	172.71 (13)
C12—C7—C13—O15	5.79 (17)	C8'—C7'—C13'—O14'	−9.48 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O15iii	0.945 (18)	1.833 (19)	2.7739 (17)	173.0 (15)
N1—H1B···O15	0.902 (16)	1.895 (17)	2.7836 (15)	167.8 (14)
N1—H1B···O14	0.902 (16)	2.632 (16)	3.2580 (16)	127.2 (13)
N1—H1C···O14iv	0.925 (18)	1.887 (18)	2.7660 (16)	157.9 (14)
N1′—H1′A···O14′	0.882 (19)	1.857 (19)	2.7355 (17)	174.2 (15)
N1′—H1′B···O14′v	0.897 (17)	1.908 (17)	2.7836 (16)	164.8 (15)
N1′—H1′B···O15′v	0.897 (17)	2.533 (16)	3.1858 (16)	130.1 (13)
N1′—H1′C···O15′vi	0.916 (18)	1.934 (18)	2.7585 (16)	148.8 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O15i	0.945 (18)	1.833 (19)	2.7739 (17)	173.0 (15)
N1—H1B⋯O15	0.902 (16)	1.895 (17)	2.7836 (15)	167.8 (14)
N1—H1B⋯O14	0.902 (16)	2.632 (16)	3.2580 (16)	127.2 (13)
N1—H1C⋯O14ii	0.925 (18)	1.887 (18)	2.7660 (16)	157.9 (14)
N1′—H1′A⋯O14′	0.882 (19)	1.857 (19)	2.7355 (17)	174.2 (15)
N1′—H1′B⋯O14′iii	0.897 (17)	1.908 (17)	2.7836 (16)	164.8 (15)
N1′—H1′B⋯O15′iii	0.897 (17)	2.533 (16)	3.1858 (16)	130.1 (13)
N1′—H1′C⋯O15′iv	0.916 (18)	1.934 (18)	2.7585 (16)	148.8 (14)

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