Bis(piperazinediium) benzene-1,2,4,5-tetra-carboxyl-ate hexa-hydrate.

The title compound, 2C(4)H(12)N(2) (2+)·C(10)H(2)O(8) (4-)·6H(2)O or (pipzH(2))(2)(btc)·6H(2)O, was formed from the reaction between benzene-1,2,4,5-tetra-carboxylic acid (btcH(4)) as a proton donor and piperazine (pipz) as a proton acceptor. A variety of O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, as well as C-H⋯π inter-actions, are present in the crystal structure. Two water O atoms are each disordered over two positions; for both the site occupany factors are ca 0.66 and 0.34.

Related literature

For related literature, see: Aghabozorg et al. (2006 ▶, 2007 ▶); Arora & Pedireddi (2003 ▶); Biradha & Zaworotko (1998 ▶).

Experimental

Crystal data

2C4H12N2 2+·C10H2O8 4−·6H2O

M = 534.52

Triclinic,

a = 6.7420 (4) Å

b = 12.4636 (7) Å

c = 16.0100 (9) Å

α = 99.0920 (10)°

β = 90.3470 (10)°

γ = 105.5280 (10)°

V = 1278.27 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 100 (2) K

0.23 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.982

13995 measured reflections

5839 independent reflections

4805 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.159

S = 1.02

5839 reflections

323 parameters

H-atom parameters constrained

Δρmax = 2.20 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007332/bt2674sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007332/bt2674Isup2.hkl

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

2C4H12N22+·C10H2O84–·6H2O	Z = 2
Mr = 534.52	F000 = 572
Triclinic, P1	Dx = 1.389 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.7420 (4) Å	Cell parameters from 614 reflections
b = 12.4636 (7) Å	θ = 3–29º
c = 16.0100 (9) Å	µ = 0.12 mm−1
α = 99.0920 (10)º	T = 100 (2) K
β = 90.3470 (10)º	Prism, colorless
γ = 105.5280 (10)º	0.23 × 0.21 × 0.17 mm
V = 1278.27 (13) Å3

Bruker APEXII CCD area-detector diffractometer	5839 independent reflections
Radiation source: fine-focus sealed tube	4805 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 3.1º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.970, Tmax = 0.982	k = −16→16
13995 measured reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.07P)2 + 2P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5839 reflections	Δρmax = 2.20 e Å−3
323 parameters	Δρmin = −0.59 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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)
N1	−0.1642 (3)	0.13752 (14)	0.70314 (11)	0.0148 (4)
H1C	−0.2812	0.1173	0.6680	0.018*
H1D	−0.1227	0.0735	0.7058	0.018*
N2	0.1462 (3)	0.30353 (14)	0.81088 (11)	0.0141 (3)
H2C	0.1056	0.3677	0.8077	0.017*
H2D	0.2632	0.3239	0.8460	0.017*
C1	−0.2126 (3)	0.18509 (18)	0.78933 (14)	0.0179 (4)
H1A	−0.3195	0.1274	0.8122	0.022*
H1B	−0.2674	0.2506	0.7862	0.022*
C2	−0.0202 (3)	0.22196 (18)	0.84771 (13)	0.0163 (4)
H2A	−0.0515	0.2580	0.9039	0.020*
H2B	0.0267	0.1552	0.8555	0.020*
C3	0.1944 (3)	0.25478 (18)	0.72488 (13)	0.0158 (4)
H3A	0.2459	0.1882	0.7282	0.019*
H3B	0.3032	0.3114	0.7018	0.019*
C4	0.0012 (3)	0.22030 (17)	0.66729 (13)	0.0150 (4)
H4A	−0.0454	0.2877	0.6615	0.018*
H4B	0.0312	0.1860	0.6103	0.018*
N3	0.3335 (3)	0.76396 (16)	0.71554 (12)	0.0178 (4)
H3C	0.2266	0.7216	0.7419	0.021*
H3D	0.2885	0.8194	0.6960	0.021*
N4	0.6573 (3)	0.65653 (16)	0.73462 (11)	0.0171 (4)
H4C	0.7631	0.6995	0.7082	0.021*
H4D	0.7039	0.6016	0.7541	0.021*
C5	0.5109 (3)	0.81764 (19)	0.77813 (14)	0.0194 (4)
H5A	0.4648	0.8619	0.8274	0.023*
H5B	0.6199	0.8701	0.7517	0.023*
C6	0.5976 (3)	0.7297 (2)	0.80781 (14)	0.0201 (4)
H6A	0.7200	0.7675	0.8465	0.024*
H6B	0.4933	0.6823	0.8396	0.024*
C7	0.4797 (3)	0.60208 (18)	0.67239 (14)	0.0185 (4)
H7A	0.3712	0.5496	0.6991	0.022*
H7B	0.5257	0.5577	0.6232	0.022*
C8	0.3916 (3)	0.69016 (19)	0.64249 (14)	0.0185 (4)
H8A	0.4950	0.7371	0.6101	0.022*
H8B	0.2684	0.6521	0.6043	0.022*
O1	1.0470 (2)	0.48871 (13)	0.77274 (9)	0.0169 (3)
O2	1.0471 (2)	0.66537 (12)	0.82508 (9)	0.0148 (3)
O3	0.6122 (2)	0.48861 (14)	0.83124 (10)	0.0204 (3)
O4	0.4782 (2)	0.36214 (14)	0.91348 (10)	0.0233 (4)
C9	1.1854 (3)	0.55782 (16)	0.97230 (12)	0.0115 (4)
H9A	1.3129	0.5973	0.9530	0.014*
C10	1.0075 (3)	0.53211 (15)	0.91992 (12)	0.0100 (4)
C11	0.8194 (3)	0.47309 (16)	0.94750 (12)	0.0109 (4)
C12	1.0312 (3)	0.56437 (16)	0.83241 (12)	0.0113 (4)
C13	0.6225 (3)	0.44016 (17)	0.89245 (12)	0.0131 (4)
O5	0.5182 (2)	1.11219 (12)	0.59735 (10)	0.0182 (3)
O6	0.3881 (2)	0.94917 (13)	0.64244 (10)	0.0197 (3)
O7	−0.0392 (2)	0.94673 (12)	0.71610 (9)	0.0152 (3)
O8	−0.0657 (2)	0.77912 (12)	0.63610 (9)	0.0145 (3)
C14	0.1873 (3)	1.06607 (16)	0.47969 (12)	0.0108 (4)
H14A	0.3161	1.1113	0.4657	0.013*
C15	0.1797 (3)	1.00875 (16)	0.54829 (12)	0.0105 (4)
C16	−0.0101 (3)	0.94157 (16)	0.56864 (12)	0.0104 (4)
C17	0.3760 (3)	1.02308 (17)	0.60026 (12)	0.0121 (4)
C18	−0.0362 (3)	0.88465 (17)	0.64644 (12)	0.0116 (4)
O1S	0.8540 (4)	0.15919 (16)	0.03938 (14)	0.0422 (5)
H1SA	0.7441	0.1645	0.0207	0.051*
H1SB	0.8898	0.2148	0.0766	0.051*
O2S	0.2052 (3)	0.36605 (15)	0.52006 (11)	0.0276 (4)
H2SA	0.1274	0.4049	0.5358	0.033*
H2SB	0.1364	0.3266	0.4783	0.033*
O3S	0.5686 (3)	0.33661 (14)	0.57282 (12)	0.0276 (4)
H3SA	0.4566	0.3418	0.5565	0.033*
H3SB	0.5433	0.2694	0.5763	0.033*
O4S	0.9503 (3)	0.49208 (14)	0.60483 (10)	0.0234 (4)
H4SA	0.9722	0.4923	0.6553	0.028*
H4SB	0.8329	0.4518	0.5922	0.028*
O5SA	0.4646 (6)	0.1816 (3)	−0.0094 (3)	0.0453 (12)*	0.663 (9)
O6SA	0.2705 (5)	1.0084 (3)	0.8494 (2)	0.0431 (10)*	0.666 (6)
O5SB	0.5326 (8)	0.1596 (4)	−0.0451 (4)	0.0246 (18)*	0.337 (9)
O6SB	0.8058 (10)	0.9423 (5)	0.9689 (4)	0.0419 (19)*	0.334 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0127 (8)	0.0119 (8)	0.0179 (9)	0.0019 (6)	−0.0054 (6)	0.0000 (6)
N2	0.0115 (8)	0.0146 (8)	0.0145 (8)	0.0011 (6)	−0.0032 (6)	0.0012 (6)
C1	0.0127 (9)	0.0178 (10)	0.0215 (10)	0.0020 (8)	0.0012 (8)	0.0017 (8)
C2	0.0164 (10)	0.0172 (10)	0.0144 (9)	0.0025 (8)	−0.0003 (8)	0.0038 (8)
C3	0.0131 (9)	0.0173 (10)	0.0163 (10)	0.0030 (8)	0.0007 (7)	0.0023 (8)
C4	0.0180 (10)	0.0130 (9)	0.0135 (9)	0.0035 (8)	−0.0020 (7)	0.0019 (7)
N3	0.0121 (8)	0.0212 (9)	0.0236 (9)	0.0048 (7)	0.0015 (7)	0.0137 (7)
N4	0.0123 (8)	0.0236 (9)	0.0200 (9)	0.0068 (7)	0.0031 (7)	0.0133 (7)
C5	0.0163 (10)	0.0213 (11)	0.0205 (10)	0.0024 (8)	0.0016 (8)	0.0082 (8)
C6	0.0148 (10)	0.0303 (12)	0.0172 (10)	0.0063 (9)	−0.0003 (8)	0.0094 (9)
C7	0.0141 (10)	0.0201 (10)	0.0224 (11)	0.0034 (8)	0.0007 (8)	0.0088 (8)
C8	0.0143 (10)	0.0240 (11)	0.0184 (10)	0.0032 (8)	−0.0008 (8)	0.0103 (8)
O1	0.0226 (8)	0.0186 (7)	0.0100 (7)	0.0064 (6)	−0.0002 (6)	0.0027 (5)
O2	0.0152 (7)	0.0153 (7)	0.0152 (7)	0.0032 (5)	0.0020 (5)	0.0080 (5)
O3	0.0152 (7)	0.0261 (8)	0.0202 (8)	0.0006 (6)	−0.0046 (6)	0.0138 (6)
O4	0.0137 (7)	0.0287 (9)	0.0237 (8)	−0.0066 (6)	−0.0078 (6)	0.0154 (7)
C9	0.0104 (9)	0.0118 (9)	0.0125 (9)	0.0025 (7)	0.0007 (7)	0.0037 (7)
C10	0.0117 (9)	0.0095 (8)	0.0095 (8)	0.0032 (7)	0.0007 (7)	0.0031 (7)
C11	0.0110 (9)	0.0102 (8)	0.0117 (9)	0.0025 (7)	−0.0009 (7)	0.0027 (7)
C12	0.0064 (8)	0.0153 (9)	0.0117 (9)	0.0010 (7)	−0.0013 (7)	0.0042 (7)
C13	0.0109 (9)	0.0155 (9)	0.0127 (9)	0.0026 (7)	−0.0007 (7)	0.0038 (7)
O5	0.0132 (7)	0.0163 (7)	0.0238 (8)	−0.0008 (6)	−0.0068 (6)	0.0082 (6)
O6	0.0133 (7)	0.0232 (8)	0.0260 (8)	0.0039 (6)	−0.0004 (6)	0.0162 (6)
O7	0.0181 (7)	0.0159 (7)	0.0118 (7)	0.0040 (6)	0.0007 (5)	0.0042 (5)
O8	0.0153 (7)	0.0127 (7)	0.0169 (7)	0.0040 (5)	0.0023 (5)	0.0066 (5)
C14	0.0093 (8)	0.0107 (8)	0.0126 (9)	0.0022 (7)	0.0010 (7)	0.0034 (7)
C15	0.0092 (9)	0.0105 (8)	0.0121 (9)	0.0028 (7)	−0.0002 (7)	0.0023 (7)
C16	0.0129 (9)	0.0095 (8)	0.0098 (8)	0.0041 (7)	0.0009 (7)	0.0023 (7)
C17	0.0109 (9)	0.0157 (9)	0.0107 (9)	0.0049 (7)	0.0010 (7)	0.0033 (7)
C18	0.0066 (8)	0.0154 (9)	0.0142 (9)	0.0027 (7)	0.0003 (7)	0.0073 (7)
O1S	0.0552 (13)	0.0269 (10)	0.0427 (12)	0.0156 (9)	0.0075 (10)	−0.0071 (8)
O2S	0.0277 (9)	0.0299 (9)	0.0262 (9)	0.0132 (7)	−0.0097 (7)	−0.0012 (7)
O3S	0.0208 (8)	0.0188 (8)	0.0422 (10)	0.0022 (6)	−0.0072 (7)	0.0076 (7)
O4S	0.0250 (8)	0.0263 (8)	0.0159 (7)	−0.0003 (7)	−0.0050 (6)	0.0069 (6)

N1—C1	1.488 (3)	C7—H7B	0.9900
N1—C4	1.489 (3)	C8—H8A	0.9900
N1—H1C	0.9200	C8—H8B	0.9900
N1—H1D	0.9200	O1—C12	1.258 (2)
N2—C3	1.489 (3)	O2—C12	1.259 (2)
N2—C2	1.492 (3)	O3—C13	1.241 (2)
N2—H2C	0.9200	O4—C13	1.268 (2)
N2—H2D	0.9200	C9—C10	1.393 (3)
C1—C2	1.516 (3)	C9—C11i	1.396 (3)
C1—H1A	0.9900	C9—H9A	0.9500
C1—H1B	0.9900	C10—C11	1.398 (3)
C2—H2A	0.9900	C10—C12	1.515 (3)
C2—H2B	0.9900	C11—C9i	1.396 (3)
C3—C4	1.514 (3)	C11—C13	1.512 (3)
C3—H3A	0.9900	O5—C17	1.266 (2)
C3—H3B	0.9900	O6—C17	1.244 (2)
C4—H4A	0.9900	O7—C18	1.256 (2)
C4—H4B	0.9900	O8—C18	1.260 (2)
N3—C8	1.492 (3)	C14—C16ii	1.392 (3)
N3—C5	1.493 (3)	C14—C15	1.396 (3)
N3—H3C	0.9200	C14—H14A	0.9500
N3—H3D	0.9200	C15—C16	1.401 (3)
N4—C7	1.491 (3)	C15—C17	1.513 (3)
N4—C6	1.494 (3)	C16—C14ii	1.392 (3)
N4—H4C	0.9200	C16—C18	1.517 (3)
N4—H4D	0.9200	O1S—H1SA	0.8201
C5—C6	1.508 (3)	O1S—H1SB	0.8200
C5—H5A	0.9900	O2S—H2SA	0.8197
C5—H5B	0.9900	O2S—H2SB	0.8206
C6—H6A	0.9900	O3S—H3SA	0.8199
C6—H6B	0.9900	O3S—H3SB	0.8201
C7—C8	1.516 (3)	O4S—H4SA	0.8201
C7—H7A	0.9900	O4S—H4SB	0.8201
C1—N1—C4	111.54 (15)	H5A—C5—H5B	108.0
C1—N1—H1C	109.3	N4—C6—C5	111.00 (17)
C4—N1—H1C	109.3	N4—C6—H6A	109.4
C1—N1—H1D	109.3	C5—C6—H6A	109.4
C4—N1—H1D	109.3	N4—C6—H6B	109.4
H1C—N1—H1D	108.0	C5—C6—H6B	109.4
C3—N2—C2	111.88 (16)	H6A—C6—H6B	108.0
C3—N2—H2C	109.2	N4—C7—C8	110.76 (18)
C2—N2—H2C	109.2	N4—C7—H7A	109.5
C3—N2—H2D	109.2	C8—C7—H7A	109.5
C2—N2—H2D	109.2	N4—C7—H7B	109.5
H2C—N2—H2D	107.9	C8—C7—H7B	109.5
N1—C1—C2	110.14 (17)	H7A—C7—H7B	108.1
N1—C1—H1A	109.6	N3—C8—C7	111.08 (17)
C2—C1—H1A	109.6	N3—C8—H8A	109.4
N1—C1—H1B	109.6	C7—C8—H8A	109.4
C2—C1—H1B	109.6	N3—C8—H8B	109.4
H1A—C1—H1B	108.1	C7—C8—H8B	109.4
N2—C2—C1	109.93 (16)	H8A—C8—H8B	108.0
N2—C2—H2A	109.7	C10—C9—C11i	121.56 (18)
C1—C2—H2A	109.7	C10—C9—H9A	119.2
N2—C2—H2B	109.7	C11i—C9—H9A	119.2
C1—C2—H2B	109.7	C9—C10—C11	119.63 (17)
H2A—C2—H2B	108.2	C9—C10—C12	117.35 (17)
N2—C3—C4	109.19 (16)	C11—C10—C12	122.92 (17)
N2—C3—H3A	109.8	C9i—C11—C10	118.81 (17)
C4—C3—H3A	109.8	C9i—C11—C13	119.25 (17)
N2—C3—H3B	109.8	C10—C11—C13	121.93 (17)
C4—C3—H3B	109.8	O1—C12—O2	124.58 (18)
H3A—C3—H3B	108.3	O1—C12—C10	116.78 (17)
N1—C4—C3	109.85 (16)	O2—C12—C10	118.47 (17)
N1—C4—H4A	109.7	O3—C13—O4	124.84 (18)
C3—C4—H4A	109.7	O3—C13—C11	119.64 (17)
N1—C4—H4B	109.7	O4—C13—C11	115.51 (17)
C3—C4—H4B	109.7	C16ii—C14—C15	121.44 (17)
H4A—C4—H4B	108.2	C16ii—C14—H14A	119.3
C8—N3—C5	111.59 (16)	C15—C14—H14A	119.3
C8—N3—H3C	109.3	C14—C15—C16	119.25 (17)
C5—N3—H3C	109.3	C14—C15—C17	119.16 (17)
C8—N3—H3D	109.3	C16—C15—C17	121.57 (17)
C5—N3—H3D	109.3	C14ii—C16—C15	119.31 (17)
H3C—N3—H3D	108.0	C14ii—C16—C18	117.57 (17)
C7—N4—C6	111.34 (16)	C15—C16—C18	122.87 (17)
C7—N4—H4C	109.4	O6—C17—O5	124.55 (18)
C6—N4—H4C	109.4	O6—C17—C15	119.42 (17)
C7—N4—H4D	109.4	O5—C17—C15	116.03 (16)
C6—N4—H4D	109.4	O7—C18—O8	125.13 (18)
H4C—N4—H4D	108.0	O7—C18—C16	116.50 (17)
N3—C5—C6	110.95 (18)	O8—C18—C16	118.21 (17)
N3—C5—H5A	109.4	H1SA—O1S—H1SB	102.8
C6—C5—H5A	109.4	H2SA—O2S—H2SB	98.8
N3—C5—H5B	109.4	H3SA—O3S—H3SB	102.2
C6—C5—H5B	109.4	H4SA—O4S—H4SB	106.6
C4—N1—C1—C2	−57.4 (2)	C9—C10—C12—O2	−79.7 (2)
C3—N2—C2—C1	−57.4 (2)	C11—C10—C12—O2	103.9 (2)
N1—C1—C2—N2	55.7 (2)	C9i—C11—C13—O3	162.78 (19)
C2—N2—C3—C4	58.4 (2)	C10—C11—C13—O3	−18.3 (3)
C1—N1—C4—C3	58.7 (2)	C9i—C11—C13—O4	−17.7 (3)
N2—C3—C4—N1	−57.9 (2)	C10—C11—C13—O4	161.22 (19)
C8—N3—C5—C6	−55.5 (2)	C16ii—C14—C15—C16	0.4 (3)
C7—N4—C6—C5	−56.4 (2)	C16ii—C14—C15—C17	−178.07 (17)
N3—C5—C6—N4	55.7 (2)	C14—C15—C16—C14ii	−0.4 (3)
C6—N4—C7—C8	56.0 (2)	C17—C15—C16—C14ii	178.04 (17)
C5—N3—C8—C7	55.3 (2)	C14—C15—C16—C18	−174.45 (18)
N4—C7—C8—N3	−55.3 (2)	C17—C15—C16—C18	3.9 (3)
C11i—C9—C10—C11	−0.6 (3)	C14—C15—C17—O6	−157.34 (19)
C11i—C9—C10—C12	−177.06 (17)	C16—C15—C17—O6	24.3 (3)
C9—C10—C11—C9i	0.6 (3)	C14—C15—C17—O5	22.9 (3)
C12—C10—C11—C9i	176.84 (17)	C16—C15—C17—O5	−155.48 (18)
C9—C10—C11—C13	−178.33 (17)	C14ii—C16—C18—O7	−97.7 (2)
C12—C10—C11—C13	−2.1 (3)	C15—C16—C18—O7	76.5 (2)
C9—C10—C12—O1	95.7 (2)	C14ii—C16—C18—O8	78.0 (2)
C11—C10—C12—O1	−80.6 (2)	C15—C16—C18—O8	−107.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O5iii	0.92	1.74	2.642 (2)	166
N1—H1D···O7iv	0.92	1.84	2.763 (2)	178
N2—H2C···O1v	0.92	1.82	2.723 (2)	165
N2—H2D···O4	0.92	1.72	2.635 (2)	179
N3—H3C···O2v	0.92	1.90	2.787 (2)	163
N3—H3D···O6	0.92	1.92	2.690 (2)	141
N4—H4C···O8vi	0.92	1.85	2.753 (2)	168
N4—H4D···O3	0.92	2.00	2.748 (2)	138
O1S—H1SA···O5SA	0.82	2.02	2.837 (2)	172
O1S—H1SA···O5SA	0.82	2.02	2.837 (2)	172
O1S—H1SB···O2vii	0.82	1.95	2.763 (2)	172
O2S—H2SA···O4Sv	0.82	2.04	2.839 (2)	165
O2S—H2SB···O8viii	0.82	2.05	2.835 (2)	160
O3S—H3SA···O2S	0.82	1.90	2.722 (2)	176
O3S—H3SB···O5iv	0.82	2.00	2.817 (2)	171
O4S—H4SA···O1	0.82	1.95	2.772 (2)	175
O4S—H4SB···O3S	0.82	1.95	2.764 (2)	170
C5—H5A···O6SA	0.99	2.50	3.288 (4)	136
C5—H5B···O7vi	0.99	2.35	3.272 (3)	154
C7—H7A···O1v	0.99	2.48	3.414 (3)	156
C8—H8B···O4Sv	0.99	2.51	3.299 (3)	137
C4—H4B···Cg1iv	0.99	2.64	3.518 (2)	148
C4—H4B···Cg1viii	0.99	2.64	3.518 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O5i	0.92	1.74	2.642 (2)	166
N1—H1D⋯O7ii	0.92	1.84	2.763 (2)	178
N2—H2C⋯O1iii	0.92	1.82	2.723 (2)	165
N2—H2D⋯O4	0.92	1.72	2.635 (2)	179
N3—H3C⋯O2iii	0.92	1.90	2.787 (2)	163
N3—H3D⋯O6	0.92	1.92	2.690 (2)	141
N4—H4C⋯O8iv	0.92	1.85	2.753 (2)	168
N4—H4D⋯O3	0.92	2.00	2.748 (2)	138
O1S—H1SA⋯O5SA	0.82	2.02	2.837 (2)	172
O1S—H1SA⋯O5SA	0.82	2.02	2.837 (2)	172
O1S—H1SB⋯O2v	0.82	1.95	2.763 (2)	172
O2S—H2SA⋯O4Siii	0.82	2.04	2.839 (2)	165
O2S—H2SB⋯O8vi	0.82	2.05	2.835 (2)	160
O3S—H3SA⋯O2S	0.82	1.90	2.722 (2)	176
O3S—H3SB⋯O5ii	0.82	2.00	2.817 (2)	171
O4S—H4SA⋯O1	0.82	1.95	2.772 (2)	175
O4S—H4SB⋯O3S	0.82	1.95	2.764 (2)	170
C5—H5A⋯O6SA	0.99	2.50	3.288 (4)	136
C5—H5B⋯O7iv	0.99	2.35	3.272 (3)	154
C7—H7A⋯O1iii	0.99	2.48	3.414 (3)	156
C8—H8B⋯O4Siii	0.99	2.51	3.299 (3)	137
C4—H4B⋯Cg1ii	0.99	2.64	3.518 (2)	148
C4—H4B⋯Cg1vi	0.99	2.64	3.518 (2)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the C14,C15,C16,C14′,C15′,C16′ benzene ring.