Hexa-kis-(propyl-ammonium) benzene-1,2,4,5-tetra-carboxyl-ate 2,5-dicarb-oxy-benzene-1,4-carboxyl-ate tetra-hydrate.

The title organic salt, 6C(3)H(10)N(+)·C(10)H(2)O(8) (4-)·C(10)H(4)O(8) (2-)·4H(2)O, contains seven independent entities in the asymmetric unit which comprises three propyl-ammonium cations, two water mol-ecules, half a 2,5-dicarb-oxy-benzene-1,4-carboxyl-ate dianion (H(2)btc(2-)) and half a benzene-1,2,4,5-tetra-carboxyl-ate tetra-anion (btc(4-)), the latter two anions being located about centres of inversion. One of the water mol-ecules is disordered over two positions in a 0.55 (2):0.45 (2) ratio. The combination of mol-ecular ions and water mol-ecules results in an extensive and complex three-dimensional network of hydrogen bonds, the network being made up of nine unique N-H⋯O inter-actions between the ammonium cations and the anions, as well as four unique O-H⋯O inter-actions between the water mol-ecules and the anions.

Related literature

For studies involving hydrogen-bonding inter­actions, see: Pimentel & McClellan (1960 ▶); Lemmerer (2011 ▶); Arora & Pedireddi (2003 ▶); Biradha & Zaworotko (1998 ▶). For graph-set motifs in crystal structures, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

6C3H10N+·C10H2O8 4−·C10H4O8 2−·4H2O

M = 935.03

Triclinic,

a = 9.9826 (2) Å

b = 11.0994 (2) Å

c = 12.4453 (2) Å

α = 107.461 (1)°

β = 90.062 (1)°

γ = 105.721 (1)°

V = 1261.10 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.55 × 0.33 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

41269 measured reflections

6092 independent reflections

4741 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.10

6092 reflections

359 parameters

36 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and SCHAKAL99 (Keller, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036501/bh2430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036501/bh2430Isup2.hkl

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

6C3H10N+·C10H2O84−·C10H4O82−·4H2O	Z = 1
Mr = 935.03	F(000) = 504
Triclinic, P1	Dx = 1.231 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9826 (2) Å	Cell parameters from 8121 reflections
b = 11.0994 (2) Å	θ = 2.2–27.2°
c = 12.4453 (2) Å	µ = 0.10 mm−1
α = 107.461 (1)°	T = 173 K
β = 90.062 (1)°	Block, colourless
γ = 105.721 (1)°	0.55 × 0.33 × 0.06 mm
V = 1261.10 (4) Å3

Bruker APEXII CCD diffractometer	4741 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
Graphite monochromator	θmax = 28.0°, θmin = 1.7°
φ and ω scans	h = −13→13
41269 measured reflections	k = −14→14
6092 independent reflections	l = −16→16

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: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.0131P] where P = (Fo2 + 2Fc2)/3
6092 reflections	(Δ/σ)max < 0.001
359 parameters	Δρmax = 0.40 e Å−3
36 restraints	Δρmin = −0.21 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.22708 (12)	0.52580 (12)	−0.14299 (10)	0.0232 (2)
C2A	0.11213 (11)	0.51156 (11)	−0.06610 (9)	0.0200 (2)
C3A	0.12378 (11)	0.47733 (11)	0.03189 (9)	0.0205 (2)
C4A	0.25248 (12)	0.44589 (12)	0.06613 (10)	0.0244 (2)
C5A	0.01039 (11)	0.46641 (11)	0.09698 (9)	0.0211 (2)
H5A	0.0172	0.4434	0.1640	0.025*
O1A	0.33910 (9)	0.62170 (11)	−0.09776 (8)	0.0409 (3)
O2A	0.20978 (11)	0.45663 (10)	−0.24006 (8)	0.0426 (3)
O3A	0.28839 (9)	0.48363 (9)	0.17124 (7)	0.0290 (2)
O4A	0.31169 (11)	0.38559 (12)	−0.00919 (8)	0.0481 (3)
H1A	0.410 (2)	0.627 (2)	−0.1536 (17)	0.073 (6)*
C1B	0.54388 (12)	0.25468 (10)	0.46362 (9)	0.0198 (2)
C2B	0.51859 (11)	0.12374 (10)	0.48550 (9)	0.0177 (2)
C3B	0.38802 (11)	0.05553 (10)	0.50875 (9)	0.0179 (2)
C4B	0.26512 (11)	0.11247 (10)	0.52874 (9)	0.0194 (2)
C5B	0.37135 (11)	−0.06751 (10)	0.52237 (9)	0.0185 (2)
H5B	0.2825	−0.1145	0.5374	0.022*
O1B	0.27743 (8)	0.21010 (8)	0.61637 (6)	0.02247 (18)
O2B	0.15747 (9)	0.05801 (9)	0.46345 (8)	0.0351 (2)
O3B	0.66579 (9)	0.33107 (8)	0.49001 (8)	0.0317 (2)
O4B	0.44488 (8)	0.27684 (8)	0.41868 (7)	0.02546 (19)
C6C	1.00660 (13)	0.14661 (13)	0.78897 (10)	0.0302 (3)
H6A	1.0776	0.2198	0.8437	0.036*
H6B	1.0366	0.0657	0.7751	0.036*
C7C	0.86828 (17)	0.1274 (2)	0.83874 (14)	0.0518 (4)
H7A	0.7957	0.0592	0.7818	0.062*
H7B	0.8419	0.2107	0.8583	0.062*
C8C	0.8738 (3)	0.0858 (3)	0.94401 (18)	0.0825 (7)
H8A	0.8858	−0.0028	0.9229	0.124*
H8B	0.7865	0.0856	0.9800	0.124*
H8C	0.9526	0.1479	0.9970	0.124*
N1C	0.99833 (11)	0.17678 (10)	0.68130 (9)	0.0237 (2)
H1B	1.0887 (13)	0.1969 (15)	0.6545 (12)	0.041 (4)*
H1C	0.9581 (15)	0.2445 (13)	0.6863 (13)	0.039 (4)*
H1D	0.9397 (15)	0.1009 (13)	0.6289 (11)	0.042 (4)*
C6D	0.51159 (14)	0.19783 (14)	0.81853 (11)	0.0342 (3)
H6C	0.5811	0.2313	0.8851	0.041*
H6D	0.5588	0.1649	0.7506	0.041*
C7D	0.39438 (16)	0.08625 (15)	0.83184 (13)	0.0429 (4)
H7C	0.3219	0.0568	0.7678	0.051*
H7D	0.3511	0.1179	0.9024	0.051*
C8D	0.4457 (2)	−0.02982 (18)	0.83571 (15)	0.0575 (5)
H8D	0.4885	−0.0615	0.7658	0.086*
H8E	0.3666	−0.1009	0.8431	0.086*
H8F	0.5151	−0.0017	0.9007	0.086*
N1D	0.45926 (11)	0.30762 (11)	0.80741 (9)	0.0308 (2)
H1G	0.5358 (15)	0.3796 (14)	0.8062 (13)	0.044 (4)*
H1E	0.4074 (17)	0.3349 (17)	0.8726 (12)	0.056 (5)*
H1F	0.4011 (15)	0.2756 (15)	0.7358 (10)	0.041 (4)*
C6E	0.11925 (13)	0.35625 (13)	0.48083 (10)	0.0287 (3)
H6E	0.0610	0.4160	0.5112	0.034*
H6F	0.0832	0.2764	0.5041	0.034*
C7E	0.10636 (16)	0.31785 (16)	0.35439 (12)	0.0434 (4)
H7E	0.1654	0.2589	0.3237	0.052*
H7F	0.1405	0.3977	0.3308	0.052*
C8E	−0.04440 (17)	0.24798 (18)	0.30615 (14)	0.0538 (4)
H8G	−0.0790	0.1700	0.3308	0.081*
H8H	−0.0493	0.2210	0.2234	0.081*
H8I	−0.1020	0.3079	0.3332	0.081*
N1E	0.26635 (11)	0.42296 (10)	0.53008 (9)	0.0240 (2)
H1H	0.2706 (18)	0.4358 (17)	0.6115 (10)	0.054 (5)*
H1I	0.3266 (14)	0.3730 (14)	0.4935 (12)	0.038 (4)*
H1J	0.2960 (15)	0.5099 (11)	0.5212 (11)	0.032 (4)*
O1W	0.82657 (12)	0.33934 (11)	0.67230 (10)	0.0453 (3)
H1WA	0.7720 (18)	0.3259 (17)	0.6042 (15)	0.055 (5)*
H1WB	0.7964 (18)	0.3927 (19)	0.7282 (15)	0.056 (5)*
O2WA	0.5131 (5)	0.6023 (11)	0.7471 (7)	0.0361 (15)	0.55 (2)
O2WB	0.5446 (9)	0.6686 (15)	0.7894 (10)	0.042 (2)	0.45 (2)
H2WA	0.534 (2)	0.662 (2)	0.7082 (18)	0.070 (6)*
H2WB	0.589 (2)	0.606 (2)	0.7792 (17)	0.056 (5)*

	U11	U22	U33	U12	U13	U23
C1A	0.0222 (6)	0.0280 (6)	0.0230 (6)	0.0108 (5)	0.0057 (4)	0.0098 (5)
C2A	0.0189 (5)	0.0224 (5)	0.0172 (5)	0.0067 (4)	0.0027 (4)	0.0035 (4)
C3A	0.0192 (5)	0.0227 (6)	0.0185 (5)	0.0071 (4)	0.0008 (4)	0.0038 (4)
C4A	0.0205 (5)	0.0312 (6)	0.0247 (6)	0.0097 (5)	0.0031 (4)	0.0113 (5)
C5A	0.0215 (5)	0.0247 (6)	0.0173 (5)	0.0075 (4)	0.0013 (4)	0.0061 (4)
O1A	0.0236 (5)	0.0557 (6)	0.0325 (5)	−0.0013 (4)	0.0075 (4)	0.0093 (5)
O2A	0.0454 (6)	0.0454 (6)	0.0258 (5)	0.0064 (5)	0.0159 (4)	0.0005 (4)
O3A	0.0256 (4)	0.0408 (5)	0.0241 (4)	0.0149 (4)	−0.0009 (3)	0.0104 (4)
O4A	0.0478 (6)	0.0829 (8)	0.0320 (5)	0.0482 (6)	0.0138 (4)	0.0180 (5)
C1B	0.0254 (6)	0.0176 (5)	0.0188 (5)	0.0095 (4)	0.0049 (4)	0.0062 (4)
C2B	0.0209 (5)	0.0161 (5)	0.0169 (5)	0.0069 (4)	0.0021 (4)	0.0045 (4)
C3B	0.0202 (5)	0.0168 (5)	0.0168 (5)	0.0073 (4)	0.0005 (4)	0.0036 (4)
C4B	0.0190 (5)	0.0168 (5)	0.0247 (5)	0.0061 (4)	0.0040 (4)	0.0088 (4)
C5B	0.0186 (5)	0.0168 (5)	0.0199 (5)	0.0046 (4)	0.0036 (4)	0.0059 (4)
O1B	0.0239 (4)	0.0215 (4)	0.0227 (4)	0.0110 (3)	0.0034 (3)	0.0039 (3)
O2B	0.0233 (4)	0.0268 (5)	0.0467 (5)	0.0094 (4)	−0.0095 (4)	−0.0029 (4)
O3B	0.0302 (5)	0.0196 (4)	0.0453 (5)	0.0012 (4)	−0.0054 (4)	0.0156 (4)
O4B	0.0277 (4)	0.0292 (4)	0.0293 (4)	0.0152 (4)	0.0071 (3)	0.0169 (4)
C6C	0.0317 (7)	0.0317 (7)	0.0294 (6)	0.0119 (5)	0.0014 (5)	0.0103 (5)
C7C	0.0448 (9)	0.0760 (12)	0.0487 (9)	0.0236 (8)	0.0202 (7)	0.0341 (9)
C8C	0.0876 (15)	0.121 (2)	0.0633 (13)	0.0335 (14)	0.0300 (11)	0.0605 (14)
N1C	0.0218 (5)	0.0231 (5)	0.0249 (5)	0.0074 (4)	0.0028 (4)	0.0044 (4)
C6D	0.0303 (7)	0.0449 (8)	0.0270 (6)	0.0162 (6)	0.0000 (5)	0.0059 (6)
C7D	0.0480 (9)	0.0474 (9)	0.0357 (7)	0.0175 (7)	0.0105 (6)	0.0130 (7)
C8D	0.0827 (13)	0.0550 (10)	0.0442 (9)	0.0288 (9)	0.0124 (9)	0.0212 (8)
N1D	0.0248 (5)	0.0359 (6)	0.0268 (6)	0.0090 (5)	0.0018 (4)	0.0024 (5)
C6E	0.0285 (6)	0.0297 (6)	0.0328 (7)	0.0115 (5)	0.0082 (5)	0.0140 (5)
C7E	0.0422 (8)	0.0494 (9)	0.0337 (7)	−0.0008 (7)	0.0014 (6)	0.0182 (7)
C8E	0.0459 (9)	0.0584 (10)	0.0482 (9)	0.0011 (8)	−0.0083 (7)	0.0161 (8)
N1E	0.0296 (5)	0.0201 (5)	0.0264 (5)	0.0104 (4)	0.0062 (4)	0.0100 (4)
O1W	0.0521 (6)	0.0462 (6)	0.0359 (6)	0.0330 (5)	−0.0143 (5)	−0.0066 (5)
O2WA	0.0229 (13)	0.063 (4)	0.042 (2)	0.0199 (17)	0.0125 (14)	0.038 (3)
O2WB	0.032 (2)	0.072 (5)	0.048 (3)	0.030 (3)	0.020 (2)	0.042 (4)

C1A—O2A	1.2041 (14)	N1C—H1C	0.930 (12)
C1A—O1A	1.3017 (15)	N1C—H1D	0.938 (11)
C1A—C2A	1.5007 (15)	C6D—N1D	1.4910 (18)
C2A—C5Ai	1.3859 (15)	C6D—C7D	1.506 (2)
C2A—C3A	1.3953 (15)	C6D—H6C	0.9900
C3A—C5A	1.3923 (15)	C6D—H6D	0.9900
C3A—C4A	1.5117 (16)	C7D—C8D	1.523 (2)
C4A—O4A	1.2309 (15)	C7D—H7C	0.9900
C4A—O3A	1.2665 (14)	C7D—H7D	0.9900
C5A—C2Ai	1.3859 (15)	C8D—H8D	0.9800
C5A—H5A	0.9500	C8D—H8E	0.9800
O1A—H1A	1.00 (2)	C8D—H8F	0.9800
C1B—O4B	1.2504 (13)	N1D—H1G	0.948 (12)
C1B—O3B	1.2572 (14)	N1D—H1E	0.978 (12)
C1B—C2B	1.5128 (15)	N1D—H1F	0.977 (11)
C2B—C5Bii	1.3933 (15)	C6E—N1E	1.4889 (16)
C2B—C3B	1.3976 (15)	C6E—C7E	1.4973 (18)
C3B—C5B	1.3920 (15)	C6E—H6E	0.9900
C3B—C4B	1.5142 (14)	C6E—H6F	0.9900
C4B—O2B	1.2376 (14)	C7E—C8E	1.521 (2)
C4B—O1B	1.2638 (13)	C7E—H7E	0.9900
C5B—C2Bii	1.3933 (15)	C7E—H7F	0.9900
C5B—H5B	0.9500	C8E—H8G	0.9800
C6C—N1C	1.4827 (15)	C8E—H8H	0.9800
C6C—C7C	1.5024 (19)	C8E—H8I	0.9800
C6C—H6A	0.9900	N1E—H1H	0.979 (12)
C6C—H6B	0.9900	N1E—H1I	0.952 (11)
C7C—C8C	1.519 (2)	N1E—H1J	0.970 (11)
C7C—H7A	0.9900	O1W—H1WA	0.958 (19)
C7C—H7B	0.9900	O1W—H1WB	0.880 (19)
C8C—H8A	0.9800	O2WA—H2WA	0.91 (2)
C8C—H8B	0.9800	O2WA—H2WB	0.84 (2)
C8C—H8C	0.9800	O2WB—H2WA	1.00 (2)
N1C—H1B	0.955 (12)	O2WB—H2WB	0.89 (2)
O2A—C1A—O1A	124.64 (11)	H1B—N1C—H1D	109.4 (13)
O2A—C1A—C2A	120.64 (11)	H1C—N1C—H1D	106.6 (13)
O1A—C1A—C2A	114.60 (10)	N1D—C6D—C7D	111.46 (11)
C5Ai—C2A—C3A	120.07 (10)	N1D—C6D—H6C	109.3
C5Ai—C2A—C1A	116.65 (10)	C7D—C6D—H6C	109.3
C3A—C2A—C1A	123.27 (10)	N1D—C6D—H6D	109.3
C5A—C3A—C2A	118.52 (10)	C7D—C6D—H6D	109.3
C5A—C3A—C4A	119.36 (10)	H6C—C6D—H6D	108.0
C2A—C3A—C4A	122.06 (10)	C6D—C7D—C8D	111.73 (13)
O4A—C4A—O3A	126.02 (11)	C6D—C7D—H7C	109.3
O4A—C4A—C3A	117.91 (10)	C8D—C7D—H7C	109.3
O3A—C4A—C3A	116.06 (10)	C6D—C7D—H7D	109.3
C2Ai—C5A—C3A	121.40 (10)	C8D—C7D—H7D	109.3
C2Ai—C5A—H5A	119.3	H7C—C7D—H7D	107.9
C3A—C5A—H5A	119.3	C7D—C8D—H8D	109.5
C1A—O1A—H1A	110.4 (11)	C7D—C8D—H8E	109.5
O4B—C1B—O3B	125.49 (10)	H8D—C8D—H8E	109.5
O4B—C1B—C2B	118.29 (10)	C7D—C8D—H8F	109.5
O3B—C1B—C2B	116.19 (9)	H8D—C8D—H8F	109.5
C5Bii—C2B—C3B	119.25 (10)	H8E—C8D—H8F	109.5
C5Bii—C2B—C1B	118.35 (9)	C6D—N1D—H1G	109.7 (10)
C3B—C2B—C1B	122.35 (10)	C6D—N1D—H1E	108.3 (11)
C5B—C3B—C2B	118.92 (10)	H1G—N1D—H1E	109.5 (14)
C5B—C3B—C4B	117.47 (9)	C6D—N1D—H1F	107.8 (9)
C2B—C3B—C4B	123.45 (9)	H1G—N1D—H1F	109.1 (13)
O2B—C4B—O1B	123.98 (10)	H1E—N1D—H1F	112.5 (14)
O2B—C4B—C3B	119.26 (10)	N1E—C6E—C7E	112.22 (10)
O1B—C4B—C3B	116.65 (9)	N1E—C6E—H6E	109.2
C3B—C5B—C2Bii	121.83 (10)	C7E—C6E—H6E	109.2
C3B—C5B—H5B	119.1	N1E—C6E—H6F	109.2
C2Bii—C5B—H5B	119.1	C7E—C6E—H6F	109.2
N1C—C6C—C7C	111.51 (11)	H6E—C6E—H6F	107.9
N1C—C6C—H6A	109.3	C6E—C7E—C8E	111.17 (13)
C7C—C6C—H6A	109.3	C6E—C7E—H7E	109.4
N1C—C6C—H6B	109.3	C8E—C7E—H7E	109.4
C7C—C6C—H6B	109.3	C6E—C7E—H7F	109.4
H6A—C6C—H6B	108.0	C8E—C7E—H7F	109.4
C6C—C7C—C8C	111.48 (15)	H7E—C7E—H7F	108.0
C6C—C7C—H7A	109.3	C7E—C8E—H8G	109.5
C8C—C7C—H7A	109.3	C7E—C8E—H8H	109.5
C6C—C7C—H7B	109.3	H8G—C8E—H8H	109.5
C8C—C7C—H7B	109.3	C7E—C8E—H8I	109.5
H7A—C7C—H7B	108.0	H8G—C8E—H8I	109.5
C7C—C8C—H8A	109.5	H8H—C8E—H8I	109.5
C7C—C8C—H8B	109.5	C6E—N1E—H1H	108.8 (10)
H8A—C8C—H8B	109.5	C6E—N1E—H1I	110.5 (9)
C7C—C8C—H8C	109.5	H1H—N1E—H1I	111.7 (13)
H8A—C8C—H8C	109.5	C6E—N1E—H1J	109.6 (9)
H8B—C8C—H8C	109.5	H1H—N1E—H1J	106.8 (13)
C6C—N1C—H1B	110.5 (9)	H1I—N1E—H1J	109.4 (12)
C6C—N1C—H1C	113.5 (9)	H1WA—O1W—H1WB	107.7 (15)
H1B—N1C—H1C	110.0 (13)	H2WA—O2WA—H2WB	106.7 (19)
C6C—N1C—H1D	106.7 (9)	H2WA—O2WB—H2WB	96 (2)
O2A—C1A—C2A—C5Ai	−60.87 (16)	O4B—C1B—C2B—C3B	−30.62 (15)
O1A—C1A—C2A—C5Ai	115.26 (12)	O3B—C1B—C2B—C3B	151.27 (11)
O2A—C1A—C2A—C3A	118.78 (14)	C5Bii—C2B—C3B—C5B	−0.60 (17)
O1A—C1A—C2A—C3A	−65.09 (15)	C1B—C2B—C3B—C5B	176.82 (9)
C5Ai—C2A—C3A—C5A	−0.15 (18)	C5Bii—C2B—C3B—C4B	174.69 (9)
C1A—C2A—C3A—C5A	−179.80 (10)	C1B—C2B—C3B—C4B	−7.88 (16)
C5Ai—C2A—C3A—C4A	176.98 (10)	C5B—C3B—C4B—O2B	−66.68 (14)
C1A—C2A—C3A—C4A	−2.66 (17)	C2B—C3B—C4B—O2B	117.96 (12)
C5A—C3A—C4A—O4A	140.12 (12)	C5B—C3B—C4B—O1B	109.48 (11)
C2A—C3A—C4A—O4A	−36.99 (17)	C2B—C3B—C4B—O1B	−65.87 (14)
C5A—C3A—C4A—O3A	−39.17 (16)	C2B—C3B—C5B—C2Bii	0.62 (17)
C2A—C3A—C4A—O3A	143.72 (11)	C4B—C3B—C5B—C2Bii	−174.96 (9)
C2A—C3A—C5A—C2Ai	0.16 (18)	N1C—C6C—C7C—C8C	175.47 (16)
C4A—C3A—C5A—C2Ai	−177.05 (10)	N1D—C6D—C7D—C8D	176.37 (11)
O4B—C1B—C2B—C5Bii	146.82 (10)	N1E—C6E—C7E—C8E	179.07 (13)
O3B—C1B—C2B—C5Bii	−31.29 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1C—H1C···O1W	0.93 (1)	1.93 (1)	2.8293 (14)	162 (1)
N1D—H1F···O1B	0.98 (1)	1.77 (1)	2.7387 (14)	172 (1)
N1E—H1I···O4B	0.95 (1)	1.87 (1)	2.8197 (13)	179 (1)
N1C—H1B···O1Biii	0.96 (1)	1.92 (1)	2.8598 (13)	167 (1)
N1C—H1D···O2Bii	0.94 (1)	1.80 (1)	2.7269 (13)	171 (1)
N1D—H1G···O3Aiv	0.95 (1)	1.94 (1)	2.8725 (14)	167 (2)
N1D—H1E···O4Av	0.98 (1)	1.79 (1)	2.7642 (14)	179 (2)
N1E—H1H···O2Av	0.98 (1)	1.91 (1)	2.8493 (14)	159 (2)
N1E—H1J···O3Biv	0.97 (1)	1.75 (1)	2.7170 (13)	174 (1)
O1W—H1WB···O3Aiv	0.880 (19)	1.94 (2)	2.8107 (14)	169.2 (17)
O1W—H1WA···O3B	0.958 (19)	1.796 (19)	2.7421 (14)	169.1 (16)
O1A—H1A···O2WBvi	1.00 (2)	1.54 (2)	2.513 (4)	163.1 (19)
O1A—H1A···O2WAvi	1.00 (2)	1.62 (2)	2.598 (5)	168.4 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1C—H1C⋯O1W	0.93 (1)	1.93 (1)	2.8293 (14)	162 (1)
N1D—H1F⋯O1B	0.98 (1)	1.77 (1)	2.7387 (14)	172 (1)
N1E—H1I⋯O4B	0.95 (1)	1.87 (1)	2.8197 (13)	179 (1)
N1C—H1B⋯O1B i	0.96 (1)	1.92 (1)	2.8598 (13)	167 (1)
N1C—H1D⋯O2B ii	0.94 (1)	1.80 (1)	2.7269 (13)	171 (1)
N1D—H1G⋯O3A iii	0.95 (1)	1.94 (1)	2.8725 (14)	167 (2)
N1D—H1E⋯O4A iv	0.98 (1)	1.79 (1)	2.7642 (14)	179 (2)
N1E—H1H⋯O2A iv	0.98 (1)	1.91 (1)	2.8493 (14)	159 (2)
N1E—H1J⋯O3B iii	0.97 (1)	1.75 (1)	2.7170 (13)	174 (1)
O1W—H1WB⋯O3A iii	0.880 (19)	1.94 (2)	2.8107 (14)	169.2 (17)
O1W—H1WA⋯O3B	0.958 (19)	1.796 (19)	2.7421 (14)	169.1 (16)
O1A—H1A⋯O2WB v	1.00 (2)	1.54 (2)	2.513 (4)	163.1 (19)
O1A—H1A⋯O2WA v	1.00 (2)	1.62 (2)	2.598 (5)	168.4 (19)

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