Poly[[penta-aqua-(μ(4)-pyridine-2,4,6-tri-carboxyl-ato)(μ(3)-pyridine-2,4,6-tri-carboxyl-ato)disamarium(III)] mono-hydrate].

The asymmetric unit of the title compound, {[Sm(2)(C(8)H(2)NO(6))(2)(H(2)O)(5)]·H(2)O}(n), contains two independent Sm(III) ions, two pyridine-2,4,6-tricarboxyl-ate (ptc) ligands, five aqua ligands and one lattice water mol-ecule. One Sm(III) ion is nine-coordinated by one N and five O atoms from the three ptc ligands and three aqua ligands in a distorted monocapped square antiprismatic geometry, and the other is eight-coordinated by one N and five O atoms from three ptc ligands and two aqua ligands in a 4,4'-bicapped trigonal anti-prismatic geometry. The ptc ligands brigde the Sm(III) ions into a three-dimensional polymeric framework. Extensive O-H⋯O hydrogen bonding is observed in the crystal structure.

Related literature

For related compounds, see: Gao et al. (2006 ▶); Ghosh & Bharadwaj (2005 ▶); Li et al. (2008 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

[Sm2(C8H2NO6)2(H2O)5]·H2O

M = 825.01

Monoclinic,

a = 18.426 (4) Å

b = 6.9082 (14) Å

c = 18.583 (4) Å

β = 111.98 (3)°

V = 2193.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 5.40 mm−1

T = 293 K

0.43 × 0.28 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.177, T max = 0.321

20300 measured reflections

4963 independent reflections

4776 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.041

S = 1.19

4963 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.84 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002462/cv5233sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002462/cv5233Isup2.hkl

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

[Sm2(C8H2NO6)2(H2O)5]·H2O	F(000) = 1576
Mr = 825.01	Dx = 2.498 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19369 reflections
a = 18.426 (4) Å	θ = 3.2–27.5°
b = 6.9082 (14) Å	µ = 5.40 mm−1
c = 18.583 (4) Å	T = 293 K
β = 111.98 (3)°	Block, colorless
V = 2193.6 (8) Å3	0.43 × 0.28 × 0.21 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4963 independent reflections
Radiation source: fine-focus sealed tube	4776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −23→23
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −8→8
Tmin = 0.177, Tmax = 0.321	l = −24→22
20300 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)] = 0.018	H-atom parameters constrained
wR(F2) = 0.041	w = 1/[σ2(Fo2) + (0.0066P)2 + 3.5019P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max = 0.002
4963 reflections	Δρmax = 0.69 e Å−3
344 parameters	Δρmin = −0.84 e Å−3
0 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: 0.00244 (6)

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
Sm1	0.373309 (7)	0.222784 (18)	0.378119 (7)	0.01049 (4)
Sm2	0.374965 (8)	0.250031 (17)	0.896720 (7)	0.01111 (5)
N1	0.42996 (13)	0.3322 (3)	0.27802 (12)	0.0125 (4)
C1	0.38355 (15)	0.4105 (3)	0.21147 (15)	0.0127 (5)
C2	0.40694 (15)	0.4323 (3)	0.14877 (15)	0.0139 (5)
H2A	0.3735	0.4861	0.1023	0.017*
C3	0.48176 (15)	0.3710 (3)	0.15774 (15)	0.0125 (5)
C4	0.53246 (15)	0.3029 (4)	0.22948 (15)	0.0136 (5)
H4A	0.5840	0.2707	0.2377	0.016*
C5	0.50357 (15)	0.2846 (3)	0.28859 (15)	0.0119 (5)
C6	0.30319 (15)	0.4640 (4)	0.20964 (15)	0.0145 (5)
O1	0.26044 (11)	0.5719 (3)	0.15807 (11)	0.0185 (4)
O2	0.28618 (11)	0.3912 (3)	0.26427 (11)	0.0206 (4)
C7	0.50797 (15)	0.3719 (3)	0.08959 (14)	0.0124 (5)
O3	0.45938 (12)	0.3160 (3)	0.02671 (11)	0.0219 (4)
O4	0.57737 (11)	0.4236 (3)	0.10278 (11)	0.0172 (4)
C8	0.55086 (16)	0.2082 (4)	0.36836 (16)	0.0146 (5)
O5	0.62134 (12)	0.1852 (3)	0.38807 (12)	0.0278 (5)
O6	0.51110 (11)	0.1716 (3)	0.41069 (11)	0.0183 (4)
O7	0.36682 (12)	−0.0503 (3)	0.29113 (11)	0.0220 (4)
H7B	0.3178	−0.0743	0.2654	0.026*
H7A	0.3869	−0.0502	0.2585	0.026*
O8	0.40849 (13)	0.5640 (3)	0.39790 (13)	0.0267 (5)
H8A	0.4563	0.6135	0.4218	0.032*
H8B	0.3682	0.5986	0.4083	0.032*
O9	0.37653 (13)	−0.0753 (3)	0.45208 (12)	0.0232 (4)
H9A	0.4159	−0.0992	0.4946	0.028*
H9B	0.3363	−0.1166	0.4672	0.028*
N2	0.38147 (13)	0.2822 (3)	0.76366 (13)	0.0126 (4)
C9	0.31935 (15)	0.3494 (3)	0.70511 (15)	0.0136 (5)
C10	0.31717 (16)	0.3588 (4)	0.62931 (15)	0.0164 (5)
H10A	0.2726	0.4017	0.5888	0.020*
C11	0.38335 (16)	0.3023 (4)	0.61614 (15)	0.0144 (5)
C12	0.44856 (17)	0.2360 (3)	0.67751 (16)	0.0142 (5)
H12A	0.4938	0.2004	0.6699	0.017*
C13	0.44461 (16)	0.2242 (3)	0.75073 (16)	0.0135 (5)
C14	0.25231 (16)	0.4146 (4)	0.72805 (15)	0.0148 (5)
O10	0.19320 (12)	0.4815 (3)	0.67583 (11)	0.0210 (4)
O11	0.26175 (12)	0.3950 (3)	0.79795 (11)	0.0232 (4)
C15	0.38312 (17)	0.3038 (4)	0.53467 (15)	0.0157 (5)
O12	0.44658 (13)	0.2832 (3)	0.52504 (12)	0.0221 (4)
O13	0.31898 (12)	0.3173 (3)	0.47848 (11)	0.0212 (4)
C16	0.50960 (15)	0.1461 (3)	0.82233 (15)	0.0134 (5)
O14	0.57112 (12)	0.0880 (3)	0.81788 (11)	0.0206 (4)
O15	0.49458 (12)	0.1467 (3)	0.88390 (11)	0.0198 (4)
O16	0.39568 (13)	−0.0498 (3)	0.97353 (11)	0.0244 (4)
H16B	0.4251	−0.0676	1.0162	0.029*
H16A	0.3898	−0.1564	0.9530	0.029*
O17	0.28096 (12)	0.3100 (3)	0.95460 (13)	0.0283 (5)
H17B	0.2358	0.3132	0.9261	0.034*
H17A	0.2806	0.2465	0.9929	0.034*
O18	0.21204 (15)	0.6072 (3)	0.41898 (14)	0.0374 (6)
H18B	0.2389	0.5106	0.4367	0.045*
H18A	0.1688	0.5550	0.3908	0.045*

	U11	U22	U33	U12	U13	U23
Sm1	0.00985 (8)	0.01369 (7)	0.00821 (7)	0.00008 (4)	0.00368 (6)	0.00015 (4)
Sm2	0.00839 (8)	0.01720 (7)	0.00731 (7)	−0.00064 (4)	0.00243 (6)	−0.00005 (4)
N1	0.0109 (11)	0.0167 (10)	0.0101 (10)	0.0002 (8)	0.0040 (9)	0.0003 (8)
C1	0.0095 (12)	0.0143 (11)	0.0133 (12)	0.0001 (9)	0.0032 (10)	0.0017 (9)
C2	0.0132 (13)	0.0169 (11)	0.0101 (12)	−0.0002 (9)	0.0026 (10)	0.0028 (9)
C3	0.0128 (13)	0.0136 (11)	0.0118 (12)	−0.0032 (9)	0.0055 (10)	−0.0006 (9)
C4	0.0108 (13)	0.0162 (11)	0.0144 (13)	−0.0015 (9)	0.0055 (11)	−0.0011 (10)
C5	0.0115 (13)	0.0128 (10)	0.0111 (12)	−0.0005 (9)	0.0041 (11)	0.0002 (9)
C6	0.0113 (13)	0.0184 (12)	0.0133 (12)	0.0010 (9)	0.0042 (10)	−0.0015 (10)
O1	0.0137 (10)	0.0243 (9)	0.0164 (10)	0.0060 (7)	0.0045 (8)	0.0061 (8)
O2	0.0128 (10)	0.0339 (10)	0.0171 (10)	0.0053 (8)	0.0079 (8)	0.0105 (8)
C7	0.0137 (13)	0.0127 (10)	0.0105 (12)	0.0009 (9)	0.0044 (10)	0.0024 (9)
O3	0.0208 (11)	0.0313 (10)	0.0112 (10)	−0.0046 (8)	0.0031 (9)	−0.0038 (8)
O4	0.0150 (10)	0.0224 (9)	0.0158 (9)	−0.0015 (7)	0.0077 (8)	0.0010 (7)
C8	0.0127 (13)	0.0158 (11)	0.0140 (13)	0.0001 (9)	0.0036 (11)	−0.0002 (10)
O5	0.0108 (11)	0.0466 (13)	0.0235 (12)	0.0054 (9)	0.0035 (9)	0.0103 (10)
O6	0.0137 (10)	0.0295 (10)	0.0121 (9)	0.0051 (8)	0.0053 (8)	0.0073 (8)
O7	0.0143 (10)	0.0353 (11)	0.0188 (10)	−0.0037 (8)	0.0090 (9)	−0.0115 (9)
O8	0.0268 (12)	0.0190 (9)	0.0329 (12)	−0.0045 (8)	0.0098 (10)	−0.0050 (8)
O9	0.0273 (12)	0.0248 (10)	0.0169 (10)	0.0035 (8)	0.0074 (9)	0.0062 (8)
N2	0.0114 (11)	0.0163 (9)	0.0095 (11)	0.0000 (8)	0.0033 (9)	0.0004 (8)
C9	0.0136 (13)	0.0157 (11)	0.0113 (12)	0.0018 (9)	0.0044 (10)	0.0009 (9)
C10	0.0168 (14)	0.0197 (12)	0.0111 (13)	0.0039 (10)	0.0034 (11)	0.0030 (10)
C11	0.0173 (14)	0.0152 (11)	0.0114 (13)	0.0001 (9)	0.0062 (11)	−0.0017 (10)
C12	0.0137 (14)	0.0169 (12)	0.0128 (13)	0.0007 (9)	0.0058 (12)	−0.0007 (9)
C13	0.0131 (14)	0.0140 (11)	0.0133 (13)	−0.0002 (9)	0.0049 (11)	−0.0013 (9)
C14	0.0139 (13)	0.0171 (11)	0.0126 (12)	0.0028 (9)	0.0039 (10)	0.0006 (10)
O10	0.0170 (11)	0.0284 (10)	0.0149 (10)	0.0110 (8)	0.0029 (8)	0.0043 (8)
O11	0.0167 (11)	0.0417 (12)	0.0124 (10)	0.0096 (9)	0.0067 (9)	0.0040 (8)
C15	0.0216 (14)	0.0164 (11)	0.0105 (13)	0.0019 (10)	0.0076 (11)	−0.0003 (10)
O12	0.0175 (11)	0.0370 (11)	0.0136 (10)	0.0003 (8)	0.0077 (9)	−0.0027 (8)
O13	0.0180 (11)	0.0347 (11)	0.0099 (9)	0.0068 (8)	0.0042 (8)	−0.0007 (8)
C16	0.0129 (13)	0.0135 (11)	0.0132 (12)	−0.0016 (9)	0.0042 (10)	0.0001 (9)
O14	0.0137 (10)	0.0303 (10)	0.0194 (10)	0.0067 (8)	0.0079 (9)	0.0014 (8)
O15	0.0152 (10)	0.0336 (10)	0.0113 (9)	0.0068 (8)	0.0057 (8)	0.0043 (8)
O16	0.0297 (12)	0.0225 (10)	0.0140 (10)	0.0053 (8)	0.0002 (9)	0.0034 (8)
O17	0.0111 (11)	0.0532 (13)	0.0215 (11)	0.0062 (9)	0.0071 (9)	0.0058 (10)
O18	0.0347 (15)	0.0383 (13)	0.0323 (13)	0.0133 (10)	0.0046 (11)	−0.0015 (10)

Sm1—O6	2.406 (2)	O3—Sm2vi	2.377 (2)
Sm1—O2	2.422 (2)	O4—Sm2iv	2.4185 (18)
Sm1—O8	2.436 (2)	C8—O5	1.221 (3)
Sm1—O7	2.4582 (19)	C8—O6	1.285 (3)
Sm1—O9	2.4642 (19)	O7—H7B	0.8654
Sm1—O13	2.5110 (18)	O7—H7A	0.8193
Sm1—O1i	2.5243 (19)	O8—H8A	0.8930
Sm1—N1	2.564 (2)	O8—H8B	0.8667
Sm1—O12	2.587 (2)	O9—H9A	0.8662
Sm1—C15	2.901 (3)	O9—H9B	0.9304
Sm2—O10ii	2.3600 (19)	N2—C9	1.333 (3)
Sm2—O3iii	2.377 (2)	N2—C13	1.335 (3)
Sm2—O17	2.3925 (19)	C9—C10	1.396 (3)
Sm2—O15	2.4120 (19)	C9—C14	1.518 (3)
Sm2—O4iv	2.4185 (19)	C10—C11	1.387 (3)
Sm2—O11	2.420 (2)	C10—H10A	0.9300
Sm2—O16	2.463 (2)	C11—C12	1.389 (4)
Sm2—N2	2.530 (2)	C11—C15	1.512 (3)
N1—C1	1.327 (3)	C12—C13	1.392 (4)
N1—C5	1.337 (3)	C12—H12A	0.9300
C1—C2	1.394 (3)	C13—C16	1.518 (4)
C1—C6	1.514 (3)	C14—O10	1.245 (3)
C2—C3	1.391 (4)	C14—O11	1.252 (3)
C2—H2A	0.9300	O10—Sm2vii	2.3600 (19)
C3—C4	1.393 (4)	C15—O13	1.254 (3)
C3—C7	1.515 (3)	C15—O12	1.256 (3)
C4—C5	1.394 (3)	C16—O14	1.234 (3)
C4—H4A	0.9300	C16—O15	1.274 (3)
C5—C8	1.506 (4)	O16—H16B	0.7852
C6—O1	1.237 (3)	O16—H16A	0.8179
C6—O2	1.273 (3)	O17—H17B	0.8023
O1—Sm1v	2.5243 (19)	O17—H17A	0.8383
C7—O3	1.238 (3)	O18—H18B	0.8223
C7—O4	1.260 (3)	O18—H18A	0.8524
O6—Sm1—O2	125.63 (6)	C2—C1—C6	124.1 (2)
O6—Sm1—O8	84.72 (7)	C3—C2—C1	118.0 (2)
O2—Sm1—O8	73.68 (8)	C3—C2—H2A	121.0
O6—Sm1—O7	80.78 (7)	C1—C2—H2A	121.0
O2—Sm1—O7	86.62 (7)	C2—C3—C4	119.8 (2)
O8—Sm1—O7	141.88 (7)	C2—C3—C7	120.7 (2)
O6—Sm1—O9	86.22 (7)	C4—C3—C7	119.5 (2)
O2—Sm1—O9	139.32 (7)	C3—C4—C5	117.9 (2)
O8—Sm1—O9	140.81 (7)	C3—C4—H4A	121.1
O7—Sm1—O9	73.17 (7)	C5—C4—H4A	121.1
O6—Sm1—O13	121.87 (7)	N1—C5—C4	121.8 (2)
O2—Sm1—O13	101.87 (6)	N1—C5—C8	114.3 (2)
O8—Sm1—O13	78.10 (7)	C4—C5—C8	123.8 (2)
O7—Sm1—O13	138.87 (7)	O1—C6—O2	125.5 (2)
O9—Sm1—O13	74.70 (7)	O1—C6—C1	119.9 (2)
O6—Sm1—O1i	147.10 (6)	O2—C6—C1	114.6 (2)
O2—Sm1—O1i	72.76 (7)	C6—O1—Sm1v	136.93 (16)
O8—Sm1—O1i	128.16 (7)	C6—O2—Sm1	127.30 (17)
O7—Sm1—O1i	72.87 (6)	O3—C7—O4	126.5 (2)
O9—Sm1—O1i	67.72 (7)	O3—C7—C3	116.3 (2)
O13—Sm1—O1i	71.60 (7)	O4—C7—C3	117.1 (2)
O6—Sm1—N1	63.12 (7)	C7—O3—Sm2vi	170.38 (18)
O2—Sm1—N1	62.70 (7)	C7—O4—Sm2iv	127.27 (16)
O8—Sm1—N1	70.53 (7)	O5—C8—O6	125.2 (3)
O7—Sm1—N1	71.46 (6)	O5—C8—C5	120.0 (2)
O9—Sm1—N1	136.02 (6)	O6—C8—C5	114.8 (2)
O13—Sm1—N1	147.78 (7)	C8—O6—Sm1	127.38 (17)
O1i—Sm1—N1	123.39 (7)	Sm1—O7—H7B	107.1
O6—Sm1—O12	70.93 (7)	Sm1—O7—H7A	124.1
O2—Sm1—O12	139.30 (7)	H7B—O7—H7A	104.9
O8—Sm1—O12	71.36 (7)	Sm1—O8—H8A	127.1
O7—Sm1—O12	134.07 (7)	Sm1—O8—H8B	95.7
O9—Sm1—O12	69.64 (7)	H8A—O8—H8B	123.4
O13—Sm1—O12	50.94 (7)	Sm1—O9—H9A	120.4
O1i—Sm1—O12	114.82 (7)	Sm1—O9—H9B	124.7
N1—Sm1—O12	121.65 (7)	H9A—O9—H9B	99.0
O6—Sm1—C15	96.45 (8)	C9—N2—C13	119.8 (2)
O2—Sm1—C15	123.75 (7)	C9—N2—Sm2	119.21 (16)
O8—Sm1—C15	75.45 (7)	C13—N2—Sm2	120.87 (18)
O7—Sm1—C15	140.98 (7)	N2—C9—C10	122.1 (2)
O9—Sm1—C15	67.82 (7)	N2—C9—C14	114.5 (2)
O13—Sm1—C15	25.51 (7)	C10—C9—C14	123.4 (2)
O1i—Sm1—C15	92.01 (7)	C11—C10—C9	118.0 (2)
N1—Sm1—C15	141.37 (7)	C11—C10—H10A	121.0
O12—Sm1—C15	25.64 (7)	C9—C10—H10A	121.0
O10ii—Sm2—O3iii	137.50 (7)	C10—C11—C12	119.7 (2)
O10ii—Sm2—O17	94.18 (8)	C10—C11—C15	120.1 (2)
O3iii—Sm2—O17	79.54 (8)	C12—C11—C15	120.1 (2)
O10ii—Sm2—O15	91.23 (7)	C11—C12—C13	118.5 (2)
O3iii—Sm2—O15	83.25 (7)	C11—C12—H12A	120.8
O17—Sm2—O15	159.69 (7)	C13—C12—H12A	120.8
O10ii—Sm2—O4iv	148.20 (7)	N2—C13—C12	121.8 (3)
O3iii—Sm2—O4iv	73.67 (7)	N2—C13—C16	113.8 (2)
O17—Sm2—O4iv	99.20 (7)	C12—C13—C16	124.4 (2)
O15—Sm2—O4iv	86.13 (7)	O10—C14—O11	126.2 (2)
O10ii—Sm2—O11	76.61 (8)	O10—C14—C9	117.2 (2)
O3iii—Sm2—O11	137.89 (7)	O11—C14—C9	116.6 (2)
O17—Sm2—O11	72.89 (7)	C14—O10—Sm2vii	149.34 (19)
O15—Sm2—O11	127.43 (6)	C14—O11—Sm2	125.26 (16)
O4iv—Sm2—O11	79.98 (7)	O13—C15—O12	121.9 (2)
O10ii—Sm2—O16	66.67 (7)	O13—C15—C11	118.9 (2)
O3iii—Sm2—O16	70.83 (7)	O12—C15—C11	119.2 (3)
O17—Sm2—O16	82.31 (7)	O13—C15—Sm1	59.59 (13)
O15—Sm2—O16	81.90 (7)	O12—C15—Sm1	63.06 (14)
O4iv—Sm2—O16	143.57 (7)	C11—C15—Sm1	168.04 (17)
O11—Sm2—O16	133.64 (7)	C15—O12—Sm1	91.30 (17)
O10ii—Sm2—N2	73.77 (7)	C15—O13—Sm1	94.91 (15)
O3iii—Sm2—N2	136.39 (7)	O14—C16—O15	125.1 (3)
O17—Sm2—N2	137.00 (8)	O14—C16—C13	120.0 (2)
O15—Sm2—N2	63.27 (7)	O15—C16—C13	114.9 (2)
O4iv—Sm2—N2	76.81 (6)	C16—O15—Sm2	127.11 (17)
O11—Sm2—N2	64.22 (7)	Sm2—O16—H16B	128.1
O16—Sm2—N2	125.92 (7)	Sm2—O16—H16A	121.5
C1—N1—C5	120.1 (2)	H16B—O16—H16A	104.5
C1—N1—Sm1	120.05 (16)	Sm2—O17—H17B	117.1
C5—N1—Sm1	119.15 (16)	Sm2—O17—H17A	121.9
N1—C1—C2	122.0 (2)	H17B—O17—H17A	103.8
N1—C1—C6	113.8 (2)	H18B—O18—H18A	100.8

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O14viii	0.82	1.87	2.686 (3)	172
O7—H7B···O2i	0.86	1.80	2.645 (3)	165
O8—H8A···O12iv	0.89	1.83	2.727 (3)	177
O8—H8B···O9ix	0.87	2.38	2.831 (3)	113
O9—H9A···O6viii	0.87	1.84	2.698 (3)	171
O9—H9B···O5viii	0.93	2.55	3.052 (3)	114
O16—H16A···O4viii	0.82	2.31	3.075 (3)	157
O16—H16B···O15x	0.79	1.97	2.747 (3)	171
O17—H17A···O18ii	0.84	1.86	2.697 (3)	176
O17—H17B···O5xi	0.80	1.96	2.731 (3)	162
O18—H18A···O14xii	0.85	2.06	2.905 (3)	174
O18—H18B···O13	0.82	1.93	2.736 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O14i	0.82	1.87	2.686 (3)	172
O7—H7B⋯O2ii	0.86	1.80	2.645 (3)	165
O8—H8A⋯O12iii	0.89	1.83	2.727 (3)	177
O8—H8B⋯O9iv	0.87	2.38	2.831 (3)	113
O9—H9A⋯O6i	0.87	1.84	2.698 (3)	171
O9—H9B⋯O5i	0.93	2.55	3.052 (3)	114
O16—H16A⋯O4i	0.82	2.31	3.075 (3)	157
O16—H16B⋯O15v	0.79	1.97	2.747 (3)	171
O17—H17A⋯O18vi	0.84	1.86	2.697 (3)	176
O17—H17B⋯O5vii	0.80	1.96	2.731 (3)	162
O18—H18A⋯O14viii	0.85	2.06	2.905 (3)	174
O18—H18B⋯O13	0.82	1.93	2.736 (3)	168

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