3-Amino­pyridinium 4-hydr­oxy-3-iodo­naphthalene-1-sulfonate dihydrate

Liu, Y.; Li, J.

doi:10.1107/S1600536808014098

organic compounds

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Volume 64| Part 6| June 2008| Page o1109

doi:10.1107/S1600536808014098

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3-Aminopyridinium 4-hydroxy-3-iodonaphthalene-1-sulfonate dihydrate

Yun Liu ^a and Jie Li ^a ^*

^aBasic Experiment Teaching Center, Henan University, Kaifeng 475001, People's Republic of China
^*Correspondence e-mail: lijiehd@163.com

(Received 12 April 2008; accepted 11 May 2008; online 17 May 2008)

In the hydrated title salt, C₅H₇N₂⁺·C₁₀H₆IO₄S⁻·2H₂O, the component species are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming an infinite three-dimensional framework.

Related literature

For background, see: Li (2007 ).

Experimental

Crystal data

C₅H₇N₂⁺·C₁₀H₆IO₄S⁻·2H₂O
M_r = 480.27
Monoclinic, P 2₁ /n
a = 15.0219 (6) Å
b = 6.9917 (3) Å
c = 18.0729 (7) Å
β = 110.868 (1)°
V = 1773.66 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 296 (2) K
0.18 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.720, T_max = 0.828
17926 measured reflections
3484 independent reflections
3128 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.069
S = 1.08
3484 reflections
258 parameters
34 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2W	0.882 (10)	1.853 (13)	2.725 (4)	170 (4)
N2—H2B⋯O1	0.886 (10)	2.232 (16)	3.085 (3)	162 (4)
N2—H2C⋯O2ⁱ	0.888 (10)	2.179 (11)	3.064 (4)	175 (3)
O4—H4⋯O1W	0.843 (10)	1.89 (2)	2.655 (3)	150 (4)
O1W—H1WB⋯O3ⁱⁱ	0.847 (10)	1.983 (12)	2.822 (3)	171 (4)
O1W—H1WA⋯O4ⁱⁱⁱ	0.851 (10)	2.158 (15)	2.944 (3)	153 (3)
O2W—H2WA⋯O1^iv	0.853 (10)	1.981 (12)	2.820 (3)	167 (3)
O2W—H2WB⋯O2^v	0.856 (10)	1.944 (11)	2.796 (3)	173 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z; (iv) -x+1, -y, -z; (v) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014098/hb2719sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014098/hb2719Isup2.hkl

checkCIF report

Comment top

This work continues our previous synthetic and structural studies of the hydrogen bonding interactions between various organic acids and substituted pyridines (Li, 2007).

The asymmetric unit of the title salt, (I), is composed of one 3-aminopyridinium cation, one 8-hydroxy-7-iodo-5-quinolinesulfonate anion and two water molecules (Fig. 1). One water molecule (O1W), acting as a hydrogen bonding donor interacts with the hydroxy oxygen (O4) acting as hydrogen bonding acceptor (Table 1). The other water molecule (O2W) and the 3-aminopyridinium cation are linked by a N1—H1A···O2W hydrogen bond. Moreover, the cation and anion are linked together by a N2—H2B···O1 hydrogen bond. Overall, an infinite three-dimensional framework results (Fig. 2).

Related literature top

For background, see: Li (2007).

Experimental top

A 5-ml ethanol solution of 3-aminopyridine (1.0 mmol, 0.094 g) was added to a 20-ml hot aqueous solution of 8-hydroxy-7-iodo-5-quinolinesulfonic acid (1.0 mmol, 0.351 g) and the mixture was stirred for 20 minutes at 373 K. Then the solution was filtered, and the filtrate was kept at the room temperature. After two weeks, yellow blocks of (I) were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids for the non-H atoms are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Part of the packing of (I) viewed along the direction [010]. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.

3-Aminopyridinium 4-hydroxy-3-iodonaphthalene-1-sulfonate dihydrate top

Crystal data top

C₅H₇N₂⁺·C₁₀H₆IO₄S⁻·2H₂O	F(000) = 952
M_r = 480.27	D_x = 1.799 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9093 reflections
a = 15.0219 (6) Å	θ = 2.4–27.7°
b = 6.9917 (3) Å	µ = 1.96 mm⁻¹
c = 18.0729 (7) Å	T = 296 K
β = 110.868 (1)°	Block, yellow
V = 1773.66 (12) Å³	0.18 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3484 independent reflections
Radiation source: fine-focus sealed tube	3128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→18
T_min = 0.720, T_max = 0.828	k = −8→8
17926 measured reflections	l = −22→22

Refinement top

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0364P)² + 1.4355P] where P = (F_o² + 2F_c²)/3
3484 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.71 e Å⁻³
34 restraints	Δρ_min = −0.96 e Å⁻³

Crystal data top

C₅H₇N₂⁺·C₁₀H₆IO₄S⁻·2H₂O	V = 1773.66 (12) Å³
M_r = 480.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.0219 (6) Å	µ = 1.96 mm⁻¹
b = 6.9917 (3) Å	T = 296 K
c = 18.0729 (7) Å	0.18 × 0.12 × 0.10 mm
β = 110.868 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	3484 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3128 reflections with I > 2σ(I)
T_min = 0.720, T_max = 0.828	R_int = 0.027
17926 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	34 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.71 e Å⁻³
3484 reflections	Δρ_min = −0.96 e Å⁻³
258 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.7208 (2)	0.1965 (4)	−0.01736 (18)	0.0486 (7)
H1A	0.6708 (18)	0.233 (5)	−0.0582 (16)	0.056 (11)*
N2	0.7670 (2)	0.0577 (5)	0.18478 (18)	0.0614 (8)
H2B	0.7069 (11)	0.034 (6)	0.179 (2)	0.065 (11)*
H2C	0.8150 (18)	0.008 (5)	0.2246 (15)	0.059 (10)*
C11	0.8061 (3)	0.1948 (5)	−0.0234 (2)	0.0564 (9)
H11A	0.8135	0.2277	−0.0708	0.068*
C12	0.8834 (2)	0.1434 (5)	0.0416 (2)	0.0577 (9)
H12A	0.9438	0.1405	0.0384	0.069*
C13	0.8718 (2)	0.0965 (5)	0.1112 (2)	0.0541 (8)
H13A	0.9245	0.0618	0.1550	0.065*
C14	0.7811 (2)	0.1006 (4)	0.11680 (19)	0.0433 (7)
C15	0.7058 (2)	0.1516 (4)	0.0493 (2)	0.0447 (7)
H15A	0.6443	0.1547	0.0502	0.054*
S1	0.51967 (4)	0.21097 (9)	0.19020 (4)	0.03081 (15)
I1	0.159514 (12)	0.20253 (3)	0.230170 (10)	0.03822 (8)
O1	0.54976 (13)	0.0659 (3)	0.14622 (13)	0.0469 (5)
O2	0.55842 (13)	0.3982 (3)	0.18257 (13)	0.0469 (5)
O3	0.53822 (15)	0.1580 (4)	0.27109 (13)	0.0570 (6)
O4	0.10004 (13)	0.2998 (3)	0.04865 (12)	0.0393 (5)
H4	0.080 (3)	0.315 (6)	−0.0008 (7)	0.071 (13)*
C1	0.39401 (17)	0.2327 (4)	0.14385 (15)	0.0273 (5)
C2	0.33925 (18)	0.2092 (3)	0.18943 (15)	0.0285 (5)
H2A	0.3682	0.1784	0.2427	0.034*
C3	0.24002 (18)	0.2308 (4)	0.15712 (15)	0.0281 (5)
C4	0.19533 (17)	0.2770 (3)	0.07873 (15)	0.0275 (5)
C5	0.25099 (18)	0.3043 (3)	0.03008 (15)	0.0275 (5)
C6	0.20225 (16)	0.3533 (3)	−0.04661 (13)	0.0230 (5)
H6	0.1364	0.3671	−0.0655	0.028*
C7	0.2508 (2)	0.3803 (4)	−0.09292 (16)	0.0399 (6)
H7	0.2179	0.4140	−0.1454	0.048*
C8	0.3502 (2)	0.3611 (5)	−0.06744 (17)	0.0423 (7)
H8	0.3818	0.3819	−0.1027	0.051*
C9	0.4003 (2)	0.3120 (4)	0.00897 (17)	0.0371 (6)
H9	0.4661	0.2985	0.0262	0.045*
C10	0.35128 (18)	0.2815 (3)	0.06225 (15)	0.0275 (5)
O1W	−0.02157 (17)	0.3572 (4)	−0.09765 (13)	0.0532 (6)
H1WA	−0.038 (2)	0.473 (2)	−0.095 (2)	0.060 (5)*
H1WB	0.002 (2)	0.359 (4)	−0.1337 (16)	0.056 (5)*
O2W	0.55451 (16)	0.2736 (3)	−0.13855 (17)	0.0555 (6)
H2WA	0.5162 (18)	0.179 (3)	−0.147 (2)	0.059 (11)*
H2WB	0.5167 (18)	0.370 (3)	−0.151 (2)	0.072 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0482 (16)	0.0385 (14)	0.0518 (16)	−0.0003 (12)	0.0091 (13)	0.0011 (12)
N2	0.0386 (16)	0.090 (2)	0.0548 (17)	0.0127 (16)	0.0150 (14)	0.0124 (16)
C11	0.063 (2)	0.0483 (19)	0.064 (2)	−0.0091 (16)	0.0302 (19)	0.0008 (16)
C12	0.0395 (17)	0.060 (2)	0.080 (3)	−0.0068 (15)	0.0282 (18)	0.0007 (19)
C13	0.0307 (15)	0.058 (2)	0.068 (2)	0.0012 (14)	0.0112 (15)	0.0044 (17)
C14	0.0321 (14)	0.0431 (16)	0.0531 (17)	0.0027 (12)	0.0129 (13)	−0.0010 (14)
C15	0.0316 (14)	0.0430 (16)	0.0580 (19)	0.0040 (12)	0.0142 (14)	0.0016 (14)
S1	0.0198 (3)	0.0380 (3)	0.0329 (3)	0.0003 (2)	0.0073 (2)	0.0048 (3)
I1	0.03151 (12)	0.05175 (14)	0.03694 (12)	0.00166 (7)	0.01898 (8)	0.00622 (8)
O1	0.0299 (10)	0.0489 (12)	0.0630 (13)	0.0051 (9)	0.0180 (9)	−0.0058 (10)
O2	0.0289 (10)	0.0424 (11)	0.0616 (13)	−0.0083 (9)	0.0066 (9)	0.0054 (10)
O3	0.0303 (11)	0.0986 (19)	0.0378 (11)	0.0063 (11)	0.0069 (9)	0.0226 (12)
O4	0.0214 (9)	0.0645 (14)	0.0313 (11)	0.0048 (8)	0.0084 (8)	0.0037 (9)
C1	0.0206 (11)	0.0297 (12)	0.0318 (13)	0.0004 (9)	0.0095 (10)	0.0015 (10)
C2	0.0258 (12)	0.0323 (13)	0.0261 (12)	0.0011 (10)	0.0078 (10)	0.0036 (10)
C3	0.0249 (12)	0.0336 (13)	0.0297 (12)	−0.0003 (10)	0.0144 (10)	0.0007 (10)
C4	0.0214 (12)	0.0318 (12)	0.0297 (12)	0.0013 (10)	0.0095 (10)	−0.0014 (10)
C5	0.0255 (12)	0.0278 (12)	0.0296 (12)	−0.0006 (9)	0.0101 (10)	−0.0019 (9)
C6	0.0162 (10)	0.0326 (12)	0.0178 (10)	0.0005 (9)	0.0030 (8)	0.0016 (9)
C7	0.0390 (15)	0.0479 (16)	0.0289 (13)	−0.0033 (13)	0.0075 (11)	0.0030 (12)
C8	0.0375 (15)	0.0600 (18)	0.0342 (14)	−0.0037 (14)	0.0188 (12)	0.0049 (13)
C9	0.0274 (13)	0.0495 (16)	0.0362 (14)	−0.0016 (12)	0.0135 (12)	0.0028 (12)
C10	0.0248 (12)	0.0285 (12)	0.0288 (12)	−0.0015 (9)	0.0092 (10)	−0.0006 (10)
O1W	0.0462 (12)	0.0741 (16)	0.0393 (12)	0.0129 (12)	0.0151 (10)	0.0012 (11)
O2W	0.0377 (12)	0.0424 (13)	0.0792 (18)	0.0006 (10)	0.0122 (12)	−0.0025 (12)

Geometric parameters (Å, º) top

N1—C11	1.325 (5)	C1—C2	1.366 (4)
N1—C15	1.339 (4)	C1—C10	1.424 (4)
N1—H1A	0.882 (10)	C2—C3	1.402 (4)
N2—C14	1.353 (4)	C2—H2A	0.9300
N2—H2B	0.886 (10)	C3—C4	1.373 (4)
N2—H2C	0.888 (10)	C4—C5	1.425 (4)
C11—C12	1.374 (5)	C5—C6	1.361 (3)
C11—H11A	0.9300	C5—C10	1.417 (4)
C12—C13	1.369 (5)	C6—C7	1.305 (4)
C12—H12A	0.9300	C6—H6	0.9300
C13—C14	1.403 (4)	C7—C8	1.404 (4)
C13—H13A	0.9300	C7—H7	0.9300
C14—C15	1.382 (4)	C8—C9	1.360 (4)
C15—H15A	0.9300	C8—H8	0.9300
S1—O3	1.436 (2)	C9—C10	1.421 (4)
S1—O1	1.456 (2)	C9—H9	0.9300
S1—O2	1.459 (2)	O1W—H1WA	0.851 (10)
S1—C1	1.778 (2)	O1W—H1WB	0.847 (10)
I1—C3	2.093 (2)	O2W—H2WA	0.853 (10)
O4—C4	1.347 (3)	O2W—H2WB	0.856 (10)
O4—H4	0.843 (10)

C11—N1—C15	123.4 (3)	C10—C1—S1	121.29 (19)
C11—N1—H1A	120 (3)	C1—C2—C3	121.0 (2)
C15—N1—H1A	117 (3)	C1—C2—H2A	119.5
C14—N2—H2B	115 (2)	C3—C2—H2A	119.5
C14—N2—H2C	119 (2)	C4—C3—C2	120.8 (2)
H2B—N2—H2C	122 (4)	C4—C3—I1	119.55 (18)
N1—C11—C12	118.6 (4)	C2—C3—I1	119.64 (19)
N1—C11—H11A	120.7	O4—C4—C3	120.2 (2)
C12—C11—H11A	120.7	O4—C4—C5	120.5 (2)
C13—C12—C11	120.3 (3)	C3—C4—C5	119.3 (2)
C13—C12—H12A	119.9	C6—C5—C10	123.6 (2)
C11—C12—H12A	119.9	C6—C5—C4	116.2 (2)
C12—C13—C14	120.4 (3)	C10—C5—C4	120.2 (2)
C12—C13—H13A	119.8	C7—C6—C5	118.0 (2)
C14—C13—H13A	119.8	C7—C6—H6	121.0
N2—C14—C15	121.0 (3)	C5—C6—H6	121.0
N2—C14—C13	122.1 (3)	C6—C7—C8	123.2 (3)
C15—C14—C13	116.9 (3)	C6—C7—H7	118.4
N1—C15—C14	120.5 (3)	C8—C7—H7	118.4
N1—C15—H15A	119.8	C9—C8—C7	119.7 (3)
C14—C15—H15A	119.8	C9—C8—H8	120.1
O3—S1—O1	113.00 (15)	C7—C8—H8	120.1
O3—S1—O2	112.85 (15)	C8—C9—C10	119.6 (3)
O1—S1—O2	111.19 (13)	C8—C9—H9	120.2
O3—S1—C1	106.86 (12)	C10—C9—H9	120.2
O1—S1—C1	106.64 (12)	C5—C10—C9	115.9 (2)
O2—S1—C1	105.73 (12)	C5—C10—C1	118.2 (2)
C4—O4—H4	111 (3)	C9—C10—C1	125.9 (2)
C2—C1—C10	120.5 (2)	H1WA—O1W—H1WB	103.8 (15)
C2—C1—S1	118.17 (19)	H2WA—O2W—H2WB	102.6 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2W	0.88 (1)	1.85 (1)	2.725 (4)	170 (4)
N2—H2B···O1	0.89 (1)	2.23 (2)	3.085 (3)	162 (4)
N2—H2C···O2ⁱ	0.89 (1)	2.18 (1)	3.064 (4)	175 (3)
O4—H4···O1W	0.84 (1)	1.89 (2)	2.655 (3)	150 (4)
O1W—H1WB···O3ⁱⁱ	0.85 (1)	1.98 (1)	2.822 (3)	171 (4)
O1W—H1WA···O4ⁱⁱⁱ	0.85 (1)	2.16 (2)	2.944 (3)	153 (3)
O2W—H2WA···O1^iv	0.85 (1)	1.98 (1)	2.820 (3)	167 (3)
O2W—H2WB···O2^v	0.86 (1)	1.94 (1)	2.796 (3)	173 (3)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₅H₇N₂⁺·C₁₀H₆IO₄S⁻·2H₂O
M_r	480.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	15.0219 (6), 6.9917 (3), 18.0729 (7)
β (°)	110.868 (1)
V (Å³)	1773.66 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.720, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	17926, 3484, 3128
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.069, 1.08
No. of reflections	3484
No. of parameters	258
No. of restraints	34
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.96

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2W	0.882 (10)	1.853 (13)	2.725 (4)	170 (4)
N2—H2B···O1	0.886 (10)	2.232 (16)	3.085 (3)	162 (4)
N2—H2C···O2ⁱ	0.888 (10)	2.179 (11)	3.064 (4)	175 (3)
O4—H4···O1W	0.843 (10)	1.89 (2)	2.655 (3)	150 (4)
O1W—H1WB···O3ⁱⁱ	0.847 (10)	1.983 (12)	2.822 (3)	171 (4)
O1W—H1WA···O4ⁱⁱⁱ	0.851 (10)	2.158 (15)	2.944 (3)	153 (3)
O2W—H2WA···O1^iv	0.853 (10)	1.981 (12)	2.820 (3)	167 (3)
O2W—H2WB···O2^v	0.856 (10)	1.944 (11)	2.796 (3)	173 (3)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z.

References

Bruker (2001). SADABS, SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Li, J. (2007). Acta Cryst. E63, o4171. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 6| June 2008| Page o1109

doi:10.1107/S1600536808014098

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