2,2′-[(Biphenyl-4,4′-di­yl)di(ethene-1,2-di­yl)]dibenzene­sulfonic acid–4-methyl­piperidine–water (1/2/2)

Li, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536809026932

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1931

doi:10.1107/S1600536809026932

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2,2′-[(Biphenyl-4,4′-diyl)di(ethene-1,2-diyl)]dibenzenesulfonic acid–4-methylpiperidine–water (1/2/2)

Yu-Feng Li ^a and Fang-Fang Jian ^b ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 24 June 2009; accepted 9 July 2009; online 18 July 2009)

The title compound, C₂₈H₂₂O₆S₂·2C₆H₁₃N·2H₂O, was prepared by the reaction of a Wittig reagent and 2-formylbenzenesulfonic acid. The main molecule lies about an inversion centre at the midpoint of the C—C bond between the inner benzene rings. The molecular conformation is stabilized by intramolecular hydrogen bonds. The crystal structure is further stabilized by O—H⋯O and N—H⋯O hydrogen-bonding interactions.

Related literature

For the optical properties of ethylene biphenyls, see: Song et al. (2003 ). For comparative bond lengths, see: Trueblood et al. (1982 ).

Experimental

Crystal data

C₂₈H₂₂O₆S₂·2(C₆H₁₃N)·2(H₂O)
M_r = 752.96
Monoclinic, P 2₁ /c
a = 14.852 (3) Å
b = 9.7240 (19) Å
c = 14.765 (3) Å
β = 109.76 (3)°
V = 2006.8 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.26 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
4436 measured reflections
4264 independent reflections
1779 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.204
S = 1.01
4264 reflections
243 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O1	0.94 (6)	1.95 (6)	2.881 (5)	171 (6)
N2—H2C⋯O1Wⁱ	0.86	2.23	2.767 (4)	120
N2—H2C⋯O3ⁱⁱ	0.86	2.28	2.787 (5)	117
C2—H2B⋯O3	0.93	2.42	2.838 (5)	107
C7—H7A⋯O2	0.93	2.42	3.103 (5)	130
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026932/at2832sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026932/at2832Isup2.hkl

checkCIF report

Comment top

Ethylene biphenyl have received considerable attention in the literature. They are attractive from several points of view, such as the optics characteristic. (Song et al., 2003). As part of our search for new ethylene biphenyl compounds we synthesized the title compound (I), and describe its structure here.

Main group of the title molecule in Fig. 1 has an inversion centre lied on the midpoint of the C—C bond between the inner benzene rings. The C7—C8 bond length of 1.326 (5)Å is comparable with C—C double bond [1.336 (2) Å] reported (Trueblood et al.,1982).

The molecular conformation is stabilized by C—H···O hydrogen bonds. The crystal structure is further stabilized by N—H···O hydrogen bonding interactions (Table 1).

Related literature top

For the optical properties of ethylene biphenyls, see: Song et al. (2003). For comparison bond lengths, see: Trueblood et al. (1982).

Experimental top

A mixture of the Wittig-reagent (0.1 mol), and 2-formylbenzenesulfonic acid (0.2 mol) was stirred in refluxing 4-methylpiperidine (20 mL) for 4 h to afford the title compound (0.084 mol, yield 84%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

2,2'-[(Biphenyl-4,4'-diyl)di(ethene-1,2-diyl)]dibenzenesulfonic acid–4-methylpiperidine–water (1/2/2) top

Crystal data top

C₂₈H₂₂O₆S₂·2(C₆H₁₃N)·2(H₂O)	Z = 2
M_r = 752.96	F(000) = 804
Monoclinic, P2₁/c	D_x = 1.246 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.852 (3) Å	µ = 0.19 mm⁻¹
b = 9.7240 (19) Å	T = 293 K
c = 14.765 (3) Å	Block, yellow
β = 109.76 (3)°	0.26 × 0.21 × 0.18 mm
V = 2006.8 (7) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	1779 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 27.0°, θ_min = 1.5°
ϕ and ω scans	h = −17→17
4436 measured reflections	k = −11→0
4264 independent reflections	l = 0→17

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0935P)² + 0.2207P] where P = (F_o² + 2F_c²)/3
4264 reflections	(Δ/σ)_max < 0.001
243 parameters	Δρ_max = 0.34 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₈H₂₂O₆S₂·2(C₆H₁₃N)·2(H₂O)	V = 2006.8 (7) Å³
M_r = 752.96	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.852 (3) Å	µ = 0.19 mm⁻¹
b = 9.7240 (19) Å	T = 293 K
c = 14.765 (3) Å	0.26 × 0.21 × 0.18 mm
β = 109.76 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1779 reflections with I > 2σ(I)
4436 measured reflections	R_int = 0.026
4264 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	1 restraint
wR(F²) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.34 e Å⁻³
4264 reflections	Δρ_min = −0.27 e Å⁻³
243 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
S1	0.16287 (7)	0.72108 (11)	0.45278 (7)	0.0650 (4)
O1	0.11710 (19)	0.6177 (3)	0.49284 (19)	0.0777 (8)
O2	0.2213 (2)	0.8160 (3)	0.5239 (2)	0.0963 (10)
H2A	0.1872	0.8610	0.5464	0.144*
O3	0.0962 (2)	0.7896 (3)	0.3708 (2)	0.0946 (10)
C1	0.2421 (2)	0.6277 (4)	0.4076 (2)	0.0547 (9)
C2	0.2274 (3)	0.6354 (4)	0.3096 (3)	0.0685 (11)
H2B	0.1789	0.6909	0.2704	0.082*
C3	0.2841 (3)	0.5616 (5)	0.2699 (3)	0.0813 (13)
H3B	0.2744	0.5689	0.2045	0.098*
C4	0.3556 (3)	0.4763 (5)	0.3275 (3)	0.0797 (13)
H4A	0.3918	0.4229	0.3004	0.096*
C5	0.3726 (3)	0.4712 (4)	0.4253 (3)	0.0673 (11)
H5A	0.4222	0.4164	0.4637	0.081*
C6	0.3174 (2)	0.5464 (4)	0.4686 (2)	0.0549 (9)
C7	0.3396 (2)	0.5464 (4)	0.5737 (2)	0.0572 (10)
H7A	0.3073	0.6108	0.5979	0.069*
C8	0.4005 (2)	0.4653 (4)	0.6378 (3)	0.0593 (10)
H8A	0.4296	0.3958	0.6143	0.071*
C9	0.4261 (2)	0.4755 (4)	0.7428 (2)	0.0527 (9)
C10	0.4910 (3)	0.3842 (5)	0.8026 (3)	0.0808 (13)
H10A	0.5164	0.3147	0.7752	0.097*
C11	0.5191 (3)	0.3931 (5)	0.9011 (3)	0.0785 (13)
H11A	0.5627	0.3292	0.9382	0.094*
C12	0.4847 (2)	0.4936 (4)	0.9467 (2)	0.0502 (9)
C13	0.4184 (3)	0.5858 (4)	0.8868 (3)	0.0680 (11)
H13A	0.3927	0.6548	0.9142	0.082*
C14	0.3906 (3)	0.5760 (4)	0.7881 (3)	0.0679 (11)
H14A	0.3466	0.6390	0.7506	0.081*
C17	0.1822 (5)	0.2643 (6)	0.1068 (3)	0.131 (2)
H17A	0.1298	0.2262	0.1227	0.196*
H17B	0.1970	0.3543	0.1346	0.196*
H17C	0.2372	0.2060	0.1317	0.196*
C15	0.0653 (3)	0.3594 (5)	−0.0460 (4)	0.0913 (15)
H15A	0.0749	0.4489	−0.0152	0.110*
H15B	0.0127	0.3150	−0.0327	0.110*
C16	0.0386 (3)	0.3788 (6)	−0.1540 (4)	0.0992 (16)
H16A	0.0216	0.2909	−0.1863	0.119*
H16B	−0.0163	0.4394	−0.1773	0.119*
N2	0.1191 (3)	0.4378 (4)	−0.1755 (2)	0.0859 (11)
H2C	0.1167	0.5144	−0.2053	0.103*
C18	0.2061 (4)	0.3503 (5)	−0.1398 (3)	0.0917 (14)
H18A	0.2582	0.3927	−0.1554	0.110*
H18B	0.1935	0.2609	−0.1706	0.110*
C19	0.2335 (3)	0.3339 (5)	−0.0337 (3)	0.0815 (13)
H19A	0.2516	0.4229	−0.0033	0.098*
H19B	0.2890	0.2741	−0.0111	0.098*
C20	0.1544 (3)	0.2747 (4)	−0.0032 (3)	0.0777 (12)
H20A	0.1410	0.1815	−0.0297	0.093*
O1W	−0.0458 (3)	0.4739 (4)	0.3645 (2)	0.0939 (11)
H2	−0.082 (3)	0.537 (4)	0.380 (3)	0.074 (16)*
H1	0.009 (3)	0.512 (7)	0.410 (4)	0.17 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0645 (6)	0.0621 (6)	0.0658 (6)	0.0026 (6)	0.0188 (5)	0.0124 (6)
O1	0.0773 (18)	0.080 (2)	0.090 (2)	0.0010 (15)	0.0466 (16)	0.0174 (16)
O2	0.101 (2)	0.0657 (19)	0.117 (2)	0.0039 (17)	0.0292 (19)	−0.0220 (18)
O3	0.090 (2)	0.108 (2)	0.0765 (19)	0.0237 (19)	0.0168 (16)	0.0307 (18)
C1	0.048 (2)	0.056 (2)	0.054 (2)	−0.0167 (18)	0.0110 (17)	0.0052 (18)
C2	0.061 (2)	0.084 (3)	0.054 (2)	−0.018 (2)	0.010 (2)	0.009 (2)
C3	0.085 (3)	0.105 (4)	0.055 (3)	−0.030 (3)	0.025 (2)	−0.006 (3)
C4	0.077 (3)	0.096 (3)	0.076 (3)	−0.024 (3)	0.039 (2)	−0.019 (3)
C5	0.055 (2)	0.085 (3)	0.064 (3)	−0.007 (2)	0.022 (2)	−0.001 (2)
C6	0.050 (2)	0.060 (2)	0.058 (2)	−0.0139 (18)	0.0220 (18)	0.0004 (18)
C7	0.056 (2)	0.061 (2)	0.055 (2)	0.0001 (19)	0.0205 (19)	0.0048 (18)
C8	0.053 (2)	0.067 (3)	0.060 (2)	0.0047 (19)	0.0217 (18)	0.003 (2)
C9	0.048 (2)	0.059 (2)	0.053 (2)	0.0041 (18)	0.0196 (17)	0.0057 (19)
C10	0.094 (3)	0.086 (3)	0.063 (3)	0.044 (3)	0.027 (2)	0.006 (2)
C11	0.091 (3)	0.084 (3)	0.057 (3)	0.045 (3)	0.021 (2)	0.012 (2)
C12	0.0452 (19)	0.053 (2)	0.0534 (19)	0.0041 (18)	0.0180 (17)	0.0099 (19)
C13	0.070 (3)	0.070 (3)	0.061 (3)	0.028 (2)	0.017 (2)	0.001 (2)
C14	0.063 (2)	0.073 (3)	0.059 (3)	0.025 (2)	0.009 (2)	0.011 (2)
C17	0.210 (7)	0.108 (4)	0.075 (3)	0.012 (4)	0.051 (4)	0.012 (3)
C15	0.091 (3)	0.081 (3)	0.123 (4)	−0.013 (3)	0.065 (3)	0.010 (3)
C16	0.075 (3)	0.100 (4)	0.100 (4)	−0.001 (3)	0.001 (3)	0.000 (3)
N2	0.106 (3)	0.077 (2)	0.075 (2)	−0.001 (2)	0.032 (2)	0.020 (2)
C18	0.108 (4)	0.088 (3)	0.096 (4)	0.005 (3)	0.057 (3)	−0.003 (3)
C19	0.075 (3)	0.077 (3)	0.086 (3)	0.016 (2)	0.019 (2)	−0.010 (2)
C20	0.114 (4)	0.055 (2)	0.066 (3)	−0.001 (3)	0.033 (2)	0.001 (2)
O1W	0.108 (3)	0.106 (3)	0.068 (2)	0.000 (2)	0.030 (2)	0.0108 (19)

Geometric parameters (Å, º) top

S1—O3	1.442 (3)	C12—C12ⁱ	1.488 (6)
S1—O2	1.446 (3)	C13—C14	1.377 (5)
S1—O1	1.447 (3)	C13—H13A	0.9300
S1—C1	1.784 (4)	C14—H14A	0.9300
O2—H2A	0.8200	C17—C20	1.537 (5)
C1—C2	1.392 (5)	C17—H17A	0.9600
C1—C6	1.417 (5)	C17—H17B	0.9600
C2—C3	1.378 (6)	C17—H17C	0.9600
C2—H2B	0.9300	C15—C20	1.504 (6)
C3—C4	1.389 (6)	C15—C16	1.519 (6)
C3—H3B	0.9300	C15—H15A	0.9700
C4—C5	1.379 (5)	C15—H15B	0.9700
C4—H4A	0.9300	C16—N2	1.455 (6)
C5—C6	1.404 (5)	C16—H16A	0.9700
C5—H5A	0.9300	C16—H16B	0.9700
C6—C7	1.473 (5)	N2—C18	1.487 (5)
C7—C8	1.326 (5)	N2—H2C	0.8600
C7—H7A	0.9300	C18—C19	1.488 (5)
C8—C9	1.469 (5)	C18—H18A	0.9700
C8—H8A	0.9300	C18—H18B	0.9700
C9—C14	1.384 (5)	C19—C20	1.508 (6)
C9—C10	1.387 (5)	C19—H19A	0.9700
C10—C11	1.373 (5)	C19—H19B	0.9700
C10—H10A	0.9300	C20—H20A	0.9800
C11—C12	1.380 (5)	O1W—H2	0.90 (4)
C11—H11A	0.9300	O1W—H1	0.94 (6)
C12—C13	1.402 (5)

O3—S1—O2	112.82 (19)	C12—C13—H13A	119.4
O3—S1—O1	112.34 (19)	C13—C14—C9	122.2 (3)
O2—S1—O1	113.35 (19)	C13—C14—H14A	118.9
O3—S1—C1	105.87 (18)	C9—C14—H14A	118.9
O2—S1—C1	106.64 (17)	C20—C17—H17A	109.5
O1—S1—C1	105.03 (16)	C20—C17—H17B	109.5
S1—O2—H2A	109.5	H17A—C17—H17B	109.5
C2—C1—C6	120.2 (4)	C20—C17—H17C	109.5
C2—C1—S1	118.1 (3)	H17A—C17—H17C	109.5
C6—C1—S1	121.7 (3)	H17B—C17—H17C	109.5
C3—C2—C1	120.8 (4)	C20—C15—C16	113.0 (4)
C3—C2—H2B	119.6	C20—C15—H15A	109.0
C1—C2—H2B	119.6	C16—C15—H15A	109.0
C2—C3—C4	120.0 (4)	C20—C15—H15B	109.0
C2—C3—H3B	120.0	C16—C15—H15B	109.0
C4—C3—H3B	120.0	H15A—C15—H15B	107.8
C5—C4—C3	119.6 (4)	N2—C16—C15	109.6 (4)
C5—C4—H4A	120.2	N2—C16—H16A	109.8
C3—C4—H4A	120.2	C15—C16—H16A	109.8
C4—C5—C6	122.0 (4)	N2—C16—H16B	109.8
C4—C5—H5A	119.0	C15—C16—H16B	109.8
C6—C5—H5A	119.0	H16A—C16—H16B	108.2
C5—C6—C1	117.3 (3)	C16—N2—C18	112.2 (4)
C5—C6—C7	121.5 (3)	C16—N2—H2C	123.9
C1—C6—C7	121.2 (3)	C18—N2—H2C	123.9
C8—C7—C6	127.4 (4)	N2—C18—C19	109.3 (3)
C8—C7—H7A	116.3	N2—C18—H18A	109.8
C6—C7—H7A	116.3	C19—C18—H18A	109.8
C7—C8—C9	125.7 (4)	N2—C18—H18B	109.8
C7—C8—H8A	117.2	C19—C18—H18B	109.8
C9—C8—H8A	117.2	H18A—C18—H18B	108.3
C14—C9—C10	116.1 (3)	C18—C19—C20	113.1 (4)
C14—C9—C8	123.5 (3)	C18—C19—H19A	109.0
C10—C9—C8	120.3 (3)	C20—C19—H19A	109.0
C11—C10—C9	122.0 (4)	C18—C19—H19B	109.0
C11—C10—H10A	119.0	C20—C19—H19B	109.0
C9—C10—H10A	119.0	H19A—C19—H19B	107.8
C10—C11—C12	122.1 (3)	C15—C20—C19	109.2 (3)
C10—C11—H11A	118.9	C15—C20—C17	111.4 (4)
C12—C11—H11A	118.9	C19—C20—C17	112.4 (4)
C11—C12—C13	116.2 (3)	C15—C20—H20A	107.9
C11—C12—C12ⁱ	123.0 (4)	C19—C20—H20A	107.9
C13—C12—C12ⁱ	120.8 (4)	C17—C20—H20A	107.9
C14—C13—C12	121.3 (3)	H2—O1W—H1	90 (3)
C14—C13—H13A	119.4

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1	0.94 (6)	1.95 (6)	2.881 (5)	171 (6)
N2—H2C···O1Wⁱⁱ	0.86	2.23	2.767 (4)	120
N2—H2C···O3ⁱⁱⁱ	0.86	2.28	2.787 (5)	117
C2—H2B···O3	0.93	2.42	2.838 (5)	107
C7—H7A···O2	0.93	2.42	3.103 (5)	130

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂O₆S₂·2(C₆H₁₃N)·2(H₂O)
M_r	752.96
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.852 (3), 9.7240 (19), 14.765 (3)
β (°)	109.76 (3)
V (Å³)	2006.8 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.26 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4436, 4264, 1779
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.204, 1.01
No. of reflections	4264
No. of parameters	243
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.27

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1	0.94 (6)	1.95 (6)	2.881 (5)	171 (6)
N2—H2C···O1Wⁱ	0.8600	2.2300	2.767 (4)	120.00
N2—H2C···O3ⁱⁱ	0.8600	2.2800	2.787 (5)	117.00
C2—H2B···O3	0.9300	2.4200	2.838 (5)	107.00
C7—H7A···O2	0.9300	2.4200	3.103 (5)	130.00

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

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, H. C., Xu, X. H. & Liu, G. R. (2003). Chin. Chem. Res. 14, 1–5. CAS Google Scholar
Trueblood, K., Mirsky, K., Maverick, E., Knobler, C. & Grossenbacher, L. (1982). Acta Cryst. B38, 2428–2435. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o1931

doi:10.1107/S1600536809026932

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′-[(Bi­phenyl-4,4′-di­yl)di(ethene-1,2-di­yl)]di­benzene­sulfonic acid–4-methyl­piperidine–water (1/2/2)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

2,2′-[(Biphenyl-4,4′-diyl)di(ethene-1,2-diyl)]dibenzenesulfonic acid–4-methylpiperidine–water (1/2/2)