5-(Dimethyl­ammonio)naphthalene-1-sulfonate dihydrate

Xiao, Z.; Zhan, D.

doi:10.1107/S1600536809044596

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3017

doi:10.1107/S1600536809044596

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5-(Dimethylammonio)naphthalene-1-sulfonate dihydrate

Zuo-an Xiao ^a ^* and Dan Zhan ^a

^aSchool of Chemical Engineering and Food Science, Xiangfan University, Xiangfan 441053, People's Republic of China
^*Correspondence e-mail: blueice8250@yahoo.com.cn

(Received 21 October 2009; accepted 27 October 2009; online 7 November 2009)

There are two formula units in the asymmetric unit of the title compound, C₁₂H₁₃NO₃S·2H₂O. In the crystal structure, molecules are linked by intermolecular O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For potential applications of the title compound, see: Chimiak & Polonski (1973 ).

Experimental

Crystal data

C₁₂H₁₃NO₃S·2H₂O
M_r = 287.33
Monoclinic, P 2₁
a = 8.1179 (7) Å
b = 7.7383 (7) Å
c = 21.4249 (19) Å
β = 91.527 (1)°
V = 1345.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 K
0.23 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.975
10210 measured reflections
6004 independent reflections
5808 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.108
S = 1.12
6004 reflections
377 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 2440 Friedel pairs
Flack parameter: 0.09 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4Wⁱ	1.00 (3)	1.73 (3)	2.689 (3)	159 (2)
N2—H2A⋯O1W	0.91 (3)	1.83 (3)	2.720 (3)	165 (2)
O1W—H1WA⋯O2W	0.65 (5)	2.07 (5)	2.702 (3)	165 (5)
O1W—H1WB⋯O1Bⁱⁱ	0.74 (4)	2.07 (5)	2.784 (3)	164 (5)
O2W—H2WA⋯O2A	0.74 (5)	2.10 (5)	2.828 (3)	169 (5)
O2W—H2WB⋯O3Bⁱⁱⁱ	0.65 (4)	2.47 (5)	3.075 (3)	156 (7)
O3W—H3WA⋯O3A	0.73 (4)	2.12 (4)	2.844 (3)	173 (5)
O3W—H3WB⋯O2Bⁱⁱⁱ	0.80 (4)	2.07 (4)	2.856 (3)	167 (4)
O4W—H4WA⋯O1A	0.71 (5)	2.14 (5)	2.820 (3)	162 (6)
O4W—H4WB⋯O3W^iv	0.86 (5)	1.89 (5)	2.732 (3)	165 (5)
C1A—H1A1⋯O1A^v	0.96	2.47	3.117 (3)	125
C1A—H1A2⋯O1Wⁱ	0.96	2.54	3.424 (4)	154
C2A—H2A1⋯O3A^vi	0.96	2.43	3.382 (4)	170
C2A—H2A3⋯O2A^vii	0.96	2.45	3.345 (4)	156
C6B—H6B⋯O3B	0.93	2.49	3.077 (3)	122
C1B—H1B1⋯O1B^viii	0.96	2.46	3.253 (3)	140
C1B—H1B2⋯O1A^ix	0.96	2.57	3.475 (3)	157
C9A—H9A⋯O1A	0.93	2.40	2.824 (3)	108
C9B—H9B⋯O1B	0.93	2.39	2.815 (3)	108
C2B—H2B1⋯O2B^x	0.96	2.36	3.310 (3)	169
C2B—H2B3⋯O3Bⁱⁱⁱ	0.96	2.43	3.286 (3)	149
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iv) x-1, y, z; (v) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (vi) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (vii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (viii) $[-x, y-{\script{1\over 2}}, -z]$ ; (ix) x, y-1, z; (x) $[-x+1, y-{\script{1\over 2}}, -z]$ .

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, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044596/lh2934sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809044596/lh2934Isup2.hkl

checkCIF report

Comment top

Dansyl acid (5-(dimethylamino)-1-naphthalenesulfonic acid) is an inermidiate that can be used in the preparation of dansyl chloride (Chimiak & Polonski, 1973; Mildenstein, 1971) and is used as a dye due to its good fluorescent property and water solublity. In order to obtain the pure standard sample, the title compound, (I), was crystallized from the technical grade dansyl acid, and we report the crystal stucture herein.

In the molecular structure (Fig. 1), the N atom of the dimethylamino group is protonated. There are two crystallographically independent molecules in the asymmetric unit. All bond lengths and bond angles are as expected. In the crystal structure (Fig.2), the molecules are linked by intermolecular O—H···O, N—H···O and weak C-H···O hydrogen bonds to form a three-dimensional network.

Related literature top

For potential applications of the title compound, see: Chimiak & Polonski (1973).

Experimental top

The title compound was crystallized from technical grade dansyl acid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in water at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (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, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), with displacement ellipsoids drawn at the 50% probability level and hydrogen bonds shown as dashed lines.
	Fig. 2. Part of the crystal structure of (I) showing hydrogen bonds as dashed lines.

5-(Dimethylammonio)naphthalene-1-sulfonate dihydrate top

Crystal data top

C₁₂H₁₃NO₃S·2H₂O	F(000) = 608
M_r = 287.33	D_x = 1.419 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5479 reflections
a = 8.1179 (7) Å	θ = 2.5–28.2°
b = 7.7383 (7) Å	µ = 0.26 mm⁻¹
c = 21.4249 (19) Å	T = 298 K
β = 91.527 (1)°	Block, colorless
V = 1345.4 (2) Å³	0.23 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	6004 independent reflections
Radiation source: fine-focus sealed tube	5808 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.943, T_max = 0.975	k = −10→9
10210 measured reflections	l = −28→22

Refinement top

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.057P)² + 0.1577P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
6004 reflections	Δρ_max = 0.30 e Å⁻³
377 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2440 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (6)

Crystal data top

C₁₂H₁₃NO₃S·2H₂O	V = 1345.4 (2) Å³
M_r = 287.33	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 8.1179 (7) Å	µ = 0.26 mm⁻¹
b = 7.7383 (7) Å	T = 298 K
c = 21.4249 (19) Å	0.23 × 0.10 × 0.10 mm
β = 91.527 (1)°

Data collection top

Bruker SMART CCD diffractometer	6004 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5808 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.975	R_int = 0.016
10210 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	Δρ_max = 0.30 e Å⁻³
S = 1.12	Δρ_min = −0.25 e Å⁻³
6004 reflections	Absolute structure: Flack (1983), 2440 Friedel pairs
377 parameters	Absolute structure parameter: 0.09 (6)
1 restraint

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
C1A	0.8222 (4)	0.7568 (4)	0.67513 (13)	0.0591 (7)
H1A1	0.7141	0.7438	0.6564	0.089*
H1A2	0.8134	0.7704	0.7195	0.089*
H1A3	0.8868	0.6561	0.6666	0.089*
C2A	1.0672 (3)	0.9425 (4)	0.68158 (12)	0.0510 (6)
H2A1	1.1333	0.8401	0.6787	0.077*
H2A2	1.0496	0.9686	0.7247	0.077*
H2A3	1.1230	1.0374	0.6625	0.077*
C3A	0.9124 (2)	0.8994 (3)	0.57984 (9)	0.0311 (4)
C4A	1.0527 (3)	0.8477 (3)	0.55268 (11)	0.0387 (5)
H4A	1.1455	0.8212	0.5772	0.046*
C5A	1.0577 (3)	0.8341 (3)	0.48737 (11)	0.0392 (5)
H5A	1.1549	0.8003	0.4688	0.047*
C6A	0.9221 (2)	0.8697 (3)	0.45084 (10)	0.0342 (4)
H6A	0.9277	0.8600	0.4077	0.041*
C7A	0.7725 (2)	0.9213 (3)	0.47795 (9)	0.0279 (4)
C8A	0.6262 (2)	0.9610 (3)	0.44142 (9)	0.0297 (4)
C9A	0.4851 (3)	1.0130 (3)	0.46934 (10)	0.0360 (5)
H9A	0.3914	1.0377	0.4450	0.043*
C10A	0.4811 (2)	1.0293 (3)	0.53469 (11)	0.0377 (5)
H10A	0.3849	1.0662	0.5532	0.045*
C11A	0.6160 (3)	0.9919 (3)	0.57093 (10)	0.0353 (4)
H11A	0.6107	1.0024	0.6141	0.042*
C12A	0.7652 (2)	0.9370 (3)	0.54411 (9)	0.0289 (4)
C1B	0.3679 (4)	−0.0780 (4)	0.17998 (12)	0.0604 (8)
H1B1	0.2618	−0.1069	0.1621	0.091*
H1B2	0.3578	−0.0561	0.2238	0.091*
H1B3	0.4426	−0.1723	0.1741	0.091*
C2B	0.5991 (3)	0.1247 (4)	0.17579 (10)	0.0431 (5)
H2B1	0.6733	0.0303	0.1690	0.065*
H2B2	0.5907	0.1449	0.2198	0.065*
H2B3	0.6402	0.2268	0.1561	0.065*
C3B	0.4261 (2)	0.0636 (3)	0.07984 (9)	0.0306 (4)
C4B	0.5612 (3)	0.0130 (3)	0.04898 (10)	0.0356 (4)
H4B	0.6583	−0.0142	0.0708	0.043*
C5B	0.5531 (3)	0.0021 (3)	−0.01663 (11)	0.0391 (5)
H5B	0.6462	−0.0311	−0.0380	0.047*
C6B	0.4122 (3)	0.0391 (3)	−0.04930 (10)	0.0339 (4)
H6B	0.4106	0.0335	−0.0927	0.041*
C7B	0.2664 (2)	0.0865 (3)	−0.01780 (9)	0.0287 (4)
C8B	0.1143 (2)	0.1267 (3)	−0.04992 (9)	0.0324 (4)
C9B	−0.0215 (3)	0.1749 (3)	−0.01754 (11)	0.0403 (5)
H9B	−0.1195	0.2002	−0.0390	0.048*
C10B	−0.0137 (3)	0.1863 (3)	0.04774 (12)	0.0442 (6)
H10B	−0.1067	0.2197	0.0691	0.053*
C11B	0.1280 (3)	0.1491 (3)	0.08027 (10)	0.0376 (5)
H11B	0.1306	0.1563	0.1236	0.045*
C12B	0.2723 (2)	0.0993 (3)	0.04870 (9)	0.0284 (4)
N1	0.9038 (2)	0.9135 (3)	0.64846 (8)	0.0348 (4)
H1	0.839 (3)	1.018 (4)	0.6606 (13)	0.042*
N2	0.4328 (2)	0.0813 (2)	0.14853 (8)	0.0337 (4)
H2A	0.376 (3)	0.178 (4)	0.1585 (12)	0.040*
O1A	0.4551 (2)	0.9795 (3)	0.33829 (8)	0.0511 (5)
O2A	0.6634 (2)	0.7583 (2)	0.34646 (8)	0.0451 (4)
O3A	0.7434 (2)	1.0568 (3)	0.33579 (8)	0.0504 (5)
O1B	−0.0802 (2)	0.1413 (3)	−0.14705 (9)	0.0578 (5)
O2B	0.1916 (3)	0.2632 (3)	−0.15466 (10)	0.0725 (7)
O3B	0.1561 (2)	−0.0440 (3)	−0.15347 (8)	0.0560 (5)
O1W	0.3130 (3)	0.3943 (3)	0.18320 (12)	0.0594 (6)
H1WA	0.366 (5)	0.429 (6)	0.203 (2)	0.089*
H1WB	0.240 (5)	0.445 (6)	0.173 (2)	0.089*
O2W	0.5713 (3)	0.5395 (4)	0.24571 (12)	0.0736 (8)
H2WA	0.589 (6)	0.606 (7)	0.270 (2)	0.110*
H2WB	0.624 (6)	0.549 (8)	0.223 (2)	0.110*
O3W	0.9865 (3)	0.9308 (4)	0.25417 (11)	0.0628 (6)
H3WA	0.920 (5)	0.957 (6)	0.274 (2)	0.094*
H3WB	0.951 (5)	0.880 (6)	0.224 (2)	0.094*
O4W	0.2032 (3)	0.7313 (3)	0.32222 (13)	0.0709 (7)
H4WA	0.279 (5)	0.776 (7)	0.328 (2)	0.106*
H4WB	0.140 (6)	0.783 (6)	0.295 (2)	0.106*
S1	0.62169 (6)	0.93747 (7)	0.35870 (2)	0.03361 (13)
S2	0.09379 (7)	0.11939 (7)	−0.13279 (2)	0.03875 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.088 (2)	0.0488 (16)	0.0404 (13)	−0.0201 (15)	−0.0035 (13)	0.0103 (12)
C2A	0.0517 (13)	0.0543 (16)	0.0459 (13)	0.0016 (12)	−0.0224 (10)	−0.0105 (13)
C3A	0.0355 (10)	0.0276 (10)	0.0298 (9)	−0.0024 (7)	−0.0062 (7)	−0.0011 (7)
C4A	0.0331 (10)	0.0371 (12)	0.0454 (12)	0.0024 (9)	−0.0077 (9)	0.0004 (10)
C5A	0.0327 (10)	0.0397 (12)	0.0454 (12)	0.0076 (9)	0.0050 (9)	−0.0031 (10)
C6A	0.0347 (10)	0.0359 (11)	0.0322 (10)	0.0022 (8)	0.0026 (8)	−0.0044 (8)
C7A	0.0302 (8)	0.0250 (9)	0.0284 (9)	−0.0013 (7)	−0.0019 (7)	−0.0036 (8)
C8A	0.0321 (9)	0.0281 (11)	0.0287 (9)	−0.0006 (7)	−0.0039 (7)	−0.0018 (8)
C9A	0.0313 (10)	0.0399 (12)	0.0364 (11)	0.0044 (8)	−0.0056 (8)	−0.0041 (9)
C10A	0.0281 (9)	0.0446 (13)	0.0406 (11)	0.0040 (8)	0.0046 (8)	−0.0095 (10)
C11A	0.0365 (10)	0.0408 (12)	0.0286 (9)	−0.0022 (8)	0.0018 (8)	−0.0085 (9)
C12A	0.0313 (9)	0.0256 (9)	0.0295 (9)	−0.0026 (8)	−0.0018 (7)	−0.0020 (8)
C1B	0.092 (2)	0.0495 (16)	0.0395 (13)	−0.0247 (15)	−0.0014 (13)	0.0128 (12)
C2B	0.0447 (11)	0.0458 (13)	0.0381 (11)	0.0033 (11)	−0.0125 (9)	−0.0074 (11)
C3B	0.0349 (10)	0.0286 (10)	0.0281 (9)	−0.0030 (7)	−0.0031 (7)	0.0017 (7)
C4B	0.0310 (9)	0.0380 (12)	0.0376 (11)	0.0052 (8)	−0.0056 (8)	0.0001 (9)
C5B	0.0333 (10)	0.0448 (13)	0.0393 (11)	0.0032 (9)	0.0043 (8)	−0.0047 (10)
C6B	0.0351 (10)	0.0377 (11)	0.0288 (10)	−0.0002 (8)	0.0007 (8)	−0.0022 (8)
C7B	0.0313 (9)	0.0257 (10)	0.0291 (9)	−0.0014 (7)	−0.0020 (7)	0.0004 (7)
C8B	0.0349 (9)	0.0275 (10)	0.0344 (9)	−0.0016 (8)	−0.0053 (7)	0.0003 (9)
C9B	0.0275 (10)	0.0431 (13)	0.0497 (13)	0.0037 (8)	−0.0083 (9)	−0.0034 (10)
C10B	0.0295 (10)	0.0514 (14)	0.0520 (14)	0.0012 (9)	0.0081 (9)	−0.0140 (11)
C11B	0.0337 (10)	0.0445 (13)	0.0347 (10)	−0.0046 (9)	0.0034 (8)	−0.0077 (10)
C12B	0.0299 (8)	0.0255 (10)	0.0298 (9)	−0.0012 (7)	−0.0013 (7)	0.0007 (7)
N1	0.0424 (9)	0.0313 (10)	0.0302 (8)	−0.0014 (7)	−0.0079 (7)	−0.0011 (7)
N2	0.0409 (9)	0.0335 (10)	0.0265 (8)	−0.0008 (7)	−0.0050 (7)	0.0012 (7)
O1A	0.0496 (9)	0.0619 (12)	0.0411 (9)	0.0064 (8)	−0.0152 (7)	−0.0019 (8)
O2A	0.0619 (10)	0.0390 (9)	0.0343 (8)	0.0010 (8)	−0.0032 (7)	−0.0086 (7)
O3A	0.0625 (11)	0.0479 (11)	0.0408 (9)	−0.0135 (8)	0.0005 (8)	0.0049 (8)
O1B	0.0517 (10)	0.0594 (13)	0.0607 (11)	0.0024 (9)	−0.0275 (8)	−0.0005 (10)
O2B	0.0861 (15)	0.0787 (16)	0.0514 (12)	−0.0402 (13)	−0.0250 (10)	0.0286 (11)
O3B	0.0684 (12)	0.0618 (13)	0.0372 (9)	0.0117 (10)	−0.0103 (8)	−0.0072 (9)
O1W	0.0548 (12)	0.0457 (12)	0.0763 (14)	0.0097 (8)	−0.0231 (10)	−0.0161 (10)
O2W	0.0552 (12)	0.096 (2)	0.0693 (16)	−0.0101 (12)	−0.0061 (10)	−0.0406 (14)
O3W	0.0552 (11)	0.0704 (14)	0.0619 (12)	0.0060 (11)	−0.0140 (9)	−0.0246 (12)
O4W	0.0612 (13)	0.0593 (14)	0.0908 (17)	−0.0175 (10)	−0.0267 (12)	0.0331 (12)
S1	0.0395 (3)	0.0342 (3)	0.0268 (2)	−0.0021 (2)	−0.00519 (18)	−0.0009 (2)
S2	0.0428 (3)	0.0390 (3)	0.0337 (3)	−0.0061 (2)	−0.0122 (2)	0.0076 (2)

Geometric parameters (Å, º) top

C1A—N1	1.502 (3)	C3B—C4B	1.354 (3)
C1A—H1A1	0.9600	C3B—C12B	1.427 (3)
C1A—H1A2	0.9600	C3B—N2	1.477 (3)
C1A—H1A3	0.9600	C4B—C5B	1.408 (3)
C2A—N1	1.505 (3)	C4B—H4B	0.9300
C2A—H2A1	0.9600	C5B—C6B	1.356 (3)
C2A—H2A2	0.9600	C5B—H5B	0.9300
C2A—H2A3	0.9600	C6B—C7B	1.426 (3)
C3A—C4A	1.353 (3)	C6B—H6B	0.9300
C3A—C12A	1.431 (3)	C7B—C12B	1.428 (3)
C3A—N1	1.478 (3)	C7B—C8B	1.432 (3)
C4A—C5A	1.405 (3)	C8B—C9B	1.369 (3)
C4A—H4A	0.9300	C8B—S2	1.780 (2)
C5A—C6A	1.362 (3)	C9B—C10B	1.401 (3)
C5A—H5A	0.9300	C9B—H9B	0.9300
C6A—C7A	1.418 (3)	C10B—C11B	1.360 (3)
C6A—H6A	0.9300	C10B—H10B	0.9300
C7A—C12A	1.425 (3)	C11B—C12B	1.421 (3)
C7A—C8A	1.438 (3)	C11B—H11B	0.9300
C8A—C9A	1.367 (3)	N1—H1	1.00 (3)
C8A—S1	1.781 (2)	N2—H2A	0.91 (3)
C9A—C10A	1.407 (3)	O1A—S1	1.4474 (17)
C9A—H9A	0.9300	O2A—S1	1.4525 (18)
C10A—C11A	1.357 (3)	O3A—S1	1.4481 (18)
C10A—H10A	0.9300	O1B—S2	1.4473 (17)
C11A—C12A	1.419 (3)	O2B—S2	1.452 (2)
C11A—H11A	0.9300	O3B—S2	1.436 (2)
C1B—N2	1.507 (3)	O1W—H1WA	0.65 (5)
C1B—H1B1	0.9600	O1W—H1WB	0.74 (4)
C1B—H1B2	0.9600	O2W—H2WA	0.74 (5)
C1B—H1B3	0.9600	O2W—H2WB	0.65 (4)
C2B—N2	1.495 (3)	O3W—H3WA	0.73 (4)
C2B—H2B1	0.9600	O3W—H3WB	0.80 (4)
C2B—H2B2	0.9600	O4W—H4WA	0.71 (5)
C2B—H2B3	0.9600	O4W—H4WB	0.86 (5)

N1—C1A—H1A1	109.5	C12B—C3B—N2	117.15 (17)
N1—C1A—H1A2	109.5	C3B—C4B—C5B	119.20 (19)
H1A1—C1A—H1A2	109.5	C3B—C4B—H4B	120.4
N1—C1A—H1A3	109.5	C5B—C4B—H4B	120.4
H1A1—C1A—H1A3	109.5	C6B—C5B—C4B	121.30 (19)
H1A2—C1A—H1A3	109.5	C6B—C5B—H5B	119.3
N1—C2A—H2A1	109.5	C4B—C5B—H5B	119.3
N1—C2A—H2A2	109.5	C5B—C6B—C7B	120.63 (19)
H2A1—C2A—H2A2	109.5	C5B—C6B—H6B	119.7
N1—C2A—H2A3	109.5	C7B—C6B—H6B	119.7
H2A1—C2A—H2A3	109.5	C6B—C7B—C12B	118.94 (17)
H2A2—C2A—H2A3	109.5	C6B—C7B—C8B	122.98 (18)
C4A—C3A—C12A	122.02 (19)	C12B—C7B—C8B	118.05 (16)
C4A—C3A—N1	120.80 (18)	C9B—C8B—C7B	120.73 (19)
C12A—C3A—N1	117.15 (17)	C9B—C8B—S2	117.31 (16)
C3A—C4A—C5A	119.84 (19)	C7B—C8B—S2	121.95 (15)
C3A—C4A—H4A	120.1	C8B—C9B—C10B	120.50 (19)
C5A—C4A—H4A	120.1	C8B—C9B—H9B	119.8
C6A—C5A—C4A	120.8 (2)	C10B—C9B—H9B	119.8
C6A—C5A—H5A	119.6	C11B—C10B—C9B	120.9 (2)
C4A—C5A—H5A	119.6	C11B—C10B—H10B	119.6
C5A—C6A—C7A	120.7 (2)	C9B—C10B—H10B	119.6
C5A—C6A—H6A	119.7	C10B—C11B—C12B	120.7 (2)
C7A—C6A—H6A	119.7	C10B—C11B—H11B	119.7
C6A—C7A—C12A	119.34 (17)	C12B—C11B—H11B	119.7
C6A—C7A—C8A	122.78 (17)	C11B—C12B—C3B	123.50 (18)
C12A—C7A—C8A	117.89 (16)	C11B—C12B—C7B	119.17 (17)
C9A—C8A—C7A	120.95 (18)	C3B—C12B—C7B	117.32 (17)
C9A—C8A—S1	118.06 (15)	C3A—N1—C1A	110.61 (17)
C7A—C8A—S1	120.97 (14)	C3A—N1—C2A	114.57 (18)
C8A—C9A—C10A	120.24 (19)	C1A—N1—C2A	109.5 (2)
C8A—C9A—H9A	119.9	C3A—N1—H1	110.9 (17)
C10A—C9A—H9A	119.9	C1A—N1—H1	108.1 (16)
C11A—C10A—C9A	120.70 (19)	C2A—N1—H1	102.7 (16)
C11A—C10A—H10A	119.6	C3B—N2—C2B	114.75 (16)
C9A—C10A—H10A	119.6	C3B—N2—C1B	111.46 (17)
C10A—C11A—C12A	121.12 (19)	C2B—N2—C1B	109.40 (19)
C10A—C11A—H11A	119.4	C3B—N2—H2A	107.8 (17)
C12A—C11A—H11A	119.4	C2B—N2—H2A	100.6 (17)
C11A—C12A—C7A	119.11 (17)	C1B—N2—H2A	112.4 (17)
C11A—C12A—C3A	123.59 (18)	H1WA—O1W—H1WB	119 (5)
C7A—C12A—C3A	117.29 (17)	H2WA—O2W—H2WB	109 (6)
N2—C1B—H1B1	109.5	H3WA—O3W—H3WB	111 (4)
N2—C1B—H1B2	109.5	H4WA—O4W—H4WB	112 (5)
H1B1—C1B—H1B2	109.5	O1A—S1—O3A	113.26 (12)
N2—C1B—H1B3	109.5	O1A—S1—O2A	112.35 (11)
H1B1—C1B—H1B3	109.5	O3A—S1—O2A	112.54 (11)
H1B2—C1B—H1B3	109.5	O1A—S1—C8A	105.78 (10)
N2—C2B—H2B1	109.5	O3A—S1—C8A	106.03 (10)
N2—C2B—H2B2	109.5	O2A—S1—C8A	106.16 (10)
H2B1—C2B—H2B2	109.5	O3B—S2—O1B	112.84 (12)
N2—C2B—H2B3	109.5	O3B—S2—O2B	112.01 (14)
H2B1—C2B—H2B3	109.5	O1B—S2—O2B	112.41 (14)
H2B2—C2B—H2B3	109.5	O3B—S2—C8B	108.15 (11)
C4B—C3B—C12B	122.54 (18)	O1B—S2—C8B	105.76 (10)
C4B—C3B—N2	120.31 (18)	O2B—S2—C8B	105.06 (11)

C12A—C3A—C4A—C5A	1.7 (3)	C7B—C8B—C9B—C10B	0.2 (4)
N1—C3A—C4A—C5A	179.6 (2)	S2—C8B—C9B—C10B	−178.97 (19)
C3A—C4A—C5A—C6A	−1.0 (4)	C8B—C9B—C10B—C11B	−0.3 (4)
C4A—C5A—C6A—C7A	0.0 (4)	C9B—C10B—C11B—C12B	0.6 (4)
C5A—C6A—C7A—C12A	0.5 (3)	C10B—C11B—C12B—C3B	178.0 (2)
C5A—C6A—C7A—C8A	179.8 (2)	C10B—C11B—C12B—C7B	−0.8 (3)
C6A—C7A—C8A—C9A	−178.9 (2)	C4B—C3B—C12B—C11B	178.6 (2)
C12A—C7A—C8A—C9A	0.4 (3)	N2—C3B—C12B—C11B	−0.4 (3)
C6A—C7A—C8A—S1	3.0 (3)	C4B—C3B—C12B—C7B	−2.5 (3)
C12A—C7A—C8A—S1	−177.72 (15)	N2—C3B—C12B—C7B	178.49 (17)
C7A—C8A—C9A—C10A	0.3 (3)	C6B—C7B—C12B—C11B	179.1 (2)
S1—C8A—C9A—C10A	178.41 (18)	C8B—C7B—C12B—C11B	0.7 (3)
C8A—C9A—C10A—C11A	−0.8 (4)	C6B—C7B—C12B—C3B	0.1 (3)
C9A—C10A—C11A—C12A	0.6 (4)	C8B—C7B—C12B—C3B	−178.23 (19)
C10A—C11A—C12A—C7A	0.0 (3)	C4A—C3A—N1—C1A	−99.3 (3)
C10A—C11A—C12A—C3A	178.6 (2)	C12A—C3A—N1—C1A	78.7 (3)
C6A—C7A—C12A—C11A	178.8 (2)	C4A—C3A—N1—C2A	25.0 (3)
C8A—C7A—C12A—C11A	−0.5 (3)	C12A—C3A—N1—C2A	−157.0 (2)
C6A—C7A—C12A—C3A	0.2 (3)	C4B—C3B—N2—C2B	28.3 (3)
C8A—C7A—C12A—C3A	−179.17 (19)	C12B—C3B—N2—C2B	−152.7 (2)
C4A—C3A—C12A—C11A	−179.8 (2)	C4B—C3B—N2—C1B	−96.8 (3)
N1—C3A—C12A—C11A	2.2 (3)	C12B—C3B—N2—C1B	82.2 (3)
C4A—C3A—C12A—C7A	−1.2 (3)	C9A—C8A—S1—O1A	−1.0 (2)
N1—C3A—C12A—C7A	−179.19 (18)	C7A—C8A—S1—O1A	177.14 (17)
C12B—C3B—C4B—C5B	2.9 (3)	C9A—C8A—S1—O3A	119.53 (19)
N2—C3B—C4B—C5B	−178.1 (2)	C7A—C8A—S1—O3A	−62.32 (19)
C3B—C4B—C5B—C6B	−0.9 (4)	C9A—C8A—S1—O2A	−120.57 (18)
C4B—C5B—C6B—C7B	−1.5 (4)	C7A—C8A—S1—O2A	57.58 (19)
C5B—C6B—C7B—C12B	1.8 (3)	C9B—C8B—S2—O3B	−130.4 (2)
C5B—C6B—C7B—C8B	−179.9 (2)	C7B—C8B—S2—O3B	50.4 (2)
C6B—C7B—C8B—C9B	−178.7 (2)	C9B—C8B—S2—O1B	−9.3 (2)
C12B—C7B—C8B—C9B	−0.4 (3)	C7B—C8B—S2—O1B	171.49 (18)
C6B—C7B—C8B—S2	0.4 (3)	C9B—C8B—S2—O2B	109.8 (2)
C12B—C7B—C8B—S2	178.75 (15)	C7B—C8B—S2—O2B	−69.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4Wⁱ	1.00 (3)	1.73 (3)	2.689 (3)	159 (2)
N2—H2A···O1W	0.91 (3)	1.83 (3)	2.720 (3)	165 (2)
O1W—H1WA···O2W	0.65 (5)	2.07 (5)	2.702 (3)	165 (5)
O1W—H1WB···O1Bⁱⁱ	0.74 (4)	2.07 (5)	2.784 (3)	164 (5)
O2W—H2WA···O2A	0.74 (5)	2.10 (5)	2.828 (3)	169 (5)
O2W—H2WB···O3Bⁱⁱⁱ	0.65 (4)	2.47 (5)	3.075 (3)	156 (7)
O3W—H3WA···O3A	0.73 (4)	2.12 (4)	2.844 (3)	173 (5)
O3W—H3WB···O2Bⁱⁱⁱ	0.80 (4)	2.07 (4)	2.856 (3)	167 (4)
O4W—H4WA···O1A	0.71 (5)	2.14 (5)	2.820 (3)	162 (6)
O4W—H4WB···O3W^iv	0.86 (5)	1.89 (5)	2.732 (3)	165 (5)
C1A—H1A1···O1A^v	0.96	2.47	3.117 (3)	125
C1A—H1A2···O1Wⁱ	0.96	2.54	3.424 (4)	154
C2A—H2A1···O3A^vi	0.96	2.43	3.382 (4)	170
C2A—H2A3···O2A^vii	0.96	2.45	3.345 (4)	156
C6B—H6B···O3B	0.93	2.49	3.077 (3)	122
C1B—H1B1···O1B^viii	0.96	2.46	3.253 (3)	140
C1B—H1B2···O1A^ix	0.96	2.57	3.475 (3)	157
C9A—H9A···O1A	0.93	2.40	2.824 (3)	108
C9B—H9B···O1B	0.93	2.39	2.815 (3)	108
C2B—H2B1···O2B^x	0.96	2.36	3.310 (3)	169
C11A—H11A···N1	0.93	2.57	2.894 (3)	101
C11B—H11B···N2	0.93	2.56	2.888 (3)	101
C2B—H2B3···O3Bⁱⁱⁱ	0.96	2.43	3.286 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃NO₃S·2H₂O
M_r	287.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	8.1179 (7), 7.7383 (7), 21.4249 (19)
β (°)	91.527 (1)
V (Å³)	1345.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.23 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	10210, 6004, 5808
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.108, 1.12
No. of reflections	6004
No. of parameters	377
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)	0.30, −0.25
Absolute structure	Flack (1983), 2440 Friedel pairs
Absolute structure parameter	0.09 (6)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4Wⁱ	1.00 (3)	1.73 (3)	2.689 (3)	159 (2)
N2—H2A···O1W	0.91 (3)	1.83 (3)	2.720 (3)	165 (2)
O1W—H1WA···O2W	0.65 (5)	2.07 (5)	2.702 (3)	165 (5)
O1W—H1WB···O1Bⁱⁱ	0.74 (4)	2.07 (5)	2.784 (3)	164 (5)
O2W—H2WA···O2A	0.74 (5)	2.10 (5)	2.828 (3)	169 (5)
O2W—H2WB···O3Bⁱⁱⁱ	0.65 (4)	2.47 (5)	3.075 (3)	156 (7)
O3W—H3WA···O3A	0.73 (4)	2.12 (4)	2.844 (3)	173 (5)
O3W—H3WB···O2Bⁱⁱⁱ	0.80 (4)	2.07 (4)	2.856 (3)	167 (4)
O4W—H4WA···O1A	0.71 (5)	2.14 (5)	2.820 (3)	162 (6)
O4W—H4WB···O3W^iv	0.86 (5)	1.89 (5)	2.732 (3)	165 (5)
C1A—H1A1···O1A^v	0.96	2.47	3.117 (3)	124.8
C1A—H1A2···O1Wⁱ	0.96	2.54	3.424 (4)	153.8
C2A—H2A1···O3A^vi	0.96	2.43	3.382 (4)	169.9
C2A—H2A3···O2A^vii	0.96	2.45	3.345 (4)	155.7
C6B—H6B···O3B	0.93	2.49	3.077 (3)	121.6
C1B—H1B1···O1B^viii	0.96	2.46	3.253 (3)	140.0
C1B—H1B2···O1A^ix	0.96	2.57	3.475 (3)	157.0
C9A—H9A···O1A	0.93	2.40	2.824 (3)	107.5
C9B—H9B···O1B	0.93	2.39	2.815 (3)	107.8
C2B—H2B1···O2B^x	0.96	2.36	3.310 (3)	168.5
C11A—H11A···N1	0.93	2.57	2.894 (3)	101.2
C11B—H11B···N2	0.93	2.56	2.888 (3)	100.9
C2B—H2B3···O3Bⁱⁱⁱ	0.96	2.43	3.286 (3)	148.9

Acknowledgements

The authors are grateful to the Science Technology Research Programme of the Education Office of Hubei Province (grant No. Q20092503) for financial support.

References

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