PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3017.
Published online 2009 November 7. doi:  10.1107/S1600536809044596
PMCID: PMC2971812

5-(Dimethyl­ammonio)naphthalene-1-sulfonate dihydrate

Abstract

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 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3017-scheme1.jpg

Experimental

Crystal data

  • C12H13NO3S·2H2O
  • M r = 287.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3017-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.108
  • S = 1.12
  • 6004 reflections
  • 377 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2440 Friedel pairs
  • Flack parameter: 0.09 (6)

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H atoms were placed in idealized positions [C—H(methyl)=0.96 Å and C—H(aromatic) =0.93 Å] and included in the refinement in the riding-model approximation, with Uiso(Hmethyl)= 1.5Ueq(C) and Uiso(Haromatic) = 1.2Ueq(C). H atoms bonded to N and O atoms were located from the difference maps with the N-H and O-H distances refined freely and Uiso(H) = 1.2Ueq(N) and 1.2Ueq(O).

Figures

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.

Crystal data

C12H13NO3S·2H2OF(000) = 608
Mr = 287.33Dx = 1.419 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5479 reflections
a = 8.1179 (7) Åθ = 2.5–28.2°
b = 7.7383 (7) ŵ = 0.26 mm1
c = 21.4249 (19) ÅT = 298 K
β = 91.527 (1)°Block, colorless
V = 1345.4 (2) Å30.23 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer6004 independent reflections
Radiation source: fine-focus sealed tube5808 reflections with I > 2σ(I)
graphiteRint = 0.016
[var phi] and ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.943, Tmax = 0.975k = −10→9
10210 measured reflectionsl = −28→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108w = 1/[σ2(Fo2) + (0.057P)2 + 0.1577P] where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
6004 reflectionsΔρmax = 0.30 e Å3
377 parametersΔρmin = −0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 2440 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.09 (6)

Special details

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)

xyzUiso*/Ueq
C1A0.8222 (4)0.7568 (4)0.67513 (13)0.0591 (7)
H1A10.71410.74380.65640.089*
H1A20.81340.77040.71950.089*
H1A30.88680.65610.66660.089*
C2A1.0672 (3)0.9425 (4)0.68158 (12)0.0510 (6)
H2A11.13330.84010.67870.077*
H2A21.04960.96860.72470.077*
H2A31.12301.03740.66250.077*
C3A0.9124 (2)0.8994 (3)0.57984 (9)0.0311 (4)
C4A1.0527 (3)0.8477 (3)0.55268 (11)0.0387 (5)
H4A1.14550.82120.57720.046*
C5A1.0577 (3)0.8341 (3)0.48737 (11)0.0392 (5)
H5A1.15490.80030.46880.047*
C6A0.9221 (2)0.8697 (3)0.45084 (10)0.0342 (4)
H6A0.92770.86000.40770.041*
C7A0.7725 (2)0.9213 (3)0.47795 (9)0.0279 (4)
C8A0.6262 (2)0.9610 (3)0.44142 (9)0.0297 (4)
C9A0.4851 (3)1.0130 (3)0.46934 (10)0.0360 (5)
H9A0.39141.03770.44500.043*
C10A0.4811 (2)1.0293 (3)0.53469 (11)0.0377 (5)
H10A0.38491.06620.55320.045*
C11A0.6160 (3)0.9919 (3)0.57093 (10)0.0353 (4)
H11A0.61071.00240.61410.042*
C12A0.7652 (2)0.9370 (3)0.54411 (9)0.0289 (4)
C1B0.3679 (4)−0.0780 (4)0.17998 (12)0.0604 (8)
H1B10.2618−0.10690.16210.091*
H1B20.3578−0.05610.22380.091*
H1B30.4426−0.17230.17410.091*
C2B0.5991 (3)0.1247 (4)0.17579 (10)0.0431 (5)
H2B10.67330.03030.16900.065*
H2B20.59070.14490.21980.065*
H2B30.64020.22680.15610.065*
C3B0.4261 (2)0.0636 (3)0.07984 (9)0.0306 (4)
C4B0.5612 (3)0.0130 (3)0.04898 (10)0.0356 (4)
H4B0.6583−0.01420.07080.043*
C5B0.5531 (3)0.0021 (3)−0.01663 (11)0.0391 (5)
H5B0.6462−0.0311−0.03800.047*
C6B0.4122 (3)0.0391 (3)−0.04930 (10)0.0339 (4)
H6B0.41060.0335−0.09270.041*
C7B0.2664 (2)0.0865 (3)−0.01780 (9)0.0287 (4)
C8B0.1143 (2)0.1267 (3)−0.04992 (9)0.0324 (4)
C9B−0.0215 (3)0.1749 (3)−0.01754 (11)0.0403 (5)
H9B−0.11950.2002−0.03900.048*
C10B−0.0137 (3)0.1863 (3)0.04774 (12)0.0442 (6)
H10B−0.10670.21970.06910.053*
C11B0.1280 (3)0.1491 (3)0.08027 (10)0.0376 (5)
H11B0.13060.15630.12360.045*
C12B0.2723 (2)0.0993 (3)0.04870 (9)0.0284 (4)
N10.9038 (2)0.9135 (3)0.64846 (8)0.0348 (4)
H10.839 (3)1.018 (4)0.6606 (13)0.042*
N20.4328 (2)0.0813 (2)0.14853 (8)0.0337 (4)
H2A0.376 (3)0.178 (4)0.1585 (12)0.040*
O1A0.4551 (2)0.9795 (3)0.33829 (8)0.0511 (5)
O2A0.6634 (2)0.7583 (2)0.34646 (8)0.0451 (4)
O3A0.7434 (2)1.0568 (3)0.33579 (8)0.0504 (5)
O1B−0.0802 (2)0.1413 (3)−0.14705 (9)0.0578 (5)
O2B0.1916 (3)0.2632 (3)−0.15466 (10)0.0725 (7)
O3B0.1561 (2)−0.0440 (3)−0.15347 (8)0.0560 (5)
O1W0.3130 (3)0.3943 (3)0.18320 (12)0.0594 (6)
H1WA0.366 (5)0.429 (6)0.203 (2)0.089*
H1WB0.240 (5)0.445 (6)0.173 (2)0.089*
O2W0.5713 (3)0.5395 (4)0.24571 (12)0.0736 (8)
H2WA0.589 (6)0.606 (7)0.270 (2)0.110*
H2WB0.624 (6)0.549 (8)0.223 (2)0.110*
O3W0.9865 (3)0.9308 (4)0.25417 (11)0.0628 (6)
H3WA0.920 (5)0.957 (6)0.274 (2)0.094*
H3WB0.951 (5)0.880 (6)0.224 (2)0.094*
O4W0.2032 (3)0.7313 (3)0.32222 (13)0.0709 (7)
H4WA0.279 (5)0.776 (7)0.328 (2)0.106*
H4WB0.140 (6)0.783 (6)0.295 (2)0.106*
S10.62169 (6)0.93747 (7)0.35870 (2)0.03361 (13)
S20.09379 (7)0.11939 (7)−0.13279 (2)0.03875 (14)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C1A0.088 (2)0.0488 (16)0.0404 (13)−0.0201 (15)−0.0035 (13)0.0103 (12)
C2A0.0517 (13)0.0543 (16)0.0459 (13)0.0016 (12)−0.0224 (10)−0.0105 (13)
C3A0.0355 (10)0.0276 (10)0.0298 (9)−0.0024 (7)−0.0062 (7)−0.0011 (7)
C4A0.0331 (10)0.0371 (12)0.0454 (12)0.0024 (9)−0.0077 (9)0.0004 (10)
C5A0.0327 (10)0.0397 (12)0.0454 (12)0.0076 (9)0.0050 (9)−0.0031 (10)
C6A0.0347 (10)0.0359 (11)0.0322 (10)0.0022 (8)0.0026 (8)−0.0044 (8)
C7A0.0302 (8)0.0250 (9)0.0284 (9)−0.0013 (7)−0.0019 (7)−0.0036 (8)
C8A0.0321 (9)0.0281 (11)0.0287 (9)−0.0006 (7)−0.0039 (7)−0.0018 (8)
C9A0.0313 (10)0.0399 (12)0.0364 (11)0.0044 (8)−0.0056 (8)−0.0041 (9)
C10A0.0281 (9)0.0446 (13)0.0406 (11)0.0040 (8)0.0046 (8)−0.0095 (10)
C11A0.0365 (10)0.0408 (12)0.0286 (9)−0.0022 (8)0.0018 (8)−0.0085 (9)
C12A0.0313 (9)0.0256 (9)0.0295 (9)−0.0026 (8)−0.0018 (7)−0.0020 (8)
C1B0.092 (2)0.0495 (16)0.0395 (13)−0.0247 (15)−0.0014 (13)0.0128 (12)
C2B0.0447 (11)0.0458 (13)0.0381 (11)0.0033 (11)−0.0125 (9)−0.0074 (11)
C3B0.0349 (10)0.0286 (10)0.0281 (9)−0.0030 (7)−0.0031 (7)0.0017 (7)
C4B0.0310 (9)0.0380 (12)0.0376 (11)0.0052 (8)−0.0056 (8)0.0001 (9)
C5B0.0333 (10)0.0448 (13)0.0393 (11)0.0032 (9)0.0043 (8)−0.0047 (10)
C6B0.0351 (10)0.0377 (11)0.0288 (10)−0.0002 (8)0.0007 (8)−0.0022 (8)
C7B0.0313 (9)0.0257 (10)0.0291 (9)−0.0014 (7)−0.0020 (7)0.0004 (7)
C8B0.0349 (9)0.0275 (10)0.0344 (9)−0.0016 (8)−0.0053 (7)0.0003 (9)
C9B0.0275 (10)0.0431 (13)0.0497 (13)0.0037 (8)−0.0083 (9)−0.0034 (10)
C10B0.0295 (10)0.0514 (14)0.0520 (14)0.0012 (9)0.0081 (9)−0.0140 (11)
C11B0.0337 (10)0.0445 (13)0.0347 (10)−0.0046 (9)0.0034 (8)−0.0077 (10)
C12B0.0299 (8)0.0255 (10)0.0298 (9)−0.0012 (7)−0.0013 (7)0.0007 (7)
N10.0424 (9)0.0313 (10)0.0302 (8)−0.0014 (7)−0.0079 (7)−0.0011 (7)
N20.0409 (9)0.0335 (10)0.0265 (8)−0.0008 (7)−0.0050 (7)0.0012 (7)
O1A0.0496 (9)0.0619 (12)0.0411 (9)0.0064 (8)−0.0152 (7)−0.0019 (8)
O2A0.0619 (10)0.0390 (9)0.0343 (8)0.0010 (8)−0.0032 (7)−0.0086 (7)
O3A0.0625 (11)0.0479 (11)0.0408 (9)−0.0135 (8)0.0005 (8)0.0049 (8)
O1B0.0517 (10)0.0594 (13)0.0607 (11)0.0024 (9)−0.0275 (8)−0.0005 (10)
O2B0.0861 (15)0.0787 (16)0.0514 (12)−0.0402 (13)−0.0250 (10)0.0286 (11)
O3B0.0684 (12)0.0618 (13)0.0372 (9)0.0117 (10)−0.0103 (8)−0.0072 (9)
O1W0.0548 (12)0.0457 (12)0.0763 (14)0.0097 (8)−0.0231 (10)−0.0161 (10)
O2W0.0552 (12)0.096 (2)0.0693 (16)−0.0101 (12)−0.0061 (10)−0.0406 (14)
O3W0.0552 (11)0.0704 (14)0.0619 (12)0.0060 (11)−0.0140 (9)−0.0246 (12)
O4W0.0612 (13)0.0593 (14)0.0908 (17)−0.0175 (10)−0.0267 (12)0.0331 (12)
S10.0395 (3)0.0342 (3)0.0268 (2)−0.0021 (2)−0.00519 (18)−0.0009 (2)
S20.0428 (3)0.0390 (3)0.0337 (3)−0.0061 (2)−0.0122 (2)0.0076 (2)

Geometric parameters (Å, °)

C1A—N11.502 (3)C3B—C4B1.354 (3)
C1A—H1A10.9600C3B—C12B1.427 (3)
C1A—H1A20.9600C3B—N21.477 (3)
C1A—H1A30.9600C4B—C5B1.408 (3)
C2A—N11.505 (3)C4B—H4B0.9300
C2A—H2A10.9600C5B—C6B1.356 (3)
C2A—H2A20.9600C5B—H5B0.9300
C2A—H2A30.9600C6B—C7B1.426 (3)
C3A—C4A1.353 (3)C6B—H6B0.9300
C3A—C12A1.431 (3)C7B—C12B1.428 (3)
C3A—N11.478 (3)C7B—C8B1.432 (3)
C4A—C5A1.405 (3)C8B—C9B1.369 (3)
C4A—H4A0.9300C8B—S21.780 (2)
C5A—C6A1.362 (3)C9B—C10B1.401 (3)
C5A—H5A0.9300C9B—H9B0.9300
C6A—C7A1.418 (3)C10B—C11B1.360 (3)
C6A—H6A0.9300C10B—H10B0.9300
C7A—C12A1.425 (3)C11B—C12B1.421 (3)
C7A—C8A1.438 (3)C11B—H11B0.9300
C8A—C9A1.367 (3)N1—H11.00 (3)
C8A—S11.781 (2)N2—H2A0.91 (3)
C9A—C10A1.407 (3)O1A—S11.4474 (17)
C9A—H9A0.9300O2A—S11.4525 (18)
C10A—C11A1.357 (3)O3A—S11.4481 (18)
C10A—H10A0.9300O1B—S21.4473 (17)
C11A—C12A1.419 (3)O2B—S21.452 (2)
C11A—H11A0.9300O3B—S21.436 (2)
C1B—N21.507 (3)O1W—H1WA0.65 (5)
C1B—H1B10.9600O1W—H1WB0.74 (4)
C1B—H1B20.9600O2W—H2WA0.74 (5)
C1B—H1B30.9600O2W—H2WB0.65 (4)
C2B—N21.495 (3)O3W—H3WA0.73 (4)
C2B—H2B10.9600O3W—H3WB0.80 (4)
C2B—H2B20.9600O4W—H4WA0.71 (5)
C2B—H2B30.9600O4W—H4WB0.86 (5)
N1—C1A—H1A1109.5C12B—C3B—N2117.15 (17)
N1—C1A—H1A2109.5C3B—C4B—C5B119.20 (19)
H1A1—C1A—H1A2109.5C3B—C4B—H4B120.4
N1—C1A—H1A3109.5C5B—C4B—H4B120.4
H1A1—C1A—H1A3109.5C6B—C5B—C4B121.30 (19)
H1A2—C1A—H1A3109.5C6B—C5B—H5B119.3
N1—C2A—H2A1109.5C4B—C5B—H5B119.3
N1—C2A—H2A2109.5C5B—C6B—C7B120.63 (19)
H2A1—C2A—H2A2109.5C5B—C6B—H6B119.7
N1—C2A—H2A3109.5C7B—C6B—H6B119.7
H2A1—C2A—H2A3109.5C6B—C7B—C12B118.94 (17)
H2A2—C2A—H2A3109.5C6B—C7B—C8B122.98 (18)
C4A—C3A—C12A122.02 (19)C12B—C7B—C8B118.05 (16)
C4A—C3A—N1120.80 (18)C9B—C8B—C7B120.73 (19)
C12A—C3A—N1117.15 (17)C9B—C8B—S2117.31 (16)
C3A—C4A—C5A119.84 (19)C7B—C8B—S2121.95 (15)
C3A—C4A—H4A120.1C8B—C9B—C10B120.50 (19)
C5A—C4A—H4A120.1C8B—C9B—H9B119.8
C6A—C5A—C4A120.8 (2)C10B—C9B—H9B119.8
C6A—C5A—H5A119.6C11B—C10B—C9B120.9 (2)
C4A—C5A—H5A119.6C11B—C10B—H10B119.6
C5A—C6A—C7A120.7 (2)C9B—C10B—H10B119.6
C5A—C6A—H6A119.7C10B—C11B—C12B120.7 (2)
C7A—C6A—H6A119.7C10B—C11B—H11B119.7
C6A—C7A—C12A119.34 (17)C12B—C11B—H11B119.7
C6A—C7A—C8A122.78 (17)C11B—C12B—C3B123.50 (18)
C12A—C7A—C8A117.89 (16)C11B—C12B—C7B119.17 (17)
C9A—C8A—C7A120.95 (18)C3B—C12B—C7B117.32 (17)
C9A—C8A—S1118.06 (15)C3A—N1—C1A110.61 (17)
C7A—C8A—S1120.97 (14)C3A—N1—C2A114.57 (18)
C8A—C9A—C10A120.24 (19)C1A—N1—C2A109.5 (2)
C8A—C9A—H9A119.9C3A—N1—H1110.9 (17)
C10A—C9A—H9A119.9C1A—N1—H1108.1 (16)
C11A—C10A—C9A120.70 (19)C2A—N1—H1102.7 (16)
C11A—C10A—H10A119.6C3B—N2—C2B114.75 (16)
C9A—C10A—H10A119.6C3B—N2—C1B111.46 (17)
C10A—C11A—C12A121.12 (19)C2B—N2—C1B109.40 (19)
C10A—C11A—H11A119.4C3B—N2—H2A107.8 (17)
C12A—C11A—H11A119.4C2B—N2—H2A100.6 (17)
C11A—C12A—C7A119.11 (17)C1B—N2—H2A112.4 (17)
C11A—C12A—C3A123.59 (18)H1WA—O1W—H1WB119 (5)
C7A—C12A—C3A117.29 (17)H2WA—O2W—H2WB109 (6)
N2—C1B—H1B1109.5H3WA—O3W—H3WB111 (4)
N2—C1B—H1B2109.5H4WA—O4W—H4WB112 (5)
H1B1—C1B—H1B2109.5O1A—S1—O3A113.26 (12)
N2—C1B—H1B3109.5O1A—S1—O2A112.35 (11)
H1B1—C1B—H1B3109.5O3A—S1—O2A112.54 (11)
H1B2—C1B—H1B3109.5O1A—S1—C8A105.78 (10)
N2—C2B—H2B1109.5O3A—S1—C8A106.03 (10)
N2—C2B—H2B2109.5O2A—S1—C8A106.16 (10)
H2B1—C2B—H2B2109.5O3B—S2—O1B112.84 (12)
N2—C2B—H2B3109.5O3B—S2—O2B112.01 (14)
H2B1—C2B—H2B3109.5O1B—S2—O2B112.41 (14)
H2B2—C2B—H2B3109.5O3B—S2—C8B108.15 (11)
C4B—C3B—C12B122.54 (18)O1B—S2—C8B105.76 (10)
C4B—C3B—N2120.31 (18)O2B—S2—C8B105.06 (11)
C12A—C3A—C4A—C5A1.7 (3)C7B—C8B—C9B—C10B0.2 (4)
N1—C3A—C4A—C5A179.6 (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—C7A0.0 (4)C9B—C10B—C11B—C12B0.6 (4)
C5A—C6A—C7A—C12A0.5 (3)C10B—C11B—C12B—C3B178.0 (2)
C5A—C6A—C7A—C8A179.8 (2)C10B—C11B—C12B—C7B−0.8 (3)
C6A—C7A—C8A—C9A−178.9 (2)C4B—C3B—C12B—C11B178.6 (2)
C12A—C7A—C8A—C9A0.4 (3)N2—C3B—C12B—C11B−0.4 (3)
C6A—C7A—C8A—S13.0 (3)C4B—C3B—C12B—C7B−2.5 (3)
C12A—C7A—C8A—S1−177.72 (15)N2—C3B—C12B—C7B178.49 (17)
C7A—C8A—C9A—C10A0.3 (3)C6B—C7B—C12B—C11B179.1 (2)
S1—C8A—C9A—C10A178.41 (18)C8B—C7B—C12B—C11B0.7 (3)
C8A—C9A—C10A—C11A−0.8 (4)C6B—C7B—C12B—C3B0.1 (3)
C9A—C10A—C11A—C12A0.6 (4)C8B—C7B—C12B—C3B−178.23 (19)
C10A—C11A—C12A—C7A0.0 (3)C4A—C3A—N1—C1A−99.3 (3)
C10A—C11A—C12A—C3A178.6 (2)C12A—C3A—N1—C1A78.7 (3)
C6A—C7A—C12A—C11A178.8 (2)C4A—C3A—N1—C2A25.0 (3)
C8A—C7A—C12A—C11A−0.5 (3)C12A—C3A—N1—C2A−157.0 (2)
C6A—C7A—C12A—C3A0.2 (3)C4B—C3B—N2—C2B28.3 (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—C11A2.2 (3)C12B—C3B—N2—C1B82.2 (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—O1A177.14 (17)
C12B—C3B—C4B—C5B2.9 (3)C9A—C8A—S1—O3A119.53 (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—O2A57.58 (19)
C5B—C6B—C7B—C12B1.8 (3)C9B—C8B—S2—O3B−130.4 (2)
C5B—C6B—C7B—C8B−179.9 (2)C7B—C8B—S2—O3B50.4 (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—O1B171.49 (18)
C6B—C7B—C8B—S20.4 (3)C9B—C8B—S2—O2B109.8 (2)
C12B—C7B—C8B—S2178.75 (15)C7B—C8B—S2—O2B−69.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O4Wi1.00 (3)1.73 (3)2.689 (3)159 (2)
N2—H2A···O1W0.91 (3)1.83 (3)2.720 (3)165 (2)
O1W—H1WA···O2W0.65 (5)2.07 (5)2.702 (3)165 (5)
O1W—H1WB···O1Bii0.74 (4)2.07 (5)2.784 (3)164 (5)
O2W—H2WA···O2A0.74 (5)2.10 (5)2.828 (3)169 (5)
O2W—H2WB···O3Biii0.65 (4)2.47 (5)3.075 (3)156 (7)
O3W—H3WA···O3A0.73 (4)2.12 (4)2.844 (3)173 (5)
O3W—H3WB···O2Biii0.80 (4)2.07 (4)2.856 (3)167 (4)
O4W—H4WA···O1A0.71 (5)2.14 (5)2.820 (3)162 (6)
O4W—H4WB···O3Wiv0.86 (5)1.89 (5)2.732 (3)165 (5)
C1A—H1A1···O1Av0.962.473.117 (3)125
C1A—H1A2···O1Wi0.962.543.424 (4)154
C2A—H2A1···O3Avi0.962.433.382 (4)170
C2A—H2A3···O2Avii0.962.453.345 (4)156
C6B—H6B···O3B0.932.493.077 (3)122
C1B—H1B1···O1Bviii0.962.463.253 (3)140
C1B—H1B2···O1Aix0.962.573.475 (3)157
C9A—H9A···O1A0.932.402.824 (3)108
C9B—H9B···O1B0.932.392.815 (3)108
C2B—H2B1···O2Bx0.962.363.310 (3)169
C11A—H11A···N10.932.572.894 (3)101
C11B—H11B···N20.932.562.888 (3)101
C2B—H2B3···O3Biii0.962.433.286 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2934).

References

  • Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chimiak, A. & Polonski, T. (1973). Org. Prep. Proc. Int. 5, 117–124.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Mildenstein, V. K. (1971). Acta Histochem. Bd, 40, 29–50. [PubMed]
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography