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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-Fluoro-N-methyl-N-(1,2,3,4-tetra­hydro­carbazol-3-yl)benzene­sulfonamide

aUniversity of Southern Denmark, Department of Physics and Chemistry, Campusvej 55, 5230 Odense M, Denmark
*Correspondence e-mail: adb@chem.sdu.dk

(Received 3 March 2009; accepted 7 March 2009; online 11 March 2009)

In the title compound, C19H19FN2O2S, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the plane of the fluoro­phenyl ring forms a dihedral angle of 41.5 (1)° with respect to the carbazole mean plane. The crystal structure is segregated into layers containing the carbazole units and fluoro­phenyl rings in alternate (200) planes. The carbazole units form centrosymmetric face-to-face inter­actions [inter­planar separation = 4.06 (1) Å] and edge-to-face inter­actions in which the N—H group is directed towards an adjacent carbazole face, with a shortest H⋯C contact of 2.53 Å. The fluoro­phenyl rings form face-to-face contacts with an approximate inter­planar separation of 3.75 Å and a centroid–centroid distance of 4.73 (1) Å.

Related literature

For background literature and synthesis details, see: Ulven & Kostenis (2005[Ulven, T. & Kostenis, E. (2005). J. Med. Chem. 48, 897-900.], 2006[Ulven, T. & Kostenis, E. (2006). Curr. Top. Med. Chem. 6, 1427-1444.]). For related structures, see: Bjerrum et al. (2009[Bjerrum, J. V., Ulven, T. & Bond, A. D. (2009). Acta Cryst. E65, o579.]); Löffler et al. (2009[Löffler, P. M. G., Ulven, T. & Bond, A. D. (2009). Acta Cryst. E65, o685.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19FN2O2S

  • Mr = 358.42

  • Monoclinic, P 21 /c

  • a = 15.2748 (7) Å

  • b = 12.0319 (6) Å

  • c = 9.4430 (4) Å

  • β = 102.445 (2)°

  • V = 1694.70 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 180 K

  • 0.20 × 0.20 × 0.08 mm

Data collection
  • Bruker–Nonius X8 APEX-II CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.870, Tmax = 0.983

  • 29053 measured reflections

  • 4157 independent reflections

  • 2816 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.100

  • S = 1.03

  • 4157 reflections

  • 227 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound is useful as an intermediate in the synthesis of antagonists of the prostaglandin D2 receptor CRTH2 (DP2) (Ulven & Kostenis, 2006).

Related literature top

For background literature and synthesis details, see: Ulven & Kostenis (2005, 2006). For related structures, see: Bjerrum et al. (2009); Löffler et al. (2009).

Experimental top

The compound was synthesized as described in Ulven & Kostenis (2005).

Refinement top

H atoms bound to C atoms were placed in idealized positions with C—H = 0.95–1.00 Å and refined as riding with Uiso(H) = 1.2 or 1.5Ueq(C). The methyl group was allowed to rotate about its local threefold axis. The H atom of the NH group was visible in a difference Fourier map but was placed geometrically and refined as riding for the final cycles of refinement with N—H = 0.88 Å and Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids shown at 50% probability for non-H atoms.
[Figure 2] Fig. 2. Unit-cell contents projected along the b axis, showing segregation of carbazole and fluorophenyl groups in the (200) planes. H atoms are omitted.
4-Fluoro-N-methyl-N-(1,2,3,4- tetrahydrocarbazol-3-yl)benzenesulfonamide top
Crystal data top
C19H19FN2O2SF(000) = 752
Mr = 358.42Dx = 1.405 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6906 reflections
a = 15.2748 (7) Åθ = 2.8–24.2°
b = 12.0319 (6) ŵ = 0.22 mm1
c = 9.4430 (4) ÅT = 180 K
β = 102.445 (2)°Plate, yellow
V = 1694.70 (14) Å30.20 × 0.20 × 0.08 mm
Z = 4
Data collection top
Bruker–Nonius X8 APEX-II CCD
diffractometer
4157 independent reflections
Radiation source: fine-focus sealed tube2816 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Thin–slice ω and ϕ scansθmax = 28.4°, θmin = 3.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2020
Tmin = 0.870, Tmax = 0.983k = 1416
29053 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0499P)2 + 0.197P]
where P = (Fo2 + 2Fc2)/3
4157 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C19H19FN2O2SV = 1694.70 (14) Å3
Mr = 358.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.2748 (7) ŵ = 0.22 mm1
b = 12.0319 (6) ÅT = 180 K
c = 9.4430 (4) Å0.20 × 0.20 × 0.08 mm
β = 102.445 (2)°
Data collection top
Bruker–Nonius X8 APEX-II CCD
diffractometer
4157 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2816 reflections with I > 2σ(I)
Tmin = 0.870, Tmax = 0.983Rint = 0.039
29053 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.03Δρmax = 0.28 e Å3
4157 reflectionsΔρmin = 0.36 e Å3
227 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
xyzUiso*/Ueq
S10.18551 (2)0.58771 (3)0.65744 (4)0.03103 (13)
F10.04364 (7)0.90794 (10)0.28602 (13)0.0644 (4)
O110.23235 (7)0.64670 (9)0.78251 (11)0.0366 (3)
O120.13016 (7)0.49488 (9)0.67472 (12)0.0418 (3)
N10.58988 (8)0.75139 (11)0.61606 (14)0.0345 (3)
H10.60600.80920.57060.041*
N20.26020 (8)0.54273 (11)0.57403 (14)0.0332 (3)
C10.64139 (10)0.70104 (13)0.73606 (16)0.0310 (4)
C20.72812 (10)0.72533 (15)0.81236 (18)0.0392 (4)
H2A0.76090.78630.78620.047*
C30.76405 (11)0.65708 (16)0.92717 (19)0.0440 (5)
H3A0.82300.67130.98130.053*
C40.71637 (11)0.56773 (15)0.96612 (18)0.0417 (4)
H4A0.74350.52201.04550.050*
C50.63012 (10)0.54441 (14)0.89130 (17)0.0346 (4)
H5A0.59790.48360.91910.041*
C60.59115 (9)0.61180 (12)0.77416 (16)0.0275 (3)
C70.50635 (10)0.61190 (12)0.67235 (15)0.0260 (3)
C80.42395 (9)0.54333 (13)0.66823 (16)0.0295 (3)
H8A0.41620.52890.76800.035*
H8B0.42940.47110.62080.035*
C90.34359 (10)0.60775 (13)0.58295 (16)0.0285 (4)
H9A0.33780.67670.63930.034*
C100.35930 (11)0.64426 (13)0.43638 (17)0.0348 (4)
H10A0.30360.67710.37840.042*
H10B0.37490.57880.38330.042*
C110.43474 (10)0.72944 (13)0.45470 (17)0.0351 (4)
H11A0.45760.73380.36440.042*
H11B0.41160.80370.47340.042*
C120.50906 (10)0.69691 (13)0.57835 (16)0.0283 (3)
C130.23280 (12)0.46523 (15)0.45307 (19)0.0449 (5)
H13A0.28340.41710.44580.067*
H13B0.21380.50710.36270.067*
H13C0.18290.41950.46980.067*
C140.11647 (9)0.68484 (13)0.54524 (16)0.0297 (4)
C150.04708 (10)0.64712 (15)0.43564 (18)0.0390 (4)
H15A0.03670.56970.42150.047*
C160.00662 (11)0.72264 (16)0.3475 (2)0.0452 (5)
H16A0.05400.69830.27130.054*
C170.00987 (11)0.83361 (16)0.3721 (2)0.0440 (5)
C180.07783 (11)0.87337 (15)0.4788 (2)0.0439 (4)
H18A0.08740.95100.49240.053*
C190.13208 (11)0.79758 (14)0.56618 (18)0.0366 (4)
H19A0.18010.82280.64070.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0310 (2)0.0315 (2)0.0284 (2)0.00616 (17)0.00148 (16)0.00040 (17)
F10.0426 (6)0.0621 (8)0.0852 (9)0.0135 (5)0.0064 (6)0.0321 (6)
O110.0376 (6)0.0446 (7)0.0257 (6)0.0085 (5)0.0024 (5)0.0055 (5)
O120.0394 (6)0.0390 (7)0.0435 (7)0.0114 (5)0.0015 (5)0.0075 (6)
N10.0375 (7)0.0345 (8)0.0320 (8)0.0019 (6)0.0089 (6)0.0072 (6)
N20.0310 (7)0.0302 (7)0.0353 (8)0.0023 (6)0.0001 (6)0.0086 (6)
C10.0323 (8)0.0345 (9)0.0270 (8)0.0057 (7)0.0085 (7)0.0026 (7)
C20.0334 (9)0.0494 (11)0.0352 (10)0.0026 (8)0.0083 (8)0.0054 (8)
C30.0327 (9)0.0608 (13)0.0362 (10)0.0064 (9)0.0025 (8)0.0101 (9)
C40.0408 (10)0.0514 (12)0.0292 (9)0.0172 (9)0.0005 (8)0.0005 (8)
C50.0403 (9)0.0351 (9)0.0277 (9)0.0089 (7)0.0059 (7)0.0025 (7)
C60.0296 (8)0.0301 (9)0.0237 (8)0.0066 (7)0.0076 (6)0.0019 (7)
C70.0313 (8)0.0260 (8)0.0213 (8)0.0058 (6)0.0068 (6)0.0001 (6)
C80.0337 (8)0.0290 (8)0.0250 (8)0.0039 (7)0.0044 (6)0.0030 (6)
C90.0296 (8)0.0272 (9)0.0264 (8)0.0005 (6)0.0006 (6)0.0037 (6)
C100.0420 (9)0.0326 (9)0.0262 (8)0.0060 (8)0.0007 (7)0.0030 (7)
C110.0411 (9)0.0330 (9)0.0288 (9)0.0049 (7)0.0025 (7)0.0085 (7)
C120.0315 (8)0.0288 (8)0.0249 (8)0.0052 (7)0.0070 (6)0.0000 (6)
C130.0530 (11)0.0365 (10)0.0424 (11)0.0068 (8)0.0040 (9)0.0142 (8)
C140.0265 (8)0.0338 (9)0.0296 (8)0.0027 (7)0.0079 (7)0.0009 (7)
C150.0331 (9)0.0374 (10)0.0433 (10)0.0041 (8)0.0016 (8)0.0004 (8)
C160.0312 (9)0.0528 (12)0.0470 (11)0.0038 (8)0.0014 (8)0.0048 (9)
C170.0301 (9)0.0495 (12)0.0541 (12)0.0086 (8)0.0129 (8)0.0181 (9)
C180.0402 (10)0.0322 (10)0.0618 (12)0.0023 (8)0.0167 (9)0.0035 (9)
C190.0325 (8)0.0363 (10)0.0407 (10)0.0032 (7)0.0070 (7)0.0035 (8)
Geometric parameters (Å, º) top
S1—O111.4305 (11)C8—H8A0.990
S1—O121.4312 (11)C8—H8B0.990
S1—N21.6131 (13)C9—C101.520 (2)
S1—C141.7660 (16)C9—H9A1.000
F1—C171.3572 (19)C10—C111.524 (2)
N1—C11.3733 (19)C10—H10A0.990
N1—C121.3751 (19)C10—H10B0.990
N1—H10.880C11—C121.495 (2)
N2—C131.4640 (19)C11—H11A0.990
N2—C91.4817 (19)C11—H11B0.990
C1—C21.396 (2)C13—H13A0.980
C1—C61.411 (2)C13—H13B0.980
C2—C31.376 (2)C13—H13C0.980
C2—H2A0.950C14—C191.384 (2)
C3—C41.392 (3)C14—C151.388 (2)
C3—H3A0.950C15—C161.378 (2)
C4—C51.383 (2)C15—H15A0.950
C4—H4A0.950C16—C171.369 (3)
C5—C61.397 (2)C16—H16A0.950
C5—H5A0.950C17—C181.368 (2)
C6—C71.437 (2)C18—C191.380 (2)
C7—C121.361 (2)C18—H18A0.950
C7—C81.498 (2)C19—H19A0.950
C8—C91.526 (2)
O11—S1—O12119.71 (7)N2—C9—H9A107.1
O11—S1—N2106.80 (6)C10—C9—H9A107.1
O12—S1—N2106.93 (7)C8—C9—H9A107.1
O11—S1—C14107.14 (7)C9—C10—C11110.79 (13)
O12—S1—C14107.08 (7)C9—C10—H10A109.5
N2—S1—C14108.84 (7)C11—C10—H10A109.5
C1—N1—C12109.04 (13)C9—C10—H10B109.5
C1—N1—H1125.5C11—C10—H10B109.5
C12—N1—H1125.5H10A—C10—H10B108.1
C13—N2—C9118.58 (13)C12—C11—C10109.94 (13)
C13—N2—S1118.77 (11)C12—C11—H11A109.7
C9—N2—S1119.01 (10)C10—C11—H11A109.7
N1—C1—C2130.16 (15)C12—C11—H11B109.7
N1—C1—C6107.44 (13)C10—C11—H11B109.7
C2—C1—C6122.39 (14)H11A—C11—H11B108.2
C3—C2—C1117.05 (16)C7—C12—N1109.95 (13)
C3—C2—H2A121.5C7—C12—C11125.57 (14)
C1—C2—H2A121.5N1—C12—C11124.45 (13)
C2—C3—C4121.77 (16)N2—C13—H13A109.5
C2—C3—H3A119.1N2—C13—H13B109.5
C4—C3—H3A119.1H13A—C13—H13B109.5
C5—C4—C3121.13 (16)N2—C13—H13C109.5
C5—C4—H4A119.4H13A—C13—H13C109.5
C3—C4—H4A119.4H13B—C13—H13C109.5
C4—C5—C6118.89 (16)C19—C14—C15120.47 (15)
C4—C5—H5A120.6C19—C14—S1120.04 (12)
C6—C5—H5A120.6C15—C14—S1119.49 (12)
C5—C6—C1118.77 (14)C16—C15—C14119.64 (16)
C5—C6—C7134.35 (15)C16—C15—H15A120.2
C1—C6—C7106.87 (13)C14—C15—H15A120.2
C12—C7—C6106.70 (13)C17—C16—C15118.47 (16)
C12—C7—C8122.71 (13)C17—C16—H16A120.8
C6—C7—C8130.38 (13)C15—C16—H16A120.8
C7—C8—C9108.04 (12)F1—C17—C18118.30 (17)
C7—C8—H8A110.1F1—C17—C16118.42 (17)
C9—C8—H8A110.1C18—C17—C16123.28 (17)
C7—C8—H8B110.1C17—C18—C19118.16 (16)
C9—C8—H8B110.1C17—C18—H18A120.9
H8A—C8—H8B108.4C19—C18—H18A120.9
N2—C9—C10113.79 (12)C18—C19—C14119.97 (16)
N2—C9—C8110.22 (12)C18—C19—H19A120.0
C10—C9—C8111.13 (12)C14—C19—H19A120.0
O11—S1—N2—C13171.11 (11)C7—C8—C9—N2179.29 (12)
O12—S1—N2—C1341.83 (14)C7—C8—C9—C1052.20 (16)
C14—S1—N2—C1373.52 (13)N2—C9—C10—C11168.46 (12)
O11—S1—N2—C930.69 (13)C8—C9—C10—C1166.42 (17)
O12—S1—N2—C9159.97 (11)C9—C10—C11—C1240.74 (18)
C14—S1—N2—C984.67 (12)C6—C7—C12—N10.90 (17)
C12—N1—C1—C2179.04 (16)C8—C7—C12—N1174.28 (13)
C12—N1—C1—C60.25 (16)C6—C7—C12—C11179.17 (14)
N1—C1—C2—C3177.84 (15)C8—C7—C12—C114.0 (2)
C6—C1—C2—C30.8 (2)C1—N1—C12—C70.42 (17)
C1—C2—C3—C40.1 (2)C1—N1—C12—C11178.71 (14)
C2—C3—C4—C50.6 (3)C10—C11—C12—C77.3 (2)
C3—C4—C5—C60.5 (2)C10—C11—C12—N1174.63 (14)
C4—C5—C6—C10.2 (2)O11—S1—C14—C1916.81 (14)
C4—C5—C6—C7178.64 (16)O12—S1—C14—C19146.41 (13)
N1—C1—C6—C5178.01 (13)N2—S1—C14—C1998.34 (14)
C2—C1—C6—C50.9 (2)O11—S1—C14—C15163.65 (12)
N1—C1—C6—C70.79 (16)O12—S1—C14—C1534.05 (14)
C2—C1—C6—C7179.70 (14)N2—S1—C14—C1581.21 (13)
C5—C6—C7—C12177.49 (16)C19—C14—C15—C160.1 (2)
C1—C6—C7—C121.04 (16)S1—C14—C15—C16179.68 (13)
C5—C6—C7—C87.8 (3)C14—C15—C16—C170.6 (2)
C1—C6—C7—C8173.64 (14)C15—C16—C17—F1179.37 (15)
C12—C7—C8—C918.43 (19)C15—C16—C17—C180.9 (3)
C6—C7—C8—C9155.51 (15)F1—C17—C18—C19179.96 (14)
C13—N2—C9—C1036.64 (19)C16—C17—C18—C190.3 (3)
S1—N2—C9—C10121.59 (13)C17—C18—C19—C140.5 (2)
C13—N2—C9—C888.96 (16)C15—C14—C19—C180.7 (2)
S1—N2—C9—C8112.81 (12)S1—C14—C19—C18179.72 (12)

Experimental details

Crystal data
Chemical formulaC19H19FN2O2S
Mr358.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)180
a, b, c (Å)15.2748 (7), 12.0319 (6), 9.4430 (4)
β (°) 102.445 (2)
V3)1694.70 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.20 × 0.20 × 0.08
Data collection
DiffractometerBruker–Nonius X8 APEX-II CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.870, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
29053, 4157, 2816
Rint0.039
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.100, 1.03
No. of reflections4157
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.36

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We are grateful to the Danish Natural Sciences Research Council and the Carlsberg Foundation for provision of the X-ray equipment.

References

First citationBjerrum, J. V., Ulven, T. & Bond, A. D. (2009). Acta Cryst. E65, o579.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLöffler, P. M. G., Ulven, T. & Bond, A. D. (2009). Acta Cryst. E65, o685.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationUlven, T. & Kostenis, E. (2005). J. Med. Chem. 48, 897–900.  Web of Science CrossRef PubMed CAS Google Scholar
First citationUlven, T. & Kostenis, E. (2006). Curr. Top. Med. Chem. 6, 1427–1444.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds