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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 3| March 2013| Page o355
doi:10.1107/S1600536813003310

4-Nitro­phenyl N-(2-sulfamoylphen­yl)carbamate

Wenying Yua and Chenglong Lia*

aDivision of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA
*Correspondence e-mail: li.728@osu.edu

(Received 24 January 2013; accepted 31 January 2013; online 6 February 2013)

In the title mol­ecule, C13H11N3O6S, the dihedral angle between the benzene rings is 35.52 (8)°. An intra­molecular N—H⋯O hydrogen bond forms an S(6) ring. In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds into chains along [101] incorporating R22(8) and R22(16) rings.

Related literature

For the synthesis, see: Mallakpour & Rafiee (2007[Mallakpour, L. & Rafiee, Z. (2007). Synth. Commun. 37, 1927-1934.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11N3O6S

  • Mr = 337.31

  • Triclinic, [P \overline 1]

  • a = 8.2730 (2) Å

  • b = 8.4881 (2) Å

  • c = 10.4288 (2) Å

  • α = 95.178 (1)°

  • β = 103.507 (1)°

  • γ = 94.109 (1)°

  • V = 705.91 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 180 K

  • 0.27 × 0.27 × 0.12 mm
Data collection

  • Nonius KappaCCD diffractometer

  • 21157 measured reflections

  • 3227 independent reflections

  • 2473 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.05

  • 3227 reflections

  • 220 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N1⋯O3 0.802 (19) 2.02 (2) 2.6962 (18) 142.4 (18)
N2—H1N2⋯O1i 0.83 (2) 2.15 (2) 2.975 (2) 175.1 (19)
N2—H2N2⋯O4ii 0.89 (2) 2.10 (2) 2.967 (2) 165 (2)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+1.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813003310/lh5580sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003310/lh5580Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003310/lh5580Isup3.cml

checkCIF report


Comment top

The title compound (I) is an important intermediate in drug discovery. It was obtained by reacting 2-aminobenzenesulfonamide with 4-nitrophenyl carbonochloridate through a modified procedure by Mallakpour & Rafiee (2007). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the two benzene rings (C1-C6 and C8-C13) is 35.52 (8)°. In the crystal, molecules are linked via N—H···O hydrogen bonds (Fig.2) into one-dimensional chains along [101], incorporating R22(8) and R22(16) rings (Bernstein et al., 1995). There is also an intramolecular N—H···O hydrogen bond forming an S(6) ring.

Related literature top

For the synthesis, see: Mallakpour & Rafiee (2007). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).

Experimental top

All chemicals were obtained from commercial sources and used directly without further purification. 2-Aminobenzenesulfonamide (0.72 g, 1 mmol) was dissolved in 10 ml of dry tetrahydrofuran/ dichloromethane (1:1 v/v), then cooled to 273K. 4-Nitrophenyl carbonochloridate (0.2 g, 1 mmol) was added to the solution in a round-bottom flask, followed by triethylamine (0.14 ml, 1 mmol). The solution was stirred for 1 h at the same temperature and then 2h at room temperature. White solid powder precipitated out (0.307 g, yield: 91%). This was was filtered off, washed with distilled water and dried over anhydrous Na2SO4. It was characterized by its mass spectrum to be the title compound (I). Colorless plate crystals suitable for X-ray diffraction analysis were grown from a co-solvent system methanol/dichloromethane (1:20 v/v) solution by slow evaporation at 277K for a week.

Refinement top

H atoms bonded to C atoms were located in difference Fourier maps and were subsequently placed in idealized positions with C—H distances of 0.95Å. They were included in the refinemnt in a riding-motion approxmation with Uiso(H) = 1.2Ueq(C). H atoms bonded to N atoms were refined independently with isotropic displacement parameters.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. Partial crystal packing of the title compound showing the hydrogen bonds as dashed lines.
4-Nitrophenyl N-(2-sulfamoylphenyl)carbamate top
Crystal data top
C13H11N3O6SZ = 2
Mr = 337.31F(000) = 348
Triclinic, P1Dx = 1.587 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2730 (2) ÅCell parameters from 3223 reflections
b = 8.4881 (2) Åθ = 2.0–27.5°
c = 10.4288 (2) ŵ = 0.27 mm−1
α = 95.178 (1)°T = 180 K
β = 103.507 (1)°Plate, colourless
γ = 94.109 (1)°0.27 × 0.27 × 0.12 mm
V = 705.91 (3) Å3
Data collection top
Nonius KappaCCD
diffractometer		2473 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590Rint = 0.037
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
Detector resolution: 9 pixels mm-1h = −10→10
ϕ and ω scansk = −11→11
21157 measured reflectionsl = −13→13
3227 independent reflections
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.051P)2 + 0.1167P]
where P = (Fo2 + 2Fc2)/3
3227 reflections(Δ/σ)max = 0.001
220 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Crystal data top
C13H11N3O6Sγ = 94.109 (1)°
Mr = 337.31V = 705.91 (3) Å3
Triclinic, P1Z = 2
a = 8.2730 (2) ÅMo Kα radiation
b = 8.4881 (2) ŵ = 0.27 mm−1
c = 10.4288 (2) ÅT = 180 K
α = 95.178 (1)°0.27 × 0.27 × 0.12 mm
β = 103.507 (1)°
Data collection top
Nonius KappaCCD
diffractometer		2473 reflections with I > 2σ(I)
21157 measured reflectionsRint = 0.037
3227 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.23 e Å−3
3227 reflectionsΔρmin = −0.40 e Å−3
220 parameters
Special details top

Experimental. All work was done at 180 K using an Oxford Cryosystems Cryostream Cooler.

The data collection strategy was set up to measure a hemisphere of reciprocal space with a redundancy factor of 3.6, which means that 90% of these reflections were measured at least 3.6 times. Phi and omega scans with a frame width of 2.0 degrees were used. Data integration was done with DENZO, and scaling and merging of the data was done with SCALEPACK.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. The hydrogen atoms bonded to the nitrogen atoms were located on difference electron density maps, added to the model at these positions and refined isotropically. All three N—H groups are involved in intra and intermolecular hydrogen bonds with the oxygen atoms bonded to the S atom and with the oxygen atom of the carbonyl group. The rest of the hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded atom).

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 > 2σ(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
C10.18448 (19)1.06402 (18)0.95047 (15)0.0243 (3)
C20.09787 (19)1.05966 (18)0.81639 (15)0.0231 (3)
C30.0295 (2)1.19437 (19)0.76876 (16)0.0283 (4)
H3−0.02941.19010.67850.034*
C40.0464 (2)1.3342 (2)0.85148 (17)0.0333 (4)
H4−0.00041.42590.81860.04*
C50.1322 (2)1.3391 (2)0.98272 (17)0.0339 (4)
H50.14461.43521.03980.041*
C60.2001 (2)1.2067 (2)1.03241 (16)0.0314 (4)
H60.2581.21271.12310.038*
C70.3599 (2)0.91756 (19)1.11483 (16)0.0261 (4)
C80.4744 (2)0.71841 (18)1.24599 (16)0.0257 (4)
C90.5823 (2)0.6064 (2)1.22946 (17)0.0318 (4)
H90.59040.5681.1430.038*
C100.6788 (2)0.5501 (2)1.33996 (16)0.0304 (4)
H100.7540.47271.33090.036*
C110.66298 (19)0.60948 (18)1.46359 (16)0.0246 (3)
C120.5552 (2)0.72220 (18)1.48113 (16)0.0269 (4)
H120.54750.7611.56760.032*
C130.4586 (2)0.77744 (19)1.37010 (16)0.0278 (4)
H130.38290.85441.3790.033*
N10.24540 (18)0.92648 (17)1.00104 (14)0.0282 (3)
H1N10.211 (2)0.845 (2)0.9546 (19)0.033 (5)*
N20.2259 (2)0.92531 (18)0.61879 (15)0.0294 (3)
H1N20.322 (3)0.939 (2)0.668 (2)0.039 (6)*
H2N20.197 (3)0.993 (3)0.559 (2)0.053 (6)*
N30.76147 (17)0.54610 (16)1.58042 (13)0.0288 (3)
O10.44001 (14)1.02495 (13)1.19174 (12)0.0354 (3)
O20.37252 (14)0.75997 (13)1.12918 (11)0.0314 (3)
O30.11646 (15)0.75518 (13)0.76379 (11)0.0333 (3)
O4−0.07382 (14)0.89165 (14)0.60048 (11)0.0333 (3)
O50.73699 (16)0.58990 (14)1.68935 (11)0.0365 (3)
O60.86034 (16)0.45021 (16)1.56352 (13)0.0425 (3)
S0.08224 (5)0.89358 (5)0.69623 (4)0.02568 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0236 (8)0.0292 (8)0.0209 (8)0.0074 (6)0.0035 (6)0.0071 (6)
C20.0215 (8)0.0268 (8)0.0206 (8)0.0048 (6)0.0025 (6)0.0049 (6)
C30.0275 (9)0.0360 (9)0.0221 (8)0.0121 (7)0.0025 (7)0.0089 (7)
C40.0383 (10)0.0341 (9)0.0305 (9)0.0182 (8)0.0075 (8)0.0093 (7)
C50.0412 (10)0.0333 (9)0.0279 (9)0.0159 (8)0.0070 (8)0.0007 (7)
C60.0363 (10)0.0379 (10)0.0199 (8)0.0139 (8)0.0033 (7)0.0035 (7)
C70.0253 (8)0.0294 (9)0.0239 (8)0.0067 (7)0.0037 (7)0.0077 (7)
C80.0259 (8)0.0249 (8)0.0236 (8)0.0019 (7)−0.0017 (7)0.0091 (7)
C90.0378 (10)0.0363 (10)0.0220 (8)0.0094 (8)0.0061 (7)0.0054 (7)
C100.0314 (9)0.0331 (9)0.0282 (9)0.0111 (7)0.0061 (7)0.0077 (7)
C110.0233 (8)0.0249 (8)0.0231 (8)0.0003 (6)−0.0005 (6)0.0083 (6)
C120.0309 (9)0.0264 (8)0.0221 (8)0.0019 (7)0.0041 (7)0.0028 (6)
C130.0280 (9)0.0263 (8)0.0291 (9)0.0070 (7)0.0042 (7)0.0058 (7)
N10.0338 (8)0.0256 (8)0.0213 (7)0.0075 (6)−0.0031 (6)0.0041 (6)
N20.0271 (8)0.0359 (8)0.0218 (7)0.0047 (6)−0.0002 (6)0.0005 (6)
N30.0300 (8)0.0277 (7)0.0254 (8)0.0004 (6)−0.0011 (6)0.0082 (6)
O10.0332 (7)0.0303 (6)0.0346 (7)0.0026 (5)−0.0094 (6)0.0073 (5)
O20.0356 (7)0.0277 (6)0.0251 (6)0.0060 (5)−0.0068 (5)0.0080 (5)
O30.0436 (7)0.0251 (6)0.0262 (6)0.0035 (5)−0.0025 (5)0.0055 (5)
O40.0273 (6)0.0382 (7)0.0276 (6)−0.0025 (5)−0.0065 (5)0.0071 (5)
O50.0470 (8)0.0380 (7)0.0210 (6)0.0003 (6)0.0014 (6)0.0053 (5)
O60.0425 (8)0.0487 (8)0.0364 (7)0.0199 (6)0.0018 (6)0.0135 (6)
S0.0258 (2)0.0270 (2)0.0203 (2)0.00131 (16)−0.00231 (16)0.00350 (16)
Geometric parameters (Å, º) top
C1—C61.397 (2)C9—C101.385 (2)
C1—N11.402 (2)C9—H90.95
C1—C21.410 (2)C10—C111.380 (2)
C2—C31.392 (2)C10—H100.95
C2—S1.7758 (16)C11—C121.382 (2)
C3—C41.381 (2)C11—N31.468 (2)
C3—H30.95C12—C131.385 (2)
C4—C51.382 (2)C12—H120.95
C4—H40.95C13—H130.95
C5—C61.381 (2)N1—H1N10.802 (19)
C5—H50.95N2—S1.6063 (16)
C6—H60.95N2—H1N20.83 (2)
C7—O11.2028 (19)N2—H2N20.89 (2)
C7—N11.346 (2)N3—O61.2246 (17)
C7—O21.3680 (19)N3—O51.2296 (18)
C8—C91.376 (2)O3—S1.4354 (12)
C8—C131.384 (2)O4—S1.4339 (11)
C8—O21.3999 (18)
C6—C1—N1121.20 (14)C11—C10—H10120.9
C6—C1—C2118.12 (14)C9—C10—H10120.9
N1—C1—C2120.60 (14)C10—C11—C12122.69 (15)
C3—C2—C1120.27 (14)C10—C11—N3118.21 (14)
C3—C2—S115.83 (12)C12—C11—N3119.07 (15)
C1—C2—S123.72 (12)C11—C12—C13118.70 (15)
C4—C3—C2120.66 (15)C11—C12—H12120.7
C4—C3—H3119.7C13—C12—H12120.7
C2—C3—H3119.7C8—C13—C12118.75 (15)
C3—C4—C5119.19 (15)C8—C13—H13120.6
C3—C4—H4120.4C12—C13—H13120.6
C5—C4—H4120.4C7—N1—C1127.37 (15)
C6—C5—C4121.18 (16)C7—N1—H1N1117.1 (14)
C6—C5—H5119.4C1—N1—H1N1115.5 (14)
C4—C5—H5119.4S—N2—H1N2113.9 (14)
C5—C6—C1120.58 (15)S—N2—H2N2111.1 (14)
C5—C6—H6119.7H1N2—N2—H2N2118 (2)
C1—C6—H6119.7O6—N3—O5123.82 (14)
O1—C7—N1128.09 (15)O6—N3—C11118.24 (14)
O1—C7—O2124.49 (14)O5—N3—C11117.92 (13)
N1—C7—O2107.42 (14)C7—O2—C8118.65 (12)
C9—C8—C13122.16 (14)O4—S—O3118.58 (7)
C9—C8—O2115.74 (14)O4—S—N2106.39 (8)
C13—C8—O2121.93 (14)O3—S—N2107.65 (8)
C8—C9—C10119.44 (15)O4—S—C2107.69 (7)
C8—C9—H9120.3O3—S—C2108.65 (7)
C10—C9—H9120.3N2—S—C2107.39 (8)
C11—C10—C9118.26 (15)
C6—C1—C2—C3−0.5 (2)C11—C12—C13—C8−0.4 (2)
N1—C1—C2—C3176.32 (15)O1—C7—N1—C1−4.9 (3)
C6—C1—C2—S174.44 (13)O2—C7—N1—C1175.73 (15)
N1—C1—C2—S−8.8 (2)C6—C1—N1—C7−19.4 (3)
C1—C2—C3—C40.5 (3)C2—C1—N1—C7163.86 (16)
S—C2—C3—C4−174.82 (13)C10—C11—N3—O64.1 (2)
C2—C3—C4—C5−0.1 (3)C12—C11—N3—O6−177.65 (14)
C3—C4—C5—C6−0.4 (3)C10—C11—N3—O5−174.26 (15)
C4—C5—C6—C10.4 (3)C12—C11—N3—O53.9 (2)
N1—C1—C6—C5−176.73 (16)O1—C7—O2—C85.7 (2)
C2—C1—C6—C50.1 (3)N1—C7—O2—C8−174.90 (14)
C13—C8—C9—C10−0.1 (3)C9—C8—O2—C7−132.47 (16)
O2—C8—C9—C10−175.35 (15)C13—C8—O2—C752.2 (2)
C8—C9—C10—C11−0.1 (3)C3—C2—S—O4−35.25 (15)
C9—C10—C11—C120.0 (3)C1—C2—S—O4149.62 (14)
C9—C10—C11—N3178.11 (15)C3—C2—S—O3−164.86 (12)
C10—C11—C12—C130.3 (3)C1—C2—S—O320.01 (16)
N3—C11—C12—C13−177.85 (14)C3—C2—S—N278.97 (14)
C9—C8—C13—C120.3 (3)C1—C2—S—N2−96.16 (15)
O2—C8—C13—C12175.31 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O30.802 (19)2.02 (2)2.6962 (18)142.4 (18)
N1—H1N1···S0.802 (19)2.736 (19)3.1283 (14)112.2 (15)
N2—H1N2···O1i0.83 (2)2.15 (2)2.975 (2)175.1 (19)
N2—H2N2···O4ii0.89 (2)2.10 (2)2.967 (2)165 (2)
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formulaC13H11N3O6S
Mr337.31
Crystal system, space groupTriclinic, P1
Temperature (K)180
a, b, c (Å)8.2730 (2), 8.4881 (2), 10.4288 (2)
α, β, γ (°)95.178 (1), 103.507 (1), 94.109 (1)
V (Å3)705.91 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.27 × 0.27 × 0.12
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		21157, 3227, 2473
Rint0.037
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.05
No. of reflections3227
No. of parameters220
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.23, −0.40

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O30.802 (19)2.02 (2)2.6962 (18)142.4 (18)
N1—H1N1···S0.802 (19)2.736 (19)3.1283 (14)112.2 (15)
N2—H1N2···O1i0.83 (2)2.15 (2)2.975 (2)175.1 (19)
N2—H2N2···O4ii0.89 (2)2.10 (2)2.967 (2)165 (2)
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x, −y+2, −z+1.
 

Acknowledgements

We are grateful to Dr Sihui Long for providing the help with the crystallization and also in editing this paper. We are grateful to Dr Judith Ann Gallucci for the X-ray crystallographic experiments.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationMallakpour, L. & Rafiee, Z. (2007). Synth. Commun. 37, 1927–1934.  Web of Science CrossRef CAS Google Scholar
 First citationNonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals 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.

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ISSN: 2056-9890
Volume 69| Part 3| March 2013| Page o355
doi:10.1107/S1600536813003310
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