Literature DB >> 21583521

4-[(Z)-(2-Eth-oxy-4-oxochroman-3-yl-idene)methyl-amino]benzene-sulfonamide monohydrate.

M Nawaz Tahir, Saeed Ahmad Nagra, Muhammed Imran, Javed Iqbal.   

Abstract

In the mol-ecule of the title compound, C(18)H(18)N(2)O(5)S·H(2)O, the heterocyclic ring adopts a twisted conformation, while the aromatic rings are oriented at a dihedral angle of 45.46 (3)°. Intra-molecular C-H⋯O and N-H⋯O inter-actions result in the formations of planar five- and six-membered rings. In the crystal structure, N-H⋯O hydrogen bonds link the NH(2) and SO(2) groups through R(2) (2)(8) ring motifs, while C-H⋯O and N-H⋯O n class="Chemical">hydrogen bonds result in the formation of R(2) (1)(7) ring motifs. N-H⋯O and O-H⋯O hydrogen bonds link the uncoordinated water mol-ecules, forming a polymeric network. A weak C-H⋯π inter-action is also present.

Entities:  

Year:  2009        PMID： 21583521      PMCID： PMC2977350          DOI： 10.1107/S1600536809026154

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Al-Zaydi et al. (2007 ▶); Chohan et al. (2008 ▶, 2009 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For ring motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H18N2O5S·n class="Chemical">H2O M = 392.42 Triclinic, a = 8.2727 (6) Å b = 10.0166 (8) Å c = 11.5830 (9) Å α = 102.480 (5)° β = 97.049 (4)° γ = 96.731 (4)° V = 919.77 (12) Å3 Z = 2 Mo Kα radiation μ = 0.21 mm−1 T = 296 K 0.28 × 0.10 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.973, T max = 0.982 18417 measured reflections 4729 independent reflections 2022 reflections with I > 2σ(I) R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.125 S = 1.00 4729 reflections 260 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.25 e Å−3 Δρmin = −0.22 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026154/hk2734sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026154/hk2734Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H18N2O5S·H2OZ = 2
Mr = 392.42F(000) = 412
Triclinic, P1Dx = 1.417 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2727 (6) ÅCell parameters from 4729 reflections
b = 10.0166 (8) Åθ = 2.4–28.8°
c = 11.5830 (9) ŵ = 0.21 mm−1
α = 102.480 (5)°T = 296 K
β = 97.049 (4)°Needle, yellow
γ = 96.731 (4)°0.28 × 0.10 × 0.09 mm
V = 919.77 (12) Å3
Bruker Kappa APEXII CCD diffractometer4729 independent reflections
Radiation source: fine-focus sealed tube2022 reflections with I > 2σ(I)
graphiteRint = 0.070
Detector resolution: 7.40 pixels mm-1θmax = 28.8°, θmin = 2.4°
ω scansh = −11→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −13→13
Tmin = 0.973, Tmax = 0.982l = −15→15
18417 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0427P)2] where P = (Fo2 + 2Fc2)/3
4729 reflections(Δ/σ)max < 0.001
260 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
S10.65357 (9)0.03978 (8)−0.32059 (7)0.0444 (3)
O10.7917 (2)0.0360 (2)−0.23543 (17)0.0608 (8)
O20.5862 (2)−0.08348 (18)−0.41008 (16)0.0501 (7)
O3−0.2219 (2)0.19797 (19)0.24854 (17)0.0513 (7)
O4−0.1312 (2)0.3631 (2)−0.03129 (17)0.0580 (8)
O50.0431 (2)0.3149 (2)0.31661 (16)0.0510 (7)
O60.1102 (3)0.5917 (2)0.2582 (2)0.0705 (9)
N10.1144 (3)0.2091 (2)−0.0546 (2)0.0478 (9)
N20.7070 (3)0.1526 (3)−0.3923 (3)0.0559 (10)
C1−0.3062 (3)0.3009 (3)0.2233 (3)0.0412 (10)
C2−0.4381 (3)0.3273 (3)0.2838 (3)0.0558 (11)
C3−0.5269 (4)0.4275 (3)0.2598 (3)0.0628 (11)
C4−0.4871 (4)0.5029 (3)0.1782 (3)0.0588 (12)
C5−0.3605 (3)0.4734 (3)0.1166 (3)0.0491 (11)
C6−0.2684 (3)0.3703 (3)0.1377 (2)0.0376 (9)
C7−0.1412 (3)0.3271 (3)0.0643 (2)0.0403 (9)
C8−0.0367 (3)0.2398 (3)0.1090 (2)0.0405 (9)
C9−0.0540 (3)0.2094 (3)0.2276 (3)0.0470 (11)
C100.0843 (3)0.1890 (3)0.0508 (3)0.0469 (11)
C110.2442 (3)0.1665 (3)−0.1153 (3)0.0424 (10)
C120.2237 (3)0.1498 (3)−0.2378 (3)0.0479 (11)
C130.3481 (3)0.1123 (3)−0.3005 (2)0.0463 (10)
C140.4946 (3)0.0904 (3)−0.2408 (2)0.0392 (9)
C150.5153 (3)0.1090 (3)−0.1186 (3)0.0455 (10)
C160.3895 (3)0.1473 (3)−0.0555 (2)0.0471 (10)
C170.0555 (4)0.2828 (4)0.4337 (3)0.0756 (16)
C180.1854 (4)0.3812 (4)0.5152 (3)0.0916 (16)
H10.047550.25264−0.089690.0574*
H2−0.465460.277650.339620.0668*
H3−0.616090.445130.299400.0754*
H4−0.546060.573260.165350.0707*
H5−0.335110.522370.059870.0590*
H9−0.013 (3)0.120 (3)0.243 (2)0.0563*
H100.150630.136530.087530.0562*
H120.125140.16395−0.278150.0573*
H130.334040.10157−0.383010.0557*
H150.614130.09592−0.077950.0545*
H160.403980.159970.027220.0565*
H17A0.080480.189550.427670.0909*
H17B−0.048510.288400.463820.0909*
H18A0.166030.473670.514330.1377*
H18B0.289920.367450.490300.1377*
H18C0.186040.367520.594770.1377*
H210.757 (3)0.234 (3)−0.342 (3)0.0671*
H220.634 (4)0.155 (3)−0.450 (3)0.0671*
H610.086 (4)0.508 (4)0.274 (3)0.0846*
H620.110 (4)0.586 (3)0.178 (3)0.0846*
U11U22U33U12U13U23
S10.0396 (4)0.0481 (5)0.0453 (5)0.0093 (3)0.0075 (3)0.0083 (4)
O10.0433 (11)0.0813 (16)0.0562 (14)0.0244 (10)0.0001 (10)0.0088 (11)
O20.0598 (12)0.0394 (12)0.0470 (12)0.0060 (10)0.0096 (10)0.0015 (10)
O30.0436 (11)0.0510 (13)0.0676 (14)0.0071 (10)0.0156 (10)0.0278 (11)
O40.0622 (13)0.0742 (15)0.0450 (13)0.0114 (11)0.0120 (10)0.0273 (12)
O50.0523 (12)0.0600 (14)0.0410 (12)0.0048 (10)0.0064 (10)0.0149 (11)
O60.0939 (17)0.0584 (15)0.0519 (14)−0.0130 (13)0.0058 (13)0.0132 (13)
N10.0435 (14)0.0551 (16)0.0440 (15)0.0087 (12)0.0052 (12)0.0098 (13)
N20.0537 (17)0.0521 (17)0.0577 (19)−0.0052 (14)0.0098 (13)0.0099 (15)
C10.0357 (15)0.0402 (17)0.0482 (18)0.0026 (14)0.0053 (14)0.0140 (15)
C20.0441 (18)0.069 (2)0.063 (2)0.0092 (17)0.0175 (16)0.0283 (18)
C30.0491 (19)0.079 (2)0.067 (2)0.0201 (19)0.0192 (17)0.020 (2)
C40.061 (2)0.058 (2)0.060 (2)0.0250 (17)0.0078 (18)0.0118 (18)
C50.0515 (18)0.0467 (19)0.0511 (19)0.0082 (16)0.0034 (16)0.0176 (16)
C60.0356 (15)0.0384 (16)0.0357 (16)−0.0013 (13)0.0018 (13)0.0079 (14)
C70.0411 (16)0.0420 (17)0.0328 (16)−0.0036 (14)0.0037 (14)0.0045 (14)
C80.0365 (15)0.0442 (17)0.0399 (17)0.0053 (14)0.0063 (14)0.0079 (14)
C90.0425 (17)0.052 (2)0.050 (2)0.0096 (16)0.0121 (15)0.0154 (17)
C100.0437 (17)0.0494 (19)0.0453 (19)0.0031 (15)0.0011 (15)0.0114 (15)
C110.0353 (16)0.0406 (17)0.0481 (19)0.0032 (14)0.0076 (15)0.0043 (14)
C120.0400 (16)0.059 (2)0.0435 (19)0.0105 (15)−0.0002 (15)0.0115 (16)
C130.0452 (17)0.059 (2)0.0350 (16)0.0122 (15)0.0045 (14)0.0102 (15)
C140.0375 (15)0.0382 (16)0.0401 (17)0.0032 (13)0.0050 (13)0.0073 (14)
C150.0420 (16)0.0506 (19)0.0392 (18)0.0047 (14)−0.0021 (14)0.0065 (15)
C160.0441 (17)0.062 (2)0.0294 (15)0.0028 (15)0.0008 (14)0.0035 (14)
C170.087 (3)0.094 (3)0.053 (2)0.018 (2)0.015 (2)0.028 (2)
C180.099 (3)0.116 (3)0.051 (2)0.013 (3)−0.010 (2)0.014 (2)
S1—O11.425 (2)C8—C101.361 (4)
S1—O21.433 (2)C8—C91.490 (4)
S1—N21.594 (3)C11—C161.367 (4)
S1—C141.759 (3)C11—C121.379 (5)
O3—C11.372 (3)C12—C131.373 (4)
O3—C91.435 (3)C13—C141.385 (4)
O4—C71.245 (3)C14—C151.374 (4)
O5—C91.397 (4)C15—C161.387 (4)
O5—C171.454 (4)C17—C181.455 (5)
O6—H620.92 (3)C2—H20.9300
O6—H610.90 (4)C3—H30.9300
N1—C111.412 (4)C4—H40.9300
N1—C101.327 (4)C5—H50.9300
N1—H10.8600C9—H91.04 (3)
N2—H210.91 (3)C10—H100.9300
N2—H220.85 (3)C12—H120.9300
C1—C61.374 (4)C13—H130.9300
C1—C21.388 (4)C15—H150.9300
C2—C31.367 (4)C16—H160.9300
C3—C41.378 (5)C17—H17B0.9700
C4—C51.363 (4)C17—H17A0.9700
C5—C61.398 (4)C18—H18C0.9600
C6—C71.478 (3)C18—H18A0.9600
C7—C81.429 (4)C18—H18B0.9600
O1···N1i3.239 (3)C7···H12.5600
O2···C13ii3.418 (3)C7···H612.98 (4)
O2···N2ii3.027 (3)C7···H623.06 (3)
O2···C2iii3.300 (4)C8···H612.93 (4)
O3···C13iii3.364 (4)C9···H612.99 (4)
O4···O4iv3.181 (3)C10···H162.7300
O4···O6iv2.784 (3)C11···H5iv3.0300
O4···N12.696 (3)C12···H9iii3.02 (3)
O5···C63.281 (3)C16···H102.7400
O5···O62.999 (3)H1···O42.0400
O6···C73.374 (3)H1···O1vii2.9200
O6···O52.999 (3)H1···C72.5600
O6···N2v2.838 (4)H1···H122.3700
O6···O4iv2.784 (3)H1···H62iv2.5000
O1···H152.5000H2···O2iii2.4200
O1···H9vi2.54 (3)H3···O6vii2.8900
O1···H1i2.9200H4···H5ix2.6000
O1···H10vi2.7200H5···C5ix3.0500
O2···H22ii2.22 (3)H5···C4ix2.9100
O2···H13ii2.5400H5···O42.6200
O2···H2iii2.4200H5···C11iv3.0300
O3···H17B2.6300H5···H4ix2.6000
O4···H52.6200H9···H102.4000
O4···H62iv1.90 (3)H9···C12iii3.02 (3)
O4···H12.0400H9···H17A2.1200
O5···H612.10 (4)H9···O1vi2.54 (3)
O6···H3i2.8900H10···C162.7400
O6···H21v1.94 (3)H10···H162.2900
N1···O1vii3.239 (3)H10···O1vi2.7200
N1···O42.696 (3)H10···H92.4000
N2···O6v2.838 (4)H12···H12.3700
N2···O2ii3.027 (3)H13···O2ii2.5400
C2···C18viii3.571 (5)H15···O12.5000
C2···O2iii3.300 (4)H15···C7i2.9300
C4···C5ix3.560 (5)H16···C1i3.0600
C5···C5ix3.505 (4)H16···C102.7300
C5···C4ix3.560 (5)H16···H102.2900
C6···C16vii3.579 (4)H17A···H92.1200
C6···O53.281 (3)H17B···O32.6300
C7···O63.374 (3)H21···H62v2.37 (5)
C7···C15vii3.522 (4)H21···O6v1.94 (3)
C13···O3iii3.364 (4)H22···O2ii2.22 (3)
C13···O2ii3.418 (3)H61···O52.10 (4)
C15···C7i3.522 (4)H61···C72.98 (4)
C16···C6i3.579 (4)H61···C82.93 (4)
C18···C2viii3.571 (5)H61···C92.99 (4)
C1···H16vii3.0600H62···C73.06 (3)
C4···H5ix2.9100H62···O4iv1.90 (3)
C5···H5ix3.0500H62···H1iv2.5000
C7···H15vii2.9300H62···H21v2.37 (5)
O1—S1—O2118.76 (12)C12—C13—C14120.0 (2)
O1—S1—N2107.72 (14)S1—C14—C13120.33 (17)
O1—S1—C14107.54 (11)S1—C14—C15120.1 (2)
O2—S1—N2105.54 (15)C13—C14—C15119.5 (2)
O2—S1—C14107.37 (12)C14—C15—C16120.3 (2)
N2—S1—C14109.74 (15)C11—C16—C15119.8 (2)
C1—O3—C9115.5 (2)O5—C17—C18109.0 (3)
C9—O5—C17112.4 (2)C1—C2—H2121.00
H61—O6—H62112 (3)C3—C2—H2121.00
C10—N1—C11127.0 (2)C4—C3—H3119.00
C10—N1—H1116.00C2—C3—H3119.00
C11—N1—H1117.00C5—C4—H4120.00
S1—N2—H22113 (2)C3—C4—H4120.00
H21—N2—H22119 (3)C4—C5—H5120.00
S1—N2—H21112 (2)C6—C5—H5120.00
O3—C1—C2117.0 (3)O3—C9—H9105.4 (14)
O3—C1—C6122.0 (2)O5—C9—H9104.0 (14)
C2—C1—C6121.0 (3)C8—C9—H9116.5 (13)
C1—C2—C3118.8 (3)C8—C10—H10118.00
C2—C3—C4121.4 (3)N1—C10—H10118.00
C3—C4—C5119.4 (3)C11—C12—H12120.00
C4—C5—C6120.7 (3)C13—C12—H12120.00
C1—C6—C7119.4 (3)C12—C13—H13120.00
C1—C6—C5118.7 (2)C14—C13—H13120.00
C5—C6—C7121.8 (2)C16—C15—H15120.00
O4—C7—C6120.9 (2)C14—C15—H15120.00
O4—C7—C8123.5 (2)C15—C16—H16120.00
C6—C7—C8115.5 (2)C11—C16—H16120.00
C7—C8—C10122.8 (2)O5—C17—H17A110.00
C7—C8—C9118.8 (2)C18—C17—H17A110.00
C9—C8—C10118.3 (3)C18—C17—H17B110.00
O3—C9—O5109.9 (2)O5—C17—H17B110.00
O5—C9—C8108.6 (2)H17A—C17—H17B108.00
O3—C9—C8112.1 (2)C17—C18—H18B109.00
N1—C10—C8124.6 (3)C17—C18—H18C110.00
C12—C11—C16120.1 (2)C17—C18—H18A109.00
N1—C11—C16121.8 (3)H18A—C18—H18C109.00
N1—C11—C12118.1 (2)H18B—C18—H18C109.00
C11—C12—C13120.3 (2)H18A—C18—H18B109.00
O1—S1—C14—C13175.5 (2)C4—C5—C6—C7174.1 (3)
O1—S1—C14—C15−4.3 (3)C1—C6—C7—O4162.4 (3)
O2—S1—C14—C13−55.6 (3)C1—C6—C7—C8−15.9 (4)
O2—S1—C14—C15124.6 (2)C5—C6—C7—O4−12.7 (4)
N2—S1—C14—C1358.6 (3)C5—C6—C7—C8169.0 (3)
N2—S1—C14—C15−121.2 (3)O4—C7—C8—C9176.8 (3)
C9—O3—C1—C2−154.9 (3)O4—C7—C8—C100.5 (4)
C9—O3—C1—C628.5 (4)C6—C7—C8—C9−4.9 (4)
C1—O3—C9—O573.9 (3)C6—C7—C8—C10178.7 (3)
C1—O3—C9—C8−47.0 (3)C7—C8—C9—O335.4 (4)
C17—O5—C9—O366.6 (3)C7—C8—C9—O5−86.2 (3)
C17—O5—C9—C8−170.5 (2)C10—C8—C9—O3−148.0 (3)
C9—O5—C17—C18167.6 (3)C10—C8—C9—O590.4 (3)
C11—N1—C10—C8175.7 (3)C7—C8—C10—N1−3.0 (5)
C10—N1—C11—C12156.4 (3)C9—C8—C10—N1−179.4 (3)
C10—N1—C11—C16−26.2 (4)N1—C11—C12—C13178.2 (3)
O3—C1—C2—C3−179.0 (3)C16—C11—C12—C130.8 (5)
C6—C1—C2—C3−2.3 (5)N1—C11—C16—C15−178.3 (3)
O3—C1—C6—C5179.6 (3)C12—C11—C16—C15−1.0 (5)
O3—C1—C6—C74.4 (4)C11—C12—C13—C140.3 (5)
C2—C1—C6—C53.1 (4)C12—C13—C14—S1179.0 (2)
C2—C1—C6—C7−172.2 (3)C12—C13—C14—C15−1.2 (5)
C1—C2—C3—C4−0.6 (5)S1—C14—C15—C16−179.2 (2)
C2—C3—C4—C52.6 (5)C13—C14—C15—C161.0 (5)
C3—C4—C5—C6−1.7 (5)C14—C15—C16—C110.1 (5)
C4—C5—C6—C1−1.1 (4)
D—H···AD—HH···AD···AD—H···A
N1—H1···O40.862.042.696 (3)132
N2—H21···O6v0.91 (3)1.94 (3)2.838 (4)169 (3)
N2—H22···O2ii0.85 (3)2.22 (3)3.027 (3)159 (3)
O6—H61···O50.90 (4)2.10 (4)2.999 (3)176.7 (16)
O6—H62···O4iv0.92 (3)1.90 (3)2.784 (3)161 (3)
C2—H2···O2iii0.932.423.300 (4)157
C9—H9···O1vi1.04 (3)2.54 (3)3.472 (3)149 (2)
C13—H13···O2ii0.932.543.418 (3)158
C15—H15···O10.932.502.884 (3)105
C16—H16···Cg1i0.932.953.565 (3)125
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O40.862.042.696 (3)132
N2—H21⋯O6i0.91 (3)1.94 (3)2.838 (4)169 (3)
N2—H22⋯O2ii0.85 (3)2.22 (3)3.027 (3)159 (3)
O6—H61⋯O50.90 (4)2.10 (4)2.999 (3)176.7 (16)
O6—H62⋯O4iii0.92 (3)1.90 (3)2.784 (3)161 (3)
C2—H2⋯O2iv0.932.423.300 (4)157
C9—H9⋯O1v1.04 (3)2.54 (3)3.472 (3)149 (2)
C13—H13⋯O2ii0.932.543.418 (3)158
C15—H15⋯O10.932.502.884 (3)105
C16—H16⋯Cg1vi0.932.953.565 (3)125

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the C1–C6 ring.

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  4-[(E)-(5-Chloro-2-hydroxy-benzyl-idene)amino]benzene-sulfonamide.

Authors:  Zahid H Chohan; Hazoor A Shad; M Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-10

3.  4-{2-[(5-Chloro-2-hydroxy-benzyl-idene)amino]eth-yl}benzene-sulfonamide.

Authors:  Zahid H Chohan; Hazoor A Shad; M Nawaz Tahir; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-03-20

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  2 in total

1.  3-(6-Bromo-4-oxo-4H-chromen-3-yl)-3,4-dihydro-2H-1,2,4-benzothia-diazine-1,1-dione.

Authors:  Mariya Al-Rashida; Saeed Ahmad Nagra; Islam Ullah Khan; George Kostakis; Ghulam Abbas
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-06

2.  3-(6-Fluoro-4-oxo-4H-chromen-3-yl)-3,4-dihydro-2H-1,2,4-benzothia-diazine-1,1-dione.

Authors:  Mariya Al-Rashida; Saeed Ahmad Nagra; Islam Ullah Khan; George Kostakis; Ghulam Abbas
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-02
  2 in total

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