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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1797.
Published online 2010 June 26. doi:  10.1107/S1600536810024219
PMCID: PMC3006968

1,5-Dimethyl-3-propargyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Abstract

The asymmetric unit of the title compound, C14H14N2O2, comprises two independent mol­ecules, which slightly differ in the orientation of the propargyl chain. In both molecules, the diazepine ring adopts a boat conformation with the propargyl-bearing C atom as the prow and the C atoms at the ring junction as the stern. The carbonyl O atom of one independent mol­ecule is hydrogen bonded to the acetyl­enic H atom of the other independent mol­ecule. In the crystal, symmetry-related mol­ecules are linked together by C—H(...)O hydrogen bonds, forming a ribbon-like structure along the c axis.

Related literature

For a related structure, see: Jabli et al. (2009 [triangle]).

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Object name is e-66-o1797-scheme1.jpg

Experimental

Crystal data

  • C14H14N2O2
  • M r = 242.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1797-efi1.jpg
  • a = 16.0768 (3) Å
  • b = 17.1087 (3) Å
  • c = 8.9530 (2) Å
  • β = 93.701 (1)°
  • V = 2457.42 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.40 × 0.30 × 0.05 mm

Data collection

  • Bruker X8 APEXII area-detector diffractometer
  • 21953 measured reflections
  • 3580 independent reflections
  • 2637 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.105
  • S = 1.06
  • 3580 reflections
  • 337 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024219/ci5110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024219/ci5110Isup2.hkl

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

Acknowledgments

The authors thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We recently reported the crystal stucture of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione, a compound readily synthesized by reacting the disubstituted 1,5-benzodiazepine-2,4-dione with propargyl bromide (Jabli et al., 2009). The background to the study of such compounds is given in other reports. Replacing the benzyl unit by a methyl unit in the present study gives a compoound having a diazepine ring system (Scheme I, Fig. 1). This ring adopts a boat conformation (with the propargyl-bearing C atom as the prow and the fused-ring C atoms as the stern). There are two independent molecules; the acetylenic H-atom of one molecule forms a hydrogen to the carbonyl O-atom of the other independent molecule.

Experimental

To a solution of potassium t-butoxide (0.42 g, 3.6 mmol) in DMF (15 ml) was added 1,5-dimethyl-1,5-benzodiazepine-2,4-dione (0.50 g, 2.4 mmol) and propargyl bromide (0.26 ml, 2.87 mmol). Stirring was continued for 24 h. The reaction was monitored by thin layer chromatography. On completion of the reaction, the mixture was filtered; crystals were obtained when the solvent was allowed to evaporate.

Refinement

The acetylenic H atoms were located in a difference Fourier map and were refined with C–H distances restrained to 0.93 (1) Å; their Uiso parameters were freely refined. The remaining H atoms were placed in calculated positions (C–H = 0.93–0.98 Å) and were included in the refinement in the riding-model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). In the absence of significant anomalous scattering effects, 3266 Friedel pairs were averaged.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C14H14N2O2 at the 50% probability level shown as a hydrogen-bonded dimer; H atoms are drawn as spheres of arbitrary radius. The dashed line denotes a hydrogen bond.

Crystal data

C14H14N2O2F(000) = 1024
Mr = 242.27Dx = 1.310 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 5448 reflections
a = 16.0768 (3) Åθ = 2.5–29.4°
b = 17.1087 (3) ŵ = 0.09 mm1
c = 8.9530 (2) ÅT = 293 K
β = 93.701 (1)°Plate, colourless
V = 2457.42 (8) Å30.40 × 0.30 × 0.05 mm
Z = 8

Data collection

Bruker X8 APEXII area-detector diffractometer2637 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
graphiteθmax = 30.0°, θmin = 2.8°
[var phi] and ω scansh = −22→22
21953 measured reflectionsk = −24→23
3580 independent reflectionsl = −12→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0514P)2 + 0.5357P] where P = (Fo2 + 2Fc2)/3
3580 reflections(Δ/σ)max = 0.001
337 parametersΔρmax = 0.22 e Å3
4 restraintsΔρmin = −0.19 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.50007 (11)0.33109 (11)0.5000 (2)0.0339 (4)
O20.34014 (11)0.41769 (12)0.21819 (19)0.0332 (4)
O30.99978 (11)0.63153 (11)0.9419 (2)0.0363 (4)
O40.78408 (12)0.58439 (13)0.74162 (19)0.0380 (5)
N10.39120 (12)0.33841 (12)0.6473 (2)0.0268 (4)
N20.26570 (12)0.39080 (12)0.4189 (2)0.0253 (4)
N30.91197 (13)0.68624 (13)1.1007 (2)0.0293 (5)
N40.75177 (12)0.65404 (14)0.9454 (2)0.0298 (5)
C10.31443 (15)0.37280 (14)0.6847 (3)0.0251 (5)
C20.29827 (17)0.38043 (16)0.8365 (3)0.0318 (6)
H20.33930.36700.90990.038*
C30.22235 (19)0.40758 (17)0.8778 (3)0.0382 (6)
H30.21240.41210.97860.046*
C40.16095 (18)0.42805 (17)0.7692 (3)0.0384 (6)
H40.10910.44490.79690.046*
C50.17692 (16)0.42341 (15)0.6190 (3)0.0308 (5)
H50.13590.43850.54670.037*
C60.25334 (15)0.39661 (13)0.5746 (3)0.0240 (5)
C70.33523 (15)0.41709 (14)0.3543 (3)0.0242 (5)
C80.40776 (14)0.44186 (14)0.4628 (2)0.0232 (5)
H80.38820.47820.53750.028*
C90.43852 (14)0.36629 (14)0.5383 (3)0.0250 (5)
C100.19504 (16)0.36807 (17)0.3156 (3)0.0329 (6)
H10A0.21410.33340.24080.049*
H10B0.17110.41390.26820.049*
H10C0.15370.34210.37040.049*
C110.47672 (15)0.48013 (16)0.3774 (3)0.0295 (5)
H11A0.49540.44340.30400.035*
H11B0.45400.52550.32390.035*
C120.54896 (16)0.50462 (16)0.4769 (3)0.0324 (5)
C130.60798 (19)0.5229 (2)0.5539 (4)0.0446 (7)
H130.6549 (15)0.537 (2)0.614 (4)0.062 (11)*
C140.42070 (18)0.26755 (16)0.7274 (3)0.0373 (6)
H14A0.43250.22770.65630.056*
H14B0.37840.24930.78980.056*
H14C0.47040.27940.78840.056*
C150.83776 (15)0.68259 (15)1.1784 (3)0.0279 (5)
C160.84147 (18)0.69589 (16)1.3331 (3)0.0343 (6)
H160.89190.70951.38290.041*
C170.7709 (2)0.68902 (17)1.4124 (3)0.0404 (7)
H170.77450.69681.51540.049*
C180.6949 (2)0.67062 (18)1.3391 (3)0.0429 (7)
H180.64770.66581.39320.052*
C190.68919 (17)0.65948 (16)1.1858 (3)0.0357 (6)
H190.63780.64811.13690.043*
C200.75997 (16)0.66527 (14)1.1039 (3)0.0278 (5)
C210.79742 (15)0.60039 (16)0.8740 (3)0.0281 (5)
C220.87014 (15)0.56424 (15)0.9697 (3)0.0274 (5)
H220.84970.54531.06400.033*
C230.93407 (15)0.62914 (15)1.0034 (3)0.0272 (5)
C240.67961 (17)0.68895 (18)0.8601 (3)0.0386 (6)
H24A0.69570.70490.76340.058*
H24B0.66050.73360.91310.058*
H24C0.63560.65110.84840.058*
C250.90761 (17)0.49596 (16)0.8873 (3)0.0330 (6)
H25A0.86310.46210.84770.040*
H25B0.93650.51590.80340.040*
C260.96610 (17)0.45014 (16)0.9847 (3)0.0326 (6)
C271.01106 (19)0.41189 (19)1.0637 (4)0.0445 (7)
H271.043 (2)0.3804 (19)1.130 (4)0.070 (12)*
C280.97458 (18)0.74656 (18)1.1443 (4)0.0426 (7)
H28A1.00950.75561.06300.064*
H28B1.00820.72911.23050.064*
H28C0.94680.79421.16790.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0256 (9)0.0397 (10)0.0365 (11)0.0051 (8)0.0020 (7)−0.0001 (8)
O20.0345 (9)0.0472 (11)0.0175 (9)−0.0022 (8)−0.0014 (7)0.0014 (8)
O30.0284 (10)0.0455 (11)0.0350 (11)−0.0010 (8)0.0007 (8)−0.0021 (9)
O40.0363 (10)0.0558 (13)0.0210 (10)−0.0022 (9)−0.0054 (8)−0.0026 (8)
N10.0276 (10)0.0311 (10)0.0210 (10)0.0018 (8)−0.0029 (8)0.0052 (9)
N20.0234 (10)0.0323 (11)0.0197 (10)−0.0023 (8)−0.0022 (8)−0.0003 (8)
N30.0267 (10)0.0350 (12)0.0254 (11)−0.0037 (8)−0.0038 (8)−0.0050 (9)
N40.0256 (10)0.0398 (12)0.0233 (11)−0.0010 (8)−0.0030 (8)0.0021 (9)
C10.0275 (12)0.0277 (12)0.0202 (11)−0.0040 (9)0.0019 (9)0.0009 (10)
C20.0372 (13)0.0376 (14)0.0204 (12)−0.0069 (11)0.0008 (10)0.0013 (10)
C30.0507 (16)0.0403 (15)0.0249 (13)−0.0065 (12)0.0139 (12)−0.0015 (12)
C40.0376 (15)0.0383 (15)0.0411 (16)−0.0005 (12)0.0161 (12)−0.0007 (13)
C50.0272 (12)0.0342 (13)0.0312 (13)−0.0017 (10)0.0034 (10)0.0002 (11)
C60.0256 (11)0.0261 (11)0.0202 (11)−0.0039 (9)0.0015 (9)0.0003 (9)
C70.0244 (11)0.0288 (12)0.0194 (11)0.0038 (9)−0.0003 (8)0.0019 (9)
C80.0243 (11)0.0293 (12)0.0162 (10)−0.0010 (9)0.0022 (8)−0.0013 (9)
C90.0230 (11)0.0309 (12)0.0202 (11)−0.0016 (9)−0.0056 (9)−0.0008 (9)
C100.0276 (13)0.0400 (15)0.0295 (14)−0.0048 (11)−0.0102 (10)−0.0004 (11)
C110.0279 (12)0.0380 (14)0.0227 (12)−0.0040 (10)0.0017 (9)0.0037 (10)
C120.0308 (13)0.0374 (13)0.0296 (13)−0.0036 (11)0.0060 (11)0.0054 (11)
C130.0379 (15)0.0542 (19)0.0412 (17)−0.0145 (14)−0.0016 (13)0.0030 (14)
C140.0414 (15)0.0365 (15)0.0335 (14)0.0051 (12)−0.0019 (11)0.0121 (12)
C150.0316 (13)0.0288 (13)0.0231 (12)0.0016 (10)−0.0010 (10)−0.0013 (10)
C160.0438 (15)0.0345 (14)0.0238 (13)0.0031 (11)−0.0047 (11)−0.0013 (11)
C170.0598 (18)0.0374 (15)0.0244 (13)0.0026 (13)0.0047 (13)0.0006 (12)
C180.0497 (17)0.0412 (17)0.0401 (17)−0.0037 (13)0.0199 (14)0.0010 (13)
C190.0337 (14)0.0384 (15)0.0356 (15)−0.0055 (11)0.0056 (12)−0.0004 (12)
C200.0317 (12)0.0284 (12)0.0233 (12)−0.0028 (10)0.0011 (10)0.0004 (10)
C210.0254 (11)0.0374 (13)0.0210 (12)−0.0078 (10)−0.0016 (9)0.0018 (10)
C220.0312 (12)0.0335 (13)0.0170 (11)−0.0003 (10)−0.0016 (9)0.0007 (10)
C230.0250 (11)0.0353 (13)0.0202 (12)0.0019 (9)−0.0056 (9)0.0023 (10)
C240.0291 (13)0.0506 (17)0.0351 (15)0.0009 (12)−0.0066 (11)0.0030 (13)
C250.0422 (14)0.0367 (14)0.0197 (12)−0.0012 (11)−0.0007 (11)−0.0029 (10)
C260.0341 (13)0.0362 (14)0.0279 (13)−0.0034 (11)0.0051 (10)−0.0044 (11)
C270.0344 (15)0.0495 (18)0.0488 (19)−0.0012 (13)−0.0036 (13)0.0078 (14)
C280.0351 (14)0.0497 (17)0.0423 (17)−0.0121 (13)−0.0030 (12)−0.0113 (14)

Geometric parameters (Å, °)

O1—C91.226 (3)C11—C121.478 (4)
O2—C71.226 (3)C11—H11A0.97
O3—C231.223 (3)C11—H11B0.97
O4—C211.222 (3)C12—C131.179 (4)
N1—C91.361 (3)C13—H130.93 (3)
N1—C11.427 (3)C14—H14A0.96
N1—C141.472 (3)C14—H14B0.96
N2—C71.367 (3)C14—H14C0.96
N2—C61.424 (3)C15—C161.401 (3)
N2—C101.470 (3)C15—C201.411 (3)
N3—C231.371 (3)C16—C171.381 (4)
N3—C151.421 (3)C16—H160.93
N3—C281.476 (3)C17—C181.385 (4)
N4—C211.360 (3)C17—H170.93
N4—C201.430 (3)C18—C191.383 (4)
N4—C241.473 (3)C18—H180.93
C1—C61.406 (3)C19—C201.397 (4)
C1—C21.406 (4)C19—H190.93
C2—C31.379 (4)C21—C221.535 (3)
C2—H20.93C22—C251.526 (4)
C3—C41.385 (4)C22—C231.530 (3)
C3—H30.93C22—H220.98
C4—C51.388 (4)C24—H24A0.96
C4—H40.93C24—H24B0.96
C5—C61.393 (4)C24—H24C0.96
C5—H50.93C25—C261.468 (4)
C7—C81.528 (3)C25—H25A0.97
C8—C91.526 (3)C25—H25B0.97
C8—C111.534 (3)C26—C271.177 (4)
C8—H80.98C27—H270.93 (3)
C10—H10A0.96C28—H28A0.96
C10—H10B0.96C28—H28B0.96
C10—H10C0.96C28—H28C0.96
C9—N1—C1123.77 (19)N1—C14—H14A109.5
C9—N1—C14117.4 (2)N1—C14—H14B109.5
C1—N1—C14118.8 (2)H14A—C14—H14B109.5
C7—N2—C6124.09 (19)N1—C14—H14C109.5
C7—N2—C10116.2 (2)H14A—C14—H14C109.5
C6—N2—C10118.88 (19)H14B—C14—H14C109.5
C23—N3—C15122.7 (2)C16—C15—C20118.8 (2)
C23—N3—C28117.8 (2)C16—C15—N3119.6 (2)
C15—N3—C28118.7 (2)C20—C15—N3121.6 (2)
C21—N4—C20122.6 (2)C17—C16—C15120.7 (2)
C21—N4—C24117.4 (2)C17—C16—H16119.7
C20—N4—C24118.6 (2)C15—C16—H16119.7
C6—C1—C2119.1 (2)C16—C17—C18120.3 (3)
C6—C1—N1122.0 (2)C16—C17—H17119.9
C2—C1—N1118.8 (2)C18—C17—H17119.9
C3—C2—C1120.8 (2)C17—C18—C19120.1 (3)
C3—C2—H2119.6C17—C18—H18120.0
C1—C2—H2119.6C19—C18—H18120.0
C2—C3—C4120.0 (3)C18—C19—C20120.5 (3)
C2—C3—H3120.0C18—C19—H19119.8
C4—C3—H3120.0C20—C19—H19119.8
C3—C4—C5119.8 (3)C19—C20—C15119.6 (2)
C3—C4—H4120.1C19—C20—N4119.1 (2)
C5—C4—H4120.1C15—C20—N4121.3 (2)
C4—C5—C6121.1 (3)O4—C21—N4122.7 (2)
C4—C5—H5119.4O4—C21—C22122.1 (2)
C6—C5—H5119.4N4—C21—C22115.1 (2)
C5—C6—C1119.0 (2)C25—C22—C23111.7 (2)
C5—C6—N2118.9 (2)C25—C22—C21110.40 (19)
C1—C6—N2122.1 (2)C23—C22—C21107.2 (2)
O2—C7—N2122.0 (2)C25—C22—H22109.2
O2—C7—C8122.3 (2)C23—C22—H22109.2
N2—C7—C8115.7 (2)C21—C22—H22109.2
C9—C8—C7105.00 (19)O3—C23—N3121.9 (2)
C9—C8—C11111.0 (2)O3—C23—C22121.6 (2)
C7—C8—C11110.36 (19)N3—C23—C22116.4 (2)
C9—C8—H8110.1N4—C24—H24A109.5
C7—C8—H8110.1N4—C24—H24B109.5
C11—C8—H8110.1H24A—C24—H24B109.5
O1—C9—N1121.8 (2)N4—C24—H24C109.5
O1—C9—C8122.4 (2)H24A—C24—H24C109.5
N1—C9—C8115.7 (2)H24B—C24—H24C109.5
N2—C10—H10A109.5C26—C25—C22112.3 (2)
N2—C10—H10B109.5C26—C25—H25A109.1
H10A—C10—H10B109.5C22—C25—H25A109.1
N2—C10—H10C109.5C26—C25—H25B109.1
H10A—C10—H10C109.5C22—C25—H25B109.1
H10B—C10—H10C109.5H25A—C25—H25B107.9
C12—C11—C8112.7 (2)C27—C26—C25178.0 (3)
C12—C11—H11A109.1C26—C27—H27176 (3)
C8—C11—H11A109.1N3—C28—H28A109.5
C12—C11—H11B109.1N3—C28—H28B109.5
C8—C11—H11B109.1H28A—C28—H28B109.5
H11A—C11—H11B107.8N3—C28—H28C109.5
C13—C12—C11178.1 (3)H28A—C28—H28C109.5
C12—C13—H13180 (3)H28B—C28—H28C109.5
C9—N1—C1—C644.7 (3)C23—N3—C15—C16131.1 (3)
C14—N1—C1—C6−133.7 (3)C28—N3—C15—C16−38.5 (3)
C9—N1—C1—C2−137.7 (2)C23—N3—C15—C20−48.5 (3)
C14—N1—C1—C243.9 (3)C28—N3—C15—C20142.0 (3)
C6—C1—C2—C32.9 (4)C20—C15—C16—C172.7 (4)
N1—C1—C2—C3−174.9 (2)N3—C15—C16—C17−176.9 (3)
C1—C2—C3—C4−0.3 (4)C15—C16—C17—C18−1.5 (4)
C2—C3—C4—C5−1.9 (4)C16—C17—C18—C19−0.4 (4)
C3—C4—C5—C61.6 (4)C17—C18—C19—C201.1 (4)
C4—C5—C6—C11.0 (4)C18—C19—C20—C150.0 (4)
C4—C5—C6—N2178.2 (2)C18—C19—C20—N4−179.5 (3)
C2—C1—C6—C5−3.2 (3)C16—C15—C20—C19−1.9 (4)
N1—C1—C6—C5174.4 (2)N3—C15—C20—C19177.7 (2)
C2—C1—C6—N2179.8 (2)C16—C15—C20—N4177.6 (2)
N1—C1—C6—N2−2.6 (3)N3—C15—C20—N4−2.8 (4)
C7—N2—C6—C5133.8 (2)C21—N4—C20—C19−124.8 (3)
C10—N2—C6—C5−35.1 (3)C24—N4—C20—C1941.7 (3)
C7—N2—C6—C1−49.2 (3)C21—N4—C20—C1555.7 (3)
C10—N2—C6—C1141.9 (2)C24—N4—C20—C15−137.8 (2)
C6—N2—C7—O2−173.0 (2)C20—N4—C21—O4171.5 (2)
C10—N2—C7—O2−3.8 (3)C24—N4—C21—O44.8 (4)
C6—N2—C7—C89.9 (3)C20—N4—C21—C22−11.6 (3)
C10—N2—C7—C8179.0 (2)C24—N4—C21—C22−178.2 (2)
O2—C7—C8—C9−109.3 (3)O4—C21—C22—C25−12.3 (3)
N2—C7—C8—C967.9 (3)N4—C21—C22—C25170.7 (2)
O2—C7—C8—C1110.4 (3)O4—C21—C22—C23109.5 (3)
N2—C7—C8—C11−172.4 (2)N4—C21—C22—C23−67.4 (3)
C1—N1—C9—O1−173.1 (2)C15—N3—C23—O3−177.0 (2)
C14—N1—C9—O15.3 (3)C28—N3—C23—O3−7.4 (4)
C1—N1—C9—C84.2 (3)C15—N3—C23—C226.0 (3)
C14—N1—C9—C8−177.4 (2)C28—N3—C23—C22175.6 (2)
C7—C8—C9—O1100.1 (2)C25—C22—C23—O314.7 (3)
C11—C8—C9—O1−19.1 (3)C21—C22—C23—O3−106.3 (3)
C7—C8—C9—N1−77.2 (2)C25—C22—C23—N3−168.3 (2)
C11—C8—C9—N1163.55 (19)C21—C22—C23—N370.7 (3)
C9—C8—C11—C12−63.5 (3)C23—C22—C25—C2672.0 (3)
C7—C8—C11—C12−179.5 (2)C21—C22—C25—C26−168.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···O40.93 (3)2.44 (3)3.366 (3)172 (3)
C8—H8···O2i0.982.563.536 (3)175
C19—H19···O1i0.932.493.374 (3)160

Symmetry codes: (i) x, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5110).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jabli, H., Ouazzani Chahdi, F., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o3149. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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