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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3031.
Published online 2009 November 7. doi:  10.1107/S1600536809046194
PMCID: PMC2972102

4-(4-Bromo-3-methyl-1H-pyrazol-1-yl)-6-(but-3-yn­yloxy)pyrimidine

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C12H11BrN4O. The dihedral angles between the pyrazole and pyrimidine rings are 1.28 (17) and 1.56 (17)° in the two mol­ecules. In one of the mol­ecules, the but-3-yn­yloxy side chain is disordered over two sets of sites in a 0.714 (8):0.286 (8) ratio.

Related literature

For background information on pyrimidines, see: Regiec et al. (2009 [triangle]).

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Object name is e-65-o3031-scheme1.jpg

Experimental

Crystal data

  • C12H11BrN4O
  • M r = 307.16
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3031-efi1.jpg
  • a = 7.9053 (16) Å
  • b = 10.045 (2) Å
  • c = 16.807 (3) Å
  • α = 75.34 (3)°
  • β = 77.98 (3)°
  • γ = 80.78 (3)°
  • V = 1254.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.27 mm−1
  • T = 173 K
  • 0.11 × 0.10 × 0.07 mm

Data collection

  • Rigaku Saturn724+ CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 [triangle]) T min = 0.715, T max = 0.803
  • 15373 measured reflections
  • 5693 independent reflections
  • 4988 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.106
  • S = 1.15
  • 5693 reflections
  • 344 parameters
  • 48 restraints
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.40 e Å−3

Data collection: CrystalClear (Rigaku, 2008 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046194/hb5193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046194/hb5193Isup2.hkl

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

Acknowledgments

This work was supported by the China Postdoctoral Science Foundation (No. 20070420444), the Major State Basic Research Development Program of China (No. 2010CB126106 and No. 2006CB101907) and the 863 High-Tech Key Project of China (2006AA10A203).

supplementary crystallographic information

Experimental

The title compound (0.1 g) was dissolved in the mixed solvent of ethanol and acetone (20 ml) at room temperature. Colourless blocks of (I) were obtained through slow evaporation after two weeks.

Refinement

All the hydrogen atoms were placed at their geometrical position with C—H = 0.93–0.98Å and Uiso (H) = 1.2–1.5 Uep (C).

Figures

Fig. 1.
The molecular structure of the title compound showing 30% probability displacement ellipsoids.

Crystal data

C12H11BrN4OZ = 4
Mr = 307.16F(000) = 616
Triclinic, P1Dx = 1.626 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9053 (16) ÅCell parameters from 536 reflections
b = 10.045 (2) Åθ = 2.2–27.5°
c = 16.807 (3) ŵ = 3.27 mm1
α = 75.34 (3)°T = 173 K
β = 77.98 (3)°Plate, colorless
γ = 80.78 (3)°0.11 × 0.10 × 0.07 mm
V = 1254.7 (4) Å3

Data collection

Rigaku Saturn724+ CCD diffractometer5693 independent reflections
Radiation source: sealed tube4988 reflections with I > 2σ(I)
graphiteRint = 0.038
ω scans at fixed χ = 45°θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)h = −10→10
Tmin = 0.715, Tmax = 0.803k = −13→13
15373 measured reflectionsl = −21→21

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.15w = 1/[σ2(Fo2) + (0.036P)2 + 1.1156P] where P = (Fo2 + 2Fc2)/3
5693 reflections(Δ/σ)max = 0.001
344 parametersΔρmax = 0.38 e Å3
48 restraintsΔρmin = −0.40 e Å3

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*/UeqOcc. (<1)
Br10.84764 (4)0.85935 (4)−0.01999 (2)0.04160 (12)
Br2−0.32369 (4)0.71052 (4)0.25637 (2)0.04014 (12)
O1−0.0831 (3)0.4253 (2)0.12494 (14)0.0390 (6)
N10.4057 (3)0.4528 (3)0.15609 (17)0.0313 (6)
N20.1464 (3)0.3392 (3)0.19584 (17)0.0329 (6)
N30.4330 (3)0.6484 (3)0.04879 (16)0.0275 (6)
N40.3723 (4)0.7482 (3)−0.01432 (16)0.0319 (6)
N50.0933 (3)0.3312 (3)0.46819 (17)0.0311 (6)
N60.3526 (4)0.2288 (3)0.52183 (18)0.0364 (7)
N70.0905 (3)0.5264 (3)0.36020 (15)0.0267 (5)
N80.1708 (3)0.6315 (3)0.30304 (17)0.0322 (6)
C10.3082 (4)0.3559 (3)0.2019 (2)0.0323 (7)
H1A0.35880.28980.24430.039*
C20.3293 (4)0.5457 (3)0.09735 (18)0.0262 (6)
C30.1647 (4)0.5414 (3)0.0840 (2)0.0309 (7)
H3A0.11400.60780.04180.037*
C40.0784 (4)0.4343 (3)0.1362 (2)0.0313 (7)
C50.5956 (4)0.6658 (3)0.0570 (2)0.0315 (7)
H5A0.66360.60960.09610.038*
C60.6397 (4)0.7794 (3)−0.0020 (2)0.0304 (7)
C70.4990 (4)0.8284 (3)−0.04569 (19)0.0302 (7)
C80.4879 (5)0.9490 (4)−0.1191 (2)0.0400 (8)
H8A0.37420.9589−0.13590.060*
H8B0.58020.9331−0.16570.060*
H8C0.50201.0337−0.10350.060*
C9−0.1643 (5)0.3004 (4)0.1696 (2)0.0388 (8)
H9A−0.07460.21920.17220.047*
H9B−0.25160.28680.13870.047*
C10−0.2516 (5)0.3097 (4)0.2568 (2)0.0387 (8)
H10A−0.16680.32820.28740.046*
H10B−0.34760.38630.25480.046*
C11−0.3206 (4)0.1772 (4)0.2997 (2)0.0404 (8)
C12−0.3688 (5)0.0678 (4)0.3306 (2)0.0461 (9)
H12−0.4077−0.02050.35550.055*
C130.1847 (4)0.2382 (3)0.5180 (2)0.0324 (7)
H13A0.12210.16830.55630.039*
C140.1859 (4)0.4271 (3)0.41388 (19)0.0259 (6)
C150.3608 (4)0.4307 (3)0.4096 (2)0.0319 (7)
H15A0.42440.49880.37010.038*
C160.4367 (4)0.3271 (4)0.4674 (2)0.0384 (8)
C17−0.0815 (4)0.5332 (3)0.35647 (19)0.0285 (7)
H17A−0.16290.47260.39000.034*
C18−0.1110 (4)0.6466 (3)0.2937 (2)0.0294 (7)
C190.0468 (4)0.7055 (3)0.2624 (2)0.0315 (7)
C200.0820 (5)0.8313 (4)0.1948 (2)0.0460 (9)
H20A0.20430.84640.18730.069*
H20B0.00710.91190.21010.069*
H20C0.05780.81830.14260.069*
O20.6027 (4)0.3390 (4)0.4735 (3)0.0316 (10)0.714 (8)
C210.6792 (6)0.2448 (5)0.5416 (3)0.0337 (13)0.714 (8)
H21A0.59030.23190.59310.040*0.714 (8)
H21B0.77580.28610.55210.040*0.714 (8)
C220.7475 (7)0.1058 (6)0.5210 (3)0.0374 (13)0.714 (8)
H22A0.65280.06600.50780.045*0.714 (8)
H22B0.84170.11730.47160.045*0.714 (8)
C230.8143 (6)0.0124 (5)0.5927 (3)0.0347 (13)0.714 (8)
O2'0.6200 (12)0.3001 (11)0.4464 (6)0.027 (2)*0.286 (8)
C21'0.7129 (14)0.1783 (13)0.4919 (7)0.027 (3)*0.286 (8)
H21C0.83330.16490.46110.032*0.286 (8)
H21D0.65540.09600.49530.032*0.286 (8)
C22'0.7188 (17)0.1897 (14)0.5783 (9)0.035 (3)*0.286 (8)
H22C0.78830.26530.57500.042*0.286 (8)
H22D0.59930.21350.60700.042*0.286 (8)
C23'0.7965 (16)0.0586 (14)0.6274 (9)0.034 (3)*0.286 (8)
C240.8639 (5)−0.0575 (4)0.6544 (3)0.0473 (10)
H240.9032−0.11290.70340.057*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.03268 (19)0.0426 (2)0.0462 (2)−0.01365 (15)−0.00338 (15)−0.00121 (16)
Br20.03508 (19)0.0429 (2)0.0398 (2)0.00172 (15)−0.01630 (15)−0.00052 (15)
O10.0290 (12)0.0405 (14)0.0411 (14)−0.0147 (10)−0.0134 (10)0.0147 (11)
N10.0258 (13)0.0306 (14)0.0333 (15)−0.0030 (11)−0.0065 (11)0.0011 (11)
N20.0297 (14)0.0314 (14)0.0331 (15)−0.0035 (11)−0.0099 (11)0.0041 (11)
N30.0273 (13)0.0274 (13)0.0259 (13)−0.0075 (10)−0.0050 (10)0.0006 (10)
N40.0358 (15)0.0311 (14)0.0279 (14)−0.0059 (11)−0.0121 (12)0.0015 (11)
N50.0278 (14)0.0290 (14)0.0337 (15)−0.0083 (11)−0.0055 (11)0.0011 (11)
N60.0294 (14)0.0332 (15)0.0392 (16)−0.0066 (12)−0.0089 (12)0.0093 (12)
N70.0238 (13)0.0253 (13)0.0276 (14)−0.0041 (10)−0.0023 (10)−0.0009 (10)
N80.0309 (14)0.0280 (14)0.0327 (15)−0.0074 (11)−0.0045 (11)0.0036 (11)
C10.0286 (16)0.0314 (17)0.0326 (18)−0.0019 (13)−0.0088 (13)0.0021 (13)
C20.0248 (15)0.0282 (16)0.0232 (15)−0.0035 (12)−0.0028 (12)−0.0021 (12)
C30.0335 (17)0.0287 (16)0.0284 (17)−0.0009 (13)−0.0109 (13)0.0002 (13)
C40.0291 (16)0.0324 (17)0.0311 (17)−0.0017 (13)−0.0095 (13)−0.0028 (13)
C50.0304 (17)0.0311 (17)0.0315 (17)−0.0043 (13)−0.0086 (13)−0.0013 (13)
C60.0287 (16)0.0308 (17)0.0314 (17)−0.0035 (13)−0.0027 (13)−0.0086 (13)
C70.0329 (17)0.0310 (17)0.0257 (16)−0.0076 (13)−0.0017 (13)−0.0049 (13)
C80.046 (2)0.0354 (19)0.0338 (19)−0.0089 (16)−0.0081 (16)0.0040 (15)
C90.0338 (18)0.044 (2)0.038 (2)−0.0123 (15)−0.0103 (15)−0.0008 (16)
C100.0334 (18)0.0395 (19)0.043 (2)−0.0052 (15)−0.0098 (15)−0.0055 (16)
C110.0293 (17)0.048 (2)0.041 (2)−0.0049 (15)−0.0144 (15)0.0006 (17)
C120.047 (2)0.045 (2)0.042 (2)−0.0207 (18)−0.0114 (17)0.0103 (17)
C130.0255 (16)0.0324 (17)0.0359 (18)−0.0082 (13)−0.0044 (13)0.0005 (14)
C140.0255 (15)0.0239 (15)0.0274 (16)−0.0044 (12)−0.0049 (12)−0.0028 (12)
C150.0282 (16)0.0279 (16)0.0352 (18)−0.0050 (13)−0.0066 (13)0.0027 (13)
C160.0284 (17)0.0383 (19)0.042 (2)−0.0063 (14)−0.0097 (15)0.0064 (15)
C170.0261 (15)0.0295 (16)0.0295 (16)−0.0026 (12)−0.0064 (13)−0.0047 (13)
C180.0290 (16)0.0295 (16)0.0298 (16)0.0007 (13)−0.0102 (13)−0.0055 (13)
C190.0324 (17)0.0306 (17)0.0295 (17)−0.0039 (13)−0.0072 (13)−0.0014 (13)
C200.052 (2)0.036 (2)0.045 (2)−0.0116 (17)−0.0146 (18)0.0088 (16)
O20.0213 (16)0.029 (2)0.040 (2)−0.0071 (13)−0.0081 (15)0.0042 (17)
C210.027 (2)0.037 (3)0.037 (3)−0.0047 (19)−0.011 (2)−0.003 (2)
C220.036 (3)0.037 (3)0.035 (3)−0.002 (2)−0.006 (2)−0.003 (2)
C230.026 (2)0.034 (3)0.040 (3)−0.0020 (18)−0.003 (2)−0.003 (2)
C240.0302 (18)0.051 (2)0.049 (2)−0.0037 (16)−0.0071 (16)0.0095 (18)

Geometric parameters (Å, °)

Br1—C61.879 (3)C10—H10A0.9900
Br2—C181.877 (3)C10—H10B0.9900
O1—C41.349 (4)C11—C121.177 (5)
O1—C91.460 (4)C12—H120.9500
N1—C11.322 (4)C13—H13A0.9500
N1—C21.346 (4)C14—C151.375 (4)
N2—C41.335 (4)C15—C161.385 (4)
N2—C11.344 (4)C15—H15A0.9500
N3—C51.363 (4)C16—O21.363 (4)
N3—N41.371 (3)C16—O2'1.417 (10)
N3—C21.404 (4)C17—C181.369 (4)
N4—C71.324 (4)C17—H17A0.9500
N5—C131.318 (4)C18—C191.410 (4)
N5—C141.341 (4)C19—C201.490 (4)
N6—C161.324 (4)C20—H20A0.9800
N6—C131.330 (4)C20—H20B0.9800
N7—C171.364 (4)C20—H20C0.9800
N7—N81.374 (3)O2—C211.458 (6)
N7—C141.402 (4)C21—C221.512 (8)
N8—C191.329 (4)C21—H21A0.9900
C1—H1A0.9500C21—H21B0.9900
C2—C31.374 (4)C22—C231.464 (7)
C3—C41.379 (4)C22—H22A0.9900
C3—H3A0.9500C22—H22B0.9900
C5—C61.348 (4)C23—C241.198 (6)
C5—H5A0.9500O2'—C21'1.448 (16)
C6—C71.415 (4)C21'—C22'1.496 (18)
C7—C81.500 (4)C21'—H21C0.9900
C8—H8A0.9800C21'—H21D0.9900
C8—H8B0.9800C22'—C23'1.481 (19)
C8—H8C0.9800C22'—H22C0.9900
C9—C101.503 (5)C22'—H22D0.9900
C9—H9A0.9900C23'—C241.218 (13)
C9—H9B0.9900C24—H240.9500
C10—C111.474 (5)
C4—O1—C9118.1 (2)N5—C14—N7114.8 (3)
C1—N1—C2114.5 (3)C15—C14—N7121.2 (3)
C4—N2—C1114.5 (3)C14—C15—C16114.6 (3)
C5—N3—N4112.1 (2)C14—C15—H15A122.7
C5—N3—C2127.4 (3)C16—C15—H15A122.7
N4—N3—C2120.5 (2)N6—C16—O2119.1 (3)
C7—N4—N3104.9 (2)N6—C16—C15124.1 (3)
C13—N5—C14114.2 (3)O2—C16—C15116.3 (3)
C16—N6—C13114.3 (3)N6—C16—O2'117.6 (5)
C17—N7—N8112.7 (2)O2—C16—O2'27.1 (3)
C17—N7—C14127.3 (3)C15—C16—O2'114.6 (5)
N8—N7—C14120.0 (2)N7—C17—C18104.8 (3)
C19—N8—N7104.9 (2)N7—C17—H17A127.6
N1—C1—N2128.1 (3)C18—C17—H17A127.6
N1—C1—H1A116.0C17—C18—C19107.6 (3)
N2—C1—H1A116.0C17—C18—Br2125.8 (2)
N1—C2—C3123.8 (3)C19—C18—Br2126.6 (2)
N1—C2—N3114.4 (3)N8—C19—C18110.0 (3)
C3—C2—N3121.8 (3)N8—C19—C20121.6 (3)
C2—C3—C4115.4 (3)C18—C19—C20128.5 (3)
C2—C3—H3A122.3C19—C20—H20A109.5
C4—C3—H3A122.3C19—C20—H20B109.5
N2—C4—O1118.8 (3)H20A—C20—H20B109.5
N2—C4—C3123.7 (3)C19—C20—H20C109.5
O1—C4—C3117.5 (3)H20A—C20—H20C109.5
C6—C5—N3105.7 (3)H20B—C20—H20C109.5
C6—C5—H5A127.2C16—O2—C21118.4 (3)
N3—C5—H5A127.2O2—C21—C22111.2 (5)
C5—C6—C7107.3 (3)O2—C21—H21A109.4
C5—C6—Br1125.9 (3)C22—C21—H21A109.4
C7—C6—Br1126.8 (2)O2—C21—H21B109.4
N4—C7—C6110.0 (3)C22—C21—H21B109.4
N4—C7—C8122.3 (3)H21A—C21—H21B108.0
C6—C7—C8127.7 (3)C23—C22—C21109.4 (5)
C7—C8—H8A109.5C23—C22—H22A109.8
C7—C8—H8B109.5C21—C22—H22A109.8
H8A—C8—H8B109.5C23—C22—H22B109.8
C7—C8—H8C109.5C21—C22—H22B109.8
H8A—C8—H8C109.5H22A—C22—H22B108.2
H8B—C8—H8C109.5C24—C23—C22175.5 (6)
O1—C9—C10111.5 (3)C16—O2'—C21'120.6 (8)
O1—C9—H9A109.3O2'—C21'—C22'112.0 (12)
C10—C9—H9A109.3O2'—C21'—H21C109.2
O1—C9—H9B109.3C22'—C21'—H21C109.2
C10—C9—H9B109.3O2'—C21'—H21D109.2
H9A—C9—H9B108.0C22'—C21'—H21D109.2
C11—C10—C9108.5 (3)H21C—C21'—H21D107.9
C11—C10—H10A110.0C23'—C22'—C21'111.4 (12)
C9—C10—H10A110.0C23'—C22'—H22C109.3
C11—C10—H10B110.0C21'—C22'—H22C109.3
C9—C10—H10B110.0C23'—C22'—H22D109.3
H10A—C10—H10B108.4C21'—C22'—H22D109.3
C12—C11—C10176.1 (4)H22C—C22'—H22D108.0
C11—C12—H12180.0C24—C23'—C22'168.1 (14)
N5—C13—N6128.8 (3)C23—C24—C23'39.2 (6)
N5—C13—H13A115.6C23—C24—H24180.0
N6—C13—H13A115.6C23'—C24—H24140.8
N5—C14—C15124.0 (3)
C5—N3—N4—C70.0 (4)C17—N7—C14—N5−1.6 (5)
C2—N3—N4—C7178.9 (3)N8—N7—C14—N5178.6 (3)
C17—N7—N8—C19−0.2 (4)C17—N7—C14—C15178.4 (3)
C14—N7—N8—C19179.6 (3)N8—N7—C14—C15−1.3 (4)
C2—N1—C1—N20.8 (5)N5—C14—C15—C16−0.9 (5)
C4—N2—C1—N1−0.5 (5)N7—C14—C15—C16179.1 (3)
C1—N1—C2—C3−0.8 (5)C13—N6—C16—O2171.0 (4)
C1—N1—C2—N3−180.0 (3)C13—N6—C16—C15−1.2 (6)
C5—N3—C2—N1−2.5 (5)C13—N6—C16—O2'−158.2 (6)
N4—N3—C2—N1178.8 (3)C14—C15—C16—N61.8 (6)
C5—N3—C2—C3178.3 (3)C14—C15—C16—O2−170.6 (4)
N4—N3—C2—C3−0.3 (5)C14—C15—C16—O2'159.4 (6)
N1—C2—C3—C40.6 (5)N8—N7—C17—C180.7 (4)
N3—C2—C3—C4179.7 (3)C14—N7—C17—C18−179.1 (3)
C1—N2—C4—O1179.4 (3)N7—C17—C18—C19−0.8 (4)
C1—N2—C4—C30.2 (5)N7—C17—C18—Br2179.0 (2)
C9—O1—C4—N2−9.4 (5)N7—N8—C19—C18−0.3 (4)
C9—O1—C4—C3169.8 (3)N7—N8—C19—C20179.5 (3)
C2—C3—C4—N2−0.3 (5)C17—C18—C19—N80.8 (4)
C2—C3—C4—O1−179.5 (3)Br2—C18—C19—N8−179.1 (2)
N4—N3—C5—C60.2 (4)C17—C18—C19—C20−179.0 (3)
C2—N3—C5—C6−178.5 (3)Br2—C18—C19—C201.1 (5)
N3—C5—C6—C7−0.3 (4)N6—C16—O2—C21−1.8 (7)
N3—C5—C6—Br1178.1 (2)C15—C16—O2—C21171.0 (4)
N3—N4—C7—C6−0.2 (3)O2'—C16—O2—C21−96.0 (11)
N3—N4—C7—C8177.7 (3)C16—O2—C21—C2281.1 (6)
C5—C6—C7—N40.4 (4)O2—C21—C22—C23−176.9 (4)
Br1—C6—C7—N4−178.0 (2)C21—C22—C23—C2410 (7)
C5—C6—C7—C8−177.5 (3)N6—C16—O2'—C21'−8.8 (12)
Br1—C6—C7—C84.1 (5)O2—C16—O2'—C21'91.8 (13)
C4—O1—C9—C1084.4 (4)C15—C16—O2'—C21'−168.0 (8)
O1—C9—C10—C11−176.4 (3)C16—O2'—C21'—C22'−71.7 (13)
C9—C10—C11—C1222 (6)O2'—C21'—C22'—C23'173.6 (10)
C14—N5—C13—N61.1 (5)C21'—C22'—C23'—C242(6)
C16—N6—C13—N5−0.3 (6)C22—C23—C24—C23'−10 (6)
C13—N5—C14—C15−0.4 (5)C22'—C23'—C24—C23−3(5)
C13—N5—C14—N7179.7 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5193).

References

  • Regiec, A., Mastalarz, H. & Kochel, A. (2009). Tetrahedron Lett. 50, 2624–2627.
  • Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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