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

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ISSN: 2056-9890

(9R,10R,10aR)-9-(2-Bromo­phen­yl)-10-nitro-6-phenyl-10,10a-di­hydro-9H-benzo[c]chromene-8-carbaldehyde

aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 21 September 2011; accepted 28 September 2011; online 5 October 2011)

The title compound, C26H18BrNO4, features a functionalized chromene. The cyclo­hexene ring adopts a sofa conformation and has the nitro group and the bromo­phenyl ring in an axial position. The ten atoms of the chromene moiety lie close to a common plane (r.m.s. deviation = 0.066 Å). The attached phenyl ring is twisted by 32.89 (10)° from the chromene plane. The crystal packing is stabilized by C—H⋯O inter­actions.

Related literature

For functionalized chromenes, see: Ellis & Lockhart (2007[Ellis, G. P. & Lockhart, I. M. (2007). The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones, Vol. 31, edited by G. P. Ellis, pp. 1-1196. London: Wiley-VCH.]). For the synthesis of the title compound, see: Rueping et al. (2011[Rueping, M., Dufour, J. & Maji, M. S. (2011). In preparation.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18BrNO4

  • Mr = 488.32

  • Monoclinic, P 21

  • a = 7.1583 (8) Å

  • b = 13.2036 (12) Å

  • c = 11.2510 (14) Å

  • β = 90.642 (9)°

  • V = 1063.3 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.97 mm−1

  • T = 173 K

  • 0.36 × 0.35 × 0.19 mm

Data collection
  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: multi-scan (MULABS; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.538, Tmax = 0.706

  • 6069 measured reflections

  • 3778 independent reflections

  • 3443 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.087

  • S = 1.00

  • 3778 reflections

  • 290 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.60 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1700 Friedel pairs

  • Flack parameter: −0.003 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯O15i 1.00 2.34 3.266 (4) 154
C7—H7⋯O15ii 0.95 2.55 3.487 (5) 168
C25—H25⋯O15iii 0.95 2.45 3.314 (4) 151
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) [-x, y+{\script{1\over 2}}, -z+1]; (iii) x, y, z-1.

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Functionalized chromenes are important compounds due to their biological activity. They find wide application in medicinal chemistry and have shown to display spasmolytic, diuretic, clotting, antiviral, anti-tumoral and anti-anaphylactic activity. Additionally, they can be used as pigments, photo-active materials and biodegradable agrochemicals. Furthermore, chromenes are components of numerous natural products (Ellis & Lockhart, 2007). The title compound was prepared following two new consecutive domino reactions starting from readily available propargylic alcohols, nitro-styrenes and α,β-unsaturated aldehydes.

The title compound features a functionalized chromene. The cyclohexene ring adopts a sofa conformation and has the nitro group and the bromophenyl ring in an axial position. The ten atoms of the chromene moiety lie in a common plane (r.m.s. deviation 0.066 Å). The attached phenyl ring is twisted by 32.89 (10)° from the chromene plane. The crystal packing is stabilized by C—H···O interactions.

Related literature top

For functionalized chromenes, see: Ellis & Lockhart (2007). For the synthesis of the title compound, see: Rueping et al. (2011).

Experimental top

The title compound has been synthesized as described by Rueping et al. (2011).

Refinement top

All H atoms could be located by difference Fourier synthesis. They were refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] using a riding model with C—H ranging from 0.95Å to 1.00 Å.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
(9R,10R,10aR)-9-(2-Bromophenyl)-10-nitro-6-phenyl- 10,10a-dihydro-9H-benzo[c]chromene-8-carbaldehyde top
Crystal data top
C26H18BrNO4F(000) = 496
Mr = 488.32Dx = 1.525 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5380 reflections
a = 7.1583 (8) Åθ = 3.6–25.9°
b = 13.2036 (12) ŵ = 1.97 mm1
c = 11.2510 (14) ÅT = 173 K
β = 90.642 (9)°Plate, yellow
V = 1063.3 (2) Å30.36 × 0.35 × 0.19 mm
Z = 2
Data collection top
Stoe IPDS II two-circle
diffractometer
3778 independent reflections
Radiation source: fine-focus sealed tube3443 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
h = 88
Tmin = 0.538, Tmax = 0.706k = 1616
6069 measured reflectionsl = 1113
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0608P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087(Δ/σ)max = 0.001
S = 1.00Δρmax = 0.59 e Å3
3778 reflectionsΔρmin = 0.60 e Å3
290 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.021 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1700 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.003 (8)
Crystal data top
C26H18BrNO4V = 1063.3 (2) Å3
Mr = 488.32Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.1583 (8) ŵ = 1.97 mm1
b = 13.2036 (12) ÅT = 173 K
c = 11.2510 (14) Å0.36 × 0.35 × 0.19 mm
β = 90.642 (9)°
Data collection top
Stoe IPDS II two-circle
diffractometer
3778 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
3443 reflections with I > 2σ(I)
Tmin = 0.538, Tmax = 0.706Rint = 0.034
6069 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.59 e Å3
S = 1.00Δρmin = 0.60 e Å3
3778 reflectionsAbsolute structure: Flack (1983), 1700 Friedel pairs
290 parametersAbsolute structure parameter: 0.003 (8)
1 restraint
Special details top

Experimental. ;

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
Br10.10708 (4)0.57378 (3)0.75261 (3)0.04064 (14)
O10.2792 (3)0.61771 (19)0.0890 (2)0.0276 (5)
C20.4038 (4)0.5584 (2)0.1524 (3)0.0227 (6)
C30.3955 (4)0.5501 (2)0.2723 (3)0.0231 (7)
C40.2625 (4)0.6123 (2)0.3462 (3)0.0222 (6)
H40.33740.66930.38080.027*
C50.1122 (4)0.6604 (2)0.2682 (3)0.0240 (7)
C60.0442 (5)0.7082 (3)0.3160 (4)0.0295 (8)
H60.05730.71190.39980.035*
C70.1813 (5)0.7506 (3)0.2423 (4)0.0360 (8)
H70.28680.78300.27600.043*
C80.1636 (5)0.7455 (3)0.1208 (4)0.0348 (8)
H80.25880.77290.07090.042*
C90.0093 (5)0.7010 (3)0.0707 (3)0.0299 (7)
H90.00400.69860.01310.036*
C100.1272 (5)0.6595 (2)0.1459 (3)0.0246 (7)
C110.5043 (4)0.4747 (2)0.3365 (3)0.0227 (6)
H110.59400.43700.29340.027*
C120.4863 (4)0.4550 (2)0.4530 (3)0.0237 (7)
C130.3483 (4)0.5097 (3)0.5309 (3)0.0234 (7)
H130.29160.45810.58470.028*
C140.1891 (4)0.5519 (2)0.4502 (3)0.0251 (7)
H140.10880.59730.49910.030*
N140.0711 (4)0.4609 (3)0.4096 (3)0.0340 (7)
O1410.0475 (4)0.4442 (2)0.3057 (3)0.0426 (7)
O1420.0106 (6)0.4048 (4)0.4866 (4)0.0808 (14)
C150.5881 (5)0.3690 (2)0.5044 (3)0.0261 (7)
H150.67390.33430.45510.031*
O150.5706 (4)0.33907 (19)0.6056 (2)0.0329 (6)
C210.5311 (4)0.5078 (2)0.0706 (3)0.0233 (7)
C220.7220 (5)0.4978 (3)0.0954 (3)0.0286 (7)
H220.77220.52230.16840.034*
C230.8374 (5)0.4526 (3)0.0140 (4)0.0368 (8)
H230.96670.44480.03180.044*
C240.7662 (5)0.4180 (3)0.0946 (3)0.0341 (8)
H240.84650.38780.15110.041*
C250.5773 (5)0.4282 (3)0.1190 (3)0.0333 (8)
H250.52780.40440.19260.040*
C260.4612 (5)0.4722 (3)0.0384 (3)0.0283 (7)
H260.33190.47880.05650.034*
C310.4333 (4)0.5917 (2)0.6090 (3)0.0235 (7)
C320.3449 (5)0.6269 (3)0.7118 (3)0.0311 (7)
C330.4251 (6)0.6979 (3)0.7875 (3)0.0379 (9)
H330.36170.71940.85690.046*
C340.5987 (6)0.7368 (3)0.7604 (4)0.0415 (10)
H340.65630.78480.81200.050*
C350.6882 (6)0.7064 (3)0.6592 (4)0.0362 (8)
H350.80620.73450.63990.043*
C360.6062 (5)0.6344 (3)0.5846 (3)0.0295 (7)
H360.67030.61380.51520.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03347 (18)0.0590 (2)0.02960 (18)0.0109 (2)0.00755 (12)0.0032 (2)
O10.0266 (11)0.0314 (11)0.0249 (12)0.0089 (9)0.0029 (9)0.0033 (10)
C20.0192 (13)0.0208 (17)0.0281 (15)0.0000 (12)0.0017 (11)0.0022 (14)
C30.0187 (13)0.0227 (19)0.0279 (16)0.0003 (11)0.0009 (12)0.0020 (12)
C40.0207 (14)0.0209 (14)0.0248 (16)0.0016 (11)0.0025 (12)0.0020 (12)
C50.0245 (16)0.0178 (14)0.0296 (18)0.0003 (12)0.0014 (14)0.0013 (13)
C60.0309 (18)0.0262 (17)0.0315 (19)0.0088 (14)0.0010 (16)0.0020 (14)
C70.0290 (17)0.0307 (18)0.048 (2)0.0116 (15)0.0011 (16)0.0000 (16)
C80.0317 (18)0.0312 (18)0.041 (2)0.0104 (16)0.0047 (16)0.0036 (16)
C90.0307 (17)0.0264 (17)0.0324 (19)0.0023 (14)0.0041 (14)0.0029 (14)
C100.0232 (15)0.0189 (15)0.0317 (18)0.0020 (12)0.0009 (13)0.0000 (13)
C110.0157 (13)0.0228 (15)0.0297 (18)0.0001 (12)0.0018 (12)0.0021 (13)
C120.0187 (14)0.0226 (15)0.0296 (17)0.0011 (12)0.0008 (13)0.0019 (13)
C130.0204 (15)0.0282 (16)0.0218 (16)0.0021 (12)0.0004 (12)0.0000 (13)
C140.0187 (13)0.030 (2)0.0268 (15)0.0019 (12)0.0004 (11)0.0008 (13)
N140.0192 (13)0.0451 (18)0.0375 (18)0.0102 (13)0.0045 (13)0.0108 (15)
O1410.0450 (16)0.0380 (15)0.0445 (18)0.0127 (13)0.0067 (15)0.0049 (13)
O1420.077 (3)0.105 (3)0.060 (2)0.062 (2)0.013 (2)0.030 (2)
C150.0223 (15)0.0235 (16)0.0324 (19)0.0020 (12)0.0031 (13)0.0030 (14)
O150.0415 (14)0.0308 (12)0.0264 (14)0.0070 (11)0.0000 (11)0.0040 (10)
C210.0254 (16)0.0184 (15)0.0260 (16)0.0008 (12)0.0010 (13)0.0007 (13)
C220.0247 (16)0.0304 (17)0.0306 (18)0.0027 (13)0.0010 (13)0.0031 (14)
C230.0259 (17)0.0379 (19)0.047 (2)0.0003 (15)0.0061 (16)0.0034 (17)
C240.0381 (19)0.0295 (17)0.035 (2)0.0041 (15)0.0103 (16)0.0060 (16)
C250.043 (2)0.0305 (19)0.0262 (18)0.0017 (16)0.0006 (16)0.0034 (14)
C260.0260 (16)0.0315 (18)0.0273 (17)0.0003 (14)0.0022 (13)0.0011 (14)
C310.0249 (13)0.0236 (19)0.0219 (14)0.0060 (12)0.0040 (11)0.0024 (13)
C320.0339 (17)0.0328 (18)0.0266 (17)0.0082 (15)0.0032 (14)0.0022 (15)
C330.055 (2)0.034 (2)0.0239 (18)0.0143 (18)0.0043 (16)0.0057 (15)
C340.055 (2)0.0288 (18)0.040 (2)0.0041 (18)0.0176 (19)0.0057 (17)
C350.0363 (19)0.0274 (17)0.044 (2)0.0001 (15)0.0141 (17)0.0030 (16)
C360.0270 (16)0.0294 (18)0.0321 (19)0.0024 (14)0.0041 (14)0.0004 (15)
Geometric parameters (Å, º) top
Br1—C321.902 (4)C14—N141.534 (4)
O1—C21.379 (4)C14—H141.0000
O1—C101.383 (4)N14—O1411.201 (4)
C2—C31.356 (4)N14—O1421.223 (5)
C2—C211.464 (4)C15—O151.213 (4)
C3—C111.451 (4)C15—H150.9500
C3—C41.514 (4)C21—C221.398 (5)
C4—C141.515 (5)C21—C261.401 (5)
C4—C51.520 (4)C22—C231.377 (5)
C4—H41.0000C22—H220.9500
C5—C101.382 (5)C23—C241.395 (6)
C5—C61.398 (5)C23—H230.9500
C6—C71.394 (5)C24—C251.383 (5)
C6—H60.9500C24—H240.9500
C7—C81.377 (6)C25—C261.367 (5)
C7—H70.9500C25—H250.9500
C8—C91.377 (5)C26—H260.9500
C8—H80.9500C31—C361.390 (5)
C9—C101.397 (5)C31—C321.404 (5)
C9—H90.9500C32—C331.387 (6)
C11—C121.345 (5)C33—C341.383 (6)
C11—H110.9500C33—H330.9500
C12—C151.465 (5)C34—C351.373 (6)
C12—C131.511 (4)C34—H340.9500
C13—C311.517 (4)C35—C361.393 (5)
C13—C141.553 (4)C35—H350.9500
C13—H131.0000C36—H360.9500
C2—O1—C10119.6 (3)C4—C14—H14108.4
C3—C2—O1121.7 (3)N14—C14—H14108.4
C3—C2—C21128.5 (3)C13—C14—H14108.4
O1—C2—C21109.7 (3)O141—N14—O142122.1 (3)
C2—C3—C11121.5 (3)O141—N14—C14120.3 (3)
C2—C3—C4122.5 (3)O142—N14—C14117.5 (3)
C11—C3—C4115.9 (3)O15—C15—C12124.6 (3)
C3—C4—C14111.3 (3)O15—C15—H15117.7
C3—C4—C5110.8 (3)C12—C15—H15117.7
C14—C4—C5114.6 (3)C22—C21—C26118.8 (3)
C3—C4—H4106.5C22—C21—C2122.2 (3)
C14—C4—H4106.5C26—C21—C2119.0 (3)
C5—C4—H4106.5C23—C22—C21120.1 (3)
C10—C5—C6117.3 (3)C23—C22—H22120.0
C10—C5—C4120.6 (3)C21—C22—H22120.0
C6—C5—C4122.1 (3)C22—C23—C24120.5 (3)
C7—C6—C5121.0 (4)C22—C23—H23119.7
C7—C6—H6119.5C24—C23—H23119.7
C5—C6—H6119.5C25—C24—C23119.3 (3)
C8—C7—C6119.9 (3)C25—C24—H24120.3
C8—C7—H7120.1C23—C24—H24120.3
C6—C7—H7120.1C26—C25—C24120.6 (3)
C9—C8—C7120.7 (3)C26—C25—H25119.7
C9—C8—H8119.7C24—C25—H25119.7
C7—C8—H8119.7C25—C26—C21120.7 (3)
C8—C9—C10118.6 (3)C25—C26—H26119.7
C8—C9—H9120.7C21—C26—H26119.7
C10—C9—H9120.7C36—C31—C32116.0 (3)
C5—C10—O1122.3 (3)C36—C31—C13121.8 (3)
C5—C10—C9122.5 (3)C32—C31—C13122.1 (3)
O1—C10—C9115.1 (3)C33—C32—C31122.9 (4)
C12—C11—C3124.1 (3)C33—C32—Br1117.8 (3)
C12—C11—H11117.9C31—C32—Br1119.3 (3)
C3—C11—H11117.9C34—C33—C32118.9 (4)
C11—C12—C15118.9 (3)C34—C33—H33120.6
C11—C12—C13122.9 (3)C32—C33—H33120.6
C15—C12—C13117.8 (3)C35—C34—C33120.2 (4)
C12—C13—C31114.6 (3)C35—C34—H34119.9
C12—C13—C14108.2 (3)C33—C34—H34119.9
C31—C13—C14111.7 (3)C34—C35—C36120.1 (4)
C12—C13—H13107.4C34—C35—H35119.9
C31—C13—H13107.4C36—C35—H35119.9
C14—C13—H13107.4C31—C36—C35121.9 (3)
C4—C14—N14112.2 (3)C31—C36—H36119.1
C4—C14—C13112.5 (3)C35—C36—H36119.1
N14—C14—C13106.9 (3)
C10—O1—C2—C38.5 (4)C5—C4—C14—C13176.7 (3)
C10—O1—C2—C21169.5 (3)C12—C13—C14—C451.2 (3)
O1—C2—C3—C11169.1 (3)C31—C13—C14—C475.8 (3)
C21—C2—C3—C118.6 (5)C12—C13—C14—N1472.3 (3)
O1—C2—C3—C46.0 (5)C31—C13—C14—N14160.7 (3)
C21—C2—C3—C4176.3 (3)C4—C14—N14—O1410.6 (4)
C2—C3—C4—C14143.9 (3)C13—C14—N14—O141123.1 (3)
C11—C3—C4—C1431.4 (4)C4—C14—N14—O142177.4 (4)
C2—C3—C4—C515.1 (4)C13—C14—N14—O14253.7 (5)
C11—C3—C4—C5160.2 (3)C11—C12—C15—O15173.6 (3)
C3—C4—C5—C1011.3 (4)C13—C12—C15—O150.6 (5)
C14—C4—C5—C10138.3 (3)C3—C2—C21—C2243.0 (5)
C3—C4—C5—C6169.7 (3)O1—C2—C21—C22139.1 (3)
C14—C4—C5—C642.7 (4)C3—C2—C21—C26139.9 (3)
C10—C5—C6—C71.7 (5)O1—C2—C21—C2638.0 (4)
C4—C5—C6—C7179.2 (3)C26—C21—C22—C230.8 (5)
C5—C6—C7—C80.1 (6)C2—C21—C22—C23177.9 (3)
C6—C7—C8—C91.6 (6)C21—C22—C23—C241.2 (6)
C7—C8—C9—C101.2 (6)C22—C23—C24—C251.0 (6)
C6—C5—C10—O1177.6 (3)C23—C24—C25—C260.4 (6)
C4—C5—C10—O11.5 (5)C24—C25—C26—C210.0 (5)
C6—C5—C10—C92.2 (5)C22—C21—C26—C250.2 (5)
C4—C5—C10—C9178.7 (3)C2—C21—C26—C25177.4 (3)
C2—O1—C10—C512.3 (5)C12—C13—C31—C3619.3 (4)
C2—O1—C10—C9167.9 (3)C14—C13—C31—C36104.2 (3)
C8—C9—C10—C50.8 (5)C12—C13—C31—C32158.9 (3)
C8—C9—C10—O1179.0 (3)C14—C13—C31—C3277.7 (4)
C2—C3—C11—C12172.0 (3)C36—C31—C32—C331.8 (5)
C4—C3—C11—C123.3 (4)C13—C31—C32—C33176.5 (3)
C3—C11—C12—C15172.8 (3)C36—C31—C32—Br1179.7 (2)
C3—C11—C12—C130.2 (5)C13—C31—C32—Br12.1 (4)
C11—C12—C13—C31101.9 (4)C31—C32—C33—C340.8 (6)
C15—C12—C13—C3185.4 (4)Br1—C32—C33—C34179.3 (3)
C11—C12—C13—C1423.4 (4)C32—C33—C34—C350.9 (6)
C15—C12—C13—C14149.3 (3)C33—C34—C35—C361.4 (6)
C3—C4—C14—N1464.0 (3)C32—C31—C36—C351.2 (5)
C5—C4—C14—N1462.7 (3)C13—C31—C36—C35177.1 (3)
C3—C4—C14—C1356.5 (3)C34—C35—C36—C310.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O15i1.002.343.266 (4)154
C7—H7···O15ii0.952.553.487 (5)168
C25—H25···O15iii0.952.453.314 (4)151
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y+1/2, z+1; (iii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC26H18BrNO4
Mr488.32
Crystal system, space groupMonoclinic, P21
Temperature (K)173
a, b, c (Å)7.1583 (8), 13.2036 (12), 11.2510 (14)
β (°) 90.642 (9)
V3)1063.3 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.97
Crystal size (mm)0.36 × 0.35 × 0.19
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2009; Blessing, 1995)
Tmin, Tmax0.538, 0.706
No. of measured, independent and
observed [I > 2σ(I)] reflections
6069, 3778, 3443
Rint0.034
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.087, 1.00
No. of reflections3778
No. of parameters290
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.59, 0.60
Absolute structureFlack (1983), 1700 Friedel pairs
Absolute structure parameter0.003 (8)

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O15i1.002.343.266 (4)153.5
C7—H7···O15ii0.952.553.487 (5)168.4
C25—H25···O15iii0.952.453.314 (4)150.9
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y+1/2, z+1; (iii) x, y, z1.
 

References

First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationEllis, G. P. & Lockhart, I. M. (2007). The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones, Vol. 31, edited by G. P. Ellis, pp. 1–1196. London: Wiley-VCH.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationRueping, M., Dufour, J. & Maji, M. S. (2011). In preparation.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar

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