Download citation
Download citation
link to html
The title cocrystal, 0.919 (3)(C23H26O7·1.333H2O)·0.081 (3)(C22H20Br2O5·1.333H2O), arose due to the presence of an impurity in one of the starting materials. In both cases, the complete organic mol­ecule has twofold rotation symmetry, with the central C=O group lying on the rotation axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021551/bv2056sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021551/bv2056Isup2.hkl
Contains datablock I

CCDC reference: 651418

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • H-atom completeness 91%
  • Disorder in main residue
  • R factor = 0.064
  • wR factor = 0.158
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O51 .. 2.73 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O51 .. 2.73 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc. PLAT395_ALERT_2_C Deviating X-O-Y Angle from 120 Deg for <O51 150.40 Deg. PLAT430_ALERT_2_C Short Inter D...A Contact O1 .. O52 .. 2.86 Ang. PLAT430_ALERT_2_C Short Inter D...A Contact O1 .. O52 .. 2.86 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 12.60 Deg. O4 -C8 -BR1 1.555 1.555 1.555
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C22.84 H28.18 Br0.16 O8.17 Atom count from the _atom_site data: C22.83799 H25.51399 Br0.162 O8 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C22.84 H28.18 Br0.16 O8.17 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 91.36 91.35 0.01 H 112.72 102.06 10.66 Br 0.64 0.65 -0.01 O 32.68 32.63 0.05
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1,5-Bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 1.333-hydrate–1,5- bis(3-bromo-4,5-dimethoxyphenyl)penta-1,4-dien-3-one 1.333-hydrate 0.919 (3):0.081 (3) cocrystal top
Crystal data top
0.919C23H26O7·0.081C21H20Br2O5·1.333H2OF(000) = 945
Mr = 446.26Dx = 1.394 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2202 reflections
a = 34.035 (3) Åθ = 2.9–27.5°
b = 8.4017 (9) ŵ = 0.40 mm1
c = 7.4385 (5) ÅT = 120 K
β = 90.305 (6)°Rod, yellow
V = 2127.0 (3) Å30.44 × 0.16 × 0.04 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2346 independent reflections
Radiation source: fine-focus sealed tube1278 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ω and φ scansθmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 4443
Tmin = 0.842, Tmax = 0.984k = 107
8542 measured reflectionsl = 89
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0648P)2 + 0.7883P]
where P = (Fo2 + 2Fc2)/3
2346 reflections(Δ/σ)max < 0.001
153 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.32 e Å3
Special details top

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*/UeqOcc. (<1)
C10.50000.4937 (5)0.25000.0279 (9)
C20.53215 (7)0.5859 (3)0.3301 (3)0.0293 (6)
H20.52930.69830.33710.035*
C30.56507 (7)0.5209 (3)0.3934 (3)0.0279 (6)
H30.56740.40860.38290.033*
C40.59804 (7)0.6052 (3)0.4776 (3)0.0255 (6)
C50.63270 (7)0.5226 (3)0.5148 (3)0.0253 (6)
H50.63430.41240.48720.030*
C60.66480 (7)0.5986 (3)0.5912 (3)0.0250 (6)
C70.66279 (8)0.7617 (3)0.6267 (3)0.0278 (6)
C80.62785 (8)0.8441 (3)0.5931 (3)0.0276 (6)
C90.59558 (8)0.7673 (3)0.5210 (3)0.0274 (6)
H90.57180.82390.50080.033*
C100.70173 (8)0.3620 (3)0.6116 (3)0.0334 (7)
H10A0.72760.32380.65090.050*
H10B0.69790.33670.48410.050*
H10C0.68120.30990.68260.050*
C110.71550 (8)0.9345 (3)0.5737 (4)0.0354 (7)
H11A0.73530.99880.63670.053*
H11B0.69701.00490.51110.053*
H11C0.72850.86530.48620.053*
C120.59576 (13)1.0940 (4)0.5921 (4)0.0346 (8)0.919 (3)
H12A0.59971.20510.62840.052*0.919 (3)
H12B0.57241.05150.65200.052*0.919 (3)
H12C0.59211.08860.46150.052*0.919 (3)
O10.50000.3467 (3)0.25000.0358 (7)
O20.69958 (5)0.5252 (2)0.6358 (2)0.0317 (5)
O30.69468 (5)0.8390 (2)0.7011 (2)0.0328 (5)
O40.62902 (9)1.0031 (4)0.6420 (3)0.0366 (7)0.919 (3)
Br10.61971 (18)1.0626 (7)0.6264 (7)0.0286 (17)*0.081 (3)
O510.4922 (2)0.0285 (8)0.1864 (9)0.0604 (19)*0.33
O520.4914 (2)0.0493 (9)0.0659 (11)0.076 (2)*0.33
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.030 (2)0.030 (2)0.0236 (18)0.0000.0019 (15)0.000
C20.0308 (15)0.0243 (14)0.0327 (14)0.0010 (13)0.0019 (11)0.0012 (11)
C30.0320 (16)0.0263 (15)0.0253 (13)0.0012 (12)0.0019 (11)0.0011 (11)
C40.0277 (14)0.0263 (15)0.0226 (12)0.0005 (12)0.0009 (10)0.0003 (10)
C50.0315 (15)0.0197 (13)0.0247 (13)0.0010 (12)0.0017 (11)0.0006 (10)
C60.0270 (15)0.0271 (15)0.0209 (12)0.0018 (12)0.0017 (10)0.0005 (10)
C70.0329 (15)0.0268 (15)0.0238 (13)0.0057 (12)0.0024 (11)0.0007 (11)
C80.0371 (17)0.0211 (15)0.0245 (13)0.0035 (12)0.0015 (11)0.0003 (10)
C90.0310 (15)0.0239 (14)0.0272 (13)0.0034 (12)0.0019 (11)0.0011 (11)
C100.0324 (17)0.0368 (17)0.0308 (14)0.0054 (13)0.0050 (11)0.0009 (12)
C110.0352 (16)0.0328 (17)0.0384 (15)0.0078 (13)0.0009 (12)0.0084 (12)
C120.049 (3)0.0247 (17)0.0306 (17)0.0035 (17)0.0008 (16)0.0013 (13)
O10.0354 (16)0.0317 (17)0.0403 (15)0.0000.0017 (12)0.000
O20.0261 (11)0.0349 (11)0.0340 (10)0.0006 (9)0.0042 (8)0.0001 (8)
O30.0382 (11)0.0305 (11)0.0298 (9)0.0086 (9)0.0052 (8)0.0034 (8)
O40.0403 (17)0.0331 (16)0.0365 (14)0.0034 (14)0.0066 (10)0.0019 (11)
Geometric parameters (Å, º) top
C1—O11.235 (4)C8—Br11.873 (6)
C1—C21.465 (3)C9—H90.9500
C1—C2i1.465 (3)C10—O21.385 (3)
C2—C31.330 (3)C10—H10A0.9800
C2—H20.9500C10—H10B0.9800
C3—C41.465 (3)C10—H10C0.9800
C3—H30.9500C11—O31.432 (3)
C4—C51.395 (3)C11—H11A0.9800
C4—C91.402 (3)C11—H11B0.9800
C5—C61.385 (3)C11—H11C0.9800
C5—H50.9500C12—O41.414 (6)
C6—O21.374 (3)C12—H12A0.9800
C6—C71.397 (3)C12—H12B0.9800
C7—O31.379 (3)C12—H12C0.9800
C7—C81.398 (3)O51—O520.914 (8)
C8—C91.380 (3)O51—O51i1.084 (12)
C8—O41.385 (4)O52—O52ii1.411 (15)
O1—C1—C2121.94 (17)C9—C8—Br1113.1 (3)
O1—C1—C2i121.94 (17)O4—C8—Br112.6 (2)
C2—C1—C2i116.1 (3)C7—C8—Br1126.0 (3)
C3—C2—C1123.5 (3)C8—C9—C4119.7 (2)
C3—C2—H2118.2C8—C9—H9120.2
C1—C2—H2118.2C4—C9—H9120.2
C2—C3—C4126.5 (3)O2—C10—H10A109.5
C2—C3—H3116.8O2—C10—H10B109.5
C4—C3—H3116.8H10A—C10—H10B109.5
C5—C4—C9119.3 (2)O2—C10—H10C109.5
C5—C4—C3119.3 (2)H10A—C10—H10C109.5
C9—C4—C3121.4 (2)H10B—C10—H10C109.5
C6—C5—C4121.1 (2)O3—C11—H11A109.5
C6—C5—H5119.5O3—C11—H11B109.5
C4—C5—H5119.5H11A—C11—H11B109.5
O2—C6—C5124.7 (2)O3—C11—H11C109.5
O2—C6—C7115.9 (2)H11A—C11—H11C109.5
C5—C6—C7119.4 (2)H11B—C11—H11C109.5
O3—C7—C6119.9 (2)C6—O2—C10117.31 (19)
O3—C7—C8120.4 (2)C7—O3—C11112.94 (18)
C6—C7—C8119.6 (2)C8—O4—C12115.5 (2)
C9—C8—O4125.1 (3)O52—O51—O51i150.1 (13)
C9—C8—C7120.8 (2)O51—O52—O52ii124.1 (12)
O4—C8—C7114.1 (2)
O1—C1—C2—C36.3 (3)C6—C7—C8—O4177.0 (2)
C2i—C1—C2—C3173.7 (3)O3—C7—C8—Br14.1 (4)
C1—C2—C3—C4178.91 (19)C6—C7—C8—Br1178.4 (3)
C2—C3—C4—C5171.3 (2)O4—C8—C9—C4179.7 (2)
C2—C3—C4—C98.4 (4)C7—C8—C9—C41.2 (3)
C9—C4—C5—C60.9 (3)Br1—C8—C9—C4176.0 (2)
C3—C4—C5—C6178.8 (2)C5—C4—C9—C82.5 (3)
C4—C5—C6—O2178.4 (2)C3—C4—C9—C8177.2 (2)
C4—C5—C6—C71.9 (3)C5—C6—O2—C103.8 (3)
O2—C6—C7—O30.4 (3)C7—C6—O2—C10176.5 (2)
C5—C6—C7—O3179.3 (2)C6—C7—O3—C11104.9 (2)
O2—C6—C7—C8177.1 (2)C8—C7—O3—C1177.7 (3)
C5—C6—C7—C83.2 (3)C9—C8—O4—C128.0 (4)
O3—C7—C8—C9179.1 (2)C7—C8—O4—C12173.4 (2)
C6—C7—C8—C91.6 (3)Br1—C8—O4—C1210.6 (9)
O3—C7—C8—O40.5 (3)O51i—O51—O52—O52ii78.4 (19)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds