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In the title cocrystal, 0.972(C18H19NO4).0.028(C17H16BrNO3), which arose from an impure starting material, all the atoms are overlapped except for one OMe group and the Br atom. The dihedral angle between the benzene ring mean planes is 18.20 (13)°. A weak N—H...O hydrogen bond helps to establish the non-centrosymmetric crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041840/tk2192sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041840/tk2192Isup2.hkl
Contains datablock I

CCDC reference: 663697

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.036
  • wR factor = 0.098
  • Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.16 PLAT128_ALERT_4_C Non-standard setting of Space group Pc .... Pn PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT420_ALERT_2_C D-H Without Acceptor N1 - H5A ... ?
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 1540 Count of symmetry unique reflns 1565 Completeness (_total/calc) 98.40% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our on-going studies of chalcone derivatives as possible non-linear optical materials (Uchida et al., 1998; Harrison et al., 2007), we now report the synthesis and structure of the non-centrosymmetric title co-crystal, (I) + (II), (Fig. 1). All the atoms are superimposed in the crystal, except for O4/C18/H18A/H18B/H18C in (I) and Br1 in (II). A similar co-crystal was recently described (Ravindra et al., 2007).

The bond lengths and angles for (I) + (II) are normal (Allen et al., 1995). The C16 and C18 atoms are almost co-planar with the C1–C6 benzene ring, whereas C17 is significantly displaced, by 1.026 (6) Å. The dihedral angle between two benzene rings (C1–C6 and C10–C15) is 18.20 (13)°. The central enone fragment (C7/C8/C9/O1) makes dihedral angles of 7.8 (3)° and 11.6 (3)° with C1–C6 and C10–C15, respectively.

The non-centrosymmetric packing for (I) + (II) is consolidated by a weak N—H···O hydrogen bond (Table 1), resulting in C(8) chains propagating in [101].

Related literature top

For background, see: Uchida et al. (1998); Harrison et al. (2007); Ravindra et al. (2007). For reference structural data, see: Allen et al. (1995).

Experimental top

A Claisen–Schmidt condensation reaction was used: a solution of ethanol (20 ml) and 10% aqueous sodium hydroxide (5 ml) solution were taken in a conical flask. A previously prepared portion of 3,4,5-trimethoxy benzaldehyde (0.001 mol) and 1-(4-aminophenyl)ethanone (0.001 mol) dissolved in ethanol (25 ml) was added to the conical flask with stirring and the temperature of the solution was maintained between 293 and 298 K. A precipitate was obtained after stirring the solution for about five minutes. The remaining portion of the aldehyde and ketone mixture was added and the solution was stirred for about 60 minutes. The solid product was filtered and washed with excess water to remove the alkali and dried. Yellow blocks of (I) + (II) were grown by slow evaporation of an acetone solution. The 3,4,5-trimethoxybenzaldehyde starting material was contaminated with some 3-bromo-4,5-dimethoxybenzaldehyde, resulting also in the formation of (II). The presence of the Br atom in the starting material as well as the product was confirmed by performing the halogen test.

Refinement top

Due to negligible amonalous scattering, Friedel pairs were merged before refinement.

After initial modelling as the expected compound (I), high residuals (wR2 > 0.15) and a significant difference peak in the vicinity of O4 and C18 remained. The separation of the peak and C2 suggested the presence of a C—Br bond (Ravindra et al., 2007). Refinement as a co-crystal of (I) + (II) (occupancies of the –O4—C18 and –Br1 groups/atoms attached to C2 refined with their sum constrained to unity) converged to a physically plausible answer with lower residuals.

The hydrogen atoms were placed in calculated positions (N—H = 0.86 Å, C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate but not to tip to best fit the electron density.

Structure description top

As part of our on-going studies of chalcone derivatives as possible non-linear optical materials (Uchida et al., 1998; Harrison et al., 2007), we now report the synthesis and structure of the non-centrosymmetric title co-crystal, (I) + (II), (Fig. 1). All the atoms are superimposed in the crystal, except for O4/C18/H18A/H18B/H18C in (I) and Br1 in (II). A similar co-crystal was recently described (Ravindra et al., 2007).

The bond lengths and angles for (I) + (II) are normal (Allen et al., 1995). The C16 and C18 atoms are almost co-planar with the C1–C6 benzene ring, whereas C17 is significantly displaced, by 1.026 (6) Å. The dihedral angle between two benzene rings (C1–C6 and C10–C15) is 18.20 (13)°. The central enone fragment (C7/C8/C9/O1) makes dihedral angles of 7.8 (3)° and 11.6 (3)° with C1–C6 and C10–C15, respectively.

The non-centrosymmetric packing for (I) + (II) is consolidated by a weak N—H···O hydrogen bond (Table 1), resulting in C(8) chains propagating in [101].

For background, see: Uchida et al. (1998); Harrison et al. (2007); Ravindra et al. (2007). For reference structural data, see: Allen et al. (1995).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) + (II) showing 50% displacement ellipsoids (H atoms are drawn as spheres of arbitrary radius). The Br atom of (II) is connected to the benzene ring with a dashed line.
[Figure 2] Fig. 2. Part of a hydrogen-bonded chain in (I) + (II) with hydrogen bonds shown as dashed lines. All the C-bound hydrogen atoms and Br1 omitted for clarity. Symmetry code as in Table 1; additionally (ii) x + 1, y, z - 1.
1-(4-Aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one–1-(4- aminophenyl)-3-(3-bromo-4,5-trimethoxyphenyl)prop-2-en-1-one (0.972/0.028) top
Crystal data top
0.972C18H19NO4·0.028C17H16BrNO3F(000) = 333
Mr = 314.81Dx = 1.322 Mg m3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yacCell parameters from 3137 reflections
a = 4.2227 (4) Åθ = 5.0–26.0°
b = 12.2001 (12) ŵ = 0.17 mm1
c = 15.4865 (16) ÅT = 291 K
β = 97.506 (2)°Block, yellow
V = 790.99 (14) Å30.55 × 0.45 × 0.40 mm
Z = 2
Data collection top
Bruker SMART1000 CCD
diffractometer
1380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 26.0°, θmin = 5.0°
ω scansh = 55
5129 measured reflectionsk = 1315
1540 independent reflectionsl = 1919
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.0717P]
where P = (Fo2 + 2Fc2)/3
1540 reflections(Δ/σ)max < 0.001
215 parametersΔρmax = 0.15 e Å3
2 restraintsΔρmin = 0.16 e Å3
Crystal data top
0.972C18H19NO4·0.028C17H16BrNO3V = 790.99 (14) Å3
Mr = 314.81Z = 2
Monoclinic, PnMo Kα radiation
a = 4.2227 (4) ŵ = 0.17 mm1
b = 12.2001 (12) ÅT = 291 K
c = 15.4865 (16) Å0.55 × 0.45 × 0.40 mm
β = 97.506 (2)°
Data collection top
Bruker SMART1000 CCD
diffractometer
1380 reflections with I > 2σ(I)
5129 measured reflectionsRint = 0.024
1540 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0362 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.04Δρmax = 0.15 e Å3
1540 reflectionsΔρmin = 0.16 e Å3
215 parameters
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)
C10.6830 (7)0.6305 (2)0.59663 (17)0.0456 (6)
H1A0.75600.61770.54340.055*
C20.6978 (6)0.5477 (2)0.65815 (18)0.0474 (6)
C30.5932 (6)0.5659 (2)0.73839 (17)0.0448 (6)
C40.4792 (6)0.6690 (2)0.75739 (16)0.0459 (6)
C50.4595 (7)0.7520 (2)0.69540 (17)0.0442 (6)
H50.38000.82040.70800.053*
C60.5592 (6)0.7328 (2)0.61415 (16)0.0421 (6)
C70.5229 (7)0.8205 (2)0.54870 (17)0.0444 (6)
H70.42300.88430.56390.053*
C80.6162 (7)0.8188 (2)0.47081 (17)0.0484 (6)
H80.73310.75870.45590.058*
C90.5449 (7)0.9074 (2)0.40564 (16)0.0461 (6)
C100.6270 (6)0.8898 (2)0.31701 (15)0.0424 (6)
C110.8102 (7)0.8023 (2)0.29464 (16)0.0460 (6)
H110.88900.75210.33730.055*
C120.8783 (7)0.7880 (2)0.21047 (18)0.0515 (6)
H121.00160.72860.19740.062*
C130.7639 (7)0.8615 (2)0.14522 (17)0.0484 (6)
C140.5748 (7)0.9488 (2)0.16634 (18)0.0513 (7)
H140.49330.99820.12340.062*
C150.5078 (7)0.9624 (2)0.25052 (17)0.0485 (6)
H150.38101.02100.26340.058*
C160.2691 (10)0.7785 (3)0.8611 (2)0.0663 (9)
H16A0.21560.77520.91940.099*
H16B0.08050.79430.82140.099*
H16C0.42450.83520.85740.099*
C170.8445 (10)0.4671 (4)0.8583 (3)0.0888 (13)
H17A0.80330.40990.89780.133*
H17B0.88610.53440.88990.133*
H17C1.02690.44800.83040.133*
C180.9253 (9)0.4213 (3)0.5689 (5)0.0620 (9)0.972 (3)
H18A1.01910.34950.57290.093*0.972 (3)
H18B1.08540.47440.56000.093*0.972 (3)
H18C0.75700.42350.52080.093*0.972 (3)
O10.4088 (7)0.99177 (17)0.42458 (14)0.0702 (7)
O20.3921 (5)0.68052 (19)0.83999 (14)0.0622 (6)
O30.5817 (5)0.48021 (17)0.79608 (14)0.0593 (6)
O40.8057 (7)0.44333 (19)0.64595 (19)0.0619 (6)0.972 (3)
N10.8291 (9)0.8461 (2)0.06121 (17)0.0708 (8)
H5A0.94110.79070.04890.085*
H5B0.75790.89180.02110.085*
Br10.912 (3)0.4202 (10)0.6089 (11)0.040 (5)*0.028 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0555 (15)0.0412 (14)0.0408 (13)0.0016 (11)0.0094 (11)0.0023 (10)
C20.0514 (15)0.0376 (13)0.0524 (15)0.0011 (11)0.0035 (12)0.0005 (12)
C30.0492 (15)0.0405 (13)0.0443 (13)0.0038 (11)0.0048 (11)0.0074 (10)
C40.0550 (15)0.0467 (14)0.0362 (13)0.0077 (12)0.0071 (11)0.0019 (10)
C50.0555 (15)0.0382 (12)0.0395 (13)0.0008 (11)0.0081 (11)0.0002 (10)
C60.0508 (14)0.0384 (12)0.0366 (12)0.0032 (11)0.0041 (10)0.0007 (10)
C70.0578 (15)0.0344 (12)0.0420 (13)0.0012 (11)0.0102 (11)0.0010 (10)
C80.0663 (17)0.0377 (13)0.0421 (14)0.0027 (11)0.0112 (12)0.0009 (10)
C90.0643 (17)0.0353 (13)0.0402 (13)0.0011 (11)0.0123 (12)0.0005 (10)
C100.0557 (15)0.0337 (12)0.0383 (13)0.0071 (11)0.0085 (11)0.0007 (10)
C110.0611 (16)0.0390 (13)0.0387 (13)0.0027 (11)0.0090 (11)0.0058 (10)
C120.0695 (18)0.0412 (14)0.0467 (14)0.0016 (13)0.0178 (12)0.0011 (11)
C130.0653 (17)0.0422 (14)0.0384 (14)0.0162 (12)0.0097 (12)0.0012 (11)
C140.0645 (18)0.0468 (14)0.0416 (13)0.0102 (12)0.0035 (12)0.0123 (11)
C150.0622 (16)0.0364 (12)0.0477 (14)0.0030 (11)0.0099 (12)0.0050 (11)
C160.085 (2)0.082 (2)0.0358 (13)0.0068 (18)0.0221 (13)0.0015 (15)
C170.081 (2)0.090 (3)0.090 (3)0.011 (2)0.010 (2)0.050 (2)
C180.077 (3)0.0448 (19)0.065 (3)0.0146 (16)0.0096 (19)0.0057 (17)
O10.1155 (19)0.0448 (11)0.0544 (12)0.0213 (12)0.0265 (12)0.0006 (9)
O20.0847 (15)0.0613 (12)0.0435 (11)0.0035 (11)0.0191 (10)0.0172 (9)
O30.0662 (13)0.0501 (12)0.0604 (12)0.0052 (10)0.0039 (9)0.0197 (9)
O40.0846 (16)0.0398 (11)0.0636 (15)0.0104 (11)0.0186 (15)0.0063 (10)
N10.117 (2)0.0554 (15)0.0423 (14)0.0101 (16)0.0203 (14)0.0006 (12)
Geometric parameters (Å, º) top
C1—C21.384 (4)C11—H110.9300
C1—C61.394 (4)C12—C131.390 (4)
C1—H1A0.9300C12—H120.9300
C2—O41.374 (4)C13—N11.377 (4)
C2—C31.390 (4)C13—C141.395 (4)
C2—Br12.000 (17)C14—C151.380 (4)
C3—O31.380 (3)C14—H140.9300
C3—C41.392 (4)C15—H150.9300
C4—O21.384 (3)C16—O21.361 (4)
C4—C51.391 (4)C16—H16A0.9600
C5—C61.398 (3)C16—H16B0.9600
C5—H50.9300C16—H16C0.9600
C6—C71.468 (4)C17—O31.380 (4)
C7—C81.317 (4)C17—H17A0.9600
C7—H70.9300C17—H17B0.9600
C8—C91.483 (4)C17—H17C0.9600
C8—H80.9300C18—O41.382 (8)
C9—O11.233 (3)C18—H18A0.9600
C9—C101.475 (3)C18—H18B0.9600
C10—C111.389 (4)C18—H18C0.9600
C10—C151.401 (3)N1—H5A0.8600
C11—C121.382 (4)N1—H5B0.8600
C2—C1—C6120.2 (2)C11—C12—H12119.7
C2—C1—H1A119.9C13—C12—H12119.7
C6—C1—H1A119.9N1—C13—C12120.3 (3)
O4—C2—C1124.6 (3)N1—C13—C14121.1 (3)
O4—C2—C3114.9 (2)C12—C13—C14118.5 (2)
C1—C2—C3120.6 (2)C15—C14—C13120.5 (2)
C1—C2—Br1106.7 (5)C15—C14—H14119.8
C3—C2—Br1132.6 (5)C13—C14—H14119.8
O3—C3—C2120.0 (3)C14—C15—C10121.3 (3)
O3—C3—C4120.3 (2)C14—C15—H15119.3
C2—C3—C4119.5 (2)C10—C15—H15119.3
O2—C4—C5124.4 (2)O2—C16—H16A109.5
O2—C4—C3115.4 (2)O2—C16—H16B109.5
C5—C4—C3120.2 (2)H16A—C16—H16B109.5
C4—C5—C6120.1 (2)O2—C16—H16C109.5
C4—C5—H5120.0H16A—C16—H16C109.5
C6—C5—H5120.0H16B—C16—H16C109.5
C1—C6—C5119.4 (2)O3—C17—H17A109.5
C1—C6—C7121.8 (2)O3—C17—H17B109.5
C5—C6—C7118.9 (2)H17A—C17—H17B109.5
C8—C7—C6127.2 (2)O3—C17—H17C109.5
C8—C7—H7116.4H17A—C17—H17C109.5
C6—C7—H7116.4H17B—C17—H17C109.5
C7—C8—C9123.6 (2)O4—C18—H18A108.4
C7—C8—H8118.2O4—C18—H18B109.7
C9—C8—H8118.2H18A—C18—H18B109.5
O1—C9—C10121.1 (2)O4—C18—H18C110.3
O1—C9—C8120.4 (2)H18A—C18—H18C109.5
C10—C9—C8118.4 (2)H18B—C18—H18C109.5
C11—C10—C15117.5 (2)C16—O2—C4117.9 (2)
C11—C10—C9123.4 (2)C3—O3—C17116.5 (3)
C15—C10—C9119.1 (2)C2—O4—C18117.7 (3)
C12—C11—C10121.6 (2)C13—N1—H5A120.0
C12—C11—H11119.2C13—N1—H5B120.0
C10—C11—H11119.2H5A—N1—H5B120.0
C11—C12—C13120.6 (3)
C6—C1—C2—O4177.8 (3)C7—C8—C9—C10172.5 (3)
C6—C1—C2—C30.8 (4)O1—C9—C10—C11172.7 (3)
C6—C1—C2—Br1176.8 (4)C8—C9—C10—C1110.1 (4)
O4—C2—C3—O34.6 (4)O1—C9—C10—C159.3 (4)
C1—C2—C3—O3174.1 (3)C8—C9—C10—C15167.8 (3)
Br1—C2—C3—O311.1 (6)C15—C10—C11—C121.2 (4)
O4—C2—C3—C4180.0 (2)C9—C10—C11—C12179.1 (3)
C1—C2—C3—C41.4 (4)C10—C11—C12—C130.0 (4)
Br1—C2—C3—C4173.5 (5)C11—C12—C13—N1179.2 (3)
O3—C3—C4—O27.0 (4)C11—C12—C13—C141.1 (4)
C2—C3—C4—O2177.6 (2)N1—C13—C14—C15179.1 (3)
O3—C3—C4—C5173.2 (3)C12—C13—C14—C151.0 (4)
C2—C3—C4—C52.3 (4)C13—C14—C15—C100.1 (4)
O2—C4—C5—C6178.8 (2)C11—C10—C15—C141.2 (4)
C3—C4—C5—C61.0 (4)C9—C10—C15—C14179.3 (3)
C2—C1—C6—C52.0 (4)C5—C4—O2—C162.3 (4)
C2—C1—C6—C7176.5 (3)C3—C4—O2—C16177.9 (3)
C4—C5—C6—C11.1 (4)C2—C3—O3—C1794.6 (4)
C4—C5—C6—C7177.4 (3)C4—C3—O3—C1790.0 (4)
C1—C6—C7—C84.9 (4)C1—C2—O4—Br116.5 (12)
C5—C6—C7—C8176.6 (3)C3—C2—O4—Br1164.8 (12)
C6—C7—C8—C9174.5 (3)C1—C2—O4—C184.0 (4)
C7—C8—C9—O14.7 (5)C3—C2—O4—C18177.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H5B···O1i0.862.212.948 (3)143
Symmetry code: (i) x+1/2, y+2, z1/2.

Experimental details

Crystal data
Chemical formula0.972C18H19NO4·0.028C17H16BrNO3
Mr314.81
Crystal system, space groupMonoclinic, Pn
Temperature (K)291
a, b, c (Å)4.2227 (4), 12.2001 (12), 15.4865 (16)
β (°) 97.506 (2)
V3)790.99 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.55 × 0.45 × 0.40
Data collection
DiffractometerBruker SMART1000 CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5129, 1540, 1380
Rint0.024
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.098, 1.04
No. of reflections1540
No. of parameters215
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H5B···O1i0.862.212.948 (3)143
Symmetry code: (i) x+1/2, y+2, z1/2.
 

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