Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004847/wn6141sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004847/wn6141Isup2.hkl |
CCDC reference: 209941
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.054
- wR factor = 0.100
- Data-to-parameter ratio = 13.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.789 0.935 RT(exp) = 1.184
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
To a solution of acetophenone in acetic acid, bromine in acetic acid was added and the contents were shaken for 10–15 min and allowed to stand for half an hour. Crushed ice was added to the mixture and the resulting solid was washed with absolute alcohol to yield phenacyl bromide. The latter was dissolved in ethanol and slowly added to an ethanol solution of p-bromoaniline. The reaction mixture was heated for 15–20 min until the colour changed to dark brown. The contents were cooled to room temperature. The solid obtained by filtration was crystallized from dry ethanol.
The H atoms were positioned geometrically and allowed to ride on their parent atoms, with Uiso(H) equal to Ueq of the parent atom.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1996) in the suite WinGX (Farrugia, 1999); software used to prepare material for publication: PLATON (Spek, 1990).
C14H12BrNO | Z = 2 |
Mr = 290.15 | F(000) = 292 |
Triclinic, P1 | Dx = 1.587 Mg m−3 |
Hall symbol: -P 1 | Melting point: 439 K |
a = 5.7609 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.5689 (11) Å | Cell parameters from 903 reflections |
c = 14.227 (2) Å | θ = 2.8–25.0° |
α = 99.374 (2)° | µ = 3.37 mm−1 |
β = 91.216 (2)° | T = 293 K |
γ = 96.778 (2)° | Rod, pale yellow |
V = 607.27 (16) Å3 | 0.40 × 0.06 × 0.02 × 0.04 (radius) mm |
Bruker SMART CCD area-detector diffractometer | 1748 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
Graphite monochromator | θmax = 25.1°, θmin = 1.5° |
ϕ and ω scans | h = −6→6 |
5884 measured reflections | k = −9→9 |
2133 independent reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0397P)2] where P = (Fo2 + 2Fc2)/3 |
2133 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C14H12BrNO | γ = 96.778 (2)° |
Mr = 290.15 | V = 607.27 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.7609 (9) Å | Mo Kα radiation |
b = 7.5689 (11) Å | µ = 3.37 mm−1 |
c = 14.227 (2) Å | T = 293 K |
α = 99.374 (2)° | 0.40 × 0.06 × 0.02 × 0.04 (radius) mm |
β = 91.216 (2)° |
Bruker SMART CCD area-detector diffractometer | 1748 reflections with I > 2σ(I) |
5884 measured reflections | Rint = 0.043 |
2133 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.15 | Δρmax = 0.38 e Å−3 |
2133 reflections | Δρmin = −0.40 e Å−3 |
154 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.43743 (9) | 0.85277 (7) | 0.16251 (3) | 0.0558 (2) | |
C4 | −0.0071 (7) | 0.7351 (5) | 0.4223 (3) | 0.0376 (10) | |
C9 | −0.1970 (7) | 0.7097 (5) | 0.7617 (3) | 0.0366 (10) | |
N1 | −0.1440 (6) | 0.6989 (5) | 0.4956 (2) | 0.0486 (10) | |
H1 | −0.2859 | 0.6503 | 0.4823 | 0.058* | |
O1 | −0.4484 (6) | 0.6275 (5) | 0.6248 (2) | 0.0618 (9) | |
C1 | 0.2574 (7) | 0.8076 (5) | 0.2686 (3) | 0.0392 (10) | |
C6 | 0.0314 (8) | 0.7235 (6) | 0.2534 (3) | 0.0445 (11) | |
H6 | −0.0323 | 0.6894 | 0.1916 | 0.053* | |
C7 | −0.0631 (7) | 0.7378 (6) | 0.5940 (3) | 0.0405 (10) | |
H7A | −0.0091 | 0.8656 | 0.6111 | 0.049* | |
H7B | 0.0679 | 0.6717 | 0.6027 | 0.049* | |
C2 | 0.3534 (8) | 0.8543 (6) | 0.3592 (3) | 0.0454 (11) | |
H2 | 0.5066 | 0.9099 | 0.3695 | 0.054* | |
C3 | 0.2221 (7) | 0.8186 (6) | 0.4356 (3) | 0.0441 (11) | |
H3 | 0.2883 | 0.8512 | 0.4971 | 0.053* | |
C8 | −0.2535 (8) | 0.6866 (5) | 0.6579 (3) | 0.0408 (10) | |
C5 | −0.0992 (7) | 0.6899 (6) | 0.3288 (3) | 0.0422 (11) | |
H5 | −0.2529 | 0.6357 | 0.3177 | 0.051* | |
C14 | −0.3667 (8) | 0.6519 (6) | 0.8206 (3) | 0.0503 (12) | |
H14 | −0.5136 | 0.6004 | 0.7947 | 0.060* | |
C13 | −0.3209 (10) | 0.6695 (7) | 0.9168 (4) | 0.0628 (14) | |
H13 | −0.4373 | 0.6306 | 0.9557 | 0.075* | |
C10 | 0.0199 (8) | 0.7858 (6) | 0.8022 (3) | 0.0515 (12) | |
H10 | 0.1363 | 0.8260 | 0.7636 | 0.062* | |
C11 | 0.0652 (9) | 0.8025 (7) | 0.8986 (4) | 0.0672 (15) | |
H11 | 0.2116 | 0.8537 | 0.9251 | 0.081* | |
C12 | −0.1064 (11) | 0.7434 (7) | 0.9561 (3) | 0.0680 (15) | |
H12 | −0.0761 | 0.7538 | 1.0214 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0572 (3) | 0.0634 (3) | 0.0492 (3) | 0.0032 (2) | 0.0180 (2) | 0.0171 (2) |
C4 | 0.041 (3) | 0.039 (2) | 0.034 (2) | 0.006 (2) | 0.004 (2) | 0.0058 (19) |
C9 | 0.044 (3) | 0.031 (2) | 0.034 (2) | 0.0040 (19) | 0.006 (2) | 0.0045 (18) |
N1 | 0.038 (2) | 0.073 (3) | 0.031 (2) | −0.0104 (19) | 0.0017 (17) | 0.0060 (18) |
O1 | 0.045 (2) | 0.089 (3) | 0.045 (2) | −0.0127 (18) | −0.0014 (16) | 0.0090 (17) |
C1 | 0.041 (3) | 0.043 (2) | 0.036 (3) | 0.009 (2) | 0.010 (2) | 0.010 (2) |
C6 | 0.043 (3) | 0.054 (3) | 0.034 (2) | 0.004 (2) | −0.003 (2) | 0.004 (2) |
C7 | 0.043 (3) | 0.047 (3) | 0.030 (2) | 0.003 (2) | 0.003 (2) | 0.0037 (19) |
C2 | 0.039 (3) | 0.050 (3) | 0.043 (3) | −0.004 (2) | 0.001 (2) | 0.001 (2) |
C3 | 0.043 (3) | 0.055 (3) | 0.030 (2) | 0.000 (2) | −0.001 (2) | 0.000 (2) |
C8 | 0.046 (3) | 0.038 (2) | 0.039 (3) | 0.005 (2) | 0.006 (2) | 0.0065 (19) |
C5 | 0.032 (2) | 0.052 (3) | 0.039 (3) | −0.003 (2) | 0.000 (2) | 0.003 (2) |
C14 | 0.054 (3) | 0.049 (3) | 0.044 (3) | −0.007 (2) | 0.007 (2) | 0.005 (2) |
C13 | 0.073 (4) | 0.067 (3) | 0.047 (3) | −0.005 (3) | 0.018 (3) | 0.014 (3) |
C10 | 0.046 (3) | 0.068 (3) | 0.038 (3) | −0.002 (2) | 0.005 (2) | 0.008 (2) |
C11 | 0.059 (3) | 0.093 (4) | 0.046 (3) | 0.001 (3) | −0.010 (3) | 0.008 (3) |
C12 | 0.095 (5) | 0.079 (4) | 0.031 (3) | 0.008 (3) | −0.001 (3) | 0.013 (3) |
Br1—C1 | 1.903 (4) | C7—H7A | 0.9700 |
C4—N1 | 1.365 (5) | C7—H7B | 0.9700 |
C4—C3 | 1.390 (6) | C2—C3 | 1.381 (6) |
C4—C5 | 1.395 (6) | C2—H2 | 0.9300 |
C9—C14 | 1.379 (6) | C3—H3 | 0.9300 |
C9—C10 | 1.384 (6) | C5—H5 | 0.9300 |
C9—C8 | 1.483 (6) | C14—C13 | 1.371 (6) |
N1—C7 | 1.438 (5) | C14—H14 | 0.9300 |
N1—H1 | 0.8600 | C13—C12 | 1.363 (7) |
O1—C8 | 1.214 (5) | C13—H13 | 0.9300 |
C1—C2 | 1.367 (6) | C10—C11 | 1.374 (6) |
C1—C6 | 1.376 (6) | C10—H10 | 0.9300 |
C6—C5 | 1.364 (6) | C11—C12 | 1.377 (7) |
C6—H6 | 0.9300 | C11—H11 | 0.9300 |
C7—C8 | 1.496 (6) | C12—H12 | 0.9300 |
N1—C4—C3 | 123.3 (4) | C2—C3—C4 | 121.2 (4) |
N1—C4—C5 | 119.4 (4) | C2—C3—H3 | 119.4 |
C3—C4—C5 | 117.3 (4) | C4—C3—H3 | 119.4 |
C14—C9—C10 | 118.4 (4) | O1—C8—C9 | 121.5 (4) |
C14—C9—C8 | 118.8 (4) | O1—C8—C7 | 120.2 (4) |
C10—C9—C8 | 122.8 (4) | C9—C8—C7 | 118.3 (4) |
C4—N1—C7 | 123.4 (3) | C6—C5—C4 | 121.4 (4) |
C4—N1—H1 | 118.3 | C6—C5—H5 | 119.3 |
C7—N1—H1 | 118.3 | C4—C5—H5 | 119.3 |
C2—C1—C6 | 120.1 (4) | C13—C14—C9 | 120.6 (4) |
C2—C1—Br1 | 120.3 (3) | C13—C14—H14 | 119.7 |
C6—C1—Br1 | 119.6 (3) | C9—C14—H14 | 119.7 |
C5—C6—C1 | 120.1 (4) | C12—C13—C14 | 120.7 (5) |
C5—C6—H6 | 119.9 | C12—C13—H13 | 119.7 |
C1—C6—H6 | 119.9 | C14—C13—H13 | 119.7 |
N1—C7—C8 | 111.1 (3) | C11—C10—C9 | 120.7 (4) |
N1—C7—H7A | 109.4 | C11—C10—H10 | 119.6 |
C8—C7—H7A | 109.4 | C9—C10—H10 | 119.6 |
N1—C7—H7B | 109.4 | C10—C11—C12 | 119.9 (5) |
C8—C7—H7B | 109.4 | C10—C11—H11 | 120.0 |
H7A—C7—H7B | 108.0 | C12—C11—H11 | 120.0 |
C1—C2—C3 | 119.8 (4) | C13—C12—C11 | 119.6 (5) |
C1—C2—H2 | 120.1 | C13—C12—H12 | 120.2 |
C3—C2—H2 | 120.1 | C11—C12—H12 | 120.2 |
Experimental details
Crystal data | |
Chemical formula | C14H12BrNO |
Mr | 290.15 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.7609 (9), 7.5689 (11), 14.227 (2) |
α, β, γ (°) | 99.374 (2), 91.216 (2), 96.778 (2) |
V (Å3) | 607.27 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 3.37 |
Crystal size (mm) | 0.40 × 0.06 × 0.02 × 0.04 (radius) |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5884, 2133, 1748 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.100, 1.15 |
No. of reflections | 2133 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.40 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1996) in the suite WinGX (Farrugia, 1999), PLATON (Spek, 1990).
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The title compound, (I), provides the required starting material for the synthesis of 2,5-diphenyl-3,4-bis(p-bromoanilino)furan in good yield (Bryce et al., 1965). It is interesting to note that the atoms C4—N1—C7—C8—C9 (Fig. 1) possess an all trans conformation and the N1—H1···O1 intermolecular hydrogen bond which could be expected to form dimers across the centre of symmetry is absent (Fig. 2). The bond lengths and angles are as expected.