organic compounds
The synthesis and structure of a brominated derivative of 2'-aminoacetophenone, C8H8BrNO, is described. The conformation observed in the solid state was found to be the same as that previously determined by NMR studies.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100839X/tk6021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680100839X/tk6021Isup2.hkl |
CCDC reference: 170310
Computing details top
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXL97.
2'-amino-5'-bromoacetophenone top
Crystal data top
C8H8BrNO | Dx = 1.742 Mg m−3 |
Mr = 214.06 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 3623 reflections |
a = 21.9206 (6) Å | θ = 2–25° |
b = 7.3583 (2) Å | µ = 4.97 mm−1 |
c = 5.0596 (2) Å | T = 291 K |
V = 816.11 (4) Å3 | Prism, yellow |
Z = 4 | 0.42 × 0.22 × 0.18 mm |
F(000) = 424 |
Data collection top
Siemens SMART diffractometer | 1347 independent reflections |
Radiation source: fine-focus sealed tube | 1278 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Area detector ω scans | θmax = 25.6°, θmin = 1.9° |
Absorption correction: multi-scan Blessing, 1995 | h = −26→23 |
Tmin = 0.229, Tmax = 0.468 | k = −8→8 |
4318 measured reflections | l = −6→4 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.061 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2) + (0.0374P)2 + 0.0296P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.007 |
1347 reflections | Δρmax = 0.18 e Å−3 |
124 parameters | Δρmin = −0.41 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.059 (13) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.255652 (11) | 0.64206 (4) | 0.59019 (16) | 0.06011 (13) | |
O | 0.45866 (10) | 0.0319 (3) | 0.3267 (5) | 0.0659 (6) | |
N | 0.47678 (12) | 0.3284 (3) | 0.0306 (5) | 0.0576 (8) | |
H0A | 0.4943 | 0.3948 | −0.0869 | 0.069* | |
H0B | 0.4915 | 0.2234 | 0.0695 | 0.069* | |
C1 | 0.39591 (11) | 0.2922 (3) | 0.3620 (5) | 0.0366 (5) | |
C2 | 0.42563 (12) | 0.3895 (3) | 0.1552 (5) | 0.0410 (6) | |
C3 | 0.40223 (12) | 0.5615 (3) | 0.0887 (8) | 0.0495 (6) | |
H3 | 0.4216 | 0.6283 | −0.0429 | 0.059* | |
C4 | 0.35225 (15) | 0.6345 (3) | 0.2094 (7) | 0.0509 (7) | |
H4 | 0.3372 | 0.7468 | 0.1562 | 0.061* | |
C5 | 0.32405 (11) | 0.5389 (3) | 0.4135 (5) | 0.0405 (6) | |
C6 | 0.34538 (12) | 0.3710 (3) | 0.4887 (5) | 0.0394 (6) | |
H6 | 0.3261 | 0.3087 | 0.6252 | 0.047* | |
C7 | 0.41662 (13) | 0.1078 (3) | 0.4410 (6) | 0.0434 (6) | |
C8 | 0.38463 (14) | 0.0102 (4) | 0.6626 (6) | 0.0545 (8) | |
H8A | 0.3994 | −0.1125 | 0.6731 | 0.082* | |
H8B | 0.3415 | 0.0091 | 0.6297 | 0.082* | |
H8C | 0.3926 | 0.0716 | 0.8264 | 0.082* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.05116 (17) | 0.05745 (19) | 0.0717 (2) | 0.01507 (10) | −0.0028 (3) | −0.0056 (2) |
O | 0.0722 (15) | 0.0578 (12) | 0.0676 (15) | 0.0255 (11) | 0.0149 (12) | 0.0134 (11) |
N | 0.0557 (14) | 0.0569 (13) | 0.060 (2) | −0.0011 (11) | 0.0167 (12) | 0.0099 (11) |
C1 | 0.0382 (13) | 0.0334 (12) | 0.0383 (13) | −0.0031 (9) | −0.0059 (9) | 0.0020 (10) |
C2 | 0.0442 (13) | 0.0383 (12) | 0.0403 (17) | −0.0058 (10) | −0.0048 (9) | 0.0008 (10) |
C3 | 0.0656 (14) | 0.0394 (12) | 0.0436 (13) | −0.0065 (10) | −0.004 (2) | 0.0119 (16) |
C4 | 0.068 (2) | 0.0339 (14) | 0.0504 (16) | 0.0036 (11) | −0.0113 (14) | 0.0024 (11) |
C5 | 0.0415 (13) | 0.0371 (12) | 0.0431 (14) | 0.0019 (10) | −0.0064 (11) | −0.0035 (11) |
C6 | 0.0394 (13) | 0.0361 (13) | 0.0428 (14) | −0.0039 (9) | −0.0032 (10) | 0.0030 (9) |
C7 | 0.0498 (16) | 0.0393 (13) | 0.0410 (15) | 0.0028 (12) | −0.0054 (12) | 0.0023 (12) |
C8 | 0.0654 (17) | 0.0376 (13) | 0.061 (2) | 0.0030 (13) | 0.0046 (13) | 0.0118 (12) |
Geometric parameters (Å, º) top
Br1—C5 | 1.903 (3) | C3—H3 | 0.9300 |
O—C7 | 1.223 (3) | C4—C5 | 1.394 (4) |
N—C2 | 1.363 (4) | C4—H4 | 0.9300 |
N—H0A | 0.8600 | C5—C6 | 1.375 (3) |
N—H0B | 0.8600 | C6—H6 | 0.9300 |
C1—C6 | 1.405 (3) | C7—C8 | 1.505 (4) |
C1—C2 | 1.425 (3) | C8—H8A | 0.9600 |
C1—C7 | 1.485 (3) | C8—H8B | 0.9600 |
C2—C3 | 1.407 (3) | C8—H8C | 0.9600 |
C3—C4 | 1.364 (4) | ||
C2—N—H0A | 120.0 | C6—C5—C4 | 120.5 (3) |
C2—N—H0B | 120.0 | C6—C5—Br1 | 119.7 (2) |
H0A—N—H0B | 120.0 | C4—C5—Br1 | 119.73 (19) |
C6—C1—C2 | 119.2 (2) | C5—C6—C1 | 120.8 (2) |
C6—C1—C7 | 119.7 (2) | C5—C6—H6 | 119.6 |
C2—C1—C7 | 121.1 (2) | C1—C6—H6 | 119.6 |
N—C2—C3 | 119.1 (3) | O—C7—C1 | 121.4 (3) |
N—C2—C1 | 123.4 (2) | O—C7—C8 | 119.0 (2) |
C3—C2—C1 | 117.4 (3) | C1—C7—C8 | 119.6 (2) |
C4—C3—C2 | 122.7 (3) | C7—C8—H8A | 109.5 |
C4—C3—H3 | 118.7 | C7—C8—H8B | 109.5 |
C2—C3—H3 | 118.7 | H8A—C8—H8B | 109.5 |
C3—C4—C5 | 119.3 (2) | C7—C8—H8C | 109.5 |
C3—C4—H4 | 120.4 | H8A—C8—H8C | 109.5 |
C5—C4—H4 | 120.4 | H8B—C8—H8C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H0b···O | 0.86 | 2.05 | 2.676 (3) | 129 |
N—H0b···Oi | 0.86 | 2.50 | 3.177 (3) | 137 |
Symmetry code: (i) −x+1, −y, z−1/2. |