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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100839X/tk6021sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100839X/tk6021Isup2.hkl
Contains datablock I

CCDC reference: 170310

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.024
  • wR factor = 0.061
  • Data-to-parameter ratio = 10.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N - H0A ? General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.873 Tmax scaled 0.408 Tmin scaled 0.200 REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.60 From the CIF: _reflns_number_total 1347 Count of symmetry unique reflns 858 Completeness (_total/calc) 156.99% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 489 Fraction of Friedel pairs measured 0.570 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

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
C8H8BrNODx = 1.742 Mg m3
Mr = 214.06Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 3623 reflections
a = 21.9206 (6) Åθ = 2–25°
b = 7.3583 (2) ŵ = 4.97 mm1
c = 5.0596 (2) ÅT = 291 K
V = 816.11 (4) Å3Prism, yellow
Z = 40.42 × 0.22 × 0.18 mm
F(000) = 424
Data collection top
Siemens SMART
diffractometer
1347 independent reflections
Radiation source: fine-focus sealed tube1278 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Area detector ω scansθmax = 25.6°, θmin = 1.9°
Absorption correction: multi-scan
Blessing, 1995
h = 2623
Tmin = 0.229, Tmax = 0.468k = 88
4318 measured reflectionsl = 64
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.061Weighting 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 reflectionsΔρmax = 0.18 e Å3
124 parametersΔρmin = 0.41 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.059 (13)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.255652 (11)0.64206 (4)0.59019 (16)0.06011 (13)
O0.45866 (10)0.0319 (3)0.3267 (5)0.0659 (6)
N0.47678 (12)0.3284 (3)0.0306 (5)0.0576 (8)
H0A0.49430.39480.08690.069*
H0B0.49150.22340.06950.069*
C10.39591 (11)0.2922 (3)0.3620 (5)0.0366 (5)
C20.42563 (12)0.3895 (3)0.1552 (5)0.0410 (6)
C30.40223 (12)0.5615 (3)0.0887 (8)0.0495 (6)
H30.42160.62830.04290.059*
C40.35225 (15)0.6345 (3)0.2094 (7)0.0509 (7)
H40.33720.74680.15620.061*
C50.32405 (11)0.5389 (3)0.4135 (5)0.0405 (6)
C60.34538 (12)0.3710 (3)0.4887 (5)0.0394 (6)
H60.32610.30870.62520.047*
C70.41662 (13)0.1078 (3)0.4410 (6)0.0434 (6)
C80.38463 (14)0.0102 (4)0.6626 (6)0.0545 (8)
H8A0.39940.11250.67310.082*
H8B0.34150.00910.62970.082*
H8C0.39260.07160.82640.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.05116 (17)0.05745 (19)0.0717 (2)0.01507 (10)0.0028 (3)0.0056 (2)
O0.0722 (15)0.0578 (12)0.0676 (15)0.0255 (11)0.0149 (12)0.0134 (11)
N0.0557 (14)0.0569 (13)0.060 (2)0.0011 (11)0.0167 (12)0.0099 (11)
C10.0382 (13)0.0334 (12)0.0383 (13)0.0031 (9)0.0059 (9)0.0020 (10)
C20.0442 (13)0.0383 (12)0.0403 (17)0.0058 (10)0.0048 (9)0.0008 (10)
C30.0656 (14)0.0394 (12)0.0436 (13)0.0065 (10)0.004 (2)0.0119 (16)
C40.068 (2)0.0339 (14)0.0504 (16)0.0036 (11)0.0113 (14)0.0024 (11)
C50.0415 (13)0.0371 (12)0.0431 (14)0.0019 (10)0.0064 (11)0.0035 (11)
C60.0394 (13)0.0361 (13)0.0428 (14)0.0039 (9)0.0032 (10)0.0030 (9)
C70.0498 (16)0.0393 (13)0.0410 (15)0.0028 (12)0.0054 (12)0.0023 (12)
C80.0654 (17)0.0376 (13)0.061 (2)0.0030 (13)0.0046 (13)0.0118 (12)
Geometric parameters (Å, º) top
Br1—C51.903 (3)C3—H30.9300
O—C71.223 (3)C4—C51.394 (4)
N—C21.363 (4)C4—H40.9300
N—H0A0.8600C5—C61.375 (3)
N—H0B0.8600C6—H60.9300
C1—C61.405 (3)C7—C81.505 (4)
C1—C21.425 (3)C8—H8A0.9600
C1—C71.485 (3)C8—H8B0.9600
C2—C31.407 (3)C8—H8C0.9600
C3—C41.364 (4)
C2—N—H0A120.0C6—C5—C4120.5 (3)
C2—N—H0B120.0C6—C5—Br1119.7 (2)
H0A—N—H0B120.0C4—C5—Br1119.73 (19)
C6—C1—C2119.2 (2)C5—C6—C1120.8 (2)
C6—C1—C7119.7 (2)C5—C6—H6119.6
C2—C1—C7121.1 (2)C1—C6—H6119.6
N—C2—C3119.1 (3)O—C7—C1121.4 (3)
N—C2—C1123.4 (2)O—C7—C8119.0 (2)
C3—C2—C1117.4 (3)C1—C7—C8119.6 (2)
C4—C3—C2122.7 (3)C7—C8—H8A109.5
C4—C3—H3118.7C7—C8—H8B109.5
C2—C3—H3118.7H8A—C8—H8B109.5
C3—C4—C5119.3 (2)C7—C8—H8C109.5
C3—C4—H4120.4H8A—C8—H8C109.5
C5—C4—H4120.4H8B—C8—H8C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H0b···O0.862.052.676 (3)129
N—H0b···Oi0.862.503.177 (3)137
Symmetry code: (i) x+1, y, z1/2.
 

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