2'-Amino-5'-bromo­aceto­phenone

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.

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


 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

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Computing details

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

Crystal data

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) Å^3	Prism, yellow
Z = 4	0.42 × 0.22 × 0.18 mm
F(000) = 424

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.061	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2) + (0.0374P)^2 + 0.0296P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O^i	0.86	2.50	3.177 (3)	137

Symmetry code: (i) −x+1, −y, z−1/2.