2'-Amino-3',5'-di­bromo­aceto­phenone

The synthesis and structure of a di-brominated derivative of 2'-amino­aceto­phenone, C₈H₇Br₂NO, is described. The conformation observed in the solid state was found to be the same as that previously proposed for solution conformations of related compounds.

Key indicators

• Single-crystal X-ray study
• T = 203 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.023
• wR factor = 0.061
• Data-to-parameter ratio = 14.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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      0.499
          Tmax scaled      0.106 Tmin scaled      0.072

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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-3',5'-dibromoacetophenone

Crystal data

C8H7Br2NO	F(000) = 560
Mr = 292.97	Dx = 2.165 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.147 (6) Å	Cell parameters from 4466 reflections
b = 10.138 (7) Å	θ = 2–25°
c = 9.699 (8) Å	µ = 8.97 mm^−1
β = 92.02 (4)°	T = 203 K
V = 898.9 (11) Å^3	Tablet, yellow
Z = 4	0.35 × 0.25 × 0.25 mm

Data collection

Siemens SMART diffractometer	1582 independent reflections
Radiation source: fine-focus sealed tube	1444 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Area detector ω scans	θmax = 25°, θmin = 2.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −11→11
Tmin = 0.145, Tmax = 0.213	k = 0→12
5582 measured reflections	l = 0→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.061	H-atom parameters constrained
S = 1.06	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2) + (0.0424P)^2] where P = (Fo^2 + 2Fc^2)/3
1841 reflections	(Δ/σ)max = 0.004
130 parameters	Δρmax = 0.94 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.35068 (3)	0.11023 (3)	0.51096 (3)	0.02669 (12)
Br2	−0.01602 (3)	0.44704 (3)	0.19031 (3)	0.02803 (12)
N	0.4348 (3)	0.3679 (2)	0.6575 (2)	0.0256 (5)
H0A	0.4686	0.2889	0.6729	0.031*
H0B	0.4670	0.4338	0.7073	0.031*
O	0.4142 (2)	0.62634 (19)	0.7003 (2)	0.0319 (5)
C1	0.2740 (3)	0.5160 (3)	0.5255 (3)	0.0186 (5)
C2	0.3325 (3)	0.3883 (3)	0.5562 (3)	0.0186 (5)
C3	0.2783 (3)	0.2829 (3)	0.4738 (3)	0.0193 (5)
C4	0.1775 (3)	0.2984 (3)	0.3667 (3)	0.0213 (6)
H4	0.1458	0.2255	0.3137	0.026*
C5	0.1233 (3)	0.4244 (3)	0.3381 (3)	0.0205 (6)
C6	0.1701 (3)	0.5311 (3)	0.4164 (3)	0.0204 (6)
H6	0.1318	0.6153	0.3964	0.025*
C7	0.3213 (3)	0.6334 (3)	0.6057 (3)	0.0217 (6)
C8	0.2545 (3)	0.7662 (3)	0.5711 (3)	0.0289 (7)
H8A	0.2928	0.8318	0.6357	0.043*
H8B	0.1490	0.7611	0.5774	0.043*
H8C	0.2788	0.7910	0.4781	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.03645 (19)	0.01505 (18)	0.02804 (18)	0.00468 (11)	−0.00628 (13)	0.00120 (10)
Br2	0.03017 (19)	0.0288 (2)	0.02401 (18)	0.00073 (11)	−0.01479 (12)	0.00008 (11)
N	0.0346 (13)	0.0180 (12)	0.0232 (12)	0.0024 (10)	−0.0132 (10)	−0.0005 (9)
O	0.0413 (13)	0.0228 (11)	0.0302 (11)	−0.0009 (9)	−0.0189 (10)	−0.0035 (9)
C1	0.0209 (13)	0.0166 (13)	0.0181 (13)	−0.0015 (10)	−0.0025 (10)	0.0009 (10)
C2	0.0202 (13)	0.0176 (14)	0.0178 (13)	0.0000 (10)	−0.0023 (11)	0.0020 (10)
C3	0.0244 (13)	0.0153 (13)	0.0182 (13)	0.0024 (10)	−0.0015 (10)	0.0009 (10)
C4	0.0249 (13)	0.0168 (14)	0.0218 (14)	−0.0018 (11)	−0.0020 (11)	−0.0042 (11)
C5	0.0227 (14)	0.0227 (14)	0.0156 (13)	−0.0001 (11)	−0.0046 (11)	0.0009 (11)
C6	0.0258 (14)	0.0156 (13)	0.0195 (13)	0.0002 (11)	−0.0027 (11)	0.0034 (10)
C7	0.0260 (14)	0.0164 (13)	0.0223 (13)	−0.0021 (11)	−0.0053 (11)	0.0023 (11)
C8	0.0363 (16)	0.0168 (14)	0.0327 (16)	−0.0005 (12)	−0.0133 (13)	−0.0020 (12)

Geometric parameters (Å, º)

Br1—C3	1.901 (3)	C3—C4	1.373 (4)
Br2—C5	1.898 (3)	C4—C5	1.395 (4)
N—C2	1.348 (4)	C4—H4	0.9400
N—H0A	0.8700	C5—C6	1.381 (4)
N—H0B	0.8700	C6—H6	0.9400
O—C7	1.231 (4)	C7—C8	1.512 (4)
C1—C6	1.406 (4)	C8—H8A	0.9700
C1—C2	1.428 (4)	C8—H8B	0.9700
C1—C7	1.478 (4)	C8—H8C	0.9700
C2—C3	1.414 (4)
C2—N—H0A	120.0	C6—C5—C4	120.5 (2)
C2—N—H0B	120.0	C6—C5—Br2	120.5 (2)
H0A—N—H0B	120.0	C4—C5—Br2	119.0 (2)
C6—C1—C2	119.6 (2)	C5—C6—C1	121.1 (3)
C6—C1—C7	119.1 (2)	C5—C6—H6	119.4
C2—C1—C7	121.3 (2)	C1—C6—H6	119.4
N—C2—C3	121.1 (2)	O—C7—C1	121.8 (3)
N—C2—C1	122.4 (2)	O—C7—C8	118.7 (2)
C3—C2—C1	116.5 (2)	C1—C7—C8	119.5 (2)
C4—C3—C2	123.6 (2)	C7—C8—H8A	109.5
C4—C3—Br1	118.0 (2)	C7—C8—H8B	109.5
C2—C3—Br1	118.41 (19)	H8A—C8—H8B	109.5
C3—C4—C5	118.7 (2)	C7—C8—H8C	109.5
C3—C4—H4	120.7	H8A—C8—H8C	109.5
C5—C4—H4	120.7	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	0.87	2.01	2.660 (4)	131
N—H0a···O^i	0.87	2.30	3.110 (3)	155
N—H0a···Br1	0.87	2.61	3.059 (3)	114

Symmetry code: (i) −x+1, y−1/2, −z+3/2.