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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2761
https://doi.org/10.1107/S160053680904104X

2-Bromo-3-nitro­benzaldehyde

Vijay P. Singh,a Harkesh B. Singha* and Ray J. Butcherb

aDepartment of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India, and bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: chhbsia@chem.iitb.ac.in

(Received 26 September 2009; accepted 8 October 2009; online 17 October 2009)

The title compound, C7H4BrNO3, was isolated as a by-product while attempting to prepare a diselenide. There is a close intra­molecular Br⋯O contact [2.984 (2) Å]. The mol­ecules form loosely associated dimers held together by weak inter­molecular Br⋯O inter­actions with the nitro O atoms [Br⋯O = 3.179 (3) Å]. As a result of these inter­actions, there is also a close Br⋯Br inter­molecular contact [3.8714 (6) Å]. In addition, there are weak inter­molecular C—H⋯O inter­actions. The combination of these inter­actions produces sheets which propagate in the (210) and ([\overline{2}]10) directions perpendicular to c.

Related literature

For the preparation and reactivity of the title compound, see: Rahman & Scrowston (1984[Rahman, L. K. A. & Scrowston, R. M. (1984). J. Chem. Soc. Perkin Trans. 1, pp. 385-390.]); Sienkowska et al. (2000[Sienkowska, M., Benin, V. & Kaszynski, P. (2000). Tetrahedron, 56, 165-173.]); Wirth & Fragale (1997[Wirth, T. & Fragale, G. (1997). Chem. Eur. J. 3, 1894-1902.]). For bond-length data, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For intramolecular chalcogen interactions, see: Singh et al. (2009[Singh, V. P., Singh, H. B. & Butcher, R. J. (2009). In preparation.]). For intermolecular Br⋯O interactions, see: Jones & Lozano (2004[Jones, P. G. & Lozano, V. (2004). Acta Cryst. C60, o876-o878.]); Kruszynski (2007[Kruszynski, R. (2007). Acta Cryst. C63, o389-o391.]); Pedireddi et al. (1992[Pedireddi, V. R., Sarma, J. A. R. P. & Desiraju, G. R. (1992). J. Chem. Soc. Perkin Trans. 2, pp. 311-320.]); Xie et al. (2009[Xie, M., Deng, C., Zheng, J. & Zhu, Y. (2009). Acta Cryst. E65, o1980.]).

[Scheme 1]

Experimental

Crystal data

  • C7H4BrNO3

  • Mr = 230.02

  • Monoclinic, P 21 /c

  • a = 8.1578 (8) Å

  • b = 6.3079 (5) Å

  • c = 15.0537 (11) Å

  • β = 91.603 (8)°

  • V = 774.34 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 5.27 mm−1

  • T = 296 K

  • 0.27 × 0.18 × 0.09 mm
Data collection

  • Oxford Diffraction Gemini R diffractometer

  • Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlisPro. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.330, Tmax = 0.649

  • 5208 measured reflections

  • 2120 independent reflections

  • 1308 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.079

  • S = 0.97

  • 2120 reflections

  • 109 parameters

  • H-atom parameters constrained

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C6—H6⋯O1i 0.93 2.55 3.354 (4) 145
C7—H7⋯O3ii 0.93 2.62 3.534 (4) 168
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlisPro (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlisPro. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680904104X/om2283sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904104X/om2283Isup2.hkl

checkCIF report


Comment top

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

The title compound 1, C7H4NO3Br, was isolated as a by-product while attempting to prepare diselenide 2 by reacting 2-bromo-3-nitrobenzylalcohol with disodium diselenide (Wirth & Fragale, 1997) as shown in scheme 1. Presumably, the formation of 1 takes place during column chromatography on silica gel where the alcohol function is oxidized to the aldehyde function. The preparation (but not the structure) of the title compound by different routes has been previously reported (Rahman & Scrowston, 1984; Sienkowska et al., 2000). In 1, with two withdrawing ortho groups present, the 2-position is highly susceptible to nucleophilic substitution by Na2Se2, Na2Te2, Na2Se to afford a series of novel chalcogen compounds (Singh et al. 2009). In this paper we report the structure of the precursor.

The bond lengths and angles in the title compound are within the normal ranges for related compounds (Allen et al., 2002). When chalcogens (Se, Te) are present in the 2-position in place of bromine there is an intramolecular chalcogen (Se/Te···oxygen(aldehyde/nitro)) interaction (Singh et al. 2009). It was of interest to see whether the bromo analog will interact intramolecularly with the nitro/aldehyde donor groups. There is a close intramolecular Br···O contact of 2.984 (2) Å. The molecules form loosely associated dimers held together by weak intermolecular Br···O interactions with the nitro O atoms (Br···O 3.179 (3) Å, see Figure 1). Similar interactions have been previously reported (Jones & Lozano, 2004; Kruszynski, 2007; Pedireddi et al., 1992; Xie et al., 2009). As a result of these interactions there is also a close Br···Br intermolecular contact (3.8714 (6) Å) as has been commonly observed [42 examples found in a search of the Cambridge Structural Database (Allen, 2002)]. In addition there are weak intermolecular C—H···O interactions. Of the intermolecular interactions, only that between O3 and the aldehyde H is out of plane. As a result of this out-of-plane interaction the nitro group is twisted by 43.6 (4)° from the plane of the aromatic ring. The combination of these interactions produces sheets which propagate in the (2 1 0) and (-2 1 0) directions perpendicular to c as shown in Figure 2.

Related literature top

For related literature on the preparation and reactivity of the title compound, see: Rahman & Scrowston (1984); Sienkowska et al. (2000); Wirth & Fragale (1997).

For related literature, see: Allen (2002); Jones & Lozano (2004); Kruszynski (2007); Pedireddi et al. (1992); Singh et al. (2009); Xie et al. (2009).

Experimental top

The title compound 1, C7H4NO3Br, was isolated as a by-product while attempting to prepare diselenide 2 by reacting 2-bromo-3-nitrobenzylalcohol with disodium diselenide (Wirth & Fragale, 1997). Presumably, the formation of 1 takes place during column chromatography on silica gel where the alcohol function is oxidized to the aldehyde function. It has been prepared previously by a different routes (Rahman & Scrowston, 1984; Sienkowska et al. 2000).

Crystal suitable for X-ray diffraction were obtained from CH2Cl2/ethyl acetate.

Structure description top

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

The title compound 1, C7H4NO3Br, was isolated as a by-product while attempting to prepare diselenide 2 by reacting 2-bromo-3-nitrobenzylalcohol with disodium diselenide (Wirth & Fragale, 1997) as shown in scheme 1. Presumably, the formation of 1 takes place during column chromatography on silica gel where the alcohol function is oxidized to the aldehyde function. The preparation (but not the structure) of the title compound by different routes has been previously reported (Rahman & Scrowston, 1984; Sienkowska et al., 2000). In 1, with two withdrawing ortho groups present, the 2-position is highly susceptible to nucleophilic substitution by Na2Se2, Na2Te2, Na2Se to afford a series of novel chalcogen compounds (Singh et al. 2009). In this paper we report the structure of the precursor.

The bond lengths and angles in the title compound are within the normal ranges for related compounds (Allen et al., 2002). When chalcogens (Se, Te) are present in the 2-position in place of bromine there is an intramolecular chalcogen (Se/Te···oxygen(aldehyde/nitro)) interaction (Singh et al. 2009). It was of interest to see whether the bromo analog will interact intramolecularly with the nitro/aldehyde donor groups. There is a close intramolecular Br···O contact of 2.984 (2) Å. The molecules form loosely associated dimers held together by weak intermolecular Br···O interactions with the nitro O atoms (Br···O 3.179 (3) Å, see Figure 1). Similar interactions have been previously reported (Jones & Lozano, 2004; Kruszynski, 2007; Pedireddi et al., 1992; Xie et al., 2009). As a result of these interactions there is also a close Br···Br intermolecular contact (3.8714 (6) Å) as has been commonly observed [42 examples found in a search of the Cambridge Structural Database (Allen, 2002)]. In addition there are weak intermolecular C—H···O interactions. Of the intermolecular interactions, only that between O3 and the aldehyde H is out of plane. As a result of this out-of-plane interaction the nitro group is twisted by 43.6 (4)° from the plane of the aromatic ring. The combination of these interactions produces sheets which propagate in the (2 1 0) and (-2 1 0) directions perpendicular to c as shown in Figure 2.

For related literature on the preparation and reactivity of the title compound, see: Rahman & Scrowston (1984); Sienkowska et al. (2000); Wirth & Fragale (1997).

For related literature, see: Allen (2002); Jones & Lozano (2004); Kruszynski (2007); Pedireddi et al. (1992); Singh et al. (2009); Xie et al. (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of C7H4NO3Br the showing the Br···O intra- and intermolecular interactions (as dashed lines) forming loosely associated dimers. The atom numbering scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The molecular packing for C7H4NO3Br viewed down the c axis showing the sheets of associated molecules in the (2 1 0) and (-2 1 0) directions. The secondary interactions are shown by dashed lines.
[Figure 3] Fig. 3. The formation of the title compound.
2-Bromo-3-nitrobenzaldehyde top
Crystal data top
C7H4BrNO3F(000) = 448
Mr = 230.02Dx = 1.973 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.1578 (8) ÅCell parameters from 2069 reflections
b = 6.3079 (5) Åθ = 4.7–30.5°
c = 15.0537 (11) ŵ = 5.27 mm−1
β = 91.603 (8)°T = 296 K
V = 774.34 (11) Å3Rectangular plate, orange
Z = 40.27 × 0.18 × 0.09 mm
Data collection top
Oxford Diffraction Gemini R
diffractometer		2120 independent reflections
Radiation source: Enhance (Mo) X-ray Source1308 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 10.5081 pixels mm-1θmax = 30.6°, θmin = 4.9°
ω scansh = −11→10
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		k = −8→7
Tmin = 0.330, Tmax = 0.649l = −21→11
5208 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0388P)2]
where P = (Fo2 + 2Fc2)/3
2120 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.77 e Å−3
0 restraintsΔρmin = −0.45 e Å−3
Crystal data top
C7H4BrNO3V = 774.34 (11) Å3
Mr = 230.02Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1578 (8) ŵ = 5.27 mm−1
b = 6.3079 (5) ÅT = 296 K
c = 15.0537 (11) Å0.27 × 0.18 × 0.09 mm
β = 91.603 (8)°
Data collection top
Oxford Diffraction Gemini R
diffractometer		2120 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		1308 reflections with I > 2σ(I)
Tmin = 0.330, Tmax = 0.649Rint = 0.031
5208 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 0.97Δρmax = 0.77 e Å−3
2120 reflectionsΔρmin = −0.45 e Å−3
109 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.14664 (4)0.22483 (5)0.465488 (18)0.04777 (13)
O10.4218 (3)0.7906 (3)0.39513 (14)0.0541 (5)
O2−0.0180 (3)0.1829 (4)0.63917 (17)0.0744 (7)
O30.1725 (4)0.1401 (5)0.73881 (17)0.0868 (8)
N10.1141 (4)0.2271 (4)0.67396 (17)0.0505 (7)
C10.3125 (3)0.6054 (4)0.51753 (16)0.0348 (6)
C20.2254 (3)0.4311 (4)0.54696 (16)0.0328 (5)
C30.2073 (3)0.4060 (4)0.63756 (17)0.0370 (6)
C40.2767 (3)0.5454 (5)0.69788 (18)0.0470 (7)
H40.26530.52270.75840.056*
C50.3621 (4)0.7169 (5)0.6692 (2)0.0508 (8)
H50.40880.81190.70980.061*
C60.3785 (4)0.7478 (4)0.5787 (2)0.0434 (7)
H60.43480.86600.55870.052*
C70.3397 (4)0.6456 (5)0.42181 (18)0.0443 (7)
H70.29100.55450.38030.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0561 (2)0.04590 (19)0.04115 (18)−0.00979 (14)−0.00130 (13)−0.00726 (13)
O10.0632 (13)0.0526 (13)0.0468 (12)−0.0092 (11)0.0069 (10)0.0147 (10)
O20.0641 (16)0.0862 (18)0.0735 (17)−0.0285 (14)0.0124 (14)0.0052 (14)
O30.119 (2)0.0817 (19)0.0591 (15)−0.0035 (17)−0.0007 (15)0.0315 (15)
N10.0631 (18)0.0518 (16)0.0375 (13)−0.0010 (13)0.0145 (13)0.0043 (12)
C10.0361 (14)0.0354 (14)0.0329 (13)0.0038 (11)0.0010 (11)−0.0006 (11)
C20.0306 (13)0.0351 (13)0.0325 (13)0.0046 (11)−0.0014 (10)−0.0021 (11)
C30.0363 (14)0.0407 (14)0.0341 (14)0.0034 (12)0.0039 (11)0.0007 (11)
C40.0520 (18)0.060 (2)0.0291 (13)0.0078 (15)0.0055 (13)−0.0049 (13)
C50.0549 (19)0.0558 (18)0.0413 (16)−0.0046 (15)−0.0044 (14)−0.0159 (14)
C60.0449 (17)0.0392 (17)0.0460 (16)−0.0018 (12)0.0017 (13)−0.0033 (13)
C70.0486 (17)0.0447 (16)0.0394 (15)0.0044 (14)−0.0053 (13)0.0003 (13)
Geometric parameters (Å, º) top
Br1—C21.889 (2)C1—C71.486 (4)
Br1—O22.984 (2)C2—C31.385 (3)
Br1—Br1i3.8714 (6)C3—C41.375 (4)
O1—C71.209 (3)C4—C51.363 (4)
O2—N11.217 (4)C4—H40.9300
O2—Br1i3.179 (3)C5—C61.387 (4)
O3—N11.206 (4)C5—H50.9300
N1—C31.475 (4)C6—H60.9300
C1—C61.384 (4)C7—H70.9300
C1—C21.388 (3)
C2—Br1—O269.23 (9)C4—C3—C2121.6 (2)
C2—Br1—Br1i122.15 (8)C4—C3—N1116.8 (2)
O2—Br1—Br1i53.36 (5)C2—C3—N1121.6 (2)
N1—O2—Br186.66 (16)C5—C4—C3120.2 (3)
N1—O2—Br1i132.4 (2)C5—C4—H4119.9
Br1—O2—Br1i77.75 (6)C3—C4—H4119.9
O3—N1—O2124.7 (3)C4—C5—C6119.1 (3)
O3—N1—C3116.9 (3)C4—C5—H5120.4
O2—N1—C3118.4 (3)C6—C5—H5120.4
C6—C1—C2119.6 (2)C1—C6—C5121.1 (3)
C6—C1—C7117.9 (2)C1—C6—H6119.5
C2—C1—C7122.4 (2)C5—C6—H6119.5
C3—C2—C1118.3 (2)O1—C7—C1123.4 (3)
C3—C2—Br1121.12 (19)O1—C7—H7118.3
C1—C2—Br1120.42 (18)C1—C7—H7118.3
C2—Br1—O2—N1−37.66 (19)Br1—C2—C3—C4174.2 (2)
Br1i—Br1—O2—N1134.7 (2)C1—C2—C3—N1178.9 (2)
C2—Br1—O2—Br1i−172.41 (10)Br1—C2—C3—N1−5.2 (3)
Br1—O2—N1—O3−137.5 (3)O3—N1—C3—C4−41.7 (4)
Br1i—O2—N1—O3−67.4 (4)O2—N1—C3—C4135.4 (3)
Br1—O2—N1—C345.6 (2)O3—N1—C3—C2137.7 (3)
Br1i—O2—N1—C3115.6 (3)O2—N1—C3—C2−45.1 (4)
C6—C1—C2—C30.2 (4)C2—C3—C4—C51.8 (4)
C7—C1—C2—C3179.5 (2)N1—C3—C4—C5−178.8 (3)
C6—C1—C2—Br1−175.8 (2)C3—C4—C5—C6−0.3 (4)
C7—C1—C2—Br13.6 (3)C2—C1—C6—C51.3 (4)
O2—Br1—C2—C319.93 (19)C7—C1—C6—C5−178.1 (3)
Br1i—Br1—C2—C312.7 (2)C4—C5—C6—C1−1.3 (5)
O2—Br1—C2—C1−164.3 (2)C6—C1—C7—O13.1 (4)
Br1i—Br1—C2—C1−171.45 (16)C2—C1—C7—O1−176.3 (3)
C1—C2—C3—C4−1.7 (4)
Symmetry code: (i) −x, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1ii0.932.553.354 (4)145
C7—H7···O3iii0.932.623.534 (4)168
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC7H4BrNO3
Mr230.02
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.1578 (8), 6.3079 (5), 15.0537 (11)
β (°) 91.603 (8)
V (Å3)774.34 (11)
Z4
Radiation typeMo Kα
µ (mm−1)5.27
Crystal size (mm)0.27 × 0.18 × 0.09
Data collection
DiffractometerOxford Diffraction Gemini R
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.330, 0.649
No. of measured, independent and
observed [I > 2σ(I)] reflections		5208, 2120, 1308
Rint0.031
(sin θ/λ)max (Å−1)0.716
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.079, 0.97
No. of reflections2120
No. of parameters109
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.77, −0.45

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.553.354 (4)145.1
C7—H7···O3ii0.932.623.534 (4)167.7
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+1/2, z−1/2.
 

Acknowledgements

HBS is grateful to the Department of Science and Technology (DST) for the award of a Ramanna Fellowship. VPS is grateful to IIT Bombay for the award of a teaching assistantship. RJB wishes to acknowledge the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2761
https://doi.org/10.1107/S160053680904104X
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