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In the title compound, C13H10BrNO2, the mean plane of the non-H atoms of the central amide C—N—C(=O)—C fragment (r.m.s. deviation = 0.004 Å) forms a dihedral angle of 73.97 (12)° with the hy­droxy-substituted benzene ring and 25.42 (19)° with the bromo-substituted benzene ring. The two aromatic rings are inclined to one another by 80.7 (2)°. In the crystal, mol­ecules are linked by O—H...O and N—H...O hydrogen bonds, forming chains along [010]. The chains are linked by weak C—H...O hydrogen bonds, forming sheets parallel to (100), and enclosing R33(17) and R32(9) ring motifs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814024696/su5019sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536814024696/su5019Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814024696/su5019Isup3.cml
Supplementary material

CCDC reference: 1033535

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.052
  • wR factor = 0.168
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Alert level C PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C4 Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.162 Check
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 1 Note PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) ..... 3 Report
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Comment top

The crystal structure determination of the title compound (I), is part of a study on phenylbenzamides carried out in our research group, and they are synthesized from the reaction of picryl benzoates with 2-hydroxy-aniline. These compounds have received extensive attention because of their antiprotozoal (Ríos Martínez et al., 2014) and anti-microbialactivity (Şener et al., 2000), and as active metabolites of benzoxazoles (Mobinikhaledi et al., 2006). They have also been studied as inhibitors of tyrosine kinases (Capdeville et al., 2002) and inducers of apoptosis in the tumor development process (Olsson et al., 2002). Similar compounds to (I) have been reported in the literature, viz. 4-bromo-N-phenylbenzamide (II) (Fun et al., 2012) and 2-hydroxy-N-benzoylaniline (III) (Hibbert et al., 1998).

The molecular structure of (I) is shown in Fig. 1. The central amide moiety, C8—N1-C7(O1)—C1, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0026 Å) and it forms dihedral angles of 73.97 (12)° with the hydroxy-substituted phenyl ring and 25.42 (19)° with the bromo-substituted benzene ring. The bond lengths and angles within the molecule of (I) are in a good agreement with those found in the related compounds (II) and (III), although the N1-C7 bond length in the central amide segment, is slightly increased in structure (II), [C1-C7= 1.361 (2)Å].

In the crystal of (I), molecules are linked by O-H···O and N-H···O hydrogen bonds of medium-strength and weak C-H···O intermolecular contacts forming sheets parallel to (100) (Table 1 and Fig. 2). The O2-HO2···O1 hydrogen bonds are responsible for crystal growth in the b direction. In this interaction, the hydroxy O2-HO2 group in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O1 of the carbonyl group at (x ,-y-3/2, z-1/2). In turn, the N1-H1···O1 hydrogen bonds and weak C6-H6···O2 interactions, complement crystal growth in the c direction (see Fig. 2). The N1-H1 group of the amide moiety in the molecule at (x ,y, z) acts as hydrogen bond donor to carbonyl atom O1 in the molecule at (x, -y-1/2, z-1/2) and the C6-H6 group in the molecule at (x, y, z) acts as a hydrogen bond donor to atom O2 in the molecule at (x, y+1 ,z). Very likely, these interactions are responsible for the twist of the rings with respect to the central amide moiety. The combination of these interactions generate edge-fused R33(17) and R32(9) ring motifs.

Related literature top

For the antiprotozoal and antimicrobial properties of phenylbenzamides, see: Ríos Martínez et al. (2014); Şener et al. (2000). For active metabolites of benzoxazoles, see: Mobinikhaledi et al. (2006). For studies of phenylbenzamides as inhibitors of tyrosine kinases, see: Capdeville et al. (2002). For studies of phenylbenzamides as inducers of apoptosis in biological processes, see: Olsson et al. (2002). For related structures, see: Fun et al. (2012); Hibbert et al. (1998).

Experimental top

4-bromobenzoate 2,4,6-trinitrophenyl (0.050 g, 0.117 mmol) and 2-hydroxyaniline (0.0254 g) in molar ratio 1:2, were dissolved in 15 mL of toluene and mixed for 6 h under reflux and constant stirring. On completion of the reaction part of the solvent was evaporated and a crystalline black solid was obtained. [m.p.: 454 (1) K].

Refinement top

The H-atoms were positioned in geometrically idealized positions and treated as riding atoms: O—H = 0.82 Å, N—H = 0.86 Å and C—H = 0.93 Å, with Uiso(H) = 1.5Ueq(O) for the hydroxyl H atom and = 1.2Ueq(N, C) for other H atoms.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
The molecular structure of the title compound (I), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Part of the crystal packing of the title compound (I) viewed along the a axis, showing the formation of R33(17) and R32(9) ring motifs within the two-dimensional hydrogen bonded network running parallel to (100). Hydrogen bonds are shown as dashed lines; see Table 1 for details [symmetry codes: (i) x, -y-3/2, z-1/2; (ii) x, -y-1/2, z-1/2; (iii) x, y+1, z].
4-Bromo-N-(2-hydroxyphenyl)benzamide top
Crystal data top
C13H10BrNO2F(000) = 584
Mr = 292.13Dx = 1.588 Mg m3
Monoclinic, P21/cMelting point: 454(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 23.4258 (10) ÅCell parameters from 2490 reflections
b = 5.6473 (1) Åθ = 3.5–26.4°
c = 9.2464 (3) ŵ = 3.35 mm1
β = 93.008 (1)°T = 295 K
V = 1221.54 (7) Å3Block, black
Z = 40.20 × 0.18 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
2490 independent reflections
Radiation source: fine-focus sealed tube1664 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
CCD rotation images, thick slices scansθmax = 26.4°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2929
Tmin = 0.537, Tmax = 0.662k = 76
21458 measured reflectionsl = 1111
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0999P)2 + 0.5651P]
where P = (Fo2 + 2Fc2)/3
2490 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.68 e Å3
Crystal data top
C13H10BrNO2V = 1221.54 (7) Å3
Mr = 292.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 23.4258 (10) ŵ = 3.35 mm1
b = 5.6473 (1) ÅT = 295 K
c = 9.2464 (3) Å0.20 × 0.18 × 0.13 mm
β = 93.008 (1)°
Data collection top
Nonius KappaCCD
diffractometer
2490 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1664 reflections with I > 2σ(I)
Tmin = 0.537, Tmax = 0.662Rint = 0.063
21458 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.168H-atom parameters constrained
S = 0.99Δρmax = 0.61 e Å3
2490 reflectionsΔρmin = 0.68 e Å3
154 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br10.46192 (2)1.31657 (9)0.85256 (8)0.1081 (3)
O10.23094 (11)0.5820 (4)0.8853 (2)0.0546 (6)
C70.24418 (16)0.7116 (6)0.7843 (3)0.0462 (8)
C90.15972 (16)0.4064 (6)0.5411 (4)0.0513 (8)
O20.20914 (13)0.3579 (5)0.4767 (3)0.0700 (8)
HO20.20400.24720.42010.105*
N10.21228 (13)0.7256 (5)0.6607 (3)0.0520 (7)
H10.22350.81680.59330.062*
C10.29740 (16)0.8587 (6)0.7961 (3)0.0490 (8)
C60.30259 (17)1.0664 (6)0.7177 (4)0.0565 (9)
H60.27281.11610.65430.068*
C80.16058 (15)0.5964 (6)0.6357 (3)0.0500 (8)
C50.3522 (2)1.1998 (7)0.7340 (5)0.0675 (11)
H50.35601.33850.68110.081*
C20.34181 (18)0.7886 (7)0.8900 (4)0.0604 (9)
H20.33840.64990.94310.073*
C40.39549 (18)1.1262 (7)0.8281 (5)0.0665 (10)
C130.1110 (2)0.6596 (7)0.7011 (4)0.0683 (11)
H130.11130.78760.76450.082*
C100.11003 (19)0.2786 (8)0.5152 (5)0.0696 (11)
H100.10960.14900.45320.083*
C110.0610 (2)0.3429 (9)0.5812 (5)0.0816 (13)
H110.02750.25660.56350.098*
C30.39140 (18)0.9208 (7)0.9065 (5)0.0704 (11)
H30.42140.87170.96940.084*
C120.06136 (19)0.5340 (10)0.6729 (5)0.0851 (14)
H120.02800.57860.71600.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0702 (4)0.0749 (4)0.1796 (7)0.0166 (2)0.0112 (4)0.0221 (3)
O10.0774 (17)0.0477 (13)0.0385 (12)0.0068 (12)0.0028 (11)0.0028 (10)
C70.062 (2)0.0424 (17)0.0345 (16)0.0026 (15)0.0049 (15)0.0055 (13)
C90.059 (2)0.0450 (18)0.0493 (18)0.0008 (16)0.0007 (16)0.0039 (15)
O20.0772 (19)0.0527 (14)0.0812 (18)0.0004 (13)0.0136 (15)0.0171 (13)
N10.071 (2)0.0511 (15)0.0340 (14)0.0087 (14)0.0044 (13)0.0005 (12)
C10.064 (2)0.0451 (17)0.0381 (16)0.0018 (15)0.0080 (15)0.0056 (14)
C60.072 (2)0.0474 (19)0.0498 (19)0.0078 (17)0.0011 (17)0.0017 (15)
C80.061 (2)0.0484 (18)0.0405 (16)0.0038 (16)0.0009 (15)0.0046 (14)
C50.088 (3)0.048 (2)0.068 (2)0.0111 (19)0.019 (2)0.0034 (17)
C20.069 (2)0.052 (2)0.060 (2)0.0022 (18)0.0012 (19)0.0004 (16)
C40.062 (2)0.056 (2)0.082 (3)0.0074 (19)0.012 (2)0.014 (2)
C130.075 (3)0.075 (3)0.056 (2)0.010 (2)0.0069 (19)0.0066 (18)
C100.072 (3)0.065 (2)0.070 (2)0.011 (2)0.007 (2)0.005 (2)
C110.062 (3)0.099 (4)0.081 (3)0.015 (2)0.013 (2)0.007 (3)
C30.062 (2)0.062 (2)0.086 (3)0.001 (2)0.004 (2)0.013 (2)
C120.056 (3)0.119 (4)0.081 (3)0.010 (3)0.005 (2)0.005 (3)
Geometric parameters (Å, º) top
Br1—C41.895 (4)C8—C131.384 (5)
O1—C71.239 (4)C5—C41.365 (7)
C7—N11.334 (4)C5—H50.9300
C7—C11.497 (5)C2—C31.383 (6)
C9—O21.357 (4)C2—H20.9300
C9—C101.380 (5)C4—C31.374 (6)
C9—C81.384 (5)C13—C121.375 (7)
O2—HO20.8200C13—H130.9300
N1—C81.423 (5)C10—C111.378 (7)
N1—H10.8600C10—H100.9300
C1—C21.377 (5)C11—C121.372 (7)
C1—C61.388 (5)C11—H110.9300
C6—C51.387 (6)C3—H30.9300
C6—H60.9300C12—H120.9300
O1—C7—N1122.0 (3)C1—C2—C3121.1 (4)
O1—C7—C1120.9 (3)C1—C2—H2119.4
N1—C7—C1117.2 (3)C3—C2—H2119.4
O2—C9—C10123.4 (3)C5—C4—C3121.6 (4)
O2—C9—C8116.7 (3)C5—C4—Br1118.7 (3)
C10—C9—C8119.9 (4)C3—C4—Br1119.7 (3)
C9—O2—HO2109.5C12—C13—C8120.3 (4)
C7—N1—C8122.9 (3)C12—C13—H13119.9
C7—N1—H1118.6C8—C13—H13119.9
C8—N1—H1118.6C11—C10—C9120.1 (4)
C2—C1—C6119.2 (3)C11—C10—H10120.0
C2—C1—C7119.0 (3)C9—C10—H10120.0
C6—C1—C7121.7 (3)C12—C11—C10120.2 (4)
C5—C6—C1119.9 (4)C12—C11—H11119.9
C5—C6—H6120.1C10—C11—H11119.9
C1—C6—H6120.1C4—C3—C2118.6 (4)
C9—C8—C13119.4 (4)C4—C3—H3120.7
C9—C8—N1119.0 (3)C2—C3—H3120.7
C13—C8—N1121.5 (3)C11—C12—C13120.1 (4)
C4—C5—C6119.6 (4)C11—C12—H12120.0
C4—C5—H5120.2C13—C12—H12120.0
C6—C5—H5120.2
O1—C7—N1—C80.8 (5)C6—C1—C2—C30.3 (5)
C1—C7—N1—C8179.6 (3)C7—C1—C2—C3178.8 (3)
O1—C7—C1—C224.5 (5)C6—C5—C4—C30.7 (6)
N1—C7—C1—C2155.1 (3)C6—C5—C4—Br1178.2 (3)
O1—C7—C1—C6153.9 (3)C9—C8—C13—C120.3 (6)
N1—C7—C1—C626.5 (4)N1—C8—C13—C12178.8 (4)
C2—C1—C6—C50.3 (5)O2—C9—C10—C11178.0 (4)
C7—C1—C6—C5178.7 (3)C8—C9—C10—C111.3 (6)
O2—C9—C8—C13177.9 (3)C9—C10—C11—C120.1 (7)
C10—C9—C8—C131.4 (5)C5—C4—C3—C20.8 (6)
O2—C9—C8—N10.7 (4)Br1—C4—C3—C2178.1 (3)
C10—C9—C8—N1180.0 (3)C1—C2—C3—C40.6 (6)
C7—N1—C8—C9107.5 (4)C10—C11—C12—C131.1 (7)
C7—N1—C8—C1373.9 (5)C8—C13—C12—C111.0 (7)
C1—C6—C5—C40.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—HO2···O1i0.822.002.682 (3)141
N1—H1···O1ii0.862.022.824 (3)155
C6—H6···O2iii0.932.563.458 (5)164
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+3/2, z1/2; (iii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—HO2···O1i0.822.002.682 (3)141
N1—H1···O1ii0.862.022.824 (3)155
C6—H6···O2iii0.932.563.458 (5)164
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+3/2, z1/2; (iii) x, y+1, z.
 

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