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COMMUNICATIONS
ISSN: 2056-9890

N′-(5-Bromo-2-hy­droxy­benzyl­­idene)-3-hy­droxy­benzohydrazide

aDepartment of Chemistry, Qufu Normal University, Qufu 273165, People's Republic of China
*Correspondence e-mail: nieyi68@126.com

(Received 4 January 2008; accepted 22 January 2008; online 25 January 2008)

The asymmetric unit of the title compound, C14H11BrN2O3, contains two crystallographically independent mol­ecules with slightly different conformations with respect to the aromatic rings; the dihedral angles between the two benzene rings in the two mol­ecules are 55.0 (7) and 16.3 (7)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, forming chains running along the a axis.

Related literature

For related literature, see: Akitsu & Einaga (2006[Akitsu, T. & Einaga, Y. (2006). Acta Cryst. E62, o4315-o4317.]); Bahner et al. (1968[Bahner, C. T., Brotherton, D. & Brotherton, M. K. (1968). J. Med. Chem. 11, 405-406.]); Butcher et al. (2005[Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007-o1009.]); Hodnett & Mooney (1970[Hodnett, E. M. & Mooney, P. D. (1970). J. Med. Chem. 13, 786-786.]); Merchant & Chothia (1970[Merchant, J. R. & Chothia, D. S. (1970). J. Med. Chem. 13, 335-336.]); Pradeep (2005[Pradeep, C. P. (2005). Acta Cryst. E61, o3825-o3827.]); Sigman & Jacobsen (1998[Sigman, M. S. & Jacobsen, E. N. (1998). J. Am. Chem. Soc. 120, 4901-4902.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11BrN2O3

  • Mr = 335.16

  • Triclinic, [P \overline 1]

  • a = 6.295 (3) Å

  • b = 14.988 (4) Å

  • c = 15.423 (3) Å

  • α = 70.97 (2)°

  • β = 80.64 (2)°

  • γ = 78.02 (2)°

  • V = 1338.6 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.08 mm−1

  • T = 298 (2) K

  • 0.20 × 0.18 × 0.18 mm

Data collection
  • Bruker SMART APEX area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.549, Tmax = 0.577

  • 11037 measured reflections

  • 5652 independent reflections

  • 2286 reflections with I > 2σ(I)

  • Rint = 0.078

Refinement
  • R[F2 > 2σ(F2)] = 0.072

  • wR(F2) = 0.193

  • S = 0.93

  • 5652 reflections

  • 371 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.70 e Å−3

  • Δρmin = −0.50 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4—H4B⋯O6i 0.90 (5) 2.60 (8) 3.045 (9) 111 (6)
N2—H2⋯O3ii 0.90 (6) 2.39 (7) 3.021 (9) 127 (7)
O6—H6⋯O5iii 0.82 2.14 2.760 (8) 132
O4—H4⋯N3 0.82 1.95 2.665 (8) 145
O3—H3⋯O2iv 0.82 1.93 2.737 (8) 167
O1—H1⋯N1 0.82 1.94 2.654 (8) 145
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x+1, -y+1, -z+2; (iv) -x, -y+2, -z+2.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL97.

Supporting information


Comment top

Schiff base compounds have been widely investigated due to their easy synthesis, versatile structures and widely applications (Sigman & Jacobsen, 1998; Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005). The excellent antibacterial and antitumor properties of such compounds have attracted much interest in recent years (Hodnett & Mooney, 1970; Bahner et al., 1968; Merchant & Chothia, 1970). In order to further investigate the structures of such compounds, a new Schiff base compound is reported in this paper.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1) with slightly different conformation with respect to the aromatic ring planes. The dihedral angles between the two benzene rings in the molecules are 55.0 (7) and 16.3 (7)°, respectively. The molecular conformation is stabilized by intramolecular N—H···O hydrogen bonding interactions (Table 1). In the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), forming chains running along the a axis (Fig. 2).

Related literature top

For related literature, see: Akitsu & Einaga (2006); Bahner et al. (1968); Butcher et al. (2005); Hodnett & Mooney (1970); Merchant & Chothia (1970); Pradeep (2005); Sigman & Jacobsen (1998).

Experimental top

The title compound was obtained by stirring of 5-bromosalicylaldehyde (0.1 mmol, 20.1 mg) and 3-hydroxybenzoic acid hydrazide (0.1 mmol, 15.2 mg) in a methanol solution (10 ml) at room temperature. Yellow block-shaped single crystals suitable for X-ray diffraction were formed from the solution after three days.

Refinement top

H2 and H4B were located from a difference Fourier map and refined isotropically, with N–H distances restrained to 0.90 (1) Å, and with Uiso(H) set to 0.08 Å2. Other H atoms were positioned geometrically (C–H = 0.93Å and O–H = 0.82 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids.
[Figure 2] Fig. 2. Molecular packing of the title compound. Hydrogen atoms not involved in intermolecular hydrogen bonds (dashed lines) are omitted for clarity.
N'-(5-Bromo-2-hydroxybenzylidene)-3-hydroxybenzohydrazide top
Crystal data top
C14H11BrN2O3Z = 4
Mr = 335.16F(000) = 672
Triclinic, P1Dx = 1.663 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.295 (3) ÅCell parameters from 819 reflections
b = 14.988 (4) Åθ = 2.3–24.3°
c = 15.423 (3) ŵ = 3.08 mm1
α = 70.97 (2)°T = 298 K
β = 80.64 (2)°Block, yellow
γ = 78.02 (2)°0.20 × 0.18 × 0.18 mm
V = 1338.6 (8) Å3
Data collection top
Bruker SMART APEX area-detector
diffractometer
5652 independent reflections
Radiation source: fine-focus sealed tube2286 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
ω scansθmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.549, Tmax = 0.577k = 1919
11037 measured reflectionsl = 1919
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)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H atoms treated by a mixture of independent and constrained refinement
S = 0.93 w = 1/[σ2(Fo2) + (0.0728P)2]
where P = (Fo2 + 2Fc2)/3
5652 reflections(Δ/σ)max < 0.001
371 parametersΔρmax = 0.70 e Å3
2 restraintsΔρmin = 0.50 e Å3
Crystal data top
C14H11BrN2O3γ = 78.02 (2)°
Mr = 335.16V = 1338.6 (8) Å3
Triclinic, P1Z = 4
a = 6.295 (3) ÅMo Kα radiation
b = 14.988 (4) ŵ = 3.08 mm1
c = 15.423 (3) ÅT = 298 K
α = 70.97 (2)°0.20 × 0.18 × 0.18 mm
β = 80.64 (2)°
Data collection top
Bruker SMART APEX area-detector
diffractometer
5652 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2286 reflections with I > 2σ(I)
Tmin = 0.549, Tmax = 0.577Rint = 0.078
11037 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0722 restraints
wR(F2) = 0.193H atoms treated by a mixture of independent and constrained refinement
S = 0.93Δρmax = 0.70 e Å3
5652 reflectionsΔρmin = 0.50 e Å3
371 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
Br10.88585 (14)0.92277 (7)0.36574 (6)0.0631 (3)
Br21.22791 (15)0.68828 (8)0.26774 (6)0.0759 (4)
O10.1995 (9)0.8047 (5)0.6860 (4)0.0657 (17)
H10.22240.81730.73120.099*
O20.1318 (8)0.8815 (4)0.9236 (4)0.0558 (15)
O30.1855 (9)1.0107 (5)1.1872 (4)0.0620 (16)
H30.07781.03651.15930.093*
O40.5513 (9)0.5809 (5)0.5941 (4)0.0649 (17)
H40.58710.58660.64060.097*
O50.5448 (9)0.6020 (4)0.8512 (3)0.0600 (16)
O60.7038 (9)0.5109 (5)1.1850 (3)0.0656 (17)
H60.57970.50501.18050.098*
N10.4379 (10)0.8497 (4)0.7878 (4)0.0450 (16)
N20.4909 (11)0.8521 (5)0.8700 (4)0.0530 (18)
N30.8090 (10)0.6223 (5)0.6916 (4)0.0504 (18)
N40.8723 (10)0.6282 (5)0.7716 (4)0.0491 (17)
C10.5485 (13)0.8594 (5)0.6307 (5)0.047 (2)
C20.3583 (13)0.8316 (6)0.6156 (6)0.050 (2)
C30.3325 (14)0.8293 (6)0.5294 (6)0.058 (2)
H3A0.20830.81020.52070.069*
C40.4872 (14)0.8549 (6)0.4561 (6)0.059 (2)
H4A0.46820.85300.39820.070*
C50.6726 (13)0.8837 (5)0.4693 (5)0.049 (2)
C60.7046 (12)0.8877 (5)0.5549 (5)0.049 (2)
H6A0.82760.90880.56210.059*
C70.5847 (14)0.8639 (5)0.7195 (5)0.051 (2)
H70.71720.87740.72690.061*
C80.3276 (13)0.8706 (5)0.9354 (5)0.044 (2)
C90.3987 (13)0.8760 (5)1.0207 (5)0.044 (2)
C100.2543 (12)0.9334 (5)1.0679 (5)0.045 (2)
H100.11600.96071.04930.054*
C110.3203 (13)0.9490 (6)1.1430 (5)0.052 (2)
C120.5208 (13)0.9068 (6)1.1729 (5)0.053 (2)
H120.56490.91821.22250.064*
C130.6573 (14)0.8467 (6)1.1277 (6)0.061 (2)
H130.78980.81491.15030.073*
C140.6038 (13)0.8326 (6)1.0512 (6)0.056 (2)
H140.70170.79501.02010.067*
C150.9095 (12)0.6284 (5)0.5347 (5)0.044 (2)
C160.7120 (13)0.6035 (5)0.5224 (5)0.046 (2)
C170.6807 (13)0.5990 (6)0.4375 (6)0.057 (2)
H170.55590.57840.43140.069*
C180.8289 (13)0.6240 (6)0.3624 (6)0.056 (2)
H180.80240.62290.30510.067*
C191.0199 (13)0.6510 (6)0.3722 (5)0.052 (2)
C201.0584 (12)0.6519 (6)0.4565 (5)0.049 (2)
H201.18850.66870.46210.059*
C210.9532 (13)0.6323 (5)0.6225 (5)0.048 (2)
H211.09010.64250.62860.058*
C220.7317 (13)0.6159 (5)0.8508 (5)0.046 (2)
C230.8148 (11)0.6196 (5)0.9341 (5)0.0408 (19)
C240.7138 (12)0.5723 (5)1.0196 (5)0.048 (2)
H240.59210.54511.02200.057*
C250.7917 (13)0.5653 (6)1.1006 (5)0.047 (2)
C260.9760 (13)0.6038 (6)1.0988 (6)0.052 (2)
H261.03200.59641.15340.063*
C271.0751 (12)0.6534 (5)1.0148 (5)0.047 (2)
H271.19330.68241.01330.056*
C280.9992 (12)0.6601 (5)0.9322 (6)0.050 (2)
H281.07030.69120.87610.060*
H20.615 (7)0.860 (6)0.886 (5)0.080*
H4B1.004 (6)0.643 (6)0.771 (5)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0515 (6)0.0820 (7)0.0483 (6)0.0067 (5)0.0040 (4)0.0167 (5)
Br20.0608 (6)0.1244 (10)0.0477 (6)0.0376 (6)0.0053 (5)0.0243 (6)
O10.055 (4)0.095 (5)0.056 (4)0.035 (3)0.002 (3)0.025 (4)
O20.038 (3)0.077 (4)0.058 (4)0.011 (3)0.001 (3)0.029 (3)
O30.043 (3)0.100 (5)0.056 (4)0.015 (3)0.002 (3)0.042 (4)
O40.054 (4)0.095 (5)0.051 (4)0.033 (3)0.002 (3)0.017 (4)
O50.045 (4)0.090 (5)0.048 (3)0.031 (3)0.005 (3)0.013 (3)
O60.045 (4)0.112 (5)0.042 (3)0.028 (4)0.001 (3)0.019 (3)
N10.046 (4)0.049 (4)0.042 (4)0.005 (3)0.000 (3)0.019 (3)
N20.043 (4)0.076 (5)0.041 (4)0.007 (4)0.001 (3)0.023 (4)
N30.039 (4)0.067 (5)0.040 (4)0.005 (3)0.003 (3)0.013 (4)
N40.035 (4)0.071 (5)0.045 (4)0.018 (4)0.002 (3)0.017 (4)
C10.053 (5)0.034 (5)0.048 (5)0.004 (4)0.003 (4)0.011 (4)
C20.041 (5)0.057 (6)0.055 (6)0.011 (4)0.008 (4)0.016 (4)
C30.052 (6)0.068 (6)0.057 (6)0.017 (5)0.009 (5)0.019 (5)
C40.061 (6)0.075 (7)0.049 (5)0.020 (5)0.001 (5)0.028 (5)
C50.051 (5)0.044 (5)0.039 (5)0.008 (4)0.000 (4)0.006 (4)
C60.042 (5)0.052 (6)0.055 (5)0.011 (4)0.010 (4)0.013 (4)
C70.054 (5)0.058 (6)0.043 (5)0.014 (4)0.001 (4)0.017 (4)
C80.048 (5)0.040 (5)0.046 (5)0.011 (4)0.005 (4)0.013 (4)
C90.049 (5)0.041 (5)0.039 (5)0.007 (4)0.002 (4)0.012 (4)
C100.038 (5)0.053 (5)0.039 (5)0.009 (4)0.003 (4)0.010 (4)
C110.046 (5)0.066 (6)0.043 (5)0.018 (5)0.001 (4)0.013 (4)
C120.052 (6)0.069 (6)0.040 (5)0.010 (5)0.009 (4)0.016 (4)
C130.057 (6)0.054 (6)0.058 (6)0.002 (5)0.015 (5)0.001 (5)
C140.049 (5)0.062 (6)0.057 (6)0.007 (5)0.007 (4)0.019 (5)
C150.039 (5)0.057 (6)0.040 (5)0.012 (4)0.006 (4)0.015 (4)
C160.049 (5)0.050 (5)0.041 (5)0.014 (4)0.008 (4)0.011 (4)
C170.046 (5)0.076 (7)0.057 (6)0.020 (5)0.008 (5)0.021 (5)
C180.049 (5)0.065 (6)0.059 (6)0.008 (5)0.016 (5)0.023 (5)
C190.047 (5)0.067 (6)0.041 (5)0.010 (4)0.005 (4)0.017 (4)
C200.037 (5)0.064 (6)0.052 (5)0.022 (4)0.001 (4)0.018 (4)
C210.041 (5)0.053 (6)0.047 (5)0.009 (4)0.007 (4)0.009 (4)
C220.036 (5)0.041 (5)0.056 (5)0.012 (4)0.000 (4)0.009 (4)
C230.031 (4)0.041 (5)0.056 (5)0.005 (4)0.012 (4)0.019 (4)
C240.033 (4)0.057 (6)0.059 (5)0.023 (4)0.011 (4)0.024 (4)
C250.040 (5)0.058 (6)0.049 (5)0.002 (4)0.005 (4)0.025 (4)
C260.045 (5)0.061 (6)0.056 (5)0.007 (4)0.006 (4)0.027 (5)
C270.042 (5)0.040 (5)0.061 (5)0.013 (4)0.012 (4)0.012 (4)
C280.044 (5)0.049 (5)0.059 (5)0.015 (4)0.001 (4)0.015 (4)
Geometric parameters (Å, º) top
Br1—C51.928 (7)C9—C141.400 (10)
Br2—C191.912 (8)C9—C101.401 (9)
O1—C21.368 (9)C10—C111.395 (10)
O1—H10.8200C10—H100.9300
O2—C81.245 (9)C11—C121.369 (11)
O3—C111.392 (9)C12—C131.388 (10)
O3—H30.8200C12—H120.9300
O4—C161.377 (8)C13—C141.369 (11)
O4—H40.8200C13—H130.9300
O5—C221.235 (8)C14—H140.9300
O6—C251.388 (9)C15—C201.396 (9)
O6—H60.8200C15—C161.427 (10)
N1—C71.276 (8)C15—C211.447 (10)
N1—N21.375 (8)C16—C171.380 (10)
N2—C81.371 (9)C17—C181.365 (10)
N2—H20.90 (6)C17—H170.9300
N3—C211.273 (8)C18—C191.391 (11)
N3—N41.390 (8)C18—H180.9300
N4—C221.371 (9)C19—C201.365 (10)
N4—H4B0.90 (5)C20—H200.9300
C1—C61.410 (10)C21—H210.9300
C1—C21.422 (10)C22—C231.485 (10)
C1—C71.450 (10)C23—C241.397 (10)
C2—C31.377 (10)C23—C281.410 (10)
C3—C41.374 (10)C24—C251.380 (10)
C3—H3A0.9300C24—H240.9300
C4—C51.391 (11)C25—C261.392 (10)
C4—H4A0.9300C26—C271.386 (10)
C5—C61.388 (10)C26—H260.9300
C6—H6A0.9300C27—C281.398 (10)
C7—H70.9300C27—H270.9300
C8—C91.488 (10)C28—H280.9300
C2—O1—H1109.5C14—C13—C12122.3 (8)
C11—O3—H3109.5C14—C13—H13118.8
C16—O4—H4109.5C12—C13—H13118.8
C25—O6—H6109.5C13—C14—C9118.7 (8)
C7—N1—N2116.6 (7)C13—C14—H14120.7
C8—N2—N1119.5 (6)C9—C14—H14120.7
C8—N2—H2107 (5)C20—C15—C16116.6 (7)
N1—N2—H2132 (5)C20—C15—C21120.9 (7)
C21—N3—N4115.7 (7)C16—C15—C21122.5 (7)
C22—N4—N3120.6 (6)O4—C16—C17118.2 (7)
C22—N4—H4B119 (5)O4—C16—C15121.7 (7)
N3—N4—H4B120 (5)C17—C16—C15120.1 (7)
C6—C1—C2118.4 (7)C18—C17—C16121.5 (8)
C6—C1—C7118.5 (8)C18—C17—H17119.3
C2—C1—C7123.1 (7)C16—C17—H17119.3
O1—C2—C3118.5 (7)C17—C18—C19119.3 (8)
O1—C2—C1121.2 (7)C17—C18—H18120.3
C3—C2—C1120.4 (8)C19—C18—H18120.3
C4—C3—C2121.1 (8)C20—C19—C18120.0 (7)
C4—C3—H3A119.4C20—C19—Br2119.8 (6)
C2—C3—H3A119.4C18—C19—Br2120.2 (6)
C3—C4—C5119.3 (8)C19—C20—C15122.4 (7)
C3—C4—H4A120.4C19—C20—H20118.8
C5—C4—H4A120.4C15—C20—H20118.8
C6—C5—C4121.6 (7)N3—C21—C15121.7 (7)
C6—C5—Br1119.2 (7)N3—C21—H21119.2
C4—C5—Br1119.2 (6)C15—C21—H21119.2
C5—C6—C1119.3 (8)O5—C22—N4120.2 (7)
C5—C6—H6A120.4O5—C22—C23122.6 (7)
C1—C6—H6A120.4N4—C22—C23117.2 (7)
N1—C7—C1121.1 (8)C24—C23—C28118.4 (7)
N1—C7—H7119.5C24—C23—C22117.1 (7)
C1—C7—H7119.5C28—C23—C22124.2 (7)
O2—C8—N2121.4 (7)C25—C24—C23121.1 (7)
O2—C8—C9122.5 (7)C25—C24—H24119.5
N2—C8—C9116.1 (7)C23—C24—H24119.5
C14—C9—C10119.9 (7)C24—C25—O6120.9 (7)
C14—C9—C8123.5 (7)C24—C25—C26120.6 (8)
C10—C9—C8116.5 (7)O6—C25—C26118.2 (7)
C11—C10—C9119.3 (7)C27—C26—C25119.3 (8)
C11—C10—H10120.4C27—C26—H26120.4
C9—C10—H10120.4C25—C26—H26120.4
C12—C11—O3118.7 (7)C26—C27—C28120.6 (7)
C12—C11—C10120.9 (8)C26—C27—H27119.7
O3—C11—C10120.3 (7)C28—C27—H27119.7
C11—C12—C13118.8 (8)C27—C28—C23119.9 (7)
C11—C12—H12120.6C27—C28—H28120.0
C13—C12—H12120.6C23—C28—H28120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4B···O6i0.90 (5)2.60 (8)3.045 (9)111 (6)
N2—H2···O3ii0.90 (6)2.39 (7)3.021 (9)127 (7)
O6—H6···O5iii0.822.142.760 (8)132
O4—H4···N30.821.952.665 (8)145
O3—H3···O2iv0.821.932.737 (8)167
O1—H1···N10.821.942.654 (8)145
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+2, z+2; (iii) x+1, y+1, z+2; (iv) x, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC14H11BrN2O3
Mr335.16
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)6.295 (3), 14.988 (4), 15.423 (3)
α, β, γ (°)70.97 (2), 80.64 (2), 78.02 (2)
V3)1338.6 (8)
Z4
Radiation typeMo Kα
µ (mm1)3.08
Crystal size (mm)0.20 × 0.18 × 0.18
Data collection
DiffractometerBruker SMART APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.549, 0.577
No. of measured, independent and
observed [I > 2σ(I)] reflections
11037, 5652, 2286
Rint0.078
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.193, 0.93
No. of reflections5652
No. of parameters371
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.70, 0.50

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4B···O6i0.90 (5)2.60 (8)3.045 (9)111 (6)
N2—H2···O3ii0.90 (6)2.39 (7)3.021 (9)127 (7)
O6—H6···O5iii0.822.142.760 (8)132.3
O4—H4···N30.821.952.665 (8)145.3
O3—H3···O2iv0.821.932.737 (8)166.5
O1—H1···N10.821.942.654 (8)144.8
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+2, z+2; (iii) x+1, y+1, z+2; (iv) x, y+2, z+2.
 

References

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First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSigman, M. S. & Jacobsen, E. N. (1998). J. Am. Chem. Soc. 120, 4901–4902.  Web of Science CrossRef CAS Google Scholar

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