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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-N′-(3-Bromo-5-chloro-2-hy­dr­oxy­benzyl­­idene)nicotinohydrazide

aShasun Pharmaceuticals Ltd, Chennai 600 048, India, bDepartment of Chemistry, Pondicherry University, Pondicherry 605014, India, cDepartment of Inorganic Chemistry, Madurai Kamaraj University, Madurai 625 021, India, dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and eDepartment of Chemistry, Government Arts College, Melur 625 106, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 15 September 2011; accepted 19 September 2011; online 30 September 2011)

There are two independent mol­ecules in the asymmetric unit of the title compound, C13H9BrClN3O2, in which the dihedral angles between the benzene and pyridine rings are 8.23 (9)° and 52.84 (12)°. Both the mol­ecules exist in an E configuration with respect to the C=N double bond. The two mol­ecules in the asymmetric unit are linked via weak C—H⋯O hydrogen bonds. In both the mol­ecules, an intra­molecular O—H⋯N hydrogen bond generate an S(6) graph-set motif. In the crystal, inter­molecular N—H⋯O and C—H⋯O hydrogen bonds generate bifurcated R12(7) ring motifs. The crystal packing is further stabilized by weak inter­molecular N—H⋯O, N—H⋯N, C—H⋯O and ππ [centroid–centroid distance 3.615 (2) Å] inter­actions.

Related literature

For related structures, see: Naveenkumar et al. (2010[Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o1235-o1236.]); Su et al. (2010[Su, Y.-Q., Li, C. & Wang, P. (2010). Acta Cryst. E66, o670.]); Tecer et al. (2010[Tecer, E., Dege, N., Zülfikaroğlu, A., Şenyüz, N. & Batı, H. (2010). Acta Cryst. E66, o3369-o3370.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9BrClN3O2

  • Mr = 354.59

  • Monoclinic, P 21 /c

  • a = 18.2217 (5) Å

  • b = 7.4666 (2) Å

  • c = 23.6916 (5) Å

  • β = 122.685 (1)°

  • V = 2712.93 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.23 mm−1

  • T = 295 K

  • 0.30 × 0.24 × 0.20 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.444, Tmax = 0.564

  • 34991 measured reflections

  • 8116 independent reflections

  • 4715 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.125

  • S = 1.02

  • 8116 reflections

  • 377 parameters

  • 4 restraints

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

  • Δρmax = 1.27 e Å−3

  • Δρmin = −0.84 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2B⋯N3 0.81 (1) 1.89 (3) 2.576 (3) 142 (4)
O4—H4A⋯N6 0.82 (1) 1.83 (2) 2.569 (3) 149 (4)
C15—H15⋯O2 0.93 2.55 3.286 (4) 137
C16—H16⋯O1 0.93 2.41 3.185 (4) 141
N2—H2A⋯O3i 0.85 (1) 2.06 (1) 2.906 (3) 171 (3)
C2—H2⋯O3i 0.93 2.52 3.380 (4) 153
N5—H5A⋯N1ii 0.86 (1) 2.16 (1) 3.009 (4) 170 (3)
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The geometric parameters of the title compound (I), agree well with the reported similar structures (Naveenkumar et al., 2010; Su et al., 2010; Tecer et al., 2010). The dihedral angles between the (C1/C2/N1/C3/C4/C5) and (C8-C13) is 8.23 (9)° and (C14/C15/C16/C17/N4/C18) and (C21-C26) is 52.84 (12)°. Both the molecules exist in an E configuration with respect to the C=N double bond. The two molecules in the asymmetric unit are linked via weak C15-H15···O2 and C16-H16···O1 hydrogen bonds. In both the molecules, the intramolecular O2-H2B···N3 and O4-H4A···N6 hydrogen bonds generate six-membered rings, each with graph-set motif S(6) (see, Fig. 1).

In the crystal structure (Fig. 2), the intermolecular N2-H2A···O3 and C2-H2···O3 hydrogen bonds generates a seven-membered ring, with bifurcated R1 2(7) ring motif. The crystal packing is further stabilized due to weak intermolecular N-H···N, N-H···O, C-H···O (Table 1 ) and π···π [Cg4···Cg4 (2-x,1-y,1-z) = 3.614 (2)Å; Cg4 is the centroid of the ring (C21-C26)] interactions.

Related literature top

For related structures, see: Naveenkumar et al. (2010); Su et al. (2010); Tecer et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Nicotinoylhydrazide (5 mmol) was dissolved in 20 mL of dry methanol with stirring and warming over a period of 10 min. To the warm hydrazide solution, 3- bromo-5-chloro salicylaldehyde (5 mmol) in 20 mL of dry methanol was added and the mixture was stirred and slowly refluxed for 2 h. The mixture was then cooled down to room temperature when pale yellow crystalline compound precipitated. The compound was collected by filtration, washed well with cold methanol and dried in vacuum. Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature. Melting Point: 503 K.

Refinement top

The amino and hydroxy H-atoms were located in a difference Fourier map, and were refined with N–H distance restraint of 0.86 (1) Å and O-H distance restraint of 0.82 (1) Å. All other H atoms were positioned geometrically with C-H = 0.93 Å, and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Structure description top

The geometric parameters of the title compound (I), agree well with the reported similar structures (Naveenkumar et al., 2010; Su et al., 2010; Tecer et al., 2010). The dihedral angles between the (C1/C2/N1/C3/C4/C5) and (C8-C13) is 8.23 (9)° and (C14/C15/C16/C17/N4/C18) and (C21-C26) is 52.84 (12)°. Both the molecules exist in an E configuration with respect to the C=N double bond. The two molecules in the asymmetric unit are linked via weak C15-H15···O2 and C16-H16···O1 hydrogen bonds. In both the molecules, the intramolecular O2-H2B···N3 and O4-H4A···N6 hydrogen bonds generate six-membered rings, each with graph-set motif S(6) (see, Fig. 1).

In the crystal structure (Fig. 2), the intermolecular N2-H2A···O3 and C2-H2···O3 hydrogen bonds generates a seven-membered ring, with bifurcated R1 2(7) ring motif. The crystal packing is further stabilized due to weak intermolecular N-H···N, N-H···O, C-H···O (Table 1 ) and π···π [Cg4···Cg4 (2-x,1-y,1-z) = 3.614 (2)Å; Cg4 is the centroid of the ring (C21-C26)] interactions.

For related structures, see: Naveenkumar et al. (2010); Su et al. (2010); Tecer et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
(E)-N'-(3-Bromo-5-chloro-2-hydroxybenzylidene)nicotinohydrazide top
Crystal data top
C13H9BrClN3O2F(000) = 1408
Mr = 354.59Dx = 1.736 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7402 reflections
a = 18.2217 (5) Åθ = 2.3–27.8°
b = 7.4666 (2) ŵ = 3.23 mm1
c = 23.6916 (5) ÅT = 295 K
β = 122.685 (1)°Block, pale yellow
V = 2712.93 (12) Å30.30 × 0.24 × 0.20 mm
Z = 8
Data collection top
Bruker APEXII
diffractometer
8116 independent reflections
Radiation source: fine-focus sealed tube4715 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω and φ scansθmax = 30.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2525
Tmin = 0.444, Tmax = 0.564k = 1010
34991 measured reflectionsl = 3133
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0543P)2 + 1.4342P]
where P = (Fo2 + 2Fc2)/3
8116 reflections(Δ/σ)max < 0.001
377 parametersΔρmax = 1.27 e Å3
4 restraintsΔρmin = 0.84 e Å3
Crystal data top
C13H9BrClN3O2V = 2712.93 (12) Å3
Mr = 354.59Z = 8
Monoclinic, P21/cMo Kα radiation
a = 18.2217 (5) ŵ = 3.23 mm1
b = 7.4666 (2) ÅT = 295 K
c = 23.6916 (5) Å0.30 × 0.24 × 0.20 mm
β = 122.685 (1)°
Data collection top
Bruker APEXII
diffractometer
8116 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4715 reflections with I > 2σ(I)
Tmin = 0.444, Tmax = 0.564Rint = 0.042
34991 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0474 restraints
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 1.27 e Å3
8116 reflectionsΔρmin = 0.84 e Å3
377 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.750800 (19)0.43505 (5)0.256817 (14)0.04545 (11)
Br20.92847 (3)0.37571 (8)0.62069 (2)0.08778 (19)
Cl10.97541 (6)0.57738 (16)0.17505 (5)0.0727 (3)
Cl21.13001 (5)0.78996 (14)0.56676 (6)0.0691 (3)
O10.41709 (16)0.7827 (4)0.01578 (11)0.0622 (7)
O20.62074 (13)0.5694 (3)0.11875 (10)0.0427 (5)
O30.56100 (13)0.6644 (3)0.35290 (10)0.0471 (6)
O40.78596 (14)0.5308 (4)0.49132 (11)0.0498 (6)
N10.31049 (16)1.0700 (4)0.22503 (12)0.0412 (6)
N20.50665 (16)0.7928 (4)0.05295 (12)0.0404 (6)
N30.57128 (15)0.7165 (4)0.00520 (11)0.0390 (6)
N40.34447 (16)0.7592 (5)0.16222 (15)0.0613 (9)
N50.65084 (14)0.7503 (4)0.31986 (11)0.0371 (6)
N60.72089 (14)0.7123 (4)0.38238 (11)0.0386 (6)
C10.36031 (18)0.9139 (4)0.12190 (14)0.0357 (6)
C20.37331 (18)0.9923 (4)0.16888 (14)0.0367 (6)
H20.42930.99040.16070.044*
C30.2310 (2)1.0706 (5)0.23508 (16)0.0463 (8)
H30.18571.12190.27440.056*
C40.2119 (2)1.0005 (5)0.19115 (17)0.0489 (8)
H40.15551.00620.20030.059*
C50.2773 (2)0.9218 (5)0.13355 (16)0.0454 (8)
H50.26610.87420.10260.054*
C60.42963 (19)0.8249 (4)0.05901 (14)0.0390 (7)
C70.64618 (19)0.6968 (5)0.01529 (14)0.0421 (7)
H70.65680.72850.01760.051*
C80.71621 (18)0.6234 (4)0.07931 (14)0.0384 (7)
C90.70035 (18)0.5672 (4)0.12829 (14)0.0348 (6)
C100.77050 (19)0.5086 (4)0.18998 (14)0.0367 (6)
C110.85431 (19)0.5085 (5)0.20395 (15)0.0430 (7)
H110.90050.46950.24540.052*
C120.86859 (19)0.5669 (5)0.15582 (17)0.0482 (8)
C130.8007 (2)0.6208 (5)0.09373 (17)0.0478 (8)
H130.81150.65570.06120.057*
C140.49790 (16)0.7151 (4)0.23663 (13)0.0323 (6)
C150.50623 (19)0.6727 (4)0.18378 (14)0.0389 (7)
H150.56030.64420.19090.047*
C160.4322 (2)0.6739 (5)0.12011 (15)0.0513 (9)
H160.43510.64560.08310.062*
C170.3545 (2)0.7173 (6)0.11241 (17)0.0604 (10)
H170.30500.71760.06910.073*
C180.41587 (18)0.7556 (5)0.22332 (16)0.0476 (8)
H180.41060.78170.25930.057*
C190.57123 (17)0.7085 (4)0.30792 (13)0.0340 (6)
C200.79620 (18)0.7645 (4)0.39838 (15)0.0393 (7)
H200.80300.83570.36930.047*
C210.87182 (18)0.7109 (4)0.46324 (15)0.0390 (7)
C220.86279 (18)0.5946 (4)0.50526 (15)0.0404 (7)
C230.9379 (2)0.5408 (5)0.56524 (15)0.0491 (8)
C241.0189 (2)0.6014 (5)0.58363 (16)0.0510 (9)
H241.06820.56440.62380.061*
C251.02624 (18)0.7172 (5)0.54212 (17)0.0473 (8)
C260.95434 (18)0.7721 (5)0.48211 (16)0.0455 (8)
H260.96080.84960.45430.055*
H2A0.517 (2)0.813 (5)0.0833 (13)0.054 (10)*
H5A0.655 (2)0.804 (4)0.2895 (12)0.041 (9)*
H2B0.5850 (19)0.618 (5)0.0836 (11)0.063 (12)*
H4A0.7488 (19)0.569 (5)0.4542 (10)0.068 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03930 (17)0.0614 (2)0.03022 (15)0.00234 (15)0.01524 (12)0.00653 (14)
Br20.0636 (3)0.1316 (5)0.0522 (2)0.0067 (3)0.0208 (2)0.0320 (3)
Cl10.0330 (4)0.1031 (8)0.0796 (7)0.0043 (5)0.0287 (4)0.0239 (6)
Cl20.0245 (4)0.0654 (6)0.0928 (7)0.0062 (4)0.0157 (4)0.0170 (5)
O10.0541 (14)0.102 (2)0.0400 (13)0.0159 (14)0.0314 (11)0.0236 (13)
O20.0291 (10)0.0656 (15)0.0317 (11)0.0023 (10)0.0152 (9)0.0069 (11)
O30.0347 (11)0.0793 (17)0.0298 (10)0.0008 (11)0.0190 (9)0.0019 (11)
O40.0314 (11)0.0760 (18)0.0374 (12)0.0003 (11)0.0155 (10)0.0022 (12)
N10.0359 (13)0.0505 (16)0.0348 (13)0.0051 (12)0.0176 (11)0.0087 (12)
N20.0339 (13)0.0601 (17)0.0249 (12)0.0015 (12)0.0143 (10)0.0063 (11)
N30.0341 (13)0.0509 (16)0.0251 (11)0.0002 (11)0.0115 (10)0.0051 (11)
N40.0264 (13)0.094 (3)0.0499 (17)0.0097 (15)0.0117 (12)0.0140 (17)
N50.0219 (11)0.0573 (17)0.0272 (12)0.0003 (11)0.0100 (9)0.0064 (11)
N60.0232 (11)0.0540 (16)0.0289 (12)0.0022 (11)0.0077 (9)0.0003 (11)
C10.0325 (14)0.0427 (18)0.0319 (14)0.0003 (13)0.0174 (12)0.0018 (12)
C20.0311 (14)0.0450 (17)0.0352 (15)0.0014 (13)0.0187 (12)0.0030 (13)
C30.0376 (16)0.055 (2)0.0391 (16)0.0046 (15)0.0160 (13)0.0046 (15)
C40.0322 (15)0.065 (2)0.0488 (18)0.0031 (15)0.0212 (14)0.0020 (17)
C50.0376 (16)0.059 (2)0.0467 (18)0.0010 (15)0.0272 (14)0.0026 (16)
C60.0361 (16)0.050 (2)0.0295 (14)0.0010 (13)0.0171 (12)0.0006 (13)
C70.0371 (16)0.058 (2)0.0272 (14)0.0037 (14)0.0148 (12)0.0067 (13)
C80.0325 (15)0.0487 (19)0.0306 (14)0.0015 (13)0.0149 (12)0.0043 (13)
C90.0294 (13)0.0389 (16)0.0317 (13)0.0021 (12)0.0135 (11)0.0004 (12)
C100.0351 (15)0.0404 (17)0.0312 (14)0.0037 (13)0.0156 (12)0.0011 (12)
C110.0305 (15)0.0516 (19)0.0368 (16)0.0020 (14)0.0117 (13)0.0049 (14)
C120.0285 (14)0.062 (2)0.0513 (19)0.0014 (15)0.0196 (14)0.0073 (17)
C130.0375 (16)0.065 (2)0.0461 (18)0.0016 (15)0.0260 (15)0.0093 (16)
C140.0234 (12)0.0395 (17)0.0308 (14)0.0019 (12)0.0125 (11)0.0050 (12)
C150.0308 (14)0.054 (2)0.0307 (14)0.0013 (13)0.0161 (12)0.0047 (13)
C160.0460 (19)0.070 (2)0.0288 (15)0.0042 (17)0.0143 (14)0.0041 (15)
C170.0329 (17)0.087 (3)0.0378 (18)0.0017 (18)0.0037 (14)0.0145 (18)
C180.0293 (15)0.067 (2)0.0448 (18)0.0084 (15)0.0190 (14)0.0077 (16)
C190.0279 (13)0.0443 (17)0.0304 (14)0.0024 (12)0.0162 (11)0.0003 (12)
C200.0288 (14)0.0459 (19)0.0368 (15)0.0010 (13)0.0135 (12)0.0013 (13)
C210.0248 (13)0.0464 (18)0.0373 (15)0.0014 (13)0.0112 (12)0.0089 (13)
C220.0283 (14)0.054 (2)0.0342 (15)0.0028 (13)0.0137 (12)0.0076 (13)
C230.0391 (17)0.065 (2)0.0342 (15)0.0096 (16)0.0142 (13)0.0013 (15)
C240.0306 (15)0.065 (2)0.0368 (16)0.0095 (15)0.0047 (13)0.0106 (16)
C250.0209 (13)0.051 (2)0.0547 (19)0.0005 (13)0.0102 (13)0.0177 (17)
C260.0285 (14)0.048 (2)0.0509 (19)0.0029 (14)0.0152 (14)0.0088 (15)
Geometric parameters (Å, º) top
Br1—C101.885 (3)C5—H50.9300
Br2—C231.876 (4)C7—C81.462 (4)
Cl1—C121.745 (3)C7—H70.9300
Cl2—C251.738 (3)C8—C131.384 (4)
O1—C61.205 (4)C8—C91.403 (4)
O2—C91.342 (3)C9—C101.394 (4)
O2—H2B0.814 (10)C10—C111.377 (4)
O3—C191.222 (3)C11—C121.370 (5)
O4—C221.341 (4)C11—H110.9300
O4—H4A0.818 (10)C12—C131.375 (4)
N1—C21.331 (4)C13—H130.9300
N1—C31.336 (4)C14—C151.377 (4)
N2—C61.353 (4)C14—C181.384 (4)
N2—N31.363 (3)C14—C191.484 (4)
N2—H2A0.853 (10)C15—C161.378 (4)
N3—C71.261 (4)C15—H150.9300
N4—C181.325 (4)C16—C171.366 (5)
N4—C171.325 (5)C16—H160.9300
N5—C191.356 (4)C17—H170.9300
N5—N61.364 (3)C18—H180.9300
N5—H5A0.860 (10)C20—C211.461 (4)
N6—C201.272 (4)C20—H200.9300
C1—C51.385 (4)C21—C261.394 (4)
C1—C21.386 (4)C21—C221.396 (5)
C1—C61.492 (4)C22—C231.398 (4)
C2—H20.9300C23—C241.371 (5)
C3—C41.367 (5)C24—C251.369 (5)
C3—H30.9300C24—H240.9300
C4—C51.368 (5)C25—C261.376 (4)
C4—H40.9300C26—H260.9300
C9—O2—H2B112 (3)C11—C12—C13121.2 (3)
C22—O4—H4A107 (3)C11—C12—Cl1118.9 (2)
C2—N1—C3116.4 (3)C13—C12—Cl1119.9 (3)
C6—N2—N3117.5 (2)C12—C13—C8120.4 (3)
C6—N2—H2A125 (2)C12—C13—H13119.8
N3—N2—H2A117 (2)C8—C13—H13119.8
C7—N3—N2119.8 (2)C15—C14—C18118.6 (3)
C18—N4—C17116.2 (3)C15—C14—C19123.6 (2)
C19—N5—N6116.5 (2)C18—C14—C19117.7 (3)
C19—N5—H5A120 (2)C14—C15—C16118.1 (3)
N6—N5—H5A124 (2)C14—C15—H15121.0
C20—N6—N5119.1 (3)C16—C15—H15121.0
C5—C1—C2117.7 (3)C17—C16—C15118.6 (3)
C5—C1—C6117.6 (3)C17—C16—H16120.7
C2—C1—C6124.8 (3)C15—C16—H16120.7
N1—C2—C1124.0 (3)N4—C17—C16124.6 (3)
N1—C2—H2118.0N4—C17—H17117.7
C1—C2—H2118.0C16—C17—H17117.7
N1—C3—C4124.1 (3)N4—C18—C14123.8 (3)
N1—C3—H3118.0N4—C18—H18118.1
C4—C3—H3118.0C14—C18—H18118.1
C3—C4—C5118.7 (3)O3—C19—N5122.0 (3)
C3—C4—H4120.6O3—C19—C14122.3 (3)
C5—C4—H4120.6N5—C19—C14115.7 (2)
C4—C5—C1119.1 (3)N6—C20—C21118.8 (3)
C4—C5—H5120.4N6—C20—H20120.6
C1—C5—H5120.4C21—C20—H20120.6
O1—C6—N2121.7 (3)C26—C21—C22119.8 (3)
O1—C6—C1121.2 (3)C26—C21—C20119.3 (3)
N2—C6—C1117.1 (2)C22—C21—C20120.9 (3)
N3—C7—C8119.3 (3)O4—C22—C21123.7 (3)
N3—C7—H7120.3O4—C22—C23117.8 (3)
C8—C7—H7120.3C21—C22—C23118.4 (3)
C13—C8—C9119.3 (3)C24—C23—C22121.6 (3)
C13—C8—C7119.5 (3)C24—C23—Br2119.0 (2)
C9—C8—C7121.0 (3)C22—C23—Br2119.4 (3)
O2—C9—C10118.4 (3)C25—C24—C23119.1 (3)
O2—C9—C8122.9 (2)C25—C24—H24120.5
C10—C9—C8118.6 (3)C23—C24—H24120.5
C11—C10—C9121.5 (3)C24—C25—C26121.5 (3)
C11—C10—Br1119.2 (2)C24—C25—Cl2117.8 (2)
C9—C10—Br1119.3 (2)C26—C25—Cl2120.7 (3)
C12—C11—C10119.0 (3)C25—C26—C21119.6 (3)
C12—C11—H11120.5C25—C26—H26120.2
C10—C11—H11120.5C21—C26—H26120.2
C6—N2—N3—C7174.5 (3)C7—C8—C13—C12174.4 (3)
C19—N5—N6—C20173.2 (3)C18—C14—C15—C160.4 (5)
C3—N1—C2—C10.2 (5)C19—C14—C15—C16176.2 (3)
C5—C1—C2—N11.8 (5)C14—C15—C16—C170.2 (5)
C6—C1—C2—N1179.5 (3)C18—N4—C17—C160.8 (6)
C2—N1—C3—C41.3 (5)C15—C16—C17—N40.0 (6)
N1—C3—C4—C51.1 (6)C17—N4—C18—C141.4 (6)
C3—C4—C5—C10.6 (5)C15—C14—C18—N41.3 (5)
C2—C1—C5—C42.0 (5)C19—C14—C18—N4177.4 (3)
C6—C1—C5—C4179.2 (3)N6—N5—C19—O310.6 (4)
N3—N2—C6—O12.4 (5)N6—N5—C19—C14167.8 (3)
N3—N2—C6—C1178.0 (3)C15—C14—C19—O3145.3 (3)
C5—C1—C6—O19.7 (5)C18—C14—C19—O330.6 (5)
C2—C1—C6—O1169.1 (3)C15—C14—C19—N533.1 (4)
C5—C1—C6—N2169.9 (3)C18—C14—C19—N5151.0 (3)
C2—C1—C6—N211.3 (5)N5—N6—C20—C21175.0 (3)
N2—N3—C7—C8176.8 (3)N6—C20—C21—C26178.0 (3)
N3—C7—C8—C13172.5 (3)N6—C20—C21—C224.2 (5)
N3—C7—C8—C93.0 (5)C26—C21—C22—O4179.3 (3)
C13—C8—C9—O2178.5 (3)C20—C21—C22—O42.9 (5)
C7—C8—C9—O23.0 (5)C26—C21—C22—C230.9 (5)
C13—C8—C9—C100.6 (5)C20—C21—C22—C23176.9 (3)
C7—C8—C9—C10176.1 (3)O4—C22—C23—C24179.3 (3)
O2—C9—C10—C11177.8 (3)C21—C22—C23—C240.9 (5)
C8—C9—C10—C111.3 (5)O4—C22—C23—Br22.9 (4)
O2—C9—C10—Br10.1 (4)C21—C22—C23—Br2176.9 (2)
C8—C9—C10—Br1179.3 (2)C22—C23—C24—C250.1 (5)
C9—C10—C11—C120.2 (5)Br2—C23—C24—C25177.8 (3)
Br1—C10—C11—C12178.2 (3)C23—C24—C25—C260.8 (5)
C10—C11—C12—C131.6 (5)C23—C24—C25—Cl2179.6 (3)
C10—C11—C12—Cl1176.8 (3)C24—C25—C26—C210.9 (5)
C11—C12—C13—C82.4 (6)Cl2—C25—C26—C21179.6 (2)
Cl1—C12—C13—C8176.0 (3)C22—C21—C26—C250.0 (5)
C9—C8—C13—C121.2 (5)C20—C21—C26—C25177.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···N30.81 (1)1.89 (3)2.576 (3)142 (4)
O4—H4A···N60.82 (1)1.83 (2)2.569 (3)149 (4)
C15—H15···O20.932.553.286 (4)137
C16—H16···O10.932.413.185 (4)141
N2—H2A···O3i0.85 (1)2.06 (1)2.906 (3)171 (3)
C2—H2···O3i0.932.523.380 (4)153
N5—H5A···N1ii0.86 (1)2.16 (1)3.009 (4)170 (3)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC13H9BrClN3O2
Mr354.59
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)18.2217 (5), 7.4666 (2), 23.6916 (5)
β (°) 122.685 (1)
V3)2712.93 (12)
Z8
Radiation typeMo Kα
µ (mm1)3.23
Crystal size (mm)0.30 × 0.24 × 0.20
Data collection
DiffractometerBruker APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.444, 0.564
No. of measured, independent and
observed [I > 2σ(I)] reflections
34991, 8116, 4715
Rint0.042
(sin θ/λ)max1)0.711
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.125, 1.02
No. of reflections8116
No. of parameters377
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.27, 0.84

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···N30.81 (1)1.89 (3)2.576 (3)142 (4)
O4—H4A···N60.82 (1)1.83 (2)2.569 (3)149 (4)
C15—H15···O20.932.553.286 (4)137
C16—H16···O10.932.413.185 (4)141
N2—H2A···O3i0.85 (1)2.06 (1)2.906 (3)171 (3)
C2—H2···O3i0.932.523.380 (4)153
N5—H5A···N1ii0.86 (1)2.16 (1)3.009 (4)170 (3)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+2, z.
 

Acknowledgements

The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.

References

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