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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-(4-Bromo­phen­yl)-6-(4-chloro­phen­yl)­pyrimidin-2-ylamine

aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, bDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
*Correspondence e-mail: drhamidlatif@yahoo.com

(Received 1 December 2008; accepted 22 January 2009; online 28 January 2009)

The title compound, C16H11BrClN3, contains pairs of mol­ecules lying about inversion centers linked by amino–pyrimidine N—H⋯N hydrogen bonds. The eight-membered rings thus formed are represented by the R22(8) motif in graph-set notation. The second H atom of the amine group shows a rather weak inter­action with two Br atoms, resulting in bifurcated N—H⋯(Br,Br) hydrogen bonds. The dihedral angles between the mean planes of the benzene rings and the mean plane of the heterocyclic ring are 8.98 (15) and 35.58 (10)°. The Br and Cl atoms show substitutional disorder, with site-occupancy factors of 0.599 (2) and 0.401 (2), respectively.

Related literature

For related structures, see: Bukhari et al. (2008[Bukhari, M. H., Siddiqui, H. L., Chaudhary, M. A., Hussain, T. & Parvez, M. (2008). Acta Cryst. E64, o963.]); Fun et al. (2006[Fun, H.-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006). Acta Cryst. E62, o5332-o5334.]); Gallagher et al. (2004[Gallagher, J. F., Goswami, S., Chatterjee, B., Jana, S. & Dutta, K. (2004). Acta Cryst. C60, o229-o231.]). For pharmacological activities of pyrimidines, see: Gangjee et al. (1999[Gangjee, A., Aldair, O. & Queener, S. F. (1999). J. Med. Chem. 42, 2447-2455.]); Grivsky et al. (1980[Grivsky, E. D., Lee, S., Sigel, C. W., Duch, D. S. & Nichol, C. A. (1980). J. Med. Chem. 23, 227-229.]); Malik et al. (2006[Malik, V., Singh, P. & Kumar, S. (2006). Tetrahedron, 62, 5944-5951.]); Rao et al. (2003[Rao, M. S., Ehso, N., Sergeant, C. & Dembinski, R. (2003). J. Org. Chem. 68, 6788-6790.]). For graph-set notation, see: Bernstein et al. (1994[Bernstein, J., Etter, M. C. & Leiserowitz, L. (1994). Structure Correlation, edited by H.-B. Bürgi & J. D. Dunitz, Vol. 2, pp. 431-507. New York: VCH.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11BrClN3

  • Mr = 360.64

  • Monoclinic, C 2/c

  • a = 39.343 (8) Å

  • b = 3.851 (2) Å

  • c = 22.620 (6) Å

  • β = 123.81 (2)°

  • V = 2847.6 (18) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.07 mm−1

  • T = 173 (2) K

  • 0.20 × 0.03 × 0.02 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.579, Tmax = 0.941

  • 8088 measured reflections

  • 2589 independent reflections

  • 1944 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.094

  • S = 1.05

  • 2589 reflections

  • 203 parameters

  • 4 restraints

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

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯Br1i 0.92 (4) 2.97 (4) 3.803 (4) 153 (3)
N3—H3A⋯Br1ii 0.92 (4) 3.11 (4) 3.540 (4) 111 (3)
N3—H3B⋯N2iii 0.80 (4) 2.28 (5) 3.073 (5) 174 (4)
Symmetry codes: (i) [x, -y+2, z+{\script{1\over 2}}]; (ii) [x, -y+1, z+{\script{1\over 2}}]; (iii) -x, -y+2, -z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Pyrimidines are a class of biologically active compounds having utility in the pharmaceutical and the agrochemical industries. Compounds with the ring system show pharmacological activity such as antitumor (Gangjee et al., 1999; Grivsky et al., 1980), antiviral (Rao et al., 2003), anti-HIV (Malik et al., 2006), etc. In continuation of our research work (Bukhari et al., 2008), we have prepared several pyrimidines. In this article, we report the crystal structure of the title compound, (I).

The structure of (I), (Fig. 1), contains dimeric pairs of molecules lying about inversion centers resulting from N3—H3B···N2iii hydrogen bonds (N3···N2 = 3.071 (5) Å; Table 1 and Fig. 2). The 8-membered rings thus formed represent R22(8) motif in the graph set notation (Bernstein et al., 1994). The second H-atom of the amine, N3A, shows rather week interactions with two Br atoms representing bifurcated hydrogen bonds (H3A···Br1 2.97 (4) and 3.11 (4) Å). The mean-planes of the two phenyl rings, C5—C10 and C11—C16, are oriented with respect to the mean-plane of the heterocyclic ring at 8.98 (15) and 35.58 (10)°, respectively. The molecular dimensions in (I) agree with the corresponding molecular dimensions reported for 4,6-(diphenyl)pyrimidin-2-amine (Gallagher et al., 2004; Fun et al., 2006). The structure is devoid of any C—H···π(arene) contacts observed in the structures reported above.

Related literature top

For related structures, see: Bukhari et al. (2008); Fun et al. (2006); Gallagher et al. (2004). For pharmacological activities of pyrimidines, see: Gangjee et al. (1999); Grivsky et al. (1980); Malik et al. (2006); Rao et al. (2003). For graph-set notation, see: Bernstein et al. (1994). Please check added text.

Experimental top

The title compound was synthesized by the procedure reported earlier (Bukhari et al., 2008). Crystals of (I) suitable for crystallographic analysis were grown by slow evaporation at 313 K from a solutuion of CHCl3 (Yield 58%; m.p. 512–514 K).

Refinement top

The Br and Cl atoms showed substitutional disorder with site occupancy factors refined for Br1 and Cl1 to 0.559 (2) and Br1' and Cl1' to 0.401 (2) values. C—Cl and C—Br distances were constrained using DFIX command in SHELXL97 (Sheldrick, 2008). Though all the H atoms could be distinguished in the difference Fourier map the H-atoms bonded to C-atoms were included at geometrically idealized positions and refined in riding-model approximation with the following constraints: C—H distances were set to 0.95 Å and Uiso(H) = 1.2Ueq(C). H-atoms bonded to N3 were taken from the difference map and were allowed to refine with Uiso = 1.2 times Ueq of the parent atom. The final difference map was free of any chemically significant features.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: 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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 50% probability level. Hollow bonds represent smaller fractions of the disordered Br and Cl atoms (Br1 and Cl1, respectively).
[Figure 2] Fig. 2. Unit cell packing of (I) showing hydrogen bonds with dashed lines; H-atoms not involved in H-bonds have been omitted.
4-(4-Bromophenyl)-6-(4-chlorophenyl)pyrimidin-2-ylamine top
Crystal data top
C16H11BrClN3F(000) = 1440
Mr = 360.64Dx = 1.682 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8088 reflections
a = 39.343 (8) Åθ = 3.1–25.3°
b = 3.851 (2) ŵ = 3.07 mm1
c = 22.620 (6) ÅT = 173 K
β = 123.81 (2)°Needle, colorless
V = 2847.6 (18) Å30.20 × 0.03 × 0.02 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
2589 independent reflections
Radiation source: fine-focus sealed tube1944 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω and ϕ scansθmax = 25.3°, θmin = 3.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 4645
Tmin = 0.579, Tmax = 0.941k = 44
8088 measured reflectionsl = 2626
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0319P)2 + 9.7534P]
where P = (Fo2 + 2Fc2)/3
2589 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.43 e Å3
4 restraintsΔρmin = 0.58 e Å3
Crystal data top
C16H11BrClN3V = 2847.6 (18) Å3
Mr = 360.64Z = 8
Monoclinic, C2/cMo Kα radiation
a = 39.343 (8) ŵ = 3.07 mm1
b = 3.851 (2) ÅT = 173 K
c = 22.620 (6) Å0.20 × 0.03 × 0.02 mm
β = 123.81 (2)°
Data collection top
Nonius KappaCCD
diffractometer
2589 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
1944 reflections with I > 2σ(I)
Tmin = 0.579, Tmax = 0.941Rint = 0.048
8088 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0394 restraints
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.43 e Å3
2589 reflectionsΔρmin = 0.58 e Å3
203 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*/UeqOcc. (<1)
Br10.07275 (3)0.3788 (4)0.23596 (6)0.0284 (2)0.599 (2)
Cl10.28850 (8)0.8754 (7)0.45607 (13)0.0257 (5)0.599 (2)
Br1'0.28731 (6)0.8681 (5)0.47100 (9)0.0284 (2)0.401 (2)
Cl1'0.08059 (14)0.3789 (17)0.2222 (2)0.0257 (5)0.401 (2)
N10.09743 (9)0.9631 (7)0.16544 (15)0.0239 (6)
N20.05683 (9)0.8645 (8)0.03909 (15)0.0231 (6)
N30.02841 (10)1.0562 (9)0.09907 (18)0.0302 (8)
H3A0.0318 (12)1.151 (11)0.139 (2)0.036*
H3B0.0070 (14)1.073 (11)0.061 (2)0.036*
C10.06220 (11)0.9592 (9)0.10129 (18)0.0239 (8)
C20.13100 (11)0.8621 (9)0.16862 (18)0.0223 (7)
C30.12903 (11)0.7667 (9)0.10744 (18)0.0249 (8)
H30.15290.69950.10950.030*
C40.09094 (11)0.7729 (9)0.04318 (18)0.0223 (8)
C50.16972 (10)0.8644 (9)0.24074 (18)0.0233 (7)
C60.17017 (11)1.0069 (9)0.29802 (19)0.0261 (8)
H60.14581.10410.29010.031*
C70.20533 (11)1.0093 (10)0.3658 (2)0.0291 (8)
H70.20531.10650.40440.035*
C80.24065 (9)0.8673 (10)0.37647 (15)0.0283 (8)
C90.24130 (11)0.7212 (10)0.3213 (2)0.0294 (8)
H90.26580.62240.32970.035*
C100.20581 (11)0.7210 (9)0.25364 (19)0.0267 (8)
H100.20600.62160.21540.032*
C110.08642 (11)0.6800 (9)0.02477 (18)0.0233 (8)
C120.05169 (11)0.5079 (9)0.07802 (19)0.0244 (8)
H120.03080.44840.07080.029*
C130.04712 (11)0.4215 (9)0.14167 (18)0.0245 (8)
H130.02330.30470.17820.029*
C140.07789 (11)0.5087 (9)0.15093 (16)0.0239 (8)
C150.11279 (11)0.6792 (9)0.09883 (19)0.0270 (8)
H150.13360.73720.10620.032*
C160.11689 (11)0.7644 (9)0.03569 (19)0.0255 (8)
H160.14080.88180.00060.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0312 (5)0.0367 (4)0.0141 (5)0.0009 (4)0.0106 (4)0.0020 (4)
Cl10.0220 (8)0.0441 (11)0.0050 (9)0.0017 (7)0.0039 (7)0.0014 (7)
Br1'0.0312 (5)0.0367 (4)0.0141 (5)0.0009 (4)0.0106 (4)0.0020 (4)
Cl1'0.0220 (8)0.0441 (11)0.0050 (9)0.0017 (7)0.0039 (7)0.0014 (7)
N10.0256 (16)0.0279 (16)0.0216 (14)0.0007 (13)0.0152 (13)0.0007 (12)
N20.0241 (15)0.0273 (15)0.0228 (14)0.0024 (13)0.0161 (13)0.0015 (13)
N30.0247 (16)0.045 (2)0.0243 (16)0.0089 (16)0.0157 (14)0.0010 (16)
C10.0259 (18)0.0262 (19)0.0234 (18)0.0024 (15)0.0161 (16)0.0030 (15)
C20.0280 (19)0.0195 (17)0.0249 (18)0.0003 (15)0.0181 (16)0.0022 (15)
C30.0226 (18)0.0301 (19)0.0265 (19)0.0036 (15)0.0164 (17)0.0014 (15)
C40.0260 (19)0.0199 (17)0.0246 (18)0.0010 (14)0.0163 (17)0.0034 (14)
C50.0240 (18)0.0244 (18)0.0250 (18)0.0002 (16)0.0159 (16)0.0019 (15)
C60.0246 (19)0.0292 (19)0.0298 (19)0.0010 (15)0.0184 (17)0.0011 (16)
C70.029 (2)0.030 (2)0.0274 (19)0.0011 (16)0.0154 (17)0.0020 (16)
C80.0229 (19)0.0275 (19)0.0270 (19)0.0033 (16)0.0092 (16)0.0027 (16)
C90.0251 (19)0.030 (2)0.035 (2)0.0061 (16)0.0181 (18)0.0052 (16)
C100.029 (2)0.029 (2)0.0276 (19)0.0001 (16)0.0193 (18)0.0004 (15)
C110.0275 (19)0.0218 (19)0.0251 (18)0.0054 (15)0.0173 (16)0.0033 (14)
C120.0262 (19)0.0240 (18)0.0267 (18)0.0029 (15)0.0169 (17)0.0010 (15)
C130.0237 (18)0.0240 (19)0.0229 (17)0.0021 (15)0.0112 (16)0.0009 (15)
C140.032 (2)0.0217 (17)0.0219 (17)0.0064 (15)0.0171 (17)0.0043 (14)
C150.0261 (19)0.033 (2)0.0278 (19)0.0024 (16)0.0190 (17)0.0043 (16)
C160.0233 (18)0.030 (2)0.0228 (18)0.0000 (16)0.0126 (16)0.0004 (15)
Geometric parameters (Å, º) top
Br1—C141.886 (3)C6—C71.380 (5)
Cl1—C81.736 (3)C6—H60.9500
Br1'—C81.891 (3)C7—C81.384 (5)
Cl1'—C141.746 (4)C7—H70.9500
N1—C11.337 (5)C8—C91.382 (5)
N1—C21.340 (4)C9—C101.384 (5)
N2—C41.340 (4)C9—H90.9500
N2—C11.352 (4)C10—H100.9500
N3—C11.354 (4)C11—C121.388 (5)
N3—H3A0.92 (4)C11—C161.391 (5)
N3—H3B0.80 (4)C12—C131.388 (5)
C2—C31.392 (5)C12—H120.9500
C2—C51.489 (5)C13—C141.380 (5)
C3—C41.391 (5)C13—H130.9500
C3—H30.9500C14—C151.380 (5)
C4—C111.489 (5)C15—C161.385 (5)
C5—C101.395 (5)C15—H150.9500
C5—C61.398 (5)C16—H160.9500
C1—N1—C2116.8 (3)C9—C8—Br1'121.8 (3)
C4—N2—C1115.4 (3)C7—C8—Br1'116.4 (3)
C1—N3—H3A118 (3)C10—C9—C8119.0 (3)
C1—N3—H3B119 (3)C10—C9—H9120.5
H3A—N3—H3B121 (4)C8—C9—H9120.5
N1—C1—N2126.8 (3)C9—C10—C5121.0 (3)
N1—C1—N3116.1 (3)C9—C10—H10119.5
N2—C1—N3117.0 (3)C5—C10—H10119.5
N1—C2—C3121.0 (3)C12—C11—C16119.2 (3)
N1—C2—C5115.7 (3)C12—C11—C4120.3 (3)
C3—C2—C5123.2 (3)C16—C11—C4120.5 (3)
C4—C3—C2117.8 (3)C11—C12—C13120.8 (3)
C4—C3—H3121.1C11—C12—H12119.6
C2—C3—H3121.1C13—C12—H12119.6
N2—C4—C3122.1 (3)C14—C13—C12118.7 (3)
N2—C4—C11116.9 (3)C14—C13—H13120.6
C3—C4—C11121.0 (3)C12—C13—H13120.6
C10—C5—C6118.4 (3)C13—C14—C15121.8 (3)
C10—C5—C2121.9 (3)C13—C14—Cl1'125.4 (3)
C6—C5—C2119.7 (3)C15—C14—Cl1'112.4 (3)
C7—C6—C5121.4 (3)C13—C14—Br1119.0 (3)
C7—C6—H6119.3C15—C14—Br1119.2 (3)
C5—C6—H6119.3C14—C15—C16118.9 (3)
C6—C7—C8118.6 (3)C14—C15—H15120.6
C6—C7—H7120.7C16—C15—H15120.6
C8—C7—H7120.7C15—C16—C11120.7 (3)
C9—C8—C7121.7 (3)C15—C16—H16119.6
C9—C8—Cl1112.9 (3)C11—C16—H16119.6
C7—C8—Cl1125.3 (3)
C2—N1—C1—N20.1 (5)C7—C8—C9—C100.8 (6)
C2—N1—C1—N3178.9 (3)Cl1—C8—C9—C10175.4 (3)
C4—N2—C1—N11.5 (5)Br1'—C8—C9—C10178.3 (3)
C4—N2—C1—N3179.5 (3)C8—C9—C10—C50.2 (6)
C1—N1—C2—C31.5 (5)C6—C5—C10—C90.4 (5)
C1—N1—C2—C5179.2 (3)C2—C5—C10—C9179.0 (3)
N1—C2—C3—C41.3 (5)N2—C4—C11—C1235.5 (5)
C5—C2—C3—C4179.5 (3)C3—C4—C11—C12145.1 (4)
C1—N2—C4—C31.7 (5)N2—C4—C11—C16144.5 (3)
C1—N2—C4—C11177.7 (3)C3—C4—C11—C1634.9 (5)
C2—C3—C4—N20.4 (5)C16—C11—C12—C130.3 (5)
C2—C3—C4—C11179.0 (3)C4—C11—C12—C13179.7 (3)
N1—C2—C5—C10170.9 (3)C11—C12—C13—C140.3 (5)
C3—C2—C5—C109.9 (5)C12—C13—C14—C150.2 (5)
N1—C2—C5—C67.7 (5)C12—C13—C14—Cl1'172.1 (4)
C3—C2—C5—C6171.5 (3)C12—C13—C14—Br1177.9 (3)
C10—C5—C6—C70.4 (5)C13—C14—C15—C160.0 (5)
C2—C5—C6—C7179.1 (3)Cl1'—C14—C15—C16173.1 (4)
C5—C6—C7—C80.1 (5)Br1—C14—C15—C16178.1 (3)
C6—C7—C8—C90.7 (6)C14—C15—C16—C110.0 (5)
C6—C7—C8—Cl1174.9 (3)C12—C11—C16—C150.1 (5)
C6—C7—C8—Br1'178.4 (3)C4—C11—C16—C15179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Br1i0.92 (4)2.97 (4)3.803 (4)153 (3)
N3—H3A···Br1ii0.92 (4)3.11 (4)3.540 (4)111 (3)
N3—H3B···N2iii0.80 (4)2.28 (5)3.073 (5)174 (4)
Symmetry codes: (i) x, y+2, z+1/2; (ii) x, y+1, z+1/2; (iii) x, y+2, z.

Experimental details

Crystal data
Chemical formulaC16H11BrClN3
Mr360.64
Crystal system, space groupMonoclinic, C2/c
Temperature (K)173
a, b, c (Å)39.343 (8), 3.851 (2), 22.620 (6)
β (°) 123.81 (2)
V3)2847.6 (18)
Z8
Radiation typeMo Kα
µ (mm1)3.07
Crystal size (mm)0.20 × 0.03 × 0.02
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.579, 0.941
No. of measured, independent and
observed [I > 2σ(I)] reflections
8088, 2589, 1944
Rint0.048
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.094, 1.05
No. of reflections2589
No. of parameters203
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.58

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Br1i0.92 (4)2.97 (4)3.803 (4)153 (3)
N3—H3A···Br1ii0.92 (4)3.11 (4)3.540 (4)111 (3)
N3—H3B···N2iii0.80 (4)2.28 (5)3.073 (5)174 (4)
Symmetry codes: (i) x, y+2, z+1/2; (ii) x, y+1, z+1/2; (iii) x, y+2, z.
 

References

First citationBernstein, J., Etter, M. C. & Leiserowitz, L. (1994). Structure Correlation, edited by H.-B. Bürgi & J. D. Dunitz, Vol. 2, pp. 431–507. New York: VCH.  Google Scholar
First citationBlessing, R. H. (1997). J. Appl. Cryst. 30, 421–426.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBukhari, M. H., Siddiqui, H. L., Chaudhary, M. A., Hussain, T. & Parvez, M. (2008). Acta Cryst. E64, o963.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFun, H.-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006). Acta Cryst. E62, o5332–o5334.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGallagher, J. F., Goswami, S., Chatterjee, B., Jana, S. & Dutta, K. (2004). Acta Cryst. C60, o229–o231.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationGangjee, A., Aldair, O. & Queener, S. F. (1999). J. Med. Chem. 42, 2447–2455.  Web of Science CrossRef PubMed CAS Google Scholar
First citationGrivsky, E. D., Lee, S., Sigel, C. W., Duch, D. S. & Nichol, C. A. (1980). J. Med. Chem. 23, 227–229.  CrossRef Web of Science Google Scholar
First citationHooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationMalik, V., Singh, P. & Kumar, S. (2006). Tetrahedron, 62, 5944–5951.  Web of Science CrossRef CAS Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationRao, M. S., Ehso, N., Sergeant, C. & Dembinski, R. (2003). J. Org. Chem. 68, 6788–6790.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds