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

Bukhari, M.H.; Siddiqui, H.L.; Ahmad, N.; Siddiqui, W.A.; Parvez, M.

doi:10.1107/S1600536809002748

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o390

doi:10.1107/S1600536809002748

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

Mujahid Hussain Bukhari,^a Hamid Latif Siddiqui,^a ^* Naveed Ahmad,^a Waseeq Ahmad Siddiqui ^b and Masood Parvez ^c

^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 ); 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 ).

Experimental

Crystal data

C₁₆H₁₁BrClN₃
M_r = 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 ) T_min = 0.579, T_max = 0.941
8088 measured reflections
2589 independent reflections
1944 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002748/fj2180sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002748/fj2180Isup2.hkl

checkCIF report

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).

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

	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).
	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

C₁₆H₁₁BrClN₃	F(000) = 1440
M_r = 360.64	D_x = 1.682 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8088 reflections
a = 39.343 (8) Å	θ = 3.1–25.3°
b = 3.851 (2) Å	µ = 3.07 mm⁻¹
c = 22.620 (6) Å	T = 173 K
β = 123.81 (2)°	Needle, colorless
V = 2847.6 (18) Å³	0.20 × 0.03 × 0.02 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	2589 independent reflections
Radiation source: fine-focus sealed tube	1944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω and ϕ scans	θ_max = 25.3°, θ_min = 3.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −46→45
T_min = 0.579, T_max = 0.941	k = −4→4
8088 measured reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0319P)² + 9.7534P] where P = (F_o² + 2F_c²)/3
2589 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.43 e Å⁻³
4 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₆H₁₁BrClN₃	V = 2847.6 (18) Å³
M_r = 360.64	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 39.343 (8) Å	µ = 3.07 mm⁻¹
b = 3.851 (2) Å	T = 173 K
c = 22.620 (6) Å	0.20 × 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)
T_min = 0.579, T_max = 0.941	R_int = 0.048
8088 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	4 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.43 e Å⁻³
2589 reflections	Δρ_min = −0.58 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.07275 (3)	0.3788 (4)	−0.23596 (6)	0.0284 (2)	0.599 (2)
Cl1	0.28850 (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)
N1	0.09743 (9)	0.9631 (7)	0.16544 (15)	0.0239 (6)
N2	0.05683 (9)	0.8645 (8)	0.03909 (15)	0.0231 (6)
N3	0.02841 (10)	1.0562 (9)	0.09907 (18)	0.0302 (8)
H3A	0.0318 (12)	1.151 (11)	0.139 (2)	0.036*
H3B	0.0070 (14)	1.073 (11)	0.061 (2)	0.036*
C1	0.06220 (11)	0.9592 (9)	0.10129 (18)	0.0239 (8)
C2	0.13100 (11)	0.8621 (9)	0.16862 (18)	0.0223 (7)
C3	0.12903 (11)	0.7667 (9)	0.10744 (18)	0.0249 (8)
H3	0.1529	0.6995	0.1095	0.030*
C4	0.09094 (11)	0.7729 (9)	0.04318 (18)	0.0223 (8)
C5	0.16972 (10)	0.8644 (9)	0.24074 (18)	0.0233 (7)
C6	0.17017 (11)	1.0069 (9)	0.29802 (19)	0.0261 (8)
H6	0.1458	1.1041	0.2901	0.031*
C7	0.20533 (11)	1.0093 (10)	0.3658 (2)	0.0291 (8)
H7	0.2053	1.1065	0.4044	0.035*
C8	0.24065 (9)	0.8673 (10)	0.37647 (15)	0.0283 (8)
C9	0.24130 (11)	0.7212 (10)	0.3213 (2)	0.0294 (8)
H9	0.2658	0.6224	0.3297	0.035*
C10	0.20581 (11)	0.7210 (9)	0.25364 (19)	0.0267 (8)
H10	0.2060	0.6216	0.2154	0.032*
C11	0.08642 (11)	0.6800 (9)	−0.02477 (18)	0.0233 (8)
C12	0.05169 (11)	0.5079 (9)	−0.07802 (19)	0.0244 (8)
H12	0.0308	0.4484	−0.0708	0.029*
C13	0.04712 (11)	0.4215 (9)	−0.14167 (18)	0.0245 (8)
H13	0.0233	0.3047	−0.1782	0.029*
C14	0.07789 (11)	0.5087 (9)	−0.15093 (16)	0.0239 (8)
C15	0.11279 (11)	0.6792 (9)	−0.09883 (19)	0.0270 (8)
H15	0.1336	0.7372	−0.1062	0.032*
C16	0.11689 (11)	0.7644 (9)	−0.03569 (19)	0.0255 (8)
H16	0.1408	0.8818	0.0006	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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)
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)
N1	0.0256 (16)	0.0279 (16)	0.0216 (14)	0.0007 (13)	0.0152 (13)	0.0007 (12)
N2	0.0241 (15)	0.0273 (15)	0.0228 (14)	0.0024 (13)	0.0161 (13)	0.0015 (13)
N3	0.0247 (16)	0.045 (2)	0.0243 (16)	0.0089 (16)	0.0157 (14)	0.0010 (16)
C1	0.0259 (18)	0.0262 (19)	0.0234 (18)	0.0024 (15)	0.0161 (16)	0.0030 (15)
C2	0.0280 (19)	0.0195 (17)	0.0249 (18)	0.0003 (15)	0.0181 (16)	0.0022 (15)
C3	0.0226 (18)	0.0301 (19)	0.0265 (19)	0.0036 (15)	0.0164 (17)	0.0014 (15)
C4	0.0260 (19)	0.0199 (17)	0.0246 (18)	0.0010 (14)	0.0163 (17)	0.0034 (14)
C5	0.0240 (18)	0.0244 (18)	0.0250 (18)	0.0002 (16)	0.0159 (16)	0.0019 (15)
C6	0.0246 (19)	0.0292 (19)	0.0298 (19)	0.0010 (15)	0.0184 (17)	0.0011 (16)
C7	0.029 (2)	0.030 (2)	0.0274 (19)	−0.0011 (16)	0.0154 (17)	−0.0020 (16)
C8	0.0229 (19)	0.0275 (19)	0.0270 (19)	−0.0033 (16)	0.0092 (16)	0.0027 (16)
C9	0.0251 (19)	0.030 (2)	0.035 (2)	0.0061 (16)	0.0181 (18)	0.0052 (16)
C10	0.029 (2)	0.029 (2)	0.0276 (19)	−0.0001 (16)	0.0193 (18)	0.0004 (15)
C11	0.0275 (19)	0.0218 (19)	0.0251 (18)	0.0054 (15)	0.0173 (16)	0.0033 (14)
C12	0.0262 (19)	0.0240 (18)	0.0267 (18)	0.0029 (15)	0.0169 (17)	0.0010 (15)
C13	0.0237 (18)	0.0240 (19)	0.0229 (17)	0.0021 (15)	0.0112 (16)	−0.0009 (15)
C14	0.032 (2)	0.0217 (17)	0.0219 (17)	0.0064 (15)	0.0171 (17)	0.0043 (14)
C15	0.0261 (19)	0.033 (2)	0.0278 (19)	0.0024 (16)	0.0190 (17)	0.0043 (16)
C16	0.0233 (18)	0.030 (2)	0.0228 (18)	0.0000 (16)	0.0126 (16)	−0.0004 (15)

Geometric parameters (Å, º) top

Br1—C14	1.886 (3)	C6—C7	1.380 (5)
Cl1—C8	1.736 (3)	C6—H6	0.9500
Br1'—C8	1.891 (3)	C7—C8	1.384 (5)
Cl1'—C14	1.746 (4)	C7—H7	0.9500
N1—C1	1.337 (5)	C8—C9	1.382 (5)
N1—C2	1.340 (4)	C9—C10	1.384 (5)
N2—C4	1.340 (4)	C9—H9	0.9500
N2—C1	1.352 (4)	C10—H10	0.9500
N3—C1	1.354 (4)	C11—C12	1.388 (5)
N3—H3A	0.92 (4)	C11—C16	1.391 (5)
N3—H3B	0.80 (4)	C12—C13	1.388 (5)
C2—C3	1.392 (5)	C12—H12	0.9500
C2—C5	1.489 (5)	C13—C14	1.380 (5)
C3—C4	1.391 (5)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.380 (5)
C4—C11	1.489 (5)	C15—C16	1.385 (5)
C5—C10	1.395 (5)	C15—H15	0.9500
C5—C6	1.398 (5)	C16—H16	0.9500

C1—N1—C2	116.8 (3)	C9—C8—Br1'	121.8 (3)
C4—N2—C1	115.4 (3)	C7—C8—Br1'	116.4 (3)
C1—N3—H3A	118 (3)	C10—C9—C8	119.0 (3)
C1—N3—H3B	119 (3)	C10—C9—H9	120.5
H3A—N3—H3B	121 (4)	C8—C9—H9	120.5
N1—C1—N2	126.8 (3)	C9—C10—C5	121.0 (3)
N1—C1—N3	116.1 (3)	C9—C10—H10	119.5
N2—C1—N3	117.0 (3)	C5—C10—H10	119.5
N1—C2—C3	121.0 (3)	C12—C11—C16	119.2 (3)
N1—C2—C5	115.7 (3)	C12—C11—C4	120.3 (3)
C3—C2—C5	123.2 (3)	C16—C11—C4	120.5 (3)
C4—C3—C2	117.8 (3)	C11—C12—C13	120.8 (3)
C4—C3—H3	121.1	C11—C12—H12	119.6
C2—C3—H3	121.1	C13—C12—H12	119.6
N2—C4—C3	122.1 (3)	C14—C13—C12	118.7 (3)
N2—C4—C11	116.9 (3)	C14—C13—H13	120.6
C3—C4—C11	121.0 (3)	C12—C13—H13	120.6
C10—C5—C6	118.4 (3)	C13—C14—C15	121.8 (3)
C10—C5—C2	121.9 (3)	C13—C14—Cl1'	125.4 (3)
C6—C5—C2	119.7 (3)	C15—C14—Cl1'	112.4 (3)
C7—C6—C5	121.4 (3)	C13—C14—Br1	119.0 (3)
C7—C6—H6	119.3	C15—C14—Br1	119.2 (3)
C5—C6—H6	119.3	C14—C15—C16	118.9 (3)
C6—C7—C8	118.6 (3)	C14—C15—H15	120.6
C6—C7—H7	120.7	C16—C15—H15	120.6
C8—C7—H7	120.7	C15—C16—C11	120.7 (3)
C9—C8—C7	121.7 (3)	C15—C16—H16	119.6
C9—C8—Cl1	112.9 (3)	C11—C16—H16	119.6
C7—C8—Cl1	125.3 (3)

C2—N1—C1—N2	−0.1 (5)	C7—C8—C9—C10	0.8 (6)
C2—N1—C1—N3	178.9 (3)	Cl1—C8—C9—C10	−175.4 (3)
C4—N2—C1—N1	−1.5 (5)	Br1'—C8—C9—C10	178.3 (3)
C4—N2—C1—N3	179.5 (3)	C8—C9—C10—C5	−0.2 (6)
C1—N1—C2—C3	1.5 (5)	C6—C5—C10—C9	−0.4 (5)
C1—N1—C2—C5	−179.2 (3)	C2—C5—C10—C9	−179.0 (3)
N1—C2—C3—C4	−1.3 (5)	N2—C4—C11—C12	−35.5 (5)
C5—C2—C3—C4	179.5 (3)	C3—C4—C11—C12	145.1 (4)
C1—N2—C4—C3	1.7 (5)	N2—C4—C11—C16	144.5 (3)
C1—N2—C4—C11	−177.7 (3)	C3—C4—C11—C16	−34.9 (5)
C2—C3—C4—N2	−0.4 (5)	C16—C11—C12—C13	−0.3 (5)
C2—C3—C4—C11	179.0 (3)	C4—C11—C12—C13	179.7 (3)
N1—C2—C5—C10	170.9 (3)	C11—C12—C13—C14	0.3 (5)
C3—C2—C5—C10	−9.9 (5)	C12—C13—C14—C15	−0.2 (5)
N1—C2—C5—C6	−7.7 (5)	C12—C13—C14—Cl1'	172.1 (4)
C3—C2—C5—C6	171.5 (3)	C12—C13—C14—Br1	177.9 (3)
C10—C5—C6—C7	0.4 (5)	C13—C14—C15—C16	0.0 (5)
C2—C5—C6—C7	179.1 (3)	Cl1'—C14—C15—C16	−173.1 (4)
C5—C6—C7—C8	0.1 (5)	Br1—C14—C15—C16	−178.1 (3)
C6—C7—C8—C9	−0.7 (6)	C14—C15—C16—C11	0.0 (5)
C6—C7—C8—Cl1	174.9 (3)	C12—C11—C16—C15	0.1 (5)
C6—C7—C8—Br1'	−178.4 (3)	C4—C11—C16—C15	−179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2; (ii) x, −y+1, z+1/2; (iii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁BrClN₃
M_r	360.64
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	39.343 (8), 3.851 (2), 22.620 (6)
β (°)	123.81 (2)
V (Å³)	2847.6 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.07
Crystal size (mm)	0.20 × 0.03 × 0.02

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.579, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	8088, 2589, 1944
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.094, 1.05
No. of reflections	2589
No. of parameters	203
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+1/2; (ii) x, −y+1, z+1/2; (iii) −x, −y+2, −z.

References

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Volume 65| Part 2| February 2009| Page o390

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