4-(4-Bromo-phen-yl)-6-(4-chloro-phen-yl)-pyrimidin-2-ylamine.

The title compound, C(16)H(11)BrClN(3), contains pairs of mol-ecules lying about inversion centers linked by amino-pyrimidine N-H⋯N hydrogen bonds. The eight-membered rings thus formed are represented by the R(2) (2)(8) motif in graph-set notation. The second H atom of the amine group shows a rather weak inter-action 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 = 360.64

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 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

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H11BrClN3	F(000) = 1440
Mr = 360.64	Dx = 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

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

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(Fo2) + (0.0319P)2 + 9.7534P] where P = (Fo2 + 2Fc2)/3
2589 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.43 e Å−3
4 restraints	Δρmin = −0.58 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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)

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) ; (ii) ; (iii) .