5-Bromo-N-phenyl-pyrazine-2,3-diamine.

In the title compound, C(10)H(9)BrN(4), the dihedral angle between the benzene and pyrazine rings is 61.34 (5)°. Inter-molecular N-H⋯N hydrogen bonds and N-H⋯π inter-actions assemble the mol-ecules into a three-dimensional network structure.

Related literature

For Cu or Pd catalysed C–N cross-coupling reactions, see: Fors et al. (2009 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C10H9BrN4

M = 265.12

Monoclinic,

a = 7.4834 (8) Å

b = 15.4038 (17) Å

c = 9.2079 (10) Å

β = 91.307 (2)°

V = 1061.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.85 mm−1

T = 293 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.596, T max = 0.700

5494 measured reflections

1871 independent reflections

1555 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.059

S = 1.00

1871 reflections

140 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028554/gk2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028554/gk2218Isup2.hkl

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

C10H9BrN4	F(000) = 528
Mr = 265.12	Dx = 1.660 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2474 reflections
a = 7.4834 (8) Å	θ = 2.6–27.6°
b = 15.4038 (17) Å	µ = 3.85 mm−1
c = 9.2079 (10) Å	T = 293 K
β = 91.307 (2)°	Block, colorless
V = 1061.1 (2) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	1871 independent reflections
Radiation source: fine-focus sealed tube	1555 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.596, Tmax = 0.700	k = −17→18
5494 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.025P)2 + 0.6504P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
1871 reflections	Δρmax = 0.33 e Å−3
140 parameters	Δρmin = −0.33 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0241 (11)

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
Br1	−0.05901 (4)	0.351301 (18)	1.09071 (3)	0.05020 (14)
N1	0.1466 (3)	0.39455 (14)	0.4791 (2)	0.0455 (5)
H1A	0.1000	0.4388	0.4334	0.046 (8)*
H1B	0.2400	0.3676	0.4472	0.075 (11)*
N2	−0.0254 (3)	0.43567 (13)	0.6710 (2)	0.0404 (5)
N3	0.1484 (2)	0.31467 (12)	0.84959 (19)	0.0319 (4)
N4	0.3193 (3)	0.27272 (13)	0.6497 (2)	0.0420 (5)
H4	0.2980	0.2595	0.5591	0.063 (9)*
C1	0.1017 (3)	0.38587 (14)	0.6195 (2)	0.0317 (5)
C2	0.1899 (3)	0.32331 (14)	0.7117 (2)	0.0302 (5)
C3	0.0152 (3)	0.36556 (15)	0.8955 (2)	0.0343 (5)
C4	−0.0699 (3)	0.42447 (16)	0.8104 (3)	0.0423 (6)
H4A	−0.1608	0.4579	0.8488	0.051*
C5	0.4259 (3)	0.21097 (15)	0.7267 (2)	0.0365 (6)
C6	0.4269 (4)	0.12553 (16)	0.6809 (3)	0.0446 (6)
H6	0.3565	0.1084	0.6014	0.054*
C7	0.5329 (4)	0.06590 (19)	0.7538 (3)	0.0564 (8)
H7	0.5338	0.0084	0.7229	0.068*
C8	0.6367 (4)	0.0902 (2)	0.8710 (3)	0.0613 (8)
H8	0.7056	0.0491	0.9209	0.074*
C9	0.6390 (4)	0.1748 (2)	0.9145 (3)	0.0589 (8)
H9	0.7108	0.1916	0.9934	0.071*
C10	0.5348 (3)	0.23602 (18)	0.8419 (3)	0.0468 (6)
H10	0.5383	0.2938	0.8709	0.056*

	U11	U22	U33	U12	U13	U23
Br1	0.0541 (2)	0.0615 (2)	0.03565 (17)	0.00683 (14)	0.01461 (11)	0.00123 (12)
N1	0.0648 (15)	0.0406 (12)	0.0314 (11)	0.0182 (11)	0.0047 (10)	0.0082 (9)
N2	0.0466 (13)	0.0353 (11)	0.0392 (12)	0.0102 (9)	0.0014 (9)	0.0047 (9)
N3	0.0345 (11)	0.0327 (10)	0.0288 (10)	0.0035 (8)	0.0036 (8)	0.0018 (8)
N4	0.0504 (13)	0.0451 (12)	0.0310 (11)	0.0194 (10)	0.0094 (9)	0.0070 (9)
C1	0.0369 (13)	0.0262 (11)	0.0320 (12)	0.0014 (10)	−0.0003 (10)	−0.0008 (9)
C2	0.0330 (13)	0.0265 (11)	0.0312 (12)	0.0008 (9)	0.0013 (10)	0.0001 (9)
C3	0.0375 (13)	0.0359 (13)	0.0297 (12)	−0.0004 (10)	0.0048 (10)	−0.0004 (10)
C4	0.0433 (15)	0.0400 (14)	0.0440 (15)	0.0124 (11)	0.0085 (11)	0.0005 (11)
C5	0.0339 (13)	0.0404 (14)	0.0356 (12)	0.0084 (10)	0.0107 (10)	0.0087 (11)
C6	0.0408 (15)	0.0416 (15)	0.0516 (16)	0.0068 (11)	0.0040 (12)	0.0028 (12)
C7	0.0502 (17)	0.0404 (15)	0.079 (2)	0.0149 (13)	0.0099 (15)	0.0084 (14)
C8	0.0492 (18)	0.069 (2)	0.066 (2)	0.0229 (15)	0.0049 (15)	0.0211 (16)
C9	0.0419 (16)	0.084 (2)	0.0504 (17)	0.0121 (15)	−0.0041 (13)	0.0015 (15)
C10	0.0438 (15)	0.0478 (15)	0.0489 (15)	0.0067 (12)	0.0064 (12)	−0.0016 (13)

Br1—C3	1.906 (2)	C4—H4A	0.9300
N1—C1	1.349 (3)	C5—C10	1.378 (4)
N1—H1A	0.8699	C5—C6	1.382 (3)
N1—H1B	0.8700	C6—C7	1.378 (4)
N2—C1	1.319 (3)	C6—H6	0.9300
N2—C4	1.344 (3)	C7—C8	1.368 (4)
N3—C2	1.320 (3)	C7—H7	0.9300
N3—C3	1.344 (3)	C8—C9	1.364 (4)
N4—C2	1.377 (3)	C8—H8	0.9300
N4—C5	1.420 (3)	C9—C10	1.385 (4)
N4—H4	0.8700	C9—H9	0.9300
C1—C2	1.436 (3)	C10—H10	0.9300
C3—C4	1.349 (3)
C1—N1—H1A	115.8	C3—C4—H4A	119.4
C1—N1—H1B	119.8	C10—C5—C6	119.6 (2)
H1A—N1—H1B	121.8	C10—C5—N4	120.8 (2)
C1—N2—C4	117.7 (2)	C6—C5—N4	119.5 (2)
C2—N3—C3	115.85 (19)	C7—C6—C5	119.5 (3)
C2—N4—C5	124.36 (19)	C7—C6—H6	120.2
C2—N4—H4	114.5	C5—C6—H6	120.2
C5—N4—H4	114.3	C8—C7—C6	120.8 (3)
N2—C1—N1	119.0 (2)	C8—C7—H7	119.6
N2—C1—C2	120.2 (2)	C6—C7—H7	119.6
N1—C1—C2	120.8 (2)	C9—C8—C7	119.7 (3)
N3—C2—N4	121.6 (2)	C9—C8—H8	120.1
N3—C2—C1	121.5 (2)	C7—C8—H8	120.1
N4—C2—C1	116.92 (19)	C8—C9—C10	120.4 (3)
N3—C3—C4	123.6 (2)	C8—C9—H9	119.8
N3—C3—Br1	117.62 (16)	C10—C9—H9	119.8
C4—C3—Br1	118.81 (18)	C5—C10—C9	119.8 (3)
N2—C4—C3	121.2 (2)	C5—C10—H10	120.1
N2—C4—H4A	119.4	C9—C10—H10	120.1
C4—N2—C1—N1	178.7 (2)	N3—C3—C4—N2	0.3 (4)
C4—N2—C1—C2	−1.1 (3)	Br1—C3—C4—N2	−178.49 (19)
C3—N3—C2—N4	−177.5 (2)	C2—N4—C5—C10	−59.7 (3)
C3—N3—C2—C1	2.3 (3)	C2—N4—C5—C6	123.5 (3)
C5—N4—C2—N3	−3.5 (4)	C10—C5—C6—C7	1.9 (4)
C5—N4—C2—C1	176.6 (2)	N4—C5—C6—C7	178.8 (2)
N2—C1—C2—N3	−0.9 (3)	C5—C6—C7—C8	0.1 (4)
N1—C1—C2—N3	179.4 (2)	C6—C7—C8—C9	−1.6 (5)
N2—C1—C2—N4	179.0 (2)	C7—C8—C9—C10	0.9 (5)
N1—C1—C2—N4	−0.8 (3)	C6—C5—C10—C9	−2.6 (4)
C2—N3—C3—C4	−2.1 (3)	N4—C5—C10—C9	−179.4 (2)
C2—N3—C3—Br1	176.66 (16)	C8—C9—C10—C5	1.2 (4)
C1—N2—C4—C3	1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cg1i	0.86	2.63	3.436 (3)	157
N1—H1A···N2ii	0.86	2.22	3.084 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cg1i	0.86	2.63	3.436 (3)	157
N1—H1A⋯N2ii	0.86	2.22	3.084 (3)	169

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C5–C10 ring.