5-Bromo-N-(3,4-dimeth-oxy-benz-yl)pyridin-2-amine.

The title compound, C(14)H(15)BrN(2)O(2), an inter-mediate in drug discovery, was synthesized by the reaction of 5-bromo-pyridin-2-amine and 3,4-dimeth-oxy-benzaldehyde. In the crystal, molecules are linked via pairs ofN-H⋯N hydrogen bonds, leading to the formation of inversion dimers. A short contact occurs between the aryl H atom (ortho position from N) and the centroid of the benzene ring.

Related literature

For the anti-tumor activity of related compounds, see: Kovala-Demertzi et al. (2007 ▶). For the anti-ulcer activity of related compounds, see: Cho et al. (2001 ▶). For the anti-viral activity of related compounds, see: Mavel et al. (2002 ▶). For the anti-microbial activity of related compounds, see: Yeong et al. (2004 ▶).

Experimental

Crystal data

C14H15BrN2O2

M = 323.18

Monoclinic,

a = 6.3202 (2) Å

b = 13.7940 (4) Å

c = 15.8582 (6) Å

β = 100.961 (4)°

V = 1357.31 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.03 mm−1

T = 130 K

0.42 × 0.30 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.509, T max = 1.000

8188 measured reflections

2384 independent reflections

2055 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.060

S = 1.03

2384 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015796/rk2346sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015796/rk2346Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015796/rk2346Isup3.cml

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

C14H15BrN2O2	F(000) = 656
Mr = 323.18	Dx = 1.582 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 3191 reflections
a = 6.3202 (2) Å	θ = 3.0–29.3°
b = 13.7940 (4) Å	µ = 3.03 mm−1
c = 15.8582 (6) Å	T = 130 K
β = 100.961 (4)°	Block, colourless
V = 1357.31 (8) Å3	0.42 × 0.30 × 0.15 mm
Z = 4

Agilent Xcalibur Eos diffractometer	2384 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2055 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 16.0874 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω–scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −15→16
Tmin = 0.509, Tmax = 1.000	l = −18→15
8188 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0214P)2 + 1.0069P] where P = (Fo2 + 2Fc2)/3
2384 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Experimental. Absorption correction: CrysAlis Pro (Agilent Technologies, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.29705 (4)	0.620125 (18)	0.137802 (17)	0.02180 (10)
O1	0.8391 (3)	1.38453 (12)	0.14221 (11)	0.0181 (4)
O2	1.1319 (3)	1.40582 (12)	0.05188 (11)	0.0185 (4)
N1	0.4443 (3)	0.89466 (14)	0.06525 (13)	0.0164 (5)
N2	0.7225 (3)	1.00200 (15)	0.10747 (13)	0.0178 (5)
H2	0.6482	1.0443	0.0722	0.021*
C1	0.4393 (4)	0.74052 (17)	0.13319 (15)	0.0148 (5)
C2	0.3514 (4)	0.80926 (17)	0.07365 (16)	0.0165 (5)
H2A	0.2181	0.7951	0.0368	0.020*
C3	0.6333 (4)	0.91502 (18)	0.11831 (15)	0.0147 (5)
C4	0.7300 (4)	0.84807 (18)	0.18126 (16)	0.0177 (5)
H4	0.8617	0.8637	0.2186	0.021*
C5	0.6323 (4)	0.76009 (18)	0.18814 (16)	0.0182 (6)
H5	0.6958	0.7138	0.2297	0.022*
C6	0.9380 (4)	1.02800 (18)	0.15245 (16)	0.0176 (6)
H6A	1.0436	0.9803	0.1387	0.021*
H6B	0.9432	1.0263	0.2152	0.021*
C7	0.9971 (4)	1.12777 (17)	0.12650 (15)	0.0154 (5)
C8	0.8867 (4)	1.20894 (18)	0.14866 (15)	0.0153 (5)
H8	0.7767	1.2007	0.1814	0.018*
C9	0.9355 (4)	1.30058 (17)	0.12366 (15)	0.0144 (5)
C10	1.0981 (4)	1.31318 (18)	0.07442 (15)	0.0148 (5)
C11	1.2084 (4)	1.23269 (18)	0.05377 (16)	0.0175 (6)
H11	1.3198	1.2404	0.0217	0.021*
C12	1.1576 (4)	1.14027 (18)	0.07967 (16)	0.0175 (6)
H12	1.2342	1.0856	0.0649	0.021*
C13	0.6735 (4)	1.37654 (19)	0.19176 (17)	0.0209 (6)
H13A	0.5605	1.3329	0.1627	0.031*
H13B	0.6116	1.4407	0.1979	0.031*
H13C	0.7347	1.3506	0.2487	0.031*
C14	1.2631 (4)	1.41893 (19)	−0.01160 (17)	0.0214 (6)
H14A	1.2102	1.3772	−0.0611	0.032*
H14B	1.4126	1.4018	0.0130	0.032*
H14C	1.2564	1.4868	−0.0301	0.032*

	U11	U22	U33	U12	U13	U23
Br1	0.02543 (15)	0.01635 (15)	0.02437 (16)	−0.00657 (11)	0.00660 (11)	0.00055 (11)
O1	0.0203 (9)	0.0166 (9)	0.0204 (10)	0.0020 (7)	0.0109 (8)	0.0025 (8)
O2	0.0218 (9)	0.0140 (9)	0.0227 (10)	−0.0044 (7)	0.0116 (8)	−0.0004 (7)
N1	0.0156 (10)	0.0169 (11)	0.0153 (11)	−0.0021 (9)	−0.0002 (9)	0.0000 (9)
N2	0.0173 (10)	0.0137 (11)	0.0193 (12)	−0.0020 (9)	−0.0044 (9)	0.0042 (9)
C1	0.0196 (12)	0.0115 (13)	0.0146 (13)	−0.0018 (10)	0.0067 (11)	−0.0018 (10)
C2	0.0154 (12)	0.0180 (13)	0.0155 (14)	−0.0032 (10)	0.0017 (11)	−0.0036 (11)
C3	0.0146 (12)	0.0162 (13)	0.0131 (13)	−0.0010 (10)	0.0024 (10)	−0.0010 (10)
C4	0.0163 (12)	0.0185 (13)	0.0161 (14)	−0.0007 (10)	−0.0021 (11)	0.0030 (11)
C5	0.0194 (13)	0.0185 (14)	0.0167 (14)	0.0007 (11)	0.0037 (11)	0.0045 (11)
C6	0.0136 (12)	0.0178 (14)	0.0194 (14)	−0.0014 (10)	−0.0014 (11)	0.0006 (11)
C7	0.0145 (12)	0.0159 (13)	0.0135 (13)	−0.0030 (10)	−0.0034 (10)	−0.0010 (10)
C8	0.0136 (12)	0.0197 (14)	0.0124 (13)	−0.0030 (10)	0.0019 (10)	0.0018 (10)
C9	0.0121 (12)	0.0176 (13)	0.0129 (13)	0.0002 (10)	0.0008 (10)	−0.0018 (11)
C10	0.0138 (12)	0.0168 (13)	0.0129 (13)	−0.0033 (10)	0.0000 (10)	−0.0018 (10)
C11	0.0145 (12)	0.0213 (14)	0.0180 (14)	−0.0034 (11)	0.0061 (11)	−0.0018 (11)
C12	0.0157 (12)	0.0150 (14)	0.0212 (14)	0.0003 (10)	0.0018 (11)	−0.0039 (11)
C13	0.0179 (12)	0.0259 (15)	0.0206 (14)	0.0019 (11)	0.0076 (11)	−0.0013 (12)
C14	0.0215 (13)	0.0210 (14)	0.0236 (15)	−0.0048 (11)	0.0095 (12)	0.0014 (12)

Br1—C1	1.897 (2)	C6—H6B	0.9900
O1—C9	1.366 (3)	C6—C7	1.504 (3)
O1—C13	1.427 (3)	C7—C8	1.399 (3)
O2—C10	1.355 (3)	C7—C12	1.377 (3)
O2—C14	1.432 (3)	C8—H8	0.9500
N1—C2	1.334 (3)	C8—C9	1.377 (3)
N1—C3	1.353 (3)	C9—C10	1.414 (3)
N2—H2	0.8800	C10—C11	1.383 (3)
N2—C3	1.350 (3)	C11—H11	0.9500
N2—C6	1.457 (3)	C11—C12	1.395 (3)
C1—C2	1.378 (3)	C12—H12	0.9500
C1—C5	1.384 (3)	C13—H13A	0.9800
C2—H2A	0.9500	C13—H13B	0.9800
C3—C4	1.411 (3)	C13—H13C	0.9800
C4—H4	0.9500	C14—H14A	0.9800
C4—C5	1.375 (3)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800
C6—H6A	0.9900
C9—O1—C13	117.18 (18)	C12—C7—C8	119.3 (2)
C10—O2—C14	116.51 (18)	C7—C8—H8	119.6
C2—N1—C3	118.3 (2)	C9—C8—C7	120.8 (2)
C3—N2—H2	119.0	C9—C8—H8	119.6
C3—N2—C6	122.0 (2)	O1—C9—C8	125.6 (2)
C6—N2—H2	119.0	O1—C9—C10	114.5 (2)
C2—C1—Br1	119.77 (18)	C8—C9—C10	119.8 (2)
C2—C1—C5	119.3 (2)	O2—C10—C9	115.4 (2)
C5—C1—Br1	120.93 (18)	O2—C10—C11	125.6 (2)
N1—C2—C1	123.2 (2)	C11—C10—C9	118.9 (2)
N1—C2—H2A	118.4	C10—C11—H11	119.7
C1—C2—H2A	118.4	C10—C11—C12	120.6 (2)
N1—C3—C4	121.1 (2)	C12—C11—H11	119.7
N2—C3—N1	116.5 (2)	C7—C12—C11	120.5 (2)
N2—C3—C4	122.4 (2)	C7—C12—H12	119.8
C3—C4—H4	120.2	C11—C12—H12	119.8
C5—C4—C3	119.5 (2)	O1—C13—H13A	109.5
C5—C4—H4	120.2	O1—C13—H13B	109.5
C1—C5—H5	120.7	O1—C13—H13C	109.5
C4—C5—C1	118.5 (2)	H13A—C13—H13B	109.5
C4—C5—H5	120.7	H13A—C13—H13C	109.5
N2—C6—H6A	109.6	H13B—C13—H13C	109.5
N2—C6—H6B	109.6	O2—C14—H14A	109.5
N2—C6—C7	110.42 (19)	O2—C14—H14B	109.5
H6A—C6—H6B	108.1	O2—C14—H14C	109.5
C7—C6—H6A	109.6	H14A—C14—H14B	109.5
C7—C6—H6B	109.6	H14A—C14—H14C	109.5
C8—C7—C6	120.1 (2)	H14B—C14—H14C	109.5
C12—C7—C6	120.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.88	2.31	3.090 (3)	149
C2—H2A···Cgi	0.95	2.50	3.397 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.88	2.31	3.090 (3)	149
C2—H2A⋯Cgi	0.95	2.50	3.397 (3)	158

Symmetry code: (i) .